Updated September 2026
Sell your Santa Rosa at Olde Cypress home with McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008. Priced from every Monteverde Way sale, four MLS closings and 44 county deeds, with the club and flood file ready. Call (239) 898-6072.
Updated September 2026 · By Jesse McGreevy and Marc Comisar, Domain Realty
Santa Rosa at Olde Cypress is 27 detached homes on the golf course of a gated North Naples club community, and only four of them closed through the Southwest Florida MLS in four years. McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008, price a sale that rare from every recorded Santa Rosa sale, one by one.
This page is written for the Santa Rosa owner who is thinking about selling. The neighborhood itself, its association, its lots and its flood file, is described in our Santa Rosa at Olde Cypress neighborhood guide, and the gated community around it in our Olde Cypress community guide. This is the Santa Rosa inside Olde Cypress, off Logan Boulevard North in Naples, not Santa Rosa County or Santa Rosa Beach in the Florida Panhandle, and not Fairway Preserve at Olde Cypress, the 264-unit condominium off Immokalee Road that sits outside the gate. Call Jesse McGreevy direct at (239) 898-6072 whenever you want to talk it through.
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, 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.
These are career figures across Lee and Collier County. 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.
In the last 48 months Santa Rosa at Olde Cypress has seen four MLS resales. What we can show you is every sale on the record. We tracked every one of the 4 Santa Rosa closings in the Southwest Florida MLS since September 2022, and all 44 qualified Santa Rosa sales in Collier County's deed record since 2001, before we wrote a single figure here. Where this page walks through a sale in detail, it is a public-record sale, labelled as one.
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 and walkthroughs for owners who are out of state. Start with a Santa Rosa at Olde Cypress home valuation or call Jesse at (239) 898-6072. If you are buying as well, read how we represent buyers in Naples or call Marc at (239) 287-5873, and see how the partnership works on our about McGreevy and Comisar page.
Selling in Santa Rosa at Olde Cypress differs from a typical Naples sale in six ways: 27 homes on essentially one street, every lot on the golf course, a sale only every year or two, its own association and declaration, a club social membership that passes with the deed, and today no competing Santa Rosa listing at all.
The Collier County Property Appraiser 2026 preliminary roll counts 27 single-family homes in Santa Rosa: 26 on Monteverde Way and one on Olde Cypress Drive. That is about 5 percent of the 548 homes behind the Olde Cypress gate, which the master association rounds to 550. Monteverde Way branches off Olde Cypress Drive, the road that feeds every neighborhood street, and sits in the middle of the community, well inside the single Treeline Drive gate.
All 27 Santa Rosa lots sit within 10 feet of the golf course parcel on the county map, a 100 percent golf-adjacent count that only Terramar, Egret Cove and Biscayne Place also reach. Lots run 8,602 to 16,006 square feet, median 9,907. For a seller, that means the buyer is choosing between fairway views and exposures on the same street, not between golf and no golf.
County building footprints show Santa Rosa built in two waves: nine homes in the 2000 or 2002 aerial layers, two by 2004, then sixteen in the 2006 to 2009 layers, fourteen of them by 2006. The 2026 preliminary roll dates the homes 2000 to 2007, with a median year of 2005. Your home's wave decides which building code it was permitted under and what a buyer's insurer will ask to see.
Santa Rosa at Olde Cypress Homeowners' Association, Inc. was filed with the state on April 9, 2001, owns the neighborhood's road tract on the 2026 preliminary roll, and governs under a declaration first recorded at OR 3057 PG 2810, restated in 2006 and again in 2011 (OR 4722 PG 375). Unlike most Olde Cypress neighborhoods, its state filing lists an outside registered agent in St. Petersburg rather than the master association's manager.
"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 at OR 5700 PG 1118. Your buyer inherits the social membership; golf is a separate, optional purchase from the privately owned, non-equity club, so there is no equity certificate to sell back.
On September 26, 2026 the Southwest Florida MLS showed no Santa Rosa home active and none pending. The nearest competition a buyer will tour is two Terramar listings a short walk away on Terramar Drive, at $1,825,000 and $1,669,900. The next Santa Rosa owner to list has the street to themselves, and the first price published sets the comparable for everyone after.
Santa Rosa at Olde Cypress trades rarely and high: four MLS closings in 48 months, each listed below, and 44 qualified county sales since 2001. The takeaways below condense the evidence a Santa Rosa seller in Naples needs before choosing a price, a date and an agent.
For a Santa Rosa home priced to its own recorded sales, yes. Santa Rosa at Olde Cypress has no active or pending listing, the two December 2025 closings reached 96.03 and 98.46 percent of list within 34 days, and the wider Olde Cypress market sits at about 2.3 months of supply. Four sales in four years still make every price a judgment.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
| Closed | Street | Beds and baths | Living sq ft | Final list | Sold | Per living sq ft | Sold-to-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 names OLDE CYPRESS and SANTA ROSA AT OLDE CYPRESS, closed September 27, 2022 to September 26, 2026, retrieved September 26, 2026, with each sale assigned to Santa Rosa by street against the county roll. Sold-to-list is measured against the final list price. Total volume over the four sales was $6,166,500.
Four closings are not a market, so we show them rather than summarize them. If you want the arithmetic anyway: the 48-month median is $1,556,250, the mean of the middle pair ($1,512,500 and $1,600,000), a small sample; the median sold-to-list is 94.81 percent (the mean of 93.59 and 96.03), and the median days on market 27.5 (the mean of 21 and 34).
The Southwest Florida MLS carries Santa Rosa listings under two development names, OLDE CYPRESS and SANTA ROSA AT OLDE CYPRESS, so a search on either name alone can miss a Santa Rosa sale. We pulled both and assigned every row to its neighborhood by street address against the Collier County roll. A buyer's agent who searched one name may be working from half the evidence.
| Twelve months to September 26, 2026 | Santa Rosa at Olde Cypress | All of Olde Cypress |
|---|---|---|
| MLS closings | 2 (small sample) | 26 |
| Sold prices | $1,512,500 and $1,600,000 | Median $1,105,000 (mean of $1,100,000 and $1,110,000) |
| Per living sq ft | $592.90 and $552.10 | Median $472.75 |
| Sold-to-list | 96.03% and 98.46% | Median 97.52% |
| Days on market | 7 and 34 | Median 29 (n=24) |
| Active and pending on September 26, 2026 | 0 and 0 | 5 active, 1 pending |
Both Santa Rosa closings of the year sold above the community's median price per square foot, one well inside the community's 29-day median marketing time and one a few days past it. Santa Rosa accounted for 2 of the 26 Olde Cypress closings, which is about its share of the homes.
None of the four Santa Rosa closings in 48 months reached its final list price; the concessions ran $25,000, $62,500, $100,000 and $125,000. Across Olde Cypress, 6 of 26 closings in the last twelve months did reach list. Santa Rosa buyers have negotiated every time, and the smallest gap came on the home that stayed on market longest in 2025, which says the gap is about the starting price, not the wait.
Collier County's deed record shows 44 qualified Santa Rosa at Olde Cypress sales since 2001, at an all-history median of $742,500, and 10 in the last ten years, running from $675,000 in December 2020 to $1,825,000 in February 2023. The two 2025 sales, at $1,512,500 and $1,600,000, are the long view's latest word.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
| Window ending August 29, 2026 | Qualified Santa Rosa sales | Median recorded price | Range |
|---|---|---|---|
| 12 months | 2 (small sample) | $1,556,250 (mean of $1,512,500 and $1,600,000) | $1,512,500 to $1,600,000 |
| 36 months | 3 (small sample) | $1,512,500 | $1,229,000 to $1,600,000 |
| 60 months | 5 (small sample) | $1,512,500 | $1,210,000 to $1,825,000 |
| 120 months | 10 | $1,030,000 (mean of $850,000 and $1,210,000) | $675,000 to $1,825,000 |
| All history since 2001 | 44 | $742,500 (mean of $735,000 and $750,000) |
A qualified sale is a transfer the county itself graded as an arm's-length market sale; the file counts improved sales over $100,000. The ten-year median sits far below the five-year one because five of those ten sales recorded at $850,000 or less, before the late-2021 price step.
| 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 |
Years missing from the table recorded no qualified Santa Rosa sale, including 2022 and, so far, 2026 through the file's newest recording on May 22, 2026. From 2010 to 2020 the recorded Santa Rosa price barely moved, between about $650,000 and $800,000. Since 2021 every recorded sale but two has cleared $1,200,000. With one to three sales a year, each year's figure describes one or two houses, not a trend line.
| Recorded | 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 |
Every one of the ten is on Monteverde Way. The single Santa Rosa home on Olde Cypress Drive has not recorded a qualified sale in the decade.
Santa Rosa at Olde Cypress has recorded 44 qualified sales since 2001 but only two in the last twelve months, at $1,512,500 and $1,600,000, and has no home for sale today, so the next list price on Monteverde Way becomes the comparable. Request a written opinion of value through our Santa Rosa at Olde Cypress home valuation 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 Santa Rosa at Olde Cypress, read how we represent buyers in Naples or call Marc Comisar at (239) 287-5873.
The county holds five Santa Rosa sales in five years; the MLS holds four in four. The county grades every deed and dates it by the deed, while the MLS dates a closing when an agent enters it, so the two December 2025 closings appear in the deed file with late-November dates. We use the county for what sold and at what recorded price over the long run, and the MLS for list price, living area and days on market, and we never blend the two into one figure.
The Santa Rosa sales that matter most to your price are the two December 2025 closings on Monteverde Way, at $1,512,500 and $1,600,000, followed by the April 2024 sale at $1,229,000 and the February 2023 sale at $1,825,000. Size, bedroom count and condition separate them more clearly than date does.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
This is a public-record sale from the Southwest Florida MLS, not a McGreevy and Comisar transaction. A Monteverde Way home of 2,551 square feet of living area, three bedrooms plus a den and three and a half baths, closed on December 2, 2025. It was listed at a final $1,575,000, went under contract after 7 days and closed at $1,512,500: 96.03 percent of list and about $593 per square foot, the highest price per square foot of any Santa Rosa sale in the four-year pull.
Three lessons follow for the next Santa Rosa seller. First, the smallest home of the four earned the most per square foot, so a compact Santa Rosa home should not be priced by dividing a larger neighbor's price by its size. Second, a 7-day sale that still gave up $62,500 suggests the buyer arrived ready and negotiated from a figure of their own; a list price anchored to the recorded evidence narrows that gap. Third, the sale landed in December, before the January to May season, so a Santa Rosa home does not have to wait for spring to meet a serious buyer.
Two days later, on December 4, 2025, a larger Monteverde Way home of 2,898 square feet, four bedrooms plus a den, closed at $1,600,000 after 34 days, 98.46 percent of its $1,625,000 final list and about $552 per square foot. Together the pair show the Santa Rosa price curve: the extra 347 square feet added $87,500 to the price but lowered the rate per square foot by about $41.
In April 2024 a 2,946 square foot Monteverde Way home with three bedrooms plus a den closed at $1,229,000 after 21 days, 92.48 percent of list and about $417 per square foot. In February 2023 the largest home in the pull, 4,044 square feet with four bedrooms plus a den and five and a half baths, closed at $1,825,000 after 34 days, 93.59 percent of list and about $451 per square foot. The 2024 home was nearly the size of the December $1,600,000 home and sold for $371,000 less, which is what condition, updates and timing can be worth on this street.
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 Santa Rosa that is two sales at most, so the appraiser will also reach into Terramar, Egret Cove and the Olde Cypress Drive homes of Unit One and adjust. We assemble that comparable set before you list, including the Terramar sales an appraiser will be forced to use, so the price we recommend is one a financed buyer's appraisal can support.
Santa Rosa and Terramar at Olde Cypress are the two all-golf detached neighborhoods a buyer tours together: 27 homes against 55, similar lots, and every home on the course. Santa Rosa has recorded higher prices per square foot on far fewer sales, while Terramar has two homes for sale today and Santa Rosa none.
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 on the 2026 preliminary roll | 27 | 55 |
| Streets | Monteverde Way (26), Olde Cypress Dr (1) | Terramar Dr (43), Terramar Ct (12) |
| Homes backing onto the golf course | 27 of 27 | 55 of 55 |
| Median lot | 9,907 sq ft | 10,479 sq ft |
| Year built on the roll | 2000 to 2007, median 2005 | 2000 to 2006, median 2003 |
| Median 2026 preliminary just value | $1,079,324 | $965,006 |
| Median 2026 preliminary total tax | $7,692 | $7,334 |
| Homestead share | 18 of 27 (66.7%) | 36 of 55 (65.5%) |
| MLS closings, 48 months | 4, listed above (small sample) | 11 |
| Median MLS sold price, 48 months | $1,556,250 (small sample) | $1,400,000 |
| Median per living sq ft, 48 months | $501.70 (small sample) | $446.14 |
| Median sold-to-list, 48 months | 94.81% (small sample) | 93.65% |
| Median days on market, 48 months | 27.5 (small sample) | 20 |
| Active listings, September 26, 2026 | 0 | 2, at $1,825,000 and $1,669,900 |
| County qualified sales, 36 months | 3, median $1,512,500 | 8, median $1,137,000 |
| County qualified sales, all history | 44 since 2001, median $742,500 | 118 since 2000, median $699,650 |
| Effective 2012 flood map, footprints wholly in Zone AH | 12 of 27 | 7 of 55 |
| FEMA structure-removal letters on file | 3, issued 2017 to 2022 | 1 letter from 2012 covering 3 lots |
| March 2025 preliminary flood map | All 27 in Zone X | All 55 in Zone X |
| Schools, 2026 to 2027 | Laurel Oak, Oakridge, Aubrey Rogers | Laurel Oak, Oakridge, Aubrey Rogers |
Sources: Southwest Florida MLS Matrix retrieved September 26, 2026; Collier County Property Appraiser 2026 preliminary roll and recorded qualified sales, data file dated August 29, 2026; FEMA National Flood Hazard Layer. Median figures under ten sales are small samples.
Santa Rosa's 48-month rate per living square foot runs about $56 above Terramar's, and its county just value median about $114,000 higher, on lots about 570 square feet smaller. Part of that is age: more than half of Santa Rosa was built in the 2004 to 2007 wave, while Terramar's median year is 2003. Terramar's roll also shows its road tract still titled to its original developer, a due-diligence item Santa Rosa does not carry.
A buyer who wants the quieter, smaller street, a later build year and no competing listing next door belongs in Santa Rosa. A buyer who wants more choice, a slightly larger lot or a lower entry price will look hard at Terramar, which sold as low as $850,000 in 2025. Your listing should answer that comparison before the buyer's agent raises it.
Terramar's two active listings, at $1,825,000 for 2,816 square feet after 133 days and $1,669,900 for 3,255 square feet after 17 days, are the homes your buyer tours the same afternoon. Price above them and Santa Rosa must show why; price between them and it wins the comparison. Terramar's owners face the same question on the Terramar at Olde Cypress seller page, and the neighborhood itself is described in our Terramar at Olde Cypress guide. Request a Santa Rosa at Olde Cypress home valuation or call Jesse at (239) 898-6072; buyers comparing the two can start with how we represent buyers in Naples or call Marc at (239) 287-5873.
Santa Rosa at Olde Cypress sits in the upper middle of the community's nine-neighborhood price ladder: its 36-month recorded median of $1,512,500 trails only Da Vinci Estates, Unit One and the single Strada Bella sale, while its median just value ranks sixth of eleven county groupings. Few sales, high prices, one street.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
| Neighborhood | Homes | Median 2026 preliminary just value | 36-month recorded median (sales) | 48-month MLS median (closings) |
|---|---|---|---|---|
| Biscayne Place | 8 | $1,704,810 | No sale in 36 months | Counted with Treeline Drive |
| Da Vinci Estates | 60 | $1,657,416 | $2,387,500 (12) | $2,150,000 (17) |
| Olde Cypress Unit Two | 69 | $1,453,941 | $1,305,000 (6) | Wild Orchid Court $1,929,111 (6) |
| Strada Bella | 18 | $1,365,158 | One sale, $1,775,000 | One sale, $1,775,000 |
| Olde Cypress Unit One | 61 | $1,294,566 | $1,847,500 (6) | Treeline and Olde Cypress Drive $1,695,000 (16) |
| Santa Rosa | 27 | $1,079,324 | $1,512,500 (3) | $1,556,250 (4) |
| Lantana | 122 | $1,045,298 | $1,320,000 (17) | $1,335,000 (28) |
| Terramar | 55 | $965,006 | $1,137,000 (8) | $1,400,000 (11) |
| Egret Cove | 18 | $828,724 | No sale in 36 months | Two sales, $1,025,000 and $1,200,000 |
| Lone Pine (Unit Three) | 55 | $783,010 | $972,500 (8) | $1,000,000 (9) |
| Santorini Villas | 55 | $558,186 | $640,000 (11) | $645,000 (13) |
Just value is the county's mass-appraisal estimate for taxation, not a sale price. Medians on fewer than ten sales are small samples. The MLS groups Units One and Two and Biscayne Place by street, so those rows are not directly comparable. Neighbors with their own guides include Egret Cove at Olde Cypress and Lantana at Olde Cypress.
Santa Rosa's recorded sales run well above its just value, by about 40 percent at the 36-month median, the third-widest gap in the community, behind Da Vinci Estates and Unit One. That tells a seller the county's number is not a ceiling. Santa Rosa trades above Lantana and Terramar on similar lots, and the valuation has to show that with sales.
We price a Santa Rosa at Olde Cypress home from the four Monteverde Way MLS closings and the ten county-recorded sales of the last decade, adjusted for living area, bedroom and den count, fairway exposure, build wave, roof, openings and condition, then test the number against Terramar's live listings and what an appraiser will find.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
The four closings bracket almost every Santa Rosa home: 2,551 to 4,044 square feet of living area, three or four bedrooms plus a den, $1,229,000 to $1,825,000. We place your home among them by size and plan, then adjust for what the four did and did not have. Where your home falls outside that bracket, the older county sales and the Terramar and Unit One sales carry the adjustment.
The county divides a sale price by its own base area, which includes garage and covered areas; the MLS divides by the living area a listing agent enters. Santa Rosa's MLS rates ran from about $417 to about $593 per square foot of living area. Your valuation states which system every number came from and never restates one against the other's denominator.
An automated model needs many similar recent sales. Santa Rosa produced two in the last twelve months and four in four years. A model will borrow Terramar, Lantana or Santorini sales to fill the gap, cannot see which fairway your lanai faces, and cannot read a FEMA letter. Your buyer sees that same estimate, which is why your listing needs the evidence behind your price.
Exposure first: every Santa Rosa lot backs onto the golf course, but the hole, the distance to the tee or green, and the afternoon sun on the lanai differ lot by lot. Lot size second, from 8,602 to 16,006 square feet. Then the build wave, because a 2006 home and a 2000 home meet different insurers. Each is a measurable adjustment from recorded sales, not an adjective.
We market a Santa Rosa at Olde Cypress home to the buyer who is choosing a fairway lot inside a gate: professional media that shows the course behind the lanai, the club, fee and flood file ready on day one, and a showing plan built around the staffed Treeline Drive gate and the master association's realtor rules.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
On the 2026 preliminary roll, 18 of 27 Santa Rosa homes carry a Florida homestead exemption and seven owners have mailing addresses in other states. That describes ownership, not people: roughly two in three Santa Rosa homes are primary residences and one in three is held from elsewhere.
The master association's Realtors Information page allows public open houses only on Saturday and Sunday from noon to 5 p.m., with broker opens Monday to Friday; 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. Our showing plan is a guest-access plan first. Professional photography, aerial capture of the fairway, floor plans and video are standard on every McGreevy and Comisar listing.
Jesse McGreevy and Marc Comisar negotiate every Santa Rosa at Olde Cypress offer themselves. Every Santa Rosa buyer of the last four years negotiated, with sold-to-list running from 92.48 to 98.46 percent, so we prepare the club, fee, flood and insurance answers before the first offer arrives.
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.
The four Santa Rosa buyers took $25,000 to $125,000 off the final list price, and the two deepest concessions came on the two largest homes. A home priced on the recorded evidence leaves the buyer less room to argue, and we defend that price with the same four sales, the county record and Terramar's live listings.
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 an unanswered club question never becomes a price concession.
Santa Rosa homes date from 2000 to 2007, and a buyer's insurer will ask for a four-point inspection and a wind mitigation report that can lower the premium. We recommend both 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.
Your sale needs an estoppel certificate from the Santa Rosa association that includes the master share, and the title company will confirm the master association's figures. Santa Rosa is not managed through the master association's manager, so we confirm who issues the certificate before listing and order it the first business day after the contract is signed.
Selling a Santa Rosa at 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 working capital contribution is collected at transfer.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
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 four recent Santa Rosa prices that is $8,603 on $1,229,000, $10,587.50 on $1,512,500, $11,200 on $1,600,000 and $12,775 on $1,825,000.
In 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. No statute fixes this, so the contract controls. Florida promulgates the premium under Florida Administrative Code Rule 69O-186.003, so the rate is the same at every title company.
Under Florida Statutes 720.30851, an association must issue an estoppel certificate stating the regular assessment, the amount paid through and any capital contribution or transfer fee due at closing. The statutory cap is $299 per certificate for a current account, $119 more for delivery within three business days and $179 more if delinquent. In Collier County practice the seller customarily pays it.
Section 8.13 of the restated master 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. We could not locate the current amount in any public document, and no Santa Rosa transfer fee was located either; your estoppel certificate will state what applies, and who pays it is a contract term we settle before signing.
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, 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 is a separate decision we make together.
| Line, illustrative sale at $1,556,250 closing June 30 | Who pays | Amount |
|---|---|---|
| Documentary stamp tax on the deed | Seller, by custom | $10,894.10 |
| Santa Rosa association estoppel certificate | Seller, by custom | Up to $299, plus $119 if rushed |
| Municipal lien search | Seller, by custom | Set by the title company |
| Property tax proration on the $7,692 Santa Rosa median bill | Seller credits buyer | About $3,814 |
| Owner's title insurance policy | Buyer, by Collier custom | Buyer's cost |
| Master working capital contribution | Per the contract | Board-set; stated on the estoppel |
| Brokerage commission | Seller | As negotiated in your listing agreement |
The $1,556,250 figure is the midpoint of the two 2025 Santa Rosa sales, used for illustration only. The proration line is 181 days of the $7,692 median 2026 preliminary tax bill. Your own net sheet uses your contract price, tax bill, closing date and estoppel figures.
A Santa Rosa at Olde Cypress seller owes the Florida Statutes 720.401 homeowners association disclosure summary before the buyer signs, because both the Santa Rosa association and the Olde Cypress master association are Chapter 720 homeowners associations with no condominium behind the gate. Every seller also owes known material facts, the flood disclosure and the property tax disclosure summary.
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 owner supplies it. The contract must carry the statutory voidability language in conspicuous type. If the summary is missing, 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.
You, the seller, owe the disclosure summary before the contract is signed; the master working capital contribution under Section 8.13 is collected at transfer. The public documents we read do not show the Olde Cypress declaration restating the 720.401 duty, so the statute alone sets it. This is general information, not legal advice; your closing agent or attorney confirms it for your contract.
Since October 1, 2024, Florida Statutes 689.302 requires a residential seller to disclose, at or before contract, any flood insurance claim, any federal flood disaster assistance and any known flood damage. On Monteverde Way, pair the form with your elevation certificate and any FEMA letter for your address.
Florida Statutes 689.261 requires a summary warning the buyer not to rely on the seller's current taxes, because the assessment resets after a sale. With nine Santa Rosa homes carrying no homestead exemption and eighteen carrying one, that reset is real on this street.
Florida law requires a home seller to disclose known facts that materially affect value and are not readily observable, under Johnson v. Davis, 480 So. 2d 625 (Fla. 1985). Past roof leaks, storm repairs, open permits and water intrusion belong in the disclosure; a disclosed defect is simply part of the price.
Flood zone affects a Santa Rosa at Olde Cypress sale through the buyer's lender and insurer. On FEMA's effective May 16, 2012 map, 12 Santa Rosa footprints sit wholly in Zone AH, 11 partly and 4 in Zone X; on FEMA's March 20, 2025 preliminary map all 27 fall in Zone X. The preliminary map is not yet effective.
Zone AH is FEMA's shallow ponding zone, and nearby base flood elevation lines read 12.0 to 12.5 feet NAVD88, per FEMA's effective National Flood Hazard Layer overlaid on Collier County footprints. "Partly" means any overlap at all, even a lanai corner. Every FEMA letter we read here names ponding and overland flow, not the Gulf, as the flooding source.
Three Monteverde Way homes hold FEMA letters issued between 2017 and 2022 reading "Structure removed" from the Special Flood Hazard Area. LOMA 17-04-2382A records a lowest adjacent grade of 14.6 feet NAVD88 and LOMA 22-04-3044A 13.8 feet. A letter is address-specific; if your home touches Zone AH and has none, a licensed surveyor can tell you whether one is worth pursuing before you list.
FEMA's preliminary flood map places all 27 Santa Rosa homes in Zone X. Collier County opened the 90-day appeal period on August 19, 2026 and targets summer 2027, per its August 2026 release. Until then the 2012 map governs lending, and a seller should not market a draft; lenders decide per building.
Olde Cypress sits in Collier County Evacuation Zone E and the state's Category 4 storm surge zone, about 6.7 miles inland. Collier County's building code layers put the design wind speed for houses at 160 mph. Nine Santa Rosa homes appear in the 2000 or 2002 aerial layers and were likely permitted before the 2002 statewide Florida Building Code; their buyers' insurers will want the re-roof permit, wind mitigation form and opening protection documented.
Your Santa Rosa 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.
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, and the fee includes basic exterior landscaping of each home. The Santa Rosa amount is published only on the resident portal, so the estoppel is the reliable figure.
Social dues are payable as the club sets them from time to time under Section 14.02; golf initiation and dues are separate and optional, and the club publishes none of them. Third-party figures online conflict widely, from roughly $45,000 to $175,000 for golf initiation, and none is club-published. We ask the club's membership office at (239) 596-4797 for written figures before your listing goes live.
The median Santa Rosa bill on the 2026 preliminary roll is $7,692, but a buyer does not inherit the seller's Save Our Homes cap: the year after purchase the assessment resets toward just value, and the first full bill is usually higher. The 2025 millage was 9.5058 mills, per a 2025 Collier County Tax Collector bill inside Olde Cypress.
Olde Cypress has no Community Development District. Collier County's CDD layer shows none over the community, and the only non-ad valorem line on the sampled 2025 bill was garbage at $261.91. Older descriptions claiming a CDD are wrong.
The Olde Cypress rules that affect a Santa Rosa sale are the master leasing limits, the two-step architectural review, the overnight parking rule and the realtor sign rules, with any Santa Rosa rules in the neighborhood's own 2011 amended declaration on top. A buyer's agent will ask about each.
Under Section 9.13 of the master declaration and the 2013 leasing amendment, no lease may run under 60 days and no home may carry more than four leases a year, with a $100 application fee and a $1,000 refundable deposit. A lease in place transfers with the home unless the contract says otherwise, so share it early.
Exterior changes need approval from both the neighborhood and the master architectural committees, no vehicle may be parked on the streets overnight, and no more than two cars may sit in a driveway. Section 9.18 allows common household pets, leashed outdoors. The Santa Rosa 2011 amended declaration belongs in the buyer's file beside the master documents.
A Santa Rosa at Olde Cypress home has spent 7 to 34 days on market in each of the four MLS closings since September 2022; add about 30 to 60 days for inspections, the estoppel and a financed closing. Across Olde Cypress, about 59 percent of 48-month closings landed from January through May.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Two to four weeks to prepare: the valuation, a pre-listing inspection and wind mitigation report, the club's written figures, the estoppel request and the flood file. Then the market period, which in Santa Rosa has run from one week to five. Then a contract period of 30 to 60 days. Plan backward from the date you need to close.
One in three Santa Rosa homes carries no homestead exemption, so many Santa Rosa 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.
Your Santa Rosa listing should say what a portal cannot: a fairway behind every home, a P.B. Dye course and a clubhouse renovated in 2025 and 2026, one staffed gate, A-rated assigned schools, and a location about 1.6 road miles from I-75. Each is a sourced fact about the Olde Cypress community, not an adjective.
The course is 18 holes, par 72, a P.B. Dye design whose greens were resurfaced and 98 bunkers rebuilt in 2021, per Golfweek. The club's first renovation phase reopened in early March 2026 and the Greenside Grille opened in late April 2026, a $16 million project funded by the club's owner with no member assessment.
Monteverde Way is zoned for 2026 to 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 2024, 2025 and 2026, as republished from Florida Department of Education data by the Naples Daily News.
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, on a free-flow routing model.
You get a free Santa Rosa at 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 four Monteverde Way MLS closings, the county record and Terramar's live listings, with your buyer's club, fee and tax picture beside it. No cost and no obligation.
You receive every Santa Rosa sale with its date and source, a 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, and a recommended list price with a defensible range. Request it through our Santa Rosa at Olde Cypress home valuation page or the McGreevy and Comisar valuation form.
Call Jesse McGreevy direct at (239) 898-6072 or email [email protected]. Call Marc Comisar at (239) 287-5873. The office is at 24031 S Tamiami Trl #101, Bonita Springs, FL 34134. Buying as well? Read how we represent buyers in Naples.
Few Santa Rosa homes come up for sale: two in the last twelve months, none in all of 2022. The owner who sells next should see the evidence and the number before committing to anything, and should call us first, because the next Santa Rosa sale sets the comparable for every neighbor after it.
McGreevy and Comisar are a top-reviewed listing team on Google, and the quotes below are genuine five-star client reviews any Santa Rosa at Olde Cypress seller can check, 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.
★★★★★ "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!" Verified Google review
On a street with no competing listing, the qualified buyer is the whole game.
★★★★★ "Jesse was very professional, helpful and kept in touch with ideas and suggestions which developed into a sale. Highly recommend his company for their excellent follow through." Verified Google review
★★★★★ "Working with Jesse was easy, I was kept up to date on all feedback from showings and the many open houses. Highly recommend!" Verified Google review
★★★★★ "Marc and Jesse were amazing to work with AGAIN! We just sold our 3rd home with them and couldn't have been happier! If we ever move again we'll always call Jesse and Marc!" Verified Google review
A Santa Rosa at Olde Cypress specialist matters because the facts that decide this sale live in documents rather than in a listing feed: two MLS development names for one street, a club membership that passes by covenant, fees nobody publishes, three FEMA letters on Monteverde Way, and a neighborhood that sells once a year or less.
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 runs pricing, marketing, data and the association paperwork. Reach him at (239) 898-6072, and read his Jesse McGreevy agent profile.
Marc Comisar is a licensed Florida REALTOR and Broker Associate with Domain Realty and the other half of McGreevy and Comisar. He runs showings through the gate, buyer agent conversations, inspections and the on-site work that lets an out-of-state owner sell without flying down. Reach him at (239) 287-5873, and read his Marc Comisar agent profile.
A general agent may price a Santa Rosa home off the Olde Cypress median, search only one MLS development name, quote a club figure from a portal, repeat the old CDD claim or market the preliminary flood map as if it were effective. For the community-wide view, see our Olde Cypress seller page; for the street itself, our Santa Rosa at Olde Cypress neighborhood guide.
Two in three Santa Rosa at Olde Cypress 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.
Some owners move from Santa Rosa to a larger Da Vinci Estates home or a smaller Santorini villa, and the social membership follows the new deed under the same covenant. If your next home is here, see how we help buyers purchase in Santa Rosa at Olde Cypress, and value the home you are leaving through our Santa Rosa home valuation.
If your next home is elsewhere, start with how we represent buyers in Naples, our Naples real estate guide, or call Marc Comisar at (239) 287-5873. Homestead status is fixed on January 1 each year, and we sequence both closings around that date.
These are the questions Santa Rosa at Olde Cypress owners in Naples ask before they sell, covering price, timing, the club, HOA 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.
Start with a valuation built from the four Monteverde Way MLS closings and the county record, then assemble the file a 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. Call Jesse McGreevy at (239) 898-6072 to start.
One who prices from every Santa Rosa sale rather than the community median, 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.
It depends on size, plan, fairway exposure, build year and condition. The four MLS closings since September 2022 ran from $1,229,000 to $1,825,000, and the two December 2025 sales closed at $1,512,500 and $1,600,000. Request a written valuation on our Santa Rosa home valuation page.
$1,600,000 on December 4, 2025, $1,512,500 on December 2, 2025, $1,229,000 on April 8, 2024 and $1,825,000 on February 24, 2023, all on Monteverde Way, per the Southwest Florida MLS.
None. On September 26, 2026 the Southwest Florida MLS showed no Santa Rosa home active or pending. The nearest listings were two Terramar homes at $1,825,000 and $1,669,900.
Twenty-seven detached single-family homes on the 2026 preliminary Collier County roll, 26 on Monteverde Way and one on Olde Cypress Drive, inside the 548-home gated community of Olde Cypress.
Rarely. Collier County recorded 44 qualified Santa Rosa sales from 2001 to its August 29, 2026 file, 10 in the last ten years and 2 in the last twelve months. No qualified sale recorded in 2022.
The four MLS closings since September 2022 spent 7, 21, 34 and 34 days on market. Add 30 to 60 days for inspections, the estoppel and closing.
The four closings reached 98.46, 96.03, 92.48 and 93.59 percent of the final list price. None closed at or above list.
With no Santa Rosa listing and about 2.3 months of supply across Olde Cypress, supply favors the seller. Every Santa Rosa buyer of the last four years still negotiated, so price discipline matters.
Santa Rosa has 27 homes to Terramar's 55, both entirely on the golf course. Santa Rosa's 48-month rate of $501.70 per living square foot (small sample) runs above Terramar's $446.14, but Terramar has two listings today and Santa Rosa none.
Waiting makes sense only with a reason: a lease, a tax date or a repair. The street has no competing listing now, and the two 2025 sales set strong comparables. We will show you the evidence either way.
About 59 percent of Olde Cypress MLS closings over 48 months landed from January through May, yet both 2025 Santa Rosa sales closed in December. Listing in November or December meets the season's buyers as they arrive.
A model needs many recent similar sales; Santa Rosa had two in a year. It borrows other neighborhoods' sales, cannot see your fairway exposure and cannot read a FEMA letter.
The social membership does, automatically, under Section 14.02 of the master declaration. Golf is a separate, optional purchase from the club, and the club describes its golf model as non-transferable.
No. The Club at Olde Cypress is privately owned and non-equity, so there is no equity certificate to redeem.
The club does not publish them. Third-party figures conflict widely and none is club-published; we obtain the current written figures from the club's membership office at (239) 596-4797 before listing.
No. Collier County's CDD layer shows none over Olde Cypress, and the only non-ad valorem line on a sampled 2025 bill was garbage at $261.91.
The Santa Rosa association invoices quarterly, including the master share and basic exterior landscaping, but the amount is published only on the resident portal. The estoppel certificate is the reliable figure.
The Santa Rosa association is not run through the master association's manager, and its state filing lists an outside registered agent. We confirm who issues the estoppel before you list.
Section 8.13 lets the master association collect one at transfer of title, in a Board-set amount we could not locate publicly. The estoppel states it, and the contract decides who pays.
It is the association's statement of what is owed on your home. Florida Statutes 720.30851 caps the fee at $299, plus $119 for rush delivery; in Collier County the seller customarily pays.
The Florida Statutes 720.401 homeowners association disclosure summary, before the buyer signs. Missing it lets the buyer void the contract until closing.
Known material defects under Johnson v. Davis, the flood disclosure under Section 689.302, the property tax disclosure summary under Section 689.261 and the 720.401 summary. Disclose roof, storm and water history completely.
On the effective 2012 FEMA map, 12 Santa Rosa footprints sit wholly in Zone AH, 11 partly and 4 in Zone X; the March 2025 preliminary map puts all 27 in Zone X, but it is not effective yet. Check your address for a FEMA letter.
Yes, for a financed buyer. Three Monteverde Way homes hold letters removing the structure from the flood hazard area; a letter for your address answers the lender's flood question on day one.
Evacuation Zone E on Collier County's layer, in the state's Category 4 storm surge zone, about 6.7 miles inland.
Usually, if you are homesteaded. The median Santa Rosa bill is $7,692 on the 2026 preliminary roll, and a buyer's assessment resets toward just value after the sale.
In Collier County the buyer customarily pays the owner's title policy and chooses the closing agent. The contract controls, so confirm it in writing.
Yes, within the master association's rules: public open houses Saturday and Sunday from noon to 5 p.m., signs from the guard house against a $20 deposit, and one standardized green wooden For Sale sign.
No. Fairway Preserve at Olde Cypress is a 264-unit condominium with its own gate off Immokalee Road, outside the master association and the club covenant.
Request a Santa Rosa home valuation and ask the club and your association for their written figures. Call Jesse McGreevy at (239) 898-6072.
Every Santa Rosa at Olde Cypress figure on this page traces to a primary source below, as of September 2026: the MLS, the county roll and recorded sales (cited in plain text), recorded declarations, state filings, the club, Florida Statutes and FEMA. No listing portal or competing brokerage is cited.
Market data and county records
The associations, state filings and recorded documents
The Club at Olde Cypress
Florida statutes and state agencies on selling
Flood, storm and insurance
Schools and location
Our related pages
Every row below links the authority that publishes the document, so a Santa Rosa at Olde Cypress seller sees the official version; documents that are not public are named at the end.
| Document | What it settles | Official authority |
|---|---|---|
| Santa Rosa at Olde Cypress 2011 amended declaration, OR 4722 PG 375 | The neighborhood's covenants, articles and bylaws | Olde Cypress Master Association, PDF |
| 2019 Amended and Restated Declaration for Olde Cypress, OR 5700 PG 1118 | Mandatory social membership (14.02), the working capital contribution (8.13), leasing, pets and parking | Olde Cypress Master Association, certified PDF |
| 2013 leasing amendment, OR 4874 PG 3783 | The 60-day minimum and four leases a year | Olde Cypress Master Association, PDF |
| Olde Cypress neighborhood site map | Where Santa Rosa, the gate house and the clubhouse sit | Olde Cypress Master Association, image |
| Community access and gate procedures | How guests and buyers are admitted | Olde Cypress Master Association, PDF |
| Florida Statutes 720.401 | The pre-contract disclosure summary | Florida Senate |
| Florida Statutes 720.30851 | Estoppel contents and fee caps | Florida Legislature |
| Florida Statutes 689.302 | The residential flood disclosure | Florida Legislature |
| FEMA Map Service Center | The flood zone and any letter for your address | FEMA |
Documents that matter to a Santa Rosa sale but are not public: the club's current dues and golf figures, from the membership office at (239) 596-4797; the Santa Rosa association's budget and quarterly assessment; the master working capital contribution amount; and the estoppel certificate for your home.
McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008, list and sell homes across Southwest Florida from an office in Bonita Springs, and Santa Rosa at Olde Cypress sits inside the North Naples market we work every week. Few Santa Rosa homes come up for sale in a year, so the owner who sells next should call us first for a Santa Rosa at Olde Cypress home valuation; buyers can start with how we represent buyers in Naples.
Jesse McGreevy (Sales Associate, FL Lic. SL3101296) and Marc Comisar (Broker Associate, FL Lic. BK3060671) 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. 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.
