Updated September 2026
Buy in Units One, Two and Three at Olde Cypress, Naples: Lone Pine Lane, Treeline Drive, Olde Cypress Drive and Wild Orchid Court priced sale by sale, plus the club, costs and flood file. Sell or buy with McGreevy and Comisar.
Updated September 2026 · By Jesse McGreevy and Marc Comisar, Domain Realty
Buying a home in Units One, Two and Three at Olde Cypress means choosing among three different markets that share one homeowners' association: the golf-course homes of Unit One on Olde Cypress Drive and west Treeline Drive, the larger lots of Unit Two on east Treeline Drive and Wild Orchid Court, and the compact Lone Pine Lane homes of Unit Three. Together they are 185 detached homes, the largest neighborhood inside the gate. This page is the purchase side of our Units One, Two and Three at Olde Cypress neighborhood guide, part of the gated golf community of Olde Cypress in North Naples, Florida 34119: what each street costs, what you will pay to own it, what to request before you are committed, and how we negotiate for you.
Units One, Two and Three is not Fairway Preserve at Olde Cypress, the 264-unit condominium off Immokalee Road that sits outside the gate and the master association, and not Olde Cypress Mill, a homeowners' association in Spring, Texas.
If you are still choosing an agent, our guide to the best real estate agents in Naples sets the city's teams side by side on the public record. If you already own on one of these four streets and are selling to buy again, start with how we sell homes in Units One, Two and Three at Olde Cypress and a data-backed valuation of your Units One, Two and Three home.
Call Marc Comisar at (239) 287-5873 or Jesse McGreevy at (239) 898-6072. We have been Top 1% Real Estate Agents Nationally Since 2008, and before you tour a single home we will show you which of the three units fits your budget and what it costs to own.
Buying a home in Units One, Two and Three at Olde Cypress takes a street decision before a house decision, because Lone Pine Lane, Treeline Drive, Olde Cypress Drive and Wild Orchid Court price like separate markets. It also takes the club's figures in writing, the estoppel, and a flood file read building by building.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
Everything below comes from the Collier County Property Appraiser, 2026 tax roll (preliminary) and recorded qualified sales, the Southwest Florida MLS, the recorded declarations, the club's own pages and FEMA. Where the public record stops, this page says so.
Olde Cypress Homeowners' Association, Inc., filed on February 19, 1999 and active on Sunbiz, governs Olde Cypress Unit One (61 homes), Unit Two (69) and Unit Three (55) under its 2016 Amended and Restated Declaration, OR 5260 PG 3502. "Wild Orchid" and "Treeline" are streets, not neighborhoods, and an April 26, 2011 county commission packet used older names for the same land: "Woodsedge" for Units One and Two (130 homes) and "Ibis Landing" for Unit Three (55).
Every home is reached through one staffed gatehouse on Treeline Drive at Logan Boulevard North, about a quarter mile north of Immokalee Road. Unit One begins just inside it on Olde Cypress Drive and west Treeline Drive; Unit Two continues east on Treeline Drive and the Wild Orchid Court cul-de-sac; Unit Three is Lone Pine Lane, between the golf course and the master preserve.
Treeline Drive and Olde Cypress Drive also carry the eight estate homes of Biscayne Place, a separate association near the gate. Every figure on this page assigns sales by the county roll's plat for each address, so Biscayne Place sales are not counted; confirm the plat on any listing before you write.
No Community Development District, confirmed against Collier County's CDD layer, the state's dissolved-district list and a 2025 Lone Pine Lane tax bill. No condominium or attached product. No member assessments or food minimum at the club, per its About Us page. And no published association fee.
Fairway Preserve at Olde Cypress has its own gate off Immokalee Road, its own condominium declaration, no place in the master association, no club social membership and a Gulf Coast High assignment. Owners in Units One, Two and Three carry the membership and the Aubrey Rogers High assignment.
McGreevy and Comisar represent buyers in Units One, Two and Three at Olde Cypress from the record outward: the county roll, every MLS closing on the four streets, the recorded declarations, the club's pages and FEMA's letters. We have been Top 1% Real Estate Agents Nationally Since 2008 and the #1 Team in Southwest Florida since 2012.
Those are career numbers across Lee and Collier County. McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team; as its leaders, our team has closed over $2.5 billion in real estate.
In the last 12 months Units One, Two and Three at Olde Cypress has seen 8 MLS resales. You get every sale on the four streets, with the source and date beside each figure.
McGreevy and Comisar are a top-reviewed Units One, Two and Three at Olde Cypress buyer's agent team on Google. The quotes below are genuine verified Google reviews in the client's own words; every review is on our Google Business Profile.
★★★★★ "Highly recommend Marc as a realtor. His devotion to finding you the perfect house is obvious and a breath of fresh air at such a stressful time." Verified Google review
★★★★★ "Jesse is the best Realtor I have used. He found us our dream home even though it took months as we were not the easiest to please." Verified Google review
★★★★★ "Marc is one of the most down to earth realtors that really listens to your needs and is exceptional at finding the right house." Verified Google review
★★★★★ "He did a great job planning and made the most of the time we had together. I would highly recommend reaching out to Marc for any real estate needs." Verified Google review
The right unit for your budget before you fall for a house, the plat confirmed, the club and association figures before your inspection period ends, the flood file for the specific building, and an offer written from the street's recorded sales. Selling first? Get a Units One, Two and Three home valuation or call Jesse direct at (239) 898-6072; buying, read how we represent buyers in Naples or call Marc at (239) 287-5873.
The market for buyers in Units One, Two and Three at Olde Cypress is thin and negotiable: 14 MLS closings in 24 months at a $1,250,000 median, a median 93.16 percent of the final list price, and no active listing on September 26, 2026. Homes that sold quickly sold near list; homes that waited gave up more.
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 31 closings in Units One, Two and Three recorded in the Southwest Florida MLS since September 2022, each assigned to its unit by the county roll's plat for the address, and in the last 12 months we tracked 8 of them, every one a resale of a detached home. Twelve months holds fewer than ten sales, so this page leads with the 24-month window and shows the others beside it.
| Measure (Southwest Florida MLS) | 12 months | 24 months | 36 months | 48 months |
|---|---|---|---|---|
| Closings | 8 (small sample) | 14 | 21 | 31 |
| Dollar volume | $8,280,000 | $18,978,000 | $30,594,500 | $48,908,902 |
| Median sold price | $1,052,500 | $1,250,000 | $1,285,000 | $1,450,000 |
| Median sold price per living sq ft | $420.92 | $451.39 | $470.09 | $475.59 |
| Median sold-to-final-list | 94.52 percent | 93.16 percent | 93.38 percent | 94.00 percent |
| Median days on market | 49 (n=7) | 49 (n=13) | 48.5 (n=20) | 45 (n=30) |
| Price range | $775,000 to $1,275,000 | $775,000 to $2,600,000 | $775,000 to $2,800,000 | $775,000 to $2,800,000 |
| At or above list | 1 | 1 | 3 | 7 |
Windows end September 26, 2026. Figures are medians, not means; even-count medians are the mean of the middle pair ($1,005,000 and $1,100,000 at 12 months, $1,225,000 and $1,275,000 at 24 months). One sale entered after closing has no days on market.
The drop from a $1,450,000 median over 48 months to $1,052,500 over 12 months is mostly mix, not a 27 percent fall in values: six of the last eight closings were on Lone Pine Lane, the lowest-priced street, and none was on Wild Orchid Court or Olde Cypress Drive.
On a home listed at $1,250,000, the 24-month median of 93.16 percent means a price near $1,164,500, a gap of about $85,500. The deepest discounts went to homes that had waited, 81.72 percent after 124 days on Treeline Drive and 93.38 percent after 293 days on Lone Pine Lane; a home priced right drew 98.08 percent in 6 days on Treeline Drive in April 2026.
| Street | Status on September 26, 2026 | List price | Beds and baths | Living area | Days on market |
|---|---|---|---|---|---|
| Treeline Drive | Pending, contingent | $1,790,000 | 4 bedrooms plus den, 4 baths | 3,350 sq ft | 4 |
That is the whole inventory (Southwest Florida MLS Matrix, retrieved September 26, 2026). For the live list, see the Olde Cypress inventory on DomainRealtyGroup.com, our team's listings site, or ask Marc about owners who may sell before they list.
| Twelve months to September 26, 2026, Southwest Florida MLS | Units One, Two and Three | Terramar at Olde Cypress | All of Olde Cypress |
|---|---|---|---|
| Closings | 8 (small sample) | 3 (small sample) | 26 |
| Median sold | $1,052,500 | $1,099,000 | $1,105,000 |
| Median sold per living sq ft | $420.92 | $547.58 | $472.75 |
| Median sold-to-list | 94.52 percent | 92.11 percent | 97.52 percent |
| Median days on market | 49 | 7 | 29 |
| Listings on September 26, 2026 | 0 active, 1 pending | 2 active | 5 active, 1 pending |
Lone Pine Lane dominated the association's last year; over 48 months its median was $1,450,000. A buyer finds more negotiating room here than in Olde Cypress as a whole.
This is a public-record sale from the Southwest Florida MLS, not a McGreevy and Comisar transaction. On May 14, 2026, a 2,340 square foot, four-bedroom Lone Pine Lane home listed at $1,169,000 sold for $1,100,000 after 13 days, 94.10 percent of list. It closed fast and still about 6 percent under list, so on Lone Pine Lane write from the street's recorded sales, not the ask.
A home in Unit One at Olde Cypress, the 61 golf-course homes on Olde Cypress Drive and west Treeline Drive, costs more than Lone Pine Lane and less than Wild Orchid Court: the county's 36-month recorded median is $1,847,500 on 6 sales and the 60-month median $1,695,000 on 12, both small samples.
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 is the master plat of Olde Cypress, and it also carries the master association's tracts and the club parcel. On the 2026 preliminary Collier County roll its 61 homes sit on lots with a median of 0.32 acre (0.25 to 0.43), 60 of 61 back onto the golf course, and the earliest building year runs 2000 to 2006, with a median of 2001. The median 2026 preliminary just value is $1,294,566 ($869,265 to $1,629,566), and the median 2026 preliminary total tax is $8,438. On the roll, 47 of 61 homes (77.0 percent) carry a homestead exemption, and 8 owners have a mailing address outside Florida.
Units One, Two and Three at Olde Cypress had no active listing and one pending sale on September 26, 2026, and its 24-month median was $1,250,000 at 93.16 percent of list, so the buyer who is ready when a home appears decides the outcome. Call Marc Comisar at (239) 287-5873, request your Units One, Two and Three buyer consultation, or read how we represent buyers in Naples. Selling a home on one of these streets first? Get a free Units One, Two and Three home valuation or call Jesse McGreevy direct at (239) 898-6072.
Over 48 months the Southwest Florida MLS recorded 8 closings on Olde Cypress Drive at a median of $1,757,500 (the mean of $1,715,000 and $1,800,000), a small sample:
Every sale was a three-bedroom-plus-den plan of 2,786 to 3,956 square feet, and none has closed since July 2025, so a buyer here prices from sales 14 months old or more.
Unit One's 19 Treeline Drive homes share the street with Unit Two, and the MLS figures below count Treeline Drive as one street. On the county side, Unit One's recorded qualified sales show 6 in 36 months at a $1,847,500 median (the mean of $1,715,000 and $1,980,000) and 12 in 60 months at $1,695,000 (the mean of $1,675,000 and $1,715,000). Both are small samples, and the county file's newest recording in the community is May 22, 2026.
Sixty of 61 lots touch the golf course parcel on the county map, the highest share in the association, and the clubhouse sits a short drive west. If a fairway view is the reason you are buying, Unit One delivers it most consistently. Selling a Unit One home first? Get a Units One, Two and Three home valuation or call Jesse direct at (239) 898-6072; buying, read how we represent buyers in Naples or call Marc at (239) 287-5873.
A home in Unit Two at Olde Cypress, the 69 homes on east Treeline Drive and Wild Orchid Court, spans the widest range in the association: Wild Orchid Court carries the top of the market, with a 48-month MLS median of $1,929,111 on 6 closings, while Treeline Drive's 8 closings had a $1,500,000 median.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
On the 2026 preliminary Collier County roll, Unit Two's 69 homes sit on lots with a median of 0.30 acre (0.26 to 0.43), built 2000 to 2023 with a median of 2003. The median 2026 preliminary just value is $1,453,941 ($922,084 to $2,073,797), the highest of the three units, and the median 2026 preliminary total tax is $10,252. On the roll, 52 of 69 homes (75.4 percent) are homesteaded and 12 owners mail from another state. Fifty-five lots back onto the golf course and 18 on the east side border the master preserve.
Wild Orchid Court is a 25-home cul-de-sac off Treeline Drive. Over 48 months the MLS recorded 6 closings there at a $1,929,111 median (the mean of $1,908,222 and $1,950,000), a small sample:
The two same-day August 2023 closings, after more than a year listed and above list, fit homes contracted before or during construction, and the roll shows two Unit Two homes built in the 2020s; that is our reading, so ask for permits. The $2,800,000 June 2024 sale is the association's highest MLS closing in 48 months.
Treeline Drive's 8 MLS closings over 48 months, counting both units, had a $1,500,000 median (the mean of $1,325,000 and $1,675,000), a small sample:
The range, $1,225,000 to $2,280,000, is why a Treeline Drive offer needs the specific comparable, not the street median; the September 26, 2026 pending listing is also here.
Collier County recorded qualified sales for Unit Two show 6 in 36 months at a $1,305,000 median (the mean of $1,285,000 and $1,325,000) and 15 in 60 months at $1,775,000; over 60 months Treeline Drive's 9 had a $1,285,000 median and Wild Orchid Court's 6 a $2,175,000 median (the mean of $1,950,000 and $2,400,000). All are small samples.
A home in Unit Three at Olde Cypress, the 55 homes of Lone Pine Lane, costs the least in the association and is where most of the recent sales happened: 9 MLS closings over 48 months at a $1,000,000 median, from $775,000 to $1,110,000, and six of the association's last 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)
Unit Three is one of the two most compact detached products inside Olde Cypress, with lots from 7,534 to 19,852 square feet and a median of 9,785. Twenty-six homes back onto the golf course and 33 onto the large master preserve. County footprint layers show the homes finished between about 2000 and 2007. The median 2026 preliminary just value for Unit Three is $783,010 and the median 2026 preliminary total tax is $5,754, both the lowest in the association.
| Close | Beds and baths | Living area | Final list | Sold | Per living sq ft | Sold-to-list | Days |
|---|---|---|---|---|---|---|---|
| May 2026 | 2 plus den, 2.5 | 2,097 | $850,000 | $850,000 | $405.34 | 100.00 percent | Entered after closing |
| May 2026 | 4, 3 | 2,340 | $1,169,000 | $1,100,000 | $470.09 | 94.10 percent | 13 |
| March 2026 | 2 plus den, 2.5 | 2,217 | $1,045,000 | $1,005,000 | $453.32 | 96.17 percent | 49 |
| February 2026 | 3, 2.5 | 2,543 | $1,199,000 | $1,110,000 | $436.49 | 92.58 percent | 76 |
| February 2026 | 3 plus den, 3 | 2,320 | $990,000 | $940,000 | $405.17 | 94.95 percent | 42 |
| December 2025 | 3 plus den, 3 | 2,407 | $829,900 | $775,000 | $321.98 | 93.38 percent | 293 |
| February 2024 | 2 plus den, 2.5 | 2,217 | $1,100,000 | $1,025,000 | $462.34 | 93.18 percent | 106 |
| November 2023 | 4, 3 | 2,340 | $999,999 | $925,000 | $395.30 | 92.50 percent | 20 |
| May 2023 | 2 plus den, 2.5 | 2,097 | $999,000 | $1,000,000 | $476.87 | 100.10 percent | 4 |
Source: Southwest Florida MLS Matrix, retrieved September 26, 2026. The 9 closings are a small sample with a $1,000,000 median (odd count, observed), on 2,097 to 2,543 square feet.
Five Lone Pine Lane sales were recorded with the county between February and May 2026; the 36-month county record for Unit Three is 8 sales at a $972,500 median (the mean of $940,000 and $1,005,000), and 11 in 60 months at $1,000,000. Current comparables exist here, so a seller asking well above $1,110,000 needs a reason the record does not show.
Lone Pine Lane is the one street where the view splits almost evenly between golf and a master preserve that may not be altered. The sample is too small to measure a premium, so we price each side from the homes that sold. Own on Lone Pine Lane already? See how we sell homes in Units One, Two and Three or call Jesse direct at (239) 898-6072; buying, call Marc at (239) 287-5873 or read how we represent buyers in Naples.
The three markets inside Units One, Two and Three at Olde Cypress fit three budgets: Lone Pine Lane around $775,000 to $1,110,000, Treeline Drive and Olde Cypress Drive around $1,225,000 to $2,350,000, and Wild Orchid Court around $1,775,000 to $2,800,000, on 48 months of MLS closings. The table sets them side by side.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
| Measure | Unit One | Unit Two | Unit Three |
|---|---|---|---|
| Streets | Olde Cypress Drive (42), west Treeline Drive (19) | East Treeline Drive (44), Wild Orchid Court (25) | Lone Pine Lane (55) |
| Homes on the 2026 preliminary roll | 61 | 69 | 55 |
| Median lot | 0.32 acre | 0.30 acre | 9,785 sq ft (about 0.22 acre) |
| Backs onto golf | 60 of 61 | 55 of 69 | 26 of 55 (33 preserve) |
| Median 2026 preliminary just value | $1,294,566 | $1,453,941 | $783,010 |
| Median 2026 preliminary total tax | $8,438 | $10,252 | $5,754 |
| County recorded sales, 36 months | 6, median $1,847,500 | 6, median $1,305,000 | 8, median $972,500 |
| County recorded sales, 60 months | 12, median $1,695,000 | 15, median $1,775,000 | 11, median $1,000,000 |
| MLS closings by street, 48 months | Olde Cypress Drive 8, median $1,757,500 | Wild Orchid Court 6, median $1,929,111 | Lone Pine Lane 9, median $1,000,000 |
| Effective 2012 flood map, footprints wholly Zone AH | 11 | 30 | 29 |
Treeline Drive's 8 MLS closings (median $1,500,000) span Units One and Two. Every count is a small sample, and just values are tax assessments, not prices.
| Budget | Where it buys in Units One, Two and Three, on recent sales |
|---|---|
| Under $1,000,000 | Lone Pine Lane, two-bedroom-plus-den and three-bedroom plans near 2,100 to 2,400 square feet |
| $1,000,000 to $1,300,000 | The larger Lone Pine Lane plans; the occasional Treeline Drive home that has waited |
| $1,300,000 to $2,000,000 | Most of Treeline Drive and Olde Cypress Drive; the lower end of Wild Orchid Court |
| $2,000,000 and up | Wild Orchid Court and the largest Olde Cypress Drive and Treeline Drive plans |
The 48-month MLS median is $475.59 per living square foot, from $321.98 on Lone Pine Lane to $803.21 on Wild Orchid Court; never compare it with county building area, which includes garages.
The county file holds 303 qualified sales in the association since 1999, at an all-history median of $765,000; the last ten years run as follows.
| Year | Recorded qualified sales | Median |
|---|---|---|
| 2016 | 7 | $840,000 |
| 2017 | 7 | $744,000 |
| 2018 | 11 | $800,000 |
| 2019 | 11 | $740,000 |
| 2020 | 7 | $1,025,000 |
| 2021 | 12 | $1,137,600 |
| 2022 | 11 | $1,510,000 |
| 2023 | 8 | $1,737,500 |
| 2024 | 5 | $1,438,000 |
| 2025 | 7 | $1,715,000 |
| 2026, through May 22 | 6 | $1,052,500 |
Source: Collier County Property Appraiser recorded qualified sales, improved, over $100,000, file dated August 29, 2026. Every year is a small sample.
Owning a home in Units One, Two and Three at Olde Cypress each year costs a quarterly invoice from the Olde Cypress Homeowners' Association that includes the master share, mandatory club social dues, any golf you choose, property taxes at the 2025 rate of 9.5058 mills, a homeowners policy and flood insurance where a lender requires it.
Data updated: September 2026 (Olde Cypress Master Property Owners Association About page; The Club at Olde Cypress membership and About Us pages; 2025 Collier County Tax Collector bill for a Lone Pine Lane home; OpenFEMA NFIP policies as of September 8, 2026)
| Layer | Amount | How often | Source |
|---|---|---|---|
| Olde Cypress Homeowners' Association assessment, including the master share | Not published (resident portal only) | Quarterly | Master association About page |
| Club social membership | Mandatory; dues not published | Annual, set by the club | Declaration Section 14.02 |
| Golf membership, Full or Associate | Optional; initiation and dues not published | Initiation plus annual | Club membership page |
| Member assessments and food minimum | None | Not applicable | Club About Us page |
| Property taxes | 9.5058 mills in 2025 | Annual | 2025 Collier County tax bill |
| Garbage, non-ad valorem | $261.91 on the 2025 Lone Pine Lane bill | Annual | Same |
| Community Development District | None | Not applicable | Collier County CDD layer |
| Flood insurance | Median $1,259 per year, single-family, ZIP 34119 | Annual, where required or chosen | OpenFEMA NFIP policies |
| Master working capital contribution | Board-set; not located publicly | Once, at transfer | Declaration Section 8.13 |
The invoice pays the association's own costs, including the Unit Two road tract it holds, and your share of the master association: the gatehouse, common grounds, streetlights, paving, stormwater, the master preserve and basic exterior landscaping of each home. Ask for both budgets during your inspection period.
Freddie Mac's Primary Mortgage Market Survey put the 30-year fixed rate at 7.03 percent as of September 24, 2026. At that rate, a purchase at the association's 24-month median of $1,250,000 with 20 percent down, a $1,000,000 loan, carries principal and interest of about $6,673 a month, before taxes, insurance, the quarterly invoice and club dues. Your lender's quote replaces this illustration.
Club membership for a Units One, Two and Three buyer works in two tiers: social membership in The Club at Olde Cypress is mandatory and automatic when you acquire the home, under Section 14.02 of the recorded 2019 master declaration, while Full Golf and Associate Golf are optional purchases. The club is non-equity and privately owned.
"By acquisition of a Parcel, each Owner automatically becomes a social member of The Club at Olde Cypress," under Section 14.02 of the 2019 Amended and Restated Declaration. The rule is the same on all four streets, whether your lot faces a fairway or the preserve.
The club describes itself as non-equity and privately owned by the Stock family of companies; Section 14.03 gives owners no equity or vote, and its $16 million clubhouse renovation, reopened in spring 2026, carried no member assessment.
Social members use the clubhouse and dining, clay tennis courts, pickleball, the fitness center and the pool; Full Golf and Associate Golf are separate, per the membership page. The club publishes no dues or initiation, third-party figures conflict widely, from roughly $45,000 to $175,000, and we quote none of them; get current figures in writing from the membership office at (239) 596-4797.
Buying in Units One, Two and Three at Olde Cypress runs in nine steps: choose the street before the house, confirm the plat, budget the carrying costs, check the building's flood position, sign a buyer agreement and get pre-approved, write the offer, collect the disclosure summary and estoppel, get the club's figures and inspections, then close and enroll.
Lone Pine Lane, Treeline Drive, Olde Cypress Drive and Wild Orchid Court are four price levels, from under $1,000,000 to over $2,500,000, and the choice sets the budget and the comparable sales.
On Treeline Drive and Olde Cypress Drive, check that the address is in Unit One or Unit Two and not Biscayne Place, which has its own association.
Add the quarterly invoice, club social dues, any golf, taxes on your purchase price rather than the seller's bill, and insurance, and ask for the written figures early.
Ask for the elevation certificate and any FEMA letter, and let your lender run a determination on the specific building.
Since August 17, 2024, buyers sign a written agreement before touring; a pre-approval lets you move when the one listing you want appears.
Build the inspection period around the association and club documents; with a 24-month median of 93.16 percent of list, there is usually room on price.
The seller owes the Chapter 720 disclosure summary before you sign; the estoppel states the assessment and any contribution due at transfer.
Get dues and any golf figures from the membership office at (239) 596-4797, then a full inspection, a four-point and a wind mitigation report, and bind insurance early.
Close with the title company you choose, file for homestead by March 1 of the following year if it applies, and register with the club and the gate.
A Units One, Two and Three buyer should request the Chapter 720 disclosure summary before signing, the 2016 declaration of the Olde Cypress Homeowners' Association and the 2019 master declaration, both budgets, the estoppel certificate, the club's written figures, the leasing amendment, the elevation certificate and any FEMA letter, and the seller's disclosures.
Under Florida Statutes 720.401, a prospective parcel owner "must be presented a disclosure summary before executing the contract for sale," and on a resale the seller supplies it. If it is not delivered, you may void the contract "within 3 days after receipt of the disclosure summary or prior to closing, whichever occurs first," and that right cannot be waived. There are no condominiums in this association, so Chapter 720 is the only regime.
The same transaction, seen from our Units One, Two and Three seller page, reads identically: the seller owes the disclosure summary before contract, the master association may collect a working capital contribution at transfer under Section 8.13 in a Board-set amount we could not locate publicly, and the contract says who pays it. This is information, not legal advice.
Under Florida Statutes 720.30851, the estoppel states the regular assessment, what is paid through, any balance and any capital contribution or transfer fee due at closing. Confirm it covers the master share.
The 2016 association declaration, the 2019 master declaration, the 2013 leasing amendment, the master association's documents library, the lake management document and the association budget.
Units One, Two and Three at Olde Cypress sit on FEMA maps effective May 16, 2012 that put many footprints in Zone AH, shallow ponding, and the rest in Zone X, with Unit Two the most exposed. FEMA's March 20, 2025 preliminary map places all 185 homes in Zone X, but it is not effective yet, and letters are address-specific.
Data updated: September 2026 (FEMA National Flood Hazard Layer, effective and preliminary, overlaid on Collier County building footprints, computed September 23, 2026)
| Unit | Homes | Footprint wholly in Zone AH | Partly | Zone X only | Nearest base flood elevation lines |
|---|---|---|---|---|---|
| Unit One | 61 | 11 | 20 | 30 | 12.0 to 13.0 ft NAVD88 |
| Unit Two | 69 | 30 | 35 | 4 | 12.5 to 13.5 ft NAVD88 |
| Unit Three, Lone Pine Lane | 55 | 29 | 14 | 12 | 12.5 to 13.0 ft NAVD88 |
The zone line runs lot to lot on the same street. Every FEMA letter we read here names ponding and overland flow as the source, not the Gulf; there is no Zone VE.
Since 2012 FEMA has issued eight structure-removal letters on Treeline Drive and Wild Orchid Court, including LOMA 12-04-7997A, and six on Lone Pine Lane, most recently LOMA 25-04-6753A in September 2025; each covers only the building it names. A 2021 county elevation certificate for a Wild Orchid Court home shows a floor 3.6 feet above its 13-foot base flood elevation.
Collier County opened the 90-day appeal period on August 19, 2026, with the new map targeted for summer 2027, per its August 2026 release. Until then the 2012 map governs lending, and Zone X is a lower-risk mapped zone, not an exemption.
Get the elevation certificate, search the address on the FEMA Flood Map Service Center, let the lender run its determination, and get a flood quote even where it is not required. The median single-family NFIP policy in ZIP 34119 costs $1,259 a year.
No public agency publishes a homeowners or windstorm premium for Units One, Two and Three at Olde Cypress, so we will not invent one. Flood is different: FEMA data shows a median single-family NFIP cost of $1,259 a year in ZIP 34119, and the wind premium turns on the roof, openings and build era.
A federally backed or regulated mortgage on a building in Zone AH requires flood insurance; in Zone X it does not, though a lender may still ask. With 139 of 185 footprints wholly or partly in Zone AH on the effective map, many buyers here will face the requirement.
Homes here are designed to a 160 mph ultimate wind speed under the current Florida Building Code. County footprint layers show 43 of 61 Unit One homes, 21 of 69 in Unit Two and 26 of 55 in Unit Three already standing in the 2000 or 2002 layer; impact openings and a newer roof earn the credits an original home lacks.
Citizens Property Insurance fell from 6,042 Collier County homeowners policies at the end of 2024 to 1,839 by August 31, 2026, per its detail by county report, so private options have widened. Unincorporated Collier County's Community Rating System Class 5 takes 25 percent off NFIP premiums inside the Special Flood Hazard Area and 10 percent outside it.
Units One, Two and Three at Olde Cypress sit in Collier County Evacuation Zone E and Florida's Category 4 storm surge zone, about 6.7 miles inland, outside the Coastal High Hazard Area. The Census block group shows only 3 NFIP flood claims ever, none coded to Hurricane Ian.
Hurricane Irma in 2017 accounts for 88 of ZIP 34119's 124 all-time NFIP claims, per the OpenFEMA claims dataset; Ian's 2022 surge flooding was concentrated south and west of US 41, well away from these streets by our reading. Zone E is called only in larger-surge storms. Wind and roof claims do not appear in flood data, so ask the seller for repair invoices and permits.
Property taxes after you buy in Units One, Two and Three at Olde Cypress will be set on your purchase-year just value at the 2025 rate of 9.5058 mills plus a garbage charge, with no CDD. Your bill will usually be higher than the seller's, because a buyer does not inherit the seller's Save Our Homes cap.
On the 2026 preliminary Collier County roll, the median total tax is $7,532 across the association: $8,438 in Unit One, $10,252 in Unit Two and $5,754 in Unit Three, with 136 of 185 homes homesteaded. As our arithmetic, not a bill: at 9.5058 mills, a just value of $1,250,000 produces about $11,882 before any exemption, plus the $261.91 garbage charge.
If the home will be your primary residence, file for homestead by March 1 of the year after you buy. If you are leaving another Florida homestead, you may be able to transfer part of its accumulated Save Our Homes benefit, within statutory limits.
The rules that decide fit in Units One, Two and Three at Olde Cypress are the master leasing limits, the overnight parking ban, the two-step architectural review, the lake and preserve easements and the pet rules, all in the recorded 2019 master declaration or its leasing amendment, with the 2016 association declaration adding its own.
No lease under 60 days and no more than four a year, whole home only, with a $100 fee, a $1,000 refundable deposit and Board approval; seasonal rental works, vacation rental does not. No vehicles on Olde Cypress streets overnight and no more than two in a driveway, which matters on Lone Pine Lane's compact lots.
Exterior changes need association and master approval, and conservation buffers on the 33 Lone Pine Lane and 18 Unit Two preserve lots may not be altered. Household pets are allowed, leashed outdoors. Outside Saturday and Sunday open house hours, buyers enter with an agent, per the community access procedures.
We find you the right home in Units One, Two and Three at Olde Cypress by matching the street to your budget first, then watching every listing and owner conversation on the four streets. With no active listing on September 26, 2026, the right home is often the one that has not reached the market yet.
With 73.5 percent of homes homesteaded and many owners holding for years, a meaningful share of sales start as a conversation, and we bring you homes before they are listed when an owner is willing. A saved search on our site sends new listings on the four streets the day they appear and routes to Marc.
We negotiate a Units One, Two and Three purchase from the recorded sales on the same street, the listing's time on market, and the costs the seller has not disclosed. With a 24-month median of 93.16 percent of list, the room is real on a home that has waited and small on one priced to the street's evidence.
Before you offer, we show you every MLS and county sale on the street for four years, adjusted for size, view and condition. The deepest recent discounts, 81.72 and 89.23 percent of list on Treeline Drive, went to homes that had waited 124 and 142 days.
Missing club figures, an absent association budget or no elevation certificate belong in your price or your contingencies. On Wild Orchid Court and Olde Cypress Drive, where nothing has closed since mid-2025, a short appraisal is a reason to renegotiate. Marc Comisar and Jesse McGreevy negotiate every offer themselves. Selling first? See how we sell homes in Units One, Two and Three or call Jesse direct at (239) 898-6072; buying, call Marc at (239) 287-5873 or read how we represent buyers in Naples.
Buyer closing costs in Units One, Two and Three at Olde Cypress include, by Collier County custom, the owner's title policy and closing agent's fees, plus lender charges, the documentary stamp tax on the note at $0.35 per $100, the intangible tax at $0.002 per dollar, recording, inspections and prepaids.
On a $1,000,000 loan, Florida's documentary stamp tax on the promissory note at $0.35 per $100 is $3,500, and the nonrecurring intangible tax at $0.002 per dollar is $2,000, per the Florida Department of Revenue. A cash buyer pays neither.
In Collier County the buyer customarily chooses the closing agent and pays the owner's title policy, the opposite of the Lee County custom, and the contract controls. The premium is promulgated by the state, so it is the same at every title company, under Florida Administrative Code Rule 69O-186.003.
The master working capital contribution under Section 8.13 is collected at transfer and the contract decides who pays; taxes are prorated to the closing date.
Since August 17, 2024, buyers in Units One, Two and Three at Olde Cypress, as everywhere, sign a written agreement with their agent before touring, and that agreement states the agent's compensation, which is fully negotiable. Offers of compensation to buyer agents can no longer appear in the MLS, though a seller may still agree to pay part of it.
The agreement sets what we do, for how long and for what compensation, per the National Association of REALTORS guidance on written buyer agreements; read it before the first tour. More on us is on our about McGreevy and Comisar page.
Compensation is negotiable and not set by law. It may be paid by you, by the seller as a concession you negotiate, or by the listing brokerage where it offers to; the NAR settlement FAQ explains the rules. We tell you plainly how each approach changes your offer.
A Units One, Two and Three at Olde Cypress address carries assignment to Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026 to 2027, NCH Emergency Department Northeast about 2.4 road miles from the gate, I-75 Exit 111 about 1.6 miles away, and downtown Naples about 14.5 miles away.
All four streets are zoned to Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026 to 2027, per the Collier County Public Schools address lookup, all rated A in 2024, 2025 and 2026 on Florida Department of Education data as republished by the Naples Daily News.
Units One, Two and Three and Terramar at Olde Cypress are both detached golf neighborhoods behind the same gate, with the same club rule and no CDD. Units One, Two and Three is 185 homes on three plats priced from about $775,000 to $2,800,000; Terramar is 55 homes, every one on the golf course, in a tighter band.
Data updated: September 2026 (Southwest Florida MLS Matrix, retrieved 26 Sep 2026; Collier County Property Appraiser recorded sales file dated 29 Aug 2026)
| Question | Units One, Two and Three | Terramar at Olde Cypress |
|---|---|---|
| Homes and association | 185, Olde Cypress Homeowners' Association | 55, Terramar at Olde Cypress Homeowners Association |
| Streets | Olde Cypress Drive, Treeline Drive, Wild Orchid Court, Lone Pine Lane | Terramar Drive, Terramar Court |
| Backs onto golf | 141 of 185; preserve on Lone Pine Lane and east Treeline Drive | 55 of 55 |
| MLS closings and median, 48 months | 31, $1,450,000 | 11, $1,400,000 |
| MLS closings and median, 36 months | 21, $1,285,000 | 8, $1,137,000 (small sample) |
| Median sold-to-list, 48 months | 94.00 percent | 93.65 percent |
| Listings on September 26, 2026 | 0 active, 1 pending | 2 active |
| Median 2026 preliminary total tax | $7,532 | $7,334 |
| Effective 2012 map, wholly Zone AH | 70 of 185 | 7 of 55 |
| Assigned high school | Aubrey Rogers High | Aubrey Rogers High |
Choose Units One, Two and Three for range, from Lone Pine Lane near $1,000,000 to Wild Orchid Court, and more sales to price from. Choose Terramar for a golf view on every lot and less mapped Zone AH; see buying a home in Terramar at Olde Cypress.
Units One, Two and Three at Olde Cypress is the right place for a buyer who wants a detached home inside a private golf club without an equity stake, a choice of price levels under one association, the patience for a thin market, and costs confirmed in writing rather than published.
It fits if you want a preserve view, which Lone Pine Lane and east Treeline Drive offer and most of the gate does not, or the largest lots on Wild Orchid Court. It does not fit if you need every cost published before you tour, want a villa or short-term rental income, must buy this month, or need overnight parking for more than two cars outside the garage. Selling first? Request a Units One, Two and Three home valuation or call Jesse direct at (239) 898-6072; buying, call Marc at (239) 287-5873 or read how we represent buyers in Naples.
Your personalized Units One, Two and Three at Olde Cypress buyer consultation with McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008, starts with the contact form or a call to Marc Comisar at (239) 287-5873. We cover which street fits your budget, what it costs to own and how we would write your offer.
Call Marc Comisar at (239) 287-5873 or Jesse McGreevy direct at (239) 898-6072, email [email protected], or visit 24031 S Tamiami Trl #101, Bonita Springs, FL 34134. See how we represent buyers in Naples. Selling first? Start with a Units One, Two and Three home valuation.
A Units One, Two and Three at Olde Cypress specialist matters because the facts that decide a purchase live in documents rather than a listing feed: two streets shared with Biscayne Place, three plats that price differently, a club membership that comes by covenant, costs nobody publishes, and a flood map in transition with letters issued house by house.
Pricing a Wild Orchid Court home from a Lone Pine Lane median, confusing a Biscayne Place address with Unit One, quoting a club figure from a portal, or reading the preliminary flood map as effective. For the community-wide picture, read our Olde Cypress community guide and our guide to buying a home in Olde Cypress; for this association's full profile, the Units One, Two and Three at Olde Cypress guide.
Jesse McGreevy and Marc Comisar, Top 1% Real Estate Agents Nationally Since 2008, are the local real estate experts who represent Units One, Two and Three at Olde Cypress buyers: licensed Florida REALTORS with Domain Realty who run every search and negotiation themselves, Marc in the field and Jesse on the data.
Marc Comisar, a licensed Florida REALTOR and Broker Associate with Domain Realty, tours with you, runs the gate logistics and negotiates your offer. Reach him at (239) 287-5873 and on the Marc Comisar agent page.
Jesse McGreevy, a licensed Florida REALTOR and Sales Associate with Domain Realty and a co-founder of the brokerage, runs the comparable analysis and the association, club and flood documents. Reach him at (239) 898-6072 and on the Jesse McGreevy agent page.
See Sell Your Home in Units One, Two and Three at Olde Cypress for how we price, market and close, and request a free Units One, Two and Three home valuation if your current home is already on one of these streets. Call Jesse McGreevy direct at (239) 898-6072. Buying here? Read how we represent buyers in Naples or call Marc at (239) 287-5873.
These are the questions buyers ask before they write an offer in Units One, Two and Three at Olde Cypress, answered from the public record for a Collier County purchase in one short paragraph each, covering streets, prices, the club, costs, flood, rules and schools. Nothing here is legal, tax or insurance advice.
The Olde Cypress Homeowners' Association: 185 detached homes on three recorded plats, the largest of the nine neighborhoods inside the Olde Cypress gate in North Naples.
Olde Cypress Drive and west Treeline Drive in Unit One, east Treeline Drive and Wild Orchid Court in Unit Two, and Lone Pine Lane in Unit Three.
No. Wild Orchid Court and Lone Pine Lane are streets inside the one association, with no association of their own.
No. Eight Biscayne Place estate homes on Treeline Drive and Olde Cypress Drive belong to their own association; confirm the plat for any address.
None was active on September 26, 2026; one Treeline Drive home listed at $1,790,000 was pending with a contingency.
Fourteen MLS closings from $775,000 to $2,600,000, at a $1,250,000 median, in the 24 months to September 26, 2026.
Lone Pine Lane, with a 48-month MLS median of $1,000,000 on 9 closings, a small sample, and sales from $775,000 to $1,110,000.
Wild Orchid Court, with a 48-month MLS median of $1,929,111 on 6 closings and a high of $2,800,000 in June 2024.
Two-bedroom-plus-den to four-bedroom plans of about 2,100 to 2,550 square feet, backing onto golf or preserve.
The 24-month median was 93.16 percent of the final list; homes that waited longest sold for as little as 81.72 percent.
The association bills quarterly, including the master share, and publishes the amount only on its resident portal; the estoppel states it.
Possibly: Section 8.13 allows a Board-set working capital contribution at transfer, amount not published; the estoppel states it.
Social membership is, automatically, under Section 14.02 of the recorded 2019 master declaration. Golf membership is optional.
The club does not publish them. Get current figures in writing from the membership office at (239) 596-4797.
Non-equity and privately owned by a Stock family entity; owners hold no equity, vote or ownership interest.
No, confirmed by the county's CDD layer, the state's dissolved-district list and a 2025 Lone Pine Lane tax bill.
The 2026 preliminary median is $7,532 across the association: $8,438 in Unit One, $10,252 in Unit Two and $5,754 in Unit Three.
Because the assessment resets to market value after a sale; you do not inherit the seller's Save Our Homes cap.
Yes: on the effective 2012 map 70 footprints are wholly Zone AH, 69 partly and 46 Zone X; the preliminary map shows all 185 in Zone X.
Unit Two, with 30 footprints wholly and 35 partly in Zone AH on the effective map.
Only if your lender's determination puts your building in the Special Flood Hazard Area; the ZIP 34119 single-family median is $1,259 a year.
We found no report naming them for flood damage, and no NFIP claim in the block group is coded to Ian.
Most were finished between about 2000 and 2007; Unit Two has a few homes from 2011 to 2023.
60 of 61 in Unit One, 55 of 69 in Unit Two and 26 of 55 on Lone Pine Lane.
Yes, with a 60-day minimum, no more than four leases a year, a $100 fee, a $1,000 deposit and Board approval.
No. Vehicles may not be parked on Olde Cypress streets overnight, and no more than two cars in a driveway.
Laurel Oak Elementary, Oakridge Middle and Aubrey Rogers High for 2026 to 2027.
No. It is a condominium outside the gate with its own association and no club membership.
Yes, since August 17, 2024, and compensation in it is negotiable.
In Collier County the buyer customarily pays the owner's title policy and chooses the closing agent; the contract controls.
Units One, Two and Three for range and preserve lots; Terramar for golf on every lot.
Call Marc Comisar at (239) 287-5873 for a buyer consultation, or set up a saved search for the four streets on our site.
These are the questions owners ask when a sale and a Units One, Two and Three at Olde Cypress purchase have to happen together: timing, contingencies, homestead portability and moving within the gate. Confirm anything that affects your contract with your closing agent or attorney.
With no active listing on September 26, 2026, a buyer with a sale contingency may lose the one home that appears; selling first or bridge financing usually wins it.
You can, and a seller whose home has waited may accept it; a seller priced to the street's evidence often will not.
Often yes, within statutory limits, by filing with the new homestead application; the timing around January 1 matters.
Social membership follows the deed under the same covenant; ask the club about any golf category.
Start with a street-level valuation on our Units One, Two and Three home valuation page or call Jesse McGreevy direct at (239) 898-6072.
Every Units One, Two and Three at Olde Cypress figure on this page traces to a primary source below, retrieved September 2026 unless another date is shown, from the MLS, the county, the recorded declarations, the club, Florida Statutes, Freddie Mac, NAR and FEMA. No listing portal or competing brokerage is cited.
Market data and county records
The associations and their recorded documents
The Club at Olde Cypress
Florida statutes and buyer representation
Flood, storm and insurance
Schools and location
Our related pages
Every row below links the authority that publishes the document, so a Units One, Two and Three buyer sees the official, current version; we host nothing ourselves.
| Document | What it settles | Official authority |
|---|---|---|
| 2016 Olde Cypress Homeowners' Association declaration, OR 5260 PG 3502 | The association's own covenants for Units One, Two and Three | Olde Cypress Master Association, PDF |
| 2019 Amended and Restated Declaration for Olde Cypress, OR 5700 PG 1118 | Mandatory social membership (Section 14.02), no club equity (14.03), the working capital contribution (8.13), leasing, lakes and parking | Olde Cypress Master Association, certified PDF |
| 2013 leasing amendment, OR 4874 PG 3783 | The 60-day minimum, four leases a year, the $100 fee and the $1,000 deposit | Olde Cypress Master Association, PDF |
| Olde Cypress neighborhood site map | Where Units One, Two and Three, Biscayne Place and the gate house sit | Olde Cypress Master Association, image |
| Community access and gate procedures | How buyers are admitted at the gate | Olde Cypress Master Association, PDF |
| Collier County 2026 flood protection newsletter | The CRS Class 5 discount and floodplain rules | Collier County, PDF |
| Florida Statutes 720.401 | The pre-contract disclosure summary and the buyer's cancellation right | Florida Senate |
| Florida Statutes 720.30851 | Estoppel certificate contents and delivery | Florida Legislature |
| FEMA Map Service Center | The flood zone and any letter for your own address | FEMA |
Not public, and requested during your inspection period: the club's current dues and golf figures, from the membership office at (239) 596-4797; the association budget and quarterly assessment; the working capital contribution amount; the elevation certificate; and the estoppel.
Start your Units One, Two and Three at Olde Cypress home search with the Top 1% Real Estate Agents Nationally Since 2008 through the contact form on this page or a call to Marc Comisar at (239) 287-5873. With no active listing on September 26, 2026, the ready buyer gets the right home.
Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more at DomainRealtyGroup.com, and read about the partnership on our about McGreevy and Comisar page. Nothing on this page is legal, tax or insurance advice.
Market data from Southwest Florida MLS, pulled September 2026, and from the Collier County Property Appraiser, 2026 tax roll (preliminary) and recorded qualified sales, data file dated August 29, 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.
