Santa Rosa at Olde Cypress is 27 detached homes on Monteverde Way and Olde Cypress Drive in gated Olde Cypress, Naples, every lot on the golf course, with four MLS sales since 2022 from $1,229,000 to $1,825,000. Sell or buy with McGreevy and Comisar.
Santa Rosa at Olde Cypress is a single-family neighborhood inside the master-planned community of Olde Cypress in Naples, Florida. It is 27 detached homes, 26 on Monteverde Way and one on Olde Cypress Drive, and every one of the 27 lots backs onto the P.B. Dye golf course, which no other Olde Cypress neighborhood of its size can say. Santa Rosa is also one of the rarest trades behind the Treeline Drive gate: four Southwest Florida MLS closings in the 48 months to September 26, 2026, from $1,229,000 to $1,825,000. McGreevy and Comisar are the team Santa Rosa sellers should call first, and the team Santa Rosa buyers should call when they want the full record behind a price. 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.
A word on the name, because search engines blur it. This guide covers Santa Rosa at Olde Cypress Homeowners' Association, Inc. on Monteverde Way in North Naples, ZIP 34119. It is not Santa Rosa County in the Florida Panhandle, not Santa Rosa Beach in Walton County, not Santa Rosa Island off Pensacola Beach, and not Santa Rosa, California. It is also not Fairway Preserve at Olde Cypress, the 264-unit condominium off Immokalee Road that carries the Olde Cypress name but sits outside the gate and outside the master association.
If you own on Monteverde Way and are weighing a sale, start with the market record and the seller section, then call Jesse. If you are buying, the lot, flood, fee and rules detail below will tell you whether Santa Rosa fits before you tour, and why a single sale can move this neighborhood's numbers more than any other in Olde Cypress.
By Jesse McGreevy and Marc Comisar, McGreevy and Comisar, Domain Realty Group. Updated September 2026.
McGreevy and Comisar are the best realtor for Santa Rosa at Olde Cypress because the case rests 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 a Santa Rosa read built from every MLS closing since 2022 and every county-recorded sale since 2001.
If you're searching for the best realtor for Santa Rosa at Olde Cypress in Olde Cypress, Naples, whether you're ready to sell your Santa Rosa at 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.
That matters in Santa Rosa for a reason specific to Monteverde Way. With 27 homes and roughly one resale a year, there is almost never a fresh comparable on the same street, so a Santa Rosa price has to be built from four MLS closings, a 25-year county record and the Olde Cypress neighborhoods around it, such as Lantana at Olde Cypress. Every lot here backs onto the golf course, so size, condition, orientation and flood paperwork separate one home from another.
Recent Santa Rosa at Olde Cypress track record (last 12 months): In the last 12 months Santa Rosa at Olde Cypress has seen 2 resales in the Southwest Florida MLS Matrix (retrieved September 26, 2026, closings September 27, 2025 to September 26, 2026): $1,512,500 on December 2, 2025 and $1,600,000 on December 4, 2025, $3,112,500 in total volume. The highest-priced Santa Rosa sale in that window was $1,600,000, for a 2,898 square foot home with four bedrooms and a den. The two sold at 96.03% and 98.46% of their final list prices, after 7 and 34 days on market. Two sales are a small sample, so we list them rather than turn them into a median. The Matrix pull we worked from did not carry listing offices, so we state no represented-sale count for Santa Rosa.
We tracked every one of the 4 Santa Rosa closings in the Southwest Florida MLS since September 2022, and all 44 Collier County recorded qualified sales on Monteverde Way since 2001, before writing a word of this guide; each is listed below.
For Santa Rosa sellers: premium marketing, including cinematic video, drone, professional photography, a qualified-buyer database, and discretion with off-market capability when a sale needs to stay quiet. On Monteverde Way the drone matters most, because the fairway behind the lanai is what every buyer is paying for. The marketing must also reach beyond Naples: 7 of the 27 homes carry an out-of-state owner mailing address on the 2026 preliminary roll.
For Santa Rosa buyers: the first question is size, because the four MLS sales ran from 2,551 to 4,044 square feet of living area and the price followed. The second is flood paperwork, because the footprints split three ways on the effective FEMA map. The third is the club, whose social membership comes with every home. Sellers and buyers comparing the best real estate agents in Naples should ask each one to answer those three questions for a specific Santa Rosa address; we answer them below.
Honors and recognition:
Selling your Santa Rosa at Olde Cypress home? Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072.
Buying a home in Santa Rosa at Olde Cypress? Call Marc at (239) 287-5873 for a personalized buyer consultation, or read our Santa Rosa at Olde Cypress buyer's guide.
Living in Santa Rosa at Olde Cypress means a detached golf-course home on a quiet interior street, one staffed gate at Treeline Drive, basic exterior landscaping handled through the association invoice, and automatic social membership in The Club at Olde Cypress, in a 27-home Naples neighborhood where resales are rare.
Santa Rosa at Olde Cypress is one of nine neighborhood associations under the Olde Cypress Master Property Owners Association, and on the 2026 preliminary roll its own recorded plat of 27 single-family homes. The master association's Olde Cypress Neighborhood Site Map colors Santa Rosa as one of the nine and places the single gatehouse on Treeline Drive, just east of Logan Boulevard North.
The governing corporation is Santa Rosa at Olde Cypress Homeowners' Association, Inc., Florida document N01000002469, filed with the Division of Corporations on April 9, 2001 and active, per the Sunbiz search for Santa Rosa at Olde Cypress. On the 2026 preliminary roll the association holds title to the neighborhood's road tract, about 1.04 acres.
Twenty-six of Santa Rosa's 27 homes sit on Monteverde Way, a short street that connects only to Olde Cypress Drive, the community's interior spine, per Collier County's road centerline layer. The 27th Santa Rosa home is platted in the neighborhood but addressed on Olde Cypress Drive itself. Only residents, guests and service vehicles drive it.
Monteverde Way sits mid-community; Terramar at Olde Cypress, its closest match on lot size, lies nearer the Logan Boulevard side.
On the county's parcel polygons, all 27 Santa Rosa lots sit within 10 feet of the golf course parcel, a 100 percent golf-adjacent count shared only by Terramar (55 of 55), Egret Cove (18 of 18) and Biscayne Place (8 of 8). The course is private land owned by the Stock-affiliated Olde Cypress Development, not common area; lanai orientation and distance to the nearest tee or green differ lot by lot.
The roll describes ownership, not people. On the 2026 preliminary roll 18 of the 27 Santa Rosa homes (66.7%) carry a Florida homestead exemption, close to the roughly seven in ten across the Olde Cypress zoning district, and seven owners receive their tax bill in another state. The likely buyer pool therefore includes both full-time Naples residents and second-home buyers, and the marketing has to reach both.
The last two Santa Rosa MLS closings were $1,512,500 and $1,600,000 in December 2025, and the four since September 2022 ran from $1,229,000 to $1,825,000. No Santa Rosa home was listed for sale or pending on September 26, 2026. A buyer who wants Monteverde Way therefore needs a plan for waiting, not just a budget.
Santa Rosa has no neighborhood clubhouse, pool or courts of its own in the records we read; amenities come through the master association and The Club at Olde Cypress. It has no attached product, no new construction, no vacant homesites and no community development district, and every lot is classed as golf-adjacent on the county map. It also has no published fee schedule.
Santa Rosa at Olde Cypress homes closed four times in the Southwest Florida MLS in the 48 months to September 26, 2026: $1,825,000 in February 2023, $1,229,000 in April 2024, $1,512,500 and $1,600,000 in December 2025. No window reaches ten sales, so every sale is listed below instead of a median.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Where no MLS window holds ten or more closings, we show every sale. Santa Rosa never reaches ten: 2 closings in 12 and 24 months, 3 in 36 and 4 in 48, the widest MLS pull. For the record, the 48-month midpoint is $1,556,250, the mean of the middle pair $1,512,500 and $1,600,000, a small sample. The long view comes from 44 county-recorded sales since 2001.
Close date | Street | Bedrooms and baths | Living sq ft | Final list price | Sold price | Sold $ per living sq ft | Sold to final list | Days on market |
|---|---|---|---|---|---|---|---|---|
December 4, 2025 | Monteverde Way | 4 plus den, 4 full and 1 half | 2,898 | $1,625,000 | $1,600,000 | $552.10 | 98.46% | 34 |
December 2, 2025 | Monteverde Way | 3 plus den, 3 full and 1 half | 2,551 | $1,575,000 | $1,512,500 | $592.90 | 96.03% | 7 |
April 8, 2024 | Monteverde Way | 3 plus den, 3 full | 2,946 | $1,329,000 | $1,229,000 | $417.18 | 92.48% | 21 |
February 24, 2023 | Monteverde Way | 4 plus den, 5 full and 1 half | 4,044 | $1,950,000 | $1,825,000 | $451.29 | 93.59% | 34 |
Source: Southwest Florida MLS Matrix, Development OLDE CYPRESS and SANTA ROSA AT OLDE CYPRESS, closings September 27, 2022 to September 26, 2026, retrieved September 26, 2026; each sale assigned to Santa Rosa by street address against the county roll. Total volume $6,166,500. None of the four closed at or above its final list price.
Read together, the four show the most recent sales are the smallest homes at the highest price per square foot: $592.90 for 2,551 square feet in December 2025 against $451.29 for 4,044 square feet in February 2023. Part of that is timing and part is the usual curve, where the first 2,500 square feet of a golf-course home carry the lot and view. A large Santa Rosa home should not be priced at the latest small-home rate.
The two December 2025 sales closed two days and $87,500 apart, with the larger four-bedroom home bringing the higher price but the lower rate per foot.
Nothing. On September 26, 2026 the Southwest Florida MLS Matrix showed no active Santa Rosa listing and no pending or contingent sale. Across all of Olde Cypress on the same date there were 5 active listings and 1 pending, about 2.3 months of supply at the trailing 12-month pace. With zero actives, Santa Rosa's months of supply on the pull date is zero, which is the arithmetic way of saying that the next Santa Rosa listing will have no direct competition on its own street.
Santa Rosa's two closings were 2 of the 26 Olde Cypress MLS closings in the 12 months to September 26, 2026, when the community median was $1,105,000 (the mean of $1,100,000 and $1,110,000), at $472.75 per living square foot, 97.52% of list and 29 days on market (n = 24). Both Santa Rosa sales sat well above that median. We never compare county building areas with MLS living area.
Selling on Monteverde Way? Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.
Santa Rosa at Olde Cypress has 44 Collier County recorded qualified sales since 2001, at an all-history median of $742,500 (the mean of $735,000 and $750,000). The last ten, from January 2018 to November 2025, ran from $675,000 to $1,825,000, and the three most recent were $1,229,000, $1,600,000 and $1,512,500.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
These figures count Collier County Property Appraiser recorded sales marked qualified, for improved homes over $100,000, in the data file dated August 29, 2026. The newest recording anywhere in Olde Cypress in that file is May 22, 2026.
Window to August 29, 2026 | Qualified sales (n) | Median | Range | Label |
|---|---|---|---|---|
12 months | 2 | Two sales, listed: $1,512,500 and $1,600,000 | $1,512,500 to $1,600,000 | Small sample |
24 months | 2 | Same two sales | $1,512,500 to $1,600,000 | Small sample |
36 months | 3 | $1,512,500 (odd n, an observed sale) | $1,229,000 to $1,600,000 | Small sample |
60 months | 5 | $1,512,500 (odd n, an observed sale) | $1,210,000 to $1,825,000 | Small sample |
120 months | 10 | $1,030,000 (even n: mean of $850,000 and $1,210,000) | $675,000 to $1,825,000 | |
All history, since 2001 | 44 | $742,500 (even n: mean of $735,000 and $750,000) |
The 120-month window is the first that reaches ten sales, and its midpoint of $1,030,000 mixes 2018 prices with 2025 prices, so read it as the ten-year center of gravity, not today's value.
Year | Qualified sales | Median recorded price |
|---|---|---|
2001 | 3 | $600,000 |
2002 | 2 | $637,500 |
2004 | 4 | $797,000 |
2005 | 6 | $560,350 |
2006 | 2 | $993,500 |
2009 | 1 | $815,000 |
2010 | 4 | $651,000 |
2012 | 2 | $692,500 |
2013 | 3 | $735,000 |
2014 | 1 | $690,000 |
2015 | 4 | $795,000 |
2016 | 2 | $730,000 |
2018 | 2 | $725,000 |
2020 | 1 | $675,000 |
2021 | 3 | $850,000 |
2023 | 1 | $1,825,000 |
2024 | 1 | $1,229,000 |
2025 | 2 | $1,556,250 |
Source: Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026. Years not shown (2003, 2007, 2008, 2011, 2017, 2019, 2022 and 2026 to the file date) have no qualified Santa Rosa sale. Every year is a small sample; a one-sale year is that sale.
Recorded date | Street | Recorded price |
|---|---|---|
November 26, 2025 | Monteverde Way | $1,512,500 |
November 24, 2025 | Monteverde Way | $1,600,000 |
April 3, 2024 | Monteverde Way | $1,229,000 |
February 17, 2023 | Monteverde Way | $1,825,000 |
November 30, 2021 | Monteverde Way | $1,210,000 |
April 30, 2021 | Monteverde Way | $800,000 |
March 25, 2021 | Monteverde Way | $850,000 |
December 14, 2020 | Monteverde Way | $675,000 |
October 31, 2018 | Monteverde Way | $700,000 |
January 8, 2018 | Monteverde Way | $750,000 |
Source: Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026. Street only; we never publish a house number.
For most of its life Santa Rosa traded in a narrow band: from 2009 through 2020, across 20 recorded sales, every yearly median sat between $651,000 and $815,000. The change came in 2021, and every qualified recording since November 2021 has been above $1.2 million. The 2025 recordings, $1,600,000 and $1,512,500, are roughly double the 2018 to 2020 level, on a handful of sales.
One caution: the 2001 to 2006 sales recorded while the neighborhood was being built, and the county file does not say which were a builder's first sale, so early yearly medians reflect which homes recorded, not the market. The county file also dates the two December 2025 MLS closings as November 24 and 26 recordings; we report each record with its own date.
Pricing a Monteverde Way home against 44 recorded sales? Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.
The most recent Santa Rosa at Olde Cypress sale on the MLS closed December 4, 2025 on Monteverde Way at $1,600,000, 98.46% of a $1,625,000 final list price, after 34 days on market. This is a public-record sale, not one of ours; we walk through it because it is the best current evidence for a Santa Rosa price.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Item | What the record shows |
|---|---|
Street | Monteverde Way |
Home | Four bedrooms plus a den, four full baths and a half bath |
Living area (MLS) | 2,898 sq ft |
Final list price | $1,625,000 |
Sold price | $1,600,000 |
Sold price per living sq ft | $552.10 |
Sold to final list | 98.46% |
Days on market | 34 |
MLS close date | December 4, 2025 |
County recording | $1,600,000, recorded November 24, 2025 |
Sources: Southwest Florida MLS Matrix, retrieved September 26, 2026; Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026.
Two days earlier, a 2,551 square foot Santa Rosa home with three bedrooms and a den closed at $1,512,500 after 7 days, at 96.03% of its $1,575,000 final list. The December 4 sale bought 347 more square feet and a fourth bedroom for $87,500 more, about $252 per added square foot, under half the neighborhood's recent rate. On Monteverde Way, the golf lot carries much of the price.
The December 2025 pair set the current reference: roughly $1.5 million to $1.6 million for about 2,500 to 2,900 square feet, within 4 percent of list. Roof date, impact glass, pool, orientation and flood letter are not in the MLS record and must be adjusted for. A larger home has one data point, three years old, so pricing it is a judgment built from the other Olde Cypress neighborhoods.
Santa Rosa at Olde Cypress holds 27 of the 548 homes behind the Olde Cypress gate, and on September 26, 2026 not one of them was for sale. In a neighborhood where the last four MLS closings sold at 92.48% to 98.46% of their final list price, the seller who prices to the specific lot and size, with the flood letter and the association estoppel already in the file, is the seller who closes near the asking price.
Selling a Santa Rosa at Olde Cypress home? Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072.
Buying in Santa Rosa at Olde Cypress? Call Marc at (239) 287-5873, or read our Santa Rosa at Olde Cypress buyer's guide and how we represent buyers in Southwest Florida.
Santa Rosa at Olde Cypress began as a parcel of the Olde Cypress master plan, which the Stock family partnership started in 1998 and 1999. The Santa Rosa association was filed with the state on April 9, 2001, its declaration was recorded at OR 3057 PG 2810, and the homes went up in two pulses between about 2000 and 2007.
Olde Cypress was built on land first zoned in the older Woodlands planned development. The development partnership, Olde Cypress Development, was formed on September 2, 1998 with a Stock family member as funding partner, per the 1998 Certificate of Limited Partnership. The master declaration was recorded April 27, 1999 at OR 2539 PG 2902, the P.B. Dye course was built that year, and Santa Rosa was built under Ordinance 2000-37, later amended by Ordinances 00-53 and 2011-14.
Santa Rosa was one of the neighborhoods drawn inside that plan. A county development summary dated March 15, 2010, carried in the April 26, 2011 Board of County Commissioners packet, already listed Santa Rosa at 27 homes, the same count the 2026 roll shows.
Santa Rosa at Olde Cypress Homeowners' Association, Inc. was filed with the Florida Division of Corporations on April 9, 2001. The neighborhood's original declaration is recorded in the Collier County Official Records at OR 3057 PG 2810. The recorded pages available to us did not name a homebuilder or a separate declarant for Santa Rosa, and we do not guess at one. By contrast, Terramar at Olde Cypress names Terramar Development, Inc. in its recorded 2000 declaration, and Strada Bella and Biscayne Place name their developer entities too.
The Santa Rosa declaration was restated in 2006 (OR 4144 PG 425) and again in 2011. The current version, the 2011 Amended Declaration, Articles and Bylaws for Santa Rosa at Olde Cypress, is recorded at OR 4722 PG 375 and hosted by the master association. Two restatements in ten years means an older document set may be out of date; the 2011 restatement is the one to read.
Collier County's building footprint layers show when each Santa Rosa home first appears in aerial footprint mapping: two by 2000, seven by 2002 and two by 2004, then fourteen by 2006 and two by 2007. So the neighborhood was built in two pulses, with more than half its homes finished in the 2004 to 2007 stretch. The 2026 roll's year-built field agrees, at 2000 to 2007 with a median of 2005. For a buyer, the practical point is that two Santa Rosa homes a few doors apart can be six or seven years apart in age, with different code eras behind them.
Most Olde Cypress associations list Alliant Property Management of Fort Myers as manager or registered agent. Santa Rosa is one of two exceptions: its state filing lists Moore Property Management, LLC, of St. Petersburg as registered agent. The Santa Rosa estoppel certificate is therefore requested through a different office, and should be checked to confirm it covers the master share billed on the same invoice.
Santa Rosa at Olde Cypress homes are detached single-family golf-course homes built 2000 to 2007, on lots of 8,602 to 16,006 square feet with a median of 9,907. The four MLS sales since 2022 ranged from 2,551 to 4,044 square feet of living area, with three or four bedrooms plus a den.
Santa Rosa lots run 8,602 to 16,006 square feet on the county's parcel polygons, a median of 9,907. That puts Santa Rosa in the middle cluster of Olde Cypress lot sizes with Terramar (median 10,479), Lantana (10,116), Lone Pine Lane (9,785) and Egret Cove (9,618), and well below Da Vinci Estates (18,263) and Biscayne Place (16,680).
Nine Santa Rosa homes first appear in the 2000 or 2002 footprint layers, which means they were likely permitted before Florida's first statewide building code took effect in 2002. Two first appear in 2004, and sixteen in the 2006 to 2009 layers, in the Florida Building Code era. The footprint year is an upper bound on when the house was built, and the date that governs code is the permit date, so a buyer should confirm each home's permit history. The difference matters for insurance: many carriers ask for a four-point inspection on older homes and credit newer code-era construction.
The Collier County Property Appraiser 2026 preliminary roll puts the median Santa Rosa just value at $1,079,324, with a range from $909,013 to $1,886,017 across the 27 homes. Just value is the county's assessment for tax purposes and typically lags the market: the three qualified recordings in the 36 months to August 29, 2026 all sat above that median, at $1,229,000, $1,512,500 and $1,600,000. The spread of just values, roughly two to one from the lowest to the highest, is another sign of how different two Santa Rosa homes can be.
Selling a Santa Rosa home built in the second pulse, or updated since? Those features belong in the price. Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.
A Santa Rosa at Olde Cypress home comes with a private golf-course lot, the master association's gate, roads, lakes and 158.59-acre preserve, and a mandatory social membership in The Club at Olde Cypress, which covers the clubhouse, dining, clay tennis, pickleball, fitness and pool. Golf is a separate, optional membership.
The neighborhood's own common property is its road tract. We found no Santa Rosa pool, clubhouse or courts in the records we read. Basic exterior landscaping of each home is included in the invoice, per the Olde Cypress Master Association About page.
The Olde Cypress Master Property Owners Association runs the staffed gatehouse on Treeline Drive, the private roads beyond it, the stormwater lakes and the master preserve tract of 158.59 acres, all funded through the neighborhood invoice. Golf carts may run on community streets under master association rules (Section 9.31 of the 2019 Amended and Restated Declaration for Olde Cypress), which on Monteverde Way means a cart ride to the clubhouse without leaving private roads.
Section 14.02 of the master declaration makes every Santa Rosa owner a social member of The Club at Olde Cypress "by acquisition of a Parcel." The club's membership page says social membership is "mandatory for all residents of the Olde Cypress community who do not hold a higher category of membership." Social membership covers the clubhouse and dining, the four clay tennis courts with stadium seating and two pickleball courts listed on the club's tennis and racquets page, the fitness center and the pool, but golf only as a golf member's guest. The club is privately owned and non-equity, so owners hold no equity, vote or ownership interest in it (Section 14.03).
The clubhouse was rebuilt between March 2025 and April 2026 in a $16 million project funded by the owner with no member assessment, per the club's renovations page and the Business Observer's March 6, 2026 report.
The course behind every Santa Rosa lot is an 18-hole, par 72 P.B. Dye design built in 1999, playing 6,711 to 4,132 yards on the club's scorecard and renovated in 2021 with new TifEagle greens, drainage and bunkers, per Golfweek's September 29, 2021 report. Golf membership is optional and sold separately; the club publishes no initiation or dues figure (membership office, (239) 596-4797). A private cart on the course costs $1,950 a year, per the club's Five Things to Know article.
Every Olde Cypress home is reached through one entrance, Treeline Drive at Logan Boulevard North, about a quarter mile north of Immokalee Road, with the staffed gatehouse just east of Logan Boulevard. The clubhouse, courts, pool and range sit west of the gate, outside it. The guard house number on the master association's map is (239) 592-5381.
Selling a Santa Rosa home? The club and the golf lot are the features buyers pay for; we document them before the first showing. Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.
Santa Rosa at Olde Cypress owners pay one quarterly invoice from the Santa Rosa association that includes the neighborhood's own costs plus the owner's share of the Olde Cypress master association. The dollar amount is not published outside the resident portal, so the reliable figure is the estoppel certificate for the specific home.
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. The fee covers the common grounds (landscaping, streetlights, signage, paving and stormwater) and basic exterior landscaping of each home. Under Sections 8.03 and 8.04 of the master declaration, the master share is allocated by "Value": each lot counts 1.00, combined lots with one residence count 1.50, and assessments are payable quarterly in advance.
Neither the Santa Rosa association nor the master association publishes a budget or fee schedule outside the resident login, and we do not repeat listing-entered figures, which can be stale or omit the master share.
Three documents replace any estimate with the real number for a specific Santa Rosa home. The estoppel certificate, which under Section 720.30851 of the Florida Statutes must state the regular assessment, its frequency, the amount paid through, any balance due and any capital contribution or transfer fee due at closing; the Santa Rosa association's current adopted budget; and the master association's budget. Ask for all three before the inspection period ends.
Olde Cypress has no community development district. Collier County's Community Development Districts layer lists no Olde Cypress district, the Florida Commerce list of dissolved special districts shows none by that name, and the 2026 preliminary roll carries no non-ad valorem assessment on any Olde Cypress single-family parcel. Santa Rosa's roads, lakes and gate are funded privately through the association invoice, not a bond.
Owning in Santa Rosa at Olde Cypress stacks four layers: the quarterly association invoice, mandatory club social dues, one-time charges at purchase, and property tax, which ran a median $7,692 on the 2026 preliminary roll. Only the tax, the estoppel cap and the club's $1,950 cart fee are published figures; the rest come from documents at contract.
Layer | Amount | How often | Source |
|---|---|---|---|
Santa Rosa association invoice, including the master share | Not published (resident portal only) | Quarterly | Master association About page; estoppel certificate |
Club social membership | Mandatory; dues set by the club and not published | Annual | Master declaration Section 14.02; club membership page |
Club golf membership | Optional; initiation and dues not published by the club | Initiation plus annual dues | Club membership office, (239) 596-4797 |
Private golf cart on the course | $1,950 | Annual, if you choose it | |
Club assessments and food minimum | None, per the club | Not applicable | |
Master working capital contribution | Board-set; current amount not located | Once, at transfer of title | Master declaration Section 8.13 |
Santa Rosa capital contribution or transfer fee | Not located | Once, if the association charges one | 2011 Santa Rosa restatement; estoppel certificate |
HOA estoppel certificate | Up to $299 on a current account | Per sale | Section 720.30851, Florida Statutes |
Property tax | Median $7,692 (2026 preliminary roll, n = 27) | Annual | Collier County Property Appraiser, 2026 tax roll |
Community development district | None | Not applicable | County CDD layer |
Flood insurance | Median $1,259 a year for single-family NFIP policies in ZIP 34119, with Collier's CRS Class 5 discount applied | Annual, where a lender requires it or you choose it | OpenFEMA NFIP policies dataset, September 8, 2026; NFIP Community Status Book |
Every Olde Cypress home sits in the same millage area. A 2025 Collier County Tax Collector bill for an Olde Cypress home shows a total 2025 rate of 9.5058 mills, including 4.2490 for schools and 1.0000 for North Collier Fire, plus District 1 garbage at $261.91. Every $100,000 of taxable value costs about $951 a year.
The Santa Rosa median of $7,692 sits between Terramar's $7,334 and Unit One's $8,438, and mixes long-held capped homesteads with recent buyers, so it is not a buyer's budget.
The year after a sale, the assessed value resets to the just value, so a buyer's bill can be well above the seller's; Section 689.261 of the Florida Statutes requires a disclosure summary saying so before signing. Certified 2026 bills issue in November 2026.
Selling in Santa Rosa? A seller with the estoppel figure, the club dues letter and the budget in hand removes the questions buyers negotiate with. Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.
Santa Rosa at Olde Cypress homes are governed by two recorded layers: the 2011 Santa Rosa restatement (OR 4722 PG 375) and the 2019 Amended and Restated Declaration for Olde Cypress (OR 5700 PG 1118). Where the two differ, the stricter rule generally applies, so a buyer needs both before the inspection period ends.
The master layer is the 2019 Amended and Restated Declaration for Olde Cypress, recorded November 27, 2019 as Instrument 5796524 at OR 5700 PG 1118. The neighborhood layer is the 2011 Santa Rosa restatement. The third is board rules and the master architectural guidelines, posted only on the resident portal. Recorded amendments are searchable in the Collier Clerk's Official Records search.
Any exterior change on a Santa Rosa home, from a new roof color to a pool cage or a hurricane-shutter system, goes through two architectural reviews: first the Santa Rosa association's, then the master association's, and both approvals are required (master declaration Article X). Walls and fences are capped at six feet unless approved, fences and dog runs need approval (Sections 9.09 and 9.25), and private courts need approval (Section 9.32). A seller planning pre-listing work should build the review time into the schedule.
The master rule that surprises buyers most: no vehicles of any kind may be parked on Olde Cypress streets overnight, vehicles are to be garaged overnight, and no more than two cars may sit in a driveway. Golf carts may use community streets under master association rules (Section 9.31), and course carts stay on the course and designated cart paths.
The master association's Realtors Information page sets how a Santa Rosa home is shown: public open houses on Saturday and Sunday from noon to 5 p.m. only, broker opens Monday to Friday, open house signs from the guard house against a $20 refundable deposit, and one standardized green wooden For Sale sign. Outside open house hours, visitors must come with an agent or owner, or be phoned in to the guard house by a homeowner.
Selling in Santa Rosa? We assemble the master and Santa Rosa document packages before listing, so a buyer's attorney is not waiting on them. Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.
Santa Rosa at Olde Cypress is not an age-restricted 55+ community in any record we read. The 2019 master declaration, the master association's own description and the Santa Rosa filings present no housing-for-older-persons designation, and every Monteverde Way address is zoned to public elementary, middle and high schools for 2026-2027.
Under the federal Fair Housing Act, a community may operate as housing for older persons only if it meets specific requirements, including verification of occupancy and published policies showing intent, as the U.S. Department of Housing and Urban Development explains in its fair housing guidance. We found no such designation for Olde Cypress in the documents we read. We describe homes and rules, never who should live in them.
Santa Rosa at Olde Cypress owners can lease, subject to the master rule of a 60-day minimum term and no more than four leasehold interests per parcel per calendar year, with board approval, a $100 application fee and a $1,000 refundable common area deposit. Short-term vacation rental is not permitted.
Rule | What the master documents say |
|---|---|
Minimum lease term | 60 days, in writing |
Maximum leases | No more than four leasehold interests per parcel per calendar year |
What may be leased | The whole parcel only; no subleasing and no room rentals |
Timeshares and home swaps | Count as a lease |
Approval | Board application with credit and background check |
Application fee | $100 per lease |
Deposit | $1,000 refundable common area deposit per lease |
Board deadline | 5 business days, or the application is deemed denied |
Neighborhood rules | Each neighborhood association may add stricter requirements |
Source: Section 9.13 of the 2019 Amended and Restated Declaration for Olde Cypress, carried forward from the 2013 leasing amendment recorded at OR 4874 PG 3783, which raised the minimum from 30 days to 60.
The master rules are the floor. The 2011 Santa Rosa restatement can add its own leasing conditions, and we found no Santa Rosa leasing summary outside the resident portal, so read the restatement and get the association's current application before signing a tenant. Seasonal rental works under these rules; weekly vacation rental does not.
Santa Rosa at Olde Cypress owners may keep common household pets such as dogs, cats and birds under Section 9.18 of the Olde Cypress master declaration. Pets must be leashed outdoors and may not be left unattended or tethered on porches, lanais, common areas or in garages; livestock, poultry and reptiles are prohibited.
The master board can require removal of a pet that becomes a nuisance. The Santa Rosa restatement can be stricter than the master rule on number or size, so a buyer with a large dog or several pets should read it before contract. Fences and dog runs need both architectural approvals, which matters on a golf lot where the rear yard opens to the course.
Santa Rosa at Olde Cypress is a mandatory homeowners association governed by Chapter 720 of the Florida Statutes, not a condominium. On a resale, the seller must give the buyer the Section 720.401 disclosure summary before the contract is signed; without it, the buyer may cancel before closing.
Section 720.401 of the Florida Statutes requires that a prospective buyer in a mandatory homeowners association receive a disclosure summary, before signing the contract, stating that membership is mandatory, that recorded covenants govern the use of the property, and that assessments are owed and may change. If the summary is not provided first, the contract is voidable by the buyer, who may cancel by written notice within 3 days after receiving it or before closing, whichever comes first. That cancellation right cannot be waived. In Santa Rosa the summary should cover both the Santa Rosa association and the master association.
Under Section 720.30851, the association must issue an estoppel certificate on request stating what is owed. The statutory fee is capped at $299 on a current account, with an extra $119 for expedited delivery and $179 if the account is delinquent, per the 2024 House staff analysis of HB 979. Because the Santa Rosa invoice includes the master share, the Santa Rosa certificate should state both, and the closing agent should confirm it does; the seller customarily pays the estoppel fee in Collier County.
Chapter 720 gives Santa Rosa owners rights to inspect official records and attend board meetings with notice; the text is in Chapter 720 of the Florida Statutes. The condominium milestone-inspection and reserve-study rules do not apply; there are no condominiums behind the Olde Cypress gate.
Santa Rosa at Olde Cypress sits on FEMA maps effective May 16, 2012 that place 12 of its 27 home footprints wholly in Zone AH, a shallow ponding zone, 11 partly and 4 wholly in Zone X. FEMA's preliminary map issued March 20, 2025 places all 27 in Zone X, but that map is not yet effective.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
The effective Flood Insurance Rate Map for Olde Cypress is the countywide map for unincorporated Collier County (community 120067), panels 12021C0211H through 12021C0214H, all effective May 16, 2012, per FEMA's National Flood Hazard Layer. Every FEMA letter pulled for an Olde Cypress address names the flooding source as ponding and overland flow, rain that collects in low ground, not Gulf surge. FEMA's definition of Zone AH is shallow flooding, usually ponding, generally one to three feet deep, with a base flood elevation; it is a Special Flood Hazard Area.
We overlaid each Santa Rosa home's building footprint from Collier County's 2025 layer on FEMA's effective zones.
Test | Santa Rosa result (27 homes) |
|---|---|
Footprint wholly in Zone AH | 12 |
Footprint partly in Zone AH (any overlap, even a sliver) | 11 |
Footprint wholly in Zone X | 4 |
Nearest base flood elevation lines | 12.0 to 12.5 ft NAVD88 |
Footprints touching Zone AE | None |
Two test points on Monteverde Way a short distance apart show how fine the line is: one sits 100% in Zone AH near a 12.5-foot base flood elevation line, the other 100% in unshaded Zone X near a 12.0-foot line. A neighbor's answer is never yours.
Three Monteverde Way homes hold FEMA Letters of Map Amendment removing the structure from the Special Flood Hazard Area: LOMA 17-04-2382A, issued in February 2017, which records a lowest adjacent grade of 14.6 feet NAVD88; LOMA 18-04-1451A, issued in January 2018; and LOMA 22-04-3044A, issued in June 2022, which records 13.8 feet. Both recorded grades sit above the 12.0 to 12.5-foot base flood elevations nearby. A LOMA is address-specific: it covers the building it names and nothing next door. Any Santa Rosa owner can search the address on the FEMA Flood Map Service Center.
FEMA issued a preliminary countywide map for Collier County on March 20, 2025, and on the preliminary National Flood Hazard Layer all 27 Santa Rosa footprints fall in Zone X, along with every other home in the Olde Cypress zoning district. Collier County opened the 90-day appeal period on August 19, 2026 and targets summer 2027 for the new map to take effect, per its August 2026 release on the proposed Flood Insurance Rate Map. Until then the 2012 map governs lending and insurance, and the preliminary map can change on appeal. We never describe a Santa Rosa home as "not in a flood zone."
Buyers: ask early for the elevation certificate and any LOMA, get a flood quote even where none is required, and let the lender's determination for the specific building decide. Sellers: put the certificate and any LOMA in the listing file before the first showing; without a letter, a licensed surveyor can say whether one is worth applying for.
Selling a Santa Rosa home with a LOMA on file? Presented on day one, it protects the price. Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.
Santa Rosa at Olde Cypress sits in Collier County Evacuation Zone E and the state's Category 4 storm surge zone, about 6.7 miles inland, outside the Coastal High Hazard Area. Homes there are designed to a 160 mph ultimate wind speed for new work, and roof age and opening protection drive the insurance price.
Every Olde Cypress 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 storm surge zone on the Florida Division of Emergency Management's Collier County storm surge zone map. There is no Zone VE, no Limit of Moderate Wave Action and no Coastal High Hazard Area in the community. The county's orders for each storm, shown on the state's Collier County evacuation map, are the ones to follow.
Collier County's Florida Building Code wind layers, in its map services directory, return an ultimate design wind speed of 160 mph for Risk Category II buildings such as houses across Olde Cypress. At that speed the community sits inside the wind-borne debris region by our reading of the code, so replacement windows, sliders and exterior doors generally need impact rating or approved shutters; confirm with your contractor and Collier County plan review.
Hurricane Irma, on September 10, 2017, brought a 112 mph gust at the North Naples station, per the National Weather Service Miami Irma report, and 88 of ZIP 34119's 124 all-time NFIP claims date from 2017 in FEMA's OpenFEMA claims dataset. The National Weather Service Ian summary places Ian's 2022 surge flooding south and west of US 41. We found no report naming Monteverde Way for storm damage; that is not proof of none, so ask for repair invoices and permits.
No agency publishes a homeowners or windstorm premium for Olde Cypress, and we will not invent one. The price for a specific Monteverde Way home turns on roof age and covering, roof-to-wall connection, opening protection, roof shape, secondary water resistance, code era, flood status and the deductible. The Uniform Mitigation Verification Inspection Form, OIR-B1-1802, documents the wind features that earn credits. For Santa Rosa's nine first-pulse homes, likely permitted before 2002, a four-point inspection is the other document carriers commonly request.
Selling a Santa Rosa home with a newer roof or impact glass? Those belong in the price, not in the buyer's inspection report. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008; get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.
Every Santa Rosa at Olde Cypress address, on Monteverde Way and Olde Cypress Drive, is zoned for 2026-2027 to Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High, per the Collier County Public Schools address lookup. All three earned an A in each of the 2024, 2025 and 2026 state grade releases.
The source is the district's Collier County Public Schools address lookup for 2026-2027, queried for every Monteverde Way record (26) and Olde Cypress Drive, and cross-checked on the attendance zone map: 453 of 453 single-family address records behind the gate returned the same three schools.
School | Grades | 2026 grade | 2025 | 2024 | Road miles from the gate |
|---|---|---|---|---|---|
PK to 5 | A (85% of points, the top elementary score in Collier) | A | A | 1.2 | |
6 to 8 | A (79%) | A | A | 2.8 | |
9 to 12 | A (75%, second among Collier high schools) | A | A | 6.0 |
Grades from the Naples Daily News Collier County school grade database, which republishes Florida Department of Education data, and the paper's July 22, 2026 report on Collier school grades; the state's own figures are on the FLDOE school grades page. Distances are free-flow road miles from the Treeline Drive entrance.
Some sources say Olde Cypress is zoned to Gulf Coast High. That is true only for the Fairway Preserve condominium outside the gate; every Santa Rosa address returns Aubrey Rogers High. Confirm the specific address with the district before relying on it.
Santa Rosa at Olde Cypress permit history is held address by address in Collier County's permitting system, and we did not pull a permit report for any Monteverde Way home for this guide. What the public record does show is the build era, the FEMA letters and the recorded declaration chain described above.
We did not read roof, window, pool or remodel permits for individual Santa Rosa homes, and we make no claim about which homes have been re-roofed or fitted with impact glass. Those facts belong to the specific address, and they are the first things a buyer's inspector and insurer will ask about. A seller should pull the permit history for the address before listing, so that any open or expired permit is closed before a buyer finds it. Collier County's Building Bulletin 21 on surveys and elevation certificates also sets the floor-elevation standard any substantial rebuild on a Santa Rosa lot would have to meet: the higher of base flood elevation plus one foot, the water management district permit elevation, or 18 inches above the crown of the nearest road.
Nothing is being built inside Santa Rosa at Olde Cypress, which has no vacant homesites. Around Olde Cypress the changes are roads: Collier County rates Immokalee Road in front of the community over capacity, and the fixes include the Vanderbilt Beach Road Extension, a diverging diamond at I-75 Exit 111 and a $20.5 million Immokalee Road project.
About 19 acres of agriculturally zoned land immediately east of Olde Cypress is owned by the North Collier Fire Control and Rescue District on the 2026 preliminary roll, and its intended use is unknown; we found no petition for it. Across Immokalee Road, the Laurel Oak Elementary and Gulf Coast High campus faces the community's south edge. For Monteverde Way, corridor construction means a longer drive out, not traffic on the street.
A Santa Rosa at Olde Cypress trip starts on Monteverde Way, runs out Olde Cypress Drive and Treeline Drive to the single gate at Logan Boulevard North, and reaches I-75 Exit 111 about 1.6 miles past the gate. Groceries, an A-rated elementary school and a 24-hour emergency room are all within about 2.5 miles of the entrance.
Guests and contractors are cleared through the gatehouse on Treeline Drive, per the master association's community access sheet. Buyers touring outside open house hours must come with an agent or owner, which is one practical reason to tour Santa Rosa with an agent who can arrange access.
Destination | Road miles | Modeled minutes, no traffic |
|---|---|---|
I-75 Exit 111 (Immokalee Road) | 1.6 | About 3 |
NCH Emergency Department Northeast, 15420 Collier Blvd | 2.4 | About 5 |
NCH North Naples Hospital | 4.4 | About 8 |
Mercato | 7.3 | About 14 |
Delnor-Wiggins Pass State Park | 7.0 | About 14 |
Vanderbilt Beach | 8.2 | About 15 |
Naples Airport terminal | 11.9 | About 18 |
Downtown Naples, Fifth Avenue South | 14.5 | About 23 |
Southwest Florida International Airport terminal | 21.1 | About 27 |
Routes and times from the OSRM routing engine at free-flow speeds from the Treeline Drive and Logan Boulevard North intersection; add the interior drive from Monteverde Way, and round up in season. Hospital details from the operator pages for NCH Emergency Department Northeast and NCH North Naples Hospital; beach details from Florida State Parks for Delnor-Wiggins Pass.
Want to test the drive from Monteverde Way at rush hour before you write an offer? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida. Selling? Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072.
Santa Rosa at Olde Cypress is the fourth-smallest of the nine Olde Cypress neighborhoods at 27 homes, one of four with every lot on the golf course, and the one whose recent recorded sales sit highest among the mid-size detached neighborhoods: a 36-month county median of $1,512,500 on 3 sales, a small sample.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Yardstick: homes and product from the Collier County Property Appraiser 2026 preliminary roll; association of record; Southwest Florida MLS closings in the 48 months to September 26, 2026 (the widest MLS window); Collier County recorded qualified sales in the 36 months to August 29, 2026; median 2026 preliminary just value; and lots within 10 feet of the golf course parcel. Samples under ten are small; one or two sales are listed, never turned into a median.
Neighborhood | Homes and product | Association | MLS closings, 48 months: n and median | County qualified sales, 36 months: n and median | Median 2026 preliminary just value | Golf-adjacent lots |
|---|---|---|---|---|---|---|
Santa Rosa | 27 detached | Santa Rosa at Olde Cypress Homeowners' Association | 4, listed: $1,229,000 to $1,825,000 (small sample) | 3, $1,512,500 (small sample) | $1,079,324 | 27 of 27 |
Terramar | 55 detached | Terramar at Olde Cypress Homeowners Association | 11, $1,400,000 | 8, $1,137,000 (small sample) | $965,006 | 55 of 55 |
Units One, Two and Three | 185 detached | Olde Cypress Homeowners' Association | 31, $1,450,000 | 20, $1,280,000 | $1,195,234 | 141 of 185 |
Lantana | 122 detached | Lantana at Olde Cypress Homeowner's Association | 28, $1,335,000 | 18, $1,285,000 | $1,045,298 | 13 of 122 (mostly lake) |
Da Vinci Estates | 60 detached estate | Da Vinci Estates Homeowners' Association | 17, $2,150,000 | 12, $2,387,500 | $1,657,416 | 28 of 60 (mixed) |
Santorini Villas | 55 attached paired villas | Santorini Villas Homeowners' Association | 13, $645,000 | 11, $640,000 | $558,186 | 36 of 55 |
Egret Cove | 18 detached | Egret Cove of Naples Homeowner's Association | 2, listed: $1,025,000 and $1,200,000 | 0 | $828,724 | 18 of 18 |
Strada Bella | 18 detached estate | Strada Bella at Olde Cypress Neighborhood Association | 1, listed: $1,775,000 | 1, $1,775,000 | $1,365,158 | 17 of 18 |
Biscayne Place | 8 detached estate | Biscayne Place Homeowners Association | 0 | 0 | $1,704,810 | 8 of 8 |
All Olde Cypress | 548 | Master association plus nine | 107, $1,400,000 | 72, $1,302,500 |
Sources: Southwest Florida MLS Matrix, retrieved September 26, 2026, closings September 27, 2022 to September 26, 2026, assigned by street; Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026; Collier County Property Appraiser, 2026 tax roll (preliminary) and parcel polygons.
On county recordings over three years, Santa Rosa's $1,512,500 median sits below Da Vinci Estates and above Lantana, Units One to Three and Terramar. On the MLS, three of its four sales since 2022 sit between the 48-month Lantana median of $1,335,000 and the Da Vinci Estates median of $2,150,000. With three county sales in 36 months, one sale could move Santa Rosa a rung either way, but it clearly does not trade at the discount its fifth-ranked median just value might suggest.
Four Olde Cypress neighborhoods have every lot on the course: Santa Rosa, Terramar at Olde Cypress, Egret Cove at Olde Cypress and Biscayne Place at Olde Cypress. Egret Cove, 18 homes on one cul-de-sac, is the compact entry, with a median just value about $250,000 below Santa Rosa's; Biscayne Place, 8 estate homes at the gate, is the top end. Santa Rosa sits between them, closest to Terramar.
The 185 homes of Units One, Two and Three at Olde Cypress and the 122 of Lantana offer more choice, with 31 and 28 MLS closings in four years against Santa Rosa's 4; Lantana, built 2013 to 2016, is newer and mostly lake-oriented. Da Vinci Estates at Olde Cypress is the step up in lot size. Strada Bella at Olde Cypress and Santorini Villas at Olde Cypress, the only attached product, complete the set. The whole community is covered in our Olde Cypress community guide, with the community-wide Olde Cypress seller's guide and Olde Cypress buyer's guide.
Selling in Santa Rosa? Pricing a 27-home neighborhood means using the siblings well, and McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008. Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.
Choose Santa Rosa at Olde Cypress for a quieter 27-home street, somewhat larger recent homes and the higher recent recorded prices; choose Terramar at Olde Cypress for twice the homes, more frequent listings, a lower entry price and slightly larger lots, with every lot on the golf course in both.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Measure | Santa Rosa at Olde Cypress | Terramar at Olde Cypress |
|---|---|---|
Homes (2026 preliminary roll) | 27 detached | 55 detached |
Streets | Monteverde Way (26), Olde Cypress Drive (1) | Terramar Drive (43), Terramar Court (12) |
Median lot | 9,907 sq ft | 10,479 sq ft |
Median county footprint (not living area) | 4,383 sq ft | 4,858 sq ft |
Year built on the roll | 2000 to 2007, median 2005 | 2000 to 2006, median 2003 |
Golf-adjacent lots | 27 of 27 | 55 of 55 |
MLS closings, 48 months | 4, listed, $1,229,000 to $1,825,000 | 11, median $1,400,000, $850,000 to $1,900,000 |
MLS living area on those sales | 2,551 to 4,044 sq ft | 2,007 to 3,287 sq ft |
Sold $ per living sq ft, 48 months | $417.18 to $592.90 (4 sales) | Median $446.14 (n = 11) |
Sold to final list, 48 months | 92.48% to 98.46% (4 sales) | Median 93.65% (n = 11) |
MLS closings, 12 months | 2: $1,512,500 and $1,600,000 | 3: $1,075,000, $1,099,000 and $1,750,000 |
For sale on September 26, 2026 | None | 2 active, listed at $1,669,900 and $1,825,000 |
County qualified sales, 60 months | 5, median $1,512,500 | 16, median $1,397,500 |
Median 2026 preliminary just value | $1,079,324 | $965,006 |
Median 2026 preliminary total taxes | $7,692 | $7,334 |
Homestead share | 18 of 27 (66.7%) | 36 of 55 (65.5%) |
Effective 2012 flood map: footprints wholly in Zone AH / partly / Zone X | 12 / 11 / 4 | 7 / 31 / 17, and 4 lots touch Zone AE |
Preliminary 2025 flood map | All 27 in Zone X | All 55 in Zone X |
Current neighborhood declaration | 2011 restatement, OR 4722 PG 375 | 2000 declaration, OR 2689 PG 1846, amended 2003 |
Road tract title | Santa Rosa association | Still titled to Terramar Development, Inc. |
Sources: Southwest Florida MLS Matrix, retrieved September 26, 2026; Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026, and 2026 tax roll (preliminary); FEMA effective and preliminary National Flood Hazard Layers.
The two overlap on price but not on pace: Terramar's 11 sales in four years give roughly three chances a year at a $1,400,000 median, Santa Rosa's 4 about one. In the last 12 months Terramar sold at $1,075,000 to $1,750,000 and Santa Rosa at $1,512,500 and $1,600,000, partly because Santa Rosa's recent homes were larger; per living square foot the ranges overlap heavily.
Terramar has the lighter mapped exposure on the 2012 map, 7 footprints wholly in Zone AH against Santa Rosa's 12, but four Terramar lots touch Zone AE at the lake edge. Both have FEMA letters on file, and both are entirely Zone X on the preliminary 2025 map. Terramar's road tract is still titled to its original declarant, a title item Santa Rosa does not carry.
A buyer who wants the quietest golf street in the middle of Olde Cypress, wants 2,500 square feet or more, and can wait for the right house; and one who values an association that holds its own road tract and a 2011 restated declaration.
A buyer who needs a home this season, since Terramar had two actives on September 26, 2026 and Santa Rosa none, or who wants the lowest all-golf detached entry price, a slightly larger lot or the lighter mapped flood exposure. Our Terramar at Olde Cypress guide covers it street by street.
Deciding between Monteverde Way and Terramar Drive? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida. Selling in either? Get a free Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072.
Owning at Santa Rosa at Olde Cypress trades scarcity for quiet: every lot on the golf course, a dead-end interior street and strong recent recorded prices, against a thin sales record, no current listings, unpublished association fees and a flood map that splits the street.
If you're searching for a Santa Rosa at Olde Cypress listing agent, or thinking, 'I need someone to sell my Santa Rosa at Olde Cypress home...' you are selling one of 27 golf-course homes on a street that lists about once a year, where the price has to be built, not looked up. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008.
In the last 12 months we tracked all 26 Olde Cypress closings in the Southwest Florida MLS, retrieved September 26, 2026, including both of Santa Rosa's. With our Domain Realty Group team we have sold over $2.5 billion in real estate, and Jesse McGreevy and Marc Comisar account for over $900 million in personal sales inside that number.
Honors and recognition:
The Matrix pull did not record listing offices, so we state no represented-sale count; ask and we will walk you through all four MLS closings.
Start with a free Santa Rosa at Olde Cypress home valuation. Jesse follows up with the four Monteverde Way closings, adjusted for size, lot, roof and flood status, and the nearest Terramar, Units One to Three and Lantana sales. For the full seller playbook, read how we sell homes in Santa Rosa at Olde Cypress.
(239) 898-6072, text or call. Confidential conversations welcome.
For a home priced to its size and condition, the timing is favorable: there was no competing Santa Rosa listing on September 26, 2026, and Olde Cypress as a whole held about 2.3 months of supply. Listing in the fall reaches the winter buyers who drive the Naples season.
From the four MLS sales first, adjusted for size and date, then from the county's 60-month record and the closest sibling sales. The December 2025 pair set the current reference at $1,512,500 to $1,600,000 for 2,551 to 2,898 square feet.
No. The smallest recent home brought $592.90 per living square foot and the largest, in 2023, $451.29. Added space on Monteverde Way sells at a lower rate than the first 2,500 square feet.
The master documents we read require board approval for leases; we found no master approval step for a sale. The 2011 Santa Rosa restatement should still be checked for any notice or approval clause, and the estoppel is required either way.
The survey and elevation certificate, any LOMA, the roof permit and wind mitigation form, the Section 720.401 disclosure summary, the Santa Rosa association contact for the estoppel, and the club's current membership terms.
Santa Rosa at Olde Cypress owners and buyers work directly with Jesse McGreevy and Marc Comisar, who have sold Southwest Florida real estate for more than twenty years, lead Domain Realty Group, and read every Santa Rosa sale, flood letter and recorded document behind this guide before publishing it.
You can read how the team was built on our about the McGreevy and Comisar team page. McGreevy and Comisar are the Domain Realty team behind this Santa Rosa at Olde Cypress guide: Jesse McGreevy, Sales Associate, and Marc Comisar, Broker Associate. Both work the North Naples golf-community market that Olde Cypress sits in.
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com.
McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008.
McGreevy and Comisar is a top-reviewed Santa Rosa at Olde Cypress realtor on Google, and the quotes below are genuine 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 can only say he is a refreshing and highly motivated professional. No tricks exaggerations nor falsehoods. His way of bringing quality clients is exceptional. He does not bring lookers. He brings buyers!” Dennis Overton, verified Google review
★★★★★ “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.” Beth Shaw, verified Google review
★★★★★ “No one knows real estate, especially Florida real estate like Marc and Jesse. Smart and savvy. They also have a great team that is knowledgeable and professional.” Christian Schnabel, verified Google review
★★★★★ “Their attention to detail communication and dedication was known the moment we spoke. Would highly recommend.” Kaitlyn Heffner, verified Google review
Selling a Santa Rosa at Olde Cypress home? Get a free Santa Rosa at Olde Cypress home valuation, or Call Jesse direct at (239) 898-6072.
Buying in Santa Rosa at Olde Cypress? Call Marc at (239) 287-5873, or read our Santa Rosa at Olde Cypress buyer's guide.
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.
These Santa Rosa at Olde Cypress buyer questions are answered from the recorded declarations, the master association and club pages, Collier County, State of Florida and FEMA records, and the Southwest Florida MLS Matrix retrieved September 26, 2026. Where the public record stops, the answer says so and names the document that closes the gap.
A neighborhood of 27 detached single-family homes inside the gated Olde Cypress community in North Naples, Florida 34119, run by Santa Rosa at Olde Cypress Homeowners' Association, Inc. under the Olde Cypress master association.
On Monteverde Way, a street off Olde Cypress Drive in the middle of the community, with one more Santa Rosa home addressed on Olde Cypress Drive itself. All traffic enters through the single gate on Treeline Drive at Logan Boulevard North.
Not on September 26, 2026: the Southwest Florida MLS showed no active or pending Santa Rosa listing. The neighborhood averaged about one MLS closing a year over the last four years.
The four MLS sales since September 2022 were $1,825,000, $1,229,000, $1,512,500 and $1,600,000. The most recent two, in December 2025, were $1,512,500 and $1,600,000.
A four-bedroom-plus-den home of 2,898 square feet on Monteverde Way that closed December 4, 2025 at $1,600,000, 98.46% of its final list price, after 34 days on market.
The four MLS sales since 2022 measured 2,551 to 4,044 square feet of living area, with three or four bedrooms plus a den. County building footprints, which include garages and lanais, have a median of 4,383 square feet.
From 8,602 to 16,006 square feet on the county's parcel polygons, a median of 9,907, in the middle of the Olde Cypress range.
Between about 2000 and 2007, in two pulses: eleven by 2004 and sixteen more by 2007. The 2026 roll gives a median year built of 2005.
Yes. All 27 lots sit within 10 feet of the golf course parcel on the county map, one of four Olde Cypress neighborhoods where every lot does.
The recorded pages available to us do not name a builder or a separate declarant for Santa Rosa, and we do not guess. A home's permit history names the contractor for that address.
Santa Rosa owners pay one quarterly invoice that includes the neighborhood's costs and the master association share. The amount is not published outside the resident portal; the estoppel certificate for the specific home states it.
Yes. Section 14.02 of the 2019 master declaration makes every owner a social member of The Club at Olde Cypress on acquiring the home. Golf membership is optional and sold separately.
The club does not publish them. Ask the membership office at (239) 596-4797 for current social dues and any golf initiation and dues, in writing, before your inspection period ends.
The club states it has no member assessments and no food and beverage minimum, and the $16 million clubhouse renovation was funded by the owner without a member assessment.
No. Olde Cypress has no community development district, and the 2026 preliminary roll shows no non-ad valorem assessment on any Olde Cypress single-family parcel.
The median 2026 preliminary total tax is $7,692 across the 27 homes, at a 2025 rate of 9.5058 mills. A buyer's bill resets toward the just value the year after purchase.
On the effective 2012 FEMA map, 12 footprints sit wholly in Zone AH, 11 partly and 4 in Zone X. The preliminary 2025 map shows all 27 in Zone X but is not effective yet.
Three Monteverde Way homes hold Letters of Map Amendment issued in 2017, 2018 and 2022. Each covers only the building it names.
The lender decides per building from its flood determination. Where the home is in Zone AH on the effective map with no LOMA and you have a federally backed or regulated mortgage, expect a requirement.
Zone E, one of Collier County's outer tiers, and the state's Category 4 storm surge zone. There is no Coastal High Hazard Area or Zone VE in Olde Cypress.
Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026-2027, per the district's address lookup. All three earned an A in 2024, 2025 and 2026.
No. We found no housing-for-older-persons designation in the Olde Cypress records.
Yes, within the master rules: a 60-day minimum, no more than four leases per calendar year, board approval, a $100 application fee and a $1,000 refundable deposit. Check the 2011 Santa Rosa restatement for any stricter rule.
Common household pets are allowed under master Section 9.18, leashed outdoors and never left unattended or tethered outside. Livestock, poultry and reptiles are prohibited.
No. The master declaration bars overnight parking of any vehicle on Olde Cypress streets and limits driveways to two cars.
About 1.6 road miles from the gate to I-75 Exit 111, about 7.0 miles to Delnor-Wiggins Pass State Park and 8.2 to Vanderbilt Beach, plus the interior drive from Monteverde Way.
No. Fairway Preserve at Olde Cypress is a separate 264-unit condominium with its own entrance off Immokalee Road; it is outside the gate and the master association, and its owners get no club social membership.
Terramar has twice the homes, slightly larger lots, a lower entry price and more frequent sales; Santa Rosa has a quieter street, larger recent homes and higher recent recorded prices. Every lot is on the golf course in both.
Nine homes first appear in the 2000 or 2002 county footprint layers and were likely permitted before Florida's statewide building code took effect in 2002. Confirm the permit date for any specific home.
The 2011 Santa Rosa restatement at OR 4722 PG 375, then the 2019 master declaration, then the estoppel certificate and the club's membership terms for the specific home.
These Santa Rosa at Olde Cypress seller questions cover pricing, paperwork, the club and closing costs on Monteverde Way, answered from the MLS and county sales records, the recorded declarations and Florida statutes. Where a number depends on your specific home, the answer says what we need to see.
The one who can price a 27-home neighborhood with four MLS sales in four years. We tracked every Santa Rosa MLS closing since 2022 and every county sale since 2001; call Jesse at (239) 898-6072.
It starts with the December 2025 pair, $1,512,500 and $1,600,000 for 2,551 and 2,898 square feet, adjusted for your size, lot, roof, flood status and condition. A free valuation gives you the specific number.
The four MLS sales since 2022 took 7, 21, 34 and 34 days on market. Across Olde Cypress the 12-month median was 29 days.
The four MLS sales closed at 98.46%, 96.03%, 93.59% and 92.48% of their final list prices; the two 2025 sales were within 4 percent.
Yes, on a thin record. The 2018 to 2020 county recordings were $675,000 to $750,000; every qualified recording since November 2021 has been above $1.2 million, and the 2025 pair were $1,512,500 and $1,600,000.
Not on September 26, 2026, when no Santa Rosa home was active or pending. Your competition is Terramar, Units One to Three and Lantana listings.
Carefully, because the only large-home sale is the 4,044 square foot home that sold for $1,825,000 in February 2023. Added space sells at a lower rate per foot than the first 2,500 square feet here.
Every Santa Rosa lot is on the course, so the golf view is priced into the neighborhood rather than into one home. Orientation and the view from the lanai still separate homes.
Most Olde Cypress sales record in season: 11 of the 24 county recordings in the 12 months to August 2026 came in January to March. Listing in the fall reaches those buyers.
The Section 720.401 homeowners association disclosure summary. Without it, the buyer can cancel before closing. The Section 689.261 property tax disclosure summary is also required.
The association's statement of what is owed on your home, capped at $299 on a current account under Section 720.30851. In Collier County the seller customarily pays it.
The master association may collect a working capital contribution at transfer under Section 8.13 of the master declaration. The Board sets the amount and it is not published; the estoppel states it.
Social membership passes to the buyer by covenant at closing. The club describes its golf memberships as non-transferable, so a buyer who wants golf deals with the club directly.
Not by custom in Collier County, where the buyer customarily pays the owner's title policy and chooses the closing agent. The contract controls, so read that paragraph before you sign.
The deed documentary stamp tax at $0.70 per $100, $11,200 on a $1,600,000 sale, the estoppel fee, any payoff and prorated taxes, plus the commission you negotiate. Commissions are negotiable and not set by law.
No. Since the August 17, 2024 NAR practice changes, any offer of buyer-broker compensation is a seller's choice made off the MLS, and buyers sign written agreements with their own agents.
The elevation certificate and any LOMA or LOMR-F for your address. Three Monteverde Way homes already hold LOMAs; if yours touches Zone AH on the 2012 map without one, ask a surveyor whether to apply.
It shows all 27 Santa Rosa homes in Zone X, but it is not effective until FEMA finalizes it, targeted for summer 2027. Today's buyer's lender still uses the 2012 map.
Almost certainly. Have the re-roof permit, the wind mitigation form and, for a first-pulse home built around 2000 to 2002, a four-point inspection ready.
Any exterior change needs both the Santa Rosa and master architectural approvals. Interior work generally does not, but check permits for anything structural, electrical or plumbing.
Yes, on Saturday or Sunday from noon to 5 p.m. under the master association's rules, with the sign from the guard house against a $20 deposit.
One standardized green wooden sign, 2 feet by 1.5 feet, in the colors the master association specifies on its Realtors Information page.
Yes. We can market quietly to qualified buyers, which suits a 27-home street where a public listing is noticed by every neighbor.
Yes, subject to the lease, which the buyer takes over. Master rules require leases of at least 60 days and board approval, so share the lease and its approval with buyers early.
Probably. The buyer loses your Save Our Homes cap, and the assessed value resets to the just value the year after the sale.
Florida portability can carry part of your Save Our Homes difference to a new Florida homestead if you apply in time. Confirm the deadline with the Property Appraiser.
No. Olde Cypress has no community development district and no bond line on its tax bills.
It depends on your timing and tax position. Renting is limited to four leases a year with a 60-day minimum, and the next Santa Rosa buyer will have no competing listing on the street today.
With drone video of the fairway view, a full document file sent ahead, and outreach beyond Naples: 7 of the 27 homes are owned by people who receive their tax bill in another state.
Terramar is the nearest comparable with more sales: 11 in four years at a $1,400,000 median. Its buyers will compare, so price with Terramar's two current listings in view.
Section 8.13 lets the master association collect it at transfer of title; the purchase contract should say who pays it. Ask for the amount on the estoppel before you negotiate.
Because a thin market rewards pricing judgment and preparation. We are Top 1% Real Estate Agents Nationally Since 2008, and we build the flood, estoppel and club file before the first showing.
Every fact in this Santa Rosa at Olde Cypress guide traces to a primary record below. Parcel and sale facts come from the county roll. No brokerage, listing portal or IDX feed is cited.
Santa Rosa at Olde Cypress's key documents are published by the master association, Collier County and the State of Florida; the table links each to its issuing authority, and we do not re-host them. The Santa Rosa neighborhood budget and the club's dues schedule are not posted publicly; the estoppel certificate and the club's membership office supply them at contract.
Document | Issued by | Date | Link |
|---|---|---|---|
Santa Rosa Amended Declaration, Articles and Bylaws | Santa Rosa at Olde Cypress Homeowners' Association (hosted by the master association) | 2011, OR 4722 PG 375 | |
Amended and Restated Declaration for Olde Cypress | Olde Cypress Master Property Owners Association | Recorded November 27, 2019 | |
Leasing Certificate of Amendment | Olde Cypress Master Property Owners Association | 2013, OR 4874 PG 3783 | |
Community access sheet | Olde Cypress Master Property Owners Association | November 2024 | |
Floodplain Protection newsletter | Collier County | 2026 | |
Uniform Mitigation Verification Inspection Form | Florida Office of Insurance Regulation | rev. January 2012 |
Market data from Southwest Florida MLS, pulled September 2026. McGreevy and Comisar, Best Realtor for Santa Rosa at Olde Cypress. Brokered by Domain Realty. Jesse McGreevy, FL Lic. SL3101296 · Marc Comisar, FL Lic. BK3060671.
Thinking about buying or selling in Southwest Florida? Tell us what you are trying to do and we will tell you honestly what it will take. McGreevy and Comisar, Domain Realty Group.
