Sell Your Home in Olde Cypress, FL

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

Why Sell Your Olde Cypress Home With McGreevy and Comisar?

Olde Cypress is a gated North Naples golf community of 548 single-family homes in nine neighborhoods, where every owner carries a mandatory club social membership and the sale runs on neighborhood-level pricing, two association estoppels and a flood file. McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008, price it neighborhood by neighborhood.

This page is written for the owner who is thinking about selling. The full picture of the community, from the 1998 Stock family partnership behind the club to the golf course hole by hole, lives in our Olde Cypress community guide, and this seller page sits beside it. Everything below answers one question: how to sell a Da Vinci Estates estate, a Lantana home, a Terramar or Santa Rosa home on the golf course, a Lone Pine Lane home or a Santorini villa for the most money, with the fewest surprises, on a date you choose. Call Jesse McGreevy direct at (239) 898-6072 whenever you want to talk it through.

Sell Your Olde Cypress Home With the #1 Team in Southwest Florida Since 2012

Jesse McGreevy and Marc Comisar have been Top 1% Real Estate Agents Nationally Since 2008 and the #1 Team in Southwest Florida since 2012, and they personally run every listing they take: the price, the marketing build, the negotiation, and the association and club paperwork. If you are interviewing listing agents across the city before you choose one, our guide to the best real estate agents in Naples compares the teams on the public record, from reviews to licence history to published production.

The Credentials, Stated Plainly

• 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

These are career figures across Lee and Collier County, not a claim about one gated community, and we label them that way on purpose. As the leaders of Domain Realty Group, our team has closed over $2.5 billion in real estate, and Jesse and Marc alone have over $900 million in Sales inside that number. The wider team is at DomainRealtyGroup.com.

What We Do Not Publish About Ourselves, and Why

This page carries no McGreevy and Comisar sales count for Olde Cypress and no story of an Olde Cypress sale we handled, because we will not print one we cannot document for you. What we can show you is the whole market: 26 closings in the Southwest Florida MLS in the last twelve months and 24 qualified sales in Collier County's own deed record over roughly the same year, each with its source and date. Where this page walks through a sale in detail, it is a public record sale, labelled as one, and not ours.

Who Does the Work on Your Listing

You get Jesse and Marc, not a coordinator reading from a template. Jesse McGreevy runs pricing, data, marketing and the association and club paperwork. Marc Comisar runs the field: showings through the Treeline Drive gate, buyer agent conversations, inspections, contractors and walkthroughs for owners who are out of state. Reach Jesse at (239) 898-6072 or Marc at (239) 287-5873, and read how the partnership works on our about McGreevy and Comisar page.

What Makes Selling in Olde Cypress Different?

Selling in Olde Cypress differs from a typical Naples sale in five ways: nine neighborhoods trade as separate markets, club social membership passes with the deed while golf does not, no association or club dollar amount is published, the flood maps are in transition, and there is no Community Development District line to explain.

Nine Neighborhoods, One Gate, One Product Type

The Collier County Property Appraiser 2026 preliminary roll counts 548 single-family homes behind the gate, which the master association rounds to 550. They sit in nine neighborhood associations: the Olde Cypress Homeowners' Association (Units One, Two and Three, 185 homes), Lantana (122), Da Vinci Estates (60), Terramar (55), Santorini Villas (55), Santa Rosa (27), Egret Cove (18), Strada Bella (18) and Biscayne Place (8). Every home is single-family, and the only attached product is the 55 paired villas of Santorini Villas. A Santorini villa at the 36-month recorded median of $640,000 and a Da Vinci Estates home at $2,387,500 share one staffed gate on Treeline Drive and nothing else a pricing model can use.

The Club Social Membership Comes With the Deed

"By acquisition of a Parcel, each Owner automatically becomes a social member of The Club at Olde Cypress," says Section 14.02 of the 2019 Amended and Restated Declaration for Olde Cypress, recorded November 27, 2019 at OR 5700 PG 1118. Your buyer inherits the social membership automatically; golf is a separate, optional purchase from the club. The club is privately owned and non-equity, so there is no equity certificate to sell back and nothing refunded at closing.

No Published Price for the Club or the Associations

The club does not publish its social dues, golf initiation or golf dues, and none of the nine neighborhood associations publishes its quarterly assessment outside the resident portal. Third-party golf initiation figures circulating online conflict widely, from roughly $45,000 to $175,000, and none of them is club-published. The seller who has the current club figures and the estoppel certificate in hand before listing takes the biggest negotiating question off the table.

A Flood Story With Three Chapters

On FEMA's effective May 16, 2012 maps, 141 of the 366 homes inside the Olde Cypress PUD have footprints wholly in Zone AH and 133 partly; FEMA's March 20, 2025 preliminary map draws all 366 in Zone X; and Lantana was removed from the Special Flood Hazard Area by a 2013 Letter of Map Revision that the map graphic still does not show. A buyer's lender will ask which chapter applies to your house.

No CDD, and a Tax Reset Your Buyer Inherits

Olde Cypress has no Community Development District, so there is no district debt line on the tax bill to explain away. What the buyer does inherit is a tax reset: on the 2026 preliminary roll the median homesteaded home inside the PUD pays $6,361 and the median non-homesteaded home pays $9,176, and a buyer does not keep the seller's Save Our Homes cap.

Key Takeaways for an Olde Cypress Seller

• Olde Cypress has 548 single-family homes in nine neighborhoods behind one staffed gate on Treeline Drive off Logan Boulevard North, in North Naples ZIP 34119.
• The Southwest Florida MLS recorded 26 closings and $32,328,300 in volume in the twelve months to September 26, 2026, a median of $1,105,000, a median 29 days on market and a median 97.52 percent of list. Six of 26 closed at or above list.
• Five homes were active and one was pending on that date, about 2.3 months of supply, from $630,000 in Santorini Villas to $3,390,000 in Da Vinci Estates.
• Against named neighbors in the same MLS, Olde Cypress sold faster and closer to list than The Vineyards (75 days, 94.74 percent) and Tiburon (86 days, 93.84 percent), and ties Longshore Lake on days (29).
• Collier County's deed record shows 24 qualified sales at a $1,142,500 median in the twelve months to its August 29, 2026 file, and a calendar-year median that peaked at $1,550,000 in 2023.
• Over 36 months of recorded sales, neighborhood medians run from $640,000 in Santorini Villas to $2,387,500 in Da Vinci Estates.
• Club social membership passes with the deed; golf does not, and neither the club nor the nine associations publish a dollar figure, so the estoppel and the club's written figures belong in your listing file.
• There is no CDD, the 2025 millage was 9.5058 mills, and the only non-ad valorem line on a sampled 2025 bill was garbage at $261.91.

Is Now a Good Time to Sell in Olde Cypress?

For a home priced to its own neighborhood, yes. The Southwest Florida MLS shows 26 Olde Cypress closings in the twelve months to September 26, 2026, a median 29 days on market, 97.52 percent of list and about 2.3 months of supply, a tight reading. The market still punishes an ask above the recent sales: three of today's five listings have waited 93 to 283 days.

Data updated: September 2026 (Southwest Florida MLS Matrix, Development OLDE CYPRESS and SANTA ROSA AT OLDE CYPRESS, closed in the twelve months to and active on September 26, 2026, pulled September 26, 2026)

We tracked every one of the 26 Olde Cypress closings recorded in the Southwest Florida MLS in the twelve months to September 26, 2026, neighborhood by neighborhood, and read them beside Collier County's recorded deed record before we wrote a single figure on this page.

The Twelve-Month MLS Picture

Every row sits in City NAPLES under the Development names OLDE CYPRESS or SANTA ROSA AT OLDE CYPRESS, which together cover all nine neighborhoods, including Lantana and Da Vinci Estates, and return no Fairway Preserve condominium. Sold-to-list is measured against the final list price.

The Parity Rule on These Medians

When a count is even, the median is the mean of the middle pair, and we show the pair so anyone can check it. The $1,105,000 median is the mean of $1,100,000 and $1,110,000. The 29-day median comes from the 24 closings that carry a days-on-market value, with 24 and 34 in the middle; two sales were entered after closing with no marketing period. The 97.52 percent sold-to-list is the mean of 97.18 and 97.85 percent.

This Year Against the Year Before

Sellers got closer to list (97.52 against 93.54 percent) and sold faster (29 days against 37). Do not read the lower median as a 22 percent fall in values: the latest year includes six Lone Pine Lane sales and four Santorini villas, the two lowest-priced neighborhoods, and one Da Vinci Estates sale. The median price per square foot, which adjusts for size though not for neighborhood, eased about 5 percent.

Where Today's Five Active Listings Sit

On September 26, 2026 the five active listings were a Da Vinci Estates home on Mona Lisa Boulevard at $3,390,000 (5,538 square feet, 162 days), two Terramar homes at $1,825,000 (133 days) and $1,669,900 (17 days), and two Santorini villas at $749,900 (93 days) and $630,000 (283 days). A Treeline Drive home at $1,790,000 went pending with contingency after 4 days. In a market this size, every one of those homes is a comparable your buyer tours the same afternoon.

How Olde Cypress Stacks Up Against Its Neighbors

Source: Southwest Florida MLS Matrix, Development names VINEYARDS, LONGSHORE LAKE, STERLING OAKS and TIBURON, closed September 27, 2025 to September 26, 2026 and active on the pull date, pulled September 27, 2026; Olde Cypress pulled September 26, 2026. The Vineyards, Sterling Oaks and Tiburon rows include condominiums and villas; every Olde Cypress sale was single-family.

The yardsticks are the ones a seller decides on. Olde Cypress closed at 97.52 percent of list against 94.74 percent in The Vineyards and 93.84 percent in Tiburon, so the typical negotiation here gives up about 2.5 points of price against roughly 5 and 6 points next door. Its 2.3 months of supply sits below Longshore Lake's 2.6, The Vineyards' 3.5 and Tiburon's 7.9. Your buyer's alternatives inside the gate are few; the alternatives outside it are where the competition lives.

What Has the County Deed Record Shown Since 2016?

Collier County's deed record shows the Olde Cypress median sale more than doubling from $670,000 in 2016 to a $1,550,000 peak in 2023, then easing to $1,110,000 on the 17 sales recorded in 2026 through May 22. In the twelve months to the August 29, 2026 file, the county recorded 24 qualified sales at a $1,142,500 median.

Data updated: September 2026 (Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026, joined to the 548 single-family parcels on the 2026 preliminary roll)

The Recorded Record by Window

A qualified sale is a transfer the county itself graded as an arm's-length market sale. The longer the window, the higher the median, which tells a seller the latest year has recorded for less than the years just before it. Part of that is price and part is mix: the last twelve months include six Lone Pine Lane sales and three Santorini villas.

The Calendar-Year Median, 2016 to 2026

From 2016 through 2020 the median barely moved. It then jumped to $990,000 in 2021, $1,347,500 in 2022 and $1,550,000 in 2023, about 2.3 times the 2016 figure. The 2026 figure is about 28 percent below the 2023 peak and still about 66 percent above 2016. For an owner who bought before 2021 the gain is large; for one who bought near the 2023 top, the honest conversation starts from these recorded numbers rather than from a neighbor's 2023 sale.

Recorded Sales by Neighborhood, 36 Months

The spread is the story. Inside one gate and under one club requirement, a Da Vinci Estates home recorded at a median $2,387,500 while a Santorini villa recorded at $640,000. A community-wide median describes almost no actual home, which is why an Olde Cypress price opinion starts from the neighborhood, then the view, then the lot.

Why the MLS and County Counts Differ

The MLS counts 26 closings and the county 24 qualified sales, and neither is wrong. The county grades every deed and keeps only arm's-length sales, and its file ends at the May 22, 2026 recording because deeds lag; the MLS counts listed homes and runs to September 26. We use the county for what sold and at what recorded price over the long run, and the MLS for how long it took and how close to asking it closed. We never blend the two into one figure.

Which Recent Olde Cypress Sales Matter Most to Your Price?

The Olde Cypress sales that matter most are the ones in your own neighborhood, with your view and your size. Because no neighborhood recorded ten MLS closings in the last year, we list every sale rather than invent a neighborhood median: a median of three or four sales is not a market rate.

Data updated: September 2026 (Southwest Florida MLS Matrix, closed September 27, 2025 to September 26, 2026, pulled September 26, 2026)

Every MLS Closing of the Year

Living area is the figure the listing agent entered in the MLS, not the county's base area. "Entered after closing" marks a sale added to the MLS after it closed, with no marketing period.

Lantana Carried the Year

Lantana, the 2013 to 2016 build of 122 homes, produced 8 of the 26 closings at a median of $1,495,000 (the mean of $1,400,000 and $1,590,000), a median 9 days on market and a median 98.68 percent of list. Four of its eight sold within six days, and two reached or beat their list price. Its two smaller homes, at 1,801 and 1,809 square feet, sold at $859,000 and $860,000; its larger homes near 2,900 to 3,150 square feet sold from $1,590,000 to $1,795,000. In Lantana, size and lake view set the price more than the street name.

Lone Pine Lane: Six Closings and the Longest Wait

Lone Pine Lane in Unit Three produced 6 closings, from $775,000 to $1,110,000, at a median of $972,500 (the mean of $940,000 and $1,005,000) and a median 94.52 percent of list. It also produced the slowest sale of the year: a 2,407 square foot home that closed at $775,000 after 293 days, 93.38 percent of its final list. The fastest Lone Pine sale went under contract in 13 days at 94.10 percent. A Lone Pine owner should price to the street's own recent sales, not to the Olde Cypress median.

Santorini Villas: Four Closings Near 97 Percent

The four Santorini villa closings ran from $630,000 to $800,000 at a median of $638,900, a median 97.68 percent of list and a median 75 days on market. Villa buyers negotiate little on price and take their time deciding, which is the pattern of a smaller, more price-sensitive buyer pool. Two Santorini villas are listed now, at $630,000 and $749,900, and one of them has waited 283 days.

Terramar, Santa Rosa and the Golf Course Streets

Terramar recorded three closings, at $1,075,000, $1,099,000 and $1,750,000, with sold-to-list of 89.96, 100 and 92.11 percent. Santa Rosa recorded two, at $1,512,500 after 7 days and $1,600,000 after 34 days. The two Treeline Drive sales, in Units One and Two, split sharply: $1,275,000 at 98.08 percent after 6 days, and $1,225,000 at 81.72 percent after 124 days. The same street produced the best and worst sold-to-list outcomes of the year, and the difference was where each started.

The Most Recent Public Sale, Worked Through

This is a public record sale from the Southwest Florida MLS, not a McGreevy and Comisar transaction. The most recent Olde Cypress closing in the pull was a Lantana home of 2,327 square feet on August 21, 2026. It was listed at a final $1,340,000, spent 12 days on market and closed at $1,350,000, which is 100.75 percent of list and about $580 per square foot of MLS living area, against the Lantana twelve-month median of about $546.

Three lessons follow for the next Lantana seller. First, it was the only sale of the year that closed above its list price, in August, outside the January to May season, so a well-presented home does not have to wait for winter. Second, at 2,327 square feet it sat between Lantana's small and large homes, yet its roughly $580 per square foot ran above the Lantana median, so a buyer paid for the specific house rather than for the neighborhood average. Third, the sale closed after the county's August 29 file was cut, so it will not appear in the deed record until the next extract; your valuation should include the sales one system has caught that the other has not.

Thinking of Selling Your Olde Cypress Home? Start With a Neighborhood-Level Valuation

Olde Cypress sold 26 homes through the MLS last year at prices from $630,000 in Santorini Villas to $2,990,000 in Da Vinci Estates, so the first price you publish decides which buyers see you. Request a written opinion of value through our Olde Cypress home valuation request or the McGreevy and Comisar free home valuation, or call Jesse McGreevy at (239) 898-6072. Buying instead? See how we help buyers purchase in Olde Cypress, read how we represent buyers in Naples or call Marc Comisar at (239) 287-5873.

The Top Sale of the Year, and What a Seller-Direct Entry Means

The highest closing of the year was a 3,833 square foot Da Vinci Estates home on Mona Lisa Boulevard at $2,990,000 on January 30, 2026, entered in the MLS after closing at its full price, with no marketing period recorded. The same $2,990,000 is the highest recorded Olde Cypress sale in the county's 36-month file. For a Da Vinci Estates owner, that sale is a ceiling reference, not a median: the 48-month MLS median for Da Vinci Estates is $2,150,000 on 17 closings, and today's one Da Vinci listing, at $3,390,000 and 5,538 square feet, has waited 162 days.

What a Buyer's Appraiser Will Reach For

A lender's appraiser looks first for closed sales in the same neighborhood, of similar size and view, within the last six to twelve months. In Olde Cypress that often means two or three sales at most, sometimes none: Egret Cove, Strada Bella and Wild Orchid Court recorded no MLS closing in the last year, and Biscayne Place none in three years. We assemble that comparable set before you list, including the older sales and the next-door neighborhood sales an appraiser will be forced to adjust, so the price we recommend is one a financed buyer's appraisal can support.

Olde Cypress vs The Vineyards: Which North Naples Club Will Your Buyer Also Tour?

Olde Cypress and The Vineyards are both gated North Naples golf communities with privately owned, non-equity clubs and no CDD, and your buyer has very likely toured both. 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 (Southwest Florida MLS Matrix, both communities closed September 27, 2025 to September 26, 2026; Olde Cypress pulled September 26, 2026, The Vineyards pulled September 27, 2026; club and covenant facts from our Olde Cypress and Vineyards guides)

The Decision Table

The Vineyards median blends condominiums, coach homes and villas with houses, while every Olde Cypress sale in the window was single-family, and that product mix explains much of the gap between the two medians.

What the Comparison Means for Your List Price

The buyer who ends up in Olde Cypress has usually decided that a detached house, a built-in social club and a single quiet gate outweigh 36 holes and optional membership. That buyer is also the one who most wants the club's current dues and golf figures in writing, because The Vineyards publishes its schedule and Olde Cypress does not. Your listing should answer that in its first paragraph. Jesse McGreevy at (239) 898-6072 will tell you which buyer pool your home is most likely to meet.

Who Should Choose Which

Choose Olde Cypress if the buyer wants a detached home, one well-kept P.B. Dye course with easy tee times, a club where every neighbor is a social member, and a resale market that has closed in about a month. Choose The Vineyards if the buyer wants product choice below $1 million, 36 holes, or the freedom to buy the house now and decide on the club later from a published schedule.

How Do Olde Cypress Costs Compare With Other Clubs a Buyer Tours?

Olde Cypress competes on a short list of costs a buyer can check: no CDD, no member assessments, no food and beverage minimum and no equity purchase, against a club and association that publish no dollar figures. For a seller, the strengths are selling lines; the unpublished figures are a disclosure task to finish before listing.

Data updated: September 2026 (The Club at Olde Cypress About Us page and Club Insider articles; 2025 Collier County Tax Collector bill; Collier County CDD layer)

No Assessments, No Minimum, No Equity to Buy

The club 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 reported by the Business Observer was funded by the Stock family owner with no assessment to members. In a member-owned equity club, a buyer can inherit a capital call; here the owner carries the capital. That is a line for the first paragraph of an Olde Cypress listing.

The Renovated Clubhouse Is a Selling Line in 2026

The clubhouse closed for construction in March 2025, reopened after Phase I in early March 2026 and finished with the Greenside Grille and outdoor bar in late April 2026, per Club + Resort Business. The golf course stayed open throughout. A buyer who read a 2025 comment about construction deserves the current answer, and your listing should give it.

The One Published Club Number

The only first-party club dollar figure we found is the $1,950 annual fee for using a private golf cart on the course, from the club's Five Things to Know article, which also says about 60 percent of members use their own carts. Everything else, social dues, golf initiation and golf dues, comes from the membership office at (239) 596-4797 in writing.

Golf Is Optional, Which Widens the Buyer Pool

Because golf is a separate purchase, your buyer pool includes the household that wants the gate, the clubhouse and the courts and never plays. In a bundled-golf community every buyer must accept a full golf membership. Market your home to both: the golfer who wants Full Golf or Associate Golf, and the social-only household that wants Olde Cypress for everything else.

How Do We Price an Olde Cypress Home?

We price an Olde Cypress home from the recorded and MLS sales of its own neighborhood, adjusted for size, golf, lake or preserve view, lot, pool, roof, impact protection and condition, then test the number against the live listings and what a buyer's appraiser will find. We never start from a community median or an automated estimate.

Data updated: September 2026 (Collier County Property Appraiser 2026 preliminary roll and recorded qualified sales, data file dated August 29, 2026; Southwest Florida MLS Matrix, pulled September 26, 2026)

We Start With Your Neighborhood

Just value is the county's mass-appraisal estimate for taxation, not a sale price, and in most rows it sits below the recent sale median. The ranking between neighborhoods is what a pricing analysis must respect. The MLS groups Units One and Two and Biscayne Place together by street, so those rows are not directly comparable.

Two Square-Foot Measures We Never Mix

The county divides a sale price by its own base area; the MLS divides by the living area a listing agent enters. Over 48 months the MLS median runs from about $336 per square foot of living area in Santorini Villas to about $569 in Da Vinci Estates and $584 on Wild Orchid Court. Your valuation states which system every number came from, and never restates one against the other's denominator.

Why Automated Estimates Miss in Olde Cypress

An automated model needs many similar recent sales. Olde Cypress produces about two dozen a year across nine neighborhoods and a price range from $630,000 to $2,990,000. A model can blend a Santorini villa with a Terramar golf home, cannot see whether a lot backs onto a fairway, a lake or the preserve, and cannot read a FEMA letter. Your buyer sees that same estimate, which is why your listing needs the evidence behind your price.

The Value Drivers a Model Cannot See

View first: nearly every home in Unit One, Terramar, Santa Rosa, Egret Cove and Biscayne Place backs onto the golf course parcel, Lantana is mostly lake-oriented and Lone Pine Lane splits between golf and preserve. Lot size second: the median Da Vinci Estates lot is about 18,263 square feet against about 6,639 in Santorini Villas. Then the build era: about 155 of the 366 homes inside the PUD appear in the 2000 or 2002 aerial footprints, so the roof date, impact openings and a current wind mitigation report change the buyer's insurance quote. Each is a measurable adjustment from recorded sales.

Pricing Against the Live Competition

With five active listings, three of them past 90 days on market, your list price is judged against the homes a buyer can walk that same afternoon. We tour them, read their price histories and set your number where it wins the comparison rather than where it merely matches it. The two Terramar listings at $1,825,000 and $1,669,900 are a good example: a third Terramar home priced between them has to show the buyer why.

How Do We Market an Olde Cypress Home?

We market an Olde Cypress home to the buyer who is actually buying in its neighborhood: a full-time household for Lantana, Lone Pine and the Unit One and Two streets, a club-first golfer for the fairway lots, and a lock-and-leave buyer for Santorini Villas. That means professional media, the fee and flood file up front, and a showing plan built around a staffed gate.

Data updated: September 2026 (Collier County Property Appraiser 2026 preliminary roll; Olde Cypress Master Property Owners Association Realtors Information page)

Who Owns, and Therefore Who Will Buy

About seven in ten of the homes inside the Olde Cypress PUD, 252 of 366, carry a Florida homestead exemption on the 2026 preliminary roll. That is a year-round community, and a large share of your buyers will be households moving here full time, often from elsewhere in Naples. The rest are seasonal buyers who want a detached home with a club and a gate. The listing speaks to both: school assignment and commute for the first, club, gate and lock-and-leave logistics for the second.

The Realtor Rules Shape the Plan

The master association's Realtors Information page sets how homes are shown: public open houses on Saturday and Sunday from noon to 5 p.m. only, with broker opens Monday to Friday; outside those hours a buyer must come with an agent or the 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; and one standardized green wooden For Sale sign, 2 feet by 1.5 feet, is the only sign allowed. A buyer who cannot simply drive in has to be reached before arrival, so our showing plan is a guest-access plan first.

Photography, Aerial and Video

Olde Cypress sells from the air: a P.B. Dye course with an island-green 12th, lakes that are also the stormwater system, and a 158.59-acre master preserve on the east. Professional architectural photography, aerial capture, floor plans and a video walkthrough are standard on every McGreevy and Comisar listing, not an upgrade you pay for.

Putting the Club, Fee and Flood File in the Listing Package

Buyers ask about the club, the quarterly invoice, the flood zone and the tax bill at the first showing. We put the club's written figures, the neighborhood association's budget, the estoppel figures, your elevation certificate and any FEMA letter in the listing package from day one, each with its source.

Discreet and Off-Market Options

Not every Olde Cypress owner wants a public launch. An estate sale, a divorce or a health change is often better handled quietly, through direct agent-to-agent outreach and our own buyer database. Less exposure can mean a lower price, and we will tell you plainly which way that trade is likely to land for your neighborhood before you choose it.

How Do We Negotiate an Olde Cypress Contract?

Jesse McGreevy and Marc Comisar negotiate every Olde Cypress offer themselves. With a 97.52 percent median sold-to-list, the typical buyer here negotiates little, but outcomes last year ran from 81.72 to 100.75 percent, and the gap is where a seller's money is kept or lost, so we prepare the club, fee, flood and insurance answers before the first offer arrives.

Partner-Level Negotiation, Never an Assistant

The person who priced your home is the person across the table from the buyer's agent. Offers are not relayed by a coordinator and counteroffers are not written from a template.

Reading a 97.52 Percent Market

The median Olde Cypress closing gave up about 2.5 percent from its final list. The deepest concessions of the year belonged to homes that sat: 81.72 percent after 124 days on Treeline Drive, 92.11 percent after 96 days in Terramar and 93.38 percent after 293 days on Lone Pine Lane. The one early exception, a Terramar home at 89.96 percent after 7 days, shows that a price above the neighborhood's evidence is corrected at the table even when the home sells fast. A home priced on the recorded evidence leaves the buyer less room to argue, and we defend that price with the same evidence.

The Club Question at the Negotiating Table

A buyer who wants golf will ask what it costs and whether your membership transfers. Golf memberships at a non-equity club are typically not transferable, and the club's own explainer describes its model as "Non transferable." We get the club's current written figures before listing, so a buyer's unanswered club question never becomes a price concession.

Inspection, Roof, Wind Mitigation and Insurance

Many Olde Cypress homes were built from 1999 to 2004, and a buyer's insurer will ask for a four-point inspection, with a wind mitigation report that can lower the premium. We recommend both reports before listing, so a problem is found on your schedule rather than inside the buyer's inspection period. A documented roof date and impact openings are worth more at the table than a promise.

Sequencing Two Estoppels and the Club

Your sale needs an estoppel certificate from your neighborhood association that includes the master share, and the title company will confirm the master association's figures. Most Olde Cypress neighborhoods are managed through Alliant Property Management at (239) 454-1101; Da Vinci Estates and Santa Rosa use other management companies. We order every certificate on the first business day after the contract is signed and write the contract dates around the slowest step.

What Does It Cost to Sell a Home in Olde Cypress?

Selling an Olde Cypress home costs the negotiated brokerage commission, Florida documentary stamp tax on the deed at $0.70 per $100, the estoppel certificate fees, a municipal lien search and prorated taxes and assessments. In Collier County the buyer customarily pays the owner's title policy, and the master association's working capital contribution is collected at transfer.

Data updated: September 2026 (Florida Statutes 201.02 and 720.30851; Florida Department of Revenue; 2019 Amended and Restated Declaration for Olde Cypress; Southwest Florida MLS Matrix medians pulled September 26, 2026)

Documentary Stamp Tax on the Deed

Florida charges $0.70 per $100 of consideration, or portion thereof, under Florida Statutes 201.02, and a Florida seller customarily pays it. At the twelve-month MLS figures that is $4,473 on a $638,900 Santorini villa, $7,735 on the $1,105,000 community median, $10,465 on a $1,495,000 Lantana home and $20,930 on the year's $2,990,000 top sale. After commission, it is usually the largest single line on your closing statement.

Title Insurance and the Collier County Custom

In most Florida counties, including Lee County, the seller customarily chooses the closing agent and pays the owner's title policy. In Collier County the custom flips, and the buyer customarily chooses and pays. Nothing in the statutes fixes this, so the contract controls, and an owner who has sold before in Lee County should confirm the allocation in writing. Florida promulgates the title premium itself under Florida Administrative Code Rule 69O-186.003, so the rate is the same at every title company.

Estoppel Certificates and Their Fees

Under Florida Statutes 720.30851, a homeowners association must issue an estoppel certificate stating the regular assessment, the amount paid through, any balance due and any capital contribution or transfer fee due at closing. The statutory cap set in 2024 is $299 per certificate for a current account, $119 more for delivery within three business days and $179 more if the account is delinquent. In Collier County practice the seller customarily pays it.

The Master Working Capital Contribution

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 the Board sets from time to time. It is not an assessment and not a reserve. We could not locate the current Board-set amount in any public document, and no neighborhood-level transfer fee was located either; the estoppel certificate for your home will state what applies, and who pays it is a contract term we settle before signing.

Commission After the NAR Settlement

Since August 17, 2024, offers of buyer broker compensation cannot be advertised in the MLS, buyers sign written agreements with their own agents before touring, and every commission is fully negotiable and not set by law, per the National Association of REALTORS settlement FAQ. What you negotiate with us is the listing side. Whether to offer anything toward the buyer's agent, or a concession toward the buyer's costs, is a separate decision we make together.

A Seller Net Sheet at the Community Median

The proration line is 181 days of the $7,018 median 2026 preliminary total tax for the 366 PUD homes, before any early-payment discount convention.

A Seller Net Sheet at the Santorini Villas Median

Your own net sheet uses your contract price, your own tax bill, your closing date and your estoppel figures, and we build it with you before you sign a listing agreement.

What Must an Olde Cypress Seller Disclose Under Florida Law?

An Olde Cypress seller owes the Florida Statutes 720.401 homeowners association disclosure summary before the buyer signs, because the master association and all nine neighborhood associations are Chapter 720 homeowners associations. Every seller also owes known material facts, the flood disclosure form and the property tax disclosure summary.

The HOA Disclosure Summary Is Owed Before Contract

Florida Statutes 720.401 says a prospective parcel owner "must be presented a disclosure summary before executing the contract for sale," and on a resale the parcel owner, not a developer, supplies it. The contract itself must carry the statutory voidability language in conspicuous type. If the summary is not delivered, the buyer may void the contract "within 3 days after receipt of the disclosure summary or prior to closing, whichever occurs first," and that right cannot be waived. Getting the timing wrong hands your buyer an exit that lasts until the closing table.

Who Owes What in an Olde Cypress Sale

The documented split is simple. You, the seller, owe the disclosure summary before the contract is signed. The master association's working capital contribution under Section 8.13 is collected at the transfer of title. The public documents we read do not show the Olde Cypress declaration restating the 720.401 duty, so this page does not claim it does; the statute alone sets the duty. This is general information, not legal advice; your closing agent or attorney confirms it for your contract.

Fairway Preserve Is a Different Regime

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 and is a Chapter 718 condominium, where the 720.401 summary does not apply and the condominium resale package does. This page serves the 548 single-family homes behind the Treeline Drive gate; a Fairway Preserve seller should work from the condominium rules with a closing agent or attorney.

Flood Disclosure Under Section 689.302

Since October 1, 2024, Florida Statutes 689.302 requires a residential seller to deliver a flood disclosure at or before the contract, stating whether the seller has filed a flood insurance claim, received federal disaster assistance for flood damage, or knows of flood damage to the property. In Olde Cypress, where 42 FEMA letters of map change have been issued on these streets since 2012, pair the form with your elevation certificate and any letter for your home.

The Property Tax Disclosure Summary

Florida Statutes 689.261 requires a property tax disclosure summary warning the buyer not to rely on the seller's current taxes, because the assessment resets after a sale. On the 2026 preliminary roll the gap between a homesteaded and a non-homesteaded median bill inside the PUD is $6,361 against $9,176, which is exactly the reset that summary warns about.

Known Defects and the Johnson v. Davis Duty

Florida law requires a seller of a home to disclose known facts that materially affect its value and are not readily observable, under Johnson v. Davis, 480 So. 2d 625 (Fla. 1985). Past roof leaks, storm repairs, permits never closed and water intrusion belong in the disclosure. Answer every question completely; a buyer who finds an undisclosed defect after closing has remedies, and a disclosed one is simply part of the price.

How Does Flood Zone Affect Selling an Olde Cypress Home?

Flood zone affects an Olde Cypress sale through the buyer's lender and insurer. On FEMA's effective May 16, 2012 maps much of the community sits in Zone AH, shallow ponding, while FEMA's March 20, 2025 preliminary map shows every home inside the Olde Cypress PUD in Zone X. The preliminary map is not effective, and Lantana reads differently.

Data updated: September 2026 (FEMA National Flood Hazard Layer, effective and preliminary, overlaid on Collier County building footprints, computed September 23, 2026; Collier County August 2026 release)

The Effective 2012 Map, Neighborhood by Neighborhood

Source: FEMA's effective National Flood Hazard Layer, panels 12021C0211H to 0214H, overlaid on Collier County's building footprints. "Partly" means any overlap at all, even a lanai corner. Every FEMA letter we read names the flooding source as ponding and overland flow, not the Gulf.

Lantana's 2013 Letter and the Preliminary Map

FEMA's LOMR-F 13-04-6118A, issued August 8, 2013, removed Lantana Lots 1 through 122 from the Special Flood Hazard Area to unshaded Zone X, even though the map graphic still paints them in Zone AH. On the preliminary map, 72 of Lantana's 122 footprints would touch newly mapped Zone AH, and whether FEMA revalidates the 2013 letter has not been announced. A Lantana seller should hand the buyer the letter and know both stories.

What the Preliminary Map Means for the Other Eight Neighborhoods

For the 366 homes inside the Olde Cypress PUD, the preliminary map draws no Special Flood Hazard Area at all: 274 footprints touch Zone AH today, and zero would. Collier County opened the 90-day appeal period on August 19, 2026, with the new map targeted for summer 2027, per its August 2026 release. Until then, the 2012 map governs lending, and a seller should not market a draft.

Letters of Map Amendment on These Streets

Forty-two Letters of Map Change have been issued since 2012 for property on these streets, almost all reading "Structure removed," and Collier County holds 65 elevation certificates for them. If your home partly touches Zone AH on the 2012 map and you have no letter, a licensed surveyor can tell you whether one is worth applying for before you list. The most recent letter we found, 25-04-6753A, was issued September 29, 2025 for a Lone Pine Lane home.

The Documents That Settle a Buyer's Lender

Put the elevation certificate, any LOMA or LOMR-F for your address and a current flood quote in the listing file before the first showing. The lender's flood determination for the specific building decides whether flood insurance is required, and a buyer who has that answer on day one does not stall a contract waiting for it.

How Do Hurricanes and Building Age Affect an Olde Cypress Sale?

Olde Cypress sits in Collier County Evacuation Zone E and Florida's Category 4 storm surge zone, about 6.7 miles inland, with no Coastal High Hazard Area or Zone VE. What a buyer's insurer prices is the wind: a 160 mph design wind speed for houses, the roof date and the opening protection on each home.

Data updated: September 2026 (Collier County hurricane evacuation zone and Florida Building Code wind load layers; Florida Division of Emergency Management storm surge zones; Collier County building footprints 2000 to 2025)

Evacuation Zone E and the Surge Picture

Every home point tested falls in Evacuation Zone E on Collier County's hurricane evacuation zone layer, one of the outer tiers called only in larger-surge scenarios, and in the Category 4 zone on the state's storm surge zone map. For a buyer comparing Olde Cypress with a coastal address, that is a real difference, and your listing can say so with the sources.

160 mph and the Replacement Standard

Collier County's Florida Building Code 8th Edition layers put the ultimate design wind speed for Risk Category II buildings, which includes houses, at 160 mph at Olde Cypress. At that speed the community sits inside the wind-borne debris region by our reading of the code, so replacement windows and doors generally have to be impact-rated or protected by approved shutters. A home that already has impact glass on every opening is ahead of that requirement, and the buyer's insurer will credit it.

The Build Era, Home by Home

About 155 of the 366 homes inside the Olde Cypress PUD already appear in the 2000 or 2002 aerial footprint layers, so they were likely permitted before the first statewide Florida Building Code took effect in 2002. Da Vinci Estates was built mostly from 2004 to 2013, and Lantana from 2013 to 2016. A pre-2002 home is not a weak home, but its insurer will want the re-roof permit, the wind mitigation form and the opening protection documented.

The Claims Record Near Olde Cypress

The Census block group that contains Olde Cypress shows only 3 NFIP flood claims ever in FEMA's OpenFEMA claims dataset, none of them coded to Hurricane Ian, and we found no news or county report naming Olde Cypress for structural or flood damage in Irma or Ian. Absence of a report is not proof of no damage: answer the storm and repair questions on your disclosure completely, and keep the invoices and permits for the buyer.

What Will Your Buyer Pay to Own an Olde Cypress Home?

Your buyer will underwrite a quarterly neighborhood invoice that includes the master share, mandatory club social dues, optional golf, property taxes at the 2025 rate of 9.5058 mills with no CDD, flood insurance where the lender requires it, and a homeowners policy priced on the roof and openings. None of the association or club amounts is published.

Data updated: September 2026 (Olde Cypress Master Property Owners Association About page; 2025 Collier County Tax Collector bill; Collier County Property Appraiser 2026 preliminary roll; OpenFEMA NFIP policies as of September 8, 2026)

The Quarterly Neighborhood Invoice

Owners receive quarterly invoices from their neighborhood association that include the neighborhood costs plus the owner's share of the master association, per the master association's About page. That fee covers the common grounds, landscaping, streetlights, signage, paving and stormwater, and basic exterior landscaping of each home. The dollar amount differs by neighborhood and is published only on the resident portal, so the estoppel is the reliable figure.

Club Dues Set by the Club

Social dues are payable "as promulgated by The Club ... from time to time," under Section 14.02, which means the club, not the association, sets the amount. Golf initiation and dues are separate and optional. We ask the club's membership office at (239) 596-4797 for the current written figures before your listing goes live, so a buyer's agent is not quoting a portal.

The Tax Reset Your Buyer Inherits

The gap is mostly the Save Our Homes cap. A buyer does not inherit the seller's cap: the year after purchase, the assessed value resets toward the just value, and the buyer's first full bill is usually higher than yours. The 2025 millage rate was 9.5058 mills, per the 2025 Collier County Tax Collector bill for a Lone Pine Lane home.

No CDD on the Tax Bill

Olde Cypress has no Community Development District. Collier County's CDD layer shows none over the community, the state's dissolved districts list shows none past, and the only non-ad valorem line on the sampled 2025 bill was District 1 Garbage at $261.91. Older descriptions that claim a CDD are wrong, and your listing can correct them with the sources.

Flood Insurance Context

The OpenFEMA NFIP policies dataset, as of September 8, 2026, shows a median single-family flood policy cost of $1,259 a year in ZIP 34119, and $1,265 in the block group that contains Olde Cypress, where only 38 of 613 policies carry the mandatory-purchase flag. Unincorporated Collier County is a Community Rating System Class 5 community, worth a 25 percent NFIP discount inside the Special Flood Hazard Area and 10 percent outside it.

Which Olde Cypress Rules Affect a Sale?

The Olde Cypress rules that affect a sale are the leasing limits, the two-step architectural review, the overnight parking rule, the lake and preserve easements, and the realtor sign and open house rules. A buyer's agent will ask about each, so the answers belong in your listing file with the recorded source.

Leasing: 60 Days, Four a Year, Board Approval

Under Section 9.13 of the restated declaration and the 2013 leasing amendment recorded at OR 4874 PG 3783, no lease may run under 60 days and no home may carry more than four leases in a calendar year. The whole home only, a $100 application fee, a $1,000 refundable common area deposit, and a Board decision within 5 business days or the application is deemed denied. Seasonal rental works; short-term vacation rental does not, and investor buyers will ask.

Selling With a Tenant in Place

A lease in place transfers with the home unless the contract says otherwise, and a buyer who wants to move in needs its end date. Because leases here run at least 60 days, time a sale around the lease calendar and share the lease and the association approval with the buyer's agent early.

Architecture, Lakes and the Parking Rule

Exterior changes need approval from both the neighborhood and the master architectural committees (Article X). No boats or swimming on the lakes, a 20-foot lake maintenance easement from the top of bank, and conservation buffers that may not be altered (Sections 9.11, 6.05 and 11.04). And no vehicles may be parked on Olde Cypress streets overnight, with no more than two cars in a driveway. A buyer planning a pool extension or a third car should hear about these before the inspection period ends.

Pets

Section 9.18 allows common household pets such as dogs, cats and birds, leashed outdoors and not left tethered on porches, lanais or in garages. Livestock, poultry and reptiles are prohibited, and the Board can remove a nuisance pet.

How Long Does It Take to Sell an Olde Cypress Home?

The median Olde Cypress home sold after 29 days on market in the twelve months to September 26, 2026, and 27 days over 48 months. Add about 30 to 60 days for the contract, inspections, the estoppel and a financed closing. The range is wide: 0 days for the fastest sale of the year and 293 for the slowest.

Data updated: September 2026 (Southwest Florida MLS Matrix, closed September 27, 2022 to September 26, 2026, pulled September 26, 2026)

When Olde Cypress Homes Actually Closed

Sixty-three of the 107 closings, about 59 percent, landed from January through May. A home that goes live in November or December meets the season's buyers as they arrive; a home listed in April is racing the end of it.

A Realistic Sequence

Two to four weeks to prepare: the valuation, the pre-listing inspection and wind mitigation report, the club's written figures, the estoppel request and the flood file. Then the market period, which has run from days to several months depending on price. Then a contract period of 30 to 60 days. Plan backward from the date you need to close.

Selling While You Are Up North

About three in ten homes inside the PUD are not homesteaded, so many Olde Cypress sellers sell from somewhere else. Marc Comisar handles access through the gate, contractors, inspections and the final walkthrough, and a Florida closing can be completed by mail or remote notary.

What Should Your Listing Say About Life at Olde Cypress?

Your listing should say what the buyer cannot find on a portal: a P.B. Dye course opened in 1999 with an island-green 12th, a clubhouse renovated in 2025 and 2026, one quiet gate, A-rated assigned schools on every street, and a location 1.6 road miles from I-75. Each of those is a sourced fact, not an adjective.

The Course and the Renovated Clubhouse

The course is 18 holes, par 72, a P.B. Dye design that Golfweek reported as the first in Collier County, with all 18 greens resurfaced and all 98 bunkers rebuilt in 2021. The club's scorecard runs from 6,711 yards to 4,132. Social members use the clubhouse, dining, four clay tennis courts, two pickleball courts, a fitness center and the pool.

Schools: Every Street Assigned to A-Rated Schools

Every single-family street, 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. All three earned an A in 2024, 2025 and 2026, as republished from Florida Department of Education data by the Naples Daily News.

Location, Entrance and Drive Times

The only entrance is Treeline Drive at Logan Boulevard North, about a quarter mile north of Immokalee Road. From there it is about 1.6 road miles to I-75 Exit 111, about 2.4 miles to NCH Emergency Department Northeast and about 14.5 miles to Fifth Avenue South downtown, on a free-flow routing model. The clubhouse sits outside the residential gate, so club traffic stays out of the neighborhoods.

How Do You Get a Free Olde Cypress Home Valuation?

You get a free Olde Cypress home valuation by requesting one online or calling Jesse McGreevy at (239) 898-6072. It is a written opinion of value built from the recorded and MLS sales of your own neighborhood, view and size, with your buyer's club, fee and tax picture beside it. No cost, and no obligation to list.

What a McGreevy and Comisar Valuation Includes

You receive the county and MLS sales for your neighborhood with their dates and sources, a price per square foot analysis that never mixes county base area with MLS living area, the live competition with price histories, the club's written figures and your estoppel items, your flood zone and any FEMA letter on file, and a recommended list price with a defensible range. Request it through our Olde Cypress home valuation request or the McGreevy and Comisar valuation form.

How to Reach Us Today

Call Jesse McGreevy direct at (239) 898-6072 or email [email protected]. Call Marc Comisar at (239) 287-5873. The office of McGreevy and Comisar is at 24031 S Tamiami Trl #101, Bonita Springs, FL 34134. Bring your address, your neighborhood, your timeline and the one thing you are most worried about, and you will get a straight answer.

Why the Valuation Comes Before the Listing Agreement

Few homes in any one Olde Cypress neighborhood come up for sale in a year: Egret Cove, Strada Bella and Biscayne Place recorded none in the last twelve months. The owner who sells next should see the evidence and the number before committing to anything, and should call us first, because the next sale in a thin neighborhood sets the comparable for everyone after it.

What Do Sellers Say About Working With McGreevy and Comisar?

McGreevy and Comisar are a top-reviewed listing team on Google, and the quotes below are genuine five-star client reviews that any Olde Cypress seller can check on that profile, reproduced in each reviewer's own words. We publish no aggregate score and no star-rating widget. Read the full set on the McGreevy and Comisar Google reviews profile.

A Seller on Pricing Judgment

★★★★★ "Their recommendation on pricing my unit was sound and proved prescient. I never questioned their integrity and found it easy to rely on their recommendations. I would work with them again in a heartbeat." Verified Google review

In a community where the same street closed at 81.72 and 98.08 percent of list in one year, the starting price is the decision.

A Seller Who Did Not Live in the Area

★★★★★ "Not living in the area, Jesse made life easy for me when we decided to sell our condo. His attention to detail, patience, understanding, and tenacity in dealing with all the moving parts was truly impressive." Verified Google review

About three in ten homes inside the Olde Cypress PUD carry no homestead exemption, so many sellers here sell from somewhere else.

A Family Selling a Parent's Home

★★★★★ "Marc made an extremely stressful time of selling my parents' house easier because of his expertise, compassion, and diligence. I cannot thank him enough and I would recommend him without reservation." Verified Google review

A Seller With Thirteen Transactions Behind Them

★★★★★ "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

Why Does an Olde Cypress Specialist Matter When You Sell?

An Olde Cypress specialist matters because the facts that decide a sale here live in documents rather than in a listing feed: a club membership that passes by covenant, fees nobody publishes, a flood map in transition with a Lantana letter the graphic ignores, green-sign and open-house rules at the gate, and nine neighborhoods that do not trade alike.

Jesse McGreevy

Jesse McGreevy is a licensed Florida REALTOR and Sales Associate with Domain Realty, a co-founder of the brokerage and one half of McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008. He started in Southwest Florida real estate in October 2004 and launched the team in October 2008. He runs pricing, marketing, data and the association paperwork. Reach him at (239) 898-6072, and read his profile on the Jesse McGreevy agent page.

Marc Comisar

Marc Comisar is a licensed Florida REALTOR and Broker Associate with Domain Realty and the other half of McGreevy and Comisar. He runs the field side: showings through the gate, buyer agent conversations, inspections and the on-site management that lets an out-of-state owner sell without flying down. Reach him at (239) 287-5873, and read his profile on the Marc Comisar agent page.

What a General Naples Agent Tends to Miss Here

A general agent may price a Lone Pine home off the Olde Cypress median, quote a club figure from a portal, repeat the old CDD claim, market the preliminary flood map as if it were effective, miss the Lantana letter, or put a standard sign in the yard. None of those errors is exotic, and each one costs a seller time or money.

How Olde Cypress Compares With Other Naples Seller Markets

Every Naples golf community sells differently. In Naples Lakes Country Club, every home carries a bundled full membership owned by the homeowners association, as we explain in our guide to selling a home in Naples Lakes Country Club. In Audubon Country Club, membership is mandatory and billed separately, as our guide to selling a home in Audubon Country Club explains. Olde Cypress makes only the social membership mandatory, which changes both the buyer pool and the pitch.

Are You Also Buying Your Next Home in Southwest Florida?

About seven in ten Olde Cypress PUD homes are homesteaded, and a homesteaded seller staying in Florida should treat the sale and the next purchase as one plan. We run both sides together, including the timing of two closings and the Save Our Homes portability claim that can carry accumulated tax savings to a new Florida homestead.

Buying and Selling in the Same Season

A Florida homesteader who sells and establishes a new Florida homestead may transfer accumulated Save Our Homes benefit, within statutory limits, by filing with the new homestead application, and homestead status is fixed on January 1 each year. We sequence both closings around that date. If you are buying, start with how we represent buyers in Naples or call Marc Comisar at (239) 287-5873.

Moving Within the Gates

Some owners move from a Santorini villa to a Lantana home, or from a Da Vinci estate to a smaller home on the golf course. The social membership follows the new deed under the same covenant. If your next home is here, see how we help buyers purchase in Olde Cypress, read the Olde Cypress community guide, and see our Naples real estate guide for the wider city.

Frequently Asked Questions, Seller Edition: Selling a Home in Olde Cypress

These are the questions Olde Cypress owners in North Naples ask before they sell, answered for a Collier County seller, each in one paragraph. They cover price, timing, the club, fees, disclosure, flood and taxes. Nothing here is legal or tax advice; confirm anything that affects your sale with your closing agent, attorney or CPA.

How do I sell my home in Olde Cypress?

Start with a neighborhood-level valuation, then assemble the file an Olde Cypress buyer will ask for: the club's written figures, the estoppel request, your elevation certificate and any FEMA letter, a wind mitigation report and a pre-listing inspection. Launch with professional media and a gate-access showing plan, and negotiate from the recorded evidence. Call Jesse McGreevy at (239) 898-6072 to start.

Who is the best listing agent for Olde Cypress?

The best listing agent for Olde Cypress is one who prices by neighborhood, not by gate, knows the club and flood files, and personally negotiates. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008 and the #1 Team in Southwest Florida since 2012; compare teams on the public record in our guide to the best real estate agents in Naples.

What is my Olde Cypress home worth?

It depends first on your neighborhood: 36-month recorded medians run from $640,000 in Santorini Villas to $2,387,500 in Da Vinci Estates. Then on view, size, lot, roof, openings and condition. Request a written valuation through our Olde Cypress home valuation page or call (239) 898-6072.

What have Olde Cypress homes sold for recently?

In the twelve months to September 26, 2026, the Southwest Florida MLS recorded 26 Olde Cypress closings from $630,000 to $2,990,000 at a median of $1,105,000. The county recorded 24 qualified sales at a $1,142,500 median in the twelve months to its August 29, 2026 file.

How many homes are in Olde Cypress?

The Collier County Property Appraiser 2026 preliminary roll counts 548 single-family homes behind the gate, which the master association rounds to 550, in nine neighborhoods. Fairway Preserve, the 264-unit condominium with its own gate off Immokalee Road, is not part of the gated community.

How many Olde Cypress homes sell in a year?

About two dozen to three dozen. The MLS recorded 26 closings in the latest twelve months and 30 in the twelve before; the county's calendar-year counts since 2016 range from 18 in 2024 to 47 in 2020.

How long does it take to sell an Olde Cypress home?

The median was 29 days on market in the latest twelve months and 27 over 48 months, then about 30 to 60 days to close. Homes priced above their neighborhood's evidence waited far longer: 124, 162, 283 and 293 days in the latest pull.

What is the sold-to-list ratio in Olde Cypress?

97.52 percent in the twelve months to September 26, 2026, against 93.54 percent in the twelve months before, with 6 of 26 closings at or above list.

Is it a buyer's or seller's market in Olde Cypress right now?

With about 2.3 months of supply and a 29-day median, the reading leans to sellers for a well-priced home. But three of five active listings had waited 93 days or more on September 26, 2026, which is the buyer's leverage against an overpriced one.

How does Olde Cypress compare with The Vineyards for a seller?

In the same twelve months, Olde Cypress closed at 97.52 percent of list in a median 29 days; The Vineyards, which mixes condominiums and houses, closed at 94.74 percent in 75 days. Olde Cypress supply was about 2.3 months against about 3.5.

Should I sell now or wait?

Sell when your plans say so, priced to the latest neighborhood evidence. The county median eased from its 2023 peak, but the MLS shows faster sales and a higher sold-to-list in the latest year. Waiting for 2023 prices is a bet, not a plan.

When is the best time of year to sell in Olde Cypress?

January through May: 63 of 107 MLS closings over 48 months landed in those five months. List in November or December to meet the season's buyers as they arrive.

Why is the online estimate for my Olde Cypress home wrong?

Because a model blends nine neighborhoods, cannot see a golf, lake or preserve view, cannot read a FEMA letter and cannot price the club. With about two dozen sales a year, it has too few true comparables.

Does the club membership transfer to my buyer?

Your buyer becomes a social member automatically on acquiring the home, under Section 14.02 of the recorded declaration. Golf membership is a separate purchase from the club, and the club describes its non-equity memberships as non-transferable.

Do I get anything back for my club membership when I sell?

No equity refund exists at a non-equity club: members hold no ownership interest in the club property under Section 14.03. Ask the club's membership office about the treatment of your golf category when you sell.

What do club dues and golf initiation cost?

The club does not publish them. Third-party figures conflict widely, from roughly $45,000 to $175,000 for golf initiation, and none is club-published. We get the current written figures from the membership office at (239) 596-4797 before listing.

Does Olde Cypress have a CDD?

No. Collier County's CDD layer shows none, the state's dissolved-district list shows none, and a sampled 2025 tax bill carried only a $261.91 garbage charge as a non-ad valorem line.

What are the Olde Cypress HOA fees?

Each of the nine neighborhood associations bills quarterly, including the master share, and none publishes the amount outside the resident portal. The estoppel certificate for your home states it.

Who pays the master working capital contribution?

Section 8.13 authorizes collection "at the time of the transfer of title," in a Board-set amount we could not locate publicly. Who pays is a contract term; we settle it before signing, and the estoppel states the amount.

What is an estoppel certificate, and who pays for it?

A statement from your association of what is owed and paid through, under Florida Statutes 720.30851, capped at $299 for a current account, plus $119 for rush delivery. In Collier County practice the seller customarily pays it.

Does the association have to approve my buyer?

The public documents we read require Board approval for leases, not for a sale to an owner-occupant. Confirm your neighborhood's declaration and ask the estoppel request to state any approval requirement.

What must I give my buyer before the contract?

The Chapter 720 homeowners association disclosure summary under Florida Statutes 720.401, before the buyer signs, plus the flood disclosure under 689.302 and the property tax disclosure summary under 689.261.

What happens if I forget the HOA disclosure summary?

The buyer may void the contract within 3 days after receiving the summary or before closing, whichever comes first, and cannot waive that right. Deliver it before the contract is signed.

What must I disclose when selling an Olde Cypress home?

Known facts that materially affect value and are not readily observable, under Johnson v. Davis, plus the statutory forms. Roof leaks, storm repairs, open permits and water intrusion belong on the disclosure.

Is my Olde Cypress home in a flood zone?

On the effective 2012 map, many homes touch Zone AH, shallow ponding; on the March 2025 preliminary map, every home inside the PUD is in Zone X, and Lantana was removed by a 2013 letter. Your address, elevation certificate and lender decide.

Does a FEMA Letter of Map Amendment help my sale?

Yes. A letter removing your structure from the Special Flood Hazard Area answers the lender's question on day one. Forty-two letters have been issued on these streets since 2012.

What hurricane evacuation zone is Olde Cypress in?

Zone E on Collier County's layer, in Florida's Category 4 storm surge zone, about 6.7 miles inland and outside the Coastal High Hazard Area.

Will my buyer's property taxes be higher than mine?

Usually, if you are homesteaded. The 2026 preliminary median inside the PUD is $6,361 for homesteaded homes and $9,176 for others, and the buyer's assessment resets after the sale.

Can I hold an open house or put up a For Sale sign?

Public open houses run Saturday and Sunday, noon to 5 p.m., with signs from the guard house against a $20 deposit, and the only yard sign is the standardized green wooden For Sale sign.

How are showings handled at the gate?

Buyers come with an agent or the owner, or are phoned in to the guard house at (239) 592-5381 by a homeowner. We schedule every showing with the gate in advance.

Can I rent my Olde Cypress home instead of selling?

Yes, within limits: 60-day minimum leases, no more than four a year, Board approval, a $100 application fee and a $1,000 refundable deposit per lease.

Should I sell with a tenant in place?

You can, but the lease transfers with the home unless the contract says otherwise. Share the lease and its end date early, and time the listing around it.

Can I sell my Olde Cypress home by owner?

You can, but you still owe the disclosure summary before contract, the flood and tax disclosures, the estoppel and a gate-access showing plan, and you will price without the comparable file. In a thin market, a pricing mistake can cost more than the commission saved.

Should I take a cash offer instead of listing?

Only if the net is right after you compare it with a listed sale at a 97.52 percent median sold-to-list. A cash offer that saves 30 days but gives up 8 to 10 percent is expensive.

Should I replace my roof or add impact glass before selling?

Get the wind mitigation and four-point reports first. Where the roof or openings will stall a buyer's insurance, a targeted repair can pay for itself; a full renovation rarely does.

Do Santorini villas and Da Vinci estates sell to different buyers?

Yes. Villas sell to a smaller, price-sensitive and often seasonal pool at about 97.68 percent of list after a median 75 days; estates sell to a club-first luxury buyer, and the one Da Vinci Estates listing has waited 162 days.

Is Fairway Preserve part of Olde Cypress?

Not the gated community. It sits inside the Olde Cypress PUD but has its own gate off Immokalee Road, its own condominium declaration and no club social membership.

Where is the Olde Cypress entrance?

Treeline Drive at Logan Boulevard North, about a quarter mile north of Immokalee Road. There is no Olde Cypress Boulevard entrance.

Which schools serve Olde Cypress?

Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for every single-family street for 2026 to 2027, all rated A in 2024, 2025 and 2026.

What does it cost to sell a home in Olde Cypress?

Commission as negotiated, documentary stamp tax at $0.70 per $100 ($7,735 at the $1,105,000 median), the estoppel fees, a lien search and the tax proration. The buyer customarily pays the owner's title policy in Collier County.

What should I do first if I am thinking about selling?

Request a free, written, neighborhood-level valuation and a list of the documents your sale will need. Call Jesse McGreevy at (239) 898-6072 or Marc Comisar at (239) 287-5873.

Sources and Authoritative References

Every Olde Cypress figure on this page traces to a primary source below, listed as of September 2026: the Southwest Florida MLS, the Collier County Property Appraiser roll and recorded sales (cited in plain text), the recorded declarations, the club's own pages, Florida Statutes and FEMA. No listing portal or competing brokerage is cited.

Market data and county records

• Southwest Florida MLS, Matrix (Olde Cypress closed and active listings pulled September 26, 2026; The Vineyards, Longshore Lake, Sterling Oaks and Tiburon pulled September 27, 2026)
• Collier County Property Appraiser 2026 preliminary roll and recorded qualified sales, data file dated August 29, 2026, cited in plain text
• Collier County parcel map layer carrying the 2026 preliminary roll (retrieved September 2026)
• Collier County PUD boundaries layer (retrieved September 2026)
• Collier County building footprint layers, 2000 to 2025 (retrieved September 2026)
• Collier County road centerlines layer (retrieved September 2026)
• Collier County PUD Master List, June 11, 2026 (retrieved September 2026)
• Collier County Tax Collector, 2025 bill for a Lone Pine Lane home (retrieved September 2026)
• Collier County Community Development Districts layer (retrieved September 2026)
• Florida Commerce, dissolved special districts list (retrieved September 23, 2026)

The associations and their recorded documents

• Olde Cypress Master Property Owners Association website (retrieved September 2026)
• Olde Cypress Master Association About page on the nine neighborhoods and the quarterly fee (retrieved September 2026)
• Olde Cypress Master Association documents library (retrieved September 2026)
• Olde Cypress realtors information page, open house and sign rules (retrieved September 2026)
• Olde Cypress Master Association contact page (retrieved September 2026)
• 2019 Amended and Restated Declaration for Olde Cypress, OR 5700 PG 1118 (retrieved September 2026)
• 2013 leasing amendment for Olde Cypress, OR 4874 PG 3783 (retrieved September 2026)
• Olde Cypress neighborhood site map with the gate house (retrieved September 2026)
• Olde Cypress community access and gate procedures (retrieved September 2026)
• Olde Cypress lake management document (retrieved September 2026)
• Terramar at Olde Cypress declaration of covenants (retrieved September 2026)
• Strada Bella declaration of covenants (retrieved September 2026)
• Da Vinci Estates governing documents (retrieved September 2026)
• Lantana declaration of covenants (retrieved September 2026)
• Biscayne Place declaration, articles and bylaws (retrieved September 2026)
• Santa Rosa at Olde Cypress 2011 amended declaration (retrieved September 2026)
• Santorini Villas combined governing documents (retrieved September 2026)
• Egret Cove amended governing documents (retrieved September 2026)
• Olde Cypress Homeowners' Association 2016 amended declaration (retrieved September 2026)

The Club at Olde Cypress

• The Club at Olde Cypress website (retrieved September 2026)
• The Club at Olde Cypress membership page (retrieved September 2026)
• The Club at Olde Cypress About Us page and FAQ (retrieved September 2026)
• The Club at Olde Cypress real estate page (retrieved September 2026)
• The Club at Olde Cypress renovation page (retrieved September 2026)
• The Club at Olde Cypress scorecard (retrieved September 2026)
• Five things to know about Naples private golf clubs, with the private cart fee (retrieved September 2026)
• Equity vs. non-equity golf club memberships at Olde Cypress (retrieved September 2026)
• The Club at Olde Cypress directions (retrieved September 2026)
• Business Observer, March 6, 2026, on the first phase of the $16 million renovation (retrieved September 2026)
• Club + Resort Business, April 28, 2026, on the Greenside Grille debut (retrieved September 2026)
• Golfweek, September 29, 2021, on the Olde Cypress course renovation (retrieved September 2026)
• Florida State Golf Association club record for The Club at Olde Cypress (retrieved September 2026)

Florida statutes and state agencies on selling

• Florida Statutes 201.02, documentary stamp tax on deeds (retrieved September 24, 2026)
• Florida Department of Revenue, documentary stamp tax (retrieved September 24, 2026)
• Florida Statutes 720.401, homeowners association disclosure summary, Florida Senate (retrieved September 2026)
• Florida Statutes 720.30851, homeowners association estoppel certificates (retrieved September 24, 2026)
• Florida Statutes 689.261, property tax disclosure summary (retrieved September 24, 2026)
• Florida Statutes 689.302, flood disclosure in residential sales (retrieved September 23, 2026)
• Florida House staff analysis of HB 979 (2024), estoppel fee caps (retrieved September 24, 2026)
• Florida Administrative Code Rule 69O-186.003, title insurance rates (retrieved September 24, 2026)
• Florida Department of Financial Services, title insurance overview (retrieved September 24, 2026)
• Internal Revenue Service, FIRPTA withholding (retrieved September 24, 2026)
• Johnson v. Davis, 480 So. 2d 625 (Fla. 1985) (retrieved September 24, 2026)
• National Association of REALTORS, settlement frequently asked questions (retrieved September 24, 2026)
• National Association of REALTORS, written buyer agreements (retrieved September 24, 2026)

Flood, storm and insurance

• FEMA National Flood Hazard Layer, effective panels 12021C0211H to 0214H (queried September 23, 2026)
• FEMA preliminary National Flood Hazard Layer, panels issued March 20, 2025 (queried September 23, 2026)
• FEMA LOMR-F 13-04-6118A for Lantana Lots 1 to 122 (retrieved September 2026)
• FEMA LOMA 12-04-5230A for Strada Bella and Terramar lots (retrieved September 2026)
• FEMA Flood Map Service Center (retrieved September 2026)
• Collier County 2013 elevation certificate for a Lantana Circle home (retrieved September 2026)
• Collier County August 2026 release on the proposed Flood Insurance Rate Map (retrieved September 2026)
• Collier County 2026 flood protection newsletter (retrieved September 2026)
• Collier County Building Bulletin 21, surveys and elevation certificates (retrieved September 2026)
• OpenFEMA NFIP policies dataset (as of September 8, 2026)
• OpenFEMA NFIP claims dataset (retrieved September 2026)
• OpenFEMA NFIP Community Status Book (retrieved September 2026)
• Collier County hurricane evacuation zones layer (retrieved September 2026)
• Florida Division of Emergency Management, Collier County storm surge map (retrieved September 2026)
• Florida Division of Emergency Management, Collier County evacuation map (retrieved September 2026)
• Collier County ArcGIS map services, including building code wind load layers (retrieved September 2026)
• National Weather Service Miami, Hurricane Irma report (retrieved September 2026)
• Citizens Property Insurance, detail by county, August 31, 2026 (retrieved September 2026)

Schools and location

• Collier County Public Schools address lookup for an Olde Cypress Drive address (retrieved September 2026)
• Naples Daily News report on 2026 Collier school grades, July 22, 2026 (retrieved September 2026)
• Florida Department of Education school grades (retrieved September 2026)
• NCH Emergency Department Northeast (retrieved September 2026)
• OSRM routing engine used for free-flow drive times (retrieved September 2026)

Our related pages

• Olde Cypress community guide
• The Vineyards community guide
• Naples real estate guide
• The best real estate agents in Naples, compared
• How we represent buyers in Naples
• Jesse McGreevy agent profile
• Marc Comisar agent profile
• Domain Realty Group
• McGreevy and Comisar Google Business Profile

Downloadable Documents

Every row below links the authority that publishes the document, so an Olde Cypress seller or buyer always sees the official, current version rather than a copy. We host nothing ourselves, and the documents that are not public are named at the end with the office that holds each.

Documents that matter to an Olde Cypress sale but are not public: the club's current social dues and golf initiation and dues, from the membership office at (239) 596-4797; your neighborhood association's budget and quarterly assessment, from the resident portal or the manager; the master working capital contribution amount; and the estoppel certificate for your home.

Your Olde Cypress Listing Team, and How to Reach Us Today

McGreevy and Comisar list and sell homes across Southwest Florida from an office in Bonita Springs, and Olde Cypress sits inside the North Naples market we work every week. Few homes in any one Olde Cypress neighborhood come up for sale in a year, so the owner who sells next should call us first.

The Accolades, Verbatim

• 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

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.

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).

McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team; learn more at DomainRealtyGroup.com, and read about the partnership on our about McGreevy and Comisar page. Nothing on this page is legal, tax or insurance advice.

Market data from Southwest Florida MLS, pulled September 26, 2026, and from the Collier County Property Appraiser 2026 preliminary roll and recorded qualified sales, data file dated August 29, 2026. Brokered by Domain Realty.