Updated September 2026
Buy on Monteverde Way with the Top 1% Real Estate Agents Nationally Since 2008. Every Santa Rosa at Olde Cypress MLS sale since 2022, 44 county sales since 2001, the club, flood letters and costs. Sell or buy with McGreevy and Comisar.
Updated September 2026 · By Jesse McGreevy and Marc Comisar, Domain Realty
Buying a home in Santa Rosa at Olde Cypress means buying one of 27 detached golf-course homes, 26 of them on Monteverde Way, inside the gated club community of Olde Cypress in North Naples, Florida 34119. The street trades rarely: four Southwest Florida MLS closings in 48 months, none of them at full list price, and no Santa Rosa home was for sale on September 26, 2026. This page is the purchase side of our Santa Rosa at Olde Cypress neighborhood guide, which sits inside our Olde Cypress community guide: what a Santa Rosa home has cost, what it costs to own, what to request before you are committed, and how we negotiate for you.
If you are still choosing an agent, our guide to the best real estate agents in Naples sets the city's teams side by side on the public record. If you already own a Santa Rosa home and are weighing a move, start with how we sell homes in Santa Rosa at Olde Cypress and a data-backed Santa Rosa at Olde Cypress home valuation, or call Jesse direct at (239) 898-6072.
Call Marc Comisar at (239) 287-5873 or Jesse McGreevy at (239) 898-6072. We have been Top 1% Real Estate Agents Nationally Since 2008, and before you tour a single Monteverde Way home we will show you every Santa Rosa sale on the record.
Buying a home in Santa Rosa at Olde Cypress takes patience and preparation: 27 golf course homes, a sale every year or two, no home listed today, two association layers whose fees are not published, a club social membership that comes with the deed, and a flood file where three Monteverde Way homes already hold FEMA letters.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Every figure below comes from the county roll and deed record, the MLS, the recorded declarations, the club's pages, Florida Statutes and FEMA; where the record stops, we name the document that holds the answer.
The 2026 preliminary Collier County roll counts 27 single-family homes in Santa Rosa, 26 on Monteverde Way and one on Olde Cypress Drive, about 5 percent of the 548 homes behind the Olde Cypress gate (the master association rounds to 550). Monteverde Way branches off Olde Cypress Drive in the middle of the community.
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 that only Terramar, Egret Cove and Biscayne Place also reach. Lots run 8,602 to 16,006 square feet, median 9,907, or about 0.23 acres on the roll. For a buyer, the choice inside Santa Rosa is between fairway exposures, not between golf and no golf.
County building footprints show nine homes by 2002 and two by 2004, then fourteen by 2006 and two by 2007; the 2026 preliminary roll dates the homes 2000 to 2007, median 2005. The wave decides which building code a home was permitted under, and your insurer will ask.
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. 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, has its own condominium association and no club membership, and is not part of the gated community.
Santa Rosa at Olde Cypress buyers work with McGreevy and Comisar because a street with four MLS sales in four years is priced from the record, not from a portal estimate. We have been Top 1% Real Estate Agents Nationally Since 2008 and the #1 Team in Southwest Florida since 2012, and we pull every Santa Rosa sale ourselves.
Those are career numbers across Lee and Collier County.
In the last 12 months Santa Rosa at Olde Cypress has seen 2 resales. This page carries no story of a Santa Rosa buyer we represented, because we will not print one we cannot document. 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. The sale walked through below is a public-record sale, labelled as one.
McGreevy and Comisar are a top-reviewed Santa Rosa at Olde Cypress buyer's agent team on Google. The quotes below are genuine Google reviews in the client's own words; every review is on our Google Business Profile.
★★★★★ "Marc is extremely knowledgeable, professional and a true pleasure to work with. He kept us informed throughout the process and went over and beyond our expectations to ensure an extremely smooth process." Verified Google review
★★★★★ "Marc and Jesse are truly great people and they care about the people that they work with. Marc made our house purchase seamless and we closed within 30 days. If you want someone that's gonna treat you like family, well you found them." Verified Google review
★★★★★ "He knew the area and therefore knew exactly where to take us to find the exact kind of neighborhood we were looking for and he was right on the money." Verified Google review
★★★★★ "We used Jesse to represent us on purchasing a property in Naples, and he worked our deal like it was for him! 100% satisfied." Verified Google review
Santa Rosa at Olde Cypress is a small, high-priced golf street in North Naples that sells rarely and has always sold below its final list price in the MLS record. The takeaways below condense what a Santa Rosa buyer in Naples needs before choosing a home, an offer and an agent.
The Santa Rosa at Olde Cypress market is thin and patient: two MLS closings in the twelve months to September 26, 2026, at $1,512,500 and $1,600,000, no home active or pending on that date, and four closings in 48 months, none at full list. A buyer here waits for a home, then negotiates from a short record.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
No MLS window for Santa Rosa reaches ten closings: 2 in 12 months, 2 in 24, 3 in 36 and 4 in 48, the widest window we pulled. So this page lists every sale instead of leading with a median, and uses the county's recorded sales since 2001 as the long view.
| 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, each sale assigned to Santa Rosa by street address against the county roll. Sold-to-list is measured against the final list price. Total volume across the four was $6,166,500.
Over 48 months (n=4, small sample) the median sold price is $1,556,250, the mean of the middle pair, $1,512,500 and $1,600,000; the median is $501.70 per living square foot, 94.81 percent of final list and 27.5 days on market. Over 12 months (n=2, small sample) the median is the same $1,556,250, at $572.50 per living square foot, 97.25 percent and 20.5 days.
The Southwest Florida MLS files Santa Rosa listings under two development names, OLDE CYPRESS and SANTA ROSA AT OLDE CYPRESS. A saved search on one name alone can miss a Santa Rosa home, so we search both and match each listing to Monteverde Way by address.
| 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-final-list | 96.03% and 98.46% | Median 97.52% |
| Days on market | 7 and 34 | Median 29 (n=24) |
| Active and pending, September 26, 2026 | 0 and 0 | 5 active, 1 pending or contingent |
| Months of supply | No listing to measure | About 2.3 |
Both Santa Rosa closings of the year sold above the community's median price per living square foot. Santa Rosa carried 2 of the 26 Olde Cypress closings, roughly its share of the homes.
None of the four Santa Rosa closings reached its final list price; the gaps ran $25,000 to $125,000. Across Olde Cypress, 6 of 26 closings in the last twelve months did. The December 2025 pair negotiated 1.5 to 4 percent, the 2023 and 2024 buyers about 6.4 to 7.5 percent: real room, but not the 10 percent some buyers hope for.
On September 26, 2026 no Santa Rosa home was active or pending. The nearest listings were two Terramar Drive homes: $1,825,000 for 2,816 square feet after 133 days and $1,669,900 for 3,255 square feet after 17 days. For live Olde Cypress inventory, see our team's listings on DomainRealtyGroup.com, or ask Marc about owners who may sell before they list. Own on Monteverde Way? Get a Santa Rosa home valuation or call Jesse direct at (239) 898-6072. Buying? Read how we represent buyers in Naples or call Marc at (239) 287-5873.
Santa Rosa at Olde Cypress has recorded 44 qualified sales in Collier County's deed file since 2001, at an all-history median of $742,500 (n=44, the mean of $735,000 and $750,000). The ten most recent run from $675,000 in December 2020 to $1,825,000 in February 2023, and the two 2025 sales recorded at $1,512,500 and $1,600,000.
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 |
| 24 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) |
Source: Collier County Property Appraiser recorded qualified sales, improved, over $100,000, data file dated August 29, 2026; a qualified sale is one the county graded arm's-length.
| 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 not shown, including 2022 and 2026 to the file's newest recording on May 22, 2026, had no qualified Santa Rosa sale. From 2010 to 2020 prices held between about $650,000 and $800,000; each year is one to six houses, a record rather than 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 |
All ten are on Monteverde Way. The county dates a sale by its deed, so the December 2025 MLS closings appear with late-November dates; we never blend county and MLS figures into one number.
Santa Rosa at Olde Cypress has recorded 44 qualified sales since 2001, only two in the last twelve months, and had no home for sale on September 26, 2026, so the buyer who is ready when a Monteverde Way home appears is the one who gets it. Request your Santa Rosa at Olde Cypress buyer consultation, read how we represent buyers in Naples, or call Marc at (239) 287-5873. Own a Santa Rosa home already? Request a free Santa Rosa at Olde Cypress home valuation or call Jesse direct at (239) 898-6072.
A buyer can learn three things from the most recent Santa Rosa at Olde Cypress sales: smaller homes have earned the highest price per square foot, a quick sale still left room below list, and a December closing found a buyer outside the season. The December 2025 pair on Monteverde Way is the best current evidence.
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, was listed at a final $1,575,000, went under contract after 7 days and closed on December 2, 2025 at $1,512,500: 96.03 percent of list and about $593 per square foot, the highest rate of any Santa Rosa sale in the four-year pull. The buyer moved fast and still negotiated $62,500. For the next buyer the lesson is that speed and price are not opposites on this street: be pre-approved, have the club and association questions ready, and write a firm offer anchored to the recorded sales rather than to the list price.
On December 4, 2025 a larger Monteverde Way home, 2,898 square feet with four bedrooms plus a den, closed at $1,600,000 after 34 days, 98.46 percent of list and about $552 per square foot. The extra 347 square feet added $87,500 and lowered the per-foot rate by about $41.
The April 2024 sale, 2,946 square feet at $1,229,000 and about $417 per square foot, was nearly the size of the December $1,600,000 home and sold for $371,000 less: that is what condition, updates and timing can be worth on one street.
An appraiser looks first for same-neighborhood sales of similar size within six to twelve months. In Santa Rosa that is two sales at most, so expect Terramar, Egret Cove and Unit One comparables, and we assemble that set before you offer.
Santa Rosa at Olde Cypress sits in the upper middle of the community's price ladder: its 36-month recorded median of $1,512,500 (n=3, small sample) trails only Da Vinci Estates, Unit One and the single Strada Bella sale, while its median 2026 preliminary just value of $1,079,324 ranks sixth of eleven county groupings.
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) | Median 2026 preliminary taxes |
|---|---|---|---|---|---|
| Biscayne Place | 8 | $1,704,810 | No sale in 36 months | Counted with Treeline Drive | $15,120 |
| Da Vinci Estates | 60 | $1,657,416 | $2,387,500 (12) | $2,150,000 (17) | Not available |
| Olde Cypress Unit Two | 69 | $1,453,941 | $1,305,000 (6) | Wild Orchid Court $1,929,111 (6) | $10,252 |
| Strada Bella | 18 | $1,365,158 | One sale, $1,775,000 | One sale, $1,775,000 | $9,545 |
| Olde Cypress Unit One | 61 | $1,294,566 | $1,847,500 (6) | Treeline and Olde Cypress Drive $1,695,000 (16) | $8,438 |
| Santa Rosa | 27 | $1,079,324 | $1,512,500 (3) | $1,556,250 (4) | $7,692 |
| Lantana | 122 | $1,045,298 | $1,320,000 (17) | $1,335,000 (28) | Not available |
| Terramar | 55 | $965,006 | $1,137,000 (8) | $1,400,000 (11) | $7,334 |
| Egret Cove | 18 | $828,724 | No sale in 36 months | Two sales, $1,025,000 and $1,200,000 | $5,096 |
| Lone Pine (Unit Three) | 55 | $783,010 | $972,500 (8) | $1,000,000 (9) | $5,754 |
| Santorini Villas | 55 | $558,186 | $640,000 (11) | $645,000 (13) | $4,720 |
Just value is the county's mass-appraisal estimate for taxation, not a sale price, and the tax medians describe current owners, many homesteaded. 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. The roll's tax field was not populated for Da Vinci Estates and Lantana in the data pulled.
Santa Rosa's 36-month recorded median runs about 40 percent above its median just value, so the county's number is no guide to price. Buyers wanting a lower entry on a golf lot look at Terramar and Egret Cove; buyers wanting estate lots look at Da Vinci Estates, Strada Bella and Biscayne Place. Neighbors with their own guides include Egret Cove at Olde Cypress and Lantana at Olde Cypress. Owners can see where their home sits with a Santa Rosa home valuation, or call Jesse direct at (239) 898-6072; buyers can read how we represent buyers in Naples or call Marc at (239) 287-5873.
Owning a Santa Rosa at Olde Cypress home each year costs a quarterly Santa Rosa association invoice that includes the Olde Cypress master share, mandatory club social dues, any golf membership you choose, property taxes at the 2025 rate of 9.5058 mills, a homeowners policy and flood insurance where your lender requires it. The association and club amounts are not published.
Data updated: September 2026 (Olde Cypress Master Property Owners Association About page; The Club at Olde Cypress membership and About Us pages; 2025 Collier County Tax Collector bill; OpenFEMA NFIP policies as of September 8, 2026)
| Layer | Amount | How often | Source |
|---|---|---|---|
| Santa Rosa assessment, including the master share | Not published (resident portal only) | Quarterly | Master association About page |
| Golf membership, Full or Associate | Optional; initiation and dues not published | Initiation plus annual | Club membership page |
| Private golf cart on the course | $1,950 | Annual | Club article |
| Member assessments and food minimum | None | Not applicable | Club About Us page |
| Property taxes | 9.5058 mills in 2025; Santa Rosa median $7,692 on the 2026 preliminary roll for current owners | Annual | 2025 Collier County tax bill |
| Garbage, non-ad valorem | $261.91 on the 2025 sample bill | Annual | Same |
| Community Development District | None | Not applicable | Collier County CDD layer |
| Flood insurance | Median $1,259 per year, single-family, ZIP 34119 | Annual, where required or chosen | OpenFEMA NFIP policies |
| Master working capital contribution | Board-set; amount not located publicly | Once, at transfer | 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 |
The invoice pays Santa Rosa's own costs, chiefly its road tract, which the association owns on the 2026 preliminary roll, plus your master share: the gatehouse, private roads, lakes, the 158.59-acre master preserve and basic exterior landscaping of each home, per the master association's About page. Ask for both budgets during your inspection period.
Santa Rosa is one of two Olde Cypress associations whose state corporate filing lists an outside St. Petersburg property management company as registered agent, not the manager most neighborhoods share. The estoppel and budget come from that office, so allow time in your contract calendar.
Freddie Mac's Primary Mortgage Market Survey put the 30-year fixed rate at 7.03 percent as of September 24, 2026. At that rate, a Santa Rosa purchase at the $1,556,250 48-month median (n=4, small sample) with 20 percent down, a $1,245,000 loan, carries principal and interest of about $8,308 a month, before taxes, insurance, the quarterly invoice and club dues. A loan of that size is above the conforming limit, so expect jumbo underwriting, reserves requirements and an appraisal the lender reads closely. Your lender's quote replaces this illustration.
Club membership for a Santa Rosa at Olde Cypress buyer works in two tiers: social membership in The Club at Olde Cypress is mandatory and automatic when you acquire the home, under Section 14.02 of the recorded 2019 declaration, while Full Golf and Associate Golf are optional purchases. The club is non-equity and privately owned.
"By acquisition of a Parcel, each Owner automatically becomes a social member of The Club at Olde Cypress," under Section 14.02 of the 2019 Amended and Restated Declaration for Olde Cypress, recorded at OR 5700 PG 1118, with dues set by the club. Every Monteverde Way owner carries it.
The club describes itself as non-equity and privately owned by the Stock family of companies, which has held the course land since 1998; Section 14.03 gives owners no equity or vote. The club states it has no member assessments, and its $16 million clubhouse renovation, finished in April 2026, carried none.
Social members use the clubhouse and dining, four clay tennis courts, two pickleball courts, the fitness center and the pool, all west of the Treeline Drive gate. Golf is available only as a golf member's guest.
A fairway view does not include playing the course. Full Golf and Associate Golf, the latter limited from November through April, are sold separately per the club's membership page; initiation and dues are not published, so get them in writing from the membership office at (239) 596-4797.
Third-party figures for Olde Cypress golf initiation conflict widely, from roughly $45,000 to $175,000, none published by the club, and some describe an equity structure the club says it does not have. We quote none of them as a price.
Buying a home in Santa Rosa at Olde Cypress runs in nine steps: prepare before a home appears, budget the carrying costs, check the building's flood letter, sign a buyer agreement and get jumbo pre-approval, write the offer with the right calendar, collect the disclosure summary and estoppel, get the club's figures, clear inspections and insurance, and close.
With no Santa Rosa home active on September 26, 2026, set a saved search on both MLS development names and decide whether Terramar or Egret Cove would also work for you.
Add the quarterly Santa Rosa invoice, club social dues, any golf, taxes on your purchase price rather than the seller's bill, and insurance, and ask for the unpublished figures as soon as a home is under consideration.
Ask whether the home holds one of the three Monteverde Way FEMA letters, request the elevation certificate, and let your lender run its own flood determination.
Since August 17, 2024, buyers sign a written agreement before touring. At Santa Rosa prices most financed purchases are jumbo loans, so get a full underwriting pre-approval.
Build the inspection period around the documents from two associations and the club, and the appraisal period around an appraiser who may need Terramar sales.
The seller owes you the Chapter 720 disclosure summary before you sign; the estoppel, ordered after contract, states the assessment and any capital contribution due.
Ask the membership office at (239) 596-4797 for social dues and any golf initiation and dues, and make golf a contingency if it matters to you.
Order a full inspection, a four-point and a wind mitigation report, and bind insurance early; on 2000 to 2007 homes the roof date and openings drive the premium.
Close with the title company you chose, file for homestead by March 1 of the following year if it is your primary residence, and enroll with the club and the gate.
A Santa Rosa at Olde Cypress buyer should request the Chapter 720 disclosure summary before signing, the recorded 2019 master declaration and the 2011 Santa Rosa restatement, the master and Santa Rosa budgets, the estoppel certificates, the club's written dues and golf figures, the elevation certificate and any FEMA letter, and the seller's disclosures.
Under Florida Statutes 720.401, a prospective parcel owner "must be presented a disclosure summary before executing the contract for sale," and on a resale the seller supplies it. If it is not delivered, you 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. Santa Rosa is a Chapter 720 homeowners association; there are no condominiums behind the Olde Cypress gate.
Our Santa Rosa seller page reads identically: the seller owes the disclosure summary before contract; the master association may collect a working capital contribution at transfer under Section 8.13, in a Board-set amount we could not locate publicly; the contract says who pays. This is information, not legal advice.
Under Florida Statutes 720.30851, an association's estoppel states the regular assessment, its frequency, what is paid through, any balance and any capital contribution or transfer fee due at closing. In Santa Rosa, confirm the certificate covers the master share, and ask to see it before your inspection period ends.
The 2011 Santa Rosa restatement (OR 4722 PG 375, restating OR 3057 PG 2810 and the 2006 version at OR 4144 PG 425), the 2019 master declaration, the 2013 leasing amendment, the master documents library, the club's membership documents and the Santa Rosa budget. Where the two declarations differ, the stricter rule generally governs.
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, shallow ponding, 11 partly in Zone AH and 4 wholly in Zone X. FEMA's March 20, 2025 preliminary map shows all 27 in Zone X, but that map is not effective yet, and three homes hold structure-removal letters.
Data updated: September 2026 (FEMA National Flood Hazard Layer, effective and preliminary, overlaid on Collier County building footprints, computed September 23, 2026)
| Santa Rosa at Olde Cypress | Count |
|---|---|
| Homes | 27 |
| Footprint wholly in Zone AH | 12 |
| Footprint partly in Zone AH | 11 |
| Footprint wholly in Zone X | 4 |
| Nearby base flood elevation lines | 12.0 to 12.5 feet NAVD88 |
Two test points on Monteverde Way a short distance apart show how fine the line is: one sits wholly in Zone AH near a 12.5-foot base flood elevation line, the other wholly in unshaded Zone X near a 12.0-foot line. A neighbor's answer is never yours. Every FEMA letter we read for Olde Cypress streets names the flooding source as ponding and overland flow, not the Gulf; there is no Zone VE or Coastal High Hazard Area here.
Three Monteverde Way homes hold FEMA Letters of Map Amendment removing the structure from the Special Flood Hazard Area: LOMA 17-04-2382A issued February 13, 2017, recording a lowest adjacent grade of 14.6 feet NAVD88; 18-04-1451A issued January 11, 2018; and LOMA 22-04-3044A issued June 28, 2022, recording 13.8 feet. A LOMA covers only the structure it names. If the home you like is one of the three, ask the seller for the letter; if it is not, an elevation certificate may show whether one is possible.
On FEMA's preliminary National Flood Hazard Layer, issued March 20, 2025, every Santa Rosa footprint falls in Zone X, with every other home inside the Olde Cypress PUD. Collier County opened the 90-day appeal period on August 19, 2026, with the new map targeted for summer 2027. Until FEMA finalizes it, the 2012 map governs lending.
Get the elevation certificate, search the address on the FEMA Flood Map Service Center, read the seller's flood disclosure under Florida Statutes 689.302, and get a flood quote even where it is not required; the ZIP 34119 median NFIP policy is $1,259 a year.
No public agency publishes a homeowners or windstorm premium for Santa Rosa at Olde Cypress, so we will not invent one. Flood is different: FEMA data shows a median single-family NFIP cost of $1,259 a year in ZIP 34119. The wind premium on a Monteverde Way home turns on the roof, the openings and the build wave.
A federally regulated lender will require flood insurance on a building in Zone AH, and most jumbo lenders apply the same rule; in Zone X it is not required, though a lender may still ask. Because the zone line runs lot to lot on Monteverde Way, the lender's determination on your building is the answer.
New work is designed to a 160 mph ultimate wind speed under the current Florida Building Code. Santa Rosa's first wave likely predates the 2002 statewide code; the 2006 homes were permitted under it. Impact openings, a newer roof and roof-to-wall connections earn wind mitigation credits. We did not read roof or window permits for individual homes.
Citizens Property Insurance fell from 6,042 Collier County homeowners policies at the end of 2024 to 1,839 by August 31, 2026, per its detail by county report, so a 2026 buyer generally has more private options.
Santa Rosa sits in Evacuation Zone E and Florida's Category 4 storm surge zone, about 6.7 miles inland, outside the Coastal High Hazard Area. Irma in 2017 produced 88 of ZIP 34119's 124 all-time NFIP claims, per the OpenFEMA claims dataset; the block group containing Olde Cypress shows 3 claims ever, none coded to Ian. Ask the seller for any wind repair invoices and permits.
Property taxes after you buy in Santa Rosa at Olde Cypress will be set on your purchase-year just value at the 2025 rate of 9.5058 mills plus a garbage charge, with no CDD. Your bill will usually be well above the seller's, because a buyer does not inherit the seller's Save Our Homes cap.
On the 2026 preliminary roll the 27 homes show a median total tax of $7,692 on a median just value of $1,079,324, with 18 of 27 homesteaded. As a rough check, a home assessed near a $1,556,250 purchase price would carry about $14,800 in ad valorem tax before any exemption.
If the home will be your primary residence, file for homestead by March 1 of the year after you buy. If you are leaving another Florida homestead, you may be able to transfer part of its accumulated Save Our Homes benefit, within statutory limits, which can narrow the gap to the seller's bill considerably.
The rules that decide fit in Santa Rosa at Olde Cypress are the master leasing limits, the overnight street-parking ban, two-step architectural review, the lake and golf-course easements and the pet rules. Each is in the recorded 2019 master declaration or its leasing amendment, and the 2011 Santa Rosa restatement can add stricter rules of its own.
No lease under 60 days, no more than four a year, whole home only, a $100 fee, a $1,000 refundable deposit and Board approval, under Section 9.13 of the master declaration. Read the Santa Rosa restatement for any added rule; seasonal rental works, vacation rental does not.
No vehicles may be parked on Olde Cypress streets overnight, and no more than two cars in a driveway. Monteverde Way is a short street of 26 homes, so a household with three cars should plan garage space before buying.
Exterior changes need Santa Rosa and master architectural approval, and on a golf lot the course edge is what review reads closely. No swimming or private boats on the lakes, and a 20-foot lake maintenance easement where it applies.
Common household pets are allowed under Section 9.18 of the master declaration, leashed outdoors and not left tethered on porches, lanais or in garages. Livestock, poultry and reptiles are prohibited.
Outside public open house hours, Saturday and Sunday from noon to 5 p.m., buyers enter with an agent or the owner, per the master association's community access procedures.
We find you the right Santa Rosa at Olde Cypress home by watching both MLS development names every day, knowing which Monteverde Way homes have not traded in years, and telling you honestly when Terramar or Egret Cove is the better fit. With no Santa Rosa listing on September 26, 2026, the right home may not be listed yet.
On a 27-home street where two-thirds of homes are homesteaded, some sales start as a conversation. We talk to owners and agents and bring you homes before they list when an owner is willing; we never promise one exists.
We tour with the four MLS sales, the county record, the flood letter and the club questions in hand, and arrange every visit with the gate in advance.
Create a saved search on our site and new Olde Cypress listings reach you the day they appear, filtered to Monteverde Way, your size and your budget. Your saved search routes to our team, so Marc sees what you are watching and can tell you what he knows about each home.
We negotiate a Santa Rosa at Olde Cypress purchase from the four MLS sales and ten recorded sales on Monteverde Way, the listing's time on market, the Terramar homes a buyer tours the same afternoon, and the costs the seller has not disclosed. Every recorded Santa Rosa buyer paid below list, and we know where that room comes from.
Before you offer, we place the home among the four closings by living area, den count, exposure and condition. An ask above that evidence is where the negotiation happens.
Terramar's two listings, at $1,825,000 and $1,669,900, are what a Santa Rosa seller competes with; a Santa Rosa price above them without a reason in the house is leverage we put in writing.
If the seller cannot produce the club's figures, the Santa Rosa budget or the flood letter, that uncertainty belongs in your price or your contingencies.
An aging roof or missing impact protection on a 2000 to 2007 home is negotiable as a credit or repair, and a short appraisal on a thin comparable set is a reason to renegotiate.
Marc Comisar and Jesse McGreevy negotiate every offer themselves. The person who analyzed the Monteverde Way comparables is the person on the phone with the listing agent.
Buyer closing costs in Santa Rosa at Olde Cypress include, by Collier County custom, the owner's title policy and the closing agent you choose, plus lender charges, Florida's documentary stamp tax on the note at $0.35 per $100, the intangible tax on the mortgage at $0.002 per dollar, recording, inspections, survey, prepaids and any capital contribution the contract assigns you.
On the illustrative $1,245,000 loan, Florida's documentary stamp tax on the promissory note at $0.35 per $100 is $4,357.50, and the nonrecurring intangible tax at $0.002 per dollar is $2,490, per the Florida Department of Revenue. A cash buyer pays neither.
In Collier County the buyer customarily chooses the closing agent and pays the owner's title policy, the opposite of the Lee County custom; the contract controls. The premium is state-promulgated under Florida Administrative Code Rule 69O-186.003.
The estoppel certificate fees are customarily the seller's in Collier County practice. The master working capital contribution under Section 8.13 is collected at transfer, and the contract decides who pays; any Santa Rosa contribution appears on its estoppel; the club may charge golf initiation if you join for golf.
Taxes and the quarterly Santa Rosa invoice are prorated to closing; you prepay homeowners and any flood insurance, and escrow taxes if your lender requires it.
Since August 17, 2024, buyers in Santa Rosa at Olde Cypress, as everywhere in the country, sign a written agreement with their agent before touring a home, and that agreement states the agent's compensation, which is fully negotiable. Offers of compensation to buyer agents can no longer appear in the MLS, though a seller may still agree to pay part of it.
The agreement sets what we do for you, for how long and for what compensation, per the National Association of REALTORS guidance on written buyer agreements. Read it before the first tour, and ask us any question about it.
Compensation is negotiable and not set by law: you, the seller as a negotiated concession, or the listing brokerage may pay it, as the NAR settlement FAQ explains. We show you plainly how each approach changes your Santa Rosa offer.
A Santa Rosa at Olde Cypress address comes with assignment to Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High, all rated A in 2024, 2025 and 2026; NCH Emergency Department Northeast about 2.4 road miles from the gate; I-75 Exit 111 about 1.6 miles away; and downtown Naples about 14.5 miles away.
Every Santa Rosa address is zoned for 2026 to 2027 to Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High, per the Collier County Public Schools address lookup, with grades from Florida Department of Education data republished by the Naples Daily News.
NCH Emergency Department Northeast, open 24 hours, is about 2.4 road miles from the gate.
From the Treeline Drive entrance: about 1.6 road miles to I-75 Exit 111 and 14.5 miles to Fifth Avenue South at free-flow speeds; round up in season.
Santa Rosa and Terramar at Olde Cypress are the two all-golf detached neighborhoods a Naples buyer tours together: 27 homes against 55, similar lots, every home on the course. Santa Rosa has recorded higher prices per square foot on far fewer sales and had nothing for sale on September 26, 2026; Terramar had two listings and more sales to price from.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
| Question | Santa Rosa at Olde Cypress | Terramar at Olde Cypress |
|---|---|---|
| Homes on the 2026 preliminary roll | 27 | 55 |
| Streets | Monteverde Way (26), Olde Cypress Drive (1) | Terramar Drive (43), Terramar Court (12) |
| Homes touching the golf course parcel | 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 |
| 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-final-list, 48 months | 94.81% (small sample) | 93.65% |
| Closings at or above list, 48 months | 0 of 4 | 1 of 11 |
| 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 |
| 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 |
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. Medians under ten sales are small samples.
Santa Rosa's 48-month median per living square foot runs about $56 above Terramar's and its median just value about $114,000 higher, on lots about 570 square feet smaller, partly because more than half of Santa Rosa dates to the 2004 to 2007 wave. Terramar sold as low as $850,000 in the window and offers more homes to choose from.
Choose Santa Rosa if you want a 26-home golf street in the middle of the community, a home from the later build wave and are willing to wait for one to list. Choose Terramar if you want to buy this season, want more listings and sales to compare, or want a slightly larger lot at a lower entry price. Terramar buyers get the same analysis on our Terramar at Olde Cypress buyer page. Selling a Santa Rosa home to move? See how we sell homes in Santa Rosa at Olde Cypress or call Jesse direct at (239) 898-6072. Buying on either street? Read how we represent buyers in Naples or call Marc at (239) 287-5873.
Santa Rosa at Olde Cypress is the right place for a Naples buyer who wants a detached golf-course home on a short, quiet street inside a gated club community, accepts social membership with the deed, values A-rated assigned schools and no CDD, and can wait for one of 27 homes to come to market.
You want a golf lot, a 2000 to 2007 home, a gate and a quiet street, and you are ready to act fast when a Monteverde Way home lists.
You must buy this month, need every carrying cost published before touring, want vacation rental income or a new build, or need overnight parking for more than two cars outside the garage.
Our Olde Cypress buyer guide covers all nine neighborhoods, which had five active listings and one pending on September 26, 2026, and the Olde Cypress community guide describes the gate and the club in full.
Your personalized Santa Rosa at Olde Cypress buyer consultation with McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008, starts with the contact form on this page or a call to Marc Comisar at (239) 287-5873. We cover every Monteverde Way sale, what a Santa Rosa home costs to own, the documents to request and how we would write your offer. No cost and no obligation.
Every Monteverde Way sale, the Terramar and Egret Cove alternatives, the carrying costs, the club and flood questions, a jumbo financing plan and your offer strategy.
Selling a Santa Rosa home first? Request a Santa Rosa at Olde Cypress home valuation or call Jesse direct at (239) 898-6072. Call Marc Comisar at (239) 287-5873, email [email protected], or use the contact form at the top of this page. The office of McGreevy and Comisar is at 24031 S Tamiami Trl #101, Bonita Springs, FL 34134. See how we represent buyers in Naples.
A Santa Rosa at Olde Cypress specialist matters because the facts that decide a Monteverde Way purchase live in documents and two data systems rather than a listing feed: a street filed under two MLS names, four sales in four years, a club membership by covenant, fees nobody publishes, and three FEMA letters on one street.
Searching one MLS development name, pricing from a portal estimate, quoting a club figure from a website, reading the preliminary flood map as effective, or treating Fairway Preserve as part of the gated community. Each costs a buyer money or a surprise after closing. Our Santa Rosa at Olde Cypress neighborhood guide sets Santa Rosa beside the other all-golf neighborhoods.
Jesse McGreevy and Marc Comisar, Top 1% Real Estate Agents Nationally Since 2008, are the local real estate experts who represent Santa Rosa at Olde Cypress buyers: licensed Florida REALTORS with Domain Realty who run every search and negotiation themselves, with Marc in the field and Jesse on the data and documents.
Marc Comisar is a licensed Florida REALTOR and Broker Associate with Domain Realty. He tours with you, runs the gate logistics and negotiates your offer: (239) 287-5873, Marc Comisar agent page.
Jesse McGreevy is a licensed Florida REALTOR and Sales Associate with Domain Realty and a co-founder of the brokerage. He runs the comparables and the association, club and flood documents: (239) 898-6072, Jesse McGreevy agent page.
See Sell Your Home in Santa Rosa at Olde Cypress for how we price, market and close on Monteverde Way, or how we sell homes across Olde Cypress. Call Jesse direct at (239) 898-6072. Buying first? Read how we represent buyers in Naples or call Marc at (239) 287-5873.
These are the questions buyers ask before they write an offer in Santa Rosa at Olde Cypress, answered from the public record for a Collier County purchase: the street, the sales, the club, costs, flood, rules and schools. Nothing here is legal, tax or insurance advice.
On Monteverde Way, a street off Olde Cypress Drive in the middle of the gated Olde Cypress community in North Naples, ZIP 34119, reached through the single gate on Treeline Drive at Logan Boulevard North.
27 single-family homes on the 2026 preliminary Collier County roll, 26 on Monteverde Way and one on Olde Cypress Drive.
None were active or pending on September 26, 2026. The nearest listings were two Terramar homes at $1,825,000 and $1,669,900.
Two MLS closings in the twelve months to September 26, 2026: $1,512,500 and $1,600,000, both on Monteverde Way in December 2025, a small sample.
Four MLS closings from September 27, 2022 to September 26, 2026, at $1,825,000, $1,229,000, $1,512,500 and $1,600,000.
None of the four closings reached its final list price; buyers paid from 92.48 to 98.46 percent of list, $25,000 to $125,000 below.
Collier County records 44 qualified Santa Rosa sales since 2001, at an all-history median of $742,500, and ten in the last decade from $675,000 to $1,825,000.
Yes. All 27 lots sit within 10 feet of the golf course parcel on the county's parcel map.
The four MLS sales ran 2,551 to 4,044 square feet of living area. Lots run 8,602 to 16,006 square feet, median 9,907.
The 2026 preliminary roll dates them 2000 to 2007, median 2005, built in two waves, with fourteen homes appearing by 2006.
Social membership in The Club at Olde Cypress is, automatically, under Section 14.02 of the recorded 2019 declaration. Golf membership is optional.
The club does not publish them, and third-party figures conflict widely, from roughly $45,000 to $175,000 for golf initiation. Get current figures in writing from the membership office at (239) 596-4797.
Non-equity and privately owned by a Stock family entity; owners hold no equity, vote or ownership interest in the club.
The Santa Rosa association bills quarterly, including the master share, and publishes the amount only on its resident portal. The estoppel certificate states it.
The master association may collect a working capital contribution at transfer under Section 8.13, amount not published; the estoppel states what applies and the contract says who pays.
No, confirmed by the county's CDD layer, the state's dissolved-district list and a 2025 tax bill.
The 2026 preliminary median for current owners is $7,692 at the 2025 rate of 9.5058 mills plus garbage; a buyer's bill resets to the new value and is usually higher.
On the effective 2012 map, 12 footprints sit wholly in Zone AH, 11 partly and 4 in Zone X; on the March 2025 preliminary map all 27 are in Zone X, not yet effective.
Only if your lender's determination puts the building in the Special Flood Hazard Area, but many owners buy it anyway; the ZIP 34119 median is $1,259 a year.
Three Monteverde Way homes hold Letters of Map Amendment issued in 2017, 2018 and 2022 removing the structure from the flood hazard area.
Collier County Evacuation Zone E, in Florida's Category 4 storm surge zone, about 6.7 miles inland.
Yes, with a 60-day minimum, no more than four leases a year, a $100 fee, a $1,000 deposit and Board approval; read the Santa Rosa restatement for any added rule.
No. Vehicles may not be parked on Olde Cypress streets overnight, and no more than two cars in a driveway.
Yes, common household pets, leashed outdoors; livestock, poultry and reptiles are prohibited.
Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026 to 2027, all rated A in 2024, 2025 and 2026.
No. Fairway Preserve is a condominium outside the gate, with its own association and no club membership.
Yes, since August 17, 2024, and the compensation in it is negotiable.
Usually 30 to 60 days from contract to closing, depending on jumbo financing and the association and club documents.
Santa Rosa for a shorter golf street and later build year; Terramar for more choice and a lower entry price.
In Collier County the buyer customarily pays the owner's title policy and chooses the closing agent; the contract controls.
Call Marc Comisar at (239) 287-5873 for a buyer consultation, or set up a saved search on our site filtered to Monteverde Way.
These are the questions owners ask when a sale and a Santa Rosa at Olde Cypress purchase have to happen together, answered for a Florida buyer and seller. They cover timing, contingencies, homestead portability and moving within the gate. Confirm anything that affects your contract with your closing agent or attorney.
With no Santa Rosa home listed and one or two sales a year, being able to move the day one lists is the advantage; selling first, or lining up bridge financing, usually wins the house.
You can, and a Santa Rosa seller may accept one, but a clean offer still wins when two buyers want the same home.
Often yes, within statutory limits, by filing with the new homestead application; the timing around January 1 matters.
Social membership follows the deed under the same covenant; ask the club how it treats any golf category you hold.
Start with a street-level valuation on our Santa Rosa at Olde Cypress home valuation page, or call Jesse direct at (239) 898-6072. Buying first? Read how we represent buyers in Naples or call Marc at (239) 287-5873.
Every Santa Rosa at Olde Cypress figure on this page traces to a primary source below, listed as of September 2026: the Southwest Florida MLS, the Collier County Property Appraiser roll and recorded sales (cited in plain text), the recorded declarations, the club's own pages, Florida Statutes, Freddie Mac, NAR and FEMA. No listing portal or competing brokerage is cited.
Market data and county records
The associations and their recorded documents
The Club at Olde Cypress
Florida statutes, rules and buyer representation
Flood, storm and insurance
Schools and location
Our related pages
Every row links the authority that publishes the document, so a Santa Rosa at Olde Cypress buyer sees the official, current 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, articles and bylaws, OR 4722 PG 375 | The neighborhood layer of rules, the association's powers and its assessments | Olde Cypress Master Association, PDF |
| 2019 Amended and Restated Declaration for Olde Cypress, OR 5700 PG 1118 | Mandatory social membership (Section 14.02), no club equity (14.03), the working capital contribution at transfer (8.13), leasing, pets, lakes and parking | Olde Cypress Master Association, certified PDF |
| 2013 leasing amendment, OR 4874 PG 3783 | The 60-day minimum, four leases a year, the $100 fee and the $1,000 deposit | 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 at the gate | Olde Cypress Master Association, PDF |
| Collier County 2026 flood protection newsletter | The CRS Class 5 discount and floodplain rules | Collier County, PDF |
| Florida Statutes 720.401 | The pre-contract disclosure summary and the buyer's cancellation right | Florida Senate |
| Florida Statutes 720.30851 | Estoppel certificate contents, delivery and fee caps | Florida Legislature |
| Florida Statutes 689.302 | The residential flood disclosure the seller owes you | Florida Legislature |
| FEMA Map Service Center | The flood zone and any letter for your own address | FEMA |
Documents that matter to a Santa Rosa purchase but are not public: the club's current social dues and golf initiation and dues, from the membership office at (239) 596-4797; the Santa Rosa budget and quarterly assessment, from the association's manager or resident portal; the master working capital contribution amount; and the estoppel certificates for the home.
Start your Santa Rosa at Olde Cypress home search with the Top 1% Real Estate Agents Nationally Since 2008 through a buyer consultation, the contact form on this page or a call to Marc Comisar at (239) 287-5873. With no Santa Rosa home listed on September 26, 2026 and two sales in the last year, the buyer who is ready when a Monteverde Way home appears is the buyer who gets it.
Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com. Read about the partnership on our about McGreevy and Comisar page. Nothing on this page is legal, tax or insurance advice.
Market data from Southwest Florida MLS, pulled September 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.
