Olde Cypress

Updated September 2026 · Jesse McGreevy and Marc Comisar, Domain Realty

Olde Cypress is a gated golf community of 548 single-family homes in North Naples, Florida, set behind one staffed gatehouse on Treeline Drive off Logan Boulevard North, about a quarter mile north of Immokalee Road in ZIP 34119. It wraps around a P.B. Dye golf course that opened in 1999, and every home carries a mandatory social membership in The Club at Olde Cypress. The short answer on price: the median Olde Cypress sale was $1,105,000 across 26 closings in the 12 months to September 26, 2026 (Southwest Florida MLS Matrix, pulled September 26, 2026), there is no Community Development District, club social membership is mandatory, and the only way in by car is the gate on Treeline Drive.

McGreevy and Comisar are the team Olde Cypress sellers call first, and the team buyers call when they want to know which of the nine neighborhoods backs onto the golf course, what the master association collects at closing and why the clubhouse sits outside the gate. Jesse McGreevy and Marc Comisar lead Domain Realty Group, the #1 real estate team in Southwest Florida since 2012 and Top 1% of agents nationally since 2008, with over $900 million in personal sales between them. If you are comparing agents before you list, we publish the best real estate agents in Naples, compared on the public record, so you can check the numbers yourself.

This guide makes one promise: every fact on it comes from a recorded document, the county roll, FEMA, the school district or the MLS. The covenants come from the recorded 2019 Amended and Restated Declaration for Olde Cypress. The home counts, values and taxes come from the Collier County Property Appraiser 2026 preliminary roll, and the sale history from the Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026). Flood zones come from FEMA’s effective and preliminary maps, school zones from Collier County Public Schools, and current market figures from the Southwest Florida MLS Matrix, pulled September 26, 2026. Where a number is not public, such as club dues or neighborhood association fees, we say so and name the document that holds it.

Key Takeaways: Olde Cypress at a Glance

Olde Cypress comes down to eight facts that decide most purchases and sales: how many homes there are, how you get in, what you pay beyond the mortgage, what the club requires, what homes are selling for, how prices have moved, what the lease rules allow and which public schools each street is zoned for.

Data updated: September 2026

• 548 single-family homes in nine neighborhoods. The Collier County Property Appraiser 2026 preliminary roll counts 548 single-family homes behind the gate, which the master association rounds to “550 single-family estate homes and attached villa residences” on its Olde Cypress Master Property Owners Association About page. Nine neighborhood associations sit under one master association.
• One road entrance, one gatehouse. Every street connects to the public road network at a single point, Treeline Drive at Logan Boulevard North, per Collier County’s road centerline layer. The guard house number printed on the master association’s Olde Cypress neighborhood site map is (239) 592-5381.
• No CDD. The only non-ad valorem line on a certified Collier County Tax Collector 2025 bill for a Lone Pine Lane home is “District 1 Garbage” at $261.91, against a 2025 millage rate of 9.5058 mills, and Collier County’s CDD layer shows no district over the community.
• Club social membership is mandatory; golf is optional. Section 14.02 of the 2019 Amended and Restated Declaration for Olde Cypress (OR 5700 PG 1118) makes every owner a social member of The Club at Olde Cypress. The club is non-equity, owned by Stock, says it charges no member assessments and no food and beverage minimum, and funded a $16 million clubhouse renovation that reopened in 2026.
• 26 MLS closings at a median of $1,105,000. In the 12 months to September 26, 2026, Olde Cypress homes sold at a median $472.75 per square foot of living area, a median 29 days on market and a median 97.52% of list price, all single-family, for $32,328,300 in total volume; five homes were listed for sale and one was pending on the pull date, about 2.3 months of supply (Southwest Florida MLS Matrix, pulled September 26, 2026).
• The recorded median more than doubled from 2016 to its 2023 peak. County recorded qualified sales ran from a $670,000 median in 2016 (37 sales) to $1,550,000 in 2023 (29 sales); 2026 through May 22 stands at $1,110,000 on 17 sales (Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026).
• 60-day minimum leases, four a year. No lease may run under 60 days and no home may carry more than four leases in a calendar year, under section 9.13 of the recorded 2019 Declaration and the 2013 leasing amendment for Olde Cypress (OR 4874 PG 3783), which raised the floor from 30 days.
• All three assigned schools rated A three years running. Every single-family street is zoned for Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026-2027 per the Collier County Public Schools address lookup (453 of 453 addresses agree), and all three earned an A in 2024, 2025 and 2026 state grades, as republished from Florida Department of Education data in the Naples Daily News report on 2026 Collier school grades.

Table of Contents

This Olde Cypress guide runs from the market and daily life through the Woodlands origins, the PUD and what it covers, governance and the full fee stack, all nine neighborhoods, the club, the P.B. Dye course and the 2026 clubhouse, flood maps, hurricanes and insurance, schools, location and what is being built nearby, then comparisons, the honest pros and cons, selling, and two full FAQs.

• Key Takeaways: Olde Cypress at a Glance
• Why McGreevy and Comisar Are the Best Realtor for Olde Cypress
• What Is It Like to Live in Olde Cypress as a Homebuyer?
• Olde Cypress Real Estate Market Snapshot
• How Did Olde Cypress Begin? The Woodlands Land, the Stock Family and the PUD
• What Is Inside the Olde Cypress PUD, and What Is Not Olde Cypress?
• Who Governs Olde Cypress? The Master Association and Nine Neighborhoods
• How Much Does It Cost to Live in Olde Cypress? The Fee Stack
• What Are the Neighborhoods Inside Olde Cypress?
• Is Membership at The Club at Olde Cypress Mandatory?
• What Is the Olde Cypress Golf Course Like?
• What Changed in the $16 Million Clubhouse Renovation?
• Tennis, Pickleball, Fitness, Pool and Dining at Olde Cypress
• Is Olde Cypress in a Flood Zone? FEMA Zones by Neighborhood
• Hurricane Posture: Evacuation Zone, Storm Surge and Wind Code
• What Does Home Insurance Cost in Olde Cypress?
• Which Schools Serve Olde Cypress?
• Hospitals, ERs and Healthcare Near Olde Cypress
• Where Is Olde Cypress? Location, Entrance and Drive Times
• Shopping, Beaches, Parks and Daily Life Near Olde Cypress
• What Is Being Built Near Olde Cypress?
• Olde Cypress vs The Vineyards: Which North Naples Golf Community Fits You?
• How Does Olde Cypress Compare With Other North Naples Communities?
• The Honest Pros and Cons of Olde Cypress
• Thinking of Selling Your Olde Cypress Home? List With the #1 Team in Southwest Florida Since 2012
• Your Local Real Estate Experts
• Olde Cypress FAQ: Buyer Edition
• Olde Cypress FAQ: Seller Edition
• Sources
• Downloadable Documents

Why McGreevy and Comisar Are the Best Realtor for Olde Cypress

McGreevy and Comisar are the best realtor for Olde Cypress because the case is on the record: the #1 team in Southwest Florida since 2012, Top 1% of agents nationally since 2008, over $900 million in personal sales, and an Olde Cypress market read built on every MLS closing, the county roll, FEMA’s map changes and the recorded Declaration.

Data updated: September 2026

If you’re searching for the best realtor for Olde Cypress, whether you’re ready to sell your Olde Cypress home or buy your next one, McGreevy and Comisar is the team that delivers. We lead Domain Realty Group, the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 billion sold as a team and $900 million in personal sales between Jesse and Marc. Put another way, as the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate.

Recent Olde Cypress track record (last 12 months): In the last 12 months we tracked 26 Olde Cypress closings in the Southwest Florida MLS Matrix, pulled September 26, 2026, every one of them a single-family home: 26 homes and $32.3 million in volume ($32,328,300). The median sold price was $1,105,000 (an even count, so the mean of the middle pair, $1,100,000 and $1,110,000), the median time on market was 29 days (24 of the 26 sales; two were entered after closing without a marketing period), the median sold-to-list ratio was 97.52% and the median price per square foot of living area was $472.75. The highest sale was $2,990,000, a Da Vinci Estates home in January 2026 that was entered after closing, and the fastest was 0 days: a Lantana home that went under contract in 0 days and sold at its full $1,735,000 list price in January 2026. There were no builder-direct sales in the window: Olde Cypress is a resale market, so every buyer is competing for a home someone already lives in, and every seller is competing against the other homes on the market that week.

For luxury Olde Cypress sellers: Premium marketing, including cinematic video, drone, professional photography, a qualified-buyer database, and discretion with off-market capability when needed. An Olde Cypress sale also runs on paperwork that has to be ordered early. The master association collects a working capital contribution “at the time of the transfer of title of any Parcel” in an amount “as the Board may from time to time determine,” under section 8.13 of the 2019 Amended and Restated Declaration for Olde Cypress, and the amount is not published, so we confirm it through the estoppel certificate before your buyer’s numbers are final. Your neighborhood association bills quarterly, and that invoice includes the master association share, per the master association’s About page. The club transfer matters too: your buyer becomes a social member automatically, and golf is a separate purchase, so the buyer who wants golf needs the club’s current membership terms from the club’s membership office at (239) 596-4797 early in the contract. Marketing inside the gate follows the master association’s information page for real estate agents: public open houses only on Saturday and Sunday from noon to 5 p.m., open-house signs issued at the guard house against a $20 refundable deposit, and one standardized green For Sale sign. Those rules reward a seller whose agent plans the showing calendar around them.

Honors and recognition:

• Top 1% Real Estate Agents Nationally Since 2008
• 5 Star Award for Customer Satisfaction for 21 Straight Years. Only 5 out of 21k+ Licensees (Gulfshore Life Magazine)
• #1 Team in Southwest Florida since 2012
• McGreevy and Comisar and their Domain Realty Group team have sold over $2.5 Billion in Real Estate
• McGreevy and Comisar alone have over $900 million in Sales
• Nationally Recognized Top Producing Realtors
• Platinum Sales Production Award Winners

McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com.

Selling your Olde Cypress home? Get a free valuation of your Olde Cypress home, or Call Jesse direct at (239) 898-6072. Confidential conversations are welcome for luxury listings.

Buying a home in Olde Cypress? Call Marc at (239) 287-5873 for a personalized buyer consultation, or read how we represent buyers in Southwest Florida.

Office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134 · Jesse McGreevy: (239) 898-6072 · [email protected] · Marc Comisar: (239) 287-5873

Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).

What Is It Like to Live in Olde Cypress as a Homebuyer?

Living in Olde Cypress means one staffed gate on Treeline Drive, a P.B. Dye golf course threading through nine neighborhoods, a clubhouse you join automatically at the social level, 13 lakes you can look at but not swim in, and a large east-side preserve. It is a golf and club community built between 2000 and 2016.

Data updated: September 2026

The community is the Olde Cypress PUD, approved at 538.1 acres by Collier County Ordinance 2000-37, plus two neighborhoods zoned separately next door: Da Vinci Estates (its own 40.37-acre PUD) and Lantana (the H.D. Development PUD, also known as Vita Tuscana). Both are behind the same gate and both are members of the master association, because their recorded declarations subject every lot to the Olde Cypress master declaration: the Da Vinci Estates declaration at OR 2737 PG 2884 and the Lantana declaration of covenants at OR 4904 PG 1443. The master association describes the whole as about 540 acres. The golf course itself is not common property: the course and clubhouse parcels are owned by a Stock entity, and the Declaration says they “are not Common Areas, being owned and operated by a separate entity.”

The Gate and the Drive In

There is one way in by car. You turn off Immokalee Road onto Logan Boulevard North, drive about a quarter mile north, and turn east onto Treeline Drive. Collier County’s road centerline layer shows that every street inside, from Olde Cypress Drive to Lantana Circle to Mona Lisa Boulevard, connects to the public road network only through that point; neither Treeline Drive nor Olde Cypress Drive touches Immokalee Road, and there is no “Olde Cypress Boulevard” entrance, whatever older documents say. Section 3.05 of the 2019 Amended and Restated Declaration for Olde Cypress records the ownership split: Logan Boulevard up to the entrance, and Treeline Drive from Logan to “the traffic control gate,” are dedicated to the public, and the rest of Treeline Drive belongs to the master association.

The gatehouse has a resident lane and a guest lane and is run by a third-party attendant company using the Dwelling Live access system, per the master association’s Olde Cypress community access guide. Prospective buyers enter with an agent, with the owner, or after a homeowner phones the guard house, except during weekend open-house hours, per the association’s information page for real estate agents. The Declaration is also plain that the association does not warrant “any monitoring system, guardhouse, traffic control gate or security service,” which is standard language and worth knowing.

Here is the detail that confuses first-time visitors: the clubhouse is outside the gate. The club’s About Us page says “the club is conveniently located outside the community’s gates,” and the master association’s site map draws the clubhouse, tennis courts and practice range west of the gatehouse at 7165 Treeline Drive. That is why non-residents can join for golf without passing security, and why the homes remain gated even though the club is not. One more naming point: Fairway Preserve at Olde Cypress, a 264-unit condominium on Preserve Circle, carries the name but is not inside this gate or part of the master association; it has its own entrance off Immokalee Road by way of Dancing Wind Lane.

The Club Question Every Buyer Faces

Every Olde Cypress purchase includes the club. Section 14.02 of the recorded Declaration reads: “By acquisition of a Parcel, each Owner automatically becomes a social member of The Club at Olde Cypress,” with dues “as promulgated by The Club … from time to time,” and section 14.03 says owners receive no equity, voting or ownership interest in the club property. The club’s membership page confirms that social membership “is mandatory for all residents of the Olde Cypress community who do not hold a higher category of membership,” and that it “is only available to those residing within the gates.” Social members get clubhouse dining, parties, tennis, pickleball and fitness; golf is not included except as a golf member’s guest.

Golf is a choice layered on top. The club sells Full Golf and Associate Golf memberships, and as of September 2026 both are listed as available to residents and non-residents. Associate Golf gives limited golf from November through April and unlimited golf from May through October. The club describes itself as “non-equity, privately owned,” and its About Us page says there are no member assessments for improvements and no food and beverage minimums. The club’s own explainer on equity versus non-equity club memberships spells out what non-equity means: not subject to assessments, non-transferable, no ownership, easy to resign. The one published dollar figure is the private-cart fee: members who want to use their own golf cart on the course pay $1,950 a year, and the club says about 60% do, per its post on five things to know about Naples private golf clubs.

What the club does not publish is initiation or annual dues. Its fact sheet and golf guide sit behind lead forms. Third-party figures that circulate online conflict widely, from roughly $45,000 to $175,000 for golf initiation, and none of them is club-published, so we do not repeat them as fact. The current number comes from the club’s membership office at (239) 596-4797 and belongs in the contract review, alongside the social dues every owner pays.

The course is the reason many buyers come. It is an 18-hole, par-72 P.B. Dye design, built in 1999 and described in Golfweek’s 2021 report on the course renovation as the first P.B. Dye course in Collier County. That 2021 work resurfaced all 18 greens with TifEagle Bermuda, rebuilt the drainage and refreshed all 98 bunkers. The club scorecard runs from 6,711 yards from the Champ tees down to 4,132 from the Calusa tees, and the signature 12th, “Oasis,” is an island-green par 3 that Golf Digest included among golf’s best island greens. The clubhouse, about 34,000 square feet before the latest work, went through a $16 million renovation funded by Stock with no member assessment, per the Business Observer report on the first phase of the renovation: Phase I reopened in early March 2026 and the outdoor Greenside Grille and bar followed in late April 2026. The club’s tennis and racquets page lists four clay tennis courts with stadium seating and two pickleball courts, and its fitness page describes a 4,000 square foot center open seven days. For how Olde Cypress compares with other Naples clubs, see our guide to Naples golf communities.

The Homes

Olde Cypress is almost entirely detached single-family homes; the one attached product is Santorini Villas, where Collier County’s building footprints show 55 homes in paired villa buildings on Santorini Court. The nine neighborhoods on the master association’s site map are the Olde Cypress HOA (Units One, Two and Three, 185 homes on Olde Cypress Drive, Treeline Drive, Wild Orchid Court and Lone Pine Lane), Egret Cove (18 on Olde Cove Way), Biscayne Place (8 at the entrance corner), Santa Rosa (27 on Monteverde Way), Santorini (55), Strada Bella (18), Terramar (55), Da Vinci Estates (60) and Lantana (122). No vacant residential lots remain on the 2026 roll, so every purchase is a resale or a rebuild.

The build eras are distinct. County building footprints show the original Olde Cypress neighborhoods mostly completed between 2000 and 2006, Biscayne Place and Strada Bella from 2004 to 2007, Da Vinci Estates from about 2003 to 2009, and Lantana, the newest, built out from 2013 to 2016. Lot size follows price. Da Vinci Estates has the largest lots (a median of about 18,263 square feet), followed by Biscayne Place (about 16,680), Units One and Two (about 13,000 to 14,000) and Strada Bella (about 12,800); Terramar, Lantana, Santa Rosa, Lone Pine and Egret Cove cluster around 9,600 to 10,500 square feet, and Santorini lots run about 6,600.

Views are the other sorting line. Measured against the golf, lake and preserve parcels on the county roll, 60 of 61 homes in Unit One, all 55 in Terramar, all 27 in Santa Rosa, all 18 in Egret Cove and all 8 in Biscayne Place touch the golf course parcel. Lone Pine splits between golf and the big master preserve. Lantana is mostly lake-oriented, and Da Vinci Estates mixes golf, lake and preserve around a central lake inside the Mona Lisa Boulevard loop. The master association sums it up on its About page: nearly every homesite has a golf course or lake view.

The Rules That Matter Day to Day

Olde Cypress runs on two layers of rules: the master Declaration, which applies everywhere, and each neighborhood’s own declaration, which can add more. Architectural changes need two approvals, first the neighborhood’s committee and then the master’s. These are the master-level rules buyers ask about most, all from the 2019 Amended and Restated Declaration for Olde Cypress unless noted.

• Leasing. Written leases only, of the whole home, with no lease shorter than 60 days, no more than four leasehold interests per home per calendar year, and no subleasing (section 9.13). Each lease needs a Board application with a credit and background check, a $100 application fee and a $1,000 refundable Common Area deposit, and the Board must act within 5 business days. The 60-day floor dates from the 2013 leasing amendment for Olde Cypress, which raised it from 30 days. Timeshares and home swaps count as leases, and a neighborhood can be stricter.
• Pets. Common household pets such as dogs, cats and birds are allowed; they must be leashed outdoors and may not be left unattended or tethered on porches, lanais, common areas or in garages (section 9.18). Livestock, poultry and reptiles are prohibited, and the Board can require removal of a nuisance pet. Dog runs, animal pens and fences need approval.
• Golf carts on the streets. Golf carts may be driven on the community’s streets subject to master association rules, while course carts stay on the course and the designated cart paths (section 9.31). With about 60% of golf members using their own carts, this is how many owners get to the tee.
• No swimming in the lakes. The lakes are for looking at. “Swimming or wading is not allowed,” and no boats are permitted except for maintenance (section 9.11). Lake water may not be pumped for irrigation or household use without approval, and a 20-foot lake maintenance easement runs landward from the top of the bank. The master association publishes its Olde Cypress lake management plan for the 13 lakes in its system.
• Parking. No vehicle may be parked on Olde Cypress streets overnight; vehicles are to be garaged overnight, with no more than two cars in a driveway.
• For Sale signs and open houses. Only one standardized sign is allowed: a green wooden For Sale sign, 2 feet by 1.5 feet, in Benjamin Moore Glow Essex Green or Sherwin Williams 6194 with cream lettering, per the master association’s information page for real estate agents. Public open houses run Saturday and Sunday from noon to 5 p.m., broker opens run Monday to Friday, and open-house signs come from the guard house against a $20 refundable deposit.
• Fees. Owners receive a quarterly invoice from their neighborhood association that includes the neighborhood’s costs and the owner’s share of the master association; the master association’s About page says that fee covers common grounds (landscaping, streetlights, signage, paving, stormwater) and basic exterior landscaping of each home. The dollar amounts are not published publicly; the estoppel certificate states them at contract.

Nature and the Preserve Holes

For a community this close to I-75, Olde Cypress holds a lot of wild land. Ordinance 2000-37 set aside a 176.2-acre wetland preserve, park and wildlife sanctuary, and the master association’s largest parcel on the 2026 roll is a 158.59-acre preserve tract on the east side, between Lone Pine Lane and Treeline Drive. Conservation lands and buffer zones may not be altered except to remove exotic plants, under section 11.04 of the Declaration. The club says holes 13 and 14 are “two of the Club’s three preserve holes with no homes around them,” and its post on the wild side of Olde Cypress lists bobcat, white-tailed deer, river otter, fox squirrel and screech owls, plus purple martin houses and an annual daybreak birding tour. The club also states that the course is certified in the Audubon International Cooperative Sanctuary Program for Golf.

Just outside the community’s south edge, off Immokalee Road, Conservation Collier’s Alligator Flag Preserve at 7875 Immokalee Road carries public dirt hiking trails and has no parking lot, so it is a walk or a bike ride, not a drive. Our guide to Conservation Collier preserves covers the larger ones nearby.

The Honest Trade-Offs

Olde Cypress has real strengths and a few things every buyer should weigh before writing an offer.

• The club cost is not published. Social membership is mandatory and golf is extra, but neither the dues nor the initiation appears on the club’s public site. You will not know your all-in annual cost until you have the club’s current figures and the neighborhood association’s estoppel in hand.
• Neighborhood fees are behind a resident login. The quarterly neighborhood and master assessments are not posted publicly, and the master’s working capital contribution at closing is set by the Board, not printed in the Declaration.
• The flood map is changing. On FEMA’s effective maps, dated May 16, 2012, much of the Olde Cypress PUD is mapped in Zone AH, a Special Flood Hazard Area, with Letters of Map Amendment removing individual homes that surveyed above the base flood elevation; Lantana as a whole was removed to Zone X by FEMA LOMR-F 13-04-6118A in 2013, even though the map graphic still paints it Zone AH. The preliminary map issued March 2025 places the Olde Cypress PUD homes in Zone X, but it is not effective yet: Collier County’s announcement on the proposed flood insurance rate map says the appeal period opened August 19, 2026, with the new map targeted for summer 2027. A LOMA or LOMR-F is address-specific, and lenders decide flood insurance per building.
• Immokalee Road traffic. The Immokalee Road segment between Logan and Collier Boulevards that fronts the community runs at 103.4% of peak-hour capacity, level of service F, in Collier County’s 2025 Annual Update and Inventory Report. The Logan Boulevard gate helps, but season-time trips west still feel it.
• Older homes in the original neighborhoods. County building-footprint layers show 155 of the 366 homes in the Olde Cypress PUD already standing by 2002, so most of them were likely permitted before the Florida Building Code took effect in March 2002, and roof age, window and door protection and wind mitigation deserve a close look at inspection.
• Lakes are scenery, not recreation. No swimming, no wading and no boats. If you want water access, this is not that community.

Who Tends to Be Happiest in Olde Cypress

Olde Cypress suits buyers whose wish list reads like this: a detached home on a golf or lake view, a gate with one controlled entrance, a club they want to use at least socially, and an easy run to I-75 without living on a busy road. It suits golfers who want a P.B. Dye course with the option of Associate Golf rather than a bundled full membership, and tennis and pickleball players who want clay courts under the same membership they are required to carry anyway. Buyers who want newer construction within the same gate tend to look first at Lantana, built from 2013 to 2016; buyers who want the largest lots look at Da Vinci Estates and Biscayne Place; buyers who want the lowest entry price in the gate look at Santorini Villas and Lone Pine Lane.

It suits less well a buyer who wants no club obligation at all, short-term rentals, or a pool and park run by the homeowners’ association rather than the club. If you are weighing Olde Cypress against its neighbors, our guides to Longshore Lake, Heritage Bay and The Vineyards lay out the same facts for each.

Thinking about selling your Olde Cypress home? Start with a free valuation of your Olde Cypress home, or Call Jesse direct at (239) 898-6072 for a confidential conversation about pricing against every recorded sale in your neighborhood.

Buying in Olde Cypress? Call Marc at (239) 287-5873 and he will walk you through the club terms, the lease rules and the flood picture for the street you like before you tour, or read how we represent buyers in Southwest Florida.

Olde Cypress Real Estate Market Snapshot

Olde Cypress homes sold at a median of $1,105,000 across 26 closings in the 12 months to September 26, 2026, at a median 29 days on market and 97.52% of list price, per the Southwest Florida MLS Matrix. County recorded sales show the Olde Cypress median rising from $670,000 in 2016 to a $1,550,000 peak in 2023, then easing.

Data updated: September 2026

This section uses two different records, and we keep them apart. The Southwest Florida MLS Matrix, pulled September 26, 2026, gives the current market: closings, days on market, sold-to-list, price per square foot of living area and the homes for sale today. The Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) gives the long history and the neighborhood detail; it covers the 548 single-family homes, counts only sales the county flags as arm’s-length, and its latest recorded sale is May 22, 2026 because deeds lag. The two records cover different windows and different sales, so their counts and medians will not match exactly, and we never mix them in one figure. Assessed values from the county roll appear at the end, and they are values set for taxation, not prices.

The MLS Trailing 12 Months

Source: Southwest Florida MLS Matrix, pulled September 26, 2026.

With 26 sales, an even count, the median is the mean of the two middle sales, $1,100,000 and $1,110,000. A median of 29 days on market and 97.52% of list says well-priced Olde Cypress homes are selling in about a month for close to their asking price, and 6 of the 26 closed at or above their final list price. The tables that follow break the same pull down by neighborhood, list every closing, show what is for sale today and set this year against the one before it.

MLS Closings by Neighborhood, Trailing 12 Months

Source: Southwest Florida MLS Matrix, pulled September 26, 2026, closings from September 27, 2025 to September 26, 2026. Each sale is assigned to its neighborhood by street, so homes on Olde Cypress Drive and Treeline Drive (Units One and Two and Biscayne Place) are grouped together.

Every neighborhood here is a small sample for one year, so read these rows as the sales that happened, not as neighborhood price levels. Lantana carried the year, with 8 of the 26 closings and the quickest pace, a median 9 days. Santorini Villas took the longest, a median 75 days on four sales.

MLS Closings by Neighborhood, 48 Months

Source: Southwest Florida MLS Matrix, pulled September 26, 2026, closings from September 27, 2022 to September 26, 2026.

Four years of MLS closings show the neighborhood order more clearly than any single year: Da Vinci Estates at a $2,150,000 median on 17 sales and Santorini Villas at $645,000 on 13, inside the same gate. Across all 107 closings the median was $1,400,000, at a median $489.39 per square foot of living area, 96.19% of list and 27 days on market (n = 102 sales with a marketing period).

Every MLS Closing in the Last 12 Months

Source: Southwest Florida MLS Matrix, pulled September 26, 2026 (26 closings, October 8, 2025 to August 21, 2026). “Entered after closing” marks a sale added to the MLS after it closed, with no marketing period and so no days on market.

Six of the 26 closed at or above their final list price, including the fastest sale, a Lantana home at its full $1,735,000 list price after 0 days on market, and an August 2026 Lantana sale at $1,350,000 against a $1,340,000 list price. The slowest was a Lone Pine Lane home at 293 days. January through May 2026 held 17 of the 26 closings, the in-season pattern Naples sellers plan around.

Olde Cypress Homes for Sale Now

Source: Southwest Florida MLS Matrix, pulled September 26, 2026.

Five active listings against 26 closings a year, about 2.2 a month, is about 2.3 months of supply, and five listings are under 1% of the 548 homes behind the gate. The median active list price is $1,669,900 (n = 5, the observed middle listing), above the $1,105,000 median sale because today’s listings lean to Da Vinci Estates and Terramar; a list price is an ask, not a sale. Three of the five active listings have been on the market 93 to 283 days, which is what a 29-day median hides: a home priced above its neighborhood’s recent sales waits.

Year Over Year: The Last 12 Months Against the 12 Before

Source: Southwest Florida MLS Matrix, pulled September 26, 2026.

The latest year had fewer and lower-priced closings, but sellers got closer to their list price (97.52% against 93.54%) and sold faster (29 days against 37). Do not read the $320,000 drop in the median as a 22% fall in home values. The mix moved: the latest 12 months include six Lone Pine Lane sales and four Santorini villa sales, the two lowest-priced neighborhoods, and only one Da Vinci Estates sale. The median price per square foot, which adjusts for size though not for neighborhood, fell by a smaller amount, about 5%, from $499.30 to $472.75.

MLS Calendar-Year Medians, 2023 to 2026

Source: Southwest Florida MLS Matrix, pulled September 26, 2026.

These MLS medians and the county recorded medians below are two different records, and they do not match. The MLS counts closings reported to it through September 26, 2026; the county file counts recorded qualified sales and ends at the May 22, 2026 recording. For 2023, for example, the MLS median is $1,490,000 on 36 closings and the county median is $1,550,000 on 29 recorded sales. Both records point the same way: a 2023 peak, a softer 2024 and 2025, and a lower 2026 so far, partly because of which neighborhoods sold.

County Recorded Sales by Window

Source: Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026.

The longer the window, the higher the median, which tells you the most recent year has sold for less than the years just before it. Part of that is price and part is mix: the last 12 months include six sales on Lone Pine Lane and three in Santorini Villas, the two lowest-priced neighborhoods, and only one in Da Vinci Estates.

Calendar-Year Median Recorded Sale, 2016 to 2026

Source: Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026. Each year is a small group of sales; 2024 and 2026 are small samples.

In plain English: from 2016 through 2020 the Olde Cypress median barely moved, staying between $670,000 and $760,000. It then jumped to $990,000 in 2021, $1,347,500 in 2022 and a peak of $1,550,000 in 2023, about 2.3 times the 2016 figure. Since then it has come off that peak: $1,322,500 in 2024, $1,367,500 in 2025 and $1,110,000 for the 17 sales recorded in 2026 through May 22, about 28% below the 2023 peak and still about 66% above 2016. The 2026 county median of $1,110,000 happens to equal the MLS median for 2026 through September 26; they are different records covering different sales (the county file ends at the May 22, 2026 recording), and the match is a coincidence of the numbers, not a single figure. Because each year holds only 17 to 47 sales and the neighborhoods range from about $600,000 villas to $3 million estates, a year’s median moves with which neighborhoods sold. Read the trend, not any single year.

Recorded Sales by Neighborhood, 36 Months

Source: Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026. Total: 72 sales. Samples under 10 are small; a single sale is listed, never turned into a median.

The spread is the story. Over three years, a Da Vinci Estates home recorded at a median of $2,387,500 while a Santorini villa recorded at $640,000, inside the same gate and under the same club requirement. An Olde Cypress-wide median describes almost no actual home, which is why a price opinion here has to start from the neighborhood, then the view (golf, lake or preserve), then the lot.

Every Recorded Qualified Sale in the Last 12 Months

Source: Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026 (24 sales, September 16, 2025 to May 22, 2026, the latest recorded in the file).

Twenty-four sales, with a median of $1,142,500 (the mean of the middle pair). By neighborhood that is six in Lantana, six on Lone Pine Lane, four in Terramar, three in Santorini Villas, two each in Santa Rosa and Unit Two, and one in Da Vinci Estates. Lantana alone ran from $841,000 to $1,795,000, a reminder that lot, view and condition move price as much as the neighborhood name. The 11 sales recorded from January through March 2026 are nearly half of the 24, which fits the Naples pattern of in-season closings.

The 2026 Preliminary County Roll: 548 Homes

The Collier County Property Appraiser 2026 preliminary roll lists 548 single-family homes behind the Olde Cypress gate: 366 inside the Olde Cypress PUD, 60 in Da Vinci Estates and 122 in Lantana. For the 366 PUD homes, the median 2026 preliminary just value is about $1,022,443 and the median 2026 preliminary total tax is about $7,018 (n = 366). About seven in ten homes inside the Olde Cypress PUD, 252 of 366, carry a Florida homestead exemption on the 2026 preliminary roll.

Source: Collier County Property Appraiser 2026 preliminary roll. Just values are assessed values set for taxation, not prices. The roll is preliminary; final 2026 values and bills issue in November 2026.

Two cautions. First, a just value is not a price, and it lags the market; the recorded and MLS medians above are the prices. Second, the tax on any one home depends on its homestead status and its Save Our Homes cap, so a buyer’s first-year bill is usually higher than the seller’s. The 2025 millage rate for these parcels was 9.5058 mills, with no CDD levy.

What the Numbers Mean for Sellers and Buyers

For sellers: the MLS says the market is moving, with a median of 29 days on market and 97.52% of list, but the county record says the 2023 peak is behind us and 2026 has recorded at a lower median than 2024 or 2025. Pricing off a neighbor’s 2023 sale will leave a home on the market. Pricing off the right comparables, meaning the same neighborhood, the same view and the last 12 months, is how Olde Cypress homes sell in about a month. The mandatory club membership and the green-sign rule mean your marketing has to reach the buyer who already wants this club and this gate.

For buyers: the neighborhood you choose sets your price range more than anything else, from about $640,000 for a Santorini villa to more than $2 million in Da Vinci Estates, based on three years of recorded sales. A median 97.52% sold-to-list leaves limited room below asking on well-priced homes. Budget beyond the price for the club social dues, the quarterly neighborhood invoice, the master working capital contribution at closing and flood insurance per the lender’s building determination, and get the club’s current figures and the estoppel before your inspection period ends.

Selling or Buying in Olde Cypress? Start With the Numbers for Your Street

The recorded median price in Olde Cypress ranges from $640,000 in Santorini Villas to $2,387,500 in Da Vinci Estates over the last 36 months, so a community-wide number will not price your home or your offer. Selling? Get a free valuation of your Olde Cypress home, or Call Jesse direct at (239) 898-6072 and he will price your home against every recorded sale on your street. Buying? Call Marc at (239) 287-5873 before you make an offer, or read how we represent buyers in Southwest Florida.

How Did Olde Cypress Begin? The Woodlands Land, the Stock Family and the PUD

Olde Cypress began as the Woodlands PUD and DRI, approved by Collier County in 1986. Ordinance 99-27 renamed the land Olde Cypress on April 27, 1999, the same day the master declaration was recorded. Ordinance 2000-37 set today’s 538.1-acre plan, and a Stock family partnership has owned the golf course land since 1998.

The Land Before Olde Cypress: The Woodlands PUD and DRI

Before anyone called it Olde Cypress, this land north of Immokalee Road was the Woodlands. Collier County approved the Woodlands PUD by Ordinance 86-75, together with the Woodlands Development of Regional Impact under Development Order 86-1, and amended the PUD by Ordinance 96-64 after environmental permitting. The county’s List of Collier County PUD Ordinances (LDC Appendix F) carries that chain on one line, and the county’s own PUD layer still labels the Olde Cypress PUD “AKA Woodlands.”

The 1996 revision matters to anyone who walks the preserve today. According to the history recited in the Board of County Commissioners’ April 26, 2011 agenda packet for the Olde Cypress PUD amendment, Ordinance 96-64 replaced the eastern park, jogging trail and bicycle trail shown on the older master plan with wetland preserve. That decision is why the eastern half of Olde Cypress is a large wooded preserve rather than a public park.

April 27, 1999: The Rename and the Master Declaration on the Same Day

Two things happened on April 27, 1999. The Board of County Commissioners adopted Ordinance 99-27, which renamed the Woodlands PUD as Olde Cypress, and the Declaration of Covenants, Conditions, Restrictions and Easements for Olde Cypress was recorded in the Collier County Official Records at OR 2539 PG 2902. Every Olde Cypress neighborhood declaration recorded since then points back to that book and page.

Ordinance 99-27 did not last long. The county replaced it with Ordinance 99-92 on December 14, 1999, alongside Development Order 99-5, a DRI Notice of Change that added 28.68 acres on the east edge of the property without adding any homes. Six months later the county replaced 99-92 as well.

Ordinance 2000-37: The Plan Olde Cypress Was Built On

The base zoning document for Olde Cypress today is Ordinance 2000-37, adopted May 23, 2000, which repealed 99-92. A certified copy is reproduced in the 2011 Board agenda packet. The petition was prepared by the engineering and planning firm Hole Montes and Associates for the development company, and the numbers it approved are the numbers the community still reflects:

The ordinance allowed 1,100 dwelling units (a gross density of about 2.1 units per acre), 12.5 acres and 165,000 square feet of commercial space, and an 18-hole golf course with clubhouse and tennis. It located the land on the north side of Immokalee Road (County Road 846), about 1.3 miles east of I-75, immediately east of the Longshore Lakes PUD and about one mile west of County Road 951, in Sections 21 and 22, Township 48 South, Range 26 East. If you know Longshore Lake, Olde Cypress is its eastern neighbor.

The findings in 2000-37 also record three details buyers rarely hear: a 2.1-acre preserve protects archaeological artifacts on the site; 9.3 acres were added for a golf driving range; and personal self-storage was allowed in the commercial tract, with six acres of storage forfeiting 79,200 square feet of retail. The county estimated build-out at 17 to 20 years.

Ordinance 00-53: The Amendment the County Map Shows

On September 12, 2000 the county amended the PUD again by Ordinance 00-53 (petition PUD-99-18(1)). That is the ordinance number the county’s GIS layer and the Collier County PUD Master List dated June 11, 2026 show against the Olde Cypress PUD, with an approval date of 09/12/00 and a status of “BUILT OUT.” The full text of 00-53 was not among the documents we read, so we describe it only as the amendment of record.

Ordinance 2011-14: 1,100 Homes Became 942, and 158 Moved to Lantana

The most important zoning change after 2000 came on April 26, 2011, when the Board voted 5 to 0 to adopt Ordinance 2011-14. It cut the Olde Cypress PUD’s cap from 1,100 to 942 dwelling units (about 1.75 units per acre) and deleted the old requirement for a 3.9-acre park and nature trail. The county staff report explained the purpose in one sentence: “The removal of the 158 dwelling units from the Olde Cypress PUD will allow the proposed 158 unit HD Development RPUD … to be added to the Olde Cypress DRI.”

Those 158 units went to the adjoining H.D. Development PUD, also known as Vita Tuscana, by Ordinance 2011-13 the same day. That land is the Lantana neighborhood. Resolution 2011-83 (Development Order 2011-01) grew the DRI boundary by 63.9 acres to about 602 acres while holding total DRI units at 1,100. The votes are recorded in the Board’s April 26, 2011 meeting recap.

About 100 people attended the neighborhood information meeting for that amendment, and the transcript in the packet shows residents were split on removing the park. The county’s PUD Master List still prints 1,100 units against the Olde Cypress PUD; that figure is the DRI total for Olde Cypress plus Lantana, and the current cap for the Olde Cypress PUD itself is 942.

Who Developed Olde Cypress: The Stock Family Partnership Since 1998

The land and the golf course have had one continuous owner since 1998. The Certificate of Limited Partnership filed with the Florida Division of Corporations formed Olde Cypress Development, Ltd. on September 2, 1998. Its original general partner was Olde Cypress Development Corporation, formed in September 1997. Its sole limited partner, a member of the Stock family, committed up to $10,000,000 of capital.

The club began in a sister partnership, The Club at Olde Cypress, Ltd., which merged into Olde Cypress Development, Ltd. on May 30, 2001. On February 20, 2003, a Certificate of Amendment made Stock Development, LLC the general partner. Stock Development, led by CEO Brian Stock, has run the property from that point forward.

The 2025 Rename and the July 24, 2026 Conversion

Two recent filings changed names, not owners. On December 22, 2025 Stock Development, LLC renamed itself SD Amenity Holdings, LLC, a change recited in the 2026 Certificate of Amendment to the partnership. Then on July 24, 2026 the partnership converted into Olde Cypress Development, LLC, with a principal office in Naples 34119.

The 2026 preliminary Collier County roll still shows the golf parcels titled to “Olde Cypress Development Ltd,” because the roll has not caught up with the July conversion. The club’s About Us page describes the club as “non-equity, privately owned” by Stock Hospitality, the Stock operating division. No sale of the club to members, and no outside sale of any kind, appears in the corporate record.

The Golf Course: Built in 1999, the First P.B. Dye Design in Collier County

The course came first. Golfweek’s September 29, 2021 report on the Olde Cypress renovation says the course was “Built in 1999” and was the first P.B. Dye design in Collier County, part of a 540-acre development. The same story covers the multimillion-dollar renovation that resurfaced all 18 greens with TifEagle Bermuda, refreshed 98 bunkers and installed new drainage before the course reopened in November 2021.

The clubhouse followed its own path. Construction on a clubhouse renovation began in March 2025, funded by Stock Development with no assessment to the members. The Business Observer sized the project at $16 million. Phase one reopened in early March 2026, per Club + Resort Business on March 3, 2026, and the Greenside Grille and outdoor bar opened in late April 2026. For how the course compares with the rest of the market, see our guide to Naples golf communities.

The First Neighborhood Declarations: 2000 to 2004

With the master declaration in place, neighborhood declarations followed, each subjecting its lots to OR 2539 PG 2902. The recorded declarants and dates we could read are these:

The recorded documents we read do not name the homebuilders for Units One, Two and Three, Egret Cove, Santa Rosa or Santorini Villas, and we do not guess at them. The master association simply calls Olde Cypress “established in 2000” on its About page, which fits the record: land partnership in 1998, master declaration and golf course in 1999, first neighborhood declarations in 2000.

Da Vinci Estates and Lantana: Separate PUDs, Same Gate

Two Olde Cypress neighborhoods sit on land zoned outside the Olde Cypress PUD. Da Vinci Estates has its own PUD, approved by Ordinance 01-36 on June 26, 2001 (repealing Ordinance 00-11). Lantana sits in the H.D. Development PUD, also known as Vita Tuscana, first zoned by Ordinance 03-30, replaced by Ordinance 05-65 on November 15, 2005, and enlarged to 158 units by Ordinance 2011-13. Both declarations subject their lots to the Olde Cypress master declaration and make each owner a member of the master association, so both are Olde Cypress in every way a buyer experiences it: one gate, one master association, one club.

When Each Neighborhood Was Built

Collier County’s building footprint layers, published for 2000, 2002, 2004 and later years, show when a structure first appears on each lot. That brackets construction to a two-year window rather than giving an exact year built, so read the table as eras.

Build era matters at resale for roofs, windows and insurance. Roughly 155 of the 366 homes inside the Olde Cypress PUD already appear in the 2000 or 2002 footprint layers, which places them before or at the start of the Florida Building Code’s March 1, 2002 effective date. Lantana, built 2013 to 2016, is the one neighborhood that is entirely a modern code-era build.

Olde Cypress History at a Glance: A Dated Timeline

Owners who know this history price better. A Lone Pine Ln home from 2002 and a Lantana home from 2015 carry different roofs, windows, flood-map histories and insurance quotes, and the right comparables follow the build era as much as the street. If you own in Olde Cypress, Call Jesse direct at (239) 898-6072 or request a free valuation of your Olde Cypress home priced against the recorded sales in your own neighborhood. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.

What Is Inside the Olde Cypress PUD, and What Is Not Olde Cypress?

The Olde Cypress PUD covers 538.1 acres, but not everything inside it is the gated community. The PUD also holds the Preserve Commons shopping tract, the Amberton apartments and the separate Fairway Preserve condominium, while two Olde Cypress neighborhoods, Da Vinci Estates and Lantana, sit in their own PUDs. One gate on Treeline Drive defines the community.

The Master Plan in Numbers

The master association describes Olde Cypress as “550 single-family estate homes and attached villa residences” on about 540 acres on its About page. The 2026 preliminary Collier County roll counts 548 single-family homes across the nine neighborhoods, which the master association rounds to 550. The zoning figures come from Ordinance 2000-37 and the county’s PUD Master List dated June 11, 2026:

• 538.1 acres in the Olde Cypress PUD as approved by Ordinance 2000-37 (the association’s rounded figure is about 540 acres)
• 176.2 acres of wetland preserve, park and wildlife sanctuary, which also satisfies the county’s 25 percent native vegetation rule
• About 168 acres of golf course: the three club parcels on the 2026 roll total 167.99 acres, and the county’s master list carries 168.30 golf acres and 18 holes
• 13 lakes in the master association’s system, per its Lake Management document; Lantana and Da Vinci Estates have their own ponds
• 942 dwelling units as the current cap under Ordinance 2011-14
• 12.5 acres and 165,000 square feet of commercial space

The 158.59-Acre Master Association Parcel

The single largest piece of land the owners control is not a golf hole. The 2026 preliminary roll shows the Olde Cypress Master Property Owners Association holding a 158.59-acre tract classified as preserve and wetland, plus a 15.66-acre tract, the master road tracts (including 7200 Treeline Dr at 9.37 acres), a lake tract off Logan Blvd N and several small common tracts. The master association’s own site map shows that preserve as the large wooded area in the eastern half of the community, between Lone Pine Ln and Treeline Dr. Under Section 11.04 of the 2019 Amended and Restated Declaration for Olde Cypress, conservation lands and buffer zones may not be altered except to remove exotic plants.

The Golf Course Is Private Land, Not Common Area

The golf and club parcels belong to Olde Cypress Development: 7165 Treeline Dr (154.86 acres, the course and clubhouse), 2414 Logan Blvd N (9.23 acres, the driving range added in 2000) and 7150 Treeline Dr (3.9 acres). Section 14.01 of the restated declaration says “The Country Club Property is not a part of the Property,” and the declaration states that the course and club are not Common Areas, being owned and operated by a separate entity. Homes along the fairways carry golf-play easements, which is normal in a course community and worth reading before you buy a lot on a landing zone.

The Commercial Tract: Preserve Commons on Preserve Ln

The 12.5 commercial acres approved in 2000 are the Preserve Commons tract on Preserve Ln, fronting Immokalee Road. The 2026 roll shows a shopping center, a service station and self storage there, which matches the ordinance: self storage was limited to the west side of the commercial entrance, behind the Immokalee frontage. Preserve Commons is inside the Olde Cypress PUD but outside the Olde Cypress gate, and it is not part of the master association. It is public retail that anyone can drive into from Immokalee Road.

The Amberton Apartments on Dream Catcher Circle

A 28.48-acre apartment parcel at 8067 Dream Catcher Cir is also inside the Olde Cypress PUD. A county unit summary dated March 15, 2010, printed in the 2011 Board packet, allocated 312 multifamily units to Amberton, of which 132 were built at the time. The apartments share access with Fairway Preserve off Immokalee Road through Dancing Wind Ln. They are not behind the Olde Cypress gate and are not in the master association.

Fairway Preserve at Olde Cypress: A Separate Condominium Outside the Gate

Fairway Preserve at Olde Cypress is the name that causes the most confusion. It is a 264-unit, three-story condominium on Preserve Cir, inside the Olde Cypress PUD and carrying the Olde Cypress name, but it is not part of the gated community or the master association:

• It does not appear on the master association’s neighborhood site map, and it is not one of the nine neighborhood associations.
• Its street, Preserve Cir, connects only to Dancing Wind Ln and from there to Immokalee Road. It has its own tele-entry gate, as its own association’s website describes.
• It has its own recorded Declaration of Condominium of Fairway Preserve at Olde Cypress, recorded August 12, 2005 at OR 3866 PG 4006, made by a separate apartment developer. The buildings were built as apartments about 2001 to 2002 and converted to condominium in 2005.
• It has its own amenities (pool, spa, fitness room and more), its own association, and its own school zoning: Fairway Preserve is zoned to Gulf Coast High, while the single-family streets behind the Olde Cypress gate are zoned to Aubrey Rogers High for 2026 to 2027.

Fairway Preserve owners do not receive Olde Cypress club social membership through the master declaration, because they are not under it. A listing that says “Olde Cypress” and shows a Preserve Cir address is a Fairway Preserve condominium, not a home inside the gate.

Da Vinci Estates PUD and the H.D. Development (Vita Tuscana) PUD

Two neighborhoods that are fully part of Olde Cypress sit outside the Olde Cypress PUD boundary. The county’s PUD Master List carries them this way:

• Da Vinci Estates PUD (Ordinance 01-36): 40.37 acres, 61 single-family homes approved, 8.20 conservation acres, status closed out. The 2026 roll shows 60 homes on Mona Lisa Blvd, Leonardo Ave, Florentine Ct and Renaissance Ct.
• H.D. Development PUD, also known as Vita Tuscana (Ordinance 05-65, enlarged by 2011-13): 46.64 acres on the master list, 125 single-family homes authorized, 122 built, 34.80 conservation acres. This is Lantana, on Lantana Cir and Lantana Way. The 2011 staff report tabulated the enlarged Vita Tuscana PUD at 65.3 acres; the two county records measure it differently, and we give both.

Leonardo Ave connects only to Olde Cypress Dr, and Lantana Cir connects only to Treeline Dr, both inside the gate, per the county’s road centerline network. If you see “Vita Tuscana” on an older record, it refers to the Lantana land.

One Entrance: Treeline Drive at Logan Boulevard North

Olde Cypress has one road entrance: Treeline Dr off Logan Blvd N, about a quarter mile north of Immokalee Road. Neither Treeline Dr nor Olde Cypress Dr touches Immokalee Road, and there is no Olde Cypress Blvd entrance. The club’s directions page gives the approach from I-75 Exit 111: east on Immokalee Road about a mile and a quarter to Logan Blvd, then north.

Section 3.05 of the restated declaration splits the roads into public and private. Logan Blvd N from Immokalee Road to the community entrance, and Treeline Dr from Logan Blvd to “the traffic control gate,” are dedicated to the public. The rest of Treeline Dr is dedicated to the master association, and the other streets are owned or maintained by the master association or the neighborhood association.

Why the Club Sits Outside the Gate

The 548 homes sit behind one staffed gatehouse on Treeline Dr, with a resident lane and a guest lane, per the master association’s community access notice. The clubhouse, tennis and pickleball courts, pool and practice range sit west of that gate, on the public stretch of Treeline Dr. That is why the club’s About Us page says the club “is conveniently located outside the community’s gates” while the club’s real estate page calls Olde Cypress a gated community. Both are true: non-resident members reach the club without passing the gate, and residents pass the club on the way home.

Alligator Flag Preserve Next Door

On the community’s south edge, near Immokalee Road, sits Alligator Flag Preserve, a Conservation Collier preserve at 7875 Immokalee Rd. The county’s trails layer maps about half a mile of public dirt hiking trail there, and it has no parking lot; Greater Naples Leadership describes pine-carpeted paths reachable on foot or by bike along the Immokalee Road sidewalk near Preserve Ln. County records give different acreages for it, so we do not quote one. It is public land, not Olde Cypress common area. More county preserves are in our guide to Conservation Collier preserves.

What the Name Covers

Knowing exactly which side of those lines a home sits on is the first thing a buyer should settle, and the first thing a seller’s marketing should get right. If you own behind the gate, Call Jesse direct at (239) 898-6072 for a free valuation of your Olde Cypress home. If you are comparing Olde Cypress with its neighbors, Call Marc at (239) 287-5873 and see how we represent buyers in Southwest Florida, or start with our Naples guide.

Who Governs Olde Cypress? The Master Association and Nine Neighborhoods

Olde Cypress is governed by the Olde Cypress Master Property Owners Association and nine neighborhood homeowners associations, managed by Alliant Property Management. Each owner pays one quarterly invoice from the neighborhood association that includes the master share. The Club at Olde Cypress is privately owned: owners hold a mandatory social membership but no equity or vote in the club.

Data updated: September 2026

The Master Property Owners Association

The Florida Division of Corporations record for Olde Cypress Master Property Owners Association, Inc. shows a Florida not-for-profit corporation filed November 16, 1998, status active, with Amended and Restated Articles filed November 20, 2019 and annual reports filed for 2024, 2025 and April 23, 2026. Its registered agent is in care of Alliant Property Management, LLC in Fort Myers.

The management company is Alliant Property Management, 13831 Vector Ave, Fort Myers, reachable at (239) 454-1101, Monday to Friday 9 to 4:30, per the master association website. The gatehouse number is (239) 592-5381.

The Nine Neighborhood Associations

The master association’s About page describes “nine Neighborhood Homeowners Associations (NHOA) and a Master Property Owners Association (MPOA),” and its site map color-codes the nine:

Each neighborhood is its own Florida corporation with its own declaration, budget and rules. Most are managed through Alliant; Da Vinci Estates and Santa Rosa use other management companies, according to their state filings. Neighborhood rules can be stricter than master rules, so a buyer needs both sets. Fairway Preserve is not one of the nine.

One Quarterly Invoice: What It Includes

The master association’s About page explains the billing: owners receive quarterly invoices from their neighborhood association that include the neighborhood costs plus the owner’s share of the master association. According to that page, the fee covers the common grounds (landscaping, streetlights, signage, paving and stormwater) and basic exterior landscaping of each home. That last item is why Olde Cypress yards look uniform: the association, not the owner, runs basic exterior landscaping.

Under Sections 8.03 and 8.04 of the 2019 Amended and Restated Declaration for Olde Cypress, the master assessment is allocated by “Value”: each lot counts 1.00, combined lots with one residence count 1.50, and assessments are paid quarterly in advance unless the Board decides otherwise.

How Owners Vote: Neighborhood Representatives as a Block

Owners do not vote individually at the master level. Each neighborhood association has a Neighborhood Representative, an officer of that association who casts all of the neighborhood’s master votes as a block. Under the restated declaration and bylaws, 51 percent of a neighborhood meeting can instruct how that vote is cast. In practice, if you want a say in master decisions, you work through your own neighborhood board.

Two-Step Architectural Review

Any exterior change goes through two architectural review committees: first the neighborhood association’s, then the master association’s, and both approvals are required (restated declaration Article X). The Board-promulgated architectural guidelines are posted only on the resident portal. Private tennis, basketball or similar courts on a lot need approval (Section 9.32), and fences, dog runs and animal pens are not permitted without approval, with walls and fences capped at six feet unless approved (Sections 9.09 and 9.25).

The 2019 Amended and Restated Declaration and Its Annexation Amendments

The master document in force is the Amended and Restated Declaration of Covenants, Conditions, Restrictions and Easements for Olde Cypress, adopted at a member meeting on November 18, 2019 and recorded November 27, 2019 as Instrument 5796524 at OR 5700 PG 1118 (71 pages, with restated Articles and Bylaws as exhibits). The master association hosts a certified copy of the 2019 restated documents.

Its Exhibit A lists the land it governs: the original declaration at OR 2539 PG 2902 (April 27, 1999) plus lands added by the Amendment at OR 2729 PG 1645, the Second Amendment at OR 2788 PG 2463, the Fifth Amendment at OR 3549 PG 1976 and the Sixth Amendment at OR 3631 PG 1445. Each of those can be pulled from the Collier Clerk’s Official Records search.

One drafting detail: the restated declaration recites the PUD as “Ordinance No. 96-94.” County records show the 1996 PUD ordinance as 96-64, and the current PUD as Ordinance 2000-37 as amended by 00-53 and 2011-14. We read the recital as a typographical error.

The Club Is Not Common Area, and Owners Hold No Equity or Vote

Article XIV of the restated declaration is the section every buyer should read. Section 14.02: “By acquisition of a Parcel, each Owner automatically becomes a social member of The Club at Olde Cypress,” with dues “as promulgated by The Club … from time to time.” Section 14.03: owners receive no equity, voting or ownership interest in the club property. Section 14.01: the club property “is not a part of the Property.”

The club confirms it from its side. Its membership page says social membership “is mandatory for all residents of the Olde Cypress community who do not hold a higher category of membership” and “is only available to those residing within the gates.” Full Golf and Associate Golf are optional upgrades, and as of September 2026 both are open to residents and non-residents. The club states it charges no member assessments and has no food and beverage minimum.

The Leasing Rules

Leasing is governed by Section 9.13 of the restated declaration, carried forward from the 2013 leasing amendment recorded at OR 4874 PG 3783, which raised the minimum from 30 days to 60:

• Minimum lease term: 60 days, in writing
• No more than four leasehold interests per parcel per calendar year
• The whole parcel only; no subleasing, no room rentals
• A timeshare arrangement or home swap counts as a lease
• Board application with credit and background check
• $100 application fee
• $1,000 refundable common area deposit against tenant damage to common areas
• The Board must act within 5 business days, or the application is deemed denied
• Neighborhood associations can add stricter rules

Four leases a year at a 60-day minimum makes seasonal rental workable; short-term vacation rental is not.

Pets

Section 9.18 allows common household pets such as dogs, cats and birds. Pets must be leashed outdoors and may not be left unattended or tethered on porches, lanais, common areas or in garages. The Board can remove a nuisance pet, and livestock, poultry and reptiles are prohibited.

Lakes and Conservation Buffers

The lake rules are strict. No boats on community lakes except for maintenance, and “Swimming or wading is not allowed” (Section 9.11). Lake water may not be pumped for irrigation or household use without architectural approval, and a 20-foot lake maintenance easement runs landward from the top of bank (Section 6.05). Conservation lands and conservation buffer zones may not be altered except to remove exotic vegetation (Section 11.04). A buyer eyeing a pool extension or landscaping on a lake or preserve lot should measure those easements before closing.

Parking and Golf Carts

The parking rule surprises many buyers: no vehicles of any kind may be parked on Olde Cypress streets overnight. Vehicles are to be garaged overnight, with no more than two cars in a driveway. Golf carts may run on community streets under master association rules, and course carts stay on the course and designated cart paths (Section 9.31).

Realtor, Open House and Sign Rules

The master association’s Realtors Information page sets how homes are shown and sold:

• Public open houses on Saturday and Sunday, noon to 5 p.m. only; broker opens Monday to Friday
• Outside open house hours, buyers must come with an agent or owner, or be phoned in to the guard house by a homeowner
• Open house signs come only from the guard house, against a $20 refundable deposit
• One standardized green wooden For Sale sign (2 feet by 1.5 feet, Benjamin Moore Glow Essex Green or Sherwin Williams 6194, cream lettering)

The restated declaration also disclaims any warranty of the guardhouse, gate or security service (Article XIII).

The Governing Documents Reading List

Before a contract’s inspection period ends, a buyer should have read:

1. The 2019 Amended and Restated Declaration, Articles and Bylaws (OR 5700 PG 1118)
2. The 2013 leasing amendment (OR 4874 PG 3783)
3. The neighborhood declaration: for example the 2016 restated Olde Cypress HOA declaration (OR 5260 PG 3502), the Santorini restated documents (OR 4911 PG 1167), the Santa Rosa 2011 restatement (OR 4722 PG 375), the Egret Cove amended documents, the Terramar declaration, the Strada Bella declaration, the Biscayne Place declaration, the Da Vinci Estates documents or the Lantana declaration
4. The master association’s Realtors Information page and community access notice
5. The master association’s Lake Management document
6. The club’s membership documents and current dues schedule, which come from the club, not the associations
7. The neighborhood association’s current budget and the estoppel certificate for the specific home

Sellers who hand buyers this package early close cleaner. If you are selling, Call Jesse direct at (239) 898-6072 and we will assemble your document package with a free valuation of your Olde Cypress home. Buyers, Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.

How Much Does It Cost to Live in Olde Cypress? The Fee Stack

Living in Olde Cypress means a quarterly neighborhood invoice that includes the master share, mandatory club social dues, optional golf membership, and property taxes at 9.5058 mills (2025). Olde Cypress has no CDD. The associations and the club do not publish their dollar amounts, so the real numbers come from the estoppel certificate and the club.

Data updated: September 2026

The Full Fee Stack at a Glance

Every layer an Olde Cypress owner can be billed, with its source. “Not published” means we could not find a public, first-party figure as of September 2026.

The Quarterly Neighborhood Invoice

Every Olde Cypress owner pays one bill: the neighborhood association’s quarterly invoice, which includes that neighborhood’s own costs and the owner’s share of the master association. The master association’s About page says that fee covers the common grounds (landscaping, streetlights, signage, paving and stormwater) and basic exterior landscaping of each home. The gatehouse, private roads and the 158.59-acre master preserve are master responsibilities funded the same way.

The dollar amount differs by neighborhood because each of the nine sets its own budget, and none of them publishes it outside the resident portal. That is the honest state of the public record in September 2026. Any “HOA fee” you see on a listing is a figure typed in by a listing agent, and it may be out of date or may omit the master share. The reliable figure is on the estoppel certificate for the specific home.

Club Social Membership: Mandatory, With Dues Set by the Club

Buying a home in Olde Cypress makes you a social member of The Club at Olde Cypress. That comes from Section 14.02 of the 2019 restated declaration, and the club’s membership page confirms it. Social membership covers the clubhouse, dining, the four clay tennis courts and two pickleball courts, the 4,000-square-foot fitness center and the pool, but not golf except as a golf member’s guest. For how those courts compare, see our Naples tennis and pickleball guide.

The club does not publish its social dues. Its fact sheet and membership guide sit behind request forms. The current number comes from the club’s membership office at (239) 596-4797.

Golf Membership: Optional, and Not Published by the Club

Golf is a separate purchase. The club offers Full Golf and Associate Golf (limited golf November to April, unlimited May to October), and as of September 2026 both are open to residents and non-residents. The club describes itself as non-equity, so a golf membership buys playing privileges, not an ownership share.

The club does not publish initiation fees or annual golf dues on its website; the fact sheet and golf guide are behind a form. Third-party figures circulating online conflict widely, from roughly $45,000 to $175,000 for golf initiation, and none of them is published by the club. We do not repeat them as prices. Get the current initiation and dues in writing from the club’s membership office at (239) 596-4797, and make them part of your purchase contract review.

The $1,950 Private Cart Fee

One club number is first-party. The club’s own Club Insider article on Naples private golf clubs says members may use their own golf carts on the course for an annual fee of $1,950, and that about 60 percent of members do. The club also states on its About Us page that it has no member assessments and no food and beverage minimum, and that the $16 million clubhouse renovation was funded by Stock Development with no assessment to members.

Leasing Fees

An owner who leases pays the master association a $100 application fee and a $1,000 refundable common area deposit for each lease, under Section 9.13 of the restated declaration and the 2013 leasing amendment. With a 60-day minimum and no more than four leases per calendar year, an owner leasing seasonally could pay the application fee up to four times a year. Neighborhood associations may add their own requirements.

Property Taxes: The 9.5058-Mill Rate

Every home in Olde Cypress, Da Vinci Estates and Lantana, and the Fairway Preserve condominiums, sits in the same Collier County millage area. The 2025 Collier County Tax Collector bill for a Lone Pine Ln home shows the total 2025 rate of 9.5058 mills broken down this way:

On that 2025 bill the ad valorem tax was $4,082.77, and the only non-ad valorem line was District 1 Garbage, $261.91. A mill is $1 of tax per $1,000 of taxable value, after exemptions and the Save Our Homes cap.

What Olde Cypress Homes Pay: 2026 Preliminary Taxes

The Collier County Property Appraiser 2026 preliminary roll shows these total taxes for the 366 single-family homes inside the Olde Cypress PUD (the roll’s tax field is not populated for Da Vinci Estates and Lantana in the data we pulled, so they are not in these figures):

About seven in ten of the homes inside the Olde Cypress PUD carry a Florida homestead exemption on the 2026 preliminary roll. The gap between the two medians is mostly the Save Our Homes cap: a long-held homestead is taxed on a capped assessed value, while a non-homestead home is taxed closer to its just value. A buyer does not inherit the seller’s cap. The year after you buy, the assessed value resets to the just value, so budget on the current just value times the millage, not on the seller’s bill.

By neighborhood, the same 2026 preliminary roll shows these median total taxes: Biscayne Place $15,120 (n = 8, small sample), Unit Two $10,252 (n = 69), Strada Bella $9,545 (n = 18), Unit One $8,438 (n = 61), Santa Rosa $7,692 (n = 27), Terramar $7,334 (n = 55), Lone Pine Ln (Unit Three) $5,754 (n = 55), Egret Cove $5,096 (n = 18) and Santorini Villas $4,720 (n = 55). These are preliminary figures; the certified 2026 bills issue in November 2026.

Garbage and Other Non-Ad Valorem Charges

The only non-ad valorem charge on the 2025 bill example was District 1 Garbage at $261.91. The 2026 preliminary roll does not yet carry non-ad valorem amounts anywhere in Collier County, so the 2026 garbage figure will appear on the November 2026 bills. There is no CDD line, no bond line and no special district levy on Olde Cypress bills.

Flood Insurance Context

Flood insurance is a separate cost that depends on the building, not the community. For context, the OpenFEMA NFIP policies dataset, as of September 8, 2026, shows a median single-family policy cost of $1,259 per year in ZIP 34119, with a median building coverage of $250,000. Unincorporated Collier County is a CRS Class 5 community in the FEMA NFIP Community Status Book, which earns a 25 percent premium discount in the Special Flood Hazard Area and 10 percent outside it.

Whether your lender requires a flood policy depends on the building. The effective May 16, 2012 FEMA map shows much of the Olde Cypress PUD in Zone AH; the preliminary map issued March 20, 2025 shows the Olde Cypress PUD homes in Zone X, but it is not effective yet (Collier County opened the appeal period August 19, 2026, with the new map targeted for summer 2027). Lantana was removed from the Special Flood Hazard Area by a 2013 LOMR-F. Letters of map change are address-specific, and lenders decide per building, so get the elevation certificate and a quote for the specific home.

Capital Contribution and Transfer Fees at Resale

Section 8.13 of the restated declaration lets the master association collect a working capital contribution “at the time of the transfer of title of any Parcel,” in an amount “as the Board may from time to time determine.” It is not an assessment and not a reserve. We could not locate the current Board-set amount in any public document, and we could not locate any neighborhood-level capital contribution or transfer fee either. The estoppel certificate for the home will state what applies.

How to Get the Real Numbers Before You Sign

Three documents replace every estimate on this page with real numbers for the specific home:

1. The estoppel certificate. Under Section 720.30851 of the Florida Statutes, a homeowners association must issue an estoppel certificate stating the regular assessment, its frequency, the amount paid through, any balance due, and any capital contribution or transfer fee due at closing. Order one from the neighborhood association for the specific lot (through Alliant for most Olde Cypress neighborhoods), and confirm it covers the master share. The title company normally orders it; ask to see it before your inspection period ends.
2. The club membership documents. Ask the club’s membership office at (239) 596-4797 for the current social dues, any golf initiation and dues for the category you want, and whether the seller’s golf membership can transfer or must be purchased new. Get it in writing and make your contract contingent on it if golf matters to you.
3. The neighborhood association budget. Ask the seller, or the neighborhood association through Alliant at (239) 454-1101, for the current adopted budget and the master association budget. The budget shows what the quarterly invoice pays for, the reserve funding, and whether any special assessment is pending.

In the last 12 months we tracked 26 Olde Cypress closings in the Southwest Florida MLS Matrix, pulled September 26, 2026, with a median sold price of $1,105,000. On a home at that level, the difference between two neighborhoods’ quarterly invoices, or between a social and a golf membership, belongs in the offer price. A seller who has the estoppel figure, the club dues letter and the budget in hand before listing removes the questions buyers use to negotiate. Call Jesse direct at (239) 898-6072 for a free valuation of your Olde Cypress home that accounts for your neighborhood’s carrying costs. Buyers, Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.

Does Olde Cypress Have a CDD?

No. Olde Cypress has no Community Development District. Some older descriptions say otherwise; the public record does not support them. Three independent checks agree:

• Collier County’s CDD map. The county’s Community Development Districts layer lists 33 districts, none of them Olde Cypress, and a location test inside the community returns no district.
• The state list. The Florida Commerce All Dissolved Special Districts report, dated September 23, 2026, shows ten dissolved Collier County districts and none named Olde Cypress or Woodlands, so there is no past district either.
• The tax bill. The 2025 Collier County Tax Collector bill for a Lone Pine Ln home carries one non-ad valorem line, District 1 Garbage at $261.91, and no CDD assessment.

Olde Cypress’s roads, stormwater, lakes and common areas are funded privately through the master and neighborhood assessments, not through a CDD bond. For a buyer that means no CDD debt line on the tax bill; the carrying cost lives in the quarterly invoice instead. As the leaders of Domain Realty Group, our team has closed over $2.5 billion in real estate, and we check this line on every North Naples purchase. If you want the same diligence on an Olde Cypress home, Call Marc at (239) 287-5873, or compare notes on the best real estate agents in Naples, compared on the public record.

McGreevy and Comisar have been Top 1% Real Estate Agents Nationally Since 2008, and every Olde Cypress figure on this page is one we would put in front of a buyer or a seller at the kitchen table.

What Are the Neighborhoods Inside Olde Cypress?

Olde Cypress is nine neighborhood associations under one master association, with 548 single-family homes on the 2026 preliminary Collier County roll: the three-unit Olde Cypress HOA (185 homes), Biscayne Place, Egret Cove, Santa Rosa, Santorini, Strada Bella, Terramar, Da Vinci Estates and Lantana. Santorini’s 55 paired villas are the only attached homes.

Data updated: September 2026

That list comes straight from the source that governs it. The Olde Cypress Master Property Owners Association’s About page describes “nine Neighborhood Homeowners Associations (NHOA) and a Master Property Owners Association (MPOA)”, and the association’s own Olde Cypress Neighborhood Site Map colors each of the nine and places a single gatehouse on Treeline Drive just east of Logan Boulevard North. The master association rounds the total to “550 single-family estate homes and attached villa residences.” Our own home-by-home count of the Collier County Property Appraiser 2026 preliminary roll finds 548, and that number only reconciles when Lantana and Da Vinci Estates are included, even though each of those two neighborhoods sits in its own zoning PUD next to the original Olde Cypress PUD.

Every home is reached through one road entrance. Collier County’s road centerline layer shows Treeline Drive connecting to Logan Boulevard North, Olde Cypress Drive, Lantana Circle and Wild Orchid Court, and Olde Cypress Drive feeding every other neighborhood street. Neither Treeline Drive nor Olde Cypress Drive touches Immokalee Road. There is no Olde Cypress Boulevard entrance.

The arithmetic: 185 + 8 + 18 + 27 + 55 + 18 + 55 + 60 + 122 = 548. Home counts, lot sizes and just values come from the Collier County Property Appraiser 2026 preliminary roll and its parcel polygons. Just values are the county’s assessed “just value” for tax purposes, not prices, and they are preliminary until the roll is certified. Build eras are brackets read from Collier County’s building footprint layers for 2000 to 2025: the first county layer that shows a house on the lot, which bounds when it was finished rather than the exact year built. “Typical view” counts homes whose lot sits within 10 feet of the golf course, a lake or a preserve parcel on the county map; lakes inside the golf parcel count as golf, so water views are understated.

Three things hold in every one of the nine. First, the 2019 Amended and Restated Declaration for Olde Cypress (OR 5700 PG 1118) makes every owner a social member of The Club at Olde Cypress and sets the master leasing rule: no lease under 60 days and no more than four leasehold interests per parcel per calendar year. Second, the MPOA About page says owners receive a quarterly invoice from their neighborhood association that includes the neighborhood’s costs plus the owner’s share of the master association, and that the fee includes basic exterior landscaping of each home. The dollar amounts are not published outside the resident portal; they come from each neighborhood’s budget and the estoppel certificate at contract. Third, the Collier County Public Schools address lookup for 2026-2027 assigns every single-family street in all nine neighborhoods to Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High.

On price, the neighborhoods sort into clear tiers. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show 72 qualified single-family sales across the 548 homes in the 36 months to the file date, at a median of $1,302,500. Da Vinci Estates leads at a $2,387,500 median on 12 sales; Santorini sits at the other end at $640,000 on 11. Every neighborhood figure below is a small sample, labeled as such, and the latest recorded sale in the county file is May 22, 2026, so the most recent summer closings are not yet in it. On the MLS side, which is a different record covering a different window, in the last 12 months we tracked 26 Olde Cypress closings in the Southwest Florida MLS Matrix, pulled September 26, 2026, at a median sold price of $1,105,000.

Flood status also varies more by neighborhood than most buyers expect. On the effective May 16, 2012 FEMA map, many footprints in the original Olde Cypress PUD touch Zone AH, the shallow ponding zone, while FEMA’s preliminary flood map issued March 20, 2025 places every one of those 366 PUD footprints in Zone X. Lantana runs the other way. Each section below gives the neighborhood’s own count from the FEMA National Flood Hazard Layer footprint test. A Letter of Map Amendment (LOMA) or Letter of Map Revision based on Fill (LOMR-F) is address-specific, the preliminary map is not effective yet (Collier County opened the 90-day appeal period on August 19, 2026 and targets summer 2027), and lenders decide flood insurance requirements per building.

Olde Cypress HOA: Units One, Two and Three

The largest neighborhood inside Olde Cypress is not one plat but three. Olde Cypress Homeowners’ Association, Inc., filed with the Florida Division of Corporations on February 19, 1999 and listed on the Sunbiz Olde Cypress entity search, governs 185 detached homes across Olde Cypress Unit One, Unit Two and Unit Three. Its current covenants are the 2016 Amended and Restated Declaration for the Olde Cypress Homeowners’ Association (OR 5260 PG 3502). The declarant of record for these plats is the master declarant, Olde Cypress Development, the Stock-affiliated entity that still holds title to the golf course. “Wild Orchid” and “Treeline” are streets inside this association, not separate neighborhoods, and a 2010 county development summary in the April 26, 2011 Board of County Commissioners packet used the older names “Woodsedge” (130 homes) and “Ibis Landing” (55), counts that match Units One and Two combined and Unit Three.

Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show 20 sales across the three units in 36 months, a median of $1,280,000 (the mean of the middle pair, $1,275,000 and $1,285,000). The median 2026 preliminary just value across all 185 homes is $1,195,234.

Unit One: Olde Cypress Drive and West Treeline Drive

Unit One holds 61 homes, 42 on Olde Cypress Drive and 19 on Treeline Drive, recorded at Plat Book 32, Pages 1 to 11. It is the master plat: it also carries the master association’s tracts and the club parcel. Lots run from 13,080 to 21,520 square feet (median 14,257), and 60 of 61 back onto the golf course. County footprints show most homes finished between about 1999 and 2006. The 36-month county record is 6 sales at a $1,847,500 median (middle pair $1,715,000 and $1,980,000), a small sample. On the effective 2012 FEMA map, 11 footprints sit wholly in Zone AH, 20 partly, and 30 wholly in Zone X.

Unit Two: East Treeline Drive and Wild Orchid Court

Unit Two holds 69 homes, 44 on Treeline Drive and 25 on Wild Orchid Court. Lots run 11,445 to 21,016 square feet (median 13,440), 55 back onto the course, and 18 border the master preserve on the east side. Most were finished about 2000 to 2007, with single homes appearing on the county layers in 2011, 2014, 2016, 2018 and two in 2023; whether those are late first builds or rebuilds is not shown in the county data. The 36-month record is 6 sales at a $1,305,000 median (middle pair $1,285,000 and $1,325,000), with a high of $2,600,000, a small sample. Unit Two has the heaviest mapped Zone AH exposure in the association on the effective map: 30 wholly, 35 partly, 4 wholly Zone X. FEMA LOMA 12-04-7997A is one of eight structure-removal letters FEMA has issued for homes on Treeline Drive and Wild Orchid Court, across Units One and Two, since 2012.

Unit Three: Lone Pine Lane

Unit Three is Lone Pine Lane, 55 homes and, with Egret Cove, one of the two most compact detached products in the community: lots of 7,534 to 19,852 square feet (median 9,785) and a median county footprint of 3,748 square feet. It splits between golf (26 homes) and the large master preserve (33). Homes were finished about 2000 to 2007. The 36-month county record is 8 sales at a $972,500 median (middle pair $940,000 and $1,005,000), a small sample, and Lone Pine Lane has been busy in 2026, with five recorded sales between February and May. On the effective map, 29 footprints are wholly Zone AH, 14 partly and 12 Zone X; six Lone Pine homes hold FEMA structure-removal letters, most recently LOMA 25-04-6753A in September 2025. On the March 2025 preliminary map, all 185 homes in the association fall in Zone X.

A dedicated Units One, Two and Three at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Biscayne Place

Biscayne Place is the smallest neighborhood in Olde Cypress: 8 detached estate homes, 5 on Treeline Drive and 3 on Olde Cypress Drive, clustered at the corner where the two streets meet just inside the gatehouse. On the county roll these 8 homes are platted as Olde Cypress Tract 12. Our match of Tract 12 to the Biscayne Place name is based on the master association’s Olde Cypress Neighborhood Site Map, which draws the orange “Biscayne Place” wedge exactly over the Tract 12 lots, with no other plat in that location. The recorded Tract 12 plat itself was not in the documents we read, so treat the name-to-plat match as map-based.

The neighborhood’s governing document is the Biscayne Place Declaration, Articles and Bylaws, recorded April 21, 2004 at OR 3547 PG 1426, with Florida Bay Partners, Inc. as declarant. Biscayne Place Homeowners Association, Inc. was filed with the state on April 14, 2004 and is managed, like the master association, by Alliant Property Management (Sunbiz Biscayne Place entity search).

Build era and lots. County footprint layers show two homes finished by 2004, five by 2006 and one by 2007, so Biscayne Place came after the first wave of Olde Cypress construction. The lots are among the largest in the community: 15,019 to 21,840 square feet, median 16,680, second only to Da Vinci Estates. The median county building footprint is 6,845 square feet, the largest of any neighborhood (the footprint includes garage and covered lanai, so it is not living area). All 8 homes back onto the golf course.

Values. Biscayne Place carries the highest median 2026 preliminary just value in Olde Cypress, $1,704,810, and the highest median total tax bill on the preliminary roll, $15,120. Those are assessment figures for tax purposes, not market prices.

Recorded sales. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show no qualified sale in Biscayne Place in the 36 months to the file date. Going back five years there is one: $2,050,000, recorded in January 2022. Before that, the county file shows qualified sales of $1,175,000 in September 2017 and $1,115,000 in December 2012. With eight homes, a resale here is a rare event, and pricing one means building comparables from Unit One, Strada Bella and Da Vinci Estates, then adjusting for the lot size and the corner location near the gate.

Flood. On the effective May 16, 2012 FEMA map, 5 of the 8 footprints sit wholly in Zone AH and 3 partly, with nearby base flood elevation lines at 12.0 to 12.5 feet NAVD88; none sits wholly in Zone X. We found no FEMA LOMA on record for a Biscayne Place home. On the March 20, 2025 preliminary map, all 8 fall in Zone X, but that map is not effective yet. For a buyer here, the elevation certificate and the lender’s flood determination for the specific house matter more than for almost any other neighborhood in the community.

What sets it apart. Biscayne Place is the closest neighborhood to the gatehouse and to the clubhouse, which sits west of the gate. For a buyer who wants a large-lot golf home in Olde Cypress without driving deep into the community, it is the first address inside the gate; the trade-off is that with eight homes, waiting for one to come up can take years.

A dedicated Biscayne Place at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Egret Cove

Egret Cove is 18 detached homes on one cul-de-sac, Olde Cove Way, off Olde Cypress Drive. On the county roll the neighborhood is platted as Olde Cypress Tract 9, and its common road tract is titled to Egret Cove of Naples Homeowners’ Association, Inc. on the 2026 preliminary roll; the master association’s site map labels the Olde Cove Way enclave “Egret Cove.” The neighborhood’s original declaration is recorded at OR 2628 PG 2418, and its current governing documents are the Egret Cove amended governing documents (OR 4466 PG 1002). No builder or declarant name for Egret Cove appeared in the recorded pages available to us, so we do not name one.

Two cautions on the name. A different Florida corporation called Egret Cove Neighborhood Association, Inc., based on the east coast, shows up in state searches and has nothing to do with Olde Cypress. And a brokerage-circulated description of Olde Cypress has called Egret Cove a “villa enclave”; the county footprints show 18 detached homes, not villas.

Build era and lots. Egret Cove went up in the tightest window of any neighborhood: two homes finished by 2000, fourteen by 2002 and the last two by 2004. Lots run 6,720 to 14,080 square feet, median 9,618, and the median county footprint is 3,284 square feet, one of the more compact detached products in the community alongside Lone Pine Lane. All 18 homes back onto the golf course, which is the neighborhood’s defining feature: a short cul-de-sac where every rear view is fairway.

Values. The median 2026 preliminary just value is $828,724, the second lowest of the nine neighborhoods after Santorini (the Lone Pine Lane plat on its own runs lower, at $783,010), with a median total tax bill of $5,096 on the preliminary roll.

Recorded sales. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show no qualified Egret Cove sale in the 36 months to the file date. In the five-year window there are two: $790,000 recorded in October 2021 and $1,025,000 recorded in February 2023. The earlier 2020 and 2021 record includes sales of $590,000 to $785,000. Two sales are not a trend, and the gap since February 2023 means a current Egret Cove price has to be built from Lone Pine Lane and Terramar comparables and adjusted for the full golf exposure.

Flood. On the effective May 16, 2012 FEMA map, Egret Cove has one of the lighter mapped exposures in the original PUD: 3 footprints wholly in Zone AH, 7 partly, and 8 wholly in Zone X, with the nearest base flood elevation line at 12.0 feet NAVD88. Two Olde Cove Way homes hold FEMA structure-removal letters (LOMA 12-04-7634A in 2012 and LOMA 14-04-9458A in 2014). On the March 20, 2025 preliminary map, all 18 homes fall in Zone X. The preliminary map is not yet effective, and a LOMA covers only the address it names.

What sets it apart. Egret Cove is the entry point to all-golf, detached living in Olde Cypress: 18 homes, a single street with no through traffic, and a 100 percent golf-adjacent count. Buyers comparing it with Santorini should note the difference in product: Santorini homes share a wall; Egret Cove homes do not.

A dedicated Egret Cove at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Santa Rosa

Santa Rosa at Olde Cypress is 27 detached homes, 26 on Monteverde Way and one on Olde Cypress Drive, recorded as its own plat, Santa Rosa at Olde Cypress. Santa Rosa at Olde Cypress Homeowners’ Association, Inc. was filed with the state on April 9, 2001 and owns the neighborhood’s road tract on the 2026 preliminary roll. Its original declaration is recorded at OR 3057 PG 2810, restated in 2006 (OR 4144 PG 425) and again in 2011; the current version is the 2011 Amended Declaration, Articles and Bylaws for Santa Rosa (OR 4722 PG 375). No builder of record appeared in the pages available to us, so we do not name one. Unlike most of the other neighborhoods, the Santa Rosa association lists an outside registered agent rather than the master association’s manager.

Build era and lots. Santa Rosa was built in two pulses: two homes by 2000, seven by 2002 and two by 2004, then fourteen by 2006 and two by 2007. More than half of the homes therefore date to the 2004 to 2007 period. Lots run 8,602 to 16,006 square feet, median 9,907, and the median county footprint is 4,383 square feet. Every one of the 27 homes backs onto the golf course.

Values. The median 2026 preliminary just value is $1,079,324, with a median total tax bill of $7,692 on the preliminary roll.

Recorded sales. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show 3 qualified sales in the 36 months to the file date, a median of $1,512,500, a small sample. The three are $1,229,000 (April 2024), $1,600,000 (November 2025) and $1,512,500 (November 2025). That median sits well above the neighborhood’s median just value, which is typical in Florida, where the assessed just value lags the market and homestead caps hold assessed values down further. The five-year record adds two more sales, for 5 at the same $1,512,500 median, with a high of $1,825,000.

Flood. On the effective May 16, 2012 FEMA map, 12 Santa Rosa footprints sit wholly in Zone AH, 11 partly and 4 wholly in Zone X, with nearby base flood elevation lines at 12.0 to 12.5 feet NAVD88. Three Monteverde Way homes hold FEMA structure-removal letters issued between 2017 and 2022; LOMA 17-04-2382A records a lowest adjacent grade of 14.6 feet NAVD88, and LOMA 22-04-3044A records 13.8 feet. On the March 20, 2025 preliminary map, all 27 homes fall in Zone X. A LOMA is address-specific, and the preliminary map is not effective until FEMA finalizes it.

What sets it apart. Santa Rosa is a single-street golf neighborhood in the middle of the community with a 100 percent golf-adjacent count and lots close to Terramar’s in size, but its recent recorded sales have run noticeably higher than Terramar’s. With 27 homes and three sales in three years, one or two closings can move the Santa Rosa median a long way, so a seller here should price against the specific lot, orientation and condition rather than the neighborhood average.

A dedicated Santa Rosa at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Santorini

Santorini Villas at Olde Cypress is the only attached product inside Olde Cypress: 55 villa residences on Santorini Court. The county’s 2025 building footprint layer shows the 55 lots under 28 buildings, each spanning two lots, so the homes are paired villas that share a wall. (Twenty-eight two-lot buildings would be 56 homes; how the odd 55th lot is configured is a question for the plat or a site visit.) This is the “attached villa residences” the master association refers to when it describes “550 single-family estate homes and attached villa residences” on its About page. A brokerage-circulated list of Olde Cypress “villa enclaves” also names Ibis Landing and Egret Cove; on the county roll, Santorini is the only villa product.

Santorini Villas Homeowners’ Association, Inc. was filed with the state on April 19, 2000 and is managed by Alliant Property Management. It owns the road tract and three common tracts on the 2026 preliminary roll. The current documents are the 2013 combined restated documents for Santorini (OR 4911 PG 1167), amended in 2019 (OR 5627 PG 1158, the Santorini amendment). No builder of record appeared in the pages available to us.

Build era and lots. County footprints show 20 villas by 2002, 15 more by 2004 and the last 20 by 2006. Lots run 5,428 to 15,700 square feet, median 6,639, the smallest in Olde Cypress, and the median footprint inside each lot is about 3,078 square feet, with whole two-home buildings near 6,000. Thirty-six of the 55 villas back onto the golf course.

Values. The median 2026 preliminary just value is $558,186, the lowest of the nine neighborhoods, with a median total tax bill of $4,720 on the preliminary roll. Santorini is the entry price for an Olde Cypress address and for the mandatory club social membership that comes with it.

Recorded sales. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show 11 qualified sales in the 36 months to the file date, a median of $640,000, with a range of $475,000 to $800,000. That is the only neighborhood besides Da Vinci Estates and Lantana with more than ten sales in the window, and it is still a thin record. The most recent three were $800,000 (November 2025), $634,800 (January 2026) and $643,000 (May 2026). The 60-month record shows 18 sales at a $646,500 median, which says the villa market has been steady rather than climbing over the past three years.

Flood. On the effective May 16, 2012 FEMA map, Santorini has the most Zone AH footprints of any neighborhood in the original PUD: 32 wholly, 7 partly and 16 wholly in Zone X, with nearby base flood elevation lines at 13.0 to 13.5 feet NAVD88. It also has the most FEMA letters: eleven LOMAs issued on Santorini Court homes between 2012 and 2017, including LOMA 12-04-6701A, which records a lowest adjacent grade of 14.3 feet. Because two villas share a building, one side can hold a LOMA while the other does not. On the March 20, 2025 preliminary map, all 55 villas fall in Zone X; that map is not effective yet.

What sets it apart. Shared walls mean shared decisions: roof, exterior paint and structural repairs on a paired villa involve a neighbor and the villa association’s rules, so a buyer should read the Santorini documents for who maintains what before writing an offer.

A dedicated Santorini at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Strada Bella

Strada Bella is 18 detached estate homes on Strada Bella Court, at the north edge of Olde Cypress off Olde Cypress Drive. It is one of the few neighborhoods whose builder-declarant is on the record: the Strada Bella Declaration of Covenants, recorded September 15, 2003 at OR 3397 PG 1946, names Strada Bella Development, LLC as declarant, and the land is Tract 7 of Olde Cypress Unit One (Plat Book 32, Pages 1 to 11), confirmed by an October 2003 amendment to the Strada Bella declaration. Strada Bella at Olde Cypress Neighborhood Association, Inc. was filed with the state on September 11, 2003, is managed by Alliant Property Management, and owns the neighborhood’s common tracts on the 2026 preliminary roll.

Build era and lots. Strada Bella is a second-wave neighborhood. County footprint layers show two homes by 2004, twelve by 2006, three by 2007 and one by 2014. Lots run 11,497 to 20,859 square feet, median 12,789, and the median county footprint is 5,501 square feet, in the same class as Unit One. Seventeen of the 18 homes back onto the golf course. At a 2010 neighborhood information meeting recorded in the April 26, 2011 Board of County Commissioners packet, residents noted pedestrian access from Logan Boulevard into Strada Bella; vehicles still enter through the Treeline Drive gate.

Values. The median 2026 preliminary just value is $1,365,158, third highest of the nine neighborhoods after Biscayne Place and Da Vinci Estates, with a median total tax bill of $9,545 on the preliminary roll.

Recorded sales. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show one qualified Strada Bella sale in the 36 months to the file date: $1,775,000, recorded in April 2025. With a single sale there is no median to report. The sale before it in the county file is $1,190,000 in April 2021, and 2020 sales ran $815,000 to $870,000, which shows how far Strada Bella values moved after 2020. With 18 homes, a year or more can pass between resales.

Flood. On the effective May 16, 2012 FEMA map, 12 Strada Bella footprints sit wholly in Zone AH, 5 partly and 1 wholly in Zone X, with nearby base flood elevation lines at 12.5 to 13.0 feet NAVD88. That mapped exposure is offset by the record: seven FEMA letters cover Strada Bella property, including LOMA 12-04-5230A, which removed one Strada Bella lot and three Terramar lots to shaded Zone X in 2012, and LOMA 13-04-2232A, which records a lowest adjacent grade of 14.0 feet. On the March 20, 2025 preliminary map, all 18 homes fall in Zone X. Each letter is address-specific, and the preliminary map is not yet effective.

What sets it apart. Strada Bella offers estate-size golf lots on a short court at the quiet north end of the community, with a recorded declarant and a later build date than most of Olde Cypress. The trade-off is distance: from the gatehouse, the Strada Bella Court area is about 1.36 road miles in.

A dedicated Strada Bella at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Terramar

Terramar is 55 detached homes on Terramar Drive (43) and Terramar Court (12), on the west side of Olde Cypress. It has the oldest recorded neighborhood declaration we found in the community: the Terramar Declaration recorded June 21, 2000 at OR 2689 PG 1846, with Terramar Development, Inc. as declarant and the plat at Plat Book 34, Page 9. A 2003 amendment to the Terramar declaration (OR 3288 PG 1762, recorded May 12, 2003) brought in Sussex Homes at Olde Cypress, LLC as successor developer. Terramar at Olde Cypress Homeowners Association, Inc. was filed with the state on April 27, 2000.

One oddity shows up on the 2026 preliminary roll: Terramar’s road tract (2.44 acres) and one common tract are still titled to Terramar Development, Inc., not to the homeowners association, while every other neighborhood association holds its own tracts. That is a title question for a buyer’s closing attorney or title agent, not a reason to avoid the neighborhood, but it belongs on the due-diligence list.

Build era and lots. County footprints show two homes by 2000, eighteen by 2002, twenty by 2004 and fifteen by 2006. Lots run 9,003 to 19,454 square feet, median 10,479, and the median county footprint is 4,858 square feet. All 55 homes back onto the golf course.

Values. The median 2026 preliminary just value is $965,006, with a median total tax bill of $7,334 on the preliminary roll.

Recorded sales. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show 8 qualified sales in the 36 months to the file date, a median of $1,137,000 (the mean of the middle pair, $1,099,000 and $1,175,000), a small sample. The range runs from $850,000 to $1,900,000, which says Terramar is two markets: interior-facing and updated golf-view homes can trade far apart. Four of the eight came in the last 12 months of the file: $1,175,000 (September 2025), $1,075,000 (December 2025), $1,099,000 (February 2026) and $1,750,000 (March 2026).

Flood. On the effective May 16, 2012 FEMA map, Terramar has only 7 footprints wholly in Zone AH, 31 partly (many clipping only a sliver) and 17 wholly in Zone X, with base flood elevation lines of 11.5 to 12.5 feet NAVD88. Four Terramar lots touch Zone AE along the lake edge. LOMA 12-04-5230A removed three Terramar lots to shaded Zone X in 2012. On the March 20, 2025 preliminary map, all 55 homes fall in Zone X. The preliminary map is not effective yet, and lenders decide per building.

What sets it apart. Terramar gives the most golf frontage for the money among the detached neighborhoods: every lot on the course, lot sizes in line with Santa Rosa and Lantana, and a median just value below both. It sits closest to the Logan Boulevard side, west across the community from Lone Pine Lane.

A dedicated Terramar at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Da Vinci Estates

Da Vinci Estates is 60 detached estate homes on Mona Lisa Boulevard (43), Leonardo Avenue (9), Renaissance Court (4) and Florentine Court (4), with the largest lots in Olde Cypress. It sits in its own zoning district, the “Da Vinci Estates, Olde Cypress” PUD approved by Ordinance 01-36 on June 26, 2001: 40.37 acres, 61 single-family homes authorized and 8.20 conservation acres, per the Collier County PUD Master List dated June 11, 2026, which lists the district as closed out. The master list counts 59 homes developed; the 2026 preliminary roll shows 60 single-family lots.

Da Vinci Estates is a member neighborhood of the Olde Cypress master association, and the recorded document says so directly. The Da Vinci Estates declaration, recorded October 31, 2000 at OR 2737 PG 2884 with H.B. Holdings of Southwest Florida, L.L.C. as declarant, subjects the lots to the Olde Cypress master declaration (OR 2539 PG 2902) and makes each owner a member of the master association, carrying the same mandatory club social membership as every other Olde Cypress owner. Leonardo Avenue’s only road connection is Olde Cypress Drive, so the neighborhood is reached only through the Treeline Drive gate. Da Vinci Estates Homeowners’ Association, Inc. was filed with the state on November 3, 2000 (Sunbiz Da Vinci Estates entity search) and uses a different management company from the master association.

Build era and lots. County footprints show one home by 2002, fifteen by 2004, twenty-nine by 2006, nine by 2007, five by 2009 and one by 2013, so most of Da Vinci Estates was finished between about 2003 and 2009. Lots run 12,652 to 26,460 square feet, median 18,263, and the median county footprint is 6,281 square feet (up to 9,423). The neighborhood is the most varied in outlook: 34 homes are lake-adjacent (a central lake inside the Mona Lisa Boulevard loop), 28 golf-adjacent and 24 preserve-adjacent, some touching more than one. The association owns ten preserve tracts and four lake tracts on the 2026 preliminary roll.

Values. The median 2026 preliminary just value is $1,657,416, and Da Vinci Estates holds the single highest just value in the community, $2,855,721.

Recorded sales. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show 12 qualified sales in the 36 months to the file date, a median of $2,387,500 (the mean of the middle pair, $2,350,000 and $2,425,000), with a range of $1,660,000 to $2,990,000. That is the highest neighborhood median in Olde Cypress and one of only three neighborhoods above ten sales. The top recorded sale in the window is $2,990,000 in January 2026. The five-year record shows 21 sales at a $2,200,000 median.

Flood. On the effective May 16, 2012 FEMA map, 12 Da Vinci footprints sit wholly in Zone AH, 35 partly and 13 wholly in Zone X, with base flood elevation lines at 11.5 to 12.5 feet NAVD88; a few lots touch Zone AE. Three FEMA letters cover Da Vinci property, including LOMR-F 15-04-1747A, with a lowest adjacent grade of 15.7 feet, and LOMA 21-04-1457A. On the March 20, 2025 preliminary map, 59 of 60 homes fall wholly in Zone X unshaded and one partly touches Zone AH. That map is not effective yet.

A dedicated Da Vinci Estates at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Lantana

Lantana is the newest neighborhood in Olde Cypress and the largest single association: 122 detached homes on Lantana Circle (97) and Lantana Way (25), south of Treeline Drive between the gatehouse and Immokalee Road. County footprint layers show six homes by 2013, fifty-two by 2014, forty by 2015 and twenty-four by 2016, so the whole neighborhood was built in four years, a decade after most of Olde Cypress, under the Florida Building Code editions of that era. A 2016 Naples Daily News report that Lantana at Olde Cypress had sold out marked the end of new-home sales there.

Zoning and declarant. Lantana sits in the H.D. Development PUD, also known as Vita Tuscana. Collier County approved it at 71 single-family and 33 multifamily units, then Ordinance 2011-13, adopted April 26, 2011 as shown in the Board of County Commissioners recap for that date, allowed 125 single-family and 33 multifamily units; 122 homes were built. The Lantana Declaration of Covenants, recorded April 4, 2013 at OR 4904 PG 1443, names Vita Pima, LLC as declarant, describes it as an affiliate of the club owner, subjects the lots to the Olde Cypress master declaration and makes each owner a master association member. Lantana at Olde Cypress Homeowner’s Association, Inc. was filed with the state on November 30, 2012 (Sunbiz Lantana at Olde Cypress entity search) and is managed by Alliant Property Management. Lantana Circle’s only road connection is Treeline Drive, inside the gate.

The club discount history. The same 2016 Naples Daily News report described a $15,000 discount off the then-current Full Golf initiation for Lantana buyers. That was a 2016 incentive tied to new-home sales. The club does not publish current initiation or dues on its site; the current figure comes from the club’s membership office at (239) 596-4797 and belongs in the contract review.

Lots and views. Lots run 7,618 to 16,950 square feet, median 10,116, and the median county footprint is 4,392 square feet. Lantana is lake-oriented rather than golf-oriented: 66 homes border one of the association’s lakes, 19 the 16.23-acre association preserve and 13 the golf course and practice-range edge.

Values and sales. The median 2026 preliminary just value is $1,045,298. Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show 17 qualified sales in the 36 months to the file date, a median of $1,320,000, with a range of $841,000 to $1,795,000, the most active record of any neighborhood. Six recorded between January and May 2026, four of them at $1,590,000 or more.

Flood, three layers. Lantana needs the most careful reading. The effective May 16, 2012 FEMA map graphic still paints 116 of 122 footprints in Zone AH. But FEMA LOMR-F 13-04-6118A, dated August 8, 2013, removed Lots 1 through 122 (Plat Book 52, Pages 47 to 52) from the Special Flood Hazard Area to unshaded Zone X, with a lowest lot elevation of 12.9 feet NAVD88; letters of map change are not redrawn onto the panel image. Then the March 20, 2025 preliminary map re-draws Zone AH across part of the neighborhood: 72 of 122 footprints touch Zone AH, 47 fall wholly in shaded Zone X and 3 are mixed. If that map becomes effective as issued, part of Lantana could move back into a mapped flood zone; whether FEMA revalidates the 2013 letter is its decision. The appeal period opened August 19, 2026.

A dedicated Lantana at Olde Cypress sub-page is coming with its association details, recent sale comps and street-by-street analysis. We’ll link it here when it goes live.

Is Fairway Preserve at Olde Cypress Part of Olde Cypress?

No. Fairway Preserve at Olde Cypress is a separate 264-unit condominium with its own gate, its own association and its own entrance off Immokalee Road. It carries the Olde Cypress name and sits inside the boundary of the Olde Cypress PUD, which is why listing feeds and search results keep folding it in, but it is not one of the nine neighborhoods and not part of the gated community.

The evidence runs in five directions.

The master association’s own map leaves it out. The Olde Cypress Neighborhood Site Map colors nine neighborhoods and does not draw Fairway Preserve, and the MPOA About page counts nine neighborhood associations. Adding Fairway Preserve’s 264 units to the 548 homes would give 812, which cannot be squared with the master association’s “550.”

The roads do not connect. In Collier County’s road centerline layer, Preserve Circle connects only to Dancing Wind Lane, which runs to Immokalee Road. There is no road link to Treeline Drive or Olde Cypress Drive. The condominium’s own association website describes it as “a 264 unit 3 story condominium located just over 2 miles east of I-75 on Immokalee Rd,” and it runs its own LiftMaster tele-entry gate.

It has its own recorded declaration and developer. The Declaration of Condominium of Fairway Preserve at Olde Cypress, recorded August 12, 2005 at OR 3866 PG 4006, was made by Fairway Preserve Apartments at Olde Cypress, Ltd., and the pages we read do not reference the Olde Cypress master association. The condominium association was filed with the state on July 18, 2005 (Sunbiz Fairway Preserve at Olde Cypress entity search). County footprint layers show the buildings standing by 2002, so the property was built as apartments and converted to a condominium in 2005. It is 11 three-story buildings of 24 units each, on Preserve Circle (not “Preserve Way,” a name that circulates online).

It has its own amenities. The association lists a heated pool, spa, fitness room, racquetball court, petanque and horseshoes, and a gathering room on its community amenities page. Its rules and regulations update of March 25, 2021 require Board pre-approval of all pets and bar several named breeds, rules that do not apply inside Olde Cypress.

It is zoned to a different high school. The Collier County Public Schools address lookup for 2026-2027 sends every Preserve Circle building to Laurel Oak Elementary, Oakridge Middle and Gulf Coast High, not Aubrey Rogers High. Gulf Coast High earned an A in each of the last three state grade releases and 69 percent of points in 2026, per the Naples Daily News republication of Florida Department of Education grades.

What three stories means in Florida. Because Fairway Preserve’s buildings are three stories, they fall under Florida’s condominium milestone inspection law (section 553.899, Florida Statutes, which covers buildings three stories or more) and the structural integrity reserve study (SIRS) requirement in section 718.112(2)(g). For a buyer, that means asking for the association’s milestone inspection reports, its SIRS and its reserve funding before signing, because underfunded reserves can become special assessments. We did not confirm Fairway Preserve’s filing status; the Florida DBPR SIRS reporting page is where to check. None of this applies to the 548 single-family homes inside Olde Cypress, which are not condominiums.

The numbers. The median 2026 preliminary just value of the 264 units is $205,970, a different market from anything behind the Treeline Drive gate. On the effective May 16, 2012 FEMA map, 29 of the 37 building footprints the county building layer maps on the site (a structure count, larger than the 11 residential buildings) are wholly in Zone X, 7 partly in the Special Flood Hazard Area and 1 wholly; FEMA letters LOMA 13-04-1079A and 13-04-0877A removed Buildings 6, 10 and 11. On the March 2025 preliminary map, 36 of 37 footprints fall wholly in unshaded Zone X.

Lantana, Da Vinci Estates and “Vita Tuscana”: Why the Names Confuse Buyers

Three zoning districts, two neighborhood names and one leftover label create most of the confusion about what counts as Olde Cypress.

Three PUDs, one community. The original Olde Cypress PUD (Ordinance 2000-37 as amended by 00-53, 538.1 acres) holds 366 of the community’s homes plus land that is not Olde Cypress at all: Fairway Preserve, a separate apartment parcel on Dream Catcher Circle and the Preserve Commons commercial strip on Immokalee Road. Da Vinci Estates (Ordinance 01-36, 40.37 acres) and Lantana (the H.D. Development PUD, 46.64 acres on the county master list) each sit in their own district. A search that draws a line around “the Olde Cypress PUD” catches Fairway Preserve and misses 182 Olde Cypress homes; a search by county zoning name misses Lantana entirely, because the zoning name on its land is not Lantana.

“Vita Tuscana” is the zoning name, not a neighborhood. The county PUD layer and PUD master list carry the Lantana land as “H.D. Development PUD, AKA Vita Tuscana.” The 2011 Board of County Commissioners staff report explains why the name matters: “The removal of the 158 dwelling units from the Olde Cypress PUD will allow the proposed 158 unit HD Development RPUD … to be added to the Olde Cypress DRI.” In other words, Ordinance 2011-14 cut the Olde Cypress PUD cap from 1,100 to 942 units, and Ordinance 2011-13 put those 158 units on the Vita Tuscana land, which became Lantana. County plat records list the Lantana plats as formerly known as Vita Tuscana. So “Vita Tuscana” in older listing data, plat indexes or search results refers to the land where Lantana’s 122 homes now stand. There is no separate Vita Tuscana neighborhood behind the gate.

Italian names, two different neighborhoods. Da Vinci Estates’ streets (Mona Lisa, Leonardo, Renaissance, Florentine) and the Vita Tuscana label both lean Italian, and the declarants make it worse: Da Vinci’s declarant was H.B. Holdings of Southwest Florida, L.L.C., while Lantana’s was Vita Pima, LLC. Buyers and even agents sometimes assume Da Vinci Estates and Vita Tuscana are the same place. They are not: Da Vinci Estates is 60 large-lot homes built about 2003 to 2009 in the interior of the community off Olde Cypress Drive; Lantana is 122 homes built 2013 to 2016 at the south end off Treeline Drive.

Both are fully Olde Cypress. The recorded neighborhood declarations settle membership. The Da Vinci Estates declaration (OR 2737 PG 2884, 2000) and the Lantana Declaration of Covenants (OR 4904 PG 1443, 2013) both subject their lots to the Olde Cypress master declaration recorded at OR 2539 PG 2902 and make each owner a master association member with mandatory club social membership. Both appear as color-coded neighborhoods on the master association’s map, and both are reached only through the Treeline Drive gate.

What this means when you price or search. Search portals and some listing feeds split these neighborhoods off, merge Fairway Preserve in, or file homes under older names like “Woodsedge,” “Ibis Landing” or “Vita Tuscana.” A seller in Lantana or Da Vinci Estates should make sure the listing says “Olde Cypress” plainly, because that is the name buyers search. A buyer comparing prices across the community should confirm which records a quoted median includes; the county figures on this page cover all 548 single-family homes and nothing else.

For a comparison with the neighboring golf communities along Immokalee Road, see our Naples golf communities guide, Longshore Lake directly to the west, and our Naples guide.

Selling a home in any of the nine Olde Cypress neighborhoods? Pricing here is neighborhood by neighborhood: a Lone Pine Lane home and a Da Vinci Estates home share a gate and a club but trade more than a million dollars apart, and several neighborhoods have gone years between sales. As the leaders of Domain Realty Group, our team has closed over $2.5 billion in real estate. Get a free valuation of your Olde Cypress home, or Call Jesse direct at (239) 898-6072 and he will price your home against the recorded sales in your own neighborhood.

Buying in Olde Cypress? Call Marc at (239) 287-5873 before you choose a neighborhood, so you know how the product, lot, flood record and club terms differ from one street to the next, or read how we represent buyers in Southwest Florida.

McGreevy and Comisar have been Top 1% Real Estate Agents Nationally Since 2008, and we price every Olde Cypress home against the recorded sales of its own neighborhood.

Is Membership at The Club at Olde Cypress Mandatory?

Social membership at The Club at Olde Cypress is mandatory for every Olde Cypress homeowner; golf membership is not. The recorded master declaration makes each owner a social member automatically, and the club sells Full Golf and Associate Golf separately, to residents and non-residents alike. The club is non-equity and privately owned, so members hold no ownership stake.

Data updated: September 2026

That one paragraph answers the question buyers ask us most, but the details underneath it decide what an Olde Cypress home really costs to own and what a seller can promise a buyer. Below is what the recorded documents and the club’s own pages say, where they stop, and how we handle the gaps in a contract.

Who Owns The Club at Olde Cypress?

The Club at Olde Cypress is a privately owned, non-equity club. Its own About Us page and member FAQ calls it “a non-equity, privately owned golf and country club owned by Stock Hospitality,” and elsewhere on the same page says it is privately owned by Stock Development. Both are true in practice: the club describes itself as owned by the Stock family of companies, and Stock Hospitality runs day-to-day operations.

The public record fills in the entity underneath the brand. Florida Division of Corporations filings show the golf course land titled to Olde Cypress Development, a limited partnership formed on September 2, 1998, per the 1998 Certificate of Limited Partnership on file with the Florida Division of Corporations. A Stock family member was the funding limited partner from that first filing, three years before the Stock Development brand itself was founded. A sister partnership that originally held the club was merged into the development partnership in 2001, per the 2001 Articles of Merger, and Stock Development became the general partner in February 2003, per the 2003 Certificate of Amendment.

On July 24, 2026 the partnership converted into Olde Cypress Development, LLC, per the 2026 Articles of Conversion. That was a change of legal form, not a sale. The same Stock family entity has held the economic interest in the Olde Cypress course since 1998, and no sale of the club to its members has ever occurred. The Collier County Property Appraiser 2026 preliminary roll still prints the older “Ltd.” owner name on the golf parcels, because the roll had not caught up with the July conversion when it was prepared.

What “Non-Equity” Means for an Olde Cypress Owner

In a non-equity club, members buy the right to use the club, not a share of it. The club’s own explainer, Equity vs. Non-Equity Golf Club Memberships, says “The Club at Olde Cypress is one of the few non-equity clubs in Naples, Florida,” and sums up the model as “Not subject to assessment fees; Non transferable; No ownership; Easy to resign when desired.”

The recorded documents say the same thing from the homeowner’s side. Section 14.01 of the 2019 Amended and Restated Declaration for Olde Cypress (recorded November 27, 2019, Instrument 5796524, OR Book 5700, Page 1118) states that “The Country Club Property is not a part of the Property” and describes it as “a clubhouse, a golf course, tennis courts, and other recreational facilities.” Section 14.03 adds that owners receive no equity, voting or ownership interest in the club property.

Two practical consequences follow. First, Olde Cypress homeowners do not vote on club budgets, capital projects or dues; the owner sets them. Second, the club cannot pass a capital bill to members the way a member-owned club can. That is why the $16 million clubhouse renovation described later on this page came with no member assessment.

If you have owned in a member-owned equity club before, this is the biggest adjustment. You trade a vote for a fixed relationship: the owner carries the capital risk and makes the decisions, and you decide each year whether the membership is worth the dues.

The Three Membership Categories at a Glance

The club’s membership page lists three categories as of September 2026. The table below uses only the club’s published wording; the club publishes no prices for any of them.

The Associate Golf details come from the club’s Associate Golf Membership fact sheet page, which pitches the category to people who want to join a private club “without having to spend years on a waitlist.”

Why Social Membership Is Mandatory: Declaration Section 14.02

The requirement is a recorded covenant, not just a club policy. Section 14.02 of the 2019 Amended and Restated Declaration for Olde Cypress reads: “By acquisition of a Parcel, each Owner automatically becomes a social member of The Club at Olde Cypress.” Dues are payable “as promulgated by The Club … from time to time,” which means the club, not the homeowners’ association, sets the amount.

The declaration also defines what social membership covers: the clubhouse and tennis, but not the golf course except as the guest of a golf member. The club’s membership page repeats the rule in plain terms: “Social Membership is mandatory for all residents of the Olde Cypress community who do not hold a higher category of membership. This category of membership is only available to those residing within the gates.” The club’s real estate page says the same, describing homeownership as “tied to a mandatory Social Membership,” with Full and Associate Golf optional.

The covenant reaches past the original Olde Cypress plats. Da Vinci Estates and Lantana sit in their own zoning districts, but their recorded declarations (Da Vinci Estates at OR Book 2737, Page 2884, and Lantana at OR Book 4904, Page 1443) subject their lots to the Olde Cypress master declaration, so owners there carry the same mandatory social membership.

One neighbor does not. Fairway Preserve at Olde Cypress, the 264-unit condominium with its own gate off Immokalee Road, is not part of the gated community or the master association. Buying a Fairway Preserve condominium does not come with club social membership.

Is Golf Membership Required to Buy in Olde Cypress?

No. Golf is optional at Olde Cypress. A buyer can close on a home, hold only the mandatory social membership, and never join for golf. A buyer who wants golf chooses between Full Golf and Associate Golf and buys it from the club as a separate transaction.

This separates Olde Cypress from bundled golf communities, where every home carries a full golf membership whether the owner plays or not. The club’s own explainer on equity and non-equity memberships describes bundled communities as a different model. At Olde Cypress only Social is required.

Can Non-Residents Join The Club at Olde Cypress?

Yes, for golf. As of September 2026 the club’s membership page says Full Golf memberships “are currently available for residents and non-residents” and that “both resident and non-resident Associate memberships are available.” The club’s FAQ on its About Us page adds: “Residency is not required, and the club is conveniently located outside the community’s gates.”

Social membership is the exception: it is “only available to those residing within the gates.” A person who lives elsewhere in Naples can join for golf, but cannot buy a social-only membership.

Why the Clubhouse Sits Outside the Gate

Both descriptions of Olde Cypress are right. The club’s real estate page calls Olde Cypress “a private, gated golf community,” and the club FAQ says “the club is conveniently located outside the community’s gates.” They describe different parts of the same map.

The single-family homes, which the 2026 Collier County roll counts at 548 and the master association rounds to 550, sit behind one staffed gatehouse on Treeline Drive. The clubhouse, tennis and pickleball courts, pool and practice range sit west of that gatehouse, between it and Logan Boulevard North. The Olde Cypress Neighborhood Site Map published by the master association draws the Clubhouse and Practice Range west of the Gate House. That layout is why non-resident golf members can drive to the club without passing the residential gate, and why the gate staff answer to the master association (guard house (239) 592-5381) while the club answers its own phone at (239) 596-4797.

No Assessments, No Food and Beverage Minimums

Two cost lines that surprise buyers at other Naples clubs do not exist here, according to the club. The FAQ on the club’s About Us page says: “Unlike member-owned clubs, we don’t have assessments to pay for improvements … we don’t have food and beverage minimums.”

We treat those as club policies as of September 2026, stated by the owner, not as recorded covenants. A policy can change; a buyer who is weighing the club’s cost over ten years should read the current membership documents at contract rather than rely on a web page. That said, the owner’s track record supports the statement: the 2021 course renovation and the 2025 to 2026 clubhouse renovation were both paid for without a member assessment.

The $1,950 Private Cart Fee

The one dollar figure the club publishes is its cart plan. The club’s article Naples Private Golf and Country Clubs: Five Things to Know (page stamped “Updated September 22, 2026”) says members may use their own golf carts on the course for an annual fee of $1,950, “and about 60% chose to do so.” The same policy appears in the club FAQ.

The page stamp may be newer than the figure, so confirm the current cart fee with the club when you join. Inside the gate, the recorded declaration lets golf carts use community streets subject to master association rules (Section 9.31), and course carts stay on the course and designated cart paths.

What the Club Does Not Publish: Initiation Fees and Dues

The Club at Olde Cypress does not publish its initiation fees or annual dues. We reviewed every public page on the club’s site in September 2026. The Full Golf Membership Guide, the Associate Golf fact sheet and the Lifestyle Brochure all sit behind a form that asks for your name and email before download, and none of the public pages carries a price.

Figures do circulate online, and they conflict widely. Third-party estimates we found for golf initiation run from roughly $45,000 to $175,000, some of them years old, some of them labeled by their own authors as rumored, and at least one describing an “equity” option that the club’s own statement rules out, because the club is non-equity. None of those numbers comes from the club, and we do not repeat any of them as a price on this page. The same is true of AI search answers that quote a single figure with confidence: when we traced those citations, they led back to third-party sites, not to the club.

Here is how we handle it for clients:

1. Get the current number from the source. The club’s membership office answers at (239) 596-4797. Ask for the current initiation and annual dues for each category, the social dues that come with the home, and whether any capital or transfer charge applies at purchase.
2. Put it in the contract review. For a buyer, the club’s membership documents belong in the due diligence file alongside the estoppel certificates from the master and neighborhood associations. For a seller, we collect them before listing so a buyer’s agent is not quoting a figure from a portal.
3. Budget the mandatory line first. Social dues come with every home inside the gate. Golf is a separate decision, and it can be made after closing.

How Membership Transfers When an Olde Cypress Home Sells

Sellers ask whether their golf membership goes with the house. Here is exactly what the documents say, and what they leave open.

What the recorded documents settle:

• Social membership passes by covenant. Because Section 14.02 of the master declaration makes each owner a social member “by acquisition of a Parcel,” the buyer becomes a social member at closing automatically. Nothing needs to be assigned.
• There is no equity to sell. Section 14.03 of the same declaration gives owners no equity, voting or ownership interest in the club property, so a seller has no club share to convey or cash out.
• The master association collects a working capital contribution at transfer. Section 8.13 of the 2019 Amended and Restated Declaration for Olde Cypress authorizes the master association to collect a contribution “at the time of the transfer of title of any Parcel,” in an amount “as the Board may from time to time determine.” That is an association charge, not a club charge, and the current amount is not published; the estoppel certificate states it at contract.

What the club describes, but does not document publicly:

• The club’s own summary of the non-equity model lists “Non transferable” as a trait, per its equity and non-equity explainer. Read literally, a golf membership belongs to the member, not the house.

What is unknown from public sources:

• Whether a seller’s Full or Associate Golf membership can be assigned to a buyer, and on what terms.
• Whether any part of a golf initiation is refundable when a member sells and resigns.
• Whether a buyer who wants golf pays a full initiation, a reduced one, or joins a list.
• The current social dues amount and when dues begin for a new owner.

Each of those answers lives in the club’s current membership plan and rules, which the club provides to members and buyers. We get them in writing before a listing goes live, because a buyer’s first question about an Olde Cypress home is usually the club, and a vague answer costs a seller leverage.

The Waitlist: From “How to Get a Spot” to “Naples, the Wait is Over”

For years The Club at Olde Cypress ran with a waitlist. In the club’s February 2024 renovation announcement, republished by Golf Guide, readers were pointed to OldeCypress.com “including how to get a spot on the club’s waitlist.” The club’s Associate Golf page still frames that category as a way to join “without having to spend years on a waitlist.”

By 2026 the message had changed. March 2026 press releases on the Phase I reopening, syndicated through EIN Presswire, described “a limited number of resident and non-resident Full and Associate Golf memberships still available.” The club’s membership page in September 2026 leads with “Naples, the Wait is Over,” adding that “Demand is high following the grand reopening, and a limited number of Resident and Non-Resident memberships are currently available.”

The club publishes no member count, no cap and no current waitlist length. What we can say from its own words is that golf memberships were open to join in September 2026, and that the club expects that window to be limited. If golf is a must for you, ask the membership office where availability stands the week you write an offer, not the week you start looking.

What This Means for Buyers and Sellers

For a buyer, the mandatory social membership is a fixed cost of owning inside the Olde Cypress gate, and the golf decision can wait. For a seller, the club is a selling point that needs documents behind it: a buyer who hears “no assessments, no minimums, golf optional, $16 million clubhouse just finished” wants to see the membership terms in writing.

Thinking about selling? Call Jesse direct at (239) 898-6072, or start with a free valuation of your Olde Cypress home. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.

What Is the Olde Cypress Golf Course Like?

The Olde Cypress golf course is an 18-hole, par 72 P.B. Dye design that opened in 1999, the first P.B. Dye course in Collier County. Olde Cypress plays from 6,711 yards down to 4,132 yards across eight tee options, is known for its island-green 12th hole, and was fully resurfaced in a 2021 renovation.

Architect, Year and Par

The club’s scorecard credits “P.B. Dye, Course Architect” and prints a par of 72, 36 out and 36 in. Golfweek’s September 29, 2021 report on the course renovation says the course was “Built in 1999” and calls it the first course “in the golf hotspot of Collier County designed by P.B. Dye.” The club’s own press materials repeat that distinction.

The club’s golf page describes a layout that “combines characteristics of both links and traditional styles,” with “surprising changes in topography and several holes playing around sculpted bunkers and lakes.” That topography is unusual for flat North Naples, and it is by design: P.B. Dye moved earth to build the elevation you see on holes like No. 4 (“The Alps”) and No. 6 (“Pinnacles & Bluffs”).

The course sits on about 168 acres of golf parcels on the Collier County Property Appraiser 2026 preliminary roll, including the clubhouse and course parcel at 7165 Treeline Drive and the practice range parcel on Logan Boulevard North.

Tee Yardages From the Scorecard

The club’s scorecard image lists eight tee rows, two of them combination tees that borrow holes from the Dye tees.

One club article calls the 6,711-yard set “Tournament”; the scorecard labels it Champ, and we follow the scorecard. The span of 2,579 yards between the back and front tees is what makes the course work for a scratch player and a new golfer on the same afternoon.

Course Rating and Slope by Tee

The Florida State Golf Association is the authorized rating body in Florida. Its club record for The Club at Olde Cypress lists the current USGA Course Rating and Slope Rating for every rated tee. The printed scorecard carries older ratings (for example 73.3 and 144 from the Champ tee), so use the FSGA figures below for handicap purposes.

Men’s tees (FSGA current ratings)

Women’s tees (FSGA current ratings)

Notice that the back nine rates harder than the front from nearly every men’s tee. That tracks with the card: the back nine holds the course’s number one handicap hole (No. 13) and three long par 4s in a row from No. 15 through No. 17.

Hole by Hole From the Champ Tees

Every hole at Olde Cypress has a name on the club’s scorecard. Yardages below are from the Champ tees, with the men’s handicap index.

The scorecard also carries two local rules worth knowing before your first round: free relief from the coquina curbing on Nos. 1 and 3, and flower beds played as ground under repair. It sets a pace of play of four hours for a four-ball.

The Signature Hole: No. 12, “Oasis”

The 12th is an island-green par 3, and it has a story. The club’s golf page calls it a “120 yard par-three island green” that “requires an accurate tee shot,” and asks anyone who makes birdie to “ring our ‘Birdie Bell,’ an Olde Cypress tradition.” The scorecard prints 133 yards from the Champ tee, 116 from the Tournament and Dye tees, and 73 from the Cypress and Calusa tees.

Golf Digest’s feature on golf’s best island greens includes the 12th at Olde Cypress and quotes P.B. Dye on why it exists: “At the time the developer needed a solution for the drainage and pumping from the surrounding agricultural fields … So, I said, ‘Why don’t we build an island green.’ We moved a tremendous amount of earth up and down, not side to side, on that hole. Looking out at all those rock boulders from the tee box, it’s a sight to see.”

That is a useful detail for anyone who owns near it: the island green is part of how the site was engineered to move water off former farmland, not just a showpiece.

The Three Preserve Holes

Part of the Olde Cypress course plays through preserve with no homes along it. The club’s article Discover the Wild Side of Olde Cypress says holes 13 and 14 are “two of the Club’s three preserve holes with no homes around them,” and notes that hole 6 abuts the preserve. The same article and the club’s Keeping Things Wild post describe bobcat, white-tailed deer, river otter and fox squirrel on the property, screech owl boxes, purple martin houses, and an annual daybreak birding tour.

For a buyer, the preserve holes matter in two ways. They shape the round (No. 13, “Islands in the Stream,” is the longest hole on the course at 601 yards from the Champ tee and the number one handicap), and they mean a stretch of the course with no rooflines in view. Conservation lands inside Olde Cypress cannot be altered except for removing exotic plants, under Section 11.04 of the master declaration.

The 2021 Course Renovation

In 2021 the club closed the course for a multi-million-dollar renovation and reopened it in November 2021. Golfweek’s report lists the scope: “All 18 greens, plus the practice green and chipping area were resurfaced with TifEagle Bermuda, the tee boxes were leveled and resurfaced, a new drainage system was installed, and each of the course’s 98 bunkers was refreshed with new edging, contouring and new sand.”

The club’s 2024 recap, republished by Golf Guide, adds that the tee boxes were enlarged and regrassed, that the new subsurface drainage was built “for rapid expulsion of excess water,” and that the driving range gained “new high-performance, artificial turf stations … for use when the grass tees are closed.” The club FAQ describes the work as a “multi-million dollar reimagination of the golf course” paid for without assessments; no dollar figure is published.

In summary, the 2021 work covered:

• TifEagle Bermuda on all 18 greens, the practice green and the chipping area
• Tee boxes enlarged, leveled and regrassed
• A new subsurface drainage system
• All 98 bunkers re-edged, recontoured and refilled with new sand
• Artificial-turf hitting stations on the driving range

Audubon Cooperative Sanctuary Certification

The club states that it “is certified through the Audubon International Cooperative Sanctuary Program for Golf,” in its January 2026 article Olde Cypress Earns Audubon Certification. The article lists the practices behind it: native plantings, buffers along lakes and wetlands, reduced chemical inputs, irrigation efficiency, and habitat for birds and pollinators. This is the club’s own statement; we could not confirm the original certification year from a primary Audubon source, so we do not print one.

Practice Facilities and the Indoor Simulator

The practice program has three parts:

• Driving range with grass tees plus the artificial-turf stations added in 2021 for days when the grass tees are resting. The club does not publish the range length or station count.
• Practice green and chipping area, both resurfaced with TifEagle Bermuda in 2021.
• Full Swing simulator room inside the clubhouse, new with the 2026 renovation, which the club describes as its “newly added indoor golf space.”

Associate Golf members keep practice facility access year-round, including in high season when their course play is limited.

Summer Reciprocal Play at 40+ Clubs

From May 1 through October 31, Olde Cypress members can play elsewhere. The club’s golf page says members “enjoy exclusive access to more than 40 private clubs throughout Southwest Florida” and “can also relax and unwind at a private beach club along the Gulf coast.” A member testimonial on the club’s About Us page names that beach club as The Club at Barefoot Beach.

The golf page names more than 30 of the partner clubs, including Audubon, Bonita Bay, Collier’s Reserve, Esplanade Naples, Fiddler’s Creek, Grandezza, Kensington, Miromar Lakes, Pelican Marsh, Quail Creek, The Quarry, Talis Park, Tiburon Golf Club, TPC Treviso Bay, Vanderbilt, Vineyards and West Bay. Associate Golf members get reciprocal privileges “during the summer months,” per the Associate fact sheet page. The list can change season to season, so confirm it with the golf shop before you plan a summer around it.

Golf Calendar: Leagues and Member Events

The club’s golf events page describes a weekly rhythm in season:

• Ladies’ Day, Tuesdays: 18-hole players in the morning, 9-hole players in the afternoon, with beginner and advanced clinics. The club says it has “one of the largest Ladies groups in Naples.”
• Men’s Day, Wednesdays: ABCD pairings followed by lunch.
• Couples events on designated Sundays in season.
• Interclub teams for men and women that play other clubs monthly.

The recurring member events named on the club’s pages include The Tradition (Member-Member), The Cypress Cup (Member-Guest), the Men’s Club Championship, The Stableford Championship, the Ladies Club Championship at 18 and 9 holes, the Ladies Member-Member and Member-Guest, monthly Couples Mixers, Glow Ball, the Italian Open and a Couples Invitational.

If you are comparing Olde Cypress with other courses, our guide to Naples golf communities lays the clubs side by side. Selling a home on the course? Call Jesse direct at (239) 898-6072 for a free valuation of your Olde Cypress home; golf-view and preserve-view homesites price differently, and we show you by how much on the recorded sales.

What Changed in the $16 Million Clubhouse Renovation?

The Club at Olde Cypress spent about $16 million rebuilding its clubhouse between March 2025 and April 2026, reported by the Business Observer and funded by the Stock family owner with no member assessment. Olde Cypress members got a redesigned bar and dining rooms, a wine room, a golf simulator, new bocce courts and the outdoor Greenside Grille.

Data updated: September 2026

Is Olde Cypress Closed?

No. The Club at Olde Cypress is open. The clubhouse closed for construction starting in March 2025, reopened after Phase I in early March 2026, and finished with the opening of the Greenside Grille and outdoor bar in late April 2026. The golf course stayed open throughout: the club’s renovations page said “Course access will be available throughout the entire project.”

Online comments from 2025 guessing that the course would close were written during construction, before the reopening. If you read one, check the date.

The Timeline, Month by Month

The original plan targeted completion in January 2026. The work finished in two phases, about three months later than that target, and the course never closed.

How Big Is the Clubhouse Now?

Before the renovation the clubhouse was about 34,000 square feet, per Golfweek’s 2021 report and the club’s later press materials. The 2024 plan announcement described “an additional 10,000 square feet of indoor and outdoor space.” The as-built total has not been published, and the county roll will not reflect the new improvements until a later assessment year, so we describe it as about 34,000 square feet plus roughly 10,000 square feet of new indoor and outdoor space.

The 2024 plan broke the addition down as a 2,500 square foot covered first-floor bar and dining area, a new 2,000 square foot kitchen, and an expanded second-floor covered terrace and sun deck with its own bar. That plan also mentioned a “movie theatre experience,” which does not appear in any 2026 description of the finished building, so we treat it as not built.

Who Designed and Built It

The club’s renovations page names the firms:

The Rooms and Venues, Room by Room

Here is what a member walks into today, drawn from the club’s renovations page, the Club + Resort Business Phase I report and the club’s own articles Excellence Expanded, Let’s Get Outside and Games Galore:

• Bar, Members’ Grille Room and Main Dining Room: redesigned around “a dramatic wraparound bar with expanded seating.”
• Cave a Vin: the private dining and wine room, with handmade wine racks under a custom vaulted ceiling. Press releases call it the Private Dining Room.
• Cypress Room: a multipurpose room with a grand piano, used for cards, games and small events.
• Club Room: a lounge with billiards and a fireplace.
• Full Swing simulator room: indoor golf, new with this project.
• Greenside Grille: an outdoor full-service kitchen with a pizza oven, covered and open-air seating over the course, an outdoor bar with central TV viewing, fire pits and lounge seating. Golf Guide’s April 2026 report describes it as a sports bar by day, with casual dinners, live music and dancing in the evening.
• Three bocce courts: new, with lighting and shade structures.

The older descriptions on the club’s social and dining page mention a covered terrace over the 9th hole and putting green and an outdoor Greenside Cafe; the Greenside Grille now fills that role.

Who Paid for It: No Member Assessment

The owner paid. The club’s renovations page and its grand-opening article say the work was funded by Stock Development “with no assessment to the members.” The Business Observer’s April 2, 2025 report put the cost at $16 million, and its March 6, 2026 follow-up repeated that figure at the Phase I reopening.

The club draws the contrast itself in its FAQ: “Unlike member-owned clubs, we don’t have assessments to pay for improvements.” A $16 million project with no member bill is the most concrete example we can point to of what the non-equity model means in dollars.

The County Permit Record

The county side is on the public record too. Collier County’s planning projects layer lists the clubhouse expansion as site development plan amendment PL20230010072 at the club’s Treeline Drive site, shown as “Under Construction” in the Collier County CityView planning projects layer when we checked in September 2026. The county status field often trails the physical work; the club and trade press confirm both phases opened in spring 2026.

New Club Leadership

The renovation came with a leadership change. The club’s longtime general manager retired in 2025 after 24 years, and a new general manager, previously an assistant general manager at another Naples private club, started on August 18, 2025, per a letter from the owner on the club’s site and Gulfshore Business’s appointments column.

What the Renovation Means for Olde Cypress Home Values

We do not attribute a dollar premium to the renovation, because there is not yet enough post-renovation sales history to separate its effect from the rest of the market. What we can say is that in the last 12 months we tracked 26 Olde Cypress closings in the Southwest Florida MLS Matrix, pulled September 26, 2026, and that the buyers touring today see a finished clubhouse instead of a construction fence. For a seller, that is a better story than any since the course reopened in 2021, and it is worth telling with the dates and the documents.

Ready to put a number on it? Call Jesse direct at (239) 898-6072, or request a free valuation of your Olde Cypress home. Buyers can call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.

Tennis, Pickleball, Fitness, Pool and Dining at Olde Cypress

Beyond golf, The Club at Olde Cypress offers four clay tennis courts with stadium seating, two pickleball courts, three lighted bocce courts, a 4,000 square foot fitness center with daily classes, a pool, several dining rooms and the Greenside Grille. Every Olde Cypress homeowner’s mandatory social membership includes tennis, pickleball, fitness and dining.

Data updated: September 2026

Tennis: Four Clay Courts and Stadium Seating

The club’s tennis and racquets page says “Our racquet complex features four pristine clay tennis courts, stadium seating and two pickleball courts.” OpenStreetMap maps four tennis courts and two pickleball courts beside the clubhouse, which matches.

Programming, per the same page:

• Team tennis and daily doubles
• Round robins
• Monthly clinics, lessons and private lessons
• Exhibitions
• Junior development, holiday camps and summer camps
• Adult camps

The program is led by a Director of Racquet Sports certified by the USPTR. Because tennis is part of social membership, a homeowner who never joins for golf still has full use of the courts.

Pickleball: Two Courts

Olde Cypress has two pickleball courts at the racquet complex, per the club’s tennis page. The club does not publish whether they are dedicated courts or lined on another surface, their surface type, or whether they are lighted. If pickleball is your main sport, walk the courts at a busy time in season; two courts is a modest count next to some newer Naples clubs, and our Collier County tennis and pickleball guide compares court counts across the county.

Bocce: Three Lighted Courts

The 2026 renovation added “Three new Bocce Ball Courts, equipped with lighting and shade structures,” per the club’s Games Galore article. The same article describes mahjong groups among the club’s table games.

The 4,000 Square Foot Fitness Center

The club’s fitness page says “The Club’s 4,000 sq ft center is available for members seven days a week, with group fitness classes and personal training sessions offered daily.” It describes strength and cardio equipment and an aerobics room. The program is run by a Director of Wellness with personal trainers on staff.

The Pool

The club lists “our swimming pool” among its amenities in the FAQ on its About Us page, and the membership page refers to “resort-style pool experiences.” The club does not publish the pool’s size, lap lanes or heating. The pool sits with the clubhouse, outside the residential gate.

There is no community pool run by the master association inside the gate; the master association’s site map shows none, so the club pool is the shared pool for Olde Cypress. Exterior changes on a homesite, including a private pool, go through a two-step architectural review: the neighborhood association first, then the master association, under Article X of the master declaration.

Dining Venues

After the renovation, members have five places to eat and drink:

There is no food and beverage minimum, per the club FAQ. The club’s pages describe its member dining as “award-winning” without naming the award, so we note it as the club’s own description.

The Golf Simulator and Club Room

The Full Swing simulator room is open to members as indoor golf, and the Club Room adds billiards and a fireplace. Both came with the 2026 renovation. Neither depends on the weather, which matters in the summer rainy season.

Recurring Social Events

The full event calendar sits behind the member login. The club’s public social and dining events page and membership page name the events that recur each season:

• Welcome Back Party
• Holiday Dinner Dance
• Casino Night
• Live outdoor concerts
• Wine tastings
• Luaus
• “South Beach Style” parties
• Themed dinners, fashion shows and weekly entertainment

The club’s membership page also says it was “Named ‘Best for Club Life’ by LINKS Magazine.” We could not locate the original LINKS article or its year, so we report it as the club’s own statement.

Weddings and Private Events

The club hosts weddings and private events in its indoor and outdoor spaces; see the club’s weddings and special events page for inquiries. Events are booked through the club, not the master association.

Club Hours, Address and Contact

The Club at Olde Cypress is at 7165 Treeline Drive, Naples, FL 34119, phone (239) 596-4797. The club’s directions page routes visitors from I-75 Exit 111 east on Immokalee Road to Logan Boulevard, then north to Treeline Drive, with the club on the right before the residential gate. There is no Olde Cypress Boulevard entrance.

For more on the courts and clubs around this part of Naples, see our Collier County tennis and pickleball guide and our Naples golf communities guide. Buying with racquets in mind? Call Marc at (239) 287-5873; we walk the courts with you before you write an offer. Selling? Call Jesse direct at (239) 898-6072 for a free valuation of your Olde Cypress home.

How The Club at Olde Cypress Compares With Nearby Clubs

Most buyers who look at Olde Cypress also look at a handful of nearby club communities. The biggest difference is structural: Olde Cypress is a non-equity club owned by the Stock family entity, with social membership required and golf optional. Several of its neighbors are member-owned equity clubs, where members vote and can be assessed. The table below uses only what we can source; where a club does not publish a figure, we say so.

Two links between these clubs are worth knowing. Tiburon Golf Club and Vineyards both appear on The Club at Olde Cypress’s summer reciprocal list, per the club’s golf page, so an Olde Cypress golf member can play them from May through October. And because Olde Cypress sells golf to non-residents, an owner elsewhere can join The Club at Olde Cypress for golf without buying inside its gate.

The practical comparison for a buyer comes down to three questions: what membership comes with the house, who pays for capital projects, and what it costs to leave. At Olde Cypress, the answers are social membership only, the owner, and no equity to recover. At an equity club the answers are usually different on all three. We run those numbers for each client from the current documents of each club rather than from web estimates, and as the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate. For more options, see our Naples golf communities guide and our Naples guide.

Weighing Olde Cypress against one of these clubs? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida. Selling here to move to one of them? Call Jesse direct at (239) 898-6072 and start with a free valuation of your Olde Cypress home.

Is Olde Cypress in a Flood Zone? FEMA Zones by Neighborhood

Olde Cypress sits on FEMA flood maps effective May 16, 2012 that place much of the community in Zone AH, a shallow ponding zone, with the rest in shaded or unshaded Zone X. FEMA’s March 20, 2025 preliminary map shows every Olde Cypress PUD home in Zone X, but that map is not effective yet, and Lantana reads differently.

Data updated: September 2026

So the question “is Olde Cypress in a flood zone?” has three honest answers, not one: what the effective map says, what FEMA letters have changed for specific homes and for all of Lantana, and what the new preliminary map proposes. We placed every one of the 548 single-family homes on the 2026 Collier County roll on both maps, footprint by footprint, and read the FEMA letters issued for these streets. Here is what the record shows, neighborhood by neighborhood.

Which FEMA flood maps cover Olde Cypress today?

Four Flood Insurance Rate Map (FIRM) panels cover the community, all for the NFIP community “Collier County, unincorporated areas” (community number 120067), all printed countywide:

The panel list and dates come from FEMA’s National Flood Hazard Layer and match the panel numbers printed on the elevation certificates and FEMA letters for Olde Cypress homes. You may see “February 8, 2024” quoted as Collier County’s current map date. That date belongs to the 2024 coastal revision of other panels; these four inland panels still carry the 2012 “H” suffix in FEMA’s live layer.

Where does flood risk in Olde Cypress come from?

Not the Gulf. Every FEMA determination letter we pulled for an Olde Cypress, Lantana or Da Vinci Estates address names the flooding source as “PONDING/OVERLAND FLOW”: rainfall that collects in low ground and moves across land during an extreme rain event. That is what Zone AH describes. FEMA defines Zone AH as an area of shallow flooding, usually ponding, generally one to three feet deep, with a base flood elevation. It is a Special Flood Hazard Area (SFHA), but it is a very different hazard from the coastal wave zones on the barrier islands.

There is no Zone VE, no Limit of Moderate Wave Action and no Coastal High Hazard Area anywhere in Olde Cypress, per FEMA’s flood hazard layer and Collier County’s GIS services for flood, evacuation and coastal hazard layers. A few lots at the edges of Terramar and Da Vinci Estates, and two buildings at the neighboring Fairway Preserve condominium, touch Zone AE along lake edges.

What the FEMA flood zones mean in plain English

How many Olde Cypress homes touch Zone AH on the effective map?

We did not test a single point per lot. We overlaid each home’s building footprint (Collier County’s 2025 building footprint layer) on FEMA’s effective flood zones. “Fully in the SFHA” means at least 99% of the footprint sits in Zone AH or AE; “partly” means any overlap at all, even a sliver; “Zone X only” means no overlap.

Sources: FEMA’s effective National Flood Hazard Layer, flood zones and base flood elevation lines, overlaid on Collier County’s building footprint and parcel layers, computed September 23, 2026.

Three readings of that table matter more than the totals:

• Many “partly” homes clip only a sliver of Zone AH. A corner of a lanai or garage crossing a zone line counts as “partly” here. A lender’s flood determination and an insurance rating look at the structure, and dozens of these homes hold FEMA letters that removed them (next section).
• Unit One and Tract 9 have the largest share of homes clear of Zone AH on the effective map; Unit Two, Tract 12, Strada Bella and Santorini Villas have the highest share of footprints fully inside it.
• The zone line runs lot to lot. On Olde Cypress Drive, one Unit One home at the 2700 block sits 100% in Zone AH while another a few doors up sits 100% in unshaded Zone X. Never assume a neighbor’s answer is yours.

What are the base flood elevations in Olde Cypress?

A base flood elevation (BFE) is the water surface FEMA expects in the 1% annual chance flood. Every Zone AE and Zone AH polygon in Olde Cypress carries no single static BFE, so the BFE is read from FEMA’s BFE lines. Across the Olde Cypress neighborhoods the nearest lines read 11.5 to 13.5 feet NAVD88 (the table above gives each neighborhood’s range), and the lines crossing the wider envelope around the community, including Fairway Preserve, run up to 14.5 feet. Those are elevations above a national datum, not flood depths.

Lantana: removed by LOMR-F 13-04-6118A, still painted Zone AH

Lantana is the case that confuses automated flood checks. FEMA’s map graphic paints 116 of Lantana’s 122 home footprints fully in Zone AH. But on August 8, 2013, FEMA issued Letter of Map Revision based on Fill 13-04-6118A, which removed Lots 1 through 122, the whole subdivision as platted in Plat Book 52, Pages 47 to 52, from the Special Flood Hazard Area to unshaded Zone X. The letter cites panels 0213H and 0214H and records the lowest lot elevation at 12.9 feet NAVD88.

Why the paint never changed: FEMA lists letters like this as “Not incorporated” into the panel image. The legal status changed; the drawing did not. An elevation certificate on file with Collier County for 7363 Lantana Circle shows the result in practice: Zone X, BFE “NONE”, with the map revised date of 08/08/13.

If you own or are buying in Lantana, the LOMR-F is the document to hand a lender or insurer. The preliminary map, below, is where Lantana’s story changes again.

How many FEMA letters have been issued for Olde Cypress homes?

42 Letters of Map Change (LOMAs and LOMR-Fs) have been issued since 2012 for property on the Olde Cypress, Da Vinci Estates, Lantana and neighboring Fairway Preserve streets, per FEMA’s letter-of-map-change layer. Almost every one reads “Structure removed”: a surveyor showed the home’s lowest adjacent grade sat above the BFE, and FEMA removed that building from the Special Flood Hazard Area.

The grouped letter LOMA 12-04-5230A is a good example of how these read: one Strada Bella lot and three Terramar lots removed to shaded Zone X, against BFEs of 11.5 to 13.8 feet. The lowest adjacent grades recorded on the letters we read run 13.8 to 16.4 feet NAVD88, against BFEs of 11.5 to 13.8 feet. The letters keep coming: the most recent we found, 25-04-6753A, was issued September 29, 2025 for a Lone Pine Lane home with a lowest adjacent grade of 15.2 feet.

A LOMA is address-specific. It covers the building or lot named in the letter and nothing next door.

What do Olde Cypress elevation certificates show?

Collier County holds 65 elevation certificates for homes and structures on these streets (49 of them in Lantana), in its elevation certificate layer. The four we read place finished floors roughly 2.5 to 4 feet above the effective BFE lines:

That pattern, floors a few feet above a shallow-ponding BFE, is consistent with how many LOMAs these streets have received. It is a sample of four, not a survey of every home. The certificate for the specific house is the only number that counts.

What does FEMA’s March 2025 preliminary map show for Olde Cypress?

FEMA issued a new preliminary countywide FIRM for Collier County on March 20, 2025 (panels 12021C0211J through 12021C0214J). Collier County announced that the 90-day appeal period opened August 19, 2026, with the new map targeted to take effect in summer 2027, in its August 2026 release on the proposed Flood Insurance Rate Map. We ran the same footprint test on FEMA’s preliminary National Flood Hazard Layer:

Two conclusions, both conditional on the map becoming effective as issued:

1. For the 366 homes inside the Olde Cypress PUD, the preliminary map draws no Special Flood Hazard Area at all. Today 274 of those footprints touch Zone AH on the 2012 map; on the preliminary map, zero do.
2. Lantana moves the other way. Legally outside the Special Flood Hazard Area today by the 2013 LOMR-F, Lantana would have 72 of its 122 footprints touching newly mapped Zone AH, nearest the 12-foot BFE line. Whether FEMA revalidates the 2013 LOMR-F when the new panels take effect is FEMA’s decision and has not been announced; as a general rule, letters of map change can be superseded when a new map takes effect unless FEMA revalidates them.

A preliminary map is not effective. It can change on appeal, it does not govern insurance or lending today, and the county release gives no neighborhood-level change statistics. Anyone telling you the 2025 map settled the flood question for Olde Cypress is reading a draft.

What should Olde Cypress buyers and sellers do about flood?

Buyers:

1. Ask the seller for the home’s elevation certificate and any LOMA or LOMR-F in writing, early in the contract. Collier County’s elevation certificate archive may already hold one for the address.
2. Search the address on the FEMA Flood Map Service Center for letters of map change. Remember a letter covers the named building or lot only.
3. In Lantana, get a copy of LOMR-F 13-04-6118A and ask your lender how it will treat the lot now and after the preliminary map takes effect.
4. Let the lender make the call. The federal purchase requirement follows the lender’s flood determination for the specific building, not a neighborhood average, a listing remark or this page.
5. Get a flood quote even where it is not required. The ZIP 34119 figures in the insurance section below show what homeowners around you actually pay.

Sellers:

1. Put the elevation certificate and any LOMA in the listing file before the first showing. A buyer’s lender will ask; answering on day one keeps a contract from stalling.
2. If your home partly touches Zone AH on the 2012 map and you have no LOMA, talk to a licensed surveyor about whether one is worth applying for. The 42 letters on these streets show how often the survey supports it.
3. If you own in Lantana, know your LOMR-F story and the preliminary map story, because a well-prepared buyer will ask about both.

Selling an Olde Cypress home? Flood paperwork presented correctly protects your price. Call Jesse direct at (239) 898-6072 or start with a free valuation of your Olde Cypress home. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.

Hurricane Posture: Evacuation Zone, Storm Surge and Wind Code

Olde Cypress sits in Collier County Evacuation Zone E and in Florida’s Category 4 storm surge zone, about 6.7 miles inland from the Gulf beach and east of I-75. It is outside the Coastal High Hazard Area, with no Zone VE. Houses there are designed to a 160 mph ultimate wind speed under the current Florida Building Code.

Data updated: September 2026

Hurricane risk in Southwest Florida comes in three parts: water pushed in from the Gulf (surge), rain that has nowhere to go (the ponding covered above) and wind. Olde Cypress’s position inland of I-75 changes the first one a great deal. It does not change the wind, which is why the build year and the hardening of each house matter so much at resale.

What hurricane evacuation zone is Olde Cypress in?

Zone E. Every one of the 585 home and condo-building points we tested in Olde Cypress, Da Vinci Estates, Lantana and the neighboring Fairway Preserve condominium falls in Evacuation Zone E on Collier County’s hurricane evacuation zone layer. Collier’s system runs from Zone A (closest to the water, ordered out first) through Zone F. Zone E is one of the outer tiers that are called for evacuation only in the larger-surge scenarios. The state’s Collier County evacuation zone and route map from the Florida Division of Emergency Management shows the zones and routes countywide.

What that means in practice: in most storms that prompt evacuation orders for coastal Naples, Olde Cypress is not in the ordered zones. It still means nothing about wind or power, and the county’s orders for each storm are the ones to follow. We did not find Collier’s published definition of which storm triggers Zone E, so we do not state one.

What is the storm surge risk in Olde Cypress?

Sample points across the community (Olde Cypress Drive, Lantana, Terramar and Fairway Preserve) all return the Category 4 storm surge zone on the Florida Division of Emergency Management’s statewide storm surge zones service, built from the Statewide Regional Evacuation Study. In plain terms, the state’s SLOSH modeling shows surge potential at Olde Cypress only in a Category 4 or stronger storm. The state’s Collier County storm surge zone map, dated December 9, 2025, shows the same banding countywide.

The rest of the coastal hazard picture:

• Not in the Coastal High Hazard Area on Collier County’s layer.
• No FEMA Zone VE and no Limit of Moderate Wave Action anywhere in the community.
• About 6.7 miles east of the Vanderbilt Beach shoreline at the same latitude, by our measurement from coordinates.

What design wind speed applies to Olde Cypress homes?

Collier County publishes the Florida Building Code, 8th Edition, ultimate design wind speeds as map layers, and every point we tested in Olde Cypress returned the same values:

Source: Collier County’s Florida Building Code 8th Edition wind load layers, read September 23, 2026. A single-family home is Risk Category II, so 160 mph is the number an engineer uses for new work on an Olde Cypress house today. That is an ultimate design speed for structural calculations, not a promise about any storm.

Is Olde Cypress in a wind-borne debris region?

By our reading of the Florida Building Code, yes. The code defines wind-borne debris regions within the hurricane-prone region as areas where the ultimate design wind speed for Risk Category II buildings is 140 mph or greater. At 160 mph, Olde Cypress clears that threshold by 20 mph. The practical implication: new or replacement windows, sliders and exterior doors on an Olde Cypress home generally have to be impact-rated or protected by approved shutters, and the permit reviewer will check. Confirm the requirement for your specific project with your contractor and Collier County building plan review; we could not retrieve the code text itself from the publisher’s site when we checked, so treat this as our reading, not a quotation.

When were Olde Cypress homes built, and does the code era matter?

It matters for insurance and for inspections. Collier County’s footprint layers let us see when each home first appears in aerial footprint mapping. This is a proxy, so we label it as inferred: the imagery year is an upper bound on when the home was built, and the date that governs code is the permit date.

What we infer from it:

• 155 of the 366 homes inside the Olde Cypress PUD already appear in the 2000 or 2002 footprint layers, so they were likely permitted before the first statewide Florida Building Code took effect in 2002. Unit One and Tract 9 are the oldest sections.
• 211 PUD homes first appear in 2004 or later, in the Florida Building Code era; homes first seen in 2004 straddle the transition.
• Da Vinci Estates is almost entirely a 2004 to 2013 build, and Lantana was built 2013 to 2016, under the 2010 and 2014 editions of the code.

The exact year built for each home is on the Collier County Property Appraiser record, and the permit history is with Collier County. A pre-2002 home is not a weak home; many have been re-roofed and fitted with impact glass since. But an insurer will price the features it can document, so the paperwork, not the age, is what a buyer should chase.

What did Hurricane Irma and Hurricane Ian do near Olde Cypress?

Hurricane Irma, September 10, 2017. Irma made landfall on Marco Island as a Category 3 storm with 115 mph winds. The National Weather Service Miami Hurricane Irma report records 55 mph sustained winds and a 112 mph gust at its North Naples station, a 142 mph gust at Naples Airport, and 9 to 15 inches of rain across inland Collier County. Irma is the dominant flood insurance event for ZIP 34119: 88 of the ZIP’s 124 all-time NFIP claims date from 2017, per FEMA’s OpenFEMA NFIP redacted claims dataset.

Hurricane Ian, September 28, 2022. The National Weather Service Miami Hurricane Ian summary describes surge flooding concentrated south and west of US 41 and along the Gordon and Cocohatchee rivers. Olde Cypress, east of I-75 and about 6.7 miles inland, lies outside that surge-flooded area by our reading of the NWS description. ZIP 34119 logged 13 NFIP claims for 2022.

The Census block group that contains Olde Cypress (along with Da Vinci Estates, Lantana, Fairway Preserve and other neighboring communities) shows only 3 NFIP claims ever in the same OpenFEMA data: two from Irma, one of them on a 1985-built building that cannot be an Olde Cypress home and the other unpaid, and one 2023 claim paid at $0. No Ian claim is coded to that block group.

We looked for news or county reports naming Olde Cypress for structural or flood damage in Irma or Ian and found none. Absence of a report is not proof of no damage: a roof claim on a homeowners policy, a fallen tree or a power outage would not appear in NFIP data. Sellers, answer the disclosure questions about storm damage and repairs completely; buyers, ask for the repair invoices and permits.

How should Olde Cypress owners prepare for a hurricane?

• Know your zone and your plan. Zone E is not ordered out in most storms; decide in advance where you would go if it is.
• Protect openings. Impact glass or approved shutters on every opening is both the code direction for replacements and the feature insurers credit.
• Document the roof. Keep the re-roof permit, the product approval and the date. It drives both your premium and a future buyer’s insurability.
• Photograph the house before the season. A dated photo record speeds any claim.
• Seasonal owners: arrange a hurricane watch service and shutter plan before you leave. the 2019 Amended and Restated Declaration for Olde Cypress disclaims association liability for “any monitoring system, guardhouse, traffic control gate or security service”, so the gate is not a storm plan.

Selling an Olde Cypress home with a newer roof or impact glass? Those upgrades should be priced into your listing, not discovered by the buyer’s inspector. Call Jesse direct at (239) 898-6072 or request a free valuation of your Olde Cypress home.

What Does Home Insurance Cost in Olde Cypress?

No public agency publishes a homeowners or windstorm premium for Olde Cypress, so we will not invent one. Flood insurance is different: FEMA data shows 3,369 NFIP policies in force in ZIP 34119, with a median single-family cost of $1,259 a year, and Collier County’s CRS Class 5 rating trims every NFIP premium.

Data updated: September 2026

Insurance is where Olde Cypress buyers most often get surprised late in a contract, and where sellers lose leverage if a buyer’s quote comes back high. The honest answer has two halves: what the public record shows for flood, and what drives the homeowners and wind premium for a specific house.

What do Olde Cypress-area homeowners pay for flood insurance?

FEMA publishes every National Flood Insurance Program policy in force, with the address removed but the ZIP code and Census geography kept, in its OpenFEMA NFIP redacted policies dataset. We pulled the policies in force as of September 8, 2026 for ZIP 34119, which covers Olde Cypress and much of the surrounding Immokalee Road corridor, and for the Census block group that contains Olde Cypress and its neighbors:

Four things stand out:

1. Most flood policies here are voluntary. Only 468 of 3,369 policies in the ZIP, and 38 of 613 in the block group, carry the mandatory-purchase flag. Owners in Zone X buy flood coverage because the price is modest relative to the risk of an uninsured loss.
2. Zone matters less than it used to. Under FEMA’s Risk Rating 2.0 pricing, the median single-family cost in ZIP 34119 is $1,266 in Zone X, $1,151 in Zone AH and $1,266 in Zone AE. The building’s own characteristics drive the price more than the map color.
3. The median building coverage in the ZIP is $250,000, the NFIP maximum for a single-family building. Contents coverage is separate.
4. These are medians across many homes, not a quote. Your premium depends on your building’s elevation, replacement cost, foundation and the coverage and deductible you choose.

How does Collier County’s CRS Class 5 rating lower flood premiums?

Collier County, unincorporated, participates in FEMA’s Community Rating System at Class 5, which gives a 25% NFIP premium discount for policies in the Special Flood Hazard Area and 10% outside it. The class is recorded in FEMA’s OpenFEMA NFIP Community Status Book and confirmed in Collier County’s 2026 Floodplain Protection newsletter. Every ZIP 34119 policy record in FEMA’s data carries CRS Class 5. The discount applies automatically; you do not apply for it.

What does Collier County require for a new or substantially improved home?

If you are buying an Olde Cypress lot to rebuild, or planning a substantial renovation, Collier County’s freeboard rule sets the lowest floor. Under Collier County Building Bulletin 21, the lowest floor must meet the highest of three standards:

• the base flood elevation plus 1 foot,
• the South Florida Water Management District permit elevation, or
• 18 inches above the crown of the nearest road.

For an Olde Cypress homesite with a 12.5-foot BFE line, the first test alone puts the lowest floor at 13.5 feet NAVD88 or higher; the elevation certificates we read show existing floors at 15.3 to 16.6 feet. A surveyor sets the actual number per lot.

What happened to Citizens Property Insurance in Collier County?

Citizens Property Insurance Corporation, Florida’s state-backed insurer of last resort, has shrunk sharply in Collier County, a trend consistent with homeowners moving to private carriers. Citizens’ county reports show:

Sources: Citizens’ Detail by County report for December 31, 2024 and Detail by County report for August 31, 2026. Statewide, Citizens reported 255,099 policies in force as of September 18, 2026 on its policies in force page. Citizens publishes no ZIP-level or community-level data, so we cannot say how many Olde Cypress homes are insured there.

What it means for you: a buyer in 2026 generally has more private-market options than a buyer in 2023 or 2024, and a home with strong, documented wind features is the one carriers compete for.

Why is there no published homeowners premium for Olde Cypress?

Homeowners and windstorm premiums in Florida are priced per property under each insurer’s filed rates. Two houses on the same Olde Cypress street can price far apart because of roof age, roof-to-wall connections, opening protection, claims history, coverage limits and the hurricane deductible chosen. No agency publishes a community-level premium, and any “average Olde Cypress insurance cost” you find online is an estimate with no public source behind it. The only reliable number is a quote on the specific address, run with that home’s inspection reports.

What drives the homeowners and wind premium on an Olde Cypress home?

The Olde Cypress insurance checklist for buyers and sellers

Before you bind a policy or list a home, gather these:

1. Roof age. The re-roof permit date and material. For many Olde Cypress homes built around 2000, this is the single biggest pricing factor.
2. Wind mitigation inspection. A current Uniform Mitigation Verification Inspection Form (OIR-B1-1802) completed by a qualified inspector. It documents the roof deck attachment, roof-to-wall connection, roof shape, secondary water resistance and opening protection that earn credits.
3. Four-point inspection. Carriers commonly ask for one on older homes: roof, electrical, plumbing and heating and cooling. Pre-2002 homes in Unit One, Tract 9 and parts of Units Two and Three are the likeliest to need it.
4. Impact openings. A list of every window, slider and door with its product approval, or the shutter system and its permit.
5. Flood file. Elevation certificate, any LOMA or LOMR-F, and a current flood quote.
6. Claims history. A seller can pull the property’s insurance claims history report; a clean one reassures the buyer’s carrier.

Sellers: having items 1, 2 and 5 in hand before you list is the simplest way to keep a buyer’s insurance quote from derailing a contract. Call Jesse direct at (239) 898-6072 or start with a free valuation of your Olde Cypress home. Buyers: call Marc at (239) 287-5873 and we will help you request these documents during your inspection period; see how we represent buyers in Southwest Florida.

Which Schools Serve Olde Cypress?

Every single-family home in Olde Cypress, including Da Vinci Estates and Lantana, is zoned for Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026-2027, per the Collier County Public Schools lookup. All three schools earned an A in 2024, 2025 and 2026. The Fairway Preserve condominium next door is zoned to Gulf Coast High instead.

Data updated: September 2026

We did not take the assignment from a listing field, a ZIP code or an old boundary map. We sent real house numbers from every Olde Cypress street to the district’s own live lookup for the 2026-2027 school year, then swept each street for every address record the district holds.

How we confirmed the Olde Cypress school zones

The source is the Collier County Public Schools address lookup for the 2026-2027 school year, queried September 23, 2026 for one real address on every street and then for every record on each street:

453 of 453 address records returned for the single-family streets agree, with no exceptions. Record counts include common-area and utility addresses, so they are a sweep for exceptions, not a home count. The 2026-2027 lookup shows no rezoning against 2025-2026 for any address we tested.

Why some sources say Gulf Coast High for Olde Cypress

Because one part of the name is zoned there. Fairway Preserve at Olde Cypress, the 264-unit condominium on Preserve Circle with its own entrance off Immokalee Road, is zoned to Laurel Oak Elementary, Oakridge Middle and Gulf Coast High; all 11 of its buildings returned Gulf Coast High for both 2025-2026 and 2026-2027. Every single-family street behind the Treeline Drive gate returns Aubrey Rogers High. Any sentence that says “Olde Cypress is zoned for Gulf Coast High” is describing the condominium, not the gated community.

How are Laurel Oak, Oakridge and Aubrey Rogers graded?

The Florida Department of Education publishes school grades on its school grades page. Its workbook could not be downloaded automatically when we checked, so the figures below are taken from the Naples Daily News Collier County school grade database, which republishes the FLDOE data, and from the paper’s July 22, 2026 report on Collier school grades:

The Naples Daily News reported that “Laurel Oak Elementary School is the standout for Collier County, receiving 85% of the total points”, and that Mason Classical Academy led Collier high schools at 76% “with Aubrey Rogers High School close behind with 75%”. Its Laurel Oak Elementary grade history shows an A every year back to 2004-05. The district itself earned an A for the ninth consecutive year, per the Collier County Public Schools announcement of its 2026 grade.

How far are the assigned schools from Olde Cypress?

Distances are road miles from the community entrance at Treeline Drive and Logan Boulevard North, modeled at free-flow speeds with OSRM on OpenStreetMap roads; school-run traffic on Immokalee Road will be slower.

Laurel Oak Elementary and Gulf Coast High share one campus directly across Immokalee Road from the south edge of Olde Cypress, per Collier County’s schools layer. Aubrey Rogers High sits west of I-75 off Veterans Memorial Boulevard, the longest of the three drives.

Charter school options near Olde Cypress

Charter schools are public and tuition-free, but enrollment is by application, not by address:

Grades from the Naples Daily News database of FLDOE data.

Private schools near Olde Cypress

Addresses come from each school’s own website; distances are road miles from the Olde Cypress entrance, free-flow.

For a wider comparison of independent and faith-based options, see our Naples private schools guide.

How to confirm the school for one Olde Cypress address

Run the full street address through the district’s lookup for the year of enrollment, and confirm with the district’s student assignment office before relying on it. Boundaries are reviewed year to year, and the district presents its zone tools as general information, not a guarantee of placement.

Selling in Olde Cypress? An A-rated elementary 1.2 miles away belongs in your marketing, stated correctly. Call Jesse direct at (239) 898-6072 or request a free valuation of your Olde Cypress home. Buying? Call Marc at (239) 287-5873 and see how we represent buyers in Southwest Florida.

Hospitals, ERs and Healthcare Near Olde Cypress

The nearest 24-hour emergency room to Olde Cypress is NCH Emergency Department Northeast at 15420 Collier Boulevard, about 2.4 miles and 5 minutes from the entrance. NCH North Naples Hospital is 4.4 miles away, and the region’s only trauma center, Gulf Coast Medical Center’s Level II center in Fort Myers, is about 25 miles north.

Data updated: September 2026

All distances below are road miles from the Treeline Drive entrance at Logan Boulevard North. Minutes are OSRM free-flow model estimates on OpenStreetMap roads, not measured in-season drive times; an ambulance and a January afternoon on Immokalee Road will both produce different numbers. Facility descriptions are each operator’s own wording.

Hospitals and emergency departments by distance

NCH Emergency Department Northeast: the closest ER

NCH describes its Northeast emergency department as “Collier County’s ONLY freestanding emergency department”. It is open 24 hours, seven days a week, on Collier Boulevard just south of Immokalee Road, 2.4 miles from the Olde Cypress entrance. For most after-hours emergencies it is the fastest door to an emergency physician.

NCH North Naples Hospital: the closest full hospital

NCH North Naples Hospital, on Health Park Boulevard west of I-75, is the closest hospital with inpatient beds and emergency care, about 4.4 miles away. NCH’s emergency services page says the campus is home to two emergency departments, and that its McDonald Pediatric Emergency Department is “the only 24-hour pediatric emergency department in Collier County”. The campus also runs an OB emergency department.

Where is the nearest trauma center to Olde Cypress?

Gulf Coast Medical Center in Fort Myers, about 25.1 miles and 32 modeled minutes north. The Florida Department of Health’s list of Florida trauma centers, updated July 23, 2026, lists Gulf Coast Medical Center as a Level II trauma center in Lee County and lists no Collier County hospital. Lee Health says its trauma center “moved to Gulf Coast Medical Center in early 2022” and is “the only trauma center between Sarasota and Miami”. Older articles that name Lee Memorial Hospital as the regional trauma center predate that move. Which patients are flown or driven there is decided by EMS protocols, which we did not research.

Stroke care near Olde Cypress

Two operators make comprehensive stroke claims. NCH says Baker Hospital downtown hosts Collier County’s comprehensive stroke center, and Physicians Regional says its Pine Ridge hospital, 6.6 miles from Olde Cypress, “is designated as a Comprehensive Stroke Center by the Agency for Healthcare Administration”. Both statements are the operators’ own. In a stroke, call 911 and let EMS choose the destination.

Ambulance, fire rescue and urgent care

The North Collier Fire Control and Rescue District covers Olde Cypress, and Collier County EMS runs ambulances from Medic 42 at 7010 Immokalee Road, co-located with fire Station 42 about a quarter mile west of the community, and Medic 76 at 790 Logan Boulevard North, per the county’s EMS stations layer. Which unit responds first is set by dispatch, not by distance alone.

For walk-in care, NCH’s immediate care page lists its locations; the nearest we could verify is Immediate Care Vanderbilt, 7.1 miles away. We did not list other urgent care chains because we did not verify their locations and hours against first-party pages. Check your insurer’s network from your address.

Buying in Olde Cypress and want to see the drive to NCH Northeast or North Naples Hospital before you commit? Call Marc at (239) 287-5873; how we represent buyers in Southwest Florida explains how we work.

Where Is Olde Cypress? Location, Entrance and Drive Times

Olde Cypress is a gated community in North Naples, ZIP 34119, on the north side of Immokalee Road about 1.3 miles east of I-75. Its only vehicle entrance is on Treeline Drive off Logan Boulevard North, about a quarter mile north of Immokalee Road. From there I-75 Exit 111 is about 1.6 miles away.

Data updated: September 2026

Where is the Olde Cypress entrance?

Treeline Drive at Logan Boulevard North, not Immokalee Road. Collier County’s road centerline layer shows the whole Olde Cypress, Da Vinci Estates and Lantana street network connecting to public roads at one point: Treeline Drive where it meets Logan Boulevard North, about 0.25 mile north of Immokalee Road. There is no Olde Cypress Boulevard, and no Olde Cypress street meets Immokalee Road, even though the community’s southern boundary runs along it.

The 2019 Amended and Restated Declaration for Olde Cypress (recorded at OR Book 5700, Page 1118) spells out the road ownership: Logan Boulevard between Immokalee Road and the community entrance, and Treeline Drive from Logan Boulevard to “the traffic control gate”, are dedicated to the public; the rest of Treeline Drive belongs to the master association. The staffed gatehouse sits on Treeline Drive roughly 0.12 mile east of Logan Boulevard, with the guard house at (239) 592-5381 printed on the master association’s Olde Cypress neighborhood site map.

The club’s own directions page gives the approach: from I-75 Exit 111, east on Immokalee Road “a mile and a quarter” to Logan Boulevard, then north, with the club on the right. The clubhouse at 7165 Treeline Drive sits west of the gate, outside it.

Fairway Preserve at Olde Cypress, the 264-unit condominium, is reached separately, from Immokalee Road by way of Dancing Wind Lane, with no road link to Treeline Drive.

How far is Olde Cypress from I-75, the airports, the beach and downtown?

Road miles from the Treeline Drive entrance, with minutes modeled by OSRM on OpenStreetMap roads at free-flow speeds. These are estimates without traffic; in season, Immokalee Road, I-75 and US 41 run slower, so round up.

Routes and times from the OSRM routing engine, run September 23 and 26, 2026, from the Treeline Drive and Logan Boulevard North intersection.

How much does a home deep inside Olde Cypress add?

Olde Cypress covers about 540 acres by the master association’s count, so the far end of the community adds real distance. From 2757 Olde Cypress Drive, near the north end, it is about 0.7 mile and 3 minutes to the entrance and 2.4 miles and about 6 minutes to I-75 Exit 111. The Strada Bella area sits roughly 1.4 road miles inside the entrance. Add up to about 1.4 miles to any figure in the table for a home at the back of the community.

What is the drive like in season?

Honest answer: Immokalee Road is the constraint. Collier County’s own capacity reports rate the Immokalee Road segment in front of Olde Cypress as over capacity at the evening peak (details in the “What Is Being Built” section below). The advantages of the location are that I-75 is under two miles from the entrance, Logan Boulevard gives a second way south toward Vanderbilt Beach Road, and daily errands at Sprouts and Tree Farm Plaza do not require the interstate at all.

Buying and want to test the commute at rush hour before you write an offer? Call Marc at (239) 287-5873, and see how we represent buyers in Southwest Florida.

Shopping, Beaches, Parks and Daily Life Near Olde Cypress

Daily errands from Olde Cypress are short: Sprouts Farmers Market is 0.6 mile from the entrance, two Publix stores are about 2.2 miles, and Tree Farm Plaza is 2.4 miles. Whole Foods at Mercato is 6.6 miles, Delnor-Wiggins Pass State Park 7.0 miles, and North Collier Regional Park 3.6 miles, all measured by road.

Data updated: September 2026

Distances in this section are road miles from the Treeline Drive entrance at Logan Boulevard North, with free-flow minutes modeled by OSRM on OpenStreetMap roads, run September 26, 2026. Add up to about 1.4 miles for a home at the far end of the community.

Where do Olde Cypress residents buy groceries?

Sprouts sits at the Logan Boulevard and Immokalee Road corner, so the closest full grocery store is on the way out of the gate without touching Immokalee Road traffic east or west.

Tree Farm Plaza and the Immokalee and Collier node

At the northwest corner of Immokalee Road and Collier Boulevard, about 2.4 miles east, Tree Farm Plaza (8710 Addison Place Dr and 15405 Collier Blvd) added more than 25,000 square feet of shops and restaurants, with tenants including Chipotle, Cava, Riko’s Pizza, Jersey Mike’s, Nothing Bundt Cakes and Club Pilates, per Gulfshore Business’s report on Tree Farm Plaza. Across the intersection, Founders Square fills the southeast corner. This node is also where NCH’s Northeast emergency department sits. (Tree Farm Road itself is a different road, south of Immokalee Road and east of Collier Boulevard.)

Mercato, Waterside Shops and the outlets

Mercato is the nearest dining and shopping district, anchored by Whole Foods. Waterside Shops sits on US 41 (Tamiami Trail North). For outlet shopping, Miromar in Estero is the closest; there is no outlet mall in Naples itself. For where to eat across the county, see our Collier County restaurants guide.

Which beaches are closest to Olde Cypress, and where do you park?

The rule that matters for owners: Collier County’s beach parking information page says “Collier County residents are eligible for a free beach parking permit upon proof of residency”, and without it the county charges a $10 pay-to-park fee at beach parks such as Vanderbilt and Barefoot Beach. Delnor-Wiggins is a state park with its own $6 per vehicle fee. Delnor-Wiggins also has a boat ramp and a kayak launch into Water Turkey Bay; the state park notes temporary restrooms and no drinking water effective April 18, 2025. For lot-by-lot parking detail, see our Naples beach parking guide.

Parks and preserves near Olde Cypress

North Collier Regional Park is the big one: Collier’s aquatic parks page describes Sun-N-Fun Lagoon’s “one million gallons of water fun”, and the Golisano Children’s Museum of Naples sits next door at 15080 Livingston Road. See our Collier County parks guide for the full list.

Alligator Flag Preserve is the surprise. This Conservation Collier preserve at 7875 Immokalee Road sits on the south edge of the Olde Cypress PUD, across Immokalee Road from Gulf Coast High School. Collier County’s trails layer maps about half a mile of public dirt hiking trail there, and Greater Naples Leadership describes pine-carpeted paths and 78 plant species, four of them state-protected, in its write-up of a Conservation Collier volunteer day. There is no parking lot, so it is a walk-in or bike-in preserve. More preserves like it are in our Conservation Collier preserves guide.

Arts, sports and entertainment near Olde Cypress

The county-owned sports complex on City Gate Boulevard North describes itself as having “nine full-sized fields, including the 3,500-seat stadium, and six sand volleyball courts”.

What is daily life like inside the Olde Cypress gate?

The amenities are the club’s, west of the gate: a P.B. Dye 18-hole course, four clay tennis courts and two pickleball courts, a 4,000-square-foot fitness center and a clubhouse reopened after a $16 million renovation (other sections of this page cover the club in depth). Inside the gate, the 2019 Amended and Restated Declaration for Olde Cypress reserves easements for walkways and bicycle paths, allows golf carts on community streets under master association rules, bars boats (other than maintenance) and swimming or wading in the lakes, and requires vehicles to be garaged overnight rather than parked on the streets. The club describes three “preserve holes with no homes around them” and wildlife from bobcats and river otters to screech owls on its Olde Cypress wildlife post.

Selling? Buyers pay for a location where the grocery store is under a mile and the beach is 15 minutes; your listing should say so precisely. Call Jesse direct at (239) 898-6072 or request a free valuation of your Olde Cypress home. Buying? Call Marc at (239) 287-5873 and see how we represent buyers in Southwest Florida.

What Is Being Built Near Olde Cypress?

The biggest changes near Olde Cypress are roads: Collier County rates the Immokalee Road segment in front of the community as over capacity, and the fixes are the Vanderbilt Beach Road Extension (Phase I opened July 2026), a diverging diamond at I-75 Exit 111, and a $20.5 million Immokalee Road project programmed for fiscal 2028.

Data updated: September 2026

Olde Cypress itself is built out. What changes around it will shape commutes, noise and resale for years, so we read the county’s own capacity reports, the regional transportation program, and the site plans on file within about two miles. Here is what is real, what is funded and what is still unknown.

How congested is Immokalee Road in front of Olde Cypress?

Every year Collier County grades its road links in the Annual Update and Inventory Report (AUIR). The Immokalee Road link from Logan Boulevard to Collier Boulevard, the stretch along Olde Cypress’s southern edge, is officially deficient:

In the 2025 report the Immokalee Road link carries a service volume of 3,200 vehicles in the peak direction against 2,910 counted plus 400 already committed to approved projects. The county’s stated remedy in both years is to “continue to monitor”, pursue a detailed capacity and operational analysis, and anticipate the Vanderbilt Beach Road Extension to redistribute traffic. Logan Boulevard is a two-lane undivided road, and we found no widening of the segment north of Vanderbilt Beach Road in the county’s program.

Vanderbilt Beach Road Extension: Phase I is open

The county’s named relief valve for Immokalee Road is a parallel east-west route. Collier County reports that Vanderbilt Beach Road Extension Phase I, 7 miles from Collier Boulevard to 16th Street NE, six lanes divided to Wilson Boulevard, reached substantial completion on June 12, 2026, with a ribbon cutting on July 1, 2026. Phase II, 16th Street NE to Everglades Boulevard, was in the final stages of design, with construction possibly starting in early 2027. Its effect on the Immokalee Road counts will show up in future AUIRs; we will not predict it.

I-75 Exit 111: a diverging diamond interchange

The Florida Department of Transportation plans to rebuild the I-75 and Immokalee Road interchange, about 1.3 miles west of Olde Cypress, as a diverging diamond, inside its larger I-75 Golden Gate Parkway to Alico Road project: 21 miles with express lanes, auxiliary lanes and about 16 miles of noise walls. FDOT held public information sessions on August 31, September 1 (at North Collier Regional Park) and September 2, 2026, and WGCU reported on September 20, 2026 that construction could begin within the next year. Project documents disagree on the exact start, so treat 2027 as the earliest realistic construction year for the interchange. Expect lane shifts at Exit 111 during construction; the noise walls follow the interstate, well west of the community.

The $20.5 million Immokalee Road project and the Livingston flyover

• Immokalee Road, Livingston Road to Logan Boulevard. The Collier MPO’s FY2027 to 2031 Transportation Improvement Program, adopted June 12, 2026, programs $20,498,000 of construction in FY2028 on this 2.1-mile segment west of Olde Cypress, managed by Collier County with state and local funds. The program sheet labels the work type “pave shoulders”; the full scope is not spelled out there.
• Livingston Road flyover. On July 28, 2026 the county commission approved a $7.59 million design contract for a four-lane Livingston Road flyover over Immokalee Road, with design taking about 30 months and construction to follow the I-75 interchange, per Gulfshore Business’s report on the flyover design contract. It is about 3 miles west of Olde Cypress, on the same corridor.
• Vanderbilt Beach Road at Logan Boulevard. Intersection improvements (mast arms and dual westbound left turns) were advertised for bid by Collier County in late 2024, per the Collier Clerk’s legal notice for Bid 25-8327, about 1.6 miles south on the community’s Logan Boulevard route.

What is being built across Immokalee Road from Olde Cypress?

• The Karlyn, 7576 Immokalee Road, on the south side east of Logan Boulevard: a three-story, 159-unit apartment community on about 9 acres. Land clearing began in November 2024 and completion was expected in April 2026, per Gulfshore Business’s report on The Karlyn. We did not confirm a certificate of occupancy.
• Ivy Medical Center, a planned medical office on a 3.87-acre vacant commercial parcel on the south side of Immokalee Road, rezoned to C-1 by Ordinance 23-09 on January 24, 2023. Its site development plan was under county review, with resubmittal requested, on Collier County’s CityView projects layer when we checked.
• The Laurel Oak Elementary and Gulf Coast High campus, about 65 acres of School District land at 7802 Immokalee Road, directly across from the community.

The Tree Farm and Founders Square node at Collier Boulevard

About three quarters of a mile to a mile east, the Immokalee Road and Collier Boulevard intersection is filling in fast:

• Tree Farm MPUD (northwest corner): a 2023 amendment raised its approved units from 460 to 580, per Naples Press. It includes Tree Farm Plaza retail, Tree Farm apartments, and Las Palmas, which Habitat for Humanity of Collier County describes on its Las Palmas community page as 210 single-story condominium homes in 13 buildings on about 17 acres, under construction.
• Founders Square (southeast corner): the developer reported the center “nearing full capacity” in May 2025 on its Founders Square tenant announcement, with additions including Roadies Pit Stop and Panda Express.
• NCH Emergency Department Northeast anchors the healthcare side of the node, 2.4 miles from the Olde Cypress entrance.

For buyers this node is a convenience; for traffic it is part of why the Immokalee Road link is over capacity.

What is on the land next door to Olde Cypress?

The largest open question sits directly east. The North Collier Fire Control and Rescue District owns about 19 acres of agriculturally zoned land immediately east of the community (two parcels of about 11.1 and 8.0 acres, one of them at 810 Nursery Lane), per Collier County parcel records on the 2026 preliminary roll. Its intended use is unknown. We found no public plan, petition or board document for it. The district did buy new administrative headquarters condominiums at 1110 Pine Ridge Road for $3.495 million on August 4, 2026, and is converting Station 45 to a training center, per Gulfshore Business’s report on the North Collier Fire headquarters purchase; neither item names the Nursery Lane land. Any change of use would need county approvals with public notice, so watch the county’s hearing notices.

A small Nursery Lane and Rose Boulevard enclave of agricultural and commercial zoning also sits between Olde Cypress and Esplanade, and two undeveloped agricultural parcels (about 5.0 and 3.1 acres) sit at 2150 and 2170 Logan Boulevard North, south of Immokalee Road. We found no pending rezoning on any of them in 2024 to 2026 notices.

Who are Olde Cypress’s neighbors?

A naming note: Cypress Woods Golf and Country Club, about a mile west, is a different community.

Which public services cover Olde Cypress?

No new county park or library is planned within two miles in any 2025 or 2026 county document we found.

What this means if you own or are buying in Olde Cypress

• Short term, expect construction on the corridor, most visibly at I-75 Exit 111 once the diverging diamond starts, and eventually at Livingston Road.
• Longer term, the county is adding capacity around the community, not through it. Olde Cypress’s single entrance on Logan Boulevard keeps community streets free of through traffic.
• The one unknown next door is the fire district’s 19 acres to the east. If a petition is filed, it will appear in the Collier Clerk’s public hearing notices.

As the leaders of Domain Realty Group, our team has closed over $2.5 billion in real estate, and the pipeline next to a community is one of the first things we check for a seller’s pricing and a buyer’s due diligence. Selling an Olde Cypress home? Call Jesse direct at (239) 898-6072 or request a free valuation of your Olde Cypress home. Buying? Call Marc at (239) 287-5873 and see how we represent buyers in Southwest Florida.

McGreevy and Comisar have been Top 1% Real Estate Agents Nationally Since 2008, and the flood, school and location records in this section are the same ones we hand to Olde Cypress buyers and sellers.

Olde Cypress vs The Vineyards: Which North Naples Golf Community Fits You?

Olde Cypress and The Vineyards are both gated North Naples golf communities with privately owned, non-equity clubs and no CDD, but they are built for different buyers. Olde Cypress is 548 single-family homes around one 18-hole course with mandatory social membership; The Vineyards is roughly 2,800 homes of every type around 36 holes with optional membership.

Data updated: September 2026

The two communities share ZIP 34119, and they come up together because Google itself pairs them: The Vineyards is the first club in the search engine’s own “people also search for” set for Olde Cypress. On paper they look alike. Both clubs are owned by the family that developed the community rather than by the members, both say they do not assess members, and neither community carries a Community Development District. Under that surface the two are close to opposites. One is a single-product, single-course, single-gate neighborhood of detached homes that sells in weeks. The other is a small town of 38 neighborhoods, from villas to custom estates, around two rebuilt golf courses, where the club is a choice rather than a condition of ownership.

This section compares them on the records that decide a purchase: what sold, how fast, what the club requires of an owner, what it costs to find out, and what the flood maps and school zones say. Every Olde Cypress figure below is sourced to its record; The Vineyards figures come from our Vineyards guide, where each is cited to its own primary source.

The Decision Table

The sale figures for the two communities come from separate Matrix pulls with different end dates (September 26, 2026 for Olde Cypress, August 10, 2026 for The Vineyards), so read them as the same kind of measurement taken about seven weeks apart, not as one snapshot. The Vineyards median also blends condominiums, coach homes and villas with houses, while every Olde Cypress sale in the window was a single-family home. That product mix explains much of the $380,000 gap between the two medians.

Price and Pace: Why Olde Cypress Sells in 29 Days

The sharpest difference in the table is speed. In the last 12 months we tracked 26 Olde Cypress closings in the Southwest Florida MLS Matrix, pulled September 26, 2026, and the median home went under contract after 29 days on market and sold at 97.52% of its final list price. The Vineyards took a median 74 days on 153 sales and closed at 94.6% of list. Three things drive that gap, and all three are visible in the public record.

First, supply. Olde Cypress has 548 homes and one product type, so there are rarely more than a handful of competing listings at a time, and a buyer who wants this gate, this course and a detached house has very few alternatives inside it. The Vineyards has five times the homes and every product type, so a buyer there can nearly always find a second or third option in a different neighborhood.

Second, the club structure at purchase. At Olde Cypress the social membership comes with the deed under Section 14.02 of the 2019 Amended and Restated Declaration for Olde Cypress, and golf is an optional purchase on top. Buyers self-select before they tour. At The Vineyards membership is separate from the house, so the house competes on its own merits and the club decision can come later.

Third, age and renovation. The Olde Cypress clubhouse reopened in March 2026 after a renovation that the Business Observer reported at $16 million, and the club says on its renovations page that Stock Development funded it with no assessment to the members. The Vineyards rebuilt both of its golf courses in 2023 and 2024. Both clubs have recently reinvested, so neither is selling a tired amenity.

The county record points the same way. The Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) show 24 Olde Cypress single-family sales in the 12 months to the file date at a median recorded price of $1,142,500 (even n, so the mean of the middle pair). That is a different record from the MLS, covering a different window, and the two are not averaged or mixed here.

The Club Question: Mandatory Social Versus Optional Membership

Both clubs call themselves non-equity and privately owned, and both use that structure the same way: the owner, not the members, funds capital projects. The Club at Olde Cypress says on its About Us page that it has no member assessments and no food and beverage minimum. Our Vineyards guide records the same two statements from Vineyards Country Club.

The difference is what an owner must buy. Every Olde Cypress owner “automatically becomes a social member of The Club at Olde Cypress” by acquiring a parcel, with dues “as promulgated by The Club … from time to time,” and gains “no equity, voting or ownership interest” in the club property (Sections 14.02 and 14.03 of the recorded 2019 Declaration, Collier Clerk Instrument 5796524, OR 5700 PG 1118). The club’s membership page repeats that social membership is mandatory for residents who do not hold a higher category, and that Full Golf and Associate Golf are open to residents and non-residents. A Vineyards owner can buy a house and never join.

The second difference is price disclosure. Vineyards Country Club publishes its 2026 initiation and dues schedule, which our Vineyards guide walks through. The Club at Olde Cypress publishes no initiation or dues figure on any public page; its fact sheet and golf guide sit behind a lead form. Third-party figures circulating online for Olde Cypress golf initiation run from roughly $45,000 to $175,000, they conflict with each other, and none is published by the club. The current number comes from the club’s membership office at (239) 596-4797, and it belongs in the contract review before a buyer is committed. We treat that as a disclosure item on every Olde Cypress purchase or sale we work.

Golf: One P.B. Dye Course Versus 36 Rebuilt Holes

Olde Cypress has one course: 18 holes, par 72, designed by P.B. Dye and opened in 1999, reported by Golfweek in 2021 as the first P.B. Dye design in Collier County. The club scorecard runs from 6,711 yards at the Champ tees to 4,132 yards at the Calusa tees, and the current men’s Champion rating is 73.4 with a slope of 139 on the Florida State Golf Association club record. Its signature hole is the 12th, an island-green par 3. All 18 greens were resurfaced with TifEagle Bermuda in 2021, when all 98 bunkers were also rebuilt. Members may use their own carts for an annual fee the club gives as $1,950 in its post Five Things to Know About Naples Private Golf and Country Clubs.

The Vineyards has two 18-hole courses, North and South, rebuilt by Kipp Schulties between 2023 and 2024, per our Vineyards guide. For a golfer who plays four or five times a week and wants variety, 36 holes is the stronger case. For a golfer who wants tee times on one well-kept course, with the club stating “tee times are readily available” for Full Golf members, the single course is enough, and the club says about 60% of members use their own carts.

Gate, Location and Daily Logistics

Olde Cypress has exactly one way in for its 548 homes: Treeline Dr at Logan Blvd N, where the master association’s official neighborhood site map places a staffed gatehouse (guard house (239) 592-5381). The clubhouse, courts, pool and range sit west of that gate, which is why the club can sell memberships to non-residents without opening the neighborhood. From the entrance it is 1.6 road miles to I-75 Exit 111 and 2.4 miles to NCH Emergency Department Northeast, open 24 hours, on the free-flow OSRM routing model. There is no Olde Cypress Blvd entrance and no gate on Immokalee Rd.

The Vineyards borders I-75 at Exit 107 (Pine Ridge Rd), where FDOT opened a diverging diamond interchange in June 2026, and Physicians Regional Pine Ridge sits about 1.2 road miles from the club, per our Vineyards guide. The Vineyards is the Pine Ridge corridor community of the two. Olde Cypress is farther north on the Immokalee Rd corridor, 14.5 road miles from Fifth Avenue South downtown on the same OSRM model.

Schools and Flood Maps

Every single-family street in Olde Cypress, including Lantana and Da Vinci Estates, is zoned for the 2026 to 2027 school year to Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High, per the Collier County Public Schools address lookup; 453 of 453 address records agreed. All three earned an A in each of the 2024, 2025 and 2026 state grade releases, and Laurel Oak posted the top elementary score in Collier in 2026 at 85% of points, as reported in the Naples Daily News July 22, 2026 school grades report, which republishes Florida Department of Education data. The Vineyards’ reported feeder pattern (Vineyards Elementary, Oakridge Middle, Gulf Coast High) shares Oakridge Middle; our Vineyards guide recommends confirming any Vineyards address in the district lookup.

On flood, both communities are mixed, and both are in transition. The effective Olde Cypress FIRM panels date from May 16, 2012; on them, 141 of the 366 homes inside the Olde Cypress PUD have building footprints wholly in Zone AH (shallow ponding) and 133 partly, based on footprints overlaid on the FEMA National Flood Hazard Layer. On FEMA’s preliminary March 2025 flood maps, all 366 fall in Zone X. Those maps are not effective yet: Collier County opened the 90-day appeal period on August 19, 2026, with the new map targeted for summer 2027. Our Vineyards guide measures about 36% of the Vineyards census area in a Special Flood Hazard Area on the current maps. In both communities a LOMA or LOMR-F is address-specific, and lenders decide flood insurance requirements building by building.

Who Should Choose Olde Cypress

• You want a detached home and a golf club, and nothing else in the product mix. Every one of the 548 homes is single-family, and 55 of them are paired villas; there are no condominiums or coach homes behind the gate.
• You want a club where the social layer is built in. Mandatory social membership means every neighbor is also a club member, which gives the clubhouse a resident core.
• You like one course and easy tee times more than 36 holes. The P.B. Dye course, its island-green 12th and its three preserve holes are the golf product.
• You value a quiet, single-gate street network. One gate serves all nine neighborhoods, and the clubhouse traffic stays outside it.
• You want fast resale. A 29-day median and a 97.52% sold-to-list ratio on 26 sales point to a market where well-priced homes move.
• You want the Laurel Oak, Oakridge and Aubrey Rogers assignment that covers every single-family street.

Who Should Choose The Vineyards

• You want choice of product. Villas, condominiums, coach homes, single-family homes and custom estates sit inside one community, and the median sale was $725,000 on 153 sales.
• You want 36 holes, both courses newly rebuilt.
• You want the club to be optional, or you want to join later on a published schedule rather than at closing.
• You want published club pricing before you offer. The Vineyards posts its 2026 initiation and dues; Olde Cypress does not.
• You want the Pine Ridge corridor, with I-75 Exit 107 and a hospital a little over a mile from the club.

Read the full picture in our Vineyards guide before you decide, and bring the club question to the first showing rather than the last.

Own in Olde Cypress and weighing a move? Call Jesse direct at (239) 898-6072 or request a free valuation of your Olde Cypress home. Choosing between the two as a buyer? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.

How Does Olde Cypress Compare With Other North Naples Communities?

Among seven North Naples club communities we benchmarked, Olde Cypress sits in the middle on price and at the top on speed. Its $1,105,000 median sale (26 sales) is below Tiburon, Mediterra and Quail West and above Heritage Bay, Sterling Oaks and The Vineyards, and its 29-day median time on market is the fastest of the seven.

Data updated: September 2026

Each figure below comes from a Southwest Florida MLS Matrix pull published in our own community guides. The pulls were run on different dates between July 1 and September 26, 2026, so the table compares seven snapshots taken within about twelve weeks of one another, not one simultaneous measurement. Read the pull date column before reading any row against another.

The Seven-Community Benchmark

Source: Southwest Florida MLS Matrix, closed sales in the trailing 12 months ending on each pull date, as published in our community guides. Every sample here is modest, from 26 to 153 sales, and a few closings can move a median. Sterling Oaks (September 23), Heritage Bay (September 24) and Olde Cypress (September 26, 2026) were pulled within four days of one another, so those three are the cleanest comparisons in the table. Product mix differs by community: Olde Cypress sold only single-family homes in its window, while The Vineyards and Sterling Oaks sell a mix of houses and condominiums, which pulls their medians down.

What the Benchmark Says, in Plain English

• Olde Cypress sells fastest. Its 29-day median is about half of Sterling Oaks at 56 days, less than half the next-quickest golf community in the table (Quail West at 73 days) and about a third of Tiburon, Heritage Bay and Mediterra at 86 to 91 days.
• Olde Cypress sells closest to list. Its 97.52% median sold-to-list is the highest of the seven, a hair ahead of Sterling Oaks at 97.26%, and three to five and a half points above the equity-club communities.
• It is the mid-priced private golf club in this set. At $1,105,000, the median Olde Cypress home costs about 60% of the median Tiburon home ($1,850,000), about half the median Mediterra home ($2,125,000) and a little over a quarter of the median Quail West home ($3,975,000).
• Its closest price neighbors are not golf clubs. Heritage Bay ($482,500) and Sterling Oaks ($485,000) sell at less than half the Olde Cypress median, largely because both sell condominiums and Sterling Oaks has no golf course.
• The club model sorts the set. Quail West and Mediterra are member-owned equity clubs: members own the club and fund its capital needs. Olde Cypress and The Vineyards are privately owned non-equity clubs, where the owning company funds improvements and members hold no ownership stake. Neither model is better in the abstract. They are different bets, and a buyer should know which one they are making.
• CDDs are uneven across the set. Olde Cypress has none (proved against the Collier County CDD map layer and the 2025 tax bill, which carries only a solid waste charge). The Vineyards, Sterling Oaks and Quail West have none either, per our guides. Mediterra appears on the state’s official special district list with its own CDD, as our Mediterra guide and our Sterling Oaks guide record.

Olde Cypress Against Tiburon

Tiburon is the price step up: a $1,850,000 median on 32 sales pulled September 18, 2026, with a median 86 days on market and a 93.84% sold-to-list ratio. Tiburon homes took almost three times as long to sell as Olde Cypress homes and closed about 3.7 points further below list. For a seller, that gap is a reminder that Olde Cypress buyers are not waiting for price cuts; for a buyer, it means Olde Cypress rarely offers a long negotiation. Read our Tiburon guide for its club structure and fees.

Olde Cypress Against Heritage Bay

Heritage Bay, whose PUD lies about 0.86 miles east of Olde Cypress (straight line) along Immokalee Rd, sold 70 homes at a median $482,500 (pulled September 24, 2026), with a median 86 days on market and a 95.71% sold-to-list ratio. It is the high-volume, lower-price golf option on the same corridor. A buyer choosing between the two is choosing between a larger, faster-turning Olde Cypress house market and a broader Heritage Bay market with more entry points. Our Heritage Bay guide covers its association, club and product mix.

Olde Cypress Against Sterling Oaks

Sterling Oaks is the closest comparison in time: 27 sales, a $485,000 median, 56 days on market and a 97.26% sold-to-list ratio, from a September 23, 2026 pull, three days before the Olde Cypress pull. It is a tennis community with 12 Har-Tru clay courts and no golf course, near US 41. The sold-to-list ratios are nearly identical, which says both communities price realistically; the price gap is the golf course and the product mix. See our Sterling Oaks guide.

Olde Cypress Against Quail West and Mediterra

Quail West (42 sales, $3,975,000 median, 73 days, 94.5%, pulled July 15, 2026) and Mediterra (58 sales, $2,125,000 median, 91 days, 91.9%, pulled July 1, 2026) are the luxury equity clubs of North Naples. Both pulls are about ten to twelve weeks older than the Olde Cypress pull, so the comparison carries that lag. The structural contrast is the club: members own Quail West and Mediterra, while Olde Cypress members own nothing in the club and pay no assessments. A buyer who wants an ownership stake in the club, and accepts the capital calls that can come with it, is a Quail West or Mediterra buyer. A buyer who wants the owner to carry the capital is an Olde Cypress buyer. Read our Quail West guide and our Mediterra guide.

Olde Cypress Against The Vineyards

The Vineyards (153 sales, $725,000, 74 days, 94.6%) is the full comparison in the section above. In one line: The Vineyards is the broader, optional-club market; Olde Cypress is the smaller, single-family, built-in-club market that sells about two and a half times faster.

Where to Go Next

Our Naples golf communities guide lays out every Naples golf club side by side, including course counts and club models, and our Naples guide puts all of these communities in the context of the city. If you are also choosing an agent, we compared the field on the public record in the best real estate agents in Naples, compared on the public record.

Selling in Olde Cypress and wondering how your home sits against these neighbors? Call Jesse direct at (239) 898-6072, or start with a free valuation of your Olde Cypress home. Comparing North Naples golf communities as a buyer? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.

The Honest Pros and Cons of Olde Cypress

Olde Cypress’s strengths are fast, near-list sales (29 days, 97.52%), no CDD, a non-equity club that funded a $16 million renovation without assessing members, one staffed gate, A-rated assigned schools and a short run to I-75. Its trade-offs are unpublished club costs, a privately owned club, Immokalee Rd congestion, older pre-code homes and flood mapping in transition.

Data updated: September 2026

Every item on both lists is sourced to a record. None is marketing, and none is a guess; where a figure is not published, we say so.

The Pros

• Golf-club living at a mid-market price. The median Olde Cypress sale was $1,105,000 on 26 closings, at a median $472.75 per square foot of living area (Southwest Florida MLS Matrix, pulled September 26, 2026). On the September 23, 2026 pull published in our Sterling Oaks guide, Audubon Country Club’s median ran $555.48 per square foot on 24 sales. Of the seven communities we benchmarked, three had lower medians (Heritage Bay, Sterling Oaks and The Vineyards) and three had higher ones (Tiburon, Mediterra and Quail West).
• Homes sell fast. A median 29 days on market was the fastest of the seven North Naples communities we benchmarked.
• Homes sell close to list. A 97.52% median sold-to-list ratio on 26 sales, the highest of the seven.
• No CDD. No Olde Cypress district appears in the Collier County CDD map layer or on the state’s list of dissolved special districts, and the Collier County Tax Collector 2025 bill for a Lone Pine Ln home carries one non-ad valorem line, a $261.91 garbage charge. There is no bond debt on the tax bill.
• A non-equity club with no assessments. The club states on its About Us page that it has no member assessments and no food and beverage minimum. Its equity versus non-equity explainer calls Olde Cypress “one of the few non-equity clubs in Naples.”
• A $16 million clubhouse renovation the members did not pay for. The Business Observer reported the renovation at $16 million; Phase I reopened in early March 2026 and the Greenside Grille and outdoor bar opened in late April 2026, per Golf Guide’s April 28, 2026 report. The club’s renovations page says Stock Development funded it with no assessment to the members.
• One staffed gate. All 548 homes, including Lantana and Da Vinci Estates, are reached only through the gatehouse on Treeline Dr, which the master association’s site map marks with a staffed guard house.
• A-rated assigned schools. Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for every single-family street for 2026 to 2027, all three graded A in 2024, 2025 and 2026 per the Naples Daily News school grade database, which republishes Florida Department of Education data. Laurel Oak’s campus is 1.2 road miles from the entrance.
• 1.6 miles to I-75. The entrance is 1.6 road miles, about 3 minutes free-flow, from Exit 111 at Immokalee Rd on the OSRM routing model.
• Preserve holes and wildlife. The club says holes 13 and 14 are “two of the Club’s three preserve holes with no homes around them,” and describes bobcat, white-tailed deer and river otter on the property in its post Discover the Wild Side of Olde Cypress.
• Exterior landscaping handled at the neighborhood level. The master association’s About page says the quarterly neighborhood invoice includes basic exterior landscaping of each home, along with common grounds, streetlights, signage, paving and stormwater.

The Cons

• Mandatory social dues are not published. Every owner is a social member by covenant under the 2019 Amended and Restated Declaration for Olde Cypress, with dues set by the club “from time to time.” The club publishes no dollar figure. A buyer learns it from the club’s membership office at (239) 596-4797 and should see it in writing before the inspection period ends.
• Golf initiation is not published, and the figures online conflict. Third-party figures for golf initiation run from roughly $45,000 to $175,000 and contradict one another; none comes from the club. Some even describe an equity category, which conflicts with the club’s own statement that it is non-equity.
• The club is owned by a private company, not by the members. The course land is titled to Olde Cypress Development, a Stock family entity since 1998, which converted from a limited partnership to an LLC on July 24, 2026 per its Sunbiz filing record. The club has never been sold to members. Members carry no capital risk, and they also hold no vote in the club’s decisions and no equity to recover.
• Immokalee Rd is a failing road. The segment that fronts Olde Cypress, Logan Blvd to Collier Blvd, ran at 103.4% of peak-hour capacity at level of service F in the county’s 2025 Annual Update and Inventory Report, after 113.4% in 2024. The county’s stated remedy is to monitor and to let the Vanderbilt Beach Road Extension redistribute traffic. The gate opens onto Logan Blvd N (level of service C), but most trips still use Immokalee Rd.
• Some homes pre-date the Florida Building Code. Of the 366 homes inside the Olde Cypress PUD, 155 already appear in the county’s 2000 or 2002 building-footprint imagery, which suggests they were permitted before the first statewide Florida Building Code took effect in March 2002. That is an inference from imagery dates, not a permit record. Roof age, window and door ratings and a wind mitigation report matter more on those homes.
• The effective flood map still shows Zone AH on many lots. On the May 16, 2012 FIRM panels, 141 of the 366 PUD homes have footprints wholly in Zone AH and 133 partly, based on the FEMA National Flood Hazard Layer. The March 2025 preliminary map puts all 366 in Zone X, but it is not effective until the county’s appeal process ends, with a summer 2027 target. Until then a lender can require flood insurance on an AH-mapped home unless it holds a LOMA.
• No community-owned pool or park inside the gate. The master association’s map and site show no association-owned pool, playground or park behind the gatehouse. The club pool, courts and fitness center sit outside the gate and come with social membership. Whether any neighborhood association keeps its own amenity is in that neighborhood’s documents.
• The Fairway Preserve name causes confusion. Fairway Preserve at Olde Cypress is a separate 264-unit, three-story condominium off Immokalee Rd with its own gate on Dancing Wind Ln, its own 2005 declaration (OR 3866 PG 4006) and a Gulf Coast High assignment. It is not on the master association’s map, it is not behind the Olde Cypress gate, and portal searches that mix its sales into “Olde Cypress” distort price comparisons.
• Neighborhood fees are not public. Quarterly assessments are billed by each of the nine neighborhood associations and include the master share, but no amount is published outside the resident portal. The estoppel certificate states it at contract.

Who Olde Cypress Suits Best

Olde Cypress suits a buyer who wants a detached house inside a private golf club without an equity stake, who is comfortable with the social membership coming with the deed, and who values quick, predictable resale. It does not suit a buyer who needs published club and association costs before writing an offer, who wants condominium or coach home product, or who wants an amenity center inside the gate.

As the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate, and the pattern holds in every club community: the homes that sell best are the ones whose trade-offs are disclosed before the buyer finds them.

Thinking of selling your Olde Cypress home? Call Jesse direct at (239) 898-6072 or start with a free valuation of your Olde Cypress home. Considering buying in Olde Cypress? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.

Thinking of Selling Your Olde Cypress Home? List With the #1 Team in Southwest Florida Since 2012

Selling in Olde Cypress means selling one of 548 single-family homes where 26 homes closed in the last 12 months at a $1,105,000 median, in a median 29 days and at 97.52% of list. The Olde Cypress listing that wins is priced against its own neighborhood, explains the club before buyers ask, and answers the flood question first.

Data updated: September 2026

If you’re searching for the best Olde Cypress listing agent, or thinking, ‘I need to sell my house in Olde Cypress…’ you are selling into one of the fastest-moving golf markets in North Naples, and into a buyer pool that arrives with three questions no listing sheet answers: what the club costs, what the flood map says, and which of the nine neighborhoods they are really buying in. McGreevy and Comisar sell Olde Cypress on the record: the recorded 2019 Declaration, the master association’s realtor rules, FEMA’s letters and both flood maps, and the recorded sales neighborhood by neighborhood. As the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate, and that discipline is what an Olde Cypress listing needs.

Three pages go deeper for owners and buyers here: our guide to selling a home in Olde Cypress, a neighborhood-by-neighborhood answer to what your Olde Cypress home is worth, and our guide to buying a home in Olde Cypress.

What Olde Cypress Homes Sold For in the Last 12 Months

In the last 12 months we tracked 26 Olde Cypress closings in the Southwest Florida MLS Matrix, pulled September 26, 2026. Every one was a single-family home, and Olde Cypress is a resale community with no builder sales in the window.

• 26 closed sales, trailing 12 months to September 26, 2026, for $32,328,300 in volume
• Median sold price: $1,105,000 (n = 26, even, so the mean of the middle pair, $1,100,000 and $1,110,000)
• Median sold price per square foot of living area: $472.75
• Median days on market: 29 (n = 24; two sales were entered after closing without a marketing period)
• Median sold-to-list ratio: 97.52%, with 6 of 26 at or above list
• Highest sale: $2,990,000, Da Vinci Estates, January 2026 (entered after closing); fastest: 0 days, a Lantana home at its full $1,735,000 list price, January 2026

The county’s own record, a separate data set, tells the same story from the deed side. The Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026) hold 24 Olde Cypress single-family sales in the 12 months to the file date, with a median recorded price of $1,142,500 (even n, so the mean of the middle pair). Recorded prices in that window ran from $634,800 (a Santorini Villas home, January 2026) to $2,990,000 (a Da Vinci Estates home, January 2026). The latest recorded sale in the file closed May 22, 2026, because deeds reach the county file with a lag. The MLS count (26 to September 26) and the county count (24 to August 29, with recordings through May 22) cover different windows and different records, so we report them side by side and never blend them.

The longer county record shows how the market moved. Calendar-year median qualified sale prices were $725,000 in 2020 (47 sales), $990,000 in 2021 (46), $1,347,500 in 2022 (34), $1,550,000 in 2023 (29), $1,322,500 in 2024 (18) and $1,367,500 in 2025 (30); 2026 through May 22 stands at $1,110,000 on 17 sales. The 2023 peak and the softer 2026 median are both on the public record, and pricing has to respect both.

Pricing by Neighborhood, Not by Gate

Olde Cypress is nine neighborhoods behind one gate, and they do not trade as one market. Over 36 months of Collier County Property Appraiser recorded qualified sales (data file dated August 29, 2026), the neighborhood medians ran:

A community-wide median that mixes a Santorini villa with a Da Vinci Estates estate tells a seller very little. We price every Olde Cypress home from its own neighborhood’s sales first, then adjust for lot, view and condition. Lot size varies as much as price: county parcel polygons put the median Da Vinci Estates lot at 18,263 square feet against 6,639 in Santorini Villas. And the view matters: nearly every home in Unit One, Terramar, Santa Rosa, Egret Cove and Biscayne Place backs onto the golf course parcel, while Lantana is mostly lake-oriented and Lone Pine Ln splits between golf and preserve.

What Is Your Olde Cypress Home Worth? Get a Free Valuation in 60 Seconds.

Start with a free valuation of your Olde Cypress home. It takes about a minute, and Jesse follows up with the sales that fit your home: the same neighborhood, a comparable lot and view, and the same flood position, not a community-wide median.

(239) 898-6072, text or call. Confidential conversations welcome.

How We Market an Olde Cypress Home

An Olde Cypress sale runs on explanation and paper. The seller who has both ready before the first showing negotiates on price, not on uncertainty. This is the file we build.

We explain the club to buyers before they ask. Every buyer becomes a social member of The Club at Olde Cypress at closing under Section 14.02 of the 2019 Amended and Restated Declaration for Olde Cypress, and Full Golf or Associate Golf is an optional upgrade. The club does not publish its dues or initiation, and figures online conflict, so we tell buyers plainly that the current numbers come from the club’s membership office at (239) 596-4797 and belong in the contract review. We also explain the structure: the club’s equity versus non-equity explainer describes non-equity membership as not subject to assessment, non-transferable and without ownership. Out-of-area buyers who have only known equity clubs need that said once, early, and clearly. The club’s membership page also says Full Golf and Associate memberships are open to non-residents as of September 2026, which tells a buyer that golf availability is not a waiting-list gamble.

We work inside the gate and sign rules. The master association’s Realtors Information page allows public open houses on Saturdays and Sundays from 12 to 5 only, with broker opens Monday through Friday. Open house signs are picked up at the guard house against a $20 refundable deposit, and the only For Sale sign allowed is the standardized green wooden sign (2 feet by 1.5 feet, with cream lettering). Outside open house hours, prospective buyers must be with an agent or the owner, or be phoned in by a homeowner. We schedule showings and opens around those rules, and we reach buyers before they ever reach the gatehouse.

We assemble the fee disclosure packet. The quarterly assessment is billed by your neighborhood association and includes the master association’s share, but no amount is published outside the resident portal, per the master association’s About page. We order the estoppel certificates early so the settlement statement uses the associations’ numbers, and we confirm the master association’s working capital contribution, which Section 8.13 of the Declaration collects at each transfer of title in an amount the board sets. We add the leasing rules for investor buyers: the recorded leasing amendment sets a 60-day minimum lease, no more than four leasehold interests per parcel per year, a $100 application fee and a $1,000 refundable common area deposit. We also document that there is no CDD, with the Collier County Tax Collector 2025 bill as the evidence.

We put the flood letters and elevation certificates in the lender file on day one. FEMA has issued 42 Letters of Map Change since 2012 for property on these streets and the neighboring Fairway Preserve condominium, almost all removing an individual structure from the Special Flood Hazard Area, and the letters we read name ponding and overland flow as the flooding source, not coastal surge. Lantana goes further: FEMA LOMR-F 13-04-6118A, dated August 8, 2013, removed all 122 Lantana lots from the Special Flood Hazard Area, even though FEMA’s map graphic still paints Lantana as Zone AH. If your home has a LOMA, a LOMR-F or an elevation certificate, it goes into the listing file before the buyer’s lender orders a flood determination. If it has none, a current elevation certificate is worth ordering before listing on any home the effective map shows in Zone AH. Collier’s own freeboard standard for new construction is in Collier County Building Bulletin 21.

We explain the preliminary flood map without overselling it. On FEMA’s preliminary March 2025 flood maps, all 366 homes inside the Olde Cypress PUD fall in Zone X, and 59 of 60 Da Vinci Estates homes do too. Lantana is the exception, with 72 of 122 footprints still touching Zone AH on the preliminary panels. Those maps are not effective: Collier County opened the 90-day appeal period on August 19, 2026, with the new FIRM targeted for summer 2027. We show buyers both maps, label which is in force, and let the lender decide building by building. We name the FEMA zone for each building and never promise a buyer that flood insurance will not be required.

We present the homestead picture accurately. About seven in ten homes inside the Olde Cypress PUD carry a Florida homestead exemption on the 2026 preliminary Collier County roll, so most sellers are owner-occupants whose assessed value is capped. A buyer’s taxes reset at purchase, and we explain that before the buyer’s lender does.

To start that file on your home, call Jesse direct at (239) 898-6072 or request a free valuation of your Olde Cypress home.

Does my club membership transfer to my Olde Cypress buyer?

The social membership does not need to transfer: under Section 14.02 of the recorded 2019 Declaration, your buyer “automatically becomes a social member of The Club at Olde Cypress” on acquiring the parcel. Golf membership is different. The club describes its non-equity memberships as non-transferable in its equity versus non-equity explainer, and it publishes no initiation, dues, resignation or refund terms. Ask the club’s membership office at (239) 596-4797 what happens to your golf membership at sale, and what your buyer would pay to join at Full Golf or Associate Golf, before you list. We put that answer in the marketing so no buyer discovers it at the inspection deadline.

How long does it take to sell a home in Olde Cypress?

The median Olde Cypress home sold after 29 days on market in the 12 months to September 26, 2026, on 26 closings (24 with a marketing period) in the Southwest Florida MLS Matrix, the fastest of the seven North Naples communities we benchmarked. Add time for the contract and closing, and for the estoppel certificates from your neighborhood and master associations. A median is a middle, not a promise: an overpriced home in any neighborhood can sit far longer than 29 days while its neighbors sell.

Can I hold an open house in Olde Cypress?

Yes, on the master association’s schedule. Its Realtors Information page permits public open houses on Saturdays and Sundays from 12 to 5, with broker opens Monday through Friday. Open house signs come from the guard house against a $20 refundable deposit, and only the standardized green wooden For Sale sign is allowed. At other times, buyers must be accompanied by an agent or the owner, or be phoned in by a homeowner.

Will my buyer need flood insurance?

It depends on your building, not the community. On the effective May 16, 2012 FIRM panels many Olde Cypress homes touch Zone AH, a shallow ponding zone, and a lender can require flood insurance on those unless the home holds a LOMA or LOMR-F. Many do: FEMA has issued 42 such letters in these neighborhoods since 2012, and Lantana’s entire subdivision was removed by LOMR-F 13-04-6118A in 2013. The March 2025 preliminary map places every home inside the Olde Cypress PUD in Zone X, but it is not effective until the appeal process ends, with a summer 2027 target. For context, the median NFIP single-family policy in ZIP 34119 cost $1,259 a year in OpenFEMA’s NFIP policy data as of September 8, 2026. Put your letter or elevation certificate in the file before the buyer’s lender asks.

Is there a CDD payoff or bond balance when I sell in Olde Cypress?

No. Olde Cypress has no Community Development District: none appears in the Collier County CDD map layer or on the state’s list of dissolved special districts, and the 2025 tax bill for a Lone Pine Ln home carries only a $261.91 garbage charge beyond ad valorem taxes at 9.5058 mills. Streets, stormwater and common areas are funded through the master and neighborhood assessments instead. What you do settle at closing is your share of those assessments, confirmed by estoppel certificate.

Can I sell my Olde Cypress home to an investor who plans to rent it?

Yes, within the recorded leasing rules. The recorded leasing amendment and the 2019 Declaration require a written lease of at least 60 days, no more than four leasehold interests per parcel in a calendar year, whole-home leases only, no subleasing, board approval with a credit and background check, a $100 application fee and a $1,000 refundable common area deposit. Short-term vacation rental is not possible. Neighborhood associations can add their own rules, so we pull those for the specific neighborhood before we market to investors.

Who is the best listing agent for Olde Cypress?

The best listing agent for Olde Cypress is the one who can price your home from its own neighborhood’s sales, explain an unpublished club structure to a buyer without guessing, and put FEMA’s letters in front of a lender before the flood question stalls a contract. McGreevy and Comisar are the #1 team in Southwest Florida since 2012 and Top 1% Real Estate Agents Nationally Since 2008, and we built this guide from the recorded Declaration, the club’s own statements, both FEMA maps and every recorded sale. Call Jesse direct at (239) 898-6072 or request a free valuation of your Olde Cypress home. Buyers can call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.

Your Local Real Estate Experts

Jesse McGreevy and Marc Comisar, the McGreevy and Comisar team behind this Olde Cypress guide, lead Domain Realty Group from an office on US 41 in Bonita Springs, a short drive up I-75 from the Olde Cypress gate. Jesse leads the listing side and Marc works with buyers in the field across North Naples, Estero and Bonita Springs.

Jesse McGreevy is a top-reviewed Olde Cypress realtor on Google. Jesse McGreevy, Sales Associate, has lived in Estero since 2003, so the I-75 corridor from Estero down to Immokalee Rd is home ground. Marc Comisar, Broker Associate, is the partner in the field: the showings, the walk-throughs and the buyer negotiations. The team launched in October 2008, and the longer story of how it was built is on our about the McGreevy and Comisar team page.

McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com.

• Top 1% Real Estate Agents Nationally Since 2008
• 5 Star Award for Customer Satisfaction for 21 Straight Years. Only 5 out of 21k+ Licensees (Gulfshore Life Magazine)
• #1 Team in Southwest Florida since 2012
• McGreevy and Comisar and their Domain Realty Group team have sold over $2.5 Billion in Real Estate
• McGreevy and Comisar alone have over $900 million in Sales
• Nationally Recognized Top Producing Realtors
• Platinum Sales Production Award Winners

On an Olde Cypress page, the credential that matters is narrower than any award. Before this guide was written we read the 71-page recorded 2019 Declaration with its Articles and Bylaws, the recorded leasing amendment, the club’s own statements on membership and ownership, the Sunbiz chain for the club’s owner, both FEMA flood maps and FEMA’s letters for these streets, the 2026 preliminary county roll for all 548 homes, the district’s 2026 to 2027 school lookup and every recorded qualified sale in the county file. That preparation, applied to your home, is what we offer an Olde Cypress seller or buyer.

What Our Clients Say

Jesse McGreevy and Marc Comisar are top-reviewed on Google, and the quotes below are five-star client reviews reproduced in the reviewer’s own words. We publish no aggregate score and no star-rating widget. Read the full set on the McGreevy and Comisar Google Business Profile.

★★★★★ “I have had 13 real estate transactions and this is the most professional and helpful agency that I have ever worked with. Marc actually called me with a response to my questions and concerns on a Sunday evening. The resources that this agency has access to goes above and beyond any other I have ever worked with. The professional process that they use to present your home for sale goes beyond anything I have ever experienced.” Verified Google review

★★★★★ “Jesse was very professional, helpful and kept in touch with ideas and suggestions which developed into a sale. Highly recommend his company for their excellent follow through.” Verified Google review

★★★★★ “We have purchased many properties over the years and Jesse is without a doubt the most knowledgeable, personable and efficient real estate broker we have ever worked with!” Verified Google review

★★★★★ “We have used his services for 5 transactions and every one has gone smoothly. He is a fantastic communicator, offers great representation, and is extremely honest.” Verified Google review

★★★★★ “Marc’s knowledge of the Southwest Florida real estate market is unmatched. He took the time to understand exactly what I was looking for in a home and quickly identified properties that checked all my boxes.” Verified Google review

Contact McGreevy and Comisar

• Jesse McGreevy: (239) 898-6072 · [email protected]
• Marc Comisar: (239) 287-5873
• Office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134

Selling an Olde Cypress home? Get a free valuation of your Olde Cypress home, or call Jesse direct at (239) 898-6072.

Buying in Olde Cypress? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.

Licensure, and the Office of Record

Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).

• Jesse McGreevy, Florida license SL3101296
• Marc Comisar, Florida license BK3060671
• Brokerage office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134

License status for either name can be verified through the Florida Department of Business and Professional Regulation’s public licensee search, the authority of record for Florida real estate licensure.

Where Else to Find the Team

For the wider market around Olde Cypress, see our Naples guide, our Collier County guide and our roundup of the best real estate agents in Naples, compared on the public record. The team site for Domain Realty Group is DomainRealtyGroup.com.

Olde Cypress FAQ: Buyer Edition

Olde Cypress is a gated golf community of 548 single-family homes in North Naples, unincorporated Collier County, ZIP 34119, with a privately owned P.B. Dye golf club, no CDD and one staffed gate on Treeline Drive. The answers below come from recorded documents, county and state records, FEMA, Collier County Public Schools and the club’s own pages.

Data updated: September 2026

What is Olde Cypress in Naples, Florida?

Olde Cypress is a gated golf community in North Naples with 548 single-family homes on the 2026 preliminary Collier County roll, which the master association rounds to 550 on its Olde Cypress Master Association About page. Nine neighborhood associations sit under one master association, and every owner automatically becomes a social member of The Club at Olde Cypress under Section 14.02 of the 2019 Amended and Restated Declaration for Olde Cypress. The club, an 18-hole P.B. Dye course and clubhouse, is privately owned and non-equity. Our Naples guide places Olde Cypress in the wider city picture.