Updated September 2026
What is a Santa Rosa at Olde Cypress home worth? Four Monteverde Way MLS sales since 2022, $1,229,000 to $1,825,000, 44 county deeds since 2001 and no home for sale today. Sell or buy with McGreevy and Comisar.
Updated September 2026 · By Jesse McGreevy and Marc Comisar, Domain Realty
A Santa Rosa at Olde Cypress home in Naples is worth what its own four MLS sales since 2022 and the county deed record support, adjusted for size, fairway position and condition. The two most recent Monteverde Way closings, in December 2025, sold for $1,512,500 and $1,600,000, and no Santa Rosa home was for sale on September 26, 2026.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
This page is the valuation companion to our Santa Rosa at Olde Cypress neighborhood guide, which sits under our Olde Cypress community guide. Santa Rosa at Olde Cypress is 27 detached golf-course homes, 26 on Monteverde Way and one on Olde Cypress Drive, behind the single staffed gate at Treeline Drive off Logan Boulevard North in North Naples, FL 34119. When you want the number for your own address, request a written valuation from McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008, or Call Jesse direct at (239) 898-6072.
This page covers the Santa Rosa neighborhood inside the gated Olde Cypress community in Naples, not Santa Rosa County in the Florida Panhandle, not Santa Rosa Beach in Walton County, and not any other Florida subdivision that shares the name. Fairway Preserve at Olde Cypress, the 264-unit condominium off Immokalee Road, carries the Olde Cypress name but sits outside the gate and is not part of the community.
Four Santa Rosa homes closed through the Southwest Florida MLS in the 48 months to September 26, 2026. Four is a small sample, so every sale is listed rather than turned into a headline median.
| MLS close date | Street | Bedrooms 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, closed September 27, 2022 to September 26, 2026, pulled September 26, 2026, with each sale assigned to Santa Rosa by street address against the 2026 preliminary Collier County roll. The Collier County Property Appraiser recorded qualified sales file, dated August 29, 2026, carries a matching deed for each of the four.
The 48-month MLS median for Santa Rosa is $1,556,250 on four sales (small sample, the mean of the middle pair, $1,512,500 and $1,600,000). That number describes none of the four homes. With 27 homes and about one resale a year, one closing can move a Santa Rosa median by six figures, so your value starts with the sale most like your house, not with the average of four unlike ones.
McGreevy and Comisar value Santa Rosa at Olde Cypress homes from the public record, sale by sale, and put the evidence in front of you rather than a single number. 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 write every valuation themselves.
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. If you are comparing agents before you ask anyone for a number, our guide to the best real estate agents in Naples compares the teams on the public record.
In the last 12 months Santa Rosa has seen two resales. Every sale described here is a public-record sale from the Southwest Florida MLS or the Collier County deed record, labelled as one.
Jesse McGreevy writes the analysis: the comparable set, the adjustments, the Terramar cross-check and the range. Marc Comisar walks the house when you want an in-person opinion, because on a 27-home street the lanai view, the roof and the finish level are what move a price away from the last sale. Reach Jesse at (239) 898-6072 or Marc at (239) 287-5873.
The Santa Rosa at Olde Cypress neighborhood guide holds the whole record on the street: the association, the build history, the flood file and the schools. Our guide to selling a home in Santa Rosa at Olde Cypress covers pricing strategy, marketing, disclosure and closing costs. And if your next home is also behind the Treeline Drive gate, how we help buyers purchase in Santa Rosa at Olde Cypress covers the other side of the table. This page is the number.
Santa Rosa at Olde Cypress home values rest on a thin but consistent record: four MLS closings in 48 months, all on Monteverde Way, all golf-course homes, and two in December 2025 at $1,512,500 and $1,600,000. The key facts below carry their window and source so a Naples owner can check each one.
Santa Rosa at Olde Cypress homes sold for $1,229,000 to $1,825,000 across four Southwest Florida MLS closings in the 48 months to September 26, 2026, and for $1,512,500 and $1,600,000 in the latest twelve months. The county recorded the same two sales in November 2025, its only Santa Rosa deeds in the twelve months to August 29, 2026.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
We tracked every one of the four Santa Rosa closings in the Southwest Florida MLS since September 2022 and read each one beside the county's deed record. No MLS window reaches ten Santa Rosa closings, even the widest 48-month pull, so this section lists every sale and uses the county's recorded sales since 2001 as the long view.
| MLS window to September 26, 2026 | Santa Rosa closings | Median sold (small sample) | Median $ per living sq ft | Median sold to list | Median days on market |
|---|---|---|---|---|---|
| 12 months | 2 | $1,556,250 (mean of $1,512,500 and $1,600,000) | $572.50 | 97.25% | 20.5 |
| 24 months | 2 | $1,556,250 (same two sales) | $572.50 | 97.25% | 20.5 |
| 36 months | 3 | $1,512,500 (observed middle sale) | $552.10 | 96.03% | 21 |
| 48 months | 4 | $1,556,250 (mean of $1,512,500 and $1,600,000) | $501.70 | 94.81% | 27.5 |
Every median is a median of per-sale figures, and every window is a small sample. Total 48-month MLS volume was $6,166,500.
This is a public-record sale from the Southwest Florida MLS, not a McGreevy and Comisar transaction. On December 4, 2025 a 2,898 square foot Monteverde Way home with four bedrooms, a den, four full baths and a half bath closed at $1,600,000 against a final list price of $1,625,000, after 34 days on market. That is 98.46 percent of list, the closest to asking of any Santa Rosa sale in four years, and $552.10 per square foot of living area. The county's deed file carries a $1,600,000 Monteverde Way sale recorded in November 2025, the same transaction on the public record. For a valuation it says three things. First, a well-presented Santa Rosa home priced near the recent evidence drew a buyer inside five weeks at a discount of $25,000. Second, $1,600,000 is now the top of the four-year MLS record for a Santa Rosa home under 3,000 square feet. Third, the buyer paid it without a competing Santa Rosa listing to compare against, which is the position the next Monteverde Way seller will also hold.
Two days apart in December 2025, two Santa Rosa homes closed. The 2,551 square foot home, three bedrooms plus a den, sold at $1,512,500 after 7 days, $592.90 per square foot and 96.03 percent of its $1,575,000 list. The 2,898 square foot home sold at $1,600,000 after 34 days, $552.10 per square foot. The larger home brought $87,500 more for 347 more square feet, about $252 per added foot, less than half the per-foot rate of either sale. That is the normal shape of a golf-community market: the lot, the view and the base house carry most of the price, and added square footage is worth less per foot than the average. Pricing a Santa Rosa home by multiplying its square feet by a neighborhood average overprices the large homes and underprices the small ones.
The February 2023 sale, the largest home in the record at 4,044 square feet of living area with four bedrooms, a den, five full baths and a half bath, closed at $1,825,000, 93.59 percent of a $1,950,000 list, after 34 days, or $451.29 per square foot. The April 2024 sale, 2,946 square feet with three bedrooms and a den, closed at $1,229,000, 92.48 percent of a $1,329,000 list, after 21 days, or $417.18 per square foot. Both gave up $100,000 or more from their final list. The two 2025 sales gave up $62,500 and $25,000 and sold for $135 to $176 more per square foot than the 2024 sale. The per-foot record rose between 2024 and late 2025 on this street even as the wider Olde Cypress median eased, which is why an older Santa Rosa comparable needs an adjustment measured on Santa Rosa's own sales.
On September 26, 2026 the Southwest Florida MLS showed no active and no pending Santa Rosa listing. Across all of Olde Cypress there were five actives and one pending or contingent listing, about 2.3 months of supply against 26 closings in twelve months. A Santa Rosa seller who lists next competes with Terramar and the rest of the gate, not with a neighbor on Monteverde Way. Few homes here come up for sale in a year, so the next owner who sells should call us first: request a Santa Rosa valuation or Call Jesse direct at (239) 898-6072. If you are buying instead, read how we represent buyers in Naples or Call Marc at (239) 287-5873.
A Santa Rosa at Olde Cypress home is valued in nine steps: confirm the plat and association, match living area and plan, read the fairway position, place the build era, weigh the lot, assemble the flood file, price the buyer's carrying costs, adjust for time, and borrow comparables from Terramar and the gate.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Santa Rosa at Olde Cypress is its own recorded plat with its own neighborhood association, Santa Rosa at Olde Cypress Homeowners' Association, Inc., filed with the state on April 9, 2001, under the Olde Cypress Master Property Owners Association. Twenty-six homes sit on Monteverde Way and one on Olde Cypress Drive, and the Southwest Florida MLS carries a separate Santa Rosa at Olde Cypress development name alongside Olde Cypress, so our pull covers both and assigns each sale by street against the county roll. We place your home in the recorded plat first, because that decides which sales are true comparables and which association's estoppel certificate your buyer will read.
The four MLS sales run from 2,551 to 4,044 square feet of living area and from three bedrooms plus a den to four bedrooms plus a den. Size moves price more than any other single fact, but not in a straight line, as the December 2025 pair shows. We compare your home with the Santa Rosa sale nearest in living area and bedroom count, then adjust using the roughly $252 per added square foot the December pair implies, not the $500 to $600 average.
Santa Rosa at Olde Cypress has 27 homes, every one on the golf course, and no home listed for sale on September 26, 2026, so the next Monteverde Way seller sets the price the whole street is measured by. Enter your address in the valuation form at the top of this page, request a Santa Rosa at Olde Cypress home valuation, or Call Jesse direct at (239) 898-6072. Buying in Santa Rosa instead? See how we help buyers purchase in Santa Rosa at Olde Cypress or Call Marc at (239) 287-5873.
Every one of the 27 Santa Rosa homes backs onto the golf course parcel on the county map, so the question is not whether you have a golf view but which one. A long fairway view, a green, a tee box, a lake inside the course or a view across to another neighborhood each read differently to a buyer. No public feed records which one you own; a walk to your lanai does.
Santa Rosa was built in two pulses. The county's building footprint layers show nine homes by 2002 and two more by 2004, then sixteen in the 2006 to 2009 layers; the 2026 preliminary roll puts the earliest year built at 2000 and the latest at 2007, with a median of 2005. A home from the first pulse may predate the 2002 Florida Building Code, and that shows up in the buyer's insurance quote. Roof age, impact openings, air conditioning, kitchens and baths are where condition turns into price.
County parcel polygons put Santa Rosa lots from 8,602 to 16,006 square feet, with a median of 9,907, close to Terramar's 10,479 median and well below Da Vinci Estates' 18,263. On a street where every lot faces the course, a larger lot with room for a pool or lanai extension is the rare premium.
On the effective May 16, 2012 FEMA map, 12 Santa Rosa footprints sit wholly in Zone AH, 11 partly and 4 wholly in Zone X, with nearby base flood elevation lines at 12.0 to 12.5 feet NAVD88. On the preliminary map FEMA issued March 20, 2025, all 27 fall in Zone X. Three Monteverde Way homes hold FEMA letters of map amendment issued between 2017 and 2022 that removed the structure from the flood zone. A home with an elevation certificate and a letter on file is easier to insure and finance, and that is value.
Your buyer inherits a mandatory club social membership, a quarterly neighborhood invoice with the master share and a tax bill that resets after the sale, and none of the dollar amounts is published. The costs section below shows how to remove that discount.
The county's Santa Rosa record moved from a single $675,000 sale in December 2020 to $1,210,000 in November 2021, $1,825,000 in February 2023, $1,229,000 in April 2024 and $1,512,500 and $1,600,000 in November 2025. Size explains much of that spread. A 2023 or 2024 sale is not a 2026 comparable without an adjustment, and we measure that adjustment from Santa Rosa's own per-foot record and the Olde Cypress trend, never a countywide index.
Four sales are not enough on their own, so we test the Santa Rosa number against Terramar at Olde Cypress, the rival street with eleven MLS closings in 48 months and two active listings, and against the Olde Cypress community median, before we give you a range.
The Collier County deed record holds 44 qualified Santa Rosa at Olde Cypress sales since 2001, at an all-history median of $742,500 (the mean of $735,000 and $750,000). Calendar-year medians ran from $560,350 in 2005 to $1,825,000 on the single 2023 sale, and the ten-year record of ten sales has a $1,030,000 median.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
The county file counts qualified, improved sales over $100,000, the deeds the state treats as arm's-length. It carries no living area, days on market or list price, so it is the long view of Santa Rosa prices, not a substitute for the MLS detail above. The newest recording in the file community-wide is May 22, 2026.
| Calendar year | County recorded Santa Rosa sales | County median |
|---|---|---|
| 2001 | 3 | $600,000 |
| 2002 | 2 | $637,500 |
| 2004 | 4 | $797,000 |
| 2005 | 6 | $560,350 |
| 2006 | 2 | $993,500 |
| 2009 | 1 | $815,000 (one sale) |
| 2010 | 4 | $651,000 |
| 2012 | 2 | $692,500 |
| 2013 | 3 | $735,000 |
| 2014 | 1 | $690,000 (one sale) |
| 2015 | 4 | $795,000 |
| 2016 | 2 | $730,000 |
| 2018 | 2 | $725,000 |
| 2020 | 1 | $675,000 (one sale) |
| 2021 | 3 | $850,000 |
| 2023 | 1 | $1,825,000 (one sale) |
| 2024 | 1 | $1,229,000 (one sale) |
| 2025 | 2 | $1,556,250 (mean of $1,512,500 and $1,600,000) |
Source: Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026. Years with no qualified Santa Rosa sale (2003, 2007, 2008, 2011, 2017, 2019, 2022 and 2026 through the file date) are omitted. Every year is a small sample, and a single sale is shown as that sale.
The county file carries ten qualified Santa Rosa sales in the 120 months to August 29, 2026, all on Monteverde Way, newest first:
Over 60 months the county shows five sales at a $1,512,500 median, with a range of $1,210,000 to $1,825,000; over 36 months, three at the same $1,512,500 median; over 120 months, ten at a $1,030,000 median (the mean of $850,000 and $1,210,000). All are small samples.
Santa Rosa prices held in a band of roughly $560,000 to $1,000,000 for twenty years, then stepped up through 2021. The last sale under $1,000,000 recorded in April 2021 at $800,000; every Santa Rosa deed since November 2021 has recorded at $1,210,000 or more. That step is the single most important fact for an owner who bought before 2021: the buyer's appraiser will read the post-2021 sales, not the purchase price. For an owner who bought in 2023, it is the reverse: the February 2023 sale was the largest home on the street, and a smaller home is not worth its price. Owners can request a Santa Rosa at Olde Cypress valuation or Call Jesse direct at (239) 898-6072; buyers can read how we help buyers purchase in Santa Rosa or Call Marc at (239) 287-5873.
The 2026 preliminary Collier County roll puts the median Santa Rosa just value at $1,079,324, with a range of $909,013 to $1,886,017, and the median total tax bill at $7,692. The two November 2025 sales recorded at $1,512,500 and $1,600,000, 40 to 48 percent above that median just value. That gap is normal in Florida, where just value is a tax figure that lags the market. Eighteen of the 27 Santa Rosa homes carry a homestead exemption on the 2026 preliminary roll, and seven owners list a mailing address in another state. Neither figure is a price.
Price per square foot tells a Santa Rosa at Olde Cypress owner where the street sits against the rest of the gate: the two twelve-month Santa Rosa closings sold at $552.10 and $592.90 per square foot of MLS living area, against a $472.75 median for all 26 Olde Cypress closings. It does not price a single home on its own.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
The MLS reports living area, the air-conditioned space a listing agent enters. The county roll reports building base area, which can include garages and covered areas. The median Santa Rosa county footprint is 4,383 square feet, far above any MLS living area on the street. Every per-foot figure on this page is sold price over MLS living area, and we never divide a county price by a county area or compare the two.
| Neighborhood | 48-month MLS closings | 48-month MLS median | Median $ per sq ft, MLS living area | Median sold to list | Sale range |
|---|---|---|---|---|---|
| Da Vinci Estates | 17 | $2,150,000 | $568.97 | 96.33% | $1,330,000 to $2,990,000 |
| Wild Orchid Court (Unit Two) | 6 | $1,929,111 | $584.01 | 96.22% | $1,775,000 to $2,800,000 |
| Strada Bella | 1 | One sale, $1,775,000 | $489.39 | 100% | One sale |
| Treeline and Olde Cypress Drive (Units One and Two, Biscayne Place) | 16 | $1,695,000 | $502.78 | 93.00% | $1,225,000 to $2,350,000 |
| Santa Rosa | 4 | $1,556,250 | $501.70 | 94.81% | $1,229,000 to $1,825,000 |
| Terramar | 11 | $1,400,000 | $446.14 | 93.65% | $850,000 to $1,900,000 |
| Lantana | 28 | $1,335,000 | $531.60 | 97.57% | $859,000 to $1,795,000 |
| Egret Cove | 2 | Two sales, $1,025,000 and $1,200,000 | $375.08 | 98.00% | Two sales |
| Lone Pine (Unit Three) | 9 | $1,000,000 | $436.49 | 94.10% | $775,000 to $1,110,000 |
| Santorini Villas | 13 | $645,000 | $335.69 | 98.36% | $600,000 to $800,000 |
Source: Southwest Florida MLS Matrix, closed September 27, 2022 to September 26, 2026, each sale assigned to a neighborhood by street. Biscayne Place recorded no MLS sale in the window and is counted with the Treeline and Olde Cypress Drive row. Every row under ten sales is a small sample; even-count medians are the mean of the middle pair.
Over 48 months Santa Rosa's median of $501.70 per square foot ran about $56 above Terramar's $446.14, on homes of similar lot size and the same all-golf position. Part of that is timing: half of Santa Rosa's four sales came in late 2025, while Terramar's eleven spread across four years. Part is the homes: the 2026 preliminary roll puts Terramar's median year built at 2003 against Santa Rosa's 2005. A valuation keeps both explanations in view rather than claiming a fixed premium.
Use the per-foot range, $417.18 to $592.90 across the four Santa Rosa sales, as a check on a value, not a method. A home near 2,500 square feet in current condition reads against the December 2025 sale at $592.90; a home near 4,000 square feet reads against the 2023 sale at $451.29 and the size curve, not against the smaller home's per-foot rate. When your per-foot result lands outside the Santa Rosa range, the value needs a reason, such as a remodel, a pool or a rare lot, that a buyer can see. For a per-foot check on your own home, request a written Santa Rosa valuation or Call Jesse direct at (239) 898-6072. Buyers: read how we represent buyers in Naples or Call Marc at (239) 287-5873.
Santa Rosa at Olde Cypress homes took 7 to 34 days on market across four MLS closings in 48 months, a median of 27.5 days, and closed at a median 94.81 percent of the final list price. The two twelve-month sales came in at 96.03 and 98.46 percent, near the 97.52 percent Olde Cypress community median.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Sold-to-list here is sold price over the final list price. None of the four Santa Rosa sales reached list. The two that gave up the most, 92.48 and 93.59 percent in 2024 and 2023, were the two where the list price sat furthest above what the street's evidence supported at the time. The two December 2025 sales gave up $62,500 and $25,000.
| Measure, twelve months to September 26, 2026 | Santa Rosa at Olde Cypress | All of Olde Cypress |
|---|---|---|
| MLS closings | 2 (small sample) | 26 |
| Median sold | $1,556,250 (mean of $1,512,500 and $1,600,000) | $1,105,000 (mean of $1,100,000 and $1,110,000) |
| Median $ per sq ft, MLS living area | $572.50 | $472.75 |
| Median sold to final list | 97.25% | 97.52% |
| Median days on market | 20.5 | 29 (n=24) |
| Active and pending on September 26, 2026 | None | 5 active, 1 pending or contingent |
| County recorded sales, twelve months to August 29, 2026 | 2, median $1,556,250 | 24, median $1,142,500 |
Source: Southwest Florida MLS Matrix, pulled September 26, 2026; Collier County Property Appraiser recorded qualified sales, data file dated August 29, 2026. Two sales are a small sample.
With no Santa Rosa home on the market and about 2.3 months of supply across Olde Cypress, the next Santa Rosa listing is the only choice on its street. That is an advantage, but not room to list well above the evidence: the 2023 and 2024 sellers who did gave up $100,000 or more. List at the evidence for your size, view and condition, and the first three weeks of showings, when the most motivated buyers see a new Santa Rosa listing, do the work. Sellers can read our guide to selling a home in Santa Rosa at Olde Cypress or Call Jesse direct at (239) 898-6072; buyers can Call Marc at (239) 287-5873 or read how we represent buyers in Naples.
A Santa Rosa at Olde Cypress buyer will very likely also tour Terramar at Olde Cypress, the other all-golf neighborhood off Olde Cypress Drive, with 55 homes on similar lots. Over 48 months Santa Rosa sold at a $1,556,250 MLS median on four sales at $501.70 per foot; Terramar at $1,400,000 on eleven at $446.14.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
| Factor | Santa Rosa at Olde Cypress | Terramar at Olde Cypress |
|---|---|---|
| Homes on the 2026 preliminary roll | 27 detached | 55 detached |
| Streets | Monteverde Way (26), Olde Cypress Drive (1) | Terramar Drive (43), Terramar Court (12) |
| Golf-course lots | 27 of 27 | 55 of 55 |
| Median lot, county parcel polygons | 9,907 sq ft | 10,479 sq ft |
| Median year built, 2026 preliminary roll | 2005 | 2003 |
| MLS closings, 48 months | 4 (small sample) | 11 |
| MLS median sold, 48 months | $1,556,250 | $1,400,000 |
| Median $ per sq ft, MLS living area, 48 months | $501.70 | $446.14 |
| Median sold to list, 48 months | 94.81% | 93.65% |
| Median days on market, 48 months | 27.5 | 20 |
| MLS closings and median, 12 months | 2, $1,556,250 | 3, $1,099,000 |
| Active on September 26, 2026 | None | 2, at $1,825,000 and $1,669,900 |
| County recorded sales, 36 months | 3, median $1,512,500 | 8, median $1,137,000 |
| Median 2026 preliminary just value | $1,079,324 | $965,006 |
| Median tax bill, 2026 preliminary roll | $7,692 | $7,334 |
| Effective 2012 FEMA map, footprints wholly in Zone AH | 12 of 27 | 7 of 55 |
| Preliminary March 2025 FEMA map | All 27 in Zone X | Zone X across the original PUD |
| Club social membership | Mandatory with the deed, golf optional | Mandatory with the deed, golf optional |
| CDD | None | None |
Sources: Southwest Florida MLS Matrix, closed September 27, 2022 to September 26, 2026 and active on the pull date; Collier County Property Appraiser 2026 preliminary roll and recorded qualified sales, data file dated August 29, 2026; FEMA National Flood Hazard Layer effective and preliminary panels.
Terramar's larger record is the best check on a Santa Rosa number. Its eleven sales in 48 months ran from $850,000 to $1,900,000, and its per-foot median of $446.14 sits below Santa Rosa's $501.70. When a Santa Rosa value lands well above the nearest Terramar sale of the same size and view, the reason has to be visible in the house: a later build, a remodel, a better fairway.
On September 26, 2026 Terramar had two active listings, at $1,825,000 with 2,816 square feet of living area after 133 days, and at $1,669,900 with 3,255 square feet after 17 days. Santa Rosa had none. A Santa Rosa home listed this season is measured against those two first. Pricing near the recent Santa Rosa evidence while Terramar's longer-listed home sits at a higher per-foot ask is how a Santa Rosa seller draws the buyer who is choosing between the two streets.
The buyer who chooses Santa Rosa wants a smaller street, 27 homes on one road, and a slightly later build era. The buyer who chooses Terramar gets more to choose from and, on the recent record, a lower price per foot. For a Santa Rosa seller, scarcity is real but is no license to price above what Terramar's same-size sales and the December 2025 pair support. To see how that plays into a listing plan, read our guide to selling a home in Santa Rosa at Olde Cypress or Call Jesse direct at (239) 898-6072; buyers comparing the two streets can read how we help buyers purchase in Santa Rosa at Olde Cypress or Call Marc at (239) 287-5873.
Online estimates miss on Santa Rosa at Olde Cypress homes because a model has four MLS sales in four years to learn from, cannot see which fairway a lanai faces, cannot read the three FEMA letters on Monteverde Way, and often blends Santa Rosa with nine neighborhoods whose Olde Cypress prices run from about $600,000 to $3 million.
An automated estimate needs a steady flow of nearby, similar sales. Santa Rosa gives it two in the latest year and four in forty-eight months, with living areas from 2,551 to 4,044 square feet. A model fills the gap by reaching across the gate, to Lone Pine Lane at a $1,000,000 median or Da Vinci Estates at $2,150,000, and the estimate for a Monteverde Way home swings with whichever neighbor it borrows.
A model that reads the effective 2012 FEMA map sees 12 Santa Rosa footprints wholly in Zone AH; one that reads the March 2025 preliminary map sees all 27 in Zone X. Neither reads the three FEMA letters that removed Monteverde Way structures from the flood zone. A buyer's insurer and lender read all three layers, and so does the price.
Treat it as a question, not an answer. Ask which sales it used, whether they were on Monteverde Way, and whether they shared your size, build era and view. When the answer is no, the estimate is not about your home. A written valuation from the four Santa Rosa sales, the county record and the Terramar cross-check is. Request a Santa Rosa at Olde Cypress home valuation or Call Jesse direct at (239) 898-6072; buyers can Call Marc at (239) 287-5873 or read how we represent buyers in Naples.
A Santa Rosa at Olde Cypress buyer prices in the quarterly neighborhood invoice with its master association share, mandatory club social dues, any golf they add, a property tax bill that resets after purchase, flood insurance if the lender requires it, and a wind premium set by your roof and openings. No association or club amount is published.
Social membership in The Club at Olde Cypress is mandatory with every home under Section 14.02 of the 2019 Amended and Restated Declaration for Olde Cypress, and golf membership is optional. The club is privately owned and non-equity. It does not publish initiation or dues on its site, and third-party figures circulating online conflict widely, from roughly $45,000 to $175,000 for golf initiation, and are not club-published. The current figures come from the club's membership office, and a buyer who cannot price the club discounts the house, so we get the written figures first.
A Santa Rosa owner belongs to the Santa Rosa at Olde Cypress Homeowners' Association and, through it, to the Olde Cypress Master Property Owners Association. The master association's About page says owners receive a quarterly invoice from their neighborhood association that includes the neighborhood's costs plus the owner's share of the master association, and that the fee includes basic exterior landscaping. The dollar amounts sit on the resident portal, not in public. The estoppel certificate under Florida Statutes 720.30851 states the figure, along with any master working capital contribution due at transfer under Section 8.13 of the master declaration, whose amount we did not locate in public documents.
The median Santa Rosa tax bill on the 2026 preliminary Collier County roll is $7,692. Across the Olde Cypress PUD the median homesteaded home pays $6,361 and the median non-homesteaded home $9,176, at the 2025 rate of 9.5058 mills. A buyer does not inherit your Save Our Homes cap, so the buyer's first full bill on a $1,500,000 purchase is usually higher than yours, and a careful buyer adjusts the offer for it.
Whether a lender requires flood insurance is decided per building from the effective map, which still shows most Santa Rosa footprints touching Zone AH, unless the home holds a FEMA letter. The wind premium follows the roof, the openings and the wind mitigation form. A Santa Rosa home from the 2000 to 2002 pulse without documented upgrades meets a higher quote than a 2006 home with impact openings, and the buyer counts the difference.
There is no Community Development District on Olde Cypress tax bills, and the club states it has no member assessments and no food and beverage minimum on its About Us page. The clubhouse renovation reported at $16 million was funded by the owner without a member assessment. Those are costs a Santa Rosa buyer does not have to price, and your listing should say so with the sources. Sellers: request a Santa Rosa valuation or Call Jesse direct at (239) 898-6072. Buyers pricing the carrying cost: Call Marc at (239) 287-5873 or read how we help buyers purchase in Santa Rosa.
A Santa Rosa at Olde Cypress seller owes the buyer the Florida Statutes 720.401 homeowners association disclosure summary before the contract is signed, because the Santa Rosa association and the Olde Cypress master association are both Chapter 720 associations. The seller also owes the flood disclosure, the property tax disclosure summary and known material facts.
Florida Statutes 720.401 requires that a prospective parcel owner "be presented a disclosure summary before executing the contract for sale," supplied on a resale by the parcel owner. The contract must carry the statutory voidability language in conspicuous type, and if the summary is missing the buyer may cancel "within 3 days after receipt of the disclosure summary or prior to closing, whichever occurs first." That right cannot be waived. It is a pre-contract duty, never a closing-table item.
Santa Rosa's original declaration is recorded at OR 3057 PG 2810, restated in 2006 at OR 4144 PG 425 and again in 2011 at OR 4722 PG 375, published by the master association as the 2011 Amended Declaration, Articles and Bylaws for Santa Rosa. The master declaration's leasing rule, no lease under 60 days and no more than four leasehold interests per parcel per calendar year, applies too. We did not find either declaration restating the 720.401 duty, so we do not claim it does. The seller owes the summary before contract; the working capital contribution under Section 8.13 is collected at transfer in a Board-set amount the estoppel states. This is information, not legal advice.
The flood disclosure under Florida Statutes 689.302 and the property tax disclosure summary under Florida Statutes 689.261 go with every residential sale. On Monteverde Way, pair them with any FEMA letter for your address and an elevation certificate if you have one, and the buyer's lender has what it needs on day one.
Selling a Santa Rosa at Olde Cypress home in Collier County costs the seller the deed documentary stamp tax at $0.70 per $100, the negotiated brokerage commission, the estoppel certificate fee, a municipal lien search and the property tax proration. In Collier County the buyer customarily pays the owner's title policy and chooses the closing agent, and the contract controls.
Florida's documentary stamp tax on the deed is $0.70 per $100 of price under Florida Statutes 201.02, customarily paid by the seller. At $1,556,250, the Santa Rosa twelve-month median, that is $10,893.75. At $1,600,000, the latest Santa Rosa sale, it is $11,200.
In Collier County the buyer customarily pays the owner's title insurance policy and chooses the closing agent, the reverse of the Lee County custom. The contract controls, and the parties can allocate any line item, but a Santa Rosa seller should not budget the owner's policy as a seller cost unless the contract says so. The premium itself is promulgated by the state under Florida Administrative Code Rule 69O-186.003.
The estoppel certificate for a current account is capped at $299 under Florida Statutes 720.30851 as amended in 2024, with statutory add-ons for rush delivery or a delinquent account. A municipal lien search customarily falls to the seller. Property taxes are paid in arrears, so the seller credits the buyer for the days owned: on the median $7,692 Santa Rosa bill, a June 30 closing credits roughly $3,814, before the early-payment discount the title company applies.
Since August 17, 2024 commissions are explicitly negotiable, offers of buyer-broker compensation cannot appear in the MLS, and buyers sign a written agreement with their own agent before touring, per the National Association of REALTORS settlement FAQs. A Santa Rosa seller may still offer to contribute toward the buyer's agent off the MLS. We put the commission conversation in writing at the first meeting. For a net estimate on your home, request a Santa Rosa valuation or Call Jesse direct at (239) 898-6072; buyers can Call Marc at (239) 287-5873 or read how we represent buyers in Naples.
Four things move a Santa Rosa at Olde Cypress value before listing: the roof and openings documented for insurance, a flood file assembled for a street with no elevation certificates in the county's file, the club and fee figures in writing, and timing against the January to May season. Each one removes a buyer discount or widens the buyer pool.
Nine Santa Rosa homes appear in the county's 2000 or 2002 footprint layers, so some may predate the 2002 Florida Building Code, and every Santa Rosa home is now 19 to 26 years old by its roll year built. A buyer's insurer will ask for a four-point inspection and price the roof and openings from a wind mitigation form. Collier County's building code wind layers put the design wind speed for ordinary homes here at 160 mph. Documented upgrades are value; undocumented ones are a question the buyer prices.
Collier County's elevation certificate file holds 65 certificates for Olde Cypress streets, and none of them is on Monteverde Way. Three Santa Rosa homes hold FEMA letters removing the structure from the flood zone, one issued in 2017 with a lowest adjacent grade of 14.6 feet NAVD88, one in 2018, and one in 2022 at 13.8 feet, against base flood elevation lines of 12.0 to 12.5 feet nearby. A Santa Rosa seller who orders an elevation certificate before listing gives the buyer's lender a document almost no neighbor can, and may qualify the home for its own letter.
Sixty-three of 107 Olde Cypress MLS closings over four years landed from January through May. Santa Rosa's own recent deeds recorded in November, April and February, and the two latest MLS closings in early December. A home that goes live in October or November meets the season's first buyers as they arrive; one listed in April is racing the end of it.
A free in-person Santa Rosa at Olde Cypress valuation starts with the address form on this page or a call to Jesse McGreevy at (239) 898-6072. Marc walks the house, Jesse writes the analysis as one half of the Top 1% Real Estate Agents Nationally Since 2008, and you receive a written range built from the Santa Rosa record.
Every Santa Rosa MLS and county sale with dates and sources, a per-foot check that never mixes county and MLS square feet, the Terramar and Olde Cypress competition with price histories, your buyer's club, fee and tax picture, your flood file with any FEMA letter for your address, and a recommended list price with a defensible range. There is no obligation to list.
Use the valuation form on this page or our Santa Rosa at Olde Cypress home valuation request, or Call Jesse direct at (239) 898-6072. The office of McGreevy and Comisar is at 24031 S Tamiami Trl #101, Bonita Springs, FL 34134. For how the valuation turns into a listing, read our guide to selling a home in Santa Rosa at Olde Cypress. Buying next? Read how we help buyers purchase in Santa Rosa at Olde Cypress or Call Marc at (239) 287-5873.
Our Olde Cypress home valuation compares all nine neighborhoods behind the gate, and our Terramar at Olde Cypress home valuation works through the rival street's larger record. The Santa Rosa at Olde Cypress neighborhood guide holds the association, schools and drive-time detail.
McGreevy and Comisar are a top-reviewed listing team on Google, and the quotes below are genuine five-star client reviews that any Santa Rosa at Olde Cypress owner can check on that profile, reproduced in each reviewer's own words. We publish no aggregate score and no star-rating widget. Read them all 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
★★★★★ "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
Jesse McGreevy and Marc Comisar, Top 1% Real Estate Agents Nationally Since 2008, are the local real estate experts behind every McGreevy and Comisar valuation in Santa Rosa at Olde Cypress, licensed Florida REALTORS with Domain Realty who have run the team together since 2008, with Jesse on the analysis and Marc on the house.
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. He runs pricing, data, marketing and the association paperwork. Reach him at (239) 898-6072 and on the Jesse McGreevy agent page.
Marc Comisar is a licensed Florida REALTOR and Broker Associate with Domain Realty and the other half of McGreevy and Comisar. He walks the house for in-person valuations and runs the field side of every listing. Reach him at (239) 287-5873 and on the Marc Comisar agent page.
Jesse McGreevy: (239) 898-6072, [email protected]. Marc Comisar: (239) 287-5873. Office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134. Read about the partnership on our about McGreevy and Comisar page.
These are the questions Santa Rosa at Olde Cypress owners ask when they want to know what a Monteverde Way home is worth in Naples, answered from the public record in one paragraph each. They cover value, comparables, the club, fees, taxes, flood and selling costs. Nothing here is an appraisal, or legal or tax advice.
Your home is worth what the four Santa Rosa MLS sales since 2022 support once adjusted for your size, view, build era and condition. The two latest closed at $1,512,500 and $1,600,000 in December 2025. Request a Santa Rosa valuation for your address.
Two Santa Rosa homes closed through the Southwest Florida MLS in the twelve months to September 26, 2026: a 2,551 square foot home at $1,512,500 and a 2,898 square foot home at $1,600,000, both on Monteverde Way.
No MLS window, even 48 months, holds ten Santa Rosa closings. A median of two or four sales is not a market, so we list each sale with its size, list price, days on market and sold-to-list, and use the county's 44 recorded sales since 2001 for the long view.
The four Santa Rosa MLS sales in 48 months ran from $417.18 to $592.90 per square foot of living area, a small-sample median of $501.70. The two twelve-month sales were $552.10 and $592.90, against $472.75 for all of Olde Cypress.
The four Santa Rosa MLS sales took 7, 21, 34 and 34 days on market, a small-sample median of 27.5 days. The Olde Cypress community median over twelve months was 29 days.
Between 92.48 and 98.46 percent of the final list price across four sales, a median of 94.81 percent. None reached list. The two December 2025 sales came in at 96.03 and 98.46 percent.
None. On September 26, 2026 the Southwest Florida MLS showed no active and no pending Santa Rosa listing. Across all of Olde Cypress there were five actives and one pending or contingent listing.
Twenty-seven detached single-family homes on the 2026 preliminary Collier County roll, 26 on Monteverde Way and one on Olde Cypress Drive, all backing onto the golf course parcel.
No. It is a 27-home neighborhood inside the gated Olde Cypress community in North Naples, Collier County, FL 34119, off Logan Boulevard North. Santa Rosa County and Santa Rosa Beach are in the Florida Panhandle.
Over 48 months Santa Rosa sold at a $1,556,250 MLS median on four sales and $501.70 per foot; Terramar at $1,400,000 on eleven sales and $446.14. Terramar's per-foot median is lower on a larger record.
The Santa Rosa record does not show it. The two November 2025 deeds, $1,512,500 and $1,600,000, sold at higher per-foot rates than the 2023 and 2024 sales, even as the Olde Cypress calendar-year median eased from its 2023 peak.
The county recorded two Santa Rosa sales in 2016 at a $730,000 median and two in 2018 at $725,000. The ten-year record of ten sales has a $1,030,000 median, and every deed since November 2021 has recorded at $1,210,000 or more.
No. The median 2026 preliminary just value is $1,079,324, while the two November 2025 sales recorded at $1,512,500 and $1,600,000. Just value is a tax figure that lags the market.
Every Santa Rosa home backs onto the course, so the question is which view. A long fairway view, a green or a lake inside the course reads differently to a buyer than a view of a tee box or cart path, and we price it from the house, not the feed.
Yes, mostly through insurance and condition. Nine homes appear in the county's 2000 or 2002 footprint layers and sixteen in the 2006 to 2009 layers. Roof age, impact openings and systems move the buyer's insurance quote and the price.
They are not published. The Santa Rosa association sends a quarterly invoice that includes the Olde Cypress master association share and basic exterior landscaping. The amount is on the resident portal, and the estoppel certificate states it for a sale.
It affects what a buyer thinks it will cost to own. Social membership comes with the deed and golf is optional. The club publishes no dues or initiation, so we get the membership office's written figures before listing.
No. There is no Community Development District on Olde Cypress tax bills, and the club states it has no member assessments and no food and beverage minimum.
Usually higher. The median Santa Rosa bill on the 2026 preliminary roll is $7,692. A buyer does not inherit your Save Our Homes cap, so the bill resets toward the purchase price after the sale.
On the effective May 16, 2012 FEMA map, 12 Santa Rosa footprints sit wholly in Zone AH, 11 partly and 4 wholly in Zone X. On the preliminary March 20, 2025 map, all 27 fall in Zone X. The preliminary map is not effective yet.
Yes. Three Monteverde Way homes hold FEMA letters removing the structure from the flood zone. A letter, or an elevation certificate showing the floor well above the base flood elevation, answers the lender's flood question and can lower the buyer's cost.
It is worth considering. None of the 65 elevation certificates Collier County holds for Olde Cypress streets is on Monteverde Way, so a Santa Rosa seller with one gives a buyer's lender a document almost no neighbor can.
The Florida Statutes 720.401 disclosure summary, before the buyer signs, plus the flood disclosure and the property tax disclosure summary. Missing the 720.401 summary gives the buyer a cancellation right that runs until closing.
Your buyer should read the Santa Rosa and master declarations, and the estoppel certificate confirms the account and any transfer charges. Ask the association manager what approval or registration it requires before closing.
Section 8.13 of the master declaration provides a working capital contribution collected at the transfer of title in a Board-set amount. We did not locate the amount in public documents; the estoppel certificate states it, and the contract decides who pays.
The deed documentary stamp tax at $0.70 per $100, the negotiated commission, the estoppel fee capped at $299 for a current account, a municipal lien search and the tax proration. In Collier County the buyer customarily pays the owner's title policy; the contract controls.
At $0.70 per $100, a $1,512,500 sale carries $10,587.50 in deed stamps and a $1,600,000 sale $11,200, customarily paid by the seller.
Sixty-three of 107 Olde Cypress MLS closings over four years landed from January through May. Listing in October or November puts a Santa Rosa home in front of the season's first buyers.
You can, but the master leasing rule allows no lease under 60 days and no more than four leasehold interests per parcel per year, and a tenant limits showings. Most Santa Rosa buyers want to occupy, so a vacant, staged home usually shows better.
Yes. A written valuation from McGreevy and Comisar carries no obligation to list. Request one here or Call Jesse direct at (239) 898-6072.
Gather your roof date, openings, any FEMA letter or elevation certificate and your latest association invoice, then request a written valuation. Our guide to selling a home in Santa Rosa at Olde Cypress walks through the listing plan.
Every Santa Rosa at Olde Cypress value on this page traces to a primary source below, listed as of September 2026: the Southwest Florida MLS, the Collier County Property Appraiser roll and recorded sales (cited in plain text), the recorded declarations, the club's own pages, Florida Statutes and FEMA. No listing portal, automated estimate or competing brokerage is cited.
Market data and county records
The associations and their 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 owner always sees the official, current version rather than a copy. We host nothing ourselves, and the documents that are not public are named at the end with the office that holds each.
| Document | What it settles | Official authority |
|---|---|---|
| Santa Rosa 2011 amended declaration, articles and bylaws, OR 4722 PG 375 | The Santa Rosa association's covenants, maintenance and governance | Olde Cypress Master Association, PDF |
| 2019 Amended and Restated Declaration for Olde Cypress, OR 5700 PG 1118 | Mandatory social membership (Section 14.02), 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 and four leases a year | Olde Cypress Master Association, PDF |
| Olde Cypress neighborhood site map | Where Santa Rosa, the other eight neighborhoods, 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 |
| Florida Statutes 689.261 | The property tax disclosure summary a seller gives the buyer | Florida Legislature |
| Collier County 2026 flood protection newsletter | The county's flood insurance discount class and floodplain rules | Collier County, PDF |
| Collier County Building Bulletin 21 | Elevation certificate and lowest-floor 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 | Florida Legislature |
| Florida Statutes 201.02 | The $0.70 per $100 deed stamp | Florida Legislature |
| FEMA Map Service Center | The flood zone and any letter for your own address | FEMA |
Documents that matter to a Santa Rosa sale but are not public: the club's current social dues and golf initiation and dues, from the club's membership office; the Santa Rosa association's budget and quarterly invoice, from the resident portal or the manager; the master working capital contribution amount; and the estoppel certificate for your home.
You reach the Santa Rosa at Olde Cypress valuation team through the form on this page, our Santa Rosa at Olde Cypress home valuation request, or a call to Jesse McGreevy at (239) 898-6072. About one Santa Rosa home sells in a typical year, so the next seller should call the Top 1% Real Estate Agents Nationally Since 2008 first.
Jesse McGreevy: (239) 898-6072, [email protected]. Marc Comisar: (239) 287-5873. Office: 24031 S Tamiami Trl #101, Bonita Springs, FL 34134.
Jesse McGreevy (Sales Associate, 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; read about the partnership on our about McGreevy and Comisar page. Nothing here 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.
