Units One, Two and Three at Olde Cypress is the largest neighborhood behind the Olde Cypress gate in Naples: 185 detached homes on Olde Cypress Drive, Treeline Drive, Wild Orchid Court and Lone Pine Lane. Sell or buy with McGreevy and Comisar.
Units One, Two and Three at Olde Cypress is a single-family neighborhood inside the master-planned community of Olde Cypress in Naples, Florida. It is the largest of the nine neighborhoods behind the Treeline Drive gate: 185 detached homes on three recorded plats, governed by one association, the Olde Cypress Homeowners' Association, with Unit One on Olde Cypress Drive and Treeline Drive, Unit Two on Treeline Drive and Wild Orchid Court, and Unit Three on Lone Pine Lane. In the 24 months to September 26, 2026 the Southwest Florida MLS recorded 14 closings here at a $1,250,000 median. McGreevy and Comisar are the team Units One, Two and Three sellers should call first, and the team its buyers should call when they want the record behind a price. Jesse McGreevy and Marc Comisar lead Domain Realty Group, the #1 real estate team in Southwest Florida since 2012, and have been Top 1% Real Estate Agents Nationally Since 2008.
A word on the names, because they confuse buyers and search engines alike. "Unit One", "Unit Two" and "Unit Three" are the names of recorded plats of single-family lots, not condominium units. Biscayne Place, eight estate homes that share Treeline Drive and Olde Cypress Drive addresses at the entrance, is a separate association with its own declaration and is not part of this neighborhood. Fairway Preserve at Olde Cypress, the 264-unit condominium off Immokalee Road, sits outside the gate and is not part of the community at all, and Olde Cypress in Naples is not Cypress Woods, Cypress Trace or Winding Cypress. Everything below comes from recorded, state, county, FEMA, club and MLS records, cited as we go; where the record stops, we name the document that would answer the question.
If you own in Units One, Two and Three and are weighing a sale, start with the market snapshot, the three unit sections and the seller section, then call Jesse. If you are buying, the plat-by-plat detail below will tell you which of three quite different price bands fits you before you tour.
By Jesse McGreevy and Marc Comisar, McGreevy and Comisar, Domain Realty Group. Updated September 2026.
McGreevy and Comisar are the best realtor for Units One, Two and Three at Olde Cypress because the case sits on the record: the #1 team in Southwest Florida since 2012, Top 1% of agents nationally since 2008, over $900 million in personal sales, and a market read built from all 31 MLS closings in 48 months, the county roll and the recorded declarations.
If you're searching for the best realtor for Units One, Two and Three at Olde Cypress in Olde Cypress, Naples, whether you're ready to sell your Units One, Two and Three at Olde Cypress home or buy your next one, McGreevy and Comisar is the team that delivers. We lead Domain Realty Group, the #1 real estate team in Southwest Florida since 2012, Top 1% Nationally since 2008, with over $2.5 billion sold as a team and $900 million in personal sales between Jesse and Marc.
Recent Units One, Two and Three at Olde Cypress track record (last 12 months): In the last 12 months Units One, Two and Three at Olde Cypress has seen 8 resales in the Southwest Florida MLS Matrix (pulled September 26, 2026, closings September 27, 2025 to September 26, 2026), at a median of $1,052,500 (n = 8, even, so the median is the mean of the middle pair, $1,005,000 and $1,100,000), a range of $775,000 to $1,275,000, $8,280,000 in total volume, a median of 49 days on market (n = 7; one sale was entered after closing and carries no marketing period) and a median sold-to-final-list ratio of 94.52% (n = 8). The highest-priced sale in that window was $1,275,000, a Treeline Drive home that closed in April 2026 after six days on market. Six of the eight were on Lone Pine Lane, which is why the 12-month median sits well below the 24-month figure. The Matrix pull does not identify listing or selling offices, so we state no represented-sale count here. Ask us and we will walk you through every one of the eight.
We tracked every one of the 31 Units One, Two and Three at Olde Cypress closings in the Southwest Florida MLS since September 2022, and all 86 county-recorded qualified sales in the last ten years, before writing a word of this guide; each MLS closing is listed in the market snapshot below.
For Units One, Two and Three sellers: premium marketing, including cinematic video, drone, professional photography, a qualified-buyer database, and discretion with off-market capability when a sale needs to stay quiet, built on the right comparable set for your street. We also build the paperwork file before the first showing: the estoppel, the Resale Assessment, the master working capital contribution, the club terms and the Chapter 720 disclosure summary.
For Units One, Two and Three buyers: the first question is the plat, which sets the lot, the view and the price band. The second is carrying cost: an unpublished quarterly invoice, the club's social dues, and 2026 preliminary tax medians from $5,754 in Unit Three to $10,252 in Unit Two. The third is flood: most homes touch Zone AH on the effective 2012 FEMA map, while the preliminary 2025 map places all 185 in Zone X. Sellers and buyers comparing the best real estate agents in Naples should ask each one to answer those three questions for a specific Units One, Two and Three address; we answer them below. For how the team was built, see about McGreevy and Comisar.
Honors and recognition:
Selling your Units One, Two and Three at Olde Cypress home? Get a free Units One, Two and Three at Olde Cypress home valuation or call Jesse direct at (239) 898-6072.
Buying a home in Units One, Two and Three at Olde Cypress? Call Marc at (239) 287-5873 for a personalized buyer consultation, start with our Units One, Two and Three at Olde Cypress buyer's guide, or read how we represent buyers in Southwest Florida.
Living in Units One, Two and Three at Olde Cypress means a detached home on a golf or preserve lot behind one staffed gate in North Naples, lawns and landscaping maintained by the association, mandatory social membership in The Club at Olde Cypress, optional golf, no CDD, and three distinct streetscapes under one set of covenants.
Units One, Two and Three at Olde Cypress is the neighborhood the Olde Cypress Homeowners' Association governs: 185 single-family homes on the 2026 preliminary Collier County roll, spread over three recorded plats. Unit One holds 61 homes, 42 on Olde Cypress Drive and 19 on Treeline Drive. Unit Two holds 69, 44 on Treeline Drive and 25 on Wild Orchid Court. Unit Three is Lone Pine Lane, 55 homes. The master association's site map colors all three as one neighborhood, "Olde Cypress HOA", roughly a third of the 548 homes inside the gate.
The three plats were recorded as separate subdivisions, but one declaration binds them. Exhibit A of the association's 2016 Amended and Restated Declaration (OR 5260 PG 3502) lists Olde Cypress Unit One at Plat Book 32, Page 1, Olde Cypress Unit Two at Plat Book 32, Page 66 and Olde Cypress Unit Three at Plat Book 32, Page 84. Every owner has one vote per lot and is also a member of the master association, which is why this guide covers all three together, with a section for each plat.
Treeline Drive and Olde Cypress Drive are where a buyer can be fooled. Both run through Unit One, Treeline Drive also runs through Unit Two, and eight homes at their corner just inside the gate belong instead to Biscayne Place at Olde Cypress, a separate association with its own 2004 declaration and larger estate lots. Wild Orchid Court is entirely Unit Two, and Lone Pine Lane is entirely Unit Three. Every figure in this guide uses the county roll's plat assignment, so Biscayne Place sales are not in our numbers. Before an offer on either street, confirm the plat on the deed.
The Olde Cypress entrance is a single staffed gatehouse on Treeline Drive, just east of Logan Boulevard North and about a quarter mile north of Immokalee Road. Treeline Drive runs from the gate through Units One and Two to Wild Orchid Court; Olde Cypress Drive branches off Treeline Drive through Unit One and feeds every other neighborhood street, Lone Pine Lane included. Unit Two's east side borders the master association's 158.59-acre preserve, and Lone Pine Lane backs onto that same preserve.
On the 2026 preliminary Collier County roll, 136 of the 185 homes (73.5%) carry a Florida homestead exemption, against about seven in ten across the Olde Cypress PUD, and only 29 owner mailing addresses are in another US state, 2 abroad. The homes here are mostly primary residences, so the buyer pool is local as well as seasonal.
The association's only common tracts on the county roll are its roads, so there is no neighborhood pool, clubhouse or tennis court; those are the club's, reached through the mandatory social membership. There are no condominiums, no attached villas, no age restriction and no boating or swimming on the lakes.
Units One, Two and Three at Olde Cypress homes closed at a $1,250,000 median over the 24 months to September 26, 2026 (n = 14, Southwest Florida MLS), at a median $451.39 per living square foot, 93.16% of final list price and 49 days on market. The window is 24 months because 12 months held only eight closings.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Measure (Southwest Florida MLS Matrix, closings September 27, 2024 to September 26, 2026) | Units One, Two and Three |
|---|---|
MLS closings | 14 |
Dollar volume | $18,978,000 |
Median sold price | $1,250,000 (n = 14, even: mean of $1,225,000 and $1,275,000) |
Price range | $775,000 to $2,600,000 |
Median sold price per living square foot | $451.39 (median of per-sale ratios, n = 14) |
Median sold-to-final-list ratio | 93.16% (median of per-sale ratios, n = 14) |
Median days on market | 49 (n = 13; one sale entered after closing has no marketing period) |
Closings at or above final list | 1 |
For context, across all of Olde Cypress in the 12 months to September 26, 2026 the MLS recorded 26 closings at a median of $1,105,000 (the mean of $1,100,000 and $1,110,000), a median $472.75 per living square foot, a median 97.52% of list and a median 29 days on market (n = 24). Units One, Two and Three has sold slower and further below list than the community as a whole.
MLS window to September 26, 2026 | Closings | Median sold price | Median $ per living sq ft | Median sold-to-list | Median days on market |
|---|---|---|---|---|---|
12 months | 8 (small sample) | $1,052,500 (mean of $1,005,000 and $1,100,000) | $420.92 | 94.52% | 49 (n = 7) |
24 months | 14 | $1,250,000 (mean of $1,225,000 and $1,275,000) | $451.39 | 93.16% | 49 (n = 13) |
36 months | 21 | $1,285,000 (observed sale) | $470.09 | 93.38% | 48.5 (n = 20) |
48 months | 31 | $1,450,000 (observed sale) | $475.59 | 94.00% | 45 (n = 30) |
Ratios are medians of per-sale ratios. The medians fall as the window shortens because the mix shifted toward Lone Pine Lane, the smallest homes, while 2023 included five sales above $1.9 million.
We list every sale because the sample is small and every comparable matters. Street names only; we never publish house numbers.
Closed | Street (plat) | Bedrooms / baths (half) | Living sq ft | Final list | Sold | $ per living sq ft | Sold-to-list | Days on market |
|---|---|---|---|---|---|---|---|---|
May 2026 | Lone Pine Lane (Unit Three) | 2 + den / 2 (1) | 2,097 | $850,000 | $850,000 | $405.34 | 100.00% | Entered after closing |
May 2026 | Lone Pine Lane (Unit Three) | 4 / 3 | 2,340 | $1,169,000 | $1,100,000 | $470.09 | 94.10% | 13 |
Apr 2026 | Treeline Drive | 3 + den / 3 | 2,904 | $1,300,000 | $1,275,000 | $439.05 | 98.08% | 6 |
Mar 2026 | Lone Pine Lane (Unit Three) | 2 + den / 2 (1) | 2,217 | $1,045,000 | $1,005,000 | $453.32 | 96.17% | 49 |
Feb 2026 | Lone Pine Lane (Unit Three) | 3 / 2 (1) | 2,543 | $1,199,000 | $1,110,000 | $436.49 | 92.58% | 76 |
Feb 2026 | Lone Pine Lane (Unit Three) | 3 + den / 3 | 2,320 | $990,000 | $940,000 | $405.17 | 94.95% | 42 |
Dec 2025 | Lone Pine Lane (Unit Three) | 3 + den / 3 | 2,407 | $829,900 | $775,000 | $321.98 | 93.38% | 293 |
Nov 2025 | Treeline Drive | 4 + den / 4 | 3,350 | $1,499,000 | $1,225,000 | $365.67 | 81.72% | 124 |
Aug 2025 | Wild Orchid Court (Unit Two) | 4 / 3 (1) | 3,237 | $3,000,000 | $2,600,000 | $803.21 | 86.67% | 19 |
Jul 2025 | Treeline Drive | 3 + den / 3 | 2,706 | $1,325,000 | $1,285,000 | $474.87 | 96.98% | 27 |
Jul 2025 | Olde Cypress Drive (Unit One) | 3 + den / 2 (1) | 2,786 | $1,850,000 | $1,715,000 | $615.58 | 92.70% | 20 |
Jun 2025 | Olde Cypress Drive (Unit One) | 3 + den / 4 | 3,580 | $2,150,000 | $1,998,000 | $558.10 | 92.93% | 101 |
Apr 2025 | Wild Orchid Court (Unit Two) | 4 + den / 5 | 3,738 | $2,025,000 | $1,775,000 | $474.85 | 87.65% | 58 |
Nov 2024 | Treeline Drive | 3 + den / 3 | 2,948 | $1,485,000 | $1,325,000 | $449.46 | 89.23% | 142 |
Jun 2024 | Wild Orchid Court (Unit Two) | 4 + den / 4 (1) | 4,338 | $2,950,000 | $2,800,000 | $645.46 | 94.92% | 70 |
Jun 2024 | Olde Cypress Drive (Unit One) | 3 + den / 3 | 2,949 | $1,595,000 | $1,450,000 | $491.69 | 90.91% | 48 |
Apr 2024 | Olde Cypress Drive (Unit One) | 3 + den / 3 | 3,032 | $1,495,000 | $1,438,000 | $474.27 | 96.19% | 66 |
Mar 2024 | Treeline Drive | 3 + den / 4 | 3,289 | $1,998,500 | $1,998,500 | $607.63 | 100.00% | 3 |
Feb 2024 | Lone Pine Lane (Unit Three) | 2 + den / 2 (1) | 2,217 | $1,100,000 | $1,025,000 | $462.34 | 93.18% | 106 |
Nov 2023 | Lone Pine Lane (Unit Three) | 4 / 3 | 2,340 | $999,999 | $925,000 | $395.30 | 92.50% | 20 |
Oct 2023 | Olde Cypress Drive (Unit One) | 3 + den / 3 (1) | 2,986 | $1,980,000 | $1,980,000 | $663.09 | 100.00% | 5 |
Aug 2023 | Treeline Drive | 3 + den / 3 (1) | 3,722 | $2,150,000 | $2,150,000 | $577.65 | 100.00% | 3 |
Aug 2023 | Wild Orchid Court (Unit Two) | 3 + den / 3 (1) | 3,240 | $1,711,230 | $1,876,180 | $579.07 | 109.64% | 940 |
Aug 2023 | Wild Orchid Court (Unit Two) | 3 + den / 3 (1) | 3,240 | $1,548,800 | $1,908,222 | $588.96 | 123.21% | 434 |
Aug 2023 | Olde Cypress Drive (Unit One) | 3 + den / 4 | 3,336 | $2,150,000 | $1,800,000 | $539.57 | 83.72% | 23 |
Aug 2023 | Olde Cypress Drive (Unit One) | 3 + den / 2 (1) | 2,786 | $1,499,999 | $1,325,000 | $475.59 | 88.33% | 11 |
May 2023 | Olde Cypress Drive (Unit One) | 3 + den / 3 | 3,956 | $2,500,000 | $2,350,000 | $594.03 | 94.00% | 3 |
May 2023 | Wild Orchid Court (Unit Two) | 3 + den / 3 (1) | 3,445 | $1,999,500 | $1,950,000 | $566.04 | 97.52% | 2 |
May 2023 | Lone Pine Lane (Unit Three) | 2 + den / 2 (1) | 2,097 | $999,000 | $1,000,000 | $476.87 | 100.10% | 4 |
Feb 2023 | Treeline Drive | 4 + den / 4 (1) | 4,078 | $1,799,900 | $1,675,000 | $410.74 | 93.06% | 64 |
Oct 2022 | Treeline Drive | 5 + den / 4 (1) | 4,437 | $2,579,900 | $2,280,000 | $513.86 | 88.38% | 98 |
Source: Southwest Florida MLS Matrix, pulled September 26, 2026, closings September 27, 2022 to September 26, 2026, each assigned to its plat by address against the Collier County Property Appraiser 2026 tax roll. Treeline Drive runs through both Unit One and Unit Two, so those rows carry the street only. Seven of the 31 closed at or above the final list price.
Two rows need a note. The two Wild Orchid Court homes of 3,240 square feet that closed the same day in August 2023, above their final list prices after 434 and 940 days on market, carry the pattern of homes sold before or during construction; county building footprints show two Unit Two homes first appearing in 2023, and neither sale appears in the county's qualified-sale list. And the $2,600,000 Wild Orchid Court sale of August 2025, at $803.21 per living square foot, is the highest price per square foot in the association's four-year record.
On September 26, 2026 the Southwest Florida MLS showed no active listing in Units One, Two and Three and one pending or contingent sale: a Treeline Drive home listed at $1,790,000 with four bedrooms plus a den, four baths and 3,350 square feet of living area, which went under contract after four days on market. Across all of Olde Cypress that day there were five active listings and this one pending sale.
With no active listing against eight closings in 12 months, Units One, Two and Three had effectively no standing inventory on September 26, 2026, against about 2.3 months of supply for Olde Cypress as a whole. That is a thin-supply signal, not a speed signal: the 12-month median marketing period was 49 days (n = 7), against 29 for the community (n = 24). Priced to its street, a home can go under contract in days; priced to an Olde Cypress average, it waits.
The Collier County Property Appraiser's recorded qualified sales are a second, independent record of arm's-length sales of improved homes over $100,000, data file dated August 29, 2026, with the newest Olde Cypress recording on May 22, 2026.
County window to August 29, 2026 | Qualified sales | Median recorded price | Range |
|---|---|---|---|
12 months | 8 (small sample) | $1,052,500 (mean of $1,005,000 and $1,100,000) | $775,000 to $1,275,000 |
24 months | 14 | $1,250,000 (mean of $1,225,000 and $1,275,000) | $775,000 to $2,600,000 |
36 months | 20 | $1,280,000 (mean of $1,275,000 and $1,285,000) | $775,000 to $2,600,000 |
60 months | 38 | $1,325,000 (mean of $1,325,000 and $1,325,000) | $775,000 to $3,100,000 |
120 months | 86 | $1,025,000 (mean of $1,025,000 and $1,025,000) | $415,000 to $3,100,000 |
All history since 1999 | 303 | $765,000 (observed sale) |
The 12-month and 24-month county results match the MLS exactly, which tells us the two records are counting the same sales. The highest recorded price in the association's county history is $3,100,000, a Wild Orchid Court sale recorded in August 2022.
The county's calendar-year medians trace the association's history: $159,900 on 18 sales in 2000, the first full year of lot and home sales; $1,180,000 on 13 in 2005; $570,000 on 21 in 2012; $1,025,000 on 7 in 2020; a peak of $1,737,500 on 8 in 2023; $1,715,000 on 7 in 2025; and $1,052,500 on 6 in 2026 to May 22. Every year after 2004 is a small sample, and the 2026 figure reflects five Lone Pine Lane recordings between February and May, not a fall in value on the other two plats.
Units One, Two and Three at Olde Cypress is the largest neighborhood inside Olde Cypress, and on September 26, 2026 it had no active listing and one pending sale, a Treeline Drive home that went under contract in four days at a $1,790,000 list price. In a neighborhood with no standing inventory, the seller who prices to the plat and the street, with the association paperwork already in the file, is the seller who sets the next comparable.
Selling a Units One, Two and Three at Olde Cypress home? Get a free Units One, Two and Three at Olde Cypress home valuation or call Jesse direct at (239) 898-6072.
Buying in Units One, Two and Three at Olde Cypress? Call Marc at (239) 287-5873, start with our Units One, Two and Three at Olde Cypress buyer's guide, or read how we represent buyers in Southwest Florida.
This is a public-record sale, not one of ours; we walk through it because it is the most recent Units One, Two and Three sale outside Lone Pine Lane and the one closest to full price. A Treeline Drive home with three bedrooms plus a den, three baths and 2,904 square feet of living area was listed at $1,300,000, went under contract after six days on market and closed on April 30, 2026 at $1,275,000, or 98.08% of list and $439.05 per living square foot. The county recorded it the same day at the same price.
Three things made it work. The list price sat just above the July 2025 Treeline Drive closing of a 2,706 square foot home at $1,285,000, so the price per square foot was below that comparable rather than above it. The home sold in the spring, inside the season, when the buyer pool is deepest. And the price left room under the $1,325,000 to $1,450,000 band that three of the four 2024 Olde Cypress Drive and Treeline Drive closings had set. Compare the November 2025 Treeline Drive sale: a larger 3,350 square foot home listed at $1,499,000 took 124 days and closed at $1,225,000, 81.72% of list.
Unit One at Olde Cypress is the master plat of the Olde Cypress Homeowners' Association: 61 detached homes, 42 on Olde Cypress Drive and 19 on Treeline Drive, with 60 of 61 lots on the golf course, a median lot of 14,257 square feet and a 60-month county median of $1,695,000 on 12 recorded sales.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Unit One was recorded at Plat Book 32, Page 1, and the association's declaration describes its homesites as Lots 1 through 12 of Tract 1, Lots 1 through 31 of Tract 4 and Lots 1 through 18 of Tract 10, which is exactly 61. The same plat carries the master association's tracts and the club parcels; Strada Bella at Olde Cypress, 18 estate homes with their own association, was built on another tract of the Unit One plat. Lots here run from 13,080 to 21,520 square feet, and at 14,257 square feet Unit One's median lot is the largest of the three plats.
Measure | Unit One |
|---|---|
Homes | 61 (42 Olde Cypress Drive, 19 Treeline Drive) |
Earliest building year on the roll | 2000 to 2006, median 2001 |
Median lot | 14,257 sq ft (0.32 acre); range 13,080 to 21,520 |
Golf-course lots | 60 of 61 |
Median 2026 preliminary just value | $1,294,566 ($869,265 to $1,629,566) |
Median 2026 preliminary total taxes | $8,438 |
Homestead exemption | 47 of 61 (77.0%) |
County qualified sales, 36 months | 6, median $1,847,500 (mean of $1,715,000 and $1,980,000), small sample |
County qualified sales, 60 months | 12, median $1,695,000 (mean of $1,675,000 and $1,715,000) |
MLS closings on Olde Cypress Drive, 48 months | 8, median $1,757,500 (mean of $1,715,000 and $1,800,000), small sample |
Sources: Collier County Property Appraiser, 2026 tax roll (preliminary) and parcel polygons; Collier County recorded qualified sales, data file dated August 29, 2026; Southwest Florida MLS Matrix, September 26, 2026. Just values are assessed values for tax purposes, not prices.
The eight Olde Cypress Drive closings in the MLS over 48 months ran from $1,325,000 to $2,350,000, for homes of 2,786 to 3,956 square feet of living area, all three bedrooms plus a den. The two most recent were a 2,786 square foot home at $1,715,000 in July 2025 and a 3,580 square foot home at $1,998,000 in June 2025. The county's 60-month record for the whole plat, 12 sales at a $1,695,000 median, is the steadiest price read for Unit One.
On the effective May 16, 2012 FEMA map, 11 Unit One footprints sit wholly in Zone AH, the shallow ponding zone, 20 partly, and 30 wholly in Zone X, with nearby base flood elevations of 12.0 to 13.0 feet NAVD88. Unit One has the lightest mapped Zone AH exposure of the three plats. On FEMA's preliminary map issued March 20, 2025, every Unit One footprint falls in Zone X; that map is not effective yet.
Unit Two at Olde Cypress holds 69 detached homes, 44 on Treeline Drive and 25 on Wild Orchid Court, with the highest median just value in the association at $1,453,941, the association's only homes built after 2010, and a Wild Orchid Court median of $1,929,111 on six MLS closings in 48 months, a small sample.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Unit Two was recorded at Plat Book 32, Page 66. Its lots run from 11,445 to 21,016 square feet with a median of 13,440. Fifty-five of the 69 lots back onto the golf course and 18 border the master association's preserve on the east side. Wild Orchid Court is a cul-de-sac off Treeline Drive; the "Wild Orchid at Woodsedge" label on some listing records is not a separate association.
Measure | Unit Two |
|---|---|
Homes | 69 (44 Treeline Drive, 25 Wild Orchid Court) |
Earliest building year on the roll | 2000 to 2023, median 2003; two in the 2010s and two in the 2020s |
Median lot | 13,440 sq ft (0.30 acre); range 11,445 to 21,016 |
Golf-course lots / preserve lots | 55 / 18 |
Median 2026 preliminary just value | $1,453,941 ($922,084 to $2,073,797) |
Median 2026 preliminary total taxes | $10,252 |
Homestead exemption | 52 of 69 (75.4%) |
County qualified sales, 36 months | 6, median $1,305,000 (mean of $1,285,000 and $1,325,000), high $2,600,000, small sample |
County qualified sales, 60 months | 15, median $1,775,000 |
Of which Treeline Drive, 60 months | 9, median $1,285,000, small sample |
Of which Wild Orchid Court, 60 months | 6, median $2,175,000 (mean of $1,950,000 and $2,400,000), small sample |
MLS closings on Wild Orchid Court, 48 months | 6, median $1,929,111 (mean of $1,908,222 and $1,950,000), small sample |
Sources: Collier County Property Appraiser, 2026 tax roll (preliminary); Collier County recorded qualified sales, August 29, 2026; Southwest Florida MLS Matrix, September 26, 2026.
Wild Orchid Court is where the association's highest prices sit. Its six MLS closings in 48 months ran from $1,775,000 to $2,800,000 for 3,237 to 4,338 square feet of living area, and the county's highest recorded sale in the whole association, $3,100,000, was a Wild Orchid Court home in August 2022. The Unit Two roll also shows the association's only recent construction: homes first appearing on county footprint layers in 2011, 2014, 2016, 2018 and two in 2023. The county data does not show whether each is a late first build or a rebuild; either way, a 2023 home and a 2003 home on the same street are built to different codes, and priced accordingly.
Treeline Drive is the association's through street. Its Unit Two homes recorded a $1,285,000 median over 60 months on nine county sales, against $2,175,000 on six for Wild Orchid Court, the clearest evidence in the record that position matters inside a single plat.
Unit Two has the heaviest mapped Zone AH exposure in the association on the effective 2012 map: 30 footprints wholly in Zone AH, 35 partly and 4 wholly in Zone X, with nearby base flood elevations of 12.5 to 13.5 feet NAVD88. FEMA has issued eight letters removing individual homes on Treeline Drive and Wild Orchid Court from the Special Flood Hazard Area since 2012, including LOMA 12-04-7997A, which recorded a lowest adjacent grade of 16.1 feet. An elevation certificate filed with a 2021 Wild Orchid Court permit records the top of the bottom floor at 16.60 feet NAVD88, 3.6 feet above that lot's 13-foot base flood elevation. On the preliminary March 2025 map, all 69 Unit Two footprints fall in Zone X.
Unit Three at Olde Cypress is Lone Pine Lane: 55 detached homes on the association's smallest lots, split between the golf course and the master preserve, and its most active street, with a $1,000,000 county median on 11 recorded sales over 60 months and six of the association's eight MLS closings in the last 12 months.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Unit Three was recorded at Plat Book 32, Page 84, and the association owns its 2.47-acre road tract. Lone Pine Lane is, with Egret Cove, one of the two most compact detached products inside Olde Cypress: lots of 7,534 to 19,852 square feet with a median of 9,785, and a median county footprint of 3,748 square feet (2,583 to 4,919), the smallest of the three plats. Twenty-six lots back onto the golf course and 33 onto the master association's large preserve.
Measure | Unit Three (Lone Pine Lane) |
|---|---|
Homes | 55 |
Build era | About 2000 to 2007 (first county footprint layers 2000 to 2007) |
Median lot | 9,785 sq ft; range 7,534 to 19,852 |
Golf-course lots / preserve lots | 26 / 33 |
Median 2026 preliminary just value | $783,010 |
Median 2026 preliminary total taxes | $5,754 |
County qualified sales, 36 months | 8, median $972,500 (mean of $940,000 and $1,005,000), small sample |
County qualified sales, 60 months | 11, median $1,000,000 (observed sale) |
MLS closings, 48 months | 9, median $1,000,000 (observed sale), small sample |
MLS closings, 12 months | 6, median $972,500 (mean of $940,000 and $1,005,000), median 49 days on market (n = 5), small sample |
Sources: Collier County Property Appraiser, 2026 tax roll (preliminary); Collier County recorded qualified sales, August 29, 2026; Southwest Florida MLS Matrix, September 26, 2026.
Lone Pine Lane carried the association's market in the last year. The county file records five Lone Pine Lane sales between February and May 2026, at $940,000, $1,110,000, $1,005,000, $1,100,000 and $850,000, after a $775,000 recording in December 2025. The spread inside one street is wide: the December 2025 sale took 293 days and closed at 93.38% of a $829,900 list, while a four-bedroom home closed in May 2026 at $1,100,000 after 13 days.
Thirty-three Lone Pine Lane lots face the master association's preserve rather than the course. Conservation lands inside Olde Cypress cannot be altered except to remove exotic plants under Section 11.04 of the 2019 Amended and Restated Declaration for Olde Cypress, so a preserve view is protected, but so is the buffer: a buyer planning a pool extension or new landscaping on a preserve lot should measure the conservation line on the survey before closing.
On the effective 2012 map, 29 Lone Pine Lane footprints are wholly in Zone AH, 14 partly and 12 wholly in Zone X, with nearby base flood elevations of 12.5 to 13.0 feet NAVD88. Six Lone Pine Lane homes hold FEMA letters removing the structure from the Special Flood Hazard Area, the first in 2012 and the most recent, LOMA 25-04-6753A, on September 29, 2025, with a lowest adjacent grade of 15.2 feet. On the preliminary March 2025 map, all 55 fall in Zone X.
Units One, Two and Three at Olde Cypress began in 1999: the Olde Cypress Homeowners' Association was incorporated on February 19, the Olde Cypress master declaration was recorded on April 27, and the association's original declaration followed on May 12, on land the Stock family partnership has owned since 1998, around the first P.B. Dye course in Collier County.
Olde Cypress Development, a Stock family partnership formed in September 1998, has owned the land and the course ever since. The Declaration of Covenants, Conditions, Restrictions and Easements for Olde Cypress, the master declaration, was recorded on April 27, 1999 at OR 2539 PG 2902, the same day the county renamed the Woodlands PUD as Olde Cypress. The Olde Cypress Homeowners' Association, Inc. was filed with the Florida Division of Corporations on February 19, 1999, per the Sunbiz record for the Olde Cypress Homeowners' Association, document number N99000001090, status active. The original Declaration of Covenants, Conditions, Restrictions and Easements for The Olde Cypress Single Family Community followed at OR 2546 PG 973, recorded May 12, 1999.
The course the three plats wrap around opened in 1999, an 18-hole, par 72 P.B. Dye design, reported by Golfweek as the first P.B. Dye course in Collier County. County footprint layers show 43 of Unit One's 61 homes in place by 2002 and the last by 2009; Unit Three filled by 2007; Unit Two was slower, with six homes appearing from 2011 to 2023.
The named homebuilders for the individual Unit One, Two and Three homes are not recorded in any public document we read. The declarant of record for the plats is the master declarant, Olde Cypress Development, and the builders would appear in the original plat dedications, the first deeds out of the developer and the county permit files. We name no builder we cannot document.
A 2010 county development summary, published in the April 26, 2011 Board of County Commissioners packet listed "Woodsedge" with 130 homes and "Ibis Landing" with 55, counts that match Units One and Two combined and Unit Three; both names survive in some listing records and neither is a separate association. The same amendment, adopted as Ordinance 2011-14, cut the PUD's approved cap from 1,100 homes to 942 and moved 158 units to what became Lantana.
The Sunbiz record shows an amendment filed on February 14, 2013. In 2016 the association recorded its current Amended and Restated Declaration at OR 5260 PG 3502, consolidating the earlier amendments under Chapter 720 of the Florida Statutes. The master association restated its own declaration in 2019 at OR 5700 PG 1118.
Units One, Two and Three at Olde Cypress homes are detached, mostly three bedrooms plus a den, from about 2,100 square feet of living area on Lone Pine Lane to about 4,400 on Treeline Drive and Wild Orchid Court, built mainly between 2000 and 2007 with a handful of Unit Two homes from 2011 to 2023.
Street (plat) | MLS closings, 48 months | Living area range | Bedrooms seen | Sold price range |
|---|---|---|---|---|
Lone Pine Lane (Unit Three) | 9 | 2,097 to 2,543 sq ft | 2 + den to 4 | $775,000 to $1,110,000 |
Olde Cypress Drive (Unit One) | 8 | 2,786 to 3,956 sq ft | 3 + den | $1,325,000 to $2,350,000 |
Treeline Drive (Units One and Two) | 8 | 2,706 to 4,437 sq ft | 3 + den to 5 + den | $1,225,000 to $2,280,000 |
Wild Orchid Court (Unit Two) | 6 | 3,237 to 4,338 sq ft | 3 + den to 4 + den | $1,775,000 to $2,800,000 |
Source: Southwest Florida MLS Matrix, pulled September 26, 2026, living area as reported in each listing. Living area excludes garages, lanais and covered entries; the county's building footprint includes them, which is why we never compare the two.
Twenty-seven of the 31 closings in 48 months were listed with a den or study on top of the bedroom count, and every Olde Cypress Drive closing was three bedrooms plus a den. That pattern, together with the lot sizes, is what separates Units One and Two from the villa product at Santorini Villas at Olde Cypress and from the newer, lake-oriented homes of Lantana at Olde Cypress, built 2013 to 2016.
The Florida Building Code took effect statewide on March 1, 2002, and 90 of the 185 homes (43 in Unit One, 21 in Unit Two, 26 in Unit Three) already appear in the county's 2000 or 2002 imagery, so many were permitted before it. A wind mitigation inspection documents the roof, openings and roof-to-wall connections insurers price; for a seller it is one of the cheapest documents to add to the listing file.
A home in Units One, Two and Three at Olde Cypress comes with association-maintained lawns and landscaping, private association roads, the master association's gate, preserve and lakes, and a mandatory social membership in The Club at Olde Cypress, whose tennis, pickleball, fitness, pool and dining sit outside the gate. Golf is a separate, optional purchase.
Section 7.1 of the association's 2016 restated declaration makes the association responsible for the common area and for "the maintenance of the lawns and landscaping (including irrigation equipment) located on Lots", except landscaping an owner installs without approval. The association is not responsible for landscaping replacement after a hurricane or other act of God. Section 7.2 leaves the owner the house, roof and exterior cleaning, and the driveway and sidewalk. No gravel or artificial turf may replace a lawn.
Section 14.02 of the master declaration makes every owner a social member of The Club at Olde Cypress "by acquisition of a Parcel." The club's membership page and About Us page describe what that brings: the clubhouse and its dining rooms, four clay tennis courts, two pickleball courts, three lighted bocce courts, a 4,000 square foot fitness center and the pool, with golf only as a golf member's guest. The club rebuilt its clubhouse in a $16 million renovation completed in April 2026, funded by the owner with no member assessment, and states it charges no assessments and no food and beverage minimum.
Full Golf and Associate Golf are sold separately, to residents and non-residents alike, and the club does not publish initiation fees or dues on its website. Third-party figures online conflict widely, from roughly $45,000 to $175,000 for golf initiation, and none is club-published, so we quote none. Members who use their own golf cart on the course pay an annual private cart fee of $1,950, per the club's own article. Ask the club's membership office at (239) 596-4797 for current terms in writing before you write an offer.
Every Units One, Two and Three home sits behind the single staffed gatehouse on Treeline Drive, guard house (239) 592-5381. The clubhouse sits west of the gate, and the master association's community access notice sets how guests and vendors are admitted.
HOA fees in Units One, Two and Three at Olde Cypress are billed as one quarterly invoice from the Olde Cypress Homeowners' Association that includes the master association's share. Neither association publishes the dollar amount outside its resident portal, so the reliable figure for a specific home is the estoppel certificate issued at contract.
The master association's About page explains the billing: owners receive quarterly invoices from their neighborhood association that include the neighborhood costs plus the owner's share of the master association, and the fee covers common grounds, streetlights, signage, paving and stormwater, plus basic exterior landscaping of each home. Section 4.1 of the association's 2016 restated declaration lists what an owner covenants to pay: the lot's share of annual assessments, special assessments, individual charges, the Resale Assessment and the lot's share of master association assessments. Section 4.9 makes the association the collector for the master association, and says plainly that the association "has no control over the amount or timing" of the master share.
We found no published budget or quarterly assessment amount for the association as of September 2026, and an HOA figure on a listing may omit the master share. The estoppel certificate under Section 720.30851 of the Florida Statutes settles it: the regular assessment, its frequency, any balance and any charge due at closing.
Section 4.4 of the declaration lets the association charge interest on a late assessment at the highest lawful rate, add a late fee of the greater of $25 or 5% of the installment, deny approval of a lease while an owner is delinquent, and foreclose its lien. Section 4.10 lets it collect rent directly from a tenant when an owner falls behind, under Section 720.3085(8) of the Florida Statutes.
Olde Cypress has no Community Development District. Collier County's CDD map lists none for the community, the state's dissolved districts list shows none, and the 2025 Collier County tax bill for a Lone Pine Lane home carries one non-ad valorem line, District 1 Garbage at $261.91, and no district assessment. Roads, stormwater and common areas are funded through the two associations instead.
Owning in Units One, Two and Three at Olde Cypress means four layers of cost: the association's quarterly invoice with the master share, the club's mandatory social dues, one-time charges when a home changes hands, and a Collier County tax bill at 9.5058 mills whose 2026 preliminary median runs from $5,754 to $10,252 by plat.
Layer | Amount | Who sets it | Source |
|---|---|---|---|
Association quarterly invoice, including the master share | Not published | Olde Cypress Homeowners' Association and the master association | Master association About page; estoppel certificate |
Club social membership dues | Mandatory; not published by the club | The Club at Olde Cypress | Master declaration Section 14.02; club membership page |
Club golf membership | Optional; initiation and dues not published | The Club at Olde Cypress | Club membership page |
Private golf cart fee | $1,950 a year, for members who use their own cart on the course | The Club at Olde Cypress | |
Resale Assessment, paid at closing | Set each calendar year by the association's Board; current amount not published | Olde Cypress Homeowners' Association | 2016 restated declaration, Section 4.8 |
Master working capital contribution at transfer | Board-set; current amount not located | Master association | 2019 restated master declaration, Section 8.13 |
Lease application and deposit (master) | $100 fee; $1,000 refundable deposit | Master association | |
Property taxes | 9.5058 mills in 2025; see medians by plat below | Collier County taxing authorities | 2025 Collier County Tax Collector bill; 2026 preliminary roll |
Flood insurance | Median $1,259 a year for single-family NFIP policies in ZIP 34119 | Insurer; required only where a lender requires it | OpenFEMA NFIP policies, as of September 8, 2026 |
Section 4.8 of the association's declaration creates a Resale Assessment "due and payable to the Association by the transferee" on a conveyance, in an amount the Board determines for each calendar year, collected at closing and usable for any common expense. It is the buyer's legal obligation under the declaration. Certain estate, estate-planning and foreclosure transfers are exempt. The current amount is not published; the estoppel certificate states it.
Plat (2026 preliminary Collier County roll) | Homes | Median 2026 preliminary total taxes | Median 2026 preliminary just value |
|---|---|---|---|
Unit One | 61 | $8,438 | $1,294,566 |
Unit Two | 69 | $10,252 | $1,453,941 |
Unit Three (Lone Pine Lane) | 55 | $5,754 | $783,010 |
All three | 185 | $7,532 | $1,195,234 |
A buyer does not inherit a seller's Save Our Homes cap. The year after you buy, the assessed value resets toward the just value, so budget on the current just value times the millage, not the seller's bill. Certified 2026 bills issue in November 2026.
On a home at the association's 24-month median of $1,250,000, Florida's documentary stamp tax on the deed, customarily a seller cost, is $8,750 at $0.70 per $100. In Collier County the buyer customarily pays for the owner's title insurance policy and chooses the closing agent, though the contract controls. The buyer also owes the Resale Assessment and, where the estoppel shows one, the master association's working capital contribution. Only the doc stamps can be quoted before the estoppel arrives.
Selling? Call Jesse direct at (239) 898-6072 and get a free Units One, Two and Three at Olde Cypress home valuation that nets out your closing costs. Buying? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.
The Olde Cypress Homeowners' Association's 2016 Amended and Restated Declaration, recorded at OR 5260 PG 3502, governs Units One, Two and Three at Olde Cypress on top of the 2019 master declaration. Where the two conflict, the master controls, but the neighborhood may enforce stricter rules, so a buyer needs both documents.
Section 2 of the neighborhood declaration makes every owner automatically a member of the master association and says the two sets of documents are cumulative. In a conflict the master documents are superior, but "the foregoing priorities shall not prevent enforcement by the Association of provisions of the Homeowners Association Documents that are stricter."
No improvement, a term Section 5.1 defines to include fences, walls, pools, additions, exterior painting, exterior lighting, gas tanks, screen enclosures and landscaping, may go ahead without the association's Architectural Review Committee, three to five members appointed by the Board for one-year terms. The committee has 45 days to act on a complete submission; an owner can appeal a denial to the Board, which decides within 20 days. Section 5.6 then requires the master association's construction committee approval as well, and the master criteria prevail where they conflict.
Section 9.11 prohibits dog runs, animal pens and fences or walls of any kind unless approved, and lets the committee adopt hurricane shutter standards covering color, style and how long shutters may stay closed. Section 9.16 requires an owner who will be away during hurricane season, June 1 to November 30, to clear movable objects from the lot before leaving and designate a person or firm to care for the home if it is damaged.
Under Section 9.6, cars and golf carts must be parked in the garage overnight. No more than two automobiles or minivans may sit in a driveway overnight without the master association's written consent, and only after every garage space is filled; overnight visitors display the gate pass on the dashboard. Commercial vehicles, trucks with lettering, vans, boats, trailers, campers and recreational vehicles may not be parked outside an enclosed garage, apart from temporary service and construction visits.
A lot may not be split or combined without Board approval and full zoning compliance, and assessments and votes stay with the original platted lots (Section 9.15). A home business must be invisible from outside and bring no visitors (Section 9.1). The declaration runs for 30 years from recording and then renews in 10-year periods unless 90% of the voting interests vote to end it (Section 13.1).
Units One, Two and Three at Olde Cypress is not a 55+ community. Neither the association's 2016 restated declaration nor the 2019 master declaration contains an age restriction or a housing-for-older-persons provision, so homes here may be bought, owned and occupied without regard to age, subject only to the ordinary occupancy, leasing and use rules.
Yes, homes in Units One, Two and Three at Olde Cypress can be leased, with limits: the whole home only, to a natural person, for a minimum of 60 consecutive days and no more than one year, no more than four leases a year, and only after both the association and the master association approve. Short-term vacation rental is not allowed.
Rule | Olde Cypress Homeowners' Association (Section 12 of the 2016 declaration) | Master association (Section 9.13 and the 2013 amendment) |
|---|---|---|
Minimum term | 60 consecutive days | 60 days |
Maximum term | 1 year; no renewal option unless the Board approves | Not stated |
Leases per year | Refers to the master limit | No more than four leasehold interests per parcel per calendar year |
What may be leased | The entire residence only | The whole parcel; no subleasing or room rentals |
Tenant | A natural person, not a company | Credit and background check |
Notice | Written notice at least 30 days before occupancy, with the signed lease | Board application |
Board decision | 30 days; silence counts as approval | 5 business days; silence counts as denial |
Fees | A preset processing fee within the legal maximum; none for a renewal with the same tenant | $100 application fee; $1,000 refundable common area deposit |
Timeshare | Prohibited | Counts as a lease |
Plan on two approvals running in parallel and on the stricter clock governing. Grounds for the association to disapprove include an owner who is behind on assessments, a history of unapproved leases or troublesome tenants, or false information on the application, and an unapproved lease is void and grounds for eviction. With a 60-day minimum and four leases a year, seasonal leasing works; vacation rental does not.
Pets are allowed in Units One, Two and Three at Olde Cypress: Section 9.5 of the association's declaration permits commonly accepted household pets such as dogs, cats and birds, not kept for commercial purposes, leashed or carried outside the home, and never left unattended on a lanai. Tenants and guests may keep pets too.
Every resale in Units One, Two and Three at Olde Cypress is a Chapter 720 homeowners' association sale, not a condominium sale. Section 720.401 of the Florida Statutes requires the seller to give the buyer the association disclosure summary before the contract is signed, and the estoppel certificate under Section 720.30851 settles what is owed at closing.
Section 720.401 makes the disclosure summary a pre-contract duty on a resale: it tells the buyer that membership in the association is mandatory, that assessments exist and can change, that the buyer may be obligated to pay special assessments, and that the covenants govern use of the property. If the summary is not provided before the contract is executed, the contract is voidable by the buyer, by written notice, within three days after receiving it or before closing, whichever comes first.
Under Section 720.30851 the association must deliver an estoppel certificate within 10 business days of a request, and the fee is capped by statute, at $299 for a current account as re-set in 2024. It is valid for 30 days, or 35 if delivered electronically. The declaration's older 15-day timeline yields to the statute. Because Units One, Two and Three owners pay the master share through the neighborhood invoice, confirm that the certificate states the master amounts as well.
There are no condominiums behind the Olde Cypress gate, so the Chapter 718 milestone inspection and structural integrity reserve study requirements do not apply to any Units One, Two and Three home. The roof and structure of each house are the owner's responsibility, so the buyer's inspection and wind mitigation report do the work a condominium document review would.
Units One, Two and Three at Olde Cypress sits in Collier County Evacuation Zone E and Florida's Category 4 storm surge zone, about 6.7 miles inland. On the effective 2012 FEMA map most of its 185 homes touch Zone AH; on FEMA's preliminary March 2025 map all 185 fall in Zone X, and 14 homes already hold FEMA letters of map amendment.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
The effective Flood Insurance Rate Map panels for Olde Cypress, 12021C0211H to 12021C0214H, took effect May 16, 2012 for unincorporated Collier County, NFIP community 120067, per the FEMA National Flood Hazard Layer. A new preliminary map was issued March 20, 2025, and Collier County opened the 90-day appeal period on August 19, 2026, with the new map targeted to take effect in summer 2027. Until then the 2012 map governs lender requirements.
Plat | Homes | Footprint wholly in Zone AH (2012 map) | Partly in Zone AH | Wholly in Zone X | Nearby base flood elevations | Preliminary 2025 map |
|---|---|---|---|---|---|---|
Unit One | 61 | 11 | 20 | 30 | 12.0 to 13.0 ft NAVD88 | All Zone X |
Unit Two | 69 | 30 | 35 | 4 | 12.5 to 13.5 ft NAVD88 | All Zone X |
Unit Three | 55 | 29 | 14 | 12 | 12.5 to 13.0 ft NAVD88 | All Zone X |
Method: county building footprints tested against the FEMA effective and preliminary flood hazard layers. Zone AH is FEMA's shallow ponding zone, one to three feet deep, with a set base flood elevation; Zone X is outside the 1% annual chance floodplain. A footprint that touches Zone AH does not mean the finished floor is below the base flood elevation.
FEMA has issued 14 letters removing individual Units One, Two and Three homes from the Special Flood Hazard Area since 2012: six on Lone Pine Lane and eight on Treeline Drive and Wild Orchid Court. Among them are LOMA 12-04-6596A on Lone Pine Lane with a lowest adjacent grade of 14.8 feet, LOMA 14-04-6330A and LOMA 20-04-0601A on Treeline Drive, LOMA 15-04-9175A on Wild Orchid Court and LOMA 22-04-4815A on Lone Pine Lane. The letters are address-specific; ask whether one exists before pricing flood insurance.
Every Olde Cypress home sits in Collier County Evacuation Zone E and in the Category 4 storm surge zone on the Florida Division of Emergency Management's Collier County surge map, outside the Coastal High Hazard Area and with no Zone VE. The county's building code wind layers put the ultimate design wind speed for houses at 160 miles per hour, inside the wind-borne debris region, so replacement windows and doors need impact-rated products or approved shutters.
All of ZIP 34119 has 124 NFIP flood claims on record since 1978, 88 of them from Hurricane Irma in 2017, per OpenFEMA's NFIP claims data; the census block group containing Olde Cypress shows three in total and no Hurricane Ian claim. We found no report naming Olde Cypress for storm damage, which is not proof of none, so ask for the seller's claims history.
Section 8.2 of the association's declaration makes each owner responsible for hazard and liability insurance on the lot, the home and personal property. After partial damage, the owner must remove debris within 60 days and finish repairs within one year; after total destruction, the owner may choose not to rebuild but must clear the lot. The association insures only the common area. Unincorporated Collier County is a CRS Class 5 community in the FEMA NFIP Community Status Book, worth a 25% flood premium discount inside the Special Flood Hazard Area and 10% outside it.
Selling and want your flood letters and elevation data in the file before buyers ask? Call Jesse direct at (239) 898-6072, or start with a free Units One, Two and Three at Olde Cypress home valuation. Buying and need a flood read on a specific address? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.
Every home in Units One, Two and Three at Olde Cypress, on Olde Cypress Drive, Treeline Drive, Wild Orchid Court and Lone Pine Lane, is assigned to Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026-2027 by the Collier County Public Schools address lookup, with no exceptions found on any of the four streets.
Street (plat) | Elementary | Middle | High |
|---|---|---|---|
Olde Cypress Drive (Unit One) | Laurel Oak | Oakridge | Aubrey Rogers |
Treeline Drive (Units One and Two) | Laurel Oak | Oakridge | Aubrey Rogers |
Wild Orchid Court (Unit Two) | Laurel Oak | Oakridge | Aubrey Rogers |
Lone Pine Lane (Unit Three) | Laurel Oak | Oakridge | Aubrey Rogers |
Source: Collier County Public Schools 2026-2027 address lookup, queried September 23, 2026 across every address record on each street. All three schools earned an A from the Florida Department of Education in 2024, 2025 and 2026, as republished by the Naples Daily News school grade database. Gulf Coast High is the assignment for the Fairway Preserve condominium outside the gate, not these streets.
County records for Units One, Two and Three at Olde Cypress show the neighborhood essentially built out by 2009, with six Unit Two homes first appearing on county footprint layers between 2011 and 2023, and 65 elevation certificates on file across Olde Cypress streets, including Wild Orchid Court, Treeline Drive and Lone Pine Lane.
The county's elevation certificate layer lists certificates on file for Wild Orchid Court (5), Treeline Drive (4, which may include Biscayne Place homes) and Lone Pine Lane (1), usually filed with a new build or a substantial permit. We did not pull each home's permit history; we pull it for a specific address before pricing a listing or writing an offer, because a permitted newer roof and impact glass change both value and insurance.
The biggest changes near Units One, Two and Three at Olde Cypress are roads and one unknown parcel: Collier County rates the Immokalee Road link in front of Olde Cypress as over capacity, FDOT plans a diverging diamond at I-75 Exit 111, and the fire district owns about 19 undeveloped acres immediately east of the community.
The North Collier Fire Control and Rescue District owns about 19 acres of agriculturally zoned land immediately east of Olde Cypress, the side where Unit Two and Lone Pine Lane back onto the master preserve. We found no public plan for it. Any change of use would need county approvals with public notice, and Lone Pine Lane and east Treeline Drive owners have the most reason to watch those notices.
Daily life in Units One, Two and Three at Olde Cypress runs through one gate on Treeline Drive at Logan Boulevard North, 1.6 road miles from I-75 Exit 111, with every car in a garage overnight, public open houses limited to weekend afternoons, and groceries, the beach and Mercato within about 15 minutes at free-flow speeds.
Guests and vendors are admitted at the Treeline Drive gatehouse under the master association's access procedures. Under the master association's Realtors Information page, public open houses run Saturday and Sunday, noon to 5 p.m., and broker opens Monday to Friday; outside those hours a buyer must come with an agent or owner, and open house signs come from the guard house against a $20 refundable deposit.
Destination | Road miles | Minutes, no traffic |
|---|---|---|
I-75 Exit 111 | 1.6 | About 3 |
Mercato | 7.3 | About 14 |
Delnor-Wiggins Pass State Park | 7.0 | About 14 |
Vanderbilt Beach | 8.2 | About 15 |
Naples Airport | 11.9 | About 18 |
Downtown Naples, Fifth Avenue South | 14.5 | About 23 |
Southwest Florida International Airport | 21.1 | About 27 |
Modeled with the OSRM routing engine on OpenStreetMap roads from the Treeline Drive and Logan Boulevard North intersection, September 2026. Homes at the north end of Olde Cypress Drive and on Lone Pine Lane add up to about 0.7 mile of community streets to the gate. In season, Immokalee Road runs slower; round up.
Units One, Two and Three at Olde Cypress sits in the upper middle of the nine Olde Cypress neighborhoods on price and far ahead of all of them on size: 185 of the 548 homes, 31 of the community's 107 MLS closings in 48 months, and a county median of $1,280,000 on 20 recorded sales over 36 months.
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 (2026 roll) | Product | Median lot | Median 2026 preliminary just value | MLS closings, 48 months, and median | County qualified sales, 36 months, and median |
|---|---|---|---|---|---|---|
Units One, Two and Three | 185 | Detached | 14,257 / 13,440 / 9,785 sq ft by plat | $1,195,234 | 31, $1,450,000 | 20, $1,280,000 |
Terramar | 55 | Detached | 10,479 sq ft | $965,006 | 11, $1,400,000 | 8, $1,137,000 (small sample) |
Santorini Villas | 55 | Attached paired villas | 6,639 sq ft | $558,186 | 13, $645,000 | 11, $640,000 |
Santa Rosa | 27 | Detached | 9,907 sq ft | $1,079,324 | 4, $1,556,250 (small sample) | 3, $1,512,500 (small sample) |
Egret Cove | 18 | Detached | 9,618 sq ft | $828,724 | 2, listed: $1,025,000 and $1,200,000 | 0 |
Strada Bella | 18 | Detached estate | 12,789 sq ft | $1,365,158 | 1, listed: $1,775,000 | 1, listed: $1,775,000 |
Biscayne Place | 8 | Detached estate | 16,680 sq ft | $1,704,810 | 0 | 0 |
Da Vinci Estates | 60 | Detached estate | 18,263 sq ft | $1,657,416 | 17, $2,150,000 | 12, $2,387,500 |
Lantana | 122 | Detached | 10,116 sq ft | $1,045,298 | 28, $1,335,000 | 17, $1,320,000 |
Sources: Collier County Property Appraiser, 2026 tax roll (homes, lots, just values); Southwest Florida MLS Matrix, pulled September 26, 2026, closings September 27, 2022 to September 26, 2026; Collier County recorded qualified sales, data file dated August 29, 2026. Samples under 10 are small; single sales are listed, not turned into medians.
Split by plat, the association spans most of the community's price range on its own. Wild Orchid Court's county median of $2,175,000 over 60 months sits near Da Vinci Estates at Olde Cypress, the community's top tier, while Lone Pine Lane's $1,000,000 sits beside Egret Cove at Olde Cypress and below Terramar at Olde Cypress. Unit One's 60-month county median of $1,695,000 sits above the small-sample $1,512,500 of Santa Rosa at Olde Cypress, on larger lots. For the community as a whole, see our Olde Cypress guide, how we sell homes across Olde Cypress and our Olde Cypress buyer's guide.
Selling? Call Jesse direct at (239) 898-6072 or get a free Units One, Two and Three at Olde Cypress home valuation. Buying? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.
Units One, Two and Three and Terramar at Olde Cypress are the two all-golf, detached neighborhoods most often weighed against each other in the $1 million to $1.5 million band. Terramar at Olde Cypress offers 55 golf-lot homes on two streets under one small association; Units One, Two and Three offers three plats, bigger lots on Units One and Two, and preserve lots on Lone Pine Lane.
Factor | Units One, Two and Three at Olde Cypress | Terramar at Olde Cypress |
|---|---|---|
Homes | 185 on three plats | 55 on one plat |
Streets | Olde Cypress Dr, Treeline Dr, Wild Orchid Ct, Lone Pine Ln | Terramar Dr, Terramar Ct |
Association | Olde Cypress Homeowners' Association (Sunbiz N99000001090, filed 1999) | Terramar at Olde Cypress Homeowners Association (Sunbiz N00000002851, filed 2000) |
Governing declaration | 2016 restatement, OR 5260 PG 3502 | Declaration OR 2689 PG 1846, recorded June 21, 2000 |
Build years (2026 roll) | 2000 to 2023; medians 2001 (Unit One) and 2003 (Unit Two) | 2000 to 2006, median 2003 |
Median lot | 14,257 / 13,440 / 9,785 sq ft by plat | 10,479 sq ft |
View | Golf 141 of 185; preserve on Lone Pine Ln and east Treeline Dr | Golf 55 of 55 |
Median 2026 preliminary just value | $1,195,234 | $965,006 |
Median 2026 preliminary taxes | $7,532 | $7,334 |
MLS closings, 48 months | 31, median $1,450,000, $475.59 per living sq ft, 94.00% of list, 45 days | 11, median $1,400,000, $446.14 per living sq ft, 93.65% of list, 20 days |
MLS closings, 24 months | 14, median $1,250,000 | 7, median $1,099,000 (small sample) |
County qualified sales, 36 months | 20, median $1,280,000 | 8, median $1,137,000 (small sample) |
Effective 2012 flood map, footprints wholly in Zone AH | 70 of 185 | 7 of 55, with 4 lots touching Zone AE |
Schools and club | Same schools; mandatory social membership, golf optional | Same |
Sources: Collier County Property Appraiser, 2026 tax roll; Southwest Florida MLS Matrix, September 26, 2026; Collier County recorded qualified sales, August 29, 2026; FEMA National Flood Hazard Layer; Florida Division of Corporations.
Choose Units One, Two and Three if you want a larger lot on Olde Cypress Drive or Treeline Drive, a newer home on Wild Orchid Court, or a preserve view on Lone Pine Lane at one of the community's most accessible detached price points. Choose Terramar if you want every lot on the golf course, a smaller association and a single price band where comparables are easy to read.
Selling in either neighborhood? Call Jesse direct at (239) 898-6072 for a free Units One, Two and Three at Olde Cypress home valuation. Deciding between them? Call Marc at (239) 287-5873 and read how we represent buyers.
The honest case for Units One, Two and Three at Olde Cypress is choice, lot size, association-maintained landscaping and a protected preserve on Lone Pine Lane; the honest case against is unpublished fees, the heaviest effective-map Zone AH exposure in Unit Two and Unit Three, strict parking rules and slower, deeper-discount sales than the Olde Cypress average.
McGreevy and Comisar have been Top 1% Real Estate Agents Nationally Since 2008, and we weigh every one of these points against the specific home. Selling? Call Jesse direct at (239) 898-6072 or request a free home valuation. Buying? Call Marc at (239) 287-5873 and read how we represent buyers in Southwest Florida.
If you're searching for a Units One, Two and Three at Olde Cypress listing agent, or thinking, 'I need someone to sell my Units One, Two and Three at Olde Cypress home...' you are selling into a neighborhood with no standing inventory, where the plat, the street and the paperwork decide the price. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008.
In the last 12 months we tracked all 26 Olde Cypress closings in the Southwest Florida MLS, pulled September 26, 2026, and every one of the eight in Units One, Two and Three. As the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate, and Jesse McGreevy and Marc Comisar account for over $900 million in personal sales inside that number.
Honors and recognition:
The Matrix pull did not record listing offices, so we state no represented-sale count; we will walk you through every closing on request.
Start with a free Units One, Two and Three at Olde Cypress home valuation. Jesse follows up with the sales that actually fit your home: the same plat and street, the same view, adjusted for size, age, updates and pool. For the full seller playbook, read how we sell homes in Units One, Two and Three at Olde Cypress.
(239) 898-6072, text or call. Confidential conversations welcome.
For a home priced to its street, yes: on September 26, 2026 there was no active listing in the association, so a well-presented home listed for the season faces no direct competition.
Against Lone Pine Lane sales only. The six in the last 12 months ran $775,000 to $1,110,000 for 2,097 to 2,543 square feet, and the county's 60-month median for Unit Three is $1,000,000 on 11 sales.
Against Wild Orchid Court's own record: six MLS closings in 48 months at a $1,929,111 median, and a 60-month county median of $2,175,000, with build year a major adjustment.
The buyer. Section 4.8 of the association's declaration makes it the transferee's obligation, collected at closing; the Board sets the amount each calendar year and the estoppel states it.
Yes, subject to the lease, which cannot exceed one year under Section 12.2. The buyer takes the lease, showings run through the tenant, and the closing should be timed to the lease end.
Units One, Two and Three at Olde Cypress owners and buyers work directly with Jesse McGreevy and Marc Comisar, who have sold Southwest Florida real estate for more than twenty years, lead Domain Realty Group, and checked every recent sale and recorded document in this association before writing this guide.
McGreevy and Comisar are the Domain Realty team behind this guide: Jesse McGreevy, Sales Associate, and Marc Comisar, Broker Associate. Jesse has been in the business since October 2004, the team launched in October 2008, and both work the North Naples golf-community market that Olde Cypress sits in.
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more about our team at DomainRealtyGroup.com.
McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008.
McGreevy and Comisar is a top-reviewed Units One, Two and Three at Olde Cypress realtor on Google, and the quotes below are genuine five star client reviews reproduced in the reviewer's own words. We publish no aggregate score and no star rating widget. Read the full set on the McGreevy and Comisar Google Business Profile.
★★★★★ “I can only say he is a refreshing and highly motivated professional. No tricks exaggerations nor falsehoods. His way of bringing quality clients is exceptional. He does not bring lookers. He brings buyers!” Dennis Overton, verified Google review
★★★★★ “Marc made an extremely stressful time of selling my parents' house easier because of his expertise, compassion, and diligence. I cannot thank him enough and I would recommend him without reservation.” Beth Shaw, verified Google review
★★★★★ “No one knows real estate, especially Florida real estate like Marc and Jesse. Smart and savvy. They also have a great team that is knowledgeable and professional.” Christian Schnabel, verified Google review
★★★★★ “Marc was great! He helped us find a place that matched our needs, without trying to upsell us into something too big. And he's helped us settle into the area. 100% recommendation!” Guy Avagliano, verified Google review
Selling a Units One, Two and Three at Olde Cypress home? Get a free Units One, Two and Three at Olde Cypress home valuation, or call Jesse direct at (239) 898-6072.
Buying in Units One, Two and Three at Olde Cypress? Call Marc at (239) 287-5873, or read how we represent buyers in Southwest Florida.
Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission.
These are the questions buyers ask most about Units One, Two and Three at Olde Cypress in Naples, answered from the recorded declarations, the Collier County roll, FEMA and the Southwest Florida MLS as of September 2026. Each answer is short; the sections above carry the detail and the sources.
The largest neighborhood in Olde Cypress, in ZIP 34119, unincorporated North Naples: 185 detached homes on three recorded plats governed by the Olde Cypress Homeowners' Association.
No. Unit One, Unit Two and Unit Three are the names of recorded plats of single-family lots. Every home is a detached, fee-simple house under Chapter 720.
Olde Cypress Drive and Treeline Drive in Unit One, Treeline Drive and Wild Orchid Court in Unit Two, and Lone Pine Lane in Unit Three.
No. Biscayne Place's eight homes share Treeline Drive and Olde Cypress Drive addresses but have their own association and declaration. Confirm the plat on the deed.
No. Fairway Preserve at Olde Cypress is a 264-unit condominium outside the gate, reached from Immokalee Road, and not part of the master association.
On September 26, 2026 there was no active listing and one pending sale on Treeline Drive, listed at $1,790,000.
The 24-month MLS median was $1,250,000 on 14 closings, with sales from $775,000 on Lone Pine Lane to $2,600,000 on Wild Orchid Court.
A median $451.39 per living square foot over 24 months (n = 14), from $321.98 to $803.21 per sale.
The 12-month median of $1,052,500 is below the 24-month $1,250,000 because six of eight recent sales were on Lone Pine Lane, the smallest homes, not because values fell.
A median 49 days on market over 24 months (n = 13), against 29 days for Olde Cypress as a whole in 12 months.
Not published. One quarterly invoice from the association includes the master share; the estoppel certificate gives the exact figure for a home.
In Collier County the buyer customarily pays the owner's title policy, plus the association's Resale Assessment and any master working capital contribution. The contract controls.
No. Olde Cypress has no Community Development District; the 2025 tax bill shows only a garbage charge as a non-ad valorem line.
2026 preliminary medians are $8,438 in Unit One, $10,252 in Unit Two and $5,754 in Unit Three, at 9.5058 mills in 2025.
Social membership in The Club at Olde Cypress is mandatory with the home under master declaration Section 14.02. Golf is optional.
The club does not publish initiation or dues. Ask its membership office at (239) 596-4797 for current terms in writing.
No. Neither declaration contains an age restriction.
Yes, for 60 days to one year, no more than four leases a year, with association and master approval.
No. The 60-day minimum and the ban on timeshare and lodging use rule out vacation rental.
Yes. Dogs, cats and birds are allowed, leashed or carried outside, and never left alone on a lanai.
No. Commercial vehicles, vans, boats, trailers and campers must be in an enclosed garage, and every car must be garaged overnight.
The association maintains lawns, landscaping and irrigation equipment on every lot; the owner maintains the house, roof cleaning, driveway and sidewalk.
On the effective 2012 FEMA map, 70 of 185 footprints sit wholly in Zone AH; on the preliminary 2025 map all 185 are in Zone X.
Only if your lender requires it for that building under the effective map. The ZIP 34119 median single-family NFIP policy was $1,259 a year.
Collier County Evacuation Zone E, and Florida's Category 4 storm surge zone.
Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026-2027.
Mostly 2000 to 2007; Unit Two has six homes that first appear on county layers between 2011 and 2023.
From about 2,100 square feet of living area on Lone Pine Lane to about 4,400 on Treeline Drive and Wild Orchid Court.
Unit One, with a 14,257 square foot median lot, then Unit Two at 13,440 and Unit Three at 9,785.
Terramar has 55 all-golf homes on smaller lots and sold faster over 48 months; Units One, Two and Three has three price bands and larger lots in Units One and Two.
Book through an agent: the gate admits buyers outside weekend open house hours only with an agent or owner. Call Marc at (239) 287-5873, or see our buyer's guide for Units One, Two and Three at Olde Cypress.
These are the questions Units One, Two and Three at Olde Cypress sellers ask us most, answered from the recorded declarations, Florida statutes, the Collier County record and the Southwest Florida MLS as of September 2026. For a price on your own home, Call Jesse direct at (239) 898-6072.
It depends on plat, street, view, size and age. Start with a free valuation and the sales on your own street.
Eight MLS closings in 12 months, $775,000 to $1,275,000, at a $1,052,500 median; 14 in 24 months at $1,250,000.
$2,800,000 on Wild Orchid Court in June 2024 in the MLS; the county's highest recorded sale is $3,100,000, also Wild Orchid Court, in August 2022.
Yes. Over 48 months the MLS medians were $1,929,111 on Wild Orchid Court, $1,757,500 on Olde Cypress Drive, $1,500,000 on Treeline Drive and $1,000,000 on Lone Pine Lane.
Rarely. Automated models blend three plats and Biscayne Place addresses; a comparable from the wrong street can miss by hundreds of thousands of dollars.
The 24-month median was 93.16% of final list price; one of 14 closed at or above list.
A median 49 days over 24 months, but several homes priced to their street went under contract in under a week.
On September 26, 2026 there was no active listing in the association and one pending sale.
Naples' busiest buying season runs through the winter, so a listing prepared in the fall is in front of seasonal buyers when they arrive.
You must give the buyer the association disclosure summary before the contract is signed; otherwise the buyer may void it within three days of receiving it or before closing.
The Olde Cypress Homeowners' Association declaration requires Board approval of leases, not of sales. The estoppel certificate and gate registration still apply.
It states what is owed on the lot. The association must issue it within 10 business days; the fee, capped at $299 for a current account, is customarily a seller cost.
The buyer, under Section 4.8 of the declaration, in an amount the Board sets each calendar year.
The master declaration, Section 8.13, authorizes one at transfer in a Board-set amount; the current amount was not located and the estoppel states it.
Social membership passes automatically by covenant. A golf membership is between you and the club; get the club's current terms in writing.
The club is non-equity, and owners hold no equity interest under master declaration Section 14.03. Any refund depends on the club's own membership terms.
$0.70 per $100 of price, customarily paid by the seller: $8,750 on a $1,250,000 sale.
In Collier County the buyer customarily pays for it and chooses the closing agent, but the contract controls.
Commission is negotiable. Since August 17, 2024, practice changes from the NAR settlement mean offers of buyer-agent compensation are not made through the MLS.
For a home built before 2002, yes: a four-point and wind mitigation report answers the insurer's questions before the buyer asks them.
Yes. Fourteen homes here hold FEMA letters of map amendment; a letter can remove a lender's flood insurance requirement for that structure.
Say so, and show the elevation certificate. The preliminary 2025 map places every home here in Zone X, though it is not effective until 2027.
Only the master association's standardized green wooden For Sale sign; no other signs without approval.
Public open houses run Saturday and Sunday, noon to 5 p.m.; signs come from the guard house against a $20 refundable deposit.
Yes, subject to the lease, which cannot run past one year; the buyer takes the lease.
Usually not a full remodel. Paint, landscaping touch-ups within architectural rules and documented roof and window work return more than a new kitchen chosen for someone else.
Yes, for any exterior change, from both the neighborhood committee and the master association.
Against Treeline Drive sales, adjusted for plat and view: nine Unit Two Treeline Drive county sales in 60 months had a $1,285,000 median.
Against Olde Cypress Drive's eight MLS closings, $1,325,000 to $2,350,000, and the 60-month county median of $1,695,000 for Unit One.
Your buyer does not inherit your Save Our Homes cap, so their bill will rise toward the just value; price with that in mind.
Yes. We can market quietly to our buyer database, though a thin-supply neighborhood usually rewards full exposure.
Because we tracked every one of the 31 MLS closings and the recorded documents here, and have been Top 1% Real Estate Agents Nationally Since 2008.
Call Jesse direct at (239) 898-6072, or request a free Units One, Two and Three at Olde Cypress home valuation.
Every fact in this Units One, Two and Three at Olde Cypress guide traces to a primary record below: the association and master association documents, the club, Collier County, the State of Florida, FEMA and federal data, the school district and dated reporting. No brokerage, listing portal or IDX feed is cited.
The key documents for Units One, Two and Three at Olde Cypress are published by the Olde Cypress master association, Collier County and the State of Florida; the table links each to its issuing authority. The 1999 original declaration, OR 2546 PG 973, is available through the Collier County Clerk's Official Records search.
Document | Issued by | Date | Link |
|---|---|---|---|
Olde Cypress Homeowners' Association Amended and Restated Declaration | Olde Cypress Homeowners' Association, recorded with the Collier County Clerk | 2016, OR 5260 PG 3502 | |
Amended and Restated Declaration, Articles and Bylaws for Olde Cypress | Olde Cypress Master Property Owners Association | November 27, 2019 | |
Leasing amendment | Olde Cypress Master Property Owners Association | 2013, OR 4874 PG 3783 | |
Community access and gate procedures | Olde Cypress Master Property Owners Association | November 2024 | |
Lake management | Olde Cypress Master Property Owners Association | October 2024 | |
Floodplain Protection Newsletter | Collier County | March 2026 | |
Uniform Mitigation Verification Inspection Form | Florida Office of Insurance Regulation | rev. January 2012 |
Market data from Southwest Florida MLS, pulled September 2026. McGreevy and Comisar, Best Realtor for Units One, Two and Three at Olde Cypress. Brokered by Domain Realty. Jesse McGreevy, FL Lic. SL3101296 · Marc Comisar, FL Lic. BK3060671.
Thinking about buying or selling in Southwest Florida? Tell us what you are trying to do and we will tell you honestly what it will take. McGreevy and Comisar, Domain Realty Group.
