Windstar on Naples Bay is a gated golf and boating community of 618 homes in 16 villages in Naples, FL 34112, with a Tom Fazio course and a marina on Naples Bay. Selling or buying? Talk to the #1 team in Southwest Florida since 2012, McGreevy and Comisar.
Updated October 2026 · Jesse McGreevy and Marc Comisar, Domain Realty
Jesse McGreevy and Marc Comisar help Windstar on Naples Bay owners sell at the right price with a quiet, well-run plan, and they help buyers pick the right village, the right fee stack and the right flood profile before an offer is written. Jesse has worked in Southwest Florida real estate since 2004, McGreevy and Comisar have been Top 1% Real Estate Agents Nationally Since 2008 and have over $900 million in personal sales, and McGreevy and Comisar are the #5 real estate team in Florida in the 2026 RealTrends rankings. Windstar on Naples Bay is a gated golf and boating community in Naples, Florida. Its 618 homes and condominiums sit in 16 villages on the east shore of Naples Bay off Bayshore Drive, ZIP 34112, according to the Florida Department of Revenue 2026 preliminary tax roll and the Collier County site address points layer (both read October 2026). If you searched “Windstar Naples,” this is the gated golf and boating community in East Naples, not the cruise line of the same name: a Tom Fazio golf course run by the Windstar Club, the 72-slip Southpointe Marina on the bay as the club describes it, and about 5 acres of master-owned beach property on Keewaydin Island reached by the association’s shuttle boat (master association, 2025 annual meeting outline, March 31, 2025).
If you’re searching for the best realtor for Windstar on Naples Bay, whether you’re ready to sell your Windstar 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.
McGreevy and Comisar are the #5 real estate team in Florida in the 2026 RealTrends rankings. Jesse McGreevy has been in the business since October 2004, he and Marc Comisar launched the team in 2008 (read the McGreevy and Comisar team story), and McGreevy and Comisar have been Top 1% Real Estate Agents Nationally Since 2008.
Windstar on Naples Bay market, last 12 months: We tracked 52 closed sales in Windstar on Naples Bay in the 12 months to October 13, 2026, $70,378,500 in volume, a $1,200,000 median and a top sale of $6,750,000 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026). Median days on market: 59 · Median sale-to-list ratio (sold price over final list price): 94.7%
Domain Realty, our brokerage, closed 658 transaction sides in Naples in the 60 months to October 5, 2026, $521.5 million in volume counted by side, per the Southwest Florida MLS pulled that day.
For luxury Windstar sellers: Premium marketing, cinematic video, drone, professional photography, qualified-buyer database, discretion and off-market capability when needed.
A Windstar listing is priced village by village, not community by community. In the same 12 months the Southwest Florida MLS recorded a $350,000 condominium sale in Windward Cay and a $6,750,000 estate sale on the Island at Southpointe, and the 16 villages behind those two numbers carry different associations, different flood zones, different tax rates and, in two cases, a different government. A single $1,200,000 median says very little about a Spinnaker Pointe carriage home or a Harrington Sound estate, so we build every Windstar price from the village’s own recent sales, the master assessment and the neighborhood association layer above it, the home’s elevation against the 2024 flood maps, and whether the buyer pool for that home is likely to want a Windstar Club membership. Buyers ask about each of those layers, and a listing that answers them up front tends to hold its price through inspection and appraisal.
Honors and recognition:
McGreevy and Comisar is a top-reviewed Windstar realtor, and every quote below is a five-star review on our Google Business Profile.
★★★★★ “If you’re looking for a Realtor in Naples (or nearby areas), Jesse is your guy. I referred a friend to him for a winter home search. He has great connections, sharp negotiating, and he found them an off-market brand new build. Highly recommend!” Verified Google review
★★★★★ “Jesse was accommodating and very informative … we can always depend on him if ever we have questions at any time, even Sundays. He is the best realtor we ever dealt with.” Verified Google review
Selling your Windstar on Naples Bay home? Get a free home valuation at McGreevy and Comisar’s home valuation page or Call Jesse direct at (239) 898-6072 (confidential conversations welcome for luxury listings).
Buying a home in Windstar on Naples Bay? Call Marc at (239) 287-5873 for a personalized buyer consultation, and see how McGreevy and Comisar represent buyers in Naples.
Contact McGreevy and Comisar:
Windstar on Naples Bay is a built-out, gated golf and boating community on the east shore of Naples Bay, with 16 villages, an optional equity club, a master association that owns a Keewaydin Island beach, and no Community Development District. The eight facts below change a buying or selling decision most, each with its source and date.
Windstar on Naples Bay (Windstar Naples, FL 34112) is a gated, built-out community of condominiums, villas and single-family homes between Bayshore Drive and Naples Bay, with an optional equity golf club, a marina on the bay and a private Keewaydin Island beach that the master association owns and runs for every resident.
That sentence holds what a first visit will not tell you: the master association runs the gates, roads, lakes and the Keewaydin beach; the Windstar Club is a separate, optional equity club; and each of the 16 villages has its own association. Windstar is not bundled, and owning a unit gives no right to use the club’s facilities (master association, recorded document compilation, Section 1.5). The governance and fee sections below explain each layer.
Windstar on Naples Bay is the gated golf and boating community in East Naples, not the cruise line of the same name. The main entrance is Windstar Boulevard at Bayshore Drive, where the private master road begins (Collier County site address points layer, queried October 2026). Collier County’s controlling zoning document for the community, Ordinance 93-23 (adopted May 11, 1993), places the Windstar PUD “one (1) mile south of U.S. 41 East and west of Bayshore Drive.” The same ordinance draws the edges a buyer will notice on a map: Haldeman Creek on the north, Bayshore Drive and the Harrington Sound land on the east, the Southpointe Yacht Club PUD on the south, and the City of Naples bayfront on the west, with Naples Bay beyond it (Collier County PUD layer, queried October 2026).
Two additions sit just outside those 1993 lines and are still inside the Windstar gates and the master association. To the south, the Southpointe Yacht Club PUD holds the marina basin, Marina Cove and Yacht Harbour Cove. To the north, along Haldeman Creek, the Regatta Landing tract was annexed into the master association by owner vote in 2013 and has its own gated entry from Lakeview Drive under the annexation agreement (master association, recorded document compilation, 2013 annexation, OR 4933 PG 1493).
Every one of the 52 Windstar closings we tracked in the 12 months to October 13, 2026 is a Naples address in ZIP 34112, the ZIP of every Windstar address point on the county layer (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026; the export’s city field reads Naples on every row and it carries no ZIP field). Unincorporated Windstar lies inside the boundary of the Bayshore Gateway Triangle Community Redevelopment Area and in Collier County Commission District 4 (both layers queried October 2026). The CRA matters to a Windstar buyer because the county’s redevelopment money is being spent on the Bayshore corridor right outside the gate, and that pipeline is covered further down this page.
Most of Windstar is unincorporated Collier County. Two bayfront villages, Admirals Watch and the Island at Southpointe, lie inside the City of Naples (Collier City Limits layer; FEMA political jurisdictions layer, both queried October 2026). Ordinance 93-23 anticipated this when it provided ingress and egress for “the sixteen residential units located in the City parcel west of the clubhouse,” which matches the 16 condominiums of Admirals Watch. The practical effect is on the tax bill and on which building department reviews permits, both covered in the fee and insurance sections.
The Windstar Club describes the community as sitting “directly across from Port Royal” on Naples Bay (Windstar Club, Bay Life, read October 2026), so buyers who also tour Port Royal are looking at the same water from the opposite shore, with very different products and price points on each side.
Distances from the Windstar Boulevard entrance are short: Naples Botanical Garden is about 0.7 miles and 2 minutes, Fifth Avenue South 3.1 miles and 7 minutes, and RSW 36.5 miles and 51 minutes by free-flow routing run on October 10, 2026 (OSRM public routing service); the drive-times section below has the full table.
Daily life in Windstar is organized around a staffed gatehouse, a short network of master roads, the golf course and the water. The gatehouse is a real cost line, not a decoration: gatehouse maintenance came in at $338,000 in 2024, the master association’s second-largest operating line after maintenance contracts (master association, 2025 annual meeting outline, March 31, 2025). The master association maintains four gates, which its 2025 reserve report names as Main, Lighthouse, Gulfstar and Regatta (same source).
Owners, club members and registered tenants enter with transponders; guests and vendors are admitted when the owner registers them, through the TekControl visitor system listed on the master association’s Documents page. If you are buying, ask the seller to register you, your inspector and your appraiser before each appointment. The master roads carry a 25 mph limit, and boats, trailers and RVs may not be parked overnight on master roads or common areas (Rules and Regulations approved May 15, 2018); the rules section below has the full list.
Every Windstar home is wired into a bulk Hotwire fiber contract that the master association signed for 10 years from March 1, 2025: 500/500 Mbps internet, two TV boxes and a 199-channel lineup, paid through the master assessment at $195 a quarter, $780 a year (master association, Communications page; Hotwire rate sheet for Windstar on Naples Bay, October 24, 2024; 2025 annual meeting outline). It is a cost every owner pays, not a free service: of the $880 increase in the master assessment from $3,250 in 2024 to $4,130 in 2025, $780 is the new Hotwire line (arithmetic on the 2025 annual meeting outline).
The social calendar has two layers. The Windstar Club runs concerts, speaker series, dining events and “clubs within a club” for members only (Windstar Club, Club Events and Culture, read October 2026). The master association layer is open to every resident: the Keewaydin Island beach, reached by the association’s shuttle boat on a trip of about 40 minutes (master association, Keewaydin Beach and Shuttle), and the Windstar Kayak Club at the master dock. Pools and village clubhouses belong to the neighborhood associations, so the village you pick shapes daily life as much as the gate does.
Buyers who come for the boating should judge it on the specific slip, the route to the Gulf and the clearance for their own boat rather than on any marketing line, and the boating section of this page lays those out village by village.
About 45.5% of Windstar homes carry a homestead exemption on the 2026 county roll, 281 of 618, a proxy for year-round ownership (homestead exemptions on the 2026 roll; Florida DOR 2026 preliminary tax roll, read October 2026; percentage is our arithmetic). Florida grants a homestead exemption only on a permanent residence, so the share is a fair stand-in for how many owners call Windstar home all year. It is not a perfect count: a home owned by a trust or a company, a recently bought home whose owner has not yet filed, and a seasonal owner who files in another state all fall outside it.
The share swings widely by village, and that swing tells a buyer a good deal about the feel of a building in August:
Village | Homestead homes on the 2026 roll | Share |
|---|---|---|
Admirals Watch | 12 of 16 | 75% |
Regatta Landing | 43 of 64 | 67% |
Harrington Sound | 17 of 27 | 63% |
Yacht Harbour Cove | 16 of 28 | 57% |
Clipper Cove | 19 of 35 | 54% |
Ketch Cay | 22 of 42 | 52% |
Island at Southpointe | 5 of 10 | 50% |
Leeward Cay | 8 of 16 | 50% |
Northstar | 8 of 16 | 50% |
Somerset at Windstar | 23 of 50 | 46% |
Spinnaker Pointe | 36 of 88 | 41% |
Marina Cove | 29 of 72 | 40% |
Spyglass Pointe | 4 of 10 | 40% |
Windward Cay | 14 of 48 | 29% |
Compass Point South | 20 of 72 | 28% |
Morningstar | 5 of 24 | 21% |
All of Windstar | 281 of 618 | 45.5% |
Source: Florida DOR 2026 preliminary tax roll, read October 2026; shares are arithmetic.
The pattern is consistent with product. The newest homes (Regatta Landing, built 2016 to 2021) and the largest ones (Admirals Watch, Harrington Sound) lead, while the older, smaller condominiums along Haldeman Creek Drive (Morningstar, Compass Point South) and Windward Cay sit at the low end, where second-home and seasonal ownership is more common. For a buyer who wants neighbors in July, the top half of that table is the place to start. For a buyer who wants a lock-and-leave winter home, the lower half usually means a quieter summer and more owners on the same calendar.
Windstar’s 16 villages split into 9 condominium villages with 428 units and 7 homeowner-association villages with 190 homes (DBPR condominium extract; Florida DOR 2026 preliminary roll). Price, product, association type and flood profile all move together, so the easiest way to narrow the search is by budget and by the kind of home you want to live in. Every price below is a closed sale in the 12 months to October 13, 2026 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026).
If you want | Start with | What the last 12 months show |
|---|---|---|
An entry condominium under $700,000 | Compass Point South, Spinnaker Pointe, Marina Cove, parts of Windward Cay | Compass Point South: 2 sales ($430,000 and $508,000), and a $503,500 median over 36 months (14 sales); Spinnaker Pointe: 5 sales, $525,000 to $905,000, and a $630,000 median over 24 months (11 sales); Marina Cove: 6 sales, $507,500 to $745,000, and a $646,000 median over 24 months (12 sales); Windward Cay: 4 sales, $350,000 to $1,075,000 |
An attached villa around $1.1 million | Somerset at Windstar, Leeward Cay | Somerset: 5 sales, $660,000 to $1,300,000, and a $1,095,000 median over 24 months (10 sales); Leeward Cay: 3 sales, $800,000 to $1,270,000 |
A newer coach home | Regatta Landing | 9 sales, $1,090,500 to $1,849,000, and a $1,310,000 median over 24 months (16 sales) |
A coach home on the marina basin | Yacht Harbour Cove | 5 sales, $1,200,000 to $2,250,000, and a $1,700,000 median over 36 months (11 sales) |
A detached courtyard or pool home | Ketch Cay, Clipper Cove, Spyglass Pointe | Ketch Cay: 3 sales, $1,375,000 to $1,750,000; Clipper Cove: 2 sales, $1,480,000 and $1,625,000; Spyglass Pointe one sale, at $1,775,000 |
An estate home | Harrington Sound, Island at Southpointe | Harrington Sound one sale, at $2,075,000; Island at Southpointe one sale, at $6,750,000 (both too thin to read as a market rate) |
A City of Naples luxury condominium with boat slips | Admirals Watch | 3 sales: $2,375,000, $2,935,000 and $3,625,000 |
A small, older condominium enclave | Northstar, Morningstar | Northstar two sales, $1,325,000 and $1,375,000; Morningstar no closed sale in the window |
The village sections further down this page give each village’s streets, build years, association, amenities and flood sample. In the condominium villages, the association’s budget, reserves and building inspections matter as much as the unit, so ask for them early.
If you are comparing agents before you choose a village, see how we rank the best real estate agents in Naples and what each one brings to a gated golf and boating community like Windstar.
Selling a Windstar home while you buy your next one? Start with a free, village-specific valuation at McGreevy and Comisar’s home valuation page, or Call Jesse direct at (239) 898-6072.
Buying in Windstar on Naples Bay? Call Marc at (239) 287-5873 to walk the villages that fit your budget, read how we help buyers find a home in Naples, and see how McGreevy and Comisar represent buyers from the first showing through closing.
We tracked 52 closed sales in Windstar on Naples Bay from October 13, 2025 to October 13, 2026, with a $1,200,000 median, $70,378,500 in volume and prices from $350,000 to $6,750,000 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026).
Data updated: October 2026
The table below is the headline for Windstar Naples real estate in that window. One of the 52 sales, a $905,000 Spinnaker Pointe closing on February 27, 2026, is a Sold Data Entry record (a sale entered into the MLS after it closed); it is a real recorded sale, so it counts in the 52, the median, the range and the volume, and it is left out of days on market and sale-to-list because it carries no days-on-market figure. Three other closings carry zero days on market and are left out of those two measures as well, so they rest on 48 of the 52 sales. Days on market is a median unless a sentence says average, and the sale-to-list ratio (sold price over final list price) is the sold price divided by the final list price, because the MLS export carries no original list price.
Measure | Windstar on Naples Bay, 12 months to October 13, 2026 |
|---|---|
Closed sales | 52 (51 standard closings and 1 Sold Data Entry record) |
Median sold price | $1,200,000 (an even count: the middle pair are $1,200,000 and $1,200,000) |
Range | $350,000 (Windward Cay) to $6,750,000 (Island at Southpointe) |
Sold volume | $70,378,500 |
Average sold price (secondary to the median) | $1,353,433 ($70,378,500 divided by 52) |
Villages with at least one sale | 15 of 16 (Morningstar had none) |
ZIP code | 34112 (county address points; the MLS export reads Naples on all 52 and carries no ZIP field) |
Median days on market | 59 days (average 73; the 48 sales with a days-on-market figure) |
Median sale-to-list ratio | 94.7% (average 94.5%; same 48 sales) |
Median price per square foot | $493 (all 52 sales, sold price over living area) |
Active listings | 15 active and 5 pending at the October 13, 2026 pull |
Against the prior 12 months | 50 sales and a $1,045,015 median then, so the median rose 14.8%; median days on market was 34 and sale-to-list 95.8% |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026. The average is our arithmetic.
The median and the average tell different stories, and the gap between them is worth a sentence. The median sits at $1,200,000 because the 52 sales cluster heavily between $1,000,000 and $1,500,000 and between $500,000 and $750,000. The average is pulled up to $1,353,433 by a handful of large sales, above all the $6,750,000 Island at Southpointe closing. For pricing a specific home, neither number is the right anchor; the village figures in the next table are.
Two record-keeping points explain why the MLS shows 15 village names while Windstar has 16 villages. Morningstar, a 24-unit condominium on Haldeman Creek Drive, simply had no closed sale in the window. And the MLS name “Southpointe Yacht Club” is the Island at Southpointe: the ten estate homes on Gulfstar Drive South carry the legal description “Southpointe Yacht Club Phase” on the county roll, and their association was formerly named The Island at Southpointe Yacht Club Residents’ Association (Florida DOR 2026 preliminary roll; Sunbiz, The Island at Southpointe Homeowners Association, Inc.). The same words also name the 1988 county PUD and, in the master declaration, the marina, which is a separate entity, Southpointe at Windstar Marina Association, Inc.
Every Windstar village with a sale in the window is listed below, with the thin ones marked. No village reached 10 closings in the window, and we never print a median for fewer than 10 sales, so each row gives the count and the range, with the sales themselves listed where there are five or fewer. Where a village has 10 or more sales over 24 or 36 months, that median is shown with its window named.
Village (name used in the MLS) | Sales | Median or sales listed | Low | High |
|---|---|---|---|---|
Regatta Landing (Regatta Landing) | 9 | no median in 12 months; 24 months: 16 sales, median $1,310,000 | $1,090,500 | $1,849,000 |
Marina Cove (Marina Cove) | 6 | no median in 12 months; 24 months: 12 sales, median $646,000 | $507,500 | $745,000 |
Somerset at Windstar (Somerset at Windstar) | 5 | $660,000, $1,100,000, $1,125,000, $1,300,000 and $1,300,000; 24 months: 10 sales, median $1,095,000 | $660,000 | $1,300,000 |
Spinnaker Pointe (Spinnaker Pointe) | 5 | $525,000, $630,000, $645,000, $660,000 and $905,000 (includes the Sold Data Entry record); 24 months: 11 sales, median $630,000 | $525,000 | $905,000 |
Yacht Harbour Cove (Yacht Harbour Cove) | 5 | $1,200,000, $1,300,000, $1,610,000, $1,700,000 and $2,250,000; 36 months: 11 sales, median $1,700,000 | $1,200,000 | $2,250,000 |
Windward Cay (Windward Cay) | 4 | $350,000, $665,000, $725,000 and $1,075,000 | $350,000 | $1,075,000 |
Admirals Watch (Admirals Watch) | 3 | $2,375,000, $2,935,000 and $3,625,000 | $2,375,000 | $3,625,000 |
Ketch Cay (Ketch Cay) | 3 | $1,375,000, $1,525,000 and $1,750,000 | $1,375,000 | $1,750,000 |
Leeward Cay (Leeward Cay) | 3 | $800,000, $1,137,000 and $1,270,000 | $800,000 | $1,270,000 |
Clipper Cove (Clipper Cove) | 2 | $1,480,000 and $1,625,000 | $1,480,000 | $1,625,000 |
Compass Point South (Compass Point South) | 2 | $430,000 and $508,000; 36 months: 14 sales, median $503,500 | $430,000 | $508,000 |
Northstar (Northstar Villas) | 2 | two sales, $1,325,000 and $1,375,000 (too thin to read as a market rate) | $1,325,000 | $1,375,000 |
Harrington Sound (Harrington Sound) | 1 | one sale, at $2,075,000 (thin) | ||
Island at Southpointe (Southpointe Yacht Club) | 1 | one sale, at $6,750,000 (thin) | ||
Spyglass Pointe (Spyglass Pointe) | 1 | one sale, at $1,775,000 (thin) | ||
Morningstar (no MLS name in the window) | 0 | no closed sale in the window |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026.
Read the table village by village, not top to bottom. Regatta Landing led the count with 9 closings, which fits a village of 64 newer homes with a young resale market. Marina Cove’s 6 sales sat in a tight band from $507,500 to $745,000, the narrowest spread of any village with more than three sales, which makes it the easiest Windstar village to price from comparables. Windward Cay ran the other way: four sales from $350,000 to $1,075,000, because its 48 units were built in phases from 1984 to 2004 and differ in size, floor and view. Yacht Harbour Cove’s five sales, all on the marina basin, ran from $1,200,000 to $2,250,000. At the top, the three Admirals Watch closings, from $2,375,000 to $3,625,000, show what a City of Naples bayfront condominium with a slip commands inside the Windstar gates.
For a seller, the lesson is that a Windstar price has to be built from the right village and the right product inside it. A Spinnaker Pointe carriage home and a Somerset villa are both “Windstar,” but over 24 months their medians were $465,000 apart ($630,000 against $1,095,000).
Grouping the 52 sales by product type gives a cleaner read of what each kind of home costs. The grouping below was made by McGreevy and Comisar from the MLS rows, using each village’s recorded form of ownership: detached single-family homes and attached villas are homeowner-association villages, and the rest are condominiums.
Segment | Villages | Sales | Median | Low to high | Volume |
|---|---|---|---|---|---|
Detached single-family (HOA) | Ketch Cay, Clipper Cove, Harrington Sound, Spyglass Pointe, Island at Southpointe | 8 | no median (fewer than 10 sales); 24 months: $1,600,000 on 22 sales | $1,375,000 to $6,750,000 | $18,355,000 |
Attached villas (HOA) | Somerset at Windstar, Leeward Cay | 8 | no median (fewer than 10 sales); 24 months: $1,100,000 on 13 sales | $660,000 to $1,300,000 | $8,692,000 |
Condominiums | Regatta Landing, Marina Cove, Spinnaker Pointe, Yacht Harbour Cove, Windward Cay, Admirals Watch, Compass Point South, Northstar | 36 | $1,096,250 (even count: mean of $1,090,500 and $1,102,000) | $350,000 to $3,625,000 | $43,331,500 |
Total | 52 | $70,378,500 |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, grouped by McGreevy and Comisar from the MLS rows.
Condominiums closed at a median of $1,096,250 (36 sales); detached homes (8 sales) and attached villas (8 sales) were each too few for a 12-month median, and their 24-month medians were $1,600,000 (22 sales) and $1,100,000 (13 sales). Condominiums were about seven in ten of the market by count and well over half by volume, which reflects Windstar’s makeup: 428 of its 618 homes are condominium units (DBPR condominium extract; Florida DOR 2026 preliminary roll).
The condominium median hides a very wide range. It runs from the $350,000 Windward Cay sale to the $3,625,000 Admirals Watch sale, and it includes both the 1990s three-story buildings of Compass Point South and the 2016 to 2021 coach homes of Regatta Landing. A condominium buyer in Windstar is really choosing among five or six different markets, each with its own association budget, building age and inspection schedule. The villa segment is the opposite: two homeowner associations, homes of similar age, and an eight-sale spread from $660,000 to $1,300,000 in the last 12 months.
Six of the 52 Windstar sales closed at $2,000,000 or more in the 12 months to October 13, 2026 (Southwest Florida MLS): three in Admirals Watch, one in Harrington Sound, one on the Island at Southpointe and one in Yacht Harbour Cove. The full spread by price band looks like this:
Price band | Closed sales |
|---|---|
Under $500,000 | 2 |
$500,000 to $749,999 | 14 |
$750,000 to $999,999 | 2 |
$1,000,000 to $1,499,999 | 18 |
$1,500,000 to $1,999,999 | 10 |
$2,000,000 to $2,999,999 | 4 |
$3,000,000 and up | 2 |
Total | 52 |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026.
The band counts show a market with two bodies and a thin middle. Fourteen sales landed between $500,000 and $749,999, mostly the entry condominiums of Marina Cove, Spinnaker Pointe and Windward Cay. Eighteen landed between $1,000,000 and $1,499,999, mostly Regatta Landing, Somerset, Leeward Cay, Northstar and Yacht Harbour Cove. Only two sales fell between $750,000 and $999,999: the $905,000 Spinnaker Pointe record and an $800,000 Leeward Cay villa. A buyer whose budget sits in that gap should expect few direct comparables and will usually weigh the upper end of the entry condominiums against the lower end of the villa and coach-home villages.
The six sales at $2,000,000 or more:
Village | Sale price | Closed |
|---|---|---|
Island at Southpointe | $6,750,000 | June 16, 2026 |
Admirals Watch | $3,625,000 | November 7, 2025 |
Admirals Watch | $2,935,000 | November 14, 2025 |
Admirals Watch | $2,375,000 | January 21, 2026 |
Yacht Harbour Cove | $2,250,000 | June 30, 2026 |
Harrington Sound | $2,075,000 | January 28, 2026 |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026.
The $6,750,000 Island at Southpointe sale is the top of the window and the only Windstar sale above $3,625,000. The $3,625,000 Admirals Watch sale is the highest condominium price in the window. Four of the six, the Island at Southpointe sale and the three Admirals Watch sales, are in the two Windstar villages that lie inside the City of Naples, which is where Windstar’s top end concentrated in this window.
Closings by month show when the 52 sales recorded, as counts only:
Month | Closings |
|---|---|
Oct 2025 (from Oct 13) | 3 |
Nov 2025 | 4 |
Dec 2025 | 7 |
Jan 2026 | 4 |
Feb 2026 | 4 |
Mar 2026 | 4 |
Apr 2026 | 8 |
May 2026 | 4 |
Jun 2026 | 10 |
Jul 2026 | 2 |
Aug 2026 | 2 |
Sep 2026 | 0 |
Oct 2026 (to Oct 13) | 0 |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026.
The busiest months in this window were June 2026 (10 closings), April 2026 (8) and December 2025 (7). Closing dates trail contract dates, so a June closing usually reflects a contract written in spring. The export records no closing after August 25, 2026. One year of data is not enough to call a seasonal pattern, and we do not read it as one.
The median number of days a Windstar listing was on the market in the 12 months to October 13, 2026 was 59 (Southwest Florida MLS), up from 34 in the prior 12 months. It is measured on the 48 closings that carry a days-on-market figure and both prices, because the Sold Data Entry record carries no days-on-market figure and three other closings are recorded at zero days.
The median sale-to-list ratio over the same 48 closings was 94.7%, against 95.8% in the prior 12 months, which shows how close Windstar sellers came to their final asking price.
The median sold price per square foot of living area was $493 (the prior 12 months: $455), and the median final list price was $1,249,500. Because Windstar’s homes run from compact condominiums to large estates, a single community-wide price per square foot is a rough guide at best; the village figures are the ones to use for a specific home.
Windstar had 15 homes listed for sale at the October 13, 2026 MLS pull, at a median list price of $659,000 (from $425,000 to $2,795,000), with 5 more under contract. Months of supply, which is active listings divided by the monthly closing pace of the last 12 months (52 closings, or 4.3 a month), was 3.5. All 15 listings are condominiums, 8 of them in Marina Cove, and none is a villa or a detached home. Inventory changes week to week in a community this size, so a buyer should ask for a current active and pending list for the villages on their short list, and a seller should ask what is competing with their home in the same village and price band before setting a price.
For a Windstar owner, the most useful next step is a valuation built from the village’s own sales, the association layer above it and the home’s flood and elevation record, not from the community median. Get one at McGreevy and Comisar’s home valuation page, or Call Jesse direct at (239) 898-6072.
Windstar on Naples Bay began as the 1981 “Fisherman’s Cove” PUD on 320.6 acres along Naples Bay and Haldeman Creek, was renamed Windstar by its developer in 1982, and was rewritten in 1993 to a 549-unit plan that Collier County now lists as built out, with Southpointe added in 1988 and Regatta Landing annexed in 2013.
The history matters to a buyer for practical reasons. It explains why Windstar’s villages range from 1984 condominiums to 2021 coach homes, why four different zoning regimes sit inside one gate, why two villages pay City of Naples taxes, and why the master association, the club and the marina are separate legal entities. Every step below comes from a recorded county ordinance, a Florida corporate filing or the county tax roll, cited where it is used.
The land that became Windstar was first rezoned for golf. Ordinance 82-54 carries forward development conditions agreed “during the rezoning of Fisherman’s Cove to Golf Course,” attached as an exhibit dated June 5, 1980, and the 1981 PUD includes a Height Limitation Agreement dated September 16, 1980 that held buildings to no more than three habitable floors over one parking level and 40 feet above finished grade (Ordinance 82-54, July 13, 1982; Ordinance 81-40, August 25, 1981).
Ordinance 81-40, adopted August 25, 1981, created the “Fisherman’s Cove” PUD for the landowner and petitioner, Whispering Pines, Inc. of Naples (Sunbiz, Whispering Pines, Inc.). It rezoned 320.60 acres from multifamily and general commercial districts to a planned unit development allowing 749 multifamily units on 98.48 acres plus a 212.12-acre golf course tract. The ordinance describes a low, wet site: uplands falling from about six feet to two feet above sea level toward Naples Bay and Haldeman Creek, soils that were about 21% mangrove swamp, and a water management plan built on 16 interconnected lakes. Those lakes are still the backbone of Windstar’s drainage and the reason so many homes look onto water even when they are nowhere near the bay.
The Windstar name arrived a year later. Ordinance 82-54, adopted July 13, 1982, re-titled the PUD “Windstar” for Windstar Development Company, kept the 749-unit cap, and added a golf clubhouse, parking, tennis and a pro shop as permitted uses. Windstar Development Company had been filed on December 2, 1981 as Spyglass of Naples, Inc. and took the Windstar Development Company name on March 12, 1982 (Sunbiz, WDC Corp. record; Sunbiz, WDC Corp. name history). Fisherman’s Cove survives today only as an alternate name in the county’s PUD record (Collier County PUD layer); it is not a neighborhood a buyer can find on a map.
The first decade built the course, the clubhouse, the master association and the first five villages. Windstar Club, Incorporated was filed as a not-for-profit corporation on December 1, 1983 at 1700 Windstar Boulevard (Sunbiz, Windstar Club, Incorporated). The club’s own history dates the Tom Fazio design to 1983; the clubhouse opened in 1986 (Windstar Club, Our Club, read October 2026). The same history lists Greg Norman and Andy Bean as touring professionals representing the club in the 1980s, as the club tells its own story. Today the club describes itself as an equity, member-owned club that accepts non-resident members.
The master association came next. It was filed on March 9, 1984 as The Windstar Condominium Master Association, Inc. (Sunbiz, Windstar on Naples Bay Master Association, Inc.), and the original Master Declaration of Covenants, Conditions and Restrictions is recorded at Official Records Book 1075, Pages 736 to 755, the instrument Ordinance 93-23 later cites as the developer’s master declaration (master association, recorded document compilation). On May 6, 1985, Windstar Development Company filed the WINDSTAR and WINDSTAR ON NAPLES BAY service marks for “planning and laying out of residential communities for others” (Justia Trademarks, Windstar Development Company marks), which is where the full community name comes from.
Homes followed the course. The county roll dates the first Windstar homes to 1984, in the first Windward Cay buildings (Florida Statewide Cadastral, DOR 2026 roll, queried October 2026). Morningstar and Northstar followed from 1986 to 1988, Leeward Cay from 1987 to 1989 and Somerset at Windstar in 1989 and 1990. By the end of 1990, 120 homes had been delivered: Windward Cay 14, Morningstar 24, Northstar 16, Leeward Cay 16 and Somerset 50 (same roll). The roll records no Windstar deliveries in 1991.
That first wave explains a good deal about today’s market. The 1980s villages sit along Haldeman Creek Drive and Yacht Harbor Drive, they are among the smallest and oldest homes in Windstar, and several of them (Morningstar, Windward Cay) have the lowest year-round ownership shares on the 2026 roll. They also carry the questions an older building raises: roof and window age, plumbing and electrical updates, and, for the condominiums, the building inspections and reserve rules covered elsewhere on this page.
The plan that governs Windstar today is Ordinance 93-23, adopted May 11, 1993. Its petitioner and owner of record was WS Realty, Inc., an Ohio corporation registered in Florida in May 1991, whose Sunbiz mailing address was in care of a bank in Columbus, Ohio (Sunbiz, WS Realty, Inc.). The PUD document was prepared in October 1992 “for WS Realty, Inc., Windstar on Naples Bay, 4090 Haldeman Creek Drive.”
The rewrite changed Windstar’s shape in four ways that still show on the ground:
Windstar Development Company changed its name to WDC Corp. on February 1, 1993 and was administratively dissolved in 1995 (Sunbiz, WDC Corp. name history). The Windstar PUD has not been rezoned since Ordinance 93-23 in 1993, and the county lists it as built out (Collier County PUD layer, queried October 2026).
The second building wave ran from 1992 to 2004 and produced most of Windstar’s homes, from Compass Point South (1992 to 1995) and Spinnaker Pointe (1994 to 1995) to Marina Cove (1997 to 1999) and the last Windward Cay buildings (2003 to 2004), per the Florida Statewide Cadastral, DOR 2026 roll; the village table further down gives every village’s build years.
Not all of those villages sit inside the 1993 PUD. Harrington Sound is on county RMF-6 land east of the course, Admirals Watch and the Island at Southpointe are on City of Naples land, and Marina Cove and Yacht Harbour Cove are in the Southpointe PUD. By zoning regime, Windstar’s 618 homes break down as 401 in the Windstar PUD, 100 in the Southpointe Yacht Club PUD, 26 in the City of Naples and 91 on county RMF-6 land (Collier County zoning layer; Florida DOR 2026 preliminary roll). For a buyer, the zoning regime decides which ordinance governs a rebuild, and the jurisdiction decides which building department issues the permit.
Windstar’s marina basin is older than Windstar itself. Ordinance 88-82, adopted October 25, 1988, created the Southpointe Yacht Club PUD on 16.51 acres just south of Windstar, on the former site of the Jackson Fish Camp, a fish camp and marina built around 1950 that sold fuel and bait and rented dockage near Gordon Pass, and that had later been approved as a mobile home park. The ordinance approved 96 multifamily units and a yacht club using the existing 72-slip boat basin, with a clubhouse on an island. The petitioner was Marina South, Inc., a company later renamed Sudamerina Corp. (Sunbiz, Sudamerina Corp.).
Today that land holds three parts of Windstar. Southpointe Marina, which the club describes as 72 slips taking yachts up to 70 feet (Windstar Club, Bay Life), is run by its own association; Marina Cove’s 72 coach homes and community center sit beside it (Marina Cove page); and Yacht Harbour Cove’s 28 coach homes line the basin itself (Yacht Harbour Cove page). The 2026 county roll carries 73 slip parcels at the marina (Florida DOR 2026 preliminary roll), one more than the club and the 1988 PUD describe; both records are real, and a slip buyer should rely on the recorded description of the specific slip. Collier County lists the Southpointe Yacht Club PUD, like the Windstar PUD, as built out (Collier County PUD layer).
The old fish camp is also why the name “Southpointe Yacht Club” turns up in three places: as the 1988 PUD, as the master declaration’s word for the marina, and as the MLS name for the ten Island at Southpointe homes, whose recorded legal description is “Southpointe Yacht Club Phase.” The market section above explains how to read the MLS name.
Windstar’s last chapter took two tries. In 2005, a petition sought to add a 20.52-acre tract north of the golf course, then known as the Fisherman’s Village tract, to the Windstar PUD with up to 137 new units, which would have raised the PUD total to 584 (BCC agenda, October 10, 2006, Item 8B). The petition was continued several times while Windstar owners voted and access from Lakeview Drive was debated (BCC agenda, April 10, 2007, Item 8A), and on April 10, 2007 it was continued indefinitely at the petitioner’s request (BCC backup documents, April 10, 2007). It was never adopted. County staff had placed that tract inside the Coastal High Hazard Area in 2006 (same 2006 agenda).
Between the two attempts, the master association took its current form. On November 4, 2009 it adopted its present name, Windstar on Naples Bay Master Association, Inc., having been renamed once before, in 1998, as The Windstar Master Association, Inc. (Sunbiz, Windstar on Naples Bay Master Association, Inc.). The Second Amended and Restated Master Declaration, recorded at Official Records Book 4512, Page 2575 on November 24, 2009, is the governing master declaration today, and in it the association acts as successor in interest to the original declarant (master association, recorded document compilation).
The second try did not rezone anything. Instead, Windstar owners annexed the land privately. At a special meeting on June 14, 2013, a two-thirds owner vote approved an Agreement Regarding Annexation and Supplemental Declaration with WSC Naples, LLC (Sunbiz, WSC Naples, LLC), recorded at OR 4933, PG 1493 (master association, recorded document compilation). The agreement set the terms that still shape Regatta Landing:
The master assessment at the time of the vote was $2,212 a year (same compilation). Against the $4,130 rate for 2025 (2025 annual meeting outline), that is a useful reminder for any buyer that master fees move over time.
The docks took longer than the homes. The county Planning Commission denied a 42-slip dock extension on Haldeman Creek on June 19, 2014 (BCC agenda, December 9, 2014, Item 9A), and a reduced 26-slip facility went to the Board of County Commissioners on its consent agenda on January 12, 2016 (BCC agenda, January 12, 2016, Item 16A29). The county’s address layer shows 27 wet-slip points at the dock today (Collier County site address points layer).
The Regatta Landing condominium declaration names Standard Pacific of Florida as developer (Regatta Landing Amended and Restated Declaration of Condominium), the county’s site plan called the project “Haldeman’s Landing,” and the county roll dates its 64 homes from 2016 to 2021 (Florida Statewide Cadastral, DOR 2026 roll). Those were the last new homes built in Windstar. Because the tract was annexed rather than rezoned, Regatta Landing sits on county RMF-6(3) land outside the 1993 PUD while paying the master assessment and using the master amenities like every other village.
That is the whole arc: a golf-course rezoning in 1980, a 749-unit plan in 1981, the Windstar name in 1982, a smaller and more varied plan in 1993, the Southpointe marina added beside it in 1988, and a final 64 homes annexed in 2013 and finished in 2021. A buyer looking at any Windstar home can place it on that timeline from its year built, and the timeline tells you which documents, which zoning and which building generation you are dealing with.
Windstar on Naples Bay is built out: Collier County lists both its PUDs (Windstar, Ordinance 93-23, and Southpointe Yacht Club, Ordinance 88-82) as built out, the last new homes were Regatta Landing’s in 2021, and the community’s 618 homes sit under four zoning regimes, from county PUDs to City of Naples land.
That short answer matters for buyers and sellers in different ways. A buyer in Windstar is choosing among resale homes only: there is no developer inventory inside the gates, no lot to buy and no builder price sheet to compare against. A seller is competing with other Windstar resales in the same village and with nothing new being built behind the guardhouse. The Collier County PUD layer records the Windstar PUD (petition R-81-8, Ordinance 93-23, also known as “Fisherman’s Cove”) and the Southpointe Yacht Club PUD (Ordinance 88-82) with the status “BUILT OUT”, read on October 10, 2026. The Florida Department of Revenue 2026 preliminary roll for Collier County dates the first Windstar homes to 1984 (Windward Cay) and the last new village homes to 2021 (Regatta Landing).
The plan on paper is older and larger than what was built. The 1993 controlling ordinance, Ordinance 93-23, adopted May 11, 1993 on the petition of WS Realty, Inc., covers 320.6 acres and caps the PUD at 549 dwelling units, a density of 1.71 units per acre. Not every Windstar home sits inside that PUD, though. The community grew by adding land on either side of it: the 16.51-acre Southpointe Yacht Club PUD on the old Jackson Fish Camp site to the south, approved by Ordinance 88-82 on October 25, 1988 with 96 multifamily units and the existing 72-slip basin; the Harrington Sound estates on county RMF-6 land; the two bayfront villages inside the City of Naples; and the Regatta Landing tract on Haldeman Creek, annexed into the master association in 2013. The Windstar on Naples Bay Master Association’s recorded document compilation, posted January 24, 2024, carries the 2009 master declaration and the 2013 annexation that tie all of these pieces under one master association.
The Windstar PUD itself is 320.6 acres under Ordinance 93-23. The add-ons are named here by record, not summed into a new acreage total: the 16.51-acre Southpointe Yacht Club PUD, the annexed Regatta Landing tract, the City of Naples bayfront parcels and about 5 acres of master-owned land on Keewaydin Island (county parcels of 2.68 and 2.74 acres in the county parcel layer, read October 10, 2026). Marketing material sometimes quotes a larger acreage for Windstar; the recorded figure for the PUD is the ordinance’s 320.6 acres.
Windstar’s 618 homes fall under four separate zoning regimes. We counted them village by village from the Collier County zoning layer and the Florida DOR 2026 preliminary roll, both read October 10, 2026, and the four totals add back to 618.
Regime | Villages | Homes | Source |
|---|---|---|---|
Windstar PUD, Ordinance 93-23 (county) | Windward Cay, Leeward Cay, Somerset at Windstar, Morningstar, Northstar, Compass Point South, Spinnaker Pointe, Ketch Cay, Spyglass Pointe, Clipper Cove | 401 | Zoning layer_view/FeatureServer/1); DOR 2026 roll |
Southpointe Yacht Club PUD, Ordinance 88-82 (county) | Marina Cove, Yacht Harbour Cove | 100 | Zoning layer_view/FeatureServer/1); DOR 2026 roll |
City of Naples | Admirals Watch, Island at Southpointe | 26 | City limits layer; DOR 2026 roll |
County RMF-6 and RMF-6(3) | Harrington Sound (RMF-6); Regatta Landing (RMF-6(3)) | 91 | Zoning layer_view/FeatureServer/1); DOR 2026 roll |
Total | 16 villages | 618 |
Why this matters in practice: zoning regime decides who you call about a fence, a pool cage or a rebuild, and it lines up with the property tax code on the bill. The ten villages inside the Windstar PUD and the two inside the Southpointe PUD are governed, for land use, by their PUD documents and the Collier Land Development Code’s PUD rules. Harrington Sound and Regatta Landing sit on conventional county multifamily zoning, which is why Regatta Landing’s dock and site plan went through ordinary county petitions in the 2010s rather than a PUD amendment. Admirals Watch and the Island at Southpointe answer to the City of Naples for zoning, building permits and floodplain administration. Every one of the 618 homes still answers to the master association’s declaration and to its own village association, whatever the zoning map says.
The county’s Future Land Use layer places Windstar in the Urban Coastal Fringe Subdistrict, the coastal designation that limits density on redevelopment. The county zoning exception layer also shows two Special Treatment overlay areas inside the PUD, read October 10, 2026.
Windstar was not built in one push. The DOR 2026 roll’s year-built field shows three waves and a final annexation: the 1980s Windstar Development Company villages (120 homes delivered by 1990, starting with Windward Cay in 1984), the 1992 to 2004 wave that filled in the 1993 plan with condominiums, carriage homes, single-family enclaves and the Southpointe and City of Naples bayfront product, and Regatta Landing’s 64 coach homes from 2016 to 2021. The village table below lists each village’s build years.
The practical takeaway for buyers is that building age inside Windstar runs from early 1980s condominiums to coach homes built after 2015. Building codes, flood elevations, roof ages and condominium reserve rules differ sharply across that span, so two homes a few hundred yards apart can carry very different insurance, inspection and association histories.
No new residential construction is left inside Windstar’s gates. Both PUDs carry the county’s “BUILT OUT” status in the Collier PUD layer, and the DOR 2026 roll shows no vacant residential lots inside the villages: the parcels coded as vacant are common tracts held by the associations, read October 10, 2026. The Windstar PUD has not been rezoned since Ordinance 93-23 in 1993; the county zoning layer_view/FeatureServer/1) still carries that ordinance as the controlling action, and a Collier Clerk legal notice search for “Windstar” returned no notices on October 10, 2026.
The permits active inside the gates in 2026 belong to the Windstar Club, not to any home builder. The county CityView projects layer lists a clubhouse expansion site plan amendment (PL20210001972) and a fitness center site plan amendment (PL20240013453) for the club, read October 10, 2026. The club describes the new fitness center as due in 2026; that is the club’s project, paid for by club members, and it adds no homes.
Change at the home level comes through rebuilds, one parcel at a time. The DOR 2026 roll shows Harrington Sound homes built as late as 2009 and one Island at Southpointe home built in 2012, long after their neighbors. The master association’s Architectural Review Committee reported in the 2025 Committee Reports Binder that during 2024 to 2025 it reviewed “the Windstar PUD to confirm that minimum building standards were in place for potential demo/new construction”. For an owner thinking about a teardown in a single-family village, that tells you two things: the master association expects the question, and the PUD’s development standards, the village association’s rules and the master Design Guidelines all apply before a county permit is pulled.
For sellers, a built-out community is a quiet advantage. There is no builder down the street with incentives and a model home pulling buyers away from resales, and every comparable sale a buyer sees is another resale inside the same gates.
Windstar on Naples Bay holds 618 homes in 16 villages, and we tracked 52 closed sales there with a $1,200,000 median in the 12 months to October 13, 2026 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026). In a built-out community, every sale is a resale, and the village, the association layer and the flood map move the price as much as the floor plan does.
Jesse McGreevy and Marc Comisar are the #5 real estate team in Florida in the 2026 RealTrends rankings, Top 1% Real Estate Agents Nationally Since 2008 and the #1 team in Southwest Florida since 2012, with over $900 million in personal sales.
If you own in Windstar, start with a free home valuation for your Windstar home, or call Jesse direct at (239) 898-6072. If you are buying, call Marc at (239) 287-5873 or read how we guide Naples buyers through a purchase before you tour.
Our Windstar on Naples Bay guides go deeper: selling a home in Windstar on Naples Bay, what your Windstar on Naples Bay home is worth and buying a home in Windstar on Naples Bay.
Windstar on Naples Bay is governed by Windstar on Naples Bay Master Association, Inc., a Chapter 720 homeowners association that every owner belongs to; each of the 16 villages adds its own condominium or homeowners association, and the Windstar Club and the marina are separate, optional “Recreational Associations” that no owner joins by buying a home.
That layered structure is the single most important thing to understand before you buy in Windstar. It decides who sends you a bill, who approves your lease or your new front door, who insures the roof over your head and who issues the estoppel certificate at closing. It also explains why two Windstar homes at the same price can carry very different monthly costs: the master assessment is the same for every home, but the village layer underneath it is not.
Identity. The master association is Windstar on Naples Bay Master Association, Inc., a Florida not-for-profit corporation, Sunbiz document N01881, filed March 9, 1984 as The Windstar Condominium Master Association, Inc. It was renamed The Windstar Master Association, Inc. by an amendment filed November 10, 1998, and took its current name with amended and restated articles filed November 4, 2009. Its principal office is 1700 Windstar Blvd, Naples, FL 34112, read on Sunbiz October 10, 2026.
Governing documents. The current base document is the Second Amended and Restated Master Declaration of Covenants, Conditions and Restrictions for Windstar, recorded November 24, 2009 at Official Records Book 4512, Page 2575, posted by the association with its articles, bylaws and amendments in the master association’s recorded document compilation (posted January 24, 2024). Three recorded amendments follow it:
The original Master Declaration sits at OR Book 1075, Pages 736 to 755, and is now superseded by the 2009 restatement.
Who belongs and how votes and assessments work. Section 1.3 of the declaration makes “All Unit Owners, Recreational Associations and Neighborhood Associations located within the Property” members of the association, which operates under Chapters 720 and 617 of the Florida Statutes. Article 2 gives one vote per Unit, and a “Unit” includes every condominium dwelling and every detached or attached home. Article 5 assigns each Unit “one assessment unit”, so a 1,400 square foot Compass Point South condominium and a bayfront estate pay the same master assessment. The declaration gives the association lien rights for unpaid assessments, with the first-mortgagee safe harbor set at the lesser of 12 months of assessments or 1% of the original mortgage debt (recorded compilation).
Board and meetings. Bylaw 4.1 sets a nine-director board with three-year staggered terms. The 2026 Election Meeting Packet, dated March 6, 2026, set the 2026 election meeting for March 27 and the annual meeting for March 30, with a 33% quorum for the annual meeting. The association’s committees are listed on its committees page: a permanent Architectural Review Committee and Finance Committee, plus advisory committees that the 2025 Committee Reports Binder shows reporting on Keewaydin, Building and Grounds and the Lakes.
Management. The master association is self-managed from 1700 Windstar Blvd, per its Property Management page, read October 10, 2026. Its 2022 lease application form routes applications through Ability Management. The association’s documents page is where owners find the declaration, rules, design guidelines and forms.
Developer turnover. The 2009 restated declaration was made by the association itself, which reserves easements “as successor in interest to the Declarant” (recorded compilation). By 2009, then, the association itself stood in the declarant’s place; the exact date the developer handed over control is not stated in the association’s posted documents.
What the master association runs. In practice the master association owns and pays for the things every Windstar household shares: the gatehouse and the four master gates (Main, Lighthouse, Gulfstar and Regatta), the master roads, entrance features, walls and sidewalks, the lakes and mangroves, the Windstar dock, the Keewaydin Island beach property and its shuttle, and the bulk internet and television contract. Those lines come from the 2025 Annual Meeting outline dated March 31, 2025, and the fee stack below shows what they cost per home.
Below the master association sits a second layer: one association per village. Nine villages are condominiums under Chapter 718 of the Florida Statutes (ten recorded condominium declarations, because Yacht Harbour Cove has two phases under one association) with 428 units, and seven are homeowners associations under Chapter 720 with 190 homes, per the DBPR condominium extract and the DOR 2026 roll, read October 10, 2026.
Village | Regime | Association of record | Manager where published |
|---|---|---|---|
Regatta Landing | Condominium (Ch. 718) | Regatta Landing Condominum [sic] Association, Inc., Sunbiz N15000008357; DBPR MA71254 | Paramount Property Management of Naples (Regatta Landing site) |
Marina Cove | Condominium (Ch. 718) | Marina Cove Condo Assn., Inc., DBPR MA00022297 | not posted |
Spinnaker Pointe | Condominium (Ch. 718) | Spinnaker Pointe at Windstar Condo Assoc Inc., DBPR MA00021054 (Sunbiz N93000001338) | not posted |
Yacht Harbour Cove | Condominium (Ch. 718), two declarations | Yacht Harbour Cove at Windstar Condominium Association, Inc. (Sunbiz N94000004128); DBPR MA00021430 for both phases | not posted |
Windward Cay | Condominium (Ch. 718) | The Windstar Condominium Section One Association, Inc., Sunbiz N01880; DBPR MA00000378 | Resort Management |
Compass Point South | Condominium (Ch. 718) | Compass Point at Windstar Condo Assn., Inc., DBPR MA00008950 (Sunbiz N13709) | Resort Management |
Admirals Watch | Condominium (Ch. 718) | Admiral’s Watch at Windstar Condominium Association, Inc. (Sunbiz N94000005983); DBPR MA00021623 | Ability Management |
Northstar | Condominium (Ch. 718) | Northstar Condominium Association, Inc. (Sunbiz N14971); DBPR MA00014120 | Ability Management |
Morningstar | Condominium (Ch. 718) | The Naples Morningstar Condominium Association, Inc. (Sunbiz N17397); DBPR MA00007791 | Resort Management |
Somerset at Windstar | HOA (Ch. 720) | Somerset at Windstar Homeowners Association, Inc., Sunbiz N30205 | Newell Property Management |
Ketch Cay | HOA (Ch. 720) | Ketch Cay at Windstar Residents’ Association, Inc., Sunbiz N94000005601 | Newell Property Management |
Clipper Cove | HOA (Ch. 720) | Clipper Cove Homeowner’s Association, Inc., Sunbiz N95000004387 | Ability Management |
Harrington Sound | HOA (Ch. 720) | Harrington Sound Resident’s Association, Inc., Sunbiz N36732 | not posted |
Spyglass Pointe | HOA (Ch. 720) | Spyglass Pointe Homeowners Association, Inc., Sunbiz N95000004304 | Newell Property Management |
Island at Southpointe | HOA (Ch. 720) | The Island at Southpointe Homeowners Association, Inc., Sunbiz N37243 | not stated |
Leeward Cay | HOA (Ch. 720) | Leeward Cay at Windstar on Naples Bay Homeowners Association, Inc., Sunbiz N30204 | Ability Management |
Managers are drawn from the master association’s neighborhood pages, the village sites and the DBPR record; companies only, never individuals. Managers change, so a buyer should confirm the current one on the association’s own estoppel or resale package. One naming wrinkle at the south end: the ten Island at Southpointe homes belong to The Island at Southpointe Homeowners Association, Inc., while a separate entity, Southpointe Neighborhood Association, Inc., holds Southpointe common parcels on the county parcel layer, read October 10, 2026.
Section 1.4 of the master declaration states that “Most, but not all, of the Units within Windstar are members of a Neighborhood Association” (recorded compilation). Neighborhood covenants are supplemental: they can be stricter than the master documents, but they cannot override them. Section 5.5 lets the master board have a neighborhood association collect the master assessment on its behalf, with the owner still personally liable. Two villages publish that they do exactly this: the Regatta Landing declaration makes the condominium association the master’s collection agent and carries the master assessment inside its own budget, and the Compass Point South 2021 Q and A says the same for Compass Point. In those villages, one quarterly bill covers both layers.
For a condominium buyer, the village association is often the bigger decision than the master one. The condominium association insures and maintains the building structure, funds the building’s reserves and, for buildings of three or more habitable stories, carries Florida’s structural integrity reserve study and milestone inspection duties. For a buyer in one of the seven homeowners-association villages, the owner typically insures and maintains the house itself, and the village association handles common tracts, entry features and any shared pool. In every case, the village’s own declaration and rules govern the details.
The Windstar Club is not the master association, and owning a home in Windstar does not make you a member. The club is Windstar Club, Incorporated, Sunbiz N00119, filed December 1, 1983, with its office at 1700 Windstar Blvd. Today it describes itself on its Our Club page as “an equity, Member-owned golf and Country Club that accepts non-resident Members”, and it states plainly that “Residents within the gates are not required to be Members.”
The master declaration treats the club and the marina as “Recreational Associations”. Section 1.5 says “No Owner or occupant gains any right to enter or to use the facilities of a Recreational Association simply by virtue of ownership or occupancy of a Unit” (recorded compilation). The Regatta Landing declaration says the same thing at the village level: membership in the club is not mandatory and is not a condition of buying a unit. Windstar is not bundled.
The club is a substantial landowner inside the gates. The county parcel layer shows 129.48 acres of club-owned land across four county parcels (118.88, 8.72, 1.47 and 0.41 acres), read October 10, 2026: the golf course, the clubhouse site and supporting tracts. A separate charity, the Windstar Club Charitable Foundation, Inc. (Sunbiz N16000010238), is its own corporation.
Two links tie the club to the master association. First, the master declaration protects the course: owners near it accept an easement for errant golf balls, maintenance noise and course chemical use, and the master association may not realign common areas in a way that harms club drainage. Second, Bylaw 8.4, as amended in December 2023, has each Recreational Association pay the master association 25% of the annual assessment for every non-resident member, plus 25% of any special assessment. That is how golf members who live outside the gates help pay for the gate, the roads and the Keewaydin shuttle they use. The club’s membership categories, 2023 fee schedule and golf course are covered in the club and golf sections of this page.
Boat slips in Windstar are owned and governed separately from the homes, and none travels automatically with a house:
The boating section below covers slip counts, the route to the Gulf and the dock history.
Most of Windstar is unincorporated Collier County; two bayfront villages, Admirals Watch and the Island at Southpointe, lie inside the City of Naples. Three independent records agree on that split: the county City_Limits layer, the FEMA flood map’s political jurisdictions layer, which places those two villages in the City of Naples flood community (CID 125130), and the tax-authority codes on the DOR 2026 roll, all read October 10, 2026.
The split shows up in four places a buyer will notice:
Whichever side of the line a home sits on, the postal address is Naples, ZIP 34112, and the master association, the gate and the Keewaydin beach are the same for every owner.
Windstar on Naples Bay owners pay a master assessment ($4,130 per home in 2025), a neighborhood or condominium assessment that varies by village, and property tax at one of three millage rates; there is no CDD, and the Windstar Club and boat slips are separate, optional costs that only the owners who choose them pay.
“What are the HOA fees in Windstar?” is the question we hear most from buyers comparing Windstar with other Naples golf and boating communities, and the honest answer has layers. Every home pays the same master assessment. Most homes also pay a village assessment on top of it, and that number is set by the village association, not the master. Property tax depends on which of three tax districts the home sits in. The club, a Southpointe Marina slip and a Regatta Landing dock slip each carry their own costs, but only for owners who buy into them. The table below lists every layer a Windstar owner can be billed, what each one covers, and whether the amount is published.
# | Layer | Amount | Period | Who pays and what it covers | Status | Source |
|---|---|---|---|---|---|---|
1 | Master assessment | $4,130 per home in 2025: $3,080 operating (including $780 for bulk Hotwire internet and TV), $800 replacement reserve, $250 hurricane reserve | Annual, billed quarterly ($1,032.50 a quarter) | Every home, one equal share. Gatehouse and gates, master roads, lakes and mangroves, the Windstar dock, the Keewaydin Island property and shuttle, bulk internet and TV, reserves | 2025 verified. The 2026 figure sits in the owner-only financials and on the master estoppel certificate | |
2 | Neighborhood or condominium assessment | Varies by village. Compass Point South: $1,968 a quarter in 2021, including its share of the master assessment | Quarterly | Members of that village. Condominium budgets carry building insurance and building reserves | One village published; for every other village the association’s budget and estoppel certificate govern | |
3 | Windstar Club (optional) | 2023 schedule published by the club: Social initiation $10,000 and dues $6,645 a year; Social Summer Golf initiation $20,000 and dues $9,545 a year; F&B minimum $1,400 family or $700 single | Initiation one time; dues annual, billed quarterly | Club members only | The club has not published a 2026 schedule | |
4 | Non-resident Recreational Association fee | 25% of the master assessment per non-resident member, plus 25% of special assessments ($765 a year on the club’s 2023 schedule) | Annual | Non-resident club or marina members only, through their Recreational Association | Rule recorded (Bylaw 8.4 as amended December 2023) | recorded compilation |
5 | Southpointe Marina slip dues | Not published | Not published | Slip owners | The marina association’s documents govern | Sunbiz N97000006209 |
6 | Regatta Landing Dock Slip Association dues | Not published | Not published | Dock Slip Certificate holders | The dock association’s documents govern | Dock Slip Certificate form; Sunbiz N17000010798 |
7 | Keewaydin private-boat dock permit | $200 | Annual | Owners who bring a boat of 30 feet or less to the master dock on Keewaydin | Verified, policy revised December 16, 2025 | |
8 | Master lease application | $145 | Per lease | Leasing owners (covers Keewaydin registration, gate access and a remote) | Verified | |
9 | Master resale capital contribution | Proposed in 2023; not in the amendment certificate recorded in January 2024 | One time, at resale | Buyers | Confirm on the master estoppel certificate | October 2023 newsletter; recorded compilation |
10 | Community Development District | None | None | None | Verified: no CDD | |
11 | Ad valorem property tax | 12.6162, 13.6162 or 9.0514 mills, by tax code | Annual | All owners, by location | Tax year 2025 rates | |
12 | County non-ad valorem charge | $261.91 | Annual | Many Windstar parcels (DOR levy code 19013) | 2025 roll | DOR 2025 non-ad valorem file |
Reading the stack: an owner who does not join the club and does not own a slip carries layers 1, 2, 11 and, on many parcels, 12. Everything else is a choice. Windstar has no Community Development District, so there is no CDD bond or operations assessment on the tax bill: the county’s CDD layer returns nothing over Windstar, and the Florida DOR 2025 non-ad valorem detail for Collier shows no special-district levy on Windstar parcels, both read October 10, 2026. That matters more than it sounds: many newer Naples communities carry a CDD line that can run for decades.
Bulk internet and television are paid for, not free. The master association’s communications page and the 2025 Annual Meeting outline put the Hotwire bulk service at $195 a quarter ($780 a year) inside the operating assessment, under a 10-year contract from March 1, 2025. The Hotwire rate sheet for Windstar on Naples Bay, dated October 24, 2024, describes the package as 500/500 Mbps internet, two TV boxes and the 199-channel Digital Favorites lineup. The authority for the bulk contract is Article 17, added by the December 2023 amendment recorded January 19, 2024 (OR 6322, PG 2115).
On timing, Bylaw 8.3 makes each quarterly installment due on the first day of the quarter and delinquent if unpaid by the 11th day of the quarter’s first month (recorded compilation). The master association holds lien rights for unpaid assessments, so a seller’s balance shows up on the estoppel certificate and is settled at closing.
Windstar’s master assessment is published for three years in the association’s own documents: $2,212 a year in 2013, $3,250 in 2024 and $4,130 in 2025. The 2013 figure is the then-current rate written into the Regatta Landing annexation agreement in the master association’s recorded compilation; the 2024 and 2025 figures and their fund splits come from the 2025 Annual Meeting outline, dated March 31, 2025.
Year | Operating | Replacement reserve | Hurricane/storm reserve | Total per home | Source |
|---|---|---|---|---|---|
2013 | $2,212 | Recorded compilation, 2013 annexation | |||
2024 | $2,200 | $850 | $200 | $3,250 | 2025 Annual Meeting outline |
2025 | $3,080 (including $780 Hotwire) | $800 | $250 | $4,130 | 2025 Annual Meeting outline |
The worked change from 2024 to 2025: $4,130 minus $3,250 is $880, an increase of 27.1% ($880 divided by $3,250). Of that $880, $780 is the new bulk Hotwire line. Strip the Hotwire line out and the rest of the assessment rose $100 between the two years, from $3,250 to $3,350. The quarterly bill in 2025 was $4,130 divided by four, or $1,032.50.
The 2026 assessment is not on the public side of the master association’s site; it sits in the owner-only financials and on the estoppel certificate a buyer’s closing agent orders. A buyer should read that certificate for the current figure rather than carrying the 2025 number forward.
The master association’s 2024 results, presented at the March 31, 2025 annual meeting, show where the money goes (2025 Annual Meeting outline):
The balance sheet at December 31, 2024 showed operating cash of $246,693, replacement reserve cash of $743,918 and a hurricane reserve of $632,382, against a term loan payable of $287,471 (principal and interest about $72k a year). The deck noted the board might pay the loan off in 2025.
The deck’s reserve projection is the line buyers should notice: a projected outlay of about $1.70 million in 2030 for docks, the channel, a road and dredging of the marina entrance, funded under the reserve plan as projected. Hurricane reserve collections are scheduled through 2027 and then stop, per the same deck. A separate committee report in the 2025 Committee Reports Binder put the master dock dredge at about $400,000, with permits expected to take two to three years (March 31, 2025). No special assessment is announced in any of these documents; any later decision would appear in the association’s notices and on the estoppel certificate.
The village layer is where Windstar’s carrying costs vary most, and it is also the least published. Only one village has posted a dollar figure publicly: the Compass Point South 2021 Q and A states dues of $1,968 a quarter, which includes Compass Point’s share of the master assessment, or $7,872 a year. Compass Point’s Structural Integrity Reserve Study, dated May 29, 2024, sets a minimum 2025 reserve funding of $118,650 and projects a starting reserve balance of $221,360 at January 1, 2025. For every other village, the budget and the estoppel certificate govern: Regatta Landing, Somerset at Windstar, Spinnaker Pointe, Marina Cove and the rest do not post their assessments publicly.
Three things drive the difference between villages:
At a sale, each association layer issues its own estoppel certificate: one from the master association, one from the village association or condominium, and, where a Regatta Landing slip certificate transfers, one from the dock association. Florida law sets the estoppel rules in section 718.116 of the Florida Statutes for condominiums and section 720.30851 for homeowners associations; the certificate states the current assessment, any balance owed and any transfer or capital contribution charge that applies. The Regatta Landing declaration defines “Capital Contribution Assessments”, and at the master level the board proposed a resale capital contribution in 2023 (President’s remarks, October 2023); the amendment certificate recorded in January 2024 does not contain one. Buyers confirm both on the estoppel certificates.
Windstar spans three Collier tax-authority codes, so two homes of the same value can pay different tax. The codes on the Florida DOR 2026 preliminary roll map to the tax year 2025 rates in the DOR-hosted 2025 Collier Taxing Authority Code Descriptions, dated October 3, 2025:
Component (tax year 2025 mills) | Code 0063 (most of Windstar) | Code 0111 (Regatta Landing) | Code 0004 (Admirals Watch, Island at Southpointe) |
|---|---|---|---|
County General Fund | 3.0107 | 3.0107 | 3.0107 |
South Florida Water Management District | 0.0948 | 0.0948 | 0.0948 |
Big Cypress Basin | 0.0978 | 0.0978 | 0.0978 |
School Board, state law | 2.0010 | 2.0010 | 2.0010 |
School Board, local | 2.2480 | 2.2480 | 2.2480 |
Collier Mosquito Control | 0.1349 | 0.1349 | 0.1349 |
Greater Naples Fire Rescue District | 2.0000 | 2.0000 | none |
Unincorporated General MSTD | 0.6844 | 0.6844 | none |
Water Pollution Control | 0.0246 | 0.0246 | 0.0246 |
Bayshore Beautification MSTU | 2.1104 | 2.1104 | none |
Conservation Collier | 0.2096 | 0.2096 | 0.2096 |
Haldeman Creek MSTU | none | 1.0000 | none |
City of Naples | none | none | 1.2300 |
Total | 12.6162 | 13.6162 | 9.0514 |
The three totals translate into a simple rule of thumb at $1,000,000 of taxable value: about $12,616.20 under code 0063, $13,616.20 under code 0111 and $9,051.40 under code 0004, before non-ad valorem charges (arithmetic on the TACD rates; not a bill).
Why the codes differ:
Separately, many Windstar parcels carry one county non-ad valorem charge of $261.91 on the 2025 roll (DOR levy code 19013), per the DOR 2025 non-ad valorem detail. Homestead exemptions and the Save Our Homes cap reduce taxable value for owners who qualify, so a new buyer’s first bill is set on the purchase-year assessment, not the seller’s.
These are illustrations, not bills; the tax collector’s bill and each association’s estoppel certificate control. Each example uses tax year 2025 millage from the 2025 Collier TACD and the 2025 master assessment from the 2025 Annual Meeting outline. Homestead exemptions change taxable value, and the village fee is the open line in each case.
Example 1: an unincorporated condominium at $600,000 taxable value (code 0063).
Example 2: a Regatta Landing coach home at $1,000,000 taxable value (code 0111).
Example 3: an Admirals Watch condominium in the City of Naples at $2,000,000 taxable value (code 0004).
Example 4: adding a club membership (2023 Social, family). On the club’s 2023 published schedule, year one cost $10,000 initiation + $6,645 dues + $1,400 F&B minimum = $18,045 (club 2023 fee pages). The F&B minimum is spending on food and drink, not a fee lost. The club has not published a 2026 schedule; current figures come from its membership office.
The comparison in Example 3 is the one buyers often miss: the City of Naples millage is about 3.6 mills lower than the main unincorporated code, so on a $2,000,000 taxable value the code difference alone is worth $7,129.60 a year ($25,232.40 at 12.6162 mills versus $18,102.80 at 9.0514).
If you own in Windstar and want to know how your fee stack compares with what buyers are paying for elsewhere in Naples, start with a free home valuation for your Windstar home or call Jesse direct at (239) 898-6072. If you are buying and want the estoppel figures for a specific village before you write an offer, call Marc at (239) 287-5873 and see how we guide Naples buyers through due diligence.
Windstar on Naples Bay holds 16 residential villages with 618 homes: nine condominium villages (428 units) and seven homeowners-association villages (190 homes), each with its own association under the master association, ranging from 1980s condominiums to 2021 coach homes and bayfront estates in the City of Naples.
Four different counts circulate for Windstar’s neighborhoods, and they all have an explanation. The community fact is 16 residential villages with 618 homes, and two independent government records agree on it to the unit: the Florida DOR 2026 preliminary roll and the Collier County address-point layer, both read October 10, 2026. The Southwest Florida MLS showed 15 village names in the 12 months to October 13, 2026 because Morningstar had no closed sale in that window, and because the MLS files the Island at Southpointe under the name “Southpointe Yacht Club”. The master association’s neighborhoods index lists 17 names because it adds the Southpointe marina slips, which are boat slips, not homes. The club’s “15 neighborhoods” is the club’s own description on its real estate page.
The name “Southpointe Yacht Club” itself has three uses, which confuses searches: it is the MLS name for the Island at Southpointe’s ten estate homes, the name of the 1988 county PUD that holds Marina Cove and Yacht Harbour Cove, and the master declaration’s defined word for the marina. The marina is a separate entity, Southpointe at Windstar Marina Association, Inc.
Village | Product | Homes | Built | Association | 12-month sales (Southwest Florida MLS, Oct 13, 2025 to Oct 13, 2026) | Sampled flood zone (FEMA NFHL, Oct 10, 2026) |
|---|---|---|---|---|---|---|
Regatta Landing | Two-story coach-home condominium | 64 | 2016 to 2021 | Condominium (Ch. 718) | 9 sales, $1,090,500 to $1,849,000 (24 months: median $1,310,000) | AE, BFE 9 |
Marina Cove | Coach-home condominium | 72 | 1997 to 1999 | Condominium | 6 sales, $507,500 to $745,000 (24 months: median $646,000) | 7 of 8 points shaded X; 1 AE 8 |
Spinnaker Pointe | Carriage-home condominium | 88 | 1994 to 1995 | Condominium | 5 sales, $525,000 to $905,000 (24 months: median $630,000) | AE 9 |
Somerset at Windstar | Duplex villas | 50 | 1989 to 1990 | HOA (Ch. 720) | 5 sales, $660,000 to $1,300,000 (24 months: median $1,095,000) | AE 9 |
Yacht Harbour Cove | Marina-basin coach-home condominium | 28 | 1996 to 1999 | Condominium | 5 sales, $1,200,000 to $2,250,000 (36 months: median $1,700,000) | AE 8 |
Windward Cay | Two- and three-story condominium | 48 | 1984 to 2004 | Condominium | 4 sales, $350,000 to $1,075,000 | AE 8 and 9 |
Compass Point South | Three-story condominium | 72 | 1992 to 1995 | Condominium | 2 sales, $430,000 and $508,000 (36 months: median $503,500) | AE 9 |
Ketch Cay | Single-family courtyard homes and villas | 42 | 1994 to 2000 | HOA | 3 sales, $1,375,000 to $1,750,000 | AE 8 |
Clipper Cove | Single-family pool homes | 35 | 1996 to 1999 | HOA | 2 sales, $1,480,000 and $1,625,000 | AE 9 |
Admirals Watch | Luxury condominium, City of Naples | 16 | 1996 to 2001 | Condominium | 3 sales, $2,375,000 to $3,625,000 | AE 8 to 9 |
Harrington Sound | Single-family estates | 27 | 1993 to 2009 | HOA | one sale, at $2,075,000 (thin) | AE 8 |
Leeward Cay | Attached villas | 16 | 1987 to 1989 | HOA | 3 sales, $800,000 to $1,270,000 | not probed; neighbors AE 8 to 9 |
Spyglass Pointe | Courtyard pool homes | 10 | 1995 to 2000 | HOA | one sale, at $1,775,000 (thin) | AE 9 |
Island at Southpointe | Waterfront estates, City of Naples | 10 | 1995 to 2012 | HOA | one sale, at $6,750,000 (thin) | AE 8 to 9 |
Northstar | Condominium villas with private pools | 16 | 1986 to 1988 | Condominium | two sales, $1,325,000 and $1,375,000 (too thin to read as a market rate) | 3 AE, 1 shaded X |
Morningstar | Condominium | 24 | 1986 to 1988 | Condominium | no closed sale in the window | 2 AE 8, 1 shaded X |
Total | 618 | 1984 to 2021 | 9 condominium, 7 HOA | 52 sales | 58 of 68 points AE |
Homes and years built are from the DOR 2026 roll; condominium status from the DBPR condominium extract; flood zones from FEMA NFHL point queries at 68 addresses on panels 12021C0581J and 12021C0582J, effective February 8, 2024. A buyer’s lender and insurer rely on the house’s own elevation certificate and flood determination, not on a sample.
Each village below follows the same order: product and streets, homes and years built, living area and county just value, the association, amenities, 12-month sales (Southwest Florida MLS, October 13, 2025 to October 13, 2026) and flood sample (FEMA NFHL, October 10, 2026; the elevation certificates are linked in the flood section). Homestead shares are in the year-round table near the top of this page. Living area and just value come from the DOR 2026 preliminary roll, read October 10, 2026; a just value is a 2026 preliminary county just value, an appraisal figure and not a sale price.
Product and streets. Regatta Landing is Windstar’s newest village: two-story coach-home condominiums of two and three bedrooms in 16 four-unit buildings at 2431 to 2521 Breakwater Way, Windward Ct and Mooring Stay Way, on the Haldeman Creek tract at the north end of Windstar.
Homes and years built. 64 homes, built 2016 to 2021 on the DOR 2026 roll. The land joined Windstar by a two-thirds owner vote on June 14, 2013, which annexed the tract into the master association under an agreement with WSC Naples, LLC. That annexation, in the master association’s recorded compilation, capped the tract at 64 homes of at least 2,000 square feet, two stories and a 35-foot mean roof height, allowed up to 42 docks, and set a $700,000 initial assessment to the master association ($250,000, a second $250,000 and $3,125 per unit at first conveyance). The condominium declaration names Standard Pacific of Florida as developer, and the county knew the site plan as “Haldeman’s Landing”.
Living area and county just value. Living area runs 2,348 / 3,018 / 3,854 square feet (minimum / median / maximum). The 2026 preliminary county just value runs $861,800 / $1,043,725 / $1,271,200.
Association. Regatta Landing Condominum [sic] Association, Inc., Sunbiz N15000008357, DBPR MA71254, managed by Paramount Property Management of Naples per the Regatta Landing association site. The amended and restated declaration makes the condominium association the master association’s collection agent, so the master assessment is inside the Regatta budget, and it states that club membership is not mandatory. The docks belong to a separate entity, Regatta Landing Dock Slip Association, Inc.; slips are held by Dock Slip Certificate and do not come with a coach home.
Amenities and rules. Pool, hot tub and grills; kayak storage and a launch on Haldeman Creek. Regatta has its own gates: a northwest gate from Haldeman Creek Dr run by the condominium and a southeast gate from Lakeview Dr run by the master association. The declaration allows no more than two leases in any 12 months, and the 2025 rules allow two cats or dogs, each under 60 pounds. Regatta Landing pays tax code 0111 (13.6162 mills for tax year 2025), which includes the 1.0000-mill Haldeman Creek MSTU; the MSTU’s 2025 survey found dredging “not currently warranted” per the Bayshore CRA’s Haldeman Creek page.
12-month sales. 9 sales, from $1,090,500 to $1,849,000; nine is under 10, so no 12-month median is shown, and over 24 months its 16 sales had a median of $1,310,000. Regatta Landing had the most sales of any Windstar village in the window.
Flood sample. Five sampled points, all Zone AE with a base flood elevation of 9 feet NAVD88 on panel 12021C0582J. The two published elevation certificates show the design: 2481 Breakwater Way has an enclosure at 8.1 feet and the living level at 13.8 feet, and 2542 Windward Ct an enclosure at 8.0 feet and the living level at 14.5 feet, against a 2024 BFE of 9.
A dedicated Regatta Landing neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Marina Cove is a coach-home condominium of 15 buildings on the Southpointe side of Windstar, at 5010 to 5025 Marina Cove Dr, 5035 to 5095 Yacht Harbor Dr and 5040 to 5080 Yacht Harbor Cir.
Homes and years built. 72 homes, built 1997 to 1999, inside the Southpointe Yacht Club PUD (Ordinance 88-82).
Living area and county just value. 1,561 / 1,822 / 3,522 square feet; 2026 preliminary county just value $433,665 / $532,830 / $597,085.
Association. Marina Cove Condo Assn., Inc., DBPR MA00022297, per the DBPR condominium extract. A manager is not posted on the master association’s page.
Amenities. The master association’s Marina Cove page describes a community center with an exercise room, a heated pool, a spa and a clubhouse.
12-month sales. 6 sales, from $507,500 to $745,000, the second-most active village in the window; over 24 months its 12 sales had a median of $646,000.
Flood sample. Marina Cove is the one Windstar village sampled mostly outside the special flood hazard area: seven of eight points were shaded Zone X (0.2% annual chance), and 5010 Marina Cove Dr was Zone AE with a BFE of 8 feet, all on panel 12021C0582J. Shaded X is not under the federal mandatory-purchase rule, but the whole community, Marina Cove included, sits in Collier Hurricane Evacuation Zone A.
A dedicated Marina Cove neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Spinnaker Pointe is a carriage-home condominium of 22 four-unit buildings on Windjammer Cir (3520 to 3588), and with 88 homes it is the largest village in Windstar; the master association’s Spinnaker Pointe page calls it the “largest neighborhood”.
Homes and years built. 88 homes, built 1994 to 1995.
Living area and county just value. 1,832 / 2,060 / 2,288 square feet; 2026 preliminary county just value $418,040 / $481,040 / $559,040.
Association. Spinnaker Pointe at Windstar Condo Assoc Inc., DBPR MA00021054 (Sunbiz N93000001338). A manager is not posted on the master page.
Amenities. A private clubhouse, a heated pool and spa, and two lighted tennis courts of its own, separate from the Windstar Club’s courts.
12-month sales. 5 sales, from $525,000 to $905,000. The $905,000 sale is a Sold Data Entry record; it counts in the five and in the range. Over 24 months its 11 sales had a median of $630,000.
Flood sample. Four points, all Zone AE with a BFE of 9 feet, panel 12021C0582J.
A dedicated Spinnaker Pointe neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Somerset at Windstar is 50 one- and two-story duplex villas on Paget Cir (2101 to 2217), governed by a homeowners association, not a condominium.
Homes and years built. 50 homes, built 1989 to 1990, among the original Windstar Development Company villages. The association has governed since 1989 under its declaration (OR 1410, PG 461), amended in 2008 at OR 4335, PG 0492.
Living area and county just value. 1,833 / 2,307 / 2,817 square feet; 2026 preliminary county just value $672,385 / $872,400 / $1,053,475.
Association. Somerset at Windstar Homeowners Association, Inc., Sunbiz N30205, managed by Newell Property Management. Its association site describes the 50 duplex villas. Its 2013 posted rules predate the master association’s 2020 leasing amendment, and the recorded master 30-day minimum lease applies.
Amenities. A community pool and spa.
12-month sales. 5 sales, from $660,000 to $1,300,000; over 24 months its 10 sales had a median of $1,095,000.
Flood sample. Four points, all Zone AE with a BFE of 9 feet, panel 12021C0582J. The elevation certificate for 2213 to 2217 Paget Cir records a lowest floor of 9.12 feet NAVD88, 0.12 feet above the 2024 BFE.
A dedicated Somerset at Windstar neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Yacht Harbour Cove is a coach-home condominium on the Southpointe marina basin: phase I at 1701 to 1765 Gulfstar Dr S and phase II at 5065 and 5075 Yacht Harbor Cir. The street is spelled “Harbor”; the village is “Harbour”.
Homes and years built. 28 homes in two recorded condominium declarations (20 units in phase I, built 1996 to 1999; 8 in phase II, 1999) under one association.
Living area and county just value. 2,437 / 2,699 / 2,961 square feet, matching the size range the association publishes; 2026 preliminary county just value $1,331,610 / $1,487,970 / $1,644,330.
Association. Yacht Harbour Cove at Windstar Condominium Association, Inc. (Sunbiz N94000004128), DBPR MA00021430 for both phases.
Amenities. The master association’s Yacht Harbour Cove page describes an island clubhouse, a pool and a spa on the marina basin.
12-month sales. 5 sales, from $1,200,000 to $2,250,000; over 36 months its 11 sales had a median of $1,700,000. Five sales from 28 homes is a brisk pace for a village this size, and the $2,250,000 sale was one of six Windstar sales at $2,000,000 or more.
Flood sample. Three points (1701, 1717 and 1765 Gulfstar Dr S), all Zone AE with a BFE of 8 feet, on panels 12021C0581J and 12021C0582J.
A dedicated Yacht Harbour Cove neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Windward Cay is a two- and three-story condominium on Yacht Harbor Dr (4400 to 4800), recorded as The Windstar Condominium Section One, with a declaration recorded April 5, 1984 (DBPR condominium extract). The master association’s Windward Cay page places its buildings along the fairways. It is not Windward Landing, the separate 2026 rezoning south of Windstar.
Homes and years built. 48 homes, built in phases from 1984 to 2004: 14 units from 1984 to 1987 (Windstar’s first homes), a 16-unit building at 4650 Yacht Harbor Dr in 1998, and three six-unit buildings at 4700, 4750 and 4800 in 2003 and 2004.
Living area and county just value. 1,589 / 1,890 / 2,250 square feet; 2026 preliminary county just value $441,085 / $568,856 / $876,500.
Association. The Windstar Condominium Section One Association, Inc., Sunbiz N01880, DBPR MA00000378, managed by Resort Management.
Amenities and inspections. A large pool, spa and cabana. The Collier milestone inspection layer lists buildings 4450, 4600 and 4650 Yacht Harbor Dr as “Milestone Completed, Cycle Completed”, next inspection year 2033, read October 10, 2026.
12-month sales. 4 sales ($350,000, $665,000, $725,000 and $1,075,000), from $350,000 to $1,075,000. The $350,000 sale was the lowest price in Windstar in the window.
Flood sample. Six points: Zone AE with a BFE of 8 feet at 4650, 4700, 4750 and 4800 Yacht Harbor Dr and 9 feet at 4400 and 4600, on panels 12021C0582J and 12021C0581J.
A dedicated Windward Cay neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Compass Point South is a condominium of four three-story buildings at 3522, 3538, 3554 and 3570 Haldeman Creek Dr, with elevators and covered parking. The master site’s “Compass Point” is this village; there is no northern Compass Point.
Homes and years built. 72 homes, built 1992 to 1995.
Living area and county just value. 1,347 / 1,414 / 1,902 square feet; 2026 preliminary county just value $375,990 / $410,990 / $555,070.
Association. Compass Point at Windstar Condo Assn., Inc., DBPR MA00008950 (Sunbiz N13709), managed by Resort Management; the association runs its own Compass Point South site. Its 2021 Q and A gives dues of $1,968 a quarter including the master share, requires board approval for leases, and states that tenants may not keep pets, while owners may keep one dog or cat of up to 25 pounds; the rules and regulations govern the details.
Inspections. All four buildings appear in the Collier milestone layer as “Milestone Completed, Cycle Completed”, next inspection year 2033. The association posted its Structural Integrity Reserve Study dated May 29, 2024, which sets a minimum 2025 reserve funding of $118,650.
Amenities. Pools, elevators and covered parking.
12-month sales. 2 sales, $430,000 and $508,000; over 36 months its 14 sales had a median of $503,500, the lowest village median in Windstar among villages with 10 or more sales in that window.
Flood sample. Three points, all Zone AE with a BFE of 9 feet, panel 12021C0582J.
A dedicated Compass Point South neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Ketch Cay is single-family courtyard homes and villas in three platted units on York Island Dr, Bollard Ct and Christina Ct, near the Southpointe end of Windstar; the master association’s Ketch Cay page notes that some face Southpointe.
Homes and years built. 42 homes, built 1994 to 2000.
Living area and county just value. 2,185 / 2,613 / 3,103 square feet; 2026 preliminary county just value $774,975 / $990,008 / $2,023,393.
Association. Ketch Cay at Windstar Residents’ Association, Inc., Sunbiz N94000005601, managed by Newell Property Management.
Amenities. Private pools and spas at the homes.
12-month sales. 3 sales ($1,375,000, $1,525,000 and $1,750,000), from $1,375,000 to $1,750,000.
Flood sample. Five points, all Zone AE with a BFE of 8 feet, on panels 12021C0581J and 12021C0582J. The elevation certificate for 1769 York Island Dr records a lowest floor of 8.7 feet NAVD88, 0.7 feet above the 2024 BFE.
A dedicated Ketch Cay neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Clipper Cove is single-family pool homes at 3804 to 3892 Clipper Cove Dr and 3813 to 3839 Clipper Ln.
Homes and years built. 35 homes, built 1996 to 1999.
Living area and county just value. 2,506 / 3,341 / 7,000 square feet on the roll; the master association’s Clipper Cove page describes homes of 2,100 to 3,000 square feet, and the county figure can include additions. The 2026 preliminary county just value runs $1,043,509 / $1,199,956 / $1,858,942.
Association. Clipper Cove Homeowner’s Association, Inc., Sunbiz N95000004387, filed September 14, 1995, managed by Ability Management.
Amenities. Each home has its own pool; no shared village pool is described.
12-month sales. 2 sales, $1,480,000 and $1,625,000.
Flood sample. Four points, all Zone AE with a BFE of 9 feet, on panels 12021C0582J and 12021C0581J.
A dedicated Clipper Cove neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Admirals Watch is a 16-unit luxury condominium at 1500 to 1650 Star Point Ln on the bay; DBPR spells it “Admiral’s Watch”. The master association’s Admirals Watch page describes private elevators, two- and three-car garages, a private pool and eight boat slips.
Homes and years built. 16 homes, built 1996 to 2001. Admirals Watch lies inside the City of Naples (county City_Limits layer), so it pays tax code 0004 (9.0514 mills for tax year 2025) and answers to the City of Naples for building and floodplain administration.
Living area and county just value. 2,550 / 2,619 / 5,279 square feet; 2026 preliminary county just value $1,595,500 / $1,846,545 / $3,310,190.
Association. Admiral’s Watch at Windstar Condominium Association, Inc. (Sunbiz N94000005983), DBPR MA00021623, managed by Ability Management. Its structural integrity reserve study and milestone status sit with the City of Naples building department and are not published.
12-month sales. 3 sales ($2,375,000, $2,935,000 and $3,625,000). All three were among Windstar’s six sales at $2,000,000 or more, and the $3,625,000 sale was the second-highest price in Windstar in the window.
Flood sample. Four points, all Zone AE with BFEs of 8 to 9 feet on panel 12021C0581J, in the City of Naples flood community (CID 125130). Zone VE begins on the open water and shoreline west of Star Point Ln.
A dedicated Admirals Watch neighborhood page is coming, with its own market snapshot and its association details.
Product and streets. Harrington Sound is Windstar’s estate-home village: single-family homes on Lighthouse Ln (4029 to 4735) in two platted units, on county RMF-6 zoning outside the Windstar PUD. The master association’s Harrington Sound page describes homes of 3,400 to over 5,000 square feet with private pools. The Lighthouse Gate, one of the four master gates, is on its street.
Homes and years built. 27 homes, built 1993 to 2009; the latest are rebuilds or late builds long after their neighbors.
Living area and county just value. 3,090 / 4,137 / 14,256 square feet, the largest median of any village; 2026 preliminary county just value $1,577,268 / $1,844,335 / $2,823,266.
Association. Harrington Sound Resident’s Association, Inc., Sunbiz N36732. A manager is not posted.
12-month sales. One sale, at $2,075,000; one sale is too thin to read as a market rate.
Flood sample. Six points, all Zone AE with a BFE of 8 feet, panel 12021C0582J. The elevation certificate for 4500 Lighthouse Ln, from 2022, records a lowest floor of 9.5 feet NAVD88, 1.5 feet above the 2024 BFE, and notes that new construction must build to BFE plus 1 foot under the Florida Building Code.
A dedicated Harrington Sound neighborhood page is coming, with its own market snapshot and its association details. That page will also cover Spyglass Pointe and the Island at Southpointe, Windstar’s other two estate-scale villages.
Product and streets. Leeward Cay is the 16-home attached-villa group on Windstar Tract L along Yacht Harbor Dr, at odd addresses between 4401 and 4773. Its identity rests on the county records: the DOR legal description for Tract L and the county parcel layer, which shows the Tract L common area owned by the Leeward Cay homeowners association.
Homes and years built. 16 homes, built 1987 to 1989, in the same first wave as Somerset at Windstar.
Living area and county just value. 2,125 / 2,125 / 2,585 square feet; 2026 preliminary county just value $823,125 / $861,125 / $1,052,825.
Association. Leeward Cay at Windstar on Naples Bay Homeowners Association, Inc., Sunbiz N30204, filed January 17, 1989, the same day as Somerset’s association. It is a homeowners association, not a condominium. Its recorded declaration is not posted publicly; the association’s documents govern.
Amenities. One pool on the group’s common area.
12-month sales. 3 sales ($800,000, $1,137,000 and $1,270,000), from $800,000 to $1,270,000.
Flood sample. No Leeward Cay address was probed directly; its Yacht Harbor Dr neighbors sampled Zone AE with BFEs of 8 to 9 feet. The elevation certificate for 4403 Yacht Harbor Dr, in the Leeward Cay range, records a lowest floor of 8.5 feet NAVD88, 0.5 feet below the nearest sampled BFE of 9.
A dedicated Somerset at Windstar neighborhood page is coming, with its own market snapshot and its association details. That page will also cover Leeward Cay, the attached-villa group built in the same years.
Product and streets. Spyglass Pointe is ten courtyard pool homes on Lookout Ln (3276 to 3312), recorded as “Tract C at Windstar Replat”, on the 15th to 17th holes along Haldeman Creek at the north edge of Windstar. The master association’s Spyglass Pointe page notes that some homes have cabana guest suites.
Homes and years built. 10 homes, built 1995 to 2000.
Living area and county just value. 2,628 / 3,158 / 5,816 square feet; 2026 preliminary county just value $1,126,729 / $1,462,728 / $1,842,037.
Association. Spyglass Pointe Homeowners Association, Inc., Sunbiz N95000004304, managed by Newell Property Management.
Amenities. Private courtyard pools; golf and mangrove views.
12-month sales. One sale, at $1,775,000; too thin to read as a market rate.
Flood sample. Two points, both Zone AE with a BFE of 9 feet, panel 12021C0582J. The elevation certificate for 3292 Lookout Ln records a lowest floor of 8.3 feet NAVD88, 0.7 feet below the 2024 BFE, which matters for a flood quote.
A dedicated Harrington Sound neighborhood page is coming, with its own market snapshot and its association details. That page will also cover Spyglass Pointe.
Product and streets. The Island at Southpointe is ten waterfront estates at 1300 to 1617 Gulfstar Dr S on a small island in the Southpointe marina basin, with its own gated entrance over a stone bridge. The master association’s Island at Southpointe page describes homes “each more than 3,500 sq ft”, many with private docks on the access channel. The MLS files these homes as “Southpointe Yacht Club”.
Homes and years built. 10 homes, built 1995 to 2012, inside the City of Naples (tax code 0004).
Living area and county just value. 3,723 / 5,413 / 17,120 square feet; 2026 preliminary county just value $2,998,548 / $3,700,757 / $6,883,100, the highest in Windstar.
Association. The Island at Southpointe Homeowners Association, Inc., Sunbiz N37243, formerly The Island at Southpointe Yacht Club Residents’ Association. These are single-family homes, not a condominium, so the condominium structural integrity reserve study rules do not reach them.
12-month sales. One sale, at $6,750,000, the highest price in Windstar in the window; one sale is too thin to read as a market rate.
Flood sample. Three points, all Zone AE with BFEs of 8 to 9 feet on panel 12021C0581J, in the City of Naples flood community (CID 125130).
A dedicated Harrington Sound neighborhood page is coming, with its own market snapshot and its association details. That page will also cover the Island at Southpointe.
Product and streets. Northstar, marketed as “The Villas of Northstar”, is a condominium of villas with private pools at 3620 to 3762 Haldeman Creek Dr (even numbers), with mangrove and bay views per the master association’s Northstar page.
Homes and years built. 16 homes, built 1986 to 1988. The condominium was declared December 16, 1986 by Windstar Development Company (DBPR condominium extract), making Northstar one of the original developer’s own villages.
Living area and county just value. 2,040 / 2,140 / 2,140 square feet; 2026 preliminary county just value $870,520 / $906,820 / $916,820.
Association. Northstar Condominium Association, Inc. (Sunbiz N14971), DBPR MA00014120, managed by Ability Management.
12-month sales. Two sales, $1,325,000 and $1,375,000, too thin to read as a market rate.
Flood sample. Four points: 3620 Haldeman Creek Dr Zone AE with a BFE of 8 feet, 3700 shaded Zone X, and 3722 and 3762 Zone AE with a BFE of 9 feet, all on panel 12021C0582J. The elevation certificate for 3660 Haldeman Creek Dr records a lowest floor of 8.80 feet NAVD88, 0.8 feet above the nearest sampled BFE of 8.
Product and streets. Morningstar is a Bermuda-style condominium of three-bedroom, two-bath homes with covered parking and a community pool, at 3601 to 3717 Haldeman Creek Dr (odd numbers), per the master association’s Morningstar page.
Homes and years built. 24 homes, built 1986 to 1988; the condominium was declared December 29, 1986 (DBPR condominium extract).
Living area and county just value. 1,324 / 1,661 / 1,880 square feet; 2026 preliminary county just value $380,340 / $481,385 / $548,800.
Association. The Naples Morningstar Condominium Association, Inc. (Sunbiz N17397), DBPR MA00007791, managed by Resort Management.
12-month sales. No closed sale in the 12 months to October 13, 2026 (Southwest Florida MLS), which is why Morningstar does not appear among the MLS’s 15 Windstar names for that window.
Flood sample. Three points: 3601 Haldeman Creek Dr shaded Zone X, and 3645 and 3717 Zone AE with a BFE of 8 feet, panel 12021C0582J.
Windstar on Naples Bay is not bundled: the Windstar Club is an equity, member-owned club that accepts non-residents, and buying a home inside the gates does not make the owner a member. The club caps golf membership at 350 and last published a fee schedule for 2023, so current costs come from its membership office.
That one fact shapes the whole Windstar buying decision. In a bundled Naples golf community, every closing carries a club membership and its dues whether the buyer plays or not. At Windstar the home and the club are two separate purchases. A buyer can own a condominium on the Southpointe basin or an estate on Lighthouse Lane, pay the master association’s assessment, ride the master association’s shuttle to Keewaydin Island, and never join the club. Another buyer can join on day one at whichever level fits. The sections below set out what the recorded documents say, what the club itself publishes, and which numbers are dated.
No. The club answers the question directly in its own FAQ: “Residents within the gates are not required to be Members. Windstar is an equity, Member-owned golf and Country Club that accepts non-resident Members.” That language is on the Windstar Club’s Our Club page, read October 2026.
The recorded documents say the same thing in legal terms. Section 1.5 of the Second Amended and Restated Master Declaration (OR 4512 PG 2575, recorded November 24, 2009, in the master association’s posted document compilation) treats the club and the marina as “Recreational Associations” and states: “No Owner or occupant gains any right to enter or to use the facilities of a Recreational Association simply by virtue of ownership or occupancy of a Unit.” The same section allows those Recreational Associations to solicit members who do not live in Windstar, and it lets the master association charge them for non-resident members under the bylaws. Regatta Landing’s own condominium declaration goes further and spells it out for its buyers: Section 3.7 of the Regatta Landing Amended and Restated Declaration of Condominium says that “Membership in the Club is not mandatory and is not required as a condition for the purchase of a Unit.”
The club’s legal name is Windstar Club, Incorporated, a Florida not-for-profit corporation filed in December 1983 according to its Sunbiz record (N00119). It is a different body from the Windstar on Naples Bay Master Association, Inc., which owns the roads, the gates, the lakes, the Windstar dock and the Keewaydin Island beach property. Buyers sometimes search for the club as “Windstar Country Club”; that informal name refers to the same Windstar Club at 1700 Windstar Boulevard.
Because membership is separate, some ordinary parts of daily life inside the gates belong to members only. The master association’s Rules and Regulations approved May 15, 2018 say that “Only Club members may use the golf course paths for walking as the golf course is for the exclusive use of Windstar Club, Inc. (‘Club’) members,” and add: “No access is permitted by virtue of ownership at Windstar on Naples Bay.” The same rules limit parking at the clubhouse to club members, people using the Keewaydin shuttle and association business. A non-member owner who walks the dog at dawn uses the master roads and sidewalks, not the cart paths.
What a non-member does keep is everything the master association runs: the gated entries, the master roads, the lakes, the Windstar dock, the Keewaydin Island beach and its shuttle, and the bulk internet and television service paid through the master assessment. The beach section below explains how that works.
The club publishes four membership categories on its Membership Types page, read October 2026. In the club’s own words and order:
Category | Golf access as the club describes it | Other privileges the club lists |
|---|---|---|
Full Golf | “unlimited rounds,” with the “bayside driving range and putting green,” locker, bag and club storage and reciprocal privileges | all clubhouse amenities, dining at all four venues, member tournaments, social events, fitness center, tennis and bocce, private beach and the Keewaydin boat shuttle |
WOW (“Waiting on Windstar”) | “limited golf during the high season of November through April and unlimited golf during the off-season of May through October until accepted as a Golf Member,” with practice facilities year-round | full clubhouse and private beach; reciprocal privileges in the summer months |
Social Summer Golf | “unlimited golf rounds during the off-season of May through October,” with practice facilities in the off season | full clubhouse and private beach year-round |
Social | no golf listed | clubhouse privileges, events, the four dining venues, tennis, bocce, fitness, the private beach and the Keewaydin boat shuttle |
Two operating rules sit beside those categories. The club states on its Our Club page that “we maintain a Golf Membership cap of 350” and that “Tee times can be reserved up to 7 days in advance.” The WOW category is the club’s own name for members who are waiting to be accepted as golf members. The club does not publish the length of any wait, so a buyer who wants in-season golf from the first winter should ask the membership office where the golf roster stands before making an offer that depends on it.
For a buyer, the four categories map to four ways of living at Windstar. A full-time golfer goes Full Golf. A seasonal resident who wants to play in summer and use the clubhouse all year looks at Social Summer Golf. A boater or beach-first owner who wants dining, courts and the club’s events but not golf looks at Social. And an owner who wants none of it simply does not apply.
The most recent fee schedule the club has published is its 2023 resident membership offer, attached to the master association’s October 2023 newsletter as the Windstar Club 2023 resident membership offer and fee pages. Every figure in this table is from that document and is dated 2023. This is the answer to the question most buyers type first, the Windstar on Naples Bay membership cost and the Windstar on Naples Bay initiation fee, with the honest caveat that the numbers are three seasons old.
2023, per the club’s published resident offer and fee pages
Line (2023 schedule) | Social, 2023 | Social Summer Golf, 2023 | Full Golf, 2023 |
|---|---|---|---|
Initiation (one time) | $10,000 (resident special of $3,000 through December 31, 2023) | $20,000 | the schedule refers to a “Full Golf Membership Contribution ($85,000)” |
Annual dues, total | $6,645 a year, billed $1,662 a quarter | $9,545 a year, billed $2,387 a quarter | not shown on the recovered pages |
Of which operating and capital | $4,200 | $7,075 | not shown |
Of which clubhouse renovation assessment | $2,100, “for 9 years or less” | included in the total | not shown |
Of which hurricane reserve | $200, “for 3 years until 2026” | included in the total | not shown |
Of which pro shop plan | $145 | included in the total | not shown |
Food and beverage minimum | $1,400 family or $700 single | $1,400 family or $700 single | not shown |
Worked example, year one as a 2023 Social family member. $10,000 initiation plus $6,645 in annual dues plus the $1,400 family food and beverage minimum comes to $18,045 for the first year (arithmetic on the club’s 2023 schedule). The food and beverage minimum is money spent on meals at the club, not a fee that disappears, so a family that dines there regularly would spend it anyway. In year two, without the initiation, the same 2023 schedule implies $6,645 in dues plus whatever the family spends on dining above the minimum.
The 2023 schedule also shows a charge that matters to anyone who joins the club without owning a home inside the gates. Under Bylaw 8.4 of the master association, as amended in December 2023 and recorded in the master association’s document compilation, each non-resident club or marina member is charged 25% of the master association’s annual assessment, plus 25% of any special assessment, billed through the club or the marina association. The club’s 2023 schedule shows that charge as $765 a year. At the 2025 master assessment of $4,130 reported in the master association’s 2025 Annual Meeting outline, the same 25% works out to $1,032.50 a year (arithmetic at the 2025 assessment rate). Residents who own a home pay the full master assessment directly and do not pay this non-resident charge.
The club has not published a 2026 schedule; current initiation, dues, transfer and refund terms come from the club’s membership office and its membership documents. That includes the Full Golf annual dues, any capital assessment levied since 2023, and what happens to a membership when a member sells a home. A buyer who plans to join should ask for the current membership plan in writing during the inspection period, and should treat any figure from a third party as unconfirmed until the club issues it.
The Windstar clubhouse at 1700 Windstar Boulevard, the address the club gives on its Directions page, sits on the bay side of the community at the end of the main boulevard. The club’s own timeline on its Our Club page marks a clubhouse grand opening in 1986, and it now describes how the club “Commemorated four decades of cherished memories with the enhancement of our Clubhouse.”
That enhancement was a member decision. Club + Resort Business reported on October 29, 2021 that Windstar on Naples Bay members approved a $13 million club renovation and expansion. Collier County’s development records list a clubhouse expansion site plan amendment for the property, application PL20210001972, in the county’s CityView projects layer. The 2023 club schedule above shows how members are paying for it: a $2,100 annual clubhouse renovation assessment inside Social dues, “for 9 years or less.” Neither the club nor the county record read for this page gives a completion date for the renovation, so this page does not give one.
Visitors are welcome by arrangement rather than by walking in. The club’s Real Estate page asks that “an appointment is made prior to visiting the Clubhouse,” which is the right first step for a buyer who wants to see the dining rooms, courts and fitness space before deciding on a membership level.
Windstar on Naples Bay’s golf course is an 18-hole, par-72 Tom Fazio design that the club dates to 1983, playing 6,701 yards from the Black tees with eight sets of tees, routed along mangroves and Naples Bay and private to Windstar Club members. Ratings below come from the club’s own scorecard.
The club’s Golf page describes “an 18-Hole Tom Fazio Design” with “eight sets of tees strategically placed,” and its history timeline places the Fazio design in 1983. The course land is substantial: Collier County’s parcel layer shows 129.48 acres owned by Windstar Club Inc across four parcels (118.88, 8.72, 1.47 and 0.41 acres). That is the open green space most Windstar homes look across, whether or not the owner plays. For anyone searching Windstar Naples golf course or Windstar golf, the essentials follow: who can play, how long it plays, and how the bay shapes it.
Every figure in this table is per the club’s scorecard, the Windstar Club scorecard PDF, read October 2026. Par is 36 out and 36 in, 72 in total. Ratings are shown as course rating and slope.
Tee | Yards | Men’s rating / slope | Women’s rating / slope |
|---|---|---|---|
Black | 6,701 | 72.6 / 135 | not printed |
Blue | 6,339 | 70.9 / 132 | not printed |
Blue/White | 6,155 | 70.1 / 128 | not printed |
White | 6,015 | 69.1 / 123 | 74.9 / 131 |
White/Gold | 5,716 | 68.1 / 120 | 73.4 / 127 |
Gold | 5,440 | 66.8 / 116 | 72.1 / 124 |
Silver | 5,059 | 65.0 / 114 | 70.0 / 120 |
Bronze | 4,595 | 63.1 / 108 | 66.9 / 115 |
From 6,701 yards at the Black tees down to 4,595 at the Bronze, the eight sets cover more than 2,100 yards, which is how one course serves a single-digit player and a beginner in the same event. The ratings are attributed to the club’s card.
The scorecard’s local rules are the clearest picture of how the course is laid out. They name lateral penalty areas of “Mangroves/natural areas to the left and behind” on holes 5, 6, 7, 8 and 9, and “Mangroves / natural areas to the right and behind” on holes 15, 16, 17 and 18, according to the club’s scorecard. In plain terms, much of the closing stretch of each nine runs along the mangrove edge of Naples Bay. The club’s Membership Types page describes a “bayside driving range and putting green” for practice.
Living next to the course comes with recorded terms that every buyer of a golf-view home should read. Article 4 of the Master Declaration grants an easement “to permit the doing of every act necessary and proper to the playing of golf over and through properties adjacent to the golf course,” including the “inadvertent overflight of golf balls.” Owners expressly assume the risk of noise, personal injury or property damage from the operation and maintenance of the club, including maintenance noise around sunrise and sunset, spraying, view changes and errant balls. A buyer who loves the fairway view should also expect early mowers and the occasional ball on the lanai.
The lakes that thread through the course carry their own rule. The master association’s 2018 Rules and Regulations say the club permits fishing “only on the roadside banks of its lake at the corner of Windstar Boulevard and Haldeman Creek Drive,” and that fishing “is not allowed from banks that abut golf course property.” The master association’s fishing-site map marks where residents may cast.
The club says on its Bay Life page that its course has been an Audubon Cooperative Sanctuary since 1998, describing a “rigorous process of environmental stewardship.” That status suits a course whose boundaries are mangrove and bay, and it is one reason wading birds are a daily sight on the back nine.
Programming runs through the season. The club’s Golf page lists men’s weekly play and events, ladies’ 9-hole and 18-hole leagues with “20+ events each season,” and annual major championships “accessible to all Golf Members.” A Director of Golf leads a professional staff that offers lessons and runs the practice facilities. The club’s history timeline also records touring professionals who once represented Windstar in the 1980s, part of the club’s own story of its early years.
The club does not claim a published course ranking, and this page does not give one. What the record supports is simpler: a private 18-hole Fazio course on the water, with eight sets of tees, a 350-member golf cap and tee times seven days out.
Windstar on Naples Bay offers water access three ways: Southpointe Marina on the bay (72 slips per the club, yachts to 70 feet), Regatta Landing’s dock-slip association on Haldeman Creek, and private slips at Admirals Watch and the Island at Southpointe, all south of the US 41 bridge.
Each of those dock systems has its own owner, its own association and its own rules, and none of them comes automatically with a home. Southpointe slips are held through a marina association, Regatta Landing slips through a dock-slip association, and the Admirals Watch and Island slips belong with those villages. The master association runs a fourth dock at the clubhouse, but that dock serves the Keewaydin shuttle, not private boats. A buyer whose plan starts with a boat should read this section first and match the village to the slip.
The marina at the south end of Windstar goes by several names, and they all mean the same basin. The club’s Bay Life page says “Southpointe Marina has 72 slips and can accommodate yachts up to 70 feet,” and the county’s 1988 Ordinance 88-82 for the Southpointe Yacht Club PUD describes an existing 72-slip basin. The Florida Department of Revenue’s 2026 preliminary tax roll for Collier County carries 73 slip parcels at the marina, one more than the 72 slips the club and the 1988 PUD describe. On that roll, the median 2026 preliminary county just value per slip parcel is $251,497, which is an appraisal figure for tax purposes and not a sale price for a slip.
The slips are not owned by the club. The owner-run entity is Southpointe at Windstar Marina Association, Inc., a not-for-profit filed in November 1997, per its Sunbiz record (N97000006209). The Florida Department of Environmental Protection lists “Southpointe Marina at Windstar” among its Designated Clean Marinas in the South District, part of the state’s Clean Marina program for marinas that adopt environmental best practices. The master declaration uses yet another name, “Southpointe Yacht Club,” as its defined word for the marina, and Southpointe Yacht Club is also the name of the 1988 county PUD and the name the Southwest Florida MLS uses for the ten estate homes on the Island at Southpointe. When a buyer searches for Southpointe Marina Naples or Southpointe at Windstar Marina, this basin is the answer.
Southpointe slip dues and the marina association’s budget are not published. A buyer of a slip, or of a home that conveys with one, should ask for the marina association’s governing documents, current dues and any special assessment through the estoppel process. A non-resident who owns a slip and does not own a Windstar home pays the 25% non-resident charge to the master association through the marina association, under the Bylaw 8.4 rule described in the club section above.
Regatta Landing, the newest village at Windstar, has its own dock facility on Haldeman Creek. The 2013 annexation allowed up to 42 docks (master association’s document compilation, OR 4933 PG 1493); the county Planning Commission denied a 42-slip version on June 19, 2014, a 26-slip facility went on the Board of County Commissioners’ consent agenda on January 12, 2016 (BCC agenda item 16A29), and the county’s site address points layer shows 27 wet-slip address points today.
Slips are held by Dock Slip Certificate through Regatta Landing Dock Slip Association, Inc., per its Sunbiz record (N17000010798) and the association’s Dock Slip Certificate Assignment form (Exhibit P, OR 5448 PG 1149). The 2013 agreement set the order of who may buy: slips were to be offered first to Regatta Landing owners, then to other Windstar owners, and to outside buyers only starting one year after all the Regatta Landing homes had sold. It bars live-aboards at the Regatta docks, and it says outside slip owners pay a share of the master assessment, “currently 25% of the standard association assessment.” The built slip count and the dock association’s dues are not published.
Haldeman Creek carries its own public maintenance program. The Bayshore CRA’s Haldeman Creek projects page reports that the Haldeman Creek MSTU’s 2025 survey found dredging “not currently warranted,” and Regatta Landing parcels pay the 1.0000-mill Haldeman Creek MSTU on the county tax bill. This page does not state a controlling depth on the creek or describe the Regatta route as free of any crossing structure; those facts sit in the dock permits and chart soundings, and a boat buyer should confirm both with a local captain and the dock association before buying for a specific vessel.
Two bayfront villages have water at the door. The master association’s Admirals Watch page describes 16 condominiums with eight boat slips belonging to that village. The Island at Southpointe page describes ten estate homes on a small island reached by a gated stone bridge, “many with private docks on the access channel.” Both villages sit inside the City of Naples rather than unincorporated Collier County, which matters for permits and dock work.
These are the slips that come closest to a backyard-boat lifestyle inside the Windstar gates. The number is small: eight slips in one village, and private docks at some of ten homes in the other. Allocation of the Admirals Watch slips, and dock rights on any Island home, are set by each village’s own documents, so the title work and the association’s records decide them.
The route from Windstar’s bay docks to open water runs south. NOAA’s U.S. Coast Pilot 5, Chapter 4 (edition of October 4, 2026) describes “a dredged channel” that “leads from the Gulf of America through Gordon Pass, thence north to the U.S. Route 41 highway bridge at Naples about 2.5 miles above Gordon Pass.” It places that bridge, a “32-foot fixed span with a clearance of 10 feet,” at “the head of the harbor.”
NOAA’s Coast Pilot places the US 41 bridge (10-foot clearance) at the head of Naples Bay, north of Windstar; boats from Southpointe Marina and the master dock run south to Gordon Pass without passing under it. For a buyer with a center console or a cruiser, that is the practical answer to the bridge question for the bay-side docks.
The same Coast Pilot chapter sets the speed rule: “A no-wake speed limit is enforced in Gordon Pass between Daybeacons 7 and 10 and in Naples Bay between Daybeacon 29 and the bridge at Naples.” Boaters should plan for slow running through the pass and in the busier upper bay. Collier County also has state manatee protection zones under Florida Administrative Code rule 68C-22.023; the zones that apply on a given stretch of water are set by that rule and its maps, which every Windstar boater should read before the first run.
The master association’s dock at the clubhouse, home of the Keewaydin shuttle, has a sand problem. A Coastal Engineering Consultants bathymetric survey, field work dated December 27, 2023, ran a 950-foot line from the Windstar dock to the federal channel, as reported in the master association’s Keewaydin Binder. The master association’s 2025 Committee Reports Binder, in a report dated March 31, 2025, says the shuttle operator “needed to cancel schedule trips a number of times during low tide,” that “It will take 2-3 years to obtain the various permits,” and that dredging is “estimated to be around $400,000.” The committee’s November 21, 2024 report confirms that the permit process had begun.
The master association’s longer reserve plan points the same way. Its 2025 Annual Meeting outline projects a reserve outlay of about $1.70 million in 2030 for docks, channel, road and marina entrance dredging. For a buyer, the takeaway is not alarm but budgeting: the master assessment already carries a replacement reserve line, and dredging is a known future cost the board has put on paper.
If boating is the reason you are looking at Windstar, the slip is often worth as much attention as the house. Sellers with a slip, or a home that conveys one, can get a free valuation of their Windstar home or Call Jesse direct at (239) 898-6072. Buyers matching a boat to a village and a dock can Call Marc at (239) 287-5873 or start with our guide to buying a home with McGreevy and Comisar.
Windstar on Naples Bay’s beach is about five acres of master-association land on Keewaydin Island, a barrier island south of Naples, reached on the association’s Keewaydin Queen III shuttle in about 40 minutes from the dock behind the clubhouse; residents use it whether or not they join the club.
Ownership is the key fact, and the master association states it plainly on its Keewaydin Beach and Shuttle page: “The Keewaydin Beach and Keewaydin Queen III Shuttle are owned by the Windstar on Naples Bay Master Association for the benefit and enjoyment of Windstar residents and non-resident members of the Club and Marina.” The county’s parcel layer shows two master-owned Keewaydin parcels of 2.68 and 2.74 acres, and the 2025 Annual Meeting outline lists the “Keewaydin Island Property (approx. 5 acres) and the Keewaydin Queen” among the things the master assessment funds. The master association owns the Keewaydin Island property and the shuttle and funds them through the master assessment; residents use them whether or not they join the club; non-resident club and marina members gain access through the 25% Recreational Association fee. The club’s pages describe the beach as a benefit of membership, and it is, but the title sits with the master association. The shuttle is run under contract by Mariner Services, Inc. with licensed Coast Guard captains.
Windstar’s beach is a master-owned property on Keewaydin Island reached by the association’s shuttle boat. There is no Gulf beach inside Windstar itself and no road to Keewaydin; the shuttle, or a private boat, is the way across.
The shuttle is seasonal, and the season has moved. The master association’s March 2025 committee report in the 2025 Committee Reports Binder says that “Beginning next season, these trips will be offered from November 1 through July 15,” which applies from the 2025/26 season on. Check the master association’s current calendar before planning a visit, because days of the week vary through the season.
Day trips run in two sessions, per the master association’s Keewaydin page: the morning trip departs at 9:30 a.m. and is back by 1:00 p.m., and the afternoon trip departs at 11:30 a.m. and is back by 3:30 p.m. The ride takes about 40 minutes each way from the dock behind the clubhouse.
Booking rules come from the Keewaydin Booking, Cancellation and Slip Use Policies (revised December 16, 2025):
Weather and water decide the rest. Trips are cancelled when forecast winds exceed 20 mph, and the captain may cancel at low tide, as the 2025 committee reports and the Keewaydin Binder both describe. That low-tide issue is the shoaling at the master dock covered in the boating section above.
Keewaydin is a natural barrier-island beach, and the master association is candid about it. Its booking policies say that restrooms, outdoor showers and beach umbrellas “are available only when day trips to Keewaydin Island are operating,” and that “Keewaydin is not a full-service beach club.” Pack the cooler and the sunscreen.
The island took a beating in 2024. The 2025 Committee Reports Binder reports that Debby, Helene and Milton damaged the island facilities, destroying the generator, pump and water tank and damaging the deck; trips resumed November 1, 2024, and solar power has run the island since February 2025, with the generator as backup.
Pets stay home. The master association’s 2018 Rules and Regulations say: “No pets are allowed on the Shuttle boat at any time or on the island property from October 15th to July 15th.”
The shuttle also runs evening cruises. Under the December 2025 policies, scheduled evening cruises cost $20 per person plus tax, and a private specialty cruise costs $20 per person with a $400 minimum and a 35-person maximum. Sunset and full-moon cruises and the holiday boat parade are the usual draws.
Windstar owners with their own boats can tie up at the island dock under a permit. The Keewaydin booking and slip policies set the terms:
The island dock is due for replacement in 2026, and the policies say that after it, “surveillance cameras and a gated access system will better protect the private use” of the dock. The dock sits under a state submerged land lease, which the committee’s November 2024 report explains limits how far it can be moved without a new lease survey.
Windstar on Naples Bay’s courts belong to the Windstar Club: six Har-Tru tennis courts (two lit) and three lighted Har-Tru bocce courts; the club lists no pickleball courts, and Spinnaker Pointe keeps two lighted tennis courts of its own for its residents.
The racquet picture is simple to state. Club members get a full Har-Tru tennis program and bocce under the lights. Spinnaker Pointe residents have two neighborhood courts, according to the master association’s Spinnaker Pointe page. Pickleball players drive about a mile to a public center.
The club’s Tennis page describes “6 meticulously cared for Har-Tru tennis courts” with “two illuminated courts for evening matches.” Har-Tru is the green clay surface that plays slower and is easier on knees than hard courts, a common choice at Naples clubs. Programming includes clinics, round robins, live-ball sessions, doubles play and private lessons under a Director of Court Sports, and the club said it would join interclub leagues in late 2024. Tennis is included in every published membership category, including Social.
Spinnaker Pointe’s two lighted courts are separate from the club and belong to that village’s association; the master association’s page describes them alongside Spinnaker Pointe’s private clubhouse, heated pool and spa.
The club has three lighted Har-Tru bocce courts beside its indoor and outdoor bar, per its Bocce page, with weekly programming and courts that members can book for private gatherings. Bocce at Windstar is as much a social event as a sport, and the location next to the bar is the point.
The club lists no pickleball courts; the public Naples Pickleball Center at East Naples Community Park is nearby. The Windstar Club home page links out to the Naples Pickleball Center rather than listing courts of its own. East Naples Community Park, at 500 Thomasson Drive, is about 1.13 miles in a straight line from the clubhouse, measured on Collier County’s parks layer. For a buyer who plays daily, that public center is the realistic home court.
Windstar on Naples Bay dining and fitness run through the Windstar Club, with four dining venues and a new fitness center the club says opens in 2026; the club lists no pool or spa, so pools belong to the villages, from Spinnaker Pointe’s clubhouse pool to Marina Cove’s community center.
That split matters to a buyer comparing Windstar with Naples communities built around a central resort pool. At Windstar the pool is a village amenity, paid for through the village association, and the village a buyer chooses decides whether there is a shared pool, a private pool at the home, or both.
The club runs four dining venues, named on its Dining page: 1700 Grille, the Bayview Dining Room, the Sunset Lounge and Veranda, and The Wine Room. The club describes the Wine Room and Bayview Dining Room as settings for private parties and events, the Sunset Lounge and 1700 Grille as places to relax, and the Veranda as the spot for “picturesque views of Naples Bay.”
The clubhouse works on two levels in more than one sense. The upstairs dining rooms keep country-club attire for evening dining, while the downstairs 1700 Grille is casual, the place to eat after a morning at Keewaydin or a round of golf. The club’s Our Club page describes itself as “casual by design.” Dining at all four venues is part of every published membership category.
The club’s Fitness Center page says: “Windstar has a new Fitness Center ready to welcome you in 2026! In the interim, we have a temporary Fitness Center offering all of the equipment you would like and a full work-out class schedule!” Classes listed include HIIT, Functional Fitness, Core and Balance, Mobility Monday, Lower Body Strength, Flex Flow Yoga, Upper Body Strength and Flexibility Friday.
The county’s CityView projects layer shows a fitness-center site plan amendment (PL20240013453) and a temporary fitness facilities amendment (PL20220004780), both listed at the site inspection stage. As of October 2026 no record read for this page confirms that the new fitness center has opened, so ask the club for its status when you visit.
The club’s published amenity list has no pool or spa; pools are run by the neighborhood associations. The club’s home, Our Club, Lifestyle, Membership Types and Real Estate pages describe golf, tennis, bocce, dining, fitness, the beach and the shuttle, and none describes a club pool or spa.
The villages fill that gap. Per the master association’s neighborhood pages and the village association sites, shared pools are described at Admirals Watch, Marina Cove (community center with exercise room, heated pool and spa), Spinnaker Pointe (private clubhouse, heated pool and spa), Windward Cay, Morningstar, Regatta Landing, Somerset at Windstar, Yacht Harbour Cove (island clubhouse) and Compass Point South, while Clipper Cove, Harrington Sound, Ketch Cay, Spyglass Pointe and Northstar homes have private pools.
For a buyer, this is a real sorting tool. Someone who wants to swim laps without maintaining a pool looks first at the condominium and coach-home villages with association pools. Someone who wants a private pool off the lanai looks at the single-family and villa villages.
Much of Windstar’s social life runs through member groups. The club’s Clubs within a Club page lists fishing, wine, book, cigar, bourbon, bridge, mah jongg and cycling groups, and its Events and Culture page adds Concerts on the Bay, a VIP speaker series and wine dinners.
One group belongs to the master association rather than the club: the Windstar Kayak Club keeps shared kayaks at the Windstar dock, with 6 guest passes a year and extra passes at $10 each, and privately owned kayaks may not be stored or launched there (2018 Rules and Regulations).
Windstar on Naples Bay sits in Collier Hurricane Evacuation Zone A on the east shore of Naples Bay. Hurricane Ian in 2022 pushed Naples Bay to about 7.1 feet NAVD88 at a sensor about 3.4 kilometres north of Windstar, and the master association now carries a separate hurricane reserve funded at $250 per home a year.
Windstar sits on low coastal land between Naples Bay and Haldeman Creek, so storm surge, not wind alone, is the hazard to understand first. Every water level below is tied to a named gauge or surveyed mark, with its distance from Windstar and its datum: NAVD88 is the reference on the current FEMA maps and modern elevation certificates, while MHHW (mean higher high water) is how the National Hurricane Center often reports surge, and the two are not interchangeable.
Hurricane Ian came ashore in Southwest Florida on September 28, 2022, and it is the benchmark storm for every Naples Bay community. The National Hurricane Center’s Tropical Cyclone Report on Hurricane Ian states: “Maximum inundation of 6 to 9 ft AGL occurred in Naples.” AGL means above ground level, so that range describes how deep the water stood over the ground in the hardest-hit parts of the city, not how high the water rose against a fixed datum.
The closest instrument readings to Windstar are these:
Record | Where it was, relative to Windstar | Peak | Datum | Source |
|---|---|---|---|---|
USGS water level sensor, Gordon River Bridge, Naples Bay | about 3.4 km north on the same bay | 7.1 ft | NAVD88 | NHC Ian report |
USGS high water marks, Tin City (seed lines) | about 3.4 km north on Naples Bay | 7.13 and 7.15 ft | NAVD88 | |
NOAA tide gauge 8725110, Naples pier | open Gulf side of the city | 6.79 ft (6.18 ft above MHHW), then the gauge was destroyed | NAVD88 | NOAA CO-OPS water level record, Naples and the NHC report |
The NHC report itself names Naples Bay among the waters Ian’s surge reached: “Ian produced a catastrophic storm surge along the southwest coast of Florida, impacting the barrier islands near Fort Myers, as well as rivers and bays such as the Caloosahatchee River, Estero Bay, the Imperial River, and Naples Bay.”
No surveyed Ian high water mark sits inside the Windstar gates. The United States Geological Survey’s Ian marks nearest to Windstar are the Tin City marks about 3.4 kilometres up the bay, so no one can state from the public record exactly how deep the water stood at any particular Windstar address during Ian. Surge on a bay is also not uniform; Windstar’s south and west shore faces the open lower bay, while the Tin City marks sit near the head of the harbor.
For reference only, the 7.1-foot bay reading 3.4 kilometres north falls below the lowest floors of 8.0 to 9.5 feet NAVD88 on the eight modern Windstar elevation certificates read for this page and above some of their garage slabs (6.0 to 8.1 feet); the flood section below lists them. That comparison is not a statement of what happened at any home; the certificate, the seller’s disclosure and the claim history for the address answer that.
Three other storms frame Windstar’s modern storm history, and each one tested a different part of the community.
Irma (September 10, 2017). Irma produced an unusual tide in Naples. The NHC’s Tropical Cyclone Report on Hurricane Irma records that the Naples gauge “recorded a minimum water level of 4.8 ft below MHHW,” and that once the center moved north of Naples and the winds shifted onshore, “the water level at the site increased by 9 ft in only 3 hours.” The Naples gauge peaked at 4.85 feet NAVD88, per the NOAA CO-OPS record for station 8725110. The closest surveyed mark to Windstar from any of these storms is an Irma mark: a USGS seed-line high water mark at 4.34 feet NAVD88, about 175 meters west of 1700 Windstar Boulevard, per the USGS STN high water mark record. The NHC summarized the regional result: “Maximum inundation levels of 3 to 5 ft above ground level occurred along the remainder of the southwestern coast of Florida from Marco Island northward through Naples to Ft. Myers.”
Helene (September 26, 2024). Helene still pushed water into Naples Bay. NOAA’s Naples Bay, North gauge (station 8725114), about 2.7 kilometres north of Windstar, peaked at 4.71 feet NAVD88 (4.02 feet above MHHW). The NHC’s Tropical Cyclone Report on Hurricane Helene states: “South of Bonita Beach, maximum storm surge inundation of 2 to 4 ft AGL occurred in areas such as Naples, Marco Island, and Everglades City.”
Milton (October 9, 2024). Two weeks later Milton drove water into the bay again. The same Naples Bay, North gauge reached 5.77 feet NAVD88 (5.08 feet above MHHW). The NHC’s Tropical Cyclone Report on Hurricane Milton reports: “Maximum storm surge inundation of 3-5 ft AGL occurred from Bonita Beach through Marco Island. The NOS tide gauge in Naples Bay reported 5.08 ft above MHHW.”
The 2024 season left marks on Windstar’s own facilities rather than on its homes. The master association’s 2025 Committee Reports Binder reports that Debby, Helene and Milton destroyed the Keewaydin Island generator, pump and water tank and damaged the island deck; the shuttle resumed trips on November 1, 2024, and the island has run on solar power since February 2025. The master association’s 2025 Annual Meeting outline shows about $127,000 spent from the hurricane fund in 2024, covering Debby, Helene, Milton and residual Ian work.
Salt water also reaches the lakes after a storm: the master association’s Quarterly Water Test Report for June 2025 shows salinity of about 0.7 to 8.4 parts per thousand across the sampled ponds.
Windstar’s master association pays for storm recovery on common property out of a dedicated fund rather than relying only on special assessments after the fact. The 2025 Annual Meeting outline breaks the 2025 master assessment of $4,130 per unit into three funds, and one of them is a Hurricane/Storm Reserve of $250 per unit, up from $200 in the 2024 assessment of $3,250. The same document reports the hurricane reserve balance at $632,382 on December 31, 2024, and its cash projection schedules hurricane-fund collections for 2025 through 2027.
That fund covers master property: the gates and gatehouse, master roads, walls and landscaping, the lakes and mangroves, the Windstar dock and the Keewaydin Island property and shuttle. It does not insure or repair anyone’s home. Each condominium association carries its own building insurance and reserves, each homeowners’ association handles its own common areas, and each owner insures his or her own house or unit interior. A buyer reading an estoppel letter or a village budget should look for both layers: the master hurricane reserve line in the master assessment, and the village association’s own insurance and reserve position.
The Windstar Club runs its own separate storm money for the clubhouse and course. The club’s 2023 fee schedule, covered in the club section above, showed a $200 hurricane reserve inside Social dues, “for 3 years until 2026.” Club and master funds are separate, and only the master fund touches every owner.
Rules also govern storm preparation at the house level. Regatta Landing’s Rules and Regulations dated September 5, 2025 allow flood barriers only around a storm and require them to come down within 48 hours after it passes. Other villages set their own shutter and barrier rules in their declarations and rules, and those documents govern for each village.
Every Windstar address point checked against Collier County’s Hurricane Evacuation Zone layer on October 10, 2026, all 68 of them across every village, returned Evacuation Zone A. Zone A is the county’s most surge-exposed evacuation zone. In practice that means a Windstar household, whether in a shaded Zone X coach home at Marina Cove or an estate on the Island at Southpointe, should plan to evacuate when Zone A is called, and should have a destination inland picked before the season starts. The evacuation zone is a surge-planning designation, separate from the FEMA flood zone that drives insurance; a home can sit in shaded Zone X on the flood map and still sit in Evacuation Zone A.
The Coastal High Hazard Area (CHHA) is a planning line rather than an insurance zone. Collier County staff placed the Fisherman’s Village tract (now Regatta Landing) inside the Coastal High Hazard Area in 2006, as the BCC agenda staff summary of October 10, 2006 records, and the county’s CHHA boundary line runs east of Windstar. The CHHA’s consequence is about density: county Growth Management Plan policy limits residential density increases in the CHHA, which matters on a rezoning or redevelopment application, not on the purchase or insurance of an existing home. Windstar’s land carries the Urban Coastal Fringe Subdistrict designation on the county’s Future Land Use layer, the coastal designation the county uses for this stretch of the Bayshore corridor.
Windstar on Naples Bay is mostly FEMA Zone AE with base flood elevations of 8 or 9 feet NAVD88 on the February 8, 2024 maps; of 68 sampled addresses, 58 were AE and 10 shaded Zone X, Marina Cove was mostly shaded X, and no sampled home fell in Zone VE.
Method: on October 10, 2026, each of 68 Collier County address points, spread across every Windstar village, the marina and the main boulevard, was queried against FEMA’s National Flood Hazard Layer: layer 28, Flood Hazard Zones for the zone and base flood elevation (BFE), layer 3, FIRM Panels for the panel and effective date, and layer 22, Political Jurisdictions for the NFIP community. Every point is labeled with the village it belongs to under the county’s subdivision records. Zone AE and shaded X are both present at Windstar; the house-level determination is the elevation certificate and the lender’s flood zone determination for that specific building, not a sample.
The overall result: 58 of the 68 points are Zone AE (32 at a BFE of 9 feet and 26 at a BFE of 8 feet, both NAVD88), 10 are shaded Zone X (the 0.2 percent annual chance flood area), and none is Zone VE, the coastal high-velocity zone. Two FIRM panels cover Windstar, 12021C0581J and 12021C0582J, both effective February 8, 2024. Sixty-one points fall in the unincorporated Collier County NFIP community (120067) and seven in the City of Naples community (125130), the seven being Admirals Watch and the Island at Southpointe.
The nearest VE zones are on the water, not on homes: FEMA maps a VE 11 area over the Naples Bay water and shoreline west of Star Point Lane and the west end of Windstar Boulevard, and a VE 10 area along the shoreline near Danford Street south of Gulfstar Drive South, per the NFHL flood hazard layer.
Every one of the 68 address points was queried on October 10, 2026 against the FEMA NFHL and returned Collier Hurricane Evacuation Zone A on the county evacuation layer; the table rolls them up by village. Leeward Cay was not probed directly; its attached villas sit on Yacht Harbor Drive between sampled Windward Cay and Harrington Sound points that are all Zone AE.
Village | Points | Zones | BFE ft NAVD88 | Panel(s) | NFIP community |
|---|---|---|---|---|---|
Regatta Landing | 5 | AE | 9 | 0582J | Collier County |
Marina Cove | 8 | 7 shaded X, 1 AE | 8 (at 5010 Marina Cove Dr) | 0582J | Collier County |
Spinnaker Pointe | 4 | AE | 9 | 0582J | Collier County |
Somerset at Windstar | 4 | AE | 9 | 0582J | Collier County |
Yacht Harbour Cove | 3 | AE | 8 | 0581J, 0582J | Collier County |
Windward Cay | 6 | AE | 8 (4650 to 4800), 9 (4400, 4600) | 0582J, 0581J | Collier County |
Compass Point South | 3 | AE | 9 | 0582J | Collier County |
Ketch Cay | 5 | AE | 8 | 0581J, 0582J | Collier County |
Clipper Cove | 4 | AE | 9 | 0582J, 0581J | Collier County |
Admirals Watch | 4 | AE | 8 to 9 | 0581J | City of Naples |
Harrington Sound | 6 | AE | 8 | 0582J | Collier County |
Spyglass Pointe | 2 | AE | 9 | 0582J | Collier County |
Island at Southpointe | 3 | AE | 8 to 9 | 0581J | City of Naples |
Northstar | 4 | 3 AE, 1 shaded X | 8 to 9 | 0582J | Collier County |
Morningstar | 3 | 2 AE, 1 shaded X | 8 | 0582J | Collier County |
Leeward Cay | 0 direct | not probed; neighbors AE 8 to 9 | n/a | n/a | Collier County |
Southpointe Marina (1777 Gulfstar Dr S) | 1 | AE | 9 | 0581J | Collier County |
Common areas (Windstar Blvd, incl. clubhouse) | 3 | 2 AE, 1 shaded X (clubhouse) | 8 to 9 | 0581J, 0582J | Collier County |
Total | 68 | 58 AE, 10 shaded X | 53 on 0582J, 15 on 0581J | 61 Collier, 7 City |
Three readings matter most to buyers. First, Marina Cove is mostly shaded Zone X: seven of its eight sampled points are shaded X, and only 5010 Marina Cove Drive sampled AE 8. Second, Yacht Harbour Cove, its neighbor on the Southpointe basin, sampled Zone AE at a BFE of 8 feet at all three of its points, so the two marina-side villages should not be confused. Third, Northstar and Morningstar on Haldeman Creek Drive are mixed, with one shaded X point each and the rest AE, which is exactly why the certificate and the lender’s determination for the specific building decide the question. Every other village sampled entirely in Zone AE.
A flood zone tells a buyer what the map expects; an elevation certificate tells the buyer how high the house actually sits. Collier County publishes certificates for many Windstar addresses through its Elevation Certificates layer. The eight modern certificates read for this page compare as follows against the 2024 BFE at the same spot (owner names are not reproduced):
Address | Village | Certificate | Lowest floor ft NAVD88 | 2024 BFE ft | Lowest floor vs 2024 BFE |
|---|---|---|---|---|---|
2481 Breakwater Way | Regatta Landing | enclosure 8.1; living level 13.8 | 9 | enclosure minus 0.9; living level plus 4.8 | |
2542 Windward Ct | Regatta Landing | enclosure 8.0; living level 14.5 | 9 | enclosure minus 1.0; living level plus 5.5 | |
3292 Lookout Ln | Spyglass Pointe | 8.3 | 9 | minus 0.7 | |
4500 Lighthouse Ln | Harrington Sound | 9.5 | 8 | plus 1.5 | |
1769 York Island Dr | Ketch Cay | 8.7 | 8 | plus 0.7 | |
2213 to 2217 Paget Cir | Somerset at Windstar | 9.12 | 9 | plus 0.12 | |
4403 Yacht Harbor Dr | Leeward Cay range | 8.5 | 9 (nearest sampled BFE) | minus 0.5 against the nearest sampled BFE | |
3660 Haldeman Creek Dr | Northstar | 8.80 | 8 (nearest sampled BFE) | plus 0.8 against the nearest sampled BFE |
Garage slabs on the same certificates run from 6.0 to 8.1 feet NAVD88. Regatta Landing’s two certificates show the design of the newest village: a ground-level garage and storage enclosure at about 8 feet, with living space beginning at 13.8 to 14.5 feet, well above today’s BFE of 9. Under flood insurance rules an enclosure used only for parking, building access and storage, with proper flood openings, is generally treated differently from a living floor, and the certificate is how the insurer sees it.
The BFE itself has moved over Windstar’s life, and that history explains why older certificates can read differently from new ones:
So a certificate surveyed under the 2012 map, when the BFE on Lookout Lane was 7 feet, can show a house comfortably above BFE that now sits below it under the 2024 map. The 3292 Lookout Lane certificate is the example: 8.3 feet against a 2012 BFE of 7.0, and against a 2024 BFE of 9.
New construction carries an extra margin. The surveyor’s note on the 4500 Lighthouse Lane certificate states: “ACCORDING TO THE 2017 FLORIDA BUILDING CODE, AN ELEVATION 1.0’ HIGHER THAN THAT SHOWN IN B9 MUST BE USED FOR CONSTRUCTION PURPOSES.” In plain terms, a new home is built at least one foot above the BFE. The same logic applies to major work on an existing home. Federal flood rules in 44 CFR 59.1 define substantial improvement and substantial damage at 50 percent of the structure’s market value; past that threshold, a building must be brought into compliance with current flood elevation rules. A buyer planning a large renovation of a house whose lowest floor sits below the 2024 BFE should price that rule in before writing an offer.
FEMA issued preliminary flood map data for Collier County on March 20, 2025, according to the FEMA Preliminary NFHL. For Windstar the preliminary study changes the paper but not the answer: panel 0582 becomes 0582K, with no change in zone or BFE at any of the 53 sampled Windstar points on that panel, and panel 0581 is not being revised at all. The new panel will carry its own effective date once FEMA finalizes it.
No effective Letter of Map Revision covers Windstar, and none of the Letters of Map Amendment in the surrounding area is for a Windstar building, per the NFHL as queried on October 10, 2026. A Windstar owner whose certificate shows a lowest floor and lowest adjacent grade above BFE can explore a map amendment with a surveyor, but no Windstar building has one on file today.
Flood facts change what a home is worth and what it costs to carry, and they work in both directions: a high lowest floor is a selling point, and a low one is a negotiating point. Sellers who want the certificate read into the price can request a free valuation of their Windstar home or Call Jesse direct at (239) 898-6072. Buyers comparing villages by zone and floor height can Call Marc at (239) 287-5873 or read our step-by-step guide to buying with McGreevy and Comisar.
Windstar on Naples Bay buyers in Zone AE need flood insurance for a federally backed mortgage; NFIP policies in the census block group that contains Windstar ran a median premium of $1,562 for houses and $842 for condominium unit owners in 2025-26, and three-story condominium buildings fall under Florida’s SIRS and milestone laws.
Insurance at Windstar has three layers, and buyers who understand which layer belongs to whom avoid most surprises. The owner of a single-family home or villa insures the whole structure. A condominium unit owner insures the interior and contents, while the condominium association insures the building. And the master association insures master property such as the gatehouse, the dock and the Keewaydin facilities. Flood and wind are separate policies in Florida, and the public data that exists is mostly about flood.
FEMA publishes National Flood Insurance Program (NFIP) policy and claims data by census block group, with addresses removed. Windstar falls in block group 120210107022, which also contains older streets outside the gates, so the figures below are for the census block group that contains Windstar and older neighboring streets, not for Windstar alone.
NFIP policies in force June 2025 to July 2026 in the census block group that contains Windstar, per OpenFEMA NFIP Policies:
Policy type | Median premium | Median total policy cost | Median building coverage |
|---|---|---|---|
Houses and other non-condominium policies | $1,562 | $1,973 | $250,000 |
Condominium unit-owner policies | $842 | $1,159 | $160,000 |
Condominium association master policies | $4,975 | $6,403 | $1,000,000 |
Every one of those in-force policies is rated under FEMA’s current method, Risk Rating 2.0, which prices each building on its own characteristics (elevation, distance to water, replacement cost) rather than on the zone alone. Every policy row also carries Community Rating System class 6, which applies to both Collier County and the City of Naples. Under FEMA’s Community Rating System schedule, class 6 earns a 20 percent premium discount inside the Special Flood Hazard Area and 10 percent outside it.
The claims record is the other half of the picture. OpenFEMA NFIP Claims for the same census block group that contains Windstar and older neighboring streets show:
Storm | Claims | Net paid (about) | Buildings built 1980 or later, a proxy for Windstar-era construction |
|---|---|---|---|
Ian (2022) | 164 claims, 141 paid | $8.77 million | 89 claims, about $1.70 million |
Milton (2024) | 20 claims | $1.17 million | 3 claims, about $3,700 |
Irma (2017) | 12 claims | $0.29 million | not broken out here |
Helene (2024) | 4 claims | $0.21 million | not broken out here |
Two readings follow from those numbers. Ian was the one storm since Windstar’s build-out that produced widespread flood claims on buildings of Windstar’s era, and those buildings still accounted for only about $1.70 million of the roughly $8.77 million paid in the block group, with most of the dollars going to older, lower buildings. Milton, which pushed Naples Bay to 5.77 feet NAVD88 at the north gauge, produced almost nothing on post-1980 buildings. The 1980 filter is a proxy, because FEMA does not publish addresses, so a buyer should ask the seller directly about any flood claim on the specific home and request the claim history through the insurance agent.
Who must buy flood insurance? A federally backed or federally regulated mortgage on a building in the Special Flood Hazard Area, which includes every Zone AE home at Windstar, requires flood coverage. Shaded Zone X buyers, which at Windstar means most of Marina Cove plus the shaded X points at Northstar and Morningstar, are not under the federal mandatory purchase rule, though a lender may still require coverage. Shaded X does not change the evacuation picture: those homes are in Evacuation Zone A like the rest of Windstar.
Most Windstar homes were built between 1984, when Windward Cay delivered the first units, and the early 2000s, according to the year-built field on the Florida Department of Revenue’s statewide cadastral roll. The bulk of that construction predates the first statewide Florida Building Code, which took effect on March 1, 2002. The exceptions are Regatta Landing, built from 2016 to 2021, and later estates and replacement homes in villages such as Harrington Sound and the Island at Southpointe.
Florida wind premiums turn on the roof’s age, shape and attachment and on impact protection for windows and doors, which insurers learn from a wind mitigation inspection; for condominiums, the association’s master policy covers wind on the building and flows into the dues.
Windstar-specific wind premiums are not published. The practical step is simple and should happen early: during the inspection period, get a wind mitigation inspection on a single-family home or villa, ask an insurance agent for a binding quote on the specific address, and for a condominium, ask the association for its current master policy declarations and budget.
Florida law now sets two building-safety requirements for condominiums, created by chapter 2022-269, Laws of Florida and since amended:
Florida’s Department of Business and Professional Regulation explains the rules on its condominium inspections page and collects association filings through its SIRS reporting page.
At Windstar, most condominium buildings are one or two stories and fall outside both rules. The public record shows where the rules do apply:
For any condominium purchase at Windstar, a buyer should request the association’s SIRS and milestone reports (or written confirmation that the buildings are under three habitable stories), check the association’s filing on DBPR’s SIRS reporting page, and read the current budget for how reserves are funded. Those documents, not a summary, decide whether a special assessment is coming.
Windstar on Naples Bay is zoned for Avalon Elementary, Gulfview Middle and Naples High for 2026-27 at every Windstar address the district’s lookup returned, including the City of Naples villages; the state graded Gulfview Middle and Naples High A and Avalon Elementary B in 2026.
School zoning at Windstar is unusually simple. Fifteen addresses, one in each village the Southwest Florida MLS uses, were run through Collier County Public Schools’ address lookup on October 10, 2026, for both the 2025-26 and 2026-27 school years, and every one returned the same three schools with no rezoning flag. That includes the two villages inside the City of Naples. Three of the lookups are linked here as examples: 2488 Breakwater Way at Regatta Landing, 1620 Star Point Lane at Admirals Watch and 2153 Paget Circle at Somerset at Windstar.
Grades are from the Florida Department of Education’s 2025-26 School Grades file, as of September 1, 2026. Drive times are free-flow estimates from the Windstar entrance at Windstar Boulevard and Bayshore Drive, from the OSRM routing service run on October 10, 2026.
School | Address | 2026 grade | Share of possible points | Drive from the Windstar entrance |
|---|---|---|---|---|
3300 Thomasson Dr | B | 57% | about 0.8 mi, 3 min | |
255 6th St S | A | 75% | about 3.5 mi, 8 min | |
1100 Golden Eagle Cir | A | 67% | about 5.0 mi, 11 min |
A little more from the same state file helps read the table. Gulfview Middle has earned an A in every graded year back to 2019. Naples High’s graduation rate for 2024-25 was 94 percent. Avalon Elementary, the closest school to Windstar by far, earned its B with 57 percent of possible points; it is a Title I school, with 89.4 percent of its students counted as economically disadvantaged in the state file. The Collier County district as a whole earned an A in 2026 with 73 percent of points, according to the FLDOE 2026 District Grades file and the district’s own school and district grades page.
Zoning can change, and families should confirm by address. Before signing a contract that depends on a school, check the specific address with the district’s attendance boundaries tool.
Collier County lets families apply to schools outside their zone. The district’s Parental Choice page describes “School Choice under Parental Choice … without respect to or limitations upon their reasons,” alongside a separate out-of-zone route for documented needs or hardships. Seats depend on capacity, so a choice application is a request, not a guarantee.
Three A-rated public schools within a short drive of Windstar are common choice targets, with 2026 grades from the FLDOE school grades file:
Private and parochial options are within a 20-minute drive. Drive times are free-flow from the Windstar entrance (OSRM, October 10, 2026):
School | Drive from the Windstar entrance |
|---|---|
Saint Ann Catholic School, 542 8th Ave S | about 3.6 mi, 9 min |
Seacrest Country Day School, 7100 Davis Blvd | about 4.8 mi, 10 min |
St. John Neumann Catholic High School, 3000 53rd St SW | about 8.2 mi, 18 min |
Community School of Naples, 13275 Livingston Rd | about 9.3 mi, 19 min |
For adult learners and older students, two campuses are close. Lorenzo Walker Technical College on Estey Avenue is about 2.7 miles and 8 minutes away, and the Florida SouthWestern State College Collier Campus on Grand Lely Drive is about 5.3 miles and 12 minutes away.
Windstar on Naples Bay is about 10 minutes from NCH Baker Hospital’s 24-hour emergency department and 5 minutes from a walk-in urgent care on Thomasson Drive, with Collier County EMS Medic 22 stationed about a third of a mile from the Windstar entrance on Bayshore Drive.
Healthcare access is a practical part of any home decision, and Windstar’s location on the Bayshore corridor, close to downtown Naples, keeps the main NCH emergency department about 10 minutes away. Drive times below are free-flow estimates from the Windstar entrance, from OSRM routing run on October 10, 2026; in season, allow more time.
Facility | What it offers | Drive from the Windstar entrance |
|---|---|---|
NCH Baker Hospital Emergency Department, 350 7th St N | emergency department open 24 hours | about 4.0 mi, 10 min |
130-bed hospital with a 24-hour ER | about 6.1 mi, 14 min | |
177-bed hospital | about 9.6 mi, 20 min | |
emergency department with pediatric and obstetric emergency departments listed | about 11.9 mi, 23 min |
NCH reports 713 beds across its Baker and North hospitals combined, per its About page. For a family with children, the detail worth knowing is that NCH North’s location page lists pediatric and obstetric emergency departments, while NCH Baker, the closest ER to Windstar, is the general emergency department nearest the gate.
For the sprained ankle or the sinus infection, the closest walk-in clinic is Physicians Regional East Naples at 4525 Thomasson Drive, about 1.8 miles and 5 minutes from the entrance. Physicians Regional’s urgent care locations page lists it as a walk-in urgent care open from 7 a.m. to 7 p.m. every day. A second option is NCH Medical Group Immediate Care, Southeast at 7717 Collier Boulevard, about 7.2 miles and 15 minutes away.
Emergency response is close. Collier County EMS Medic 22 is stationed at 4375 Bayshore Drive, about 0.3 miles from the Windstar entrance, per the county’s EMS Stations layer.
Pharmacies come with the groceries. Both of the nearest Publix stores list a Publix Pharmacy: Publix at the Shops at Hammock Cove, 4370 Thomasson Drive, about 1.8 miles and 5 minutes away, and Publix at Naples Towne Centre, 3815 Tamiami Trail East, about 2.7 miles and 7 minutes away. Veterans have the Naples VA Clinic at 800 Goodlette Road North, near downtown.
Windstar on Naples Bay is about 7 minutes from Fifth Avenue South, 10 minutes from the Naples Pier and 51 minutes from RSW without traffic, measured from the Windstar Boulevard entrance on Bayshore Drive; homes at the Southpointe end add about 3 to 4 minutes to every trip.
Method: every time on this page is a free-flow drive on OpenStreetMap roads from the public OSRM routing service, run on October 10, 2026, starting at Windstar Boulevard and Bayshore Drive. Free-flow means no traffic and no waiting at signals, so read each figure as “about X minutes without traffic.” In season, from roughly January through April, US 41 and the east-west roads into downtown add time.
Location is one of Windstar’s strongest cards. The community sits on the Bayshore corridor just south of US 41 East, so daily life runs in short trips: groceries, urgent care and the elementary school are all inside 5 minutes, and downtown Naples is inside about 10. The trade-off runs the other way for I-75 and the airport.
Destination | Drive from the Windstar entrance |
|---|---|
Naples Botanical Garden, 4820 Bayshore Dr | about 0.7 mi, 2 min |
Sugden Regional Park | about 1.3 mi, 5 min |
Publix, Shops at Hammock Cove, 4370 Thomasson Dr | about 1.8 mi, 5 min |
Publix, Naples Towne Centre, 3815 Tamiami Trl E | about 2.7 mi, 7 min |
Fifth Avenue South | about 3.1 mi, 7 min |
Third Street South | about 3.6 mi, 9 min |
Waterside Shops | about 8.6 mi, 18 min |
Mercato | about 11.1 mi, 21 min |
about 11.1 mi, 21 min |
The Naples Botanical Garden is close enough to be a neighbor: about 0.7 miles and 2 minutes by car from the Windstar entrance by free-flow routing. Sugden Regional Park, with its lake and its new boardwalk connection to Bayshore Drive, is about 5 minutes away. Fifth Avenue South and Third Street South, the two downtown dining and shopping streets, are each under 10 minutes without traffic. The shopping centers to the north, Waterside Shops and Mercato, are a longer run at 18 and 21 minutes.
Destination | Drive from the Windstar entrance |
|---|---|
Naples Pier (Gulf beach) | about 4.4 mi, 10 min |
Lowdermilk Park (Gulf beach) | about 5.3 mi, 12 min |
Vanderbilt Beach Park | about 12.1 mi, 23 min |
Delnor-Wiggins Pass State Park ($6 per vehicle) | about 14.4 mi, 29 min |
Naples Airport | about 4.4 mi, 11 min |
about 36.5 mi, 51 min | |
I-75 Exit 101 (Collier Boulevard) | about 9.4 mi, 16 min |
I-75 Exit 105 (Golden Gate Parkway) | about 10.9 mi, 19 min |
The Gulf beaches by car are close: the Naples Pier in about 10 minutes and Lowdermilk Park in about 12. Windstar owners also have the master association’s own beach on Keewaydin Island by shuttle, covered in the beach section above, and boat owners can reach the Gulf through Gordon Pass. The private Naples Airport is about 11 minutes away, and RSW, the region’s commercial airport, about 51 minutes in free-flowing traffic. I-75 is the long leg from Windstar: the nearest interchanges are 16 to 19 minutes away.
Where you live inside the gates changes every number slightly. Windstar is a large community, and the Island at Southpointe area at its far southern end adds about 1.3 miles and 3 to 4 minutes to every trip compared with the entrance, while Admirals Watch on the west side adds about 0.8 miles, per the same OSRM routing.
Location is one of the facts that sets a Windstar home’s value, and it is the one an owner cannot change. Sellers who want their village and its convenience priced in can get a free valuation of their Windstar home or Call Jesse direct at (239) 898-6072. Buyers weighing Windstar’s downtown access against communities closer to I-75 can Call Marc at (239) 287-5873 or start with our guide to buying a Naples home with McGreevy and Comisar.
Windstar on Naples Bay is built out, so change comes from outside the gates: the county is marketing its 17-acre arts site across Bayshore Drive, opened a boardwalk to Sugden Park in February 2026, and approved new homes, condominiums and marinas within a mile along Bayshore Drive, Davis Boulevard and US 41 East.
That pipeline matters to a Windstar owner because it shapes the drive in and out of the Bayshore Drive entrance and adds new-construction choices that compete with Windstar resales. Windstar sits inside the Bayshore Gateway Triangle Community Redevelopment Area (Bayshore CRA boundary layer), which covers about 1,800 acres and collected $5,387,900 in tax-increment revenue in 2025 (2025 Collier CRA Annual Report, approved March 24, 2026). That increment pays for most of the work below.
Every distance in this section is a straight-line distance from the edge of the Windstar PUD, computed from Collier County’s CityView project layer and PUD layer on October 10, 2026, unless the sentence says “from the gate”.
The single largest open question on Windstar’s doorstep is the county-owned 17-acre site directly across Bayshore Drive from the Windstar entrance, about 0.16 miles from the gate. The land carries its own zoning, the Cultural Arts Village at Bayshore MPUD adopted as Ordinance 12-21 in 2012, recorded on the county PUD layer. The approved entitlements allow up to 40 residential units, 35,000 square feet of commercial space, an 84,000 square foot parking garage and a 350-seat performance theatre, as summarized in the county’s solicitation for the site.
On July 15, 2026 the Bayshore Gateway Triangle CRA posted Invitation to Negotiate 26-8663 for three outparcels on the 17-acre site, after Board authorization on July 14, 2026. Proposals were due August 31, 2026. The solicitation asks proposers to state how they want to take the land (fee simple, ground lease, phased or hybrid), to prioritize a performance space or CRA office, arts or incubator space, and to comply with the Bayshore Zoning Overlay that governs the Bayshore Drive frontage.
As of October 10, 2026, no award under ITN 26-8663 had been reported. The result decides what fills the view at the main entrance for the next decade: a performance venue with structured parking, a residential and retail mix within the MPUD caps, or some combination.
The part of the 17-acre plan that is already finished is the walk. The Bayshore Boardwalk linking Bayshore Drive to Sugden Regional Park opened on February 26, 2026. It runs 1,750 feet and is 15 feet wide, about 400 feet of brick promenade followed by about 1,350 feet of boardwalk over wetland and lake, with a lakeside observation deck (Naples Press, “Exploring the new Bayshore to Sugden Park connector”). Parking is on the Sugden side; the trailhead on Bayshore Drive is about 0.16 miles from the Windstar gate.
The 2025 CRA annual report carries a budget line of $3,598,662.76 for the boardwalk; that is the CRA’s budget figure, not an audited final cost.
Inside the gates nothing is left to build (both Windstar PUDs are listed as built out on the county PUD layer), so the new-construction alternatives a Windstar buyer weighs are all outside. These are the approved or advertised residential projects with stated unit counts inside about one mile of Windstar’s edge.
Project | What it is | Status (date of record) | Distance from Windstar’s edge | Source |
|---|---|---|---|---|
Windward Landing RPUD (a separate new project, not Windstar’s Windward Cay) | Up to 90 single-family detached homes on 71.46 acres south of Holly Avenue and west of the terminus of Bayshore Drive; rezoned from RSF-3 and A | Planning Commission hearing May 7, 2026; Board of County Commissioners hearing June 9, 2026; county zoning layer records Ordinance 26-19 | 0.64 mi | BCC legal ad; CCPC legal ad; zoning layer_view/FeatureServer/1) |
The Halcyon (Davis Brookside MPUD) | 66 condominium units and a 120-slip marina on 8.27 acres on the north side of Davis Boulevard off Rock Creek; repealed Ordinance 23-42 | BCC hearing September 23, 2025; Ordinance 25-39 | 0.95 mi | |
Mini-Triangle MPUD (Metropolitan Naples) | Up to 507 multifamily units on 6.70 acres at Davis Boulevard and US 41 after the 2026 amendment added 1.35 acres and 16 units | BCC hearing July 14, 2026 | 0.79 mi | |
Courthouse Shadows apartments | 300 rental units at 3368 Torrente Avenue | Ordinance 2019-40; site plan amendment listed as pre-construction | 0.54 mi | CityView layer; zoning layer_view/FeatureServer/1) |
Metro South, 3010 Tamiami Trail East | Up to 8 residential units and 3,860 square feet of commercial space on 0.64 acres, about 295 feet east of Bayshore Drive | Mixed-use project approved by BCC Resolution 25-017, January 14, 2025 | 0.42 mi | |
Mangrove Row, 2766 Arbutus Street | 8 units on 0.98 acres under a density bonus | Hearing Examiner, February 2025 | 0.15 mi | |
Isles of Collier Preserve phases | Single-family phases of the master-planned community east of Bayshore Drive | Phase plats recorded as complete or under inspection in CityView | 0.68 to 0.96 mi | CityView layer |
Windward Landing is the one name buyers mix up. It is a separate 2026 rezoning south of Windstar, not Windward Cay, the 48-unit condominium village inside the Windstar gates. The county record states a maximum of 90 single-family detached homes, and the ordinance title names no builder. On August 11, 2026 the Board was also advertised to hear an ordinance expanding the Bayshore Beautification MSTU boundary to take in Windward Landing (BCC legal ad for the MSTU boundary expansion); the outcome of that hearing was not confirmed in the records read for this page.
The Halcyon is the waterfront project in the radius: the September 23, 2025 BCC legal ad approves 66 multifamily units and a 120-boat-slip marina on Rock Creek, which feeds Naples Bay, and press coverage targets a construction start around the first quarter of 2027 (Gulfshore Business, March 13, 2026). For a Windstar condominium seller, it is a new-construction alternative a buyer may tour in the same week.
Isles of Collier Preserve is the nearest master-planned neighbor in the same Bayshore corridor; its phase plats sit 0.68 to 0.96 miles from Windstar’s edge on the county CityView layer. Buyers comparing a resale in Windstar with newer construction in a gated master plan often look at both, and our Isles of Collier Preserve community guide covers that community’s fees, flood mapping and market in the same format as this page.
The new supply within a mile is mostly multifamily along US 41 and Davis Boulevard, one low-density single-family rezoning to the south and one condominium marina on Rock Creek. None of it adds a golf course, a private beach or a master gate, so Windstar resales compete on a different footing.
The road outside Windstar is in a quiet phase. FDOT finished resurfacing US 41 past the Bayshore Drive intersection under contract T1778 on November 8, 2023 (FDOT construction contracts layer), and its current work program programs US 41 PD&E studies west of State Road 84 for fiscal year 2027, plus a “Bayshore CRA Sidewalk” safety project with preliminary engineering the same year. We found no FDOT capacity project at the US 41 and Bayshore Drive intersection.
Stormwater is the biggest dollar item. The CRA’s Bayshore Phase I stormwater project on Becca, Pine and Weeks streets carries a total of about $9.2 million ($9,195,036.95) in the 2025 CRA annual report, with construction targeted for 2027. It drains neighborhoods outside Windstar; Windstar’s own lakes are maintained by the master association.
One waterway item touches a Windstar village: Regatta Landing’s parcels pay the 1.0-mill Haldeman Creek MSTU, and the CRA’s Haldeman Creek projects page reports that a 2025 survey found dredging “not currently warranted”.
The only construction permits inside Windstar’s gates in the county record are the Windstar Club’s: Clubhouse Expansion (PL20210001972), Temporary Fitness Facilities (PL20220004780) and Fitness Center (PL20240013453) on the county CityView layer. The club says on its fitness center page that a new fitness center is due in 2026; the county still lists that site plan under site inspection, so confirm its opening with the club.
The Windstar PUD has not been rezoned since Ordinance 93-23 in 1993, and a search of the Collier Clerk’s public notice site for “Windstar” on October 10, 2026 returned no legal notices naming the community.
Windstar is inside the Bayshore CRA but outside the Bayshore Zoning Overlay, which begins at the Bayshore Drive frontage (zoning exception layer): Windstar property contributes CRA tax increment, but the overlay’s mixed-use rules do not apply inside the gates.
Windstar on Naples Bay’s master declaration allows leases of at least 30 days or one calendar month and no more than one year, with no more than three leases a year, and every village can be stricter; pets must be leashed, and all exterior changes need neighborhood and then master architectural approval.
Windstar runs on two layers of rules. The master layer is the master association’s recorded document compilation (the 2009 restated master declaration and its amendments) plus the master Rules and Regulations approved May 15, 2018; the village layer is each association’s own declaration and rules, which prevail where they are stricter. Where a village document is not public, that village’s Declaration and Rules govern, and a buyer should ask for them before the inspection period ends.
The master leasing covenant is Article 7.1 of the master declaration, rewritten by the owners at a members’ meeting on May 7, 2020 and recorded in the 2020 amendment at Official Records Book 5764, Page 966 (master document compilation). Its terms apply to every home inside the gates:
The master association’s 2022 lease application form sets the administrative fee at $145 per lease and says that fee covers the tenant’s Keewaydin registration, gate access and a remote opener; the form asks for the neighborhood association’s approval to be attached, which is why a lease in a village with its own approval step has to clear the village first. The 2018 master rules add two practical points: owners must be current on all dues before a lease is approved, and tenants receive their own gate transponder for the lease term, so an owner may not simply hand over the owner’s transponder (2018 Rules and Regulations).
Short-term and vacation rentals are not allowed anywhere in Windstar. With a 30-day or one-month floor, no transient tenants and no room rentals, weekly and nightly rentals are outside the recorded covenant. For an owner thinking about Windstar on Naples Bay rentals, the realistic model is a seasonal lease of one to several months, up to three times a year at the master level.
Village layers tighten the master rule in the villages whose documents are public:
Village | Lease minimum | Leases allowed | Approval and fees | Source |
|---|---|---|---|---|
Master rule (every home) | 30 days or one calendar month; one year maximum | 3 per calendar year | 20 days’ notice; $145 master application | Master declaration Art. 7.1; lease application |
Regatta Landing | 30 days | 2 in any 12 months | Association process first, then the master application; $1,000 fine per violation | Regatta Landing declaration; Regatta Landing rules, 9/5/2025 |
Compass Point South | one month | 3 a year | Board prior approval; application 20 days ahead; no subleasing | Compass Point South Q and A, 2021; Compass Point South rules |
Somerset at Windstar | the master 30-day or one-month minimum applies (see below) | 3 a year | Somerset application and fee | Somerset at Windstar rules, 2013; master declaration |
Other 12 villages | Declaration and Rules govern | Declaration and Rules govern | Ask the association | each village’s recorded declaration |
Regatta Landing is the tightest of the published layers: its amended and restated declaration allows no more than two leases in any rolling 12 months, which is stricter than the master’s three per calendar year, and its declaration also limits occupancy to two persons per bedroom plus one per den, except temporary guests. Somerset at Windstar’s posted 2013 rules state a 28-day minimum, but those rules predate the recorded 2020 master amendment, and the recorded master minimum of 30 days or one calendar month applies to every Windstar home, Somerset included. A Somerset owner should plan every lease on the master minimum.
The master pet rule is short. The 2018 Rules and Regulations require pets to be walked on leashes and never to run free, require owners to remove waste immediately, and strongly discourage feeding feral cats. Three location rules follow from the same document:
The master rules as published in 2018 set no weight, number or breed limit, so those limits come from the villages. Two villages publish theirs. Compass Point South allows owners one dog or one cat of 25 pounds or less, and tenants may not keep pets at all (Compass Point South Q and A, 2021; Compass Point South rules.pdf)). Regatta Landing allows two pets, cats or dogs, each under 60 pounds, leashed and only in designated areas (Regatta Landing rules, September 5, 2025). Somerset at Windstar’s 2013 rules allow dogs, cats and non-exotic household pets, leashed and not left on lanais (Somerset at Windstar rules). For the other 13 villages, the Declaration and Rules of that village govern; a buyer with a large dog or more than one pet should get the village’s written rule before writing an offer.
Assistance animals are a separate question governed by fair-housing law, not by an association’s pet cap; buyers who need one should raise it with the association in writing.
Windstar is gated. The master association’s 2025 annual meeting deck names four master gates in its reserve spending, the Main Gate on Windstar Boulevard, the Lighthouse Gate, the Gulfstar Gate and the Regatta Gate, and gatehouse maintenance was the association’s second-largest operating line in 2024. The rules that govern who gets through them sit in the 2018 Rules and Regulations:
Regatta Landing adds its own gates. Its declaration provides a northwest gate from Haldeman Creek Drive owned and run by the condominium association, which other Windstar residents may pass on foot or by bicycle, and a southeast gate from Lakeview Drive operated by the master association with vehicle use limited to Regatta owners and dock-slip owners (Regatta Landing declaration). The Island at Southpointe has its own gated entrance over a stone bridge.
Gate and shuttle phone numbers change; owners get current contacts from the master association’s office at 1700 Windstar Boulevard.
Every exterior change in Windstar goes through two reviews. Article 8 of the master declaration creates the master Architectural Review Committee, and no new construction, visible exterior change, paint, sign, grading, excavation or landscaping may happen without its approval or the board’s (master declaration). If the committee does not act within 30 days, the matter goes to the board. The same declaration requires 22 days’ notice to the Windstar Club board before construction within 50 feet of club property; that is a notice requirement, not a club veto.
The master’s Design Guidelines and Tree Policy, approved May 26, 2022, set the process and the standards:
Step or standard | What the 2022 guidelines require |
|---|---|
Order of review | Written neighborhood approval first, then the master committee |
Lead time | Submit at least 30 days before the planned start; a survey is required for any footprint change |
Effective date | Approval takes effect on the 7th day, after an appeal window |
Deadlines | Start within 6 months of approval and finish within 1 year |
Like-for-like replacement | One week’s notice |
Hurricane protection | Clear, white or matched to the trim |
Windows | Match the existing windows |
Generators | Need approval and landscape screening |
Propane tanks | Buried, per county code |
Lawns | Substantial or total removal of turf and replacement with mulch or gravel is prohibited |
Trees | Canopy trees set back from structures, drives and walks; removal only for qualified reasons, with mitigation |
The committee is active. The master association’s 2025 Committee Reports Binder reports that the Architectural Review Committee met 13 times in the 2024 to 2025 year, and that it reviewed the Windstar PUD’s minimum building standards with potential demolition and new construction in mind. Typical requests are paint, roofs, driveways, lanai cages, generators and tree removals. For a buyer planning a renovation, the timeline to budget is the village review plus at least 30 days at the master level plus the 7-day appeal window, before any county permit.
Master roads in Windstar (Windstar Boulevard, Haldeman Creek Drive, Yacht Harbor Drive, Gulfstar Drive, Lighthouse Lane and Star Pointe Lane) are private roads run by the master association, and the 2018 Rules and Regulations set the rules on them:
If you are leasing, renovating or buying with a boat, a big dog or an EV, these are the rules that decide the purchase; get the village’s own documents during the inspection period. Sellers who want to know how these rules affect their buyer pool can request a free home valuation or call Jesse direct at (239) 898-6072. Buyers who want the village documents pulled before writing an offer can call Marc at (239) 287-5873 or start with our buyer representation guide.
Windstar on Naples Bay and Royal Harbor are both Naples Bay boating neighborhoods south of the US 41 bridge, but they answer different buyers: Windstar is gated, golf-centered and run by a master association over 16 villages, while Royal Harbor is an ungated City of Naples canal neighborhood with no mandatory HOA.
The two get mixed up more than their maps justify. Both sit on the east side of Naples Bay, both reach the Gulf through Gordon Pass without passing under the fixed US 41 bridge, both share Gulfview Middle and Naples High, and both are mapped Zone AE with base flood elevations of 8 or 9 feet and sit in Collier Hurricane Evacuation Zone A. So the choice between them rarely turns on schools, flood or the boat ride. It turns on governance, product and price: a gate, a golf club and a master association with village associations on one side, and a single-family canal lot with your own dock and no mandatory association on the other. The Royal Harbor figures below come from our live Royal Harbor neighborhood guide as read on October 10, 2026, where each one carries its own primary source; the Windstar figures come from the records cited throughout this page.
Factor | Windstar on Naples Bay | Royal Harbor |
|---|---|---|
Homes | 618 homes and condominiums in 16 villages (Florida DOR 2026 roll and Collier address points) | 386 homes on three recorded plats plus 25 vacant homesites |
Product | Condominiums, attached villas, coach homes, single-family courtyard and pool homes, bayfront estates | Single-family canal homes, plus the condominiums of The Row at Royal Harbor |
Gated | Yes, four master gates (Main, Lighthouse, Gulfstar, Regatta) | No |
Golf | Private 18-hole Tom Fazio course; optional equity Windstar Club | None |
Mandatory association | Master association, $4,130 per home in 2025, plus a village association | No mandatory HOA; a voluntary association at $50 a year (The Row has its own condominium association) |
Boating | Southpointe Marina, Regatta Landing’s Haldeman Creek docks, private slips at Admirals Watch and the Island at Southpointe; bay docks run south to Gordon Pass without passing under the US 41 bridge | Private canal docks opening onto Naples Bay, on the same side of the US 41 bridge (10-ft clearance) |
Beach | Master-owned beach property on Keewaydin Island, reached by the association’s shuttle | No private beach stated; see our Royal Harbor page |
Jurisdiction | Mostly unincorporated Collier County; Admirals Watch and the Island at Southpointe are in the City of Naples | City of Naples, ZIP 34102 (land east of Sandpiper Street is unincorporated) |
Flood | 58 of 68 sampled points Zone AE (BFE 8 or 9 ft NAVD88), 10 shaded X; every point Evacuation Zone A | Zone AE, BFE 9 ft on 342 of 418 parcels and 8 ft on 76; Evacuation Zone A |
Schools (zoned) | Avalon Elementary, Gulfview Middle, Naples High | Lake Park Elementary, Gulfview Middle, Naples High |
Era | First homes 1984; last new homes 2021 (Regatta Landing) | Platted in the 1950s |
12-month market | 52 closed sales, median $1,200,000 (Southwest Florida MLS, October 13, 2025 to October 13, 2026) | 21 single-family closings, median $2,975,000 (Southwest Florida MLS, September 25, 2025 to September 24, 2026) |
Sources for the Windstar column are the records cited throughout this page: the Florida DOR 2026 roll and Collier address points (homes), the master association’s 2025 annual meeting deck (gates and assessment), NOAA’s Coast Pilot (bridge), FEMA’s flood layer and the Collier evacuation layer (October 10, 2026) and the Collier County Public Schools address lookup (2026-27).
Read the market row carefully. The two medians come from different 12-month windows, and they measure different things: Windstar’s $1,200,000 median mixes 36 condominium sales with villas and detached homes, while Royal Harbor’s $2,975,000 median counts single-family canal homes only. The fairer comparison is Windstar’s detached single-family segment, which had eight sales from $1,375,000 to $6,750,000 in the same Windstar window and a $1,600,000 median across 22 sales over 24 months (grouped by McGreevy and Comisar from the Southwest Florida MLS rows), or Windstar’s waterfront estates, where single sales ran from $2,075,000 at Harrington Sound to $6,750,000 at the Island at Southpointe. In other words, a Royal Harbor canal home and a Windstar condominium are not competing for the same buyer; a Royal Harbor canal home and a Windstar estate on the water sometimes are.
Choose Windstar on Naples Bay if you want a staffed gate and a master association that runs the roads, lakes and common grounds; you want golf available on a private Tom Fazio course without being forced to join (the Windstar Club is optional); you want a condominium, villa or coach-home price point that Royal Harbor’s single-family market does not offer, with condominium, villa and coach-home village medians over 24 or 36 months from $503,500 at Compass Point South to $1,700,000 at Yacht Harbour Cove (the Admirals Watch bayfront condominiums ran higher, at $2,375,000 to $3,625,000 across three sales in the last 12 months); you want a private beach reached by the association’s shuttle rather than by your own boat; or you want a condominium or villa where a village association maintains the buildings and grounds you share.
Choose Royal Harbor if you want a single-family home on a canal with your own dock behind it; you want no mandatory homeowners association and no architectural committee between you and a renovation; you do not need golf or a gate; and you are comfortable with a single-family price point that, on our Royal Harbor page’s own window, sat near $3 million at the median.
Consider both if you are shopping waterfront single-family above $2 million: Windstar’s Admirals Watch, Harrington Sound and Island at Southpointe homes and Royal Harbor’s canal homes reach the same bay and the same pass, and the deciding question is whether you want a gate, a club option and a master association or a private canal lot and no mandatory dues.
Sellers on either side of that fork can get a pricing read against both markets with a free home valuation, or call Jesse direct at (239) 898-6072; buyers comparing the two can call Marc at (239) 287-5873 and read how we represent buyers in Naples.
Windstar on Naples Bay’s strengths are its bay setting, gate, optional golf club, marina, Keewaydin beach and wide price range; its trade-offs are Zone AE flood exposure and Evacuation Zone A, two association layers of fees, older 1980s and 1990s buildings, and a club whose current costs are unpublished.
Every item below is tied to a record cited elsewhere on this page. A con is not a reason to skip Windstar; it is a question to answer for the specific home before the inspection period ends.
If the pros fit and the cons are answerable for a specific home, the next step is the village documents and the elevation certificate. Thinking of selling? Get a free Windstar home valuation or call Jesse direct at (239) 898-6072. Buying? Call Marc at (239) 287-5873, and see how we guide buyers through the documents before an offer.
Eleven of Windstar on Naples Bay’s 16 villages have the sales depth and their own association to carry a dedicated neighborhood page; Leeward Cay is covered with Somerset at Windstar, Spyglass Pointe and the Island at Southpointe with the Harrington Sound estates, and Northstar and Morningstar are covered here on the Windstar page.
Each village has its own association, fees and rules, which is why one community page cannot answer every village-level question; the village sections earlier on this page hold each one’s product, association, build years and flood sample. The table lists the eleven pages and each village’s sales in the 12 months to October 13, 2026 (Southwest Florida MLS).
Neighborhood | 12-month sales (MLS, to Oct 13, 2026) | Page covers |
|---|---|---|
Regatta Landing | 9 sales, $1,090,500 to $1,849,000 (24 months: median $1,310,000) | Regatta Landing |
Marina Cove | 6 sales, $507,500 to $745,000 (24 months: median $646,000) | Marina Cove |
Spinnaker Pointe | 5 sales, $525,000 to $905,000 (24 months: median $630,000) | Spinnaker Pointe |
Somerset at Windstar | 5 sales, $660,000 to $1,300,000 (24 months: median $1,095,000) | Somerset at Windstar, also covering Leeward Cay (3 sales, $800,000 to $1,270,000) |
Yacht Harbour Cove | 5 sales, $1,200,000 to $2,250,000 (36 months: median $1,700,000) | Yacht Harbour Cove |
Windward Cay | 4 sales, $350,000 to $1,075,000 | Windward Cay |
Compass Point South | 2 sales, $430,000 and $508,000 (36 months: median $503,500) | Compass Point South |
Ketch Cay | 3 sales, $1,375,000 to $1,750,000 | Ketch Cay |
Clipper Cove | 2 sales, $1,480,000 and $1,625,000 | Clipper Cove |
Admirals Watch | 3 sales, $2,375,000 to $3,625,000 | Admirals Watch |
Harrington Sound | one sale, at $2,075,000 (thin) | Harrington Sound estates, also covering Spyglass Pointe (one sale, at $1,775,000) and the Island at Southpointe (one sale, at $6,750,000) |
Sales figures: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026; a single sale is too thin to read as a market rate.
If you’re searching for the best Windstar on Naples Bay listing agent, or thinking, ‘I need to sell my house in Windstar on Naples Bay’… Jesse McGreevy and Marc Comisar price Windstar homes village by village, because a Compass Point South condominium and an Island at Southpointe estate share a gate and nothing else.
Start with our guide to selling your home in Naples, then call us for the Windstar-specific read.
McGreevy and Comisar are the #5 real estate team in Florida in the 2026 RealTrends rankings. In Windstar, the market a seller is pricing into looks like this: 52 closed sales, $70,378,500 in volume, a $1,200,000 median and a top sale of $6,750,000 in the 12 months to October 13, 2026 (Southwest Florida MLS). Typical days on market (59, median) and the sale-to-list ratio (94.7%, median) come from the same MLS window.
That spread is the whole selling problem in Windstar. A $1,200,000 community median tells a seller almost nothing when sales in the same window run from $350,000 at Windward Cay to $6,750,000 at the Island at Southpointe and no village reaches 10 sales. What sells a Windstar home is a price built from its own village’s closed sales, its flood zone and elevation certificate, its association fees and reserves, and what it offers that its neighbors do not: a slip, a lake or bay view, a newer roof, a renovated kitchen. Windstar sellers also field questions buyers do not ask in most Naples communities, about club membership, two layers of estoppel certificates, Keewaydin access and condominium inspections, and a listing that answers them up front saves days in negotiation.
McGreevy and Comisar is a top-reviewed Windstar realtor, and every quote below is a five-star review on our Google Business Profile.
★★★★★ “He met us within 20 minutes to see it and we loved it. We worked with him on the offer and the transaction was seamless!” Verified Google review
★★★★★ “Marc’s attention to detail and deep understanding of the Southwest Florida market gave us so much confidence.” Verified Google review
Get a free Windstar on Naples Bay home valuation built from the village’s own closed sales, not the community-wide median. Or call Jesse direct:
Ranked by the highest sale, since no village reached 10 sales in the window and a median would be too thin, the top of the Windstar market in the 12 months to October 13, 2026 (Southwest Florida MLS) was:
Village | Sales | Sales listed | Range |
|---|---|---|---|
Island at Southpointe (MLS name Southpointe Yacht Club) | 1 | one sale, at $6,750,000 (thin) | |
Admirals Watch | 3 | $2,375,000, $2,935,000 and $3,625,000 | $2,375,000 to $3,625,000 |
Yacht Harbour Cove | 5 | $1,200,000, $1,300,000, $1,610,000, $1,700,000 and $2,250,000 | $1,200,000 to $2,250,000 |
Harrington Sound | 1 | one sale, at $2,075,000 (thin) | |
Regatta Landing | 9 | nine sales, too few for a median; 24 months: 16 sales, median $1,310,000 | $1,090,500 to $1,849,000 |
Spyglass Pointe | 1 | one sale, at $1,775,000 (thin) | |
Ketch Cay | 3 | $1,375,000, $1,525,000 and $1,750,000 | $1,375,000 to $1,750,000 |
Clipper Cove | 2 | $1,480,000 and $1,625,000 | $1,480,000 to $1,625,000 |
Three of those rows are single sales, which are too thin to read as a market rate for the village. The pattern that does hold across the window is that water and detached product sit at the top: six of the 52 sales closed at $2,000,000 or more, three at Admirals Watch and one each at Harrington Sound, the Island at Southpointe and Yacht Harbour Cove. If your home is in a village with one or two sales in the window, the valuation has to lean on the closest comparable product elsewhere in Windstar, adjusted for the village’s fees and flood zone.
Not automatically, because the membership is not tied to the house. Windstar is not bundled: the Windstar Club says residents within the gates are not required to be members, and Section 1.5 of the master declaration gives no owner club rights by owning a home. Your membership is a separate equity relationship with Windstar Club, Incorporated, and what happens to it when you sell (resignation, transfer to your buyer, any equity refund and when dues stop) is set by the club’s bylaws and membership documents, which the club gives to members and prospective members rather than publishing. Before you list, ask the club’s membership office for the current resignation and transfer terms in writing, so your buyer knows whether joining means a new initiation or a transfer from you.
At least two, and sometimes three. Every Windstar home belongs to the master association, which issues its own estoppel certificate stating the master assessment balance and any amounts due; most homes also belong to a village association or condominium, which issues a second certificate for its own assessments (master declaration). If a Regatta Landing dock slip goes with the sale, the slip transfers by assignment of the Dock Slip Certificate on the dock association’s form, recorded as Exhibit P at Official Records Book 5448, Page 1149 (Regatta Landing Dock Slip Certificate Assignment form), which brings the dock association into the closing too. Estoppel fees are set by each association within the limits of Florida law, and none of Windstar’s associations publishes its fee schedule. One more line to watch: the master board proposed a resale capital contribution in 2023, and the amendment certificate recorded in January 2024 does not contain one; the master estoppel certificate is where any transfer charge would appear. Order the certificates as soon as you are under contract, because each one has its own turnaround.
In Collier County, the buyer customarily pays for the owner’s title insurance policy, and the purchase contract controls. That is the opposite of the custom in some other Florida counties, so a seller relocating from elsewhere should not budget for it as a seller cost. The seller’s usual closing costs are the brokerage commission (which is negotiable), Florida documentary stamp tax on the deed, payoff of any mortgage, prorated taxes and association assessments through closing, and the estoppel certificates described above. Your title agent’s settlement statement is the final word on each line.
It can, but there is no public sales record that prices it. Southpointe Marina slips are separate deeded parcels: the 2026 county roll carries 73 slip parcels at the marina, and their 2026 preliminary county just value has a median of $251,497 per slip parcel (Florida DOR 2026 preliminary roll). That is an appraisal figure, not a sale price, and slip sale prices are not in the MLS extract behind this page. Regatta Landing slips work differently: they are held by Dock Slip Certificate through Regatta Landing Dock Slip Association, Inc., outside the condominium and its assessments (Regatta Landing declaration), and transfer by assignment. At Admirals Watch, the eight slips belong to the condominium. In practice, a slip widens the buyer pool for a Windstar home, and how much it adds to the price depends on the slip’s size, the boat it fits and what comparable slips have recently traded for, which is a question for the marina or dock association and the listing analysis rather than a formula.
Yes, for any condominium building three habitable stories or higher, which needs a structural integrity reserve study at least every 10 years (s. 718.112, Florida Statutes) and a milestone inspection in the year it turns 30 (s. 553.899).
In Windstar, the county’s milestone inspection layer shows Windward Cay buildings 4450, 4600 and 4650 Yacht Harbor Drive and Compass Point South’s four buildings as “Milestone Completed, Cycle Completed”, next inspection 2033, and Compass Point South posts its Structural Integrity Reserve Study dated May 29, 2024. A seller who has the association’s current SIRS, milestone report and reserve funding in hand before listing takes the biggest condominium objection off the table before the first showing.
These are the official Windstar on Naples Bay documents a buyer or seller is most likely to need, each linked to the association, club, county or state site that publishes it. Village documents not listed here come from that village’s association.
Document | What it is | Official link |
|---|---|---|
Master declaration, bylaws, articles and amendments | Second Amended and Restated Master Declaration (OR 4512 PG 2575), the 2013 Regatta annexation, the 2020 leasing amendment and the December 2023 amendment, compiled January 24, 2024 | |
Master Rules and Regulations (2018) | Roads, gates, guests, pets, Keewaydin, lakes, signs, vehicles and leasing rules, approved May 15, 2018 | |
Design Guidelines and Tree Policy (2022) | Architectural review process and exterior standards, approved May 26, 2022 | |
2025 Annual Meeting outline | 2025 assessment by fund, 2024 results, reserves, gates and the Hotwire report | |
Keewaydin booking, cancellation and slip policies | Shuttle booking rules, party size, cruise prices and the private-boat dock permit, revised December 16, 2025 | |
Master lease application | The $145 master lease application with the 20-day notice rule | |
Regatta Landing declaration | Amended and Restated Declaration of Condominium with the last amendment in 2022 | |
Regatta Landing rules (2025) | Leasing, pets, gates, parking and decoration rules, September 5, 2025 | |
Regatta Landing dock slip certificate assignment | Form for transferring a Regatta Landing dock slip (Exhibit P, OR 5448 PG 1149) | |
Compass Point South Q and A (2021) | Quarterly dues, leasing and pet rules for Compass Point South | |
Compass Point South SIRS (2024) | Structural Integrity Reserve Study dated May 29, 2024 | |
Somerset at Windstar rules (2013) | Leasing, pets and fishing rules posted April 8, 2013 | |
Windstar Club scorecard | Yardages, course ratings and local rules for all eight sets of tees | |
Ordinance 93-23 | The controlling Windstar PUD ordinance, adopted May 11, 1993 (549 units, 320.6 acres) | |
Ordinance 88-82 | Southpointe Yacht Club PUD, adopted October 25, 1988 |
These are the questions buyers ask most often about Windstar on Naples Bay, answered from the recorded association documents, county and state records, the Windstar Club’s own pages and the Southwest Florida MLS. Each answer uses the same figures, dates and caveats as the section of this page that covers the topic in depth.
Windstar on Naples Bay is a gated golf and boating community of 618 homes and condominiums in 16 villages in East Naples, ZIP 34112, per the Florida Department of Revenue 2026 preliminary tax roll. Every owner belongs to Windstar on Naples Bay Master Association, Inc., while the Windstar Club, an equity club with a Tom Fazio golf course, is optional (Windstar Club, Our Club). The community also includes Southpointe Marina on the bay and a master-owned beach on Keewaydin Island reached by the association’s shuttle boat (master association, Keewaydin Beach and Shuttle).
Windstar’s main entrance is Windstar Boulevard at Bayshore Drive in East Naples, per the county site address points layer. Ordinance 93-23 (May 11, 1993) places the Windstar PUD about one mile south of US 41 East and west of Bayshore Drive, with Haldeman Creek along its north edge and Naples Bay along its west edge. Naples Botanical Garden is about 0.7 miles and 2 minutes by car from the entrance, and Fifth Avenue South about 3.1 miles and 7 minutes, measured with OSRM free-flow routing on October 10, 2026.
No. Windstar on Naples Bay shares a name with the cruise line and nothing else; it is a residential community in East Naples. Windstar Development Company filed the WINDSTAR and WINDSTAR ON NAPLES BAY service marks for the community on May 6, 1985 (Justia Trademarks record). The community’s official sites are the Windstar Club site and the master association site.
Most of Windstar is unincorporated Collier County; two bayfront villages, Admirals Watch and the Island at Southpointe, lie inside the City of Naples, according to the county City Limits layer and the FEMA political jurisdictions layer. The split shows on the tax bill: for tax year 2025, code 0063 (most of Windstar) carries 12.6162 mills, code 0111 (Regatta Landing) 13.6162 mills and code 0004 (the two City of Naples villages) 9.0514 mills (2025 Collier Taxing Authority Code Descriptions, dated October 3, 2025). Your mailing address says “Naples” either way.
Windstar holds 16 residential villages with 618 homes and condominiums on the Florida DOR 2026 preliminary roll: nine condominium villages with 428 units (ten recorded declarations, per the DBPR condominium extract) and seven homeowners-association villages with 190 homes. You will see other counts. The Southwest Florida MLS recorded sales under 15 neighborhood names in the 12 months to October 13, 2026 because Morningstar had no closed sale and the MLS files the Island at Southpointe as “Southpointe Yacht Club.” The master association’s neighborhoods index lists 17 names because it adds the Southpointe marina slips, which are a boat-slip group rather than a village, and the club’s “15 diverse neighborhoods” on its real estate page is the club’s own description.
The Windstar PUD covers 320.6 acres under Ordinance 93-23, adopted May 11, 1993. Several parcels sit outside that PUD but inside the gates or the master association: the 16.51-acre Southpointe Yacht Club PUD under Ordinance 88-82 (October 25, 1988), the Regatta Landing tract on Haldeman Creek annexed in 2013 (master association document compilation), the City of Naples bayfront parcels, and about 5 acres the master association owns on Keewaydin Island (county parcels of 2.68 and 2.74 acres on the Collier parcels layer). Each of those is a separate record, so we cite them one by one rather than adding them into a single total.
Windstar began as the “Fisherman’s Cove” PUD, approved by Ordinance 81-40 on August 25, 1981 on a petition by Whispering Pines, Inc. Ordinance 82-54 (July 13, 1982) re-titled it Windstar for Windstar Development Company, and WS Realty, Inc. petitioned the 1993 rewrite to a 549-unit plan under Ordinance 93-23. The first homes, at Windward Cay, date to 1984, and the last new village homes, at Regatta Landing, to 2021, per the year-built field on the Florida Statewide Cadastral layer (DOR 2026 roll).
No. Windstar is not bundled: buying a home does not make you a club member. The Windstar Club’s FAQ says, “Residents within the gates are not required to be Members. Windstar is an equity, Member-owned golf and Country Club that accepts non-resident Members.” Section 1.5 of the recorded master declaration (master association document compilation) adds that no owner gains any right to use a Recreational Association’s facilities simply by owning a unit, and the Regatta Landing declaration states, “Membership in the Club is not mandatory.”
The most recent figures the club has published are its 2023 resident offer, attached to the master association’s October 2023 newsletter (2023 club fee pages). On that 2023 schedule, Social membership dues were $6,645 a year, billed $1,662 a quarter, and Social Summer Golf dues were $9,545 a year, billed $2,387 a quarter, with a food and beverage minimum of $1,400 for a family or $700 for a single member. A 2023 Social family membership therefore cost $18,045 in year one: $10,000 initiation, $6,645 dues and the $1,400 food minimum, which is spending on meals rather than a fee lost. The club has not published a 2026 schedule; current initiation, dues, transfer and refund terms come from the club’s membership office and its membership documents.
On the club’s 2023 published schedule, the Social initiation fee was $10,000 (with a resident special of $3,000 through December 31, 2023) and the Social Summer Golf initiation was $20,000; the same pages list a “Full Golf Membership Contribution ($85,000)” (2023 club fee pages). Those are 2023 figures. The club has not published a 2026 schedule, and equity refund and transfer terms sit in the club’s membership documents, so ask the club’s membership office for the current figures before you write an offer that depends on them.
Yes on both. Windstar Club, Incorporated was filed with the state in December 1983 (Sunbiz N00119) and today describes itself as “an equity, Member-owned golf and Country Club that accepts non-resident Members” (Our Club). Under Bylaw 8.4 as amended in December 2023, each non-resident club or marina member pays 25% of the master assessment, plus 25% of any special assessment, through the club or marina (master association document compilation). The club’s 2023 schedule showed that fee as $765 a year; at the 2025 assessment rate the arithmetic is 25% of $4,130, or $1,032.50.
The club caps golf membership at 350 and lets members book tee times up to 7 days ahead (Our Club). Its membership types page lists a WOW (“Waiting on Windstar”) category with “limited golf during the high season of November through April and unlimited golf during the off-season of May through October until accepted as a Golf Member.” The club does not publish how long that wait runs, so the membership office is the place to ask.
Tom Fazio designed the course, and the club’s own history dates the design to 1983 (Our Club; Windstar Club golf page). Per the club’s scorecard, it is 18 holes at par 72, playing 6,701 yards from the Black tees with a rating of 72.6 and a slope of 135, and it offers eight sets of tees down to the 4,595-yard Bronze tees. The course is private to Windstar Club members.
Every Windstar home pays the master assessment, which was $4,130 per home for 2025: $3,080 operating (including $780 for bulk Hotwire internet and TV), $800 replacement reserve and $250 hurricane reserve, billed quarterly at $1,032.50 (master association, 2025 annual meeting outline, March 31, 2025). On top of that sits a village fee that varies by neighborhood; the only one published is Compass Point South’s 2021 figure of $1,968.00 a quarter, which includes Compass Point’s share of the master assessment (Compass Point South Q and A, 2021). The 2026 master figure sits in the owner-only financials and on the estoppel certificate, and every other village fee is set by that association’s budget and stated on its estoppel certificate.
The master assessment pays for the gatehouse and the four master gates, master roads, lakes and mangroves, the Windstar dock, the Keewaydin Island beach property and its shuttle, the bulk Hotwire internet and TV service, and the replacement and hurricane reserves (master association, 2025 annual meeting outline; master document compilation). In 2024 the association reported about $1,486k of income against $1,459k of expense, with the gatehouse at about $338k and Keewaydin operations at about $233k. Village costs such as building insurance, condominium reserves and neighborhood pools are paid separately through each village association.
Bulk Hotwire service is paid through the master assessment, not given free: $195 a quarter ($780 a year) inside the 2025 operating line, under a 10-year agreement that started March 1, 2025 (master association communications page; 2025 annual meeting outline). The Hotwire rate sheet for Windstar (October 24, 2024) lists 500/500 Mbps internet, two TV boxes and the 199-channel Digital Favorites lineup.
No. Windstar has no Community Development District, so there is no CDD bond or operations assessment on the tax bill. The county CDD layer returns no district over Windstar, and the DOR 2025 non-ad valorem roll shows only one county charge on many Windstar parcels, $261.91 under levy code 19013.
Windstar sits in three tax-authority codes. For tax year 2025, code 0063 (most of Windstar) totals 12.6162 mills, code 0111 (Regatta Landing, which adds the 1.0000-mill Haldeman Creek MSTU) totals 13.6162 mills, and code 0004 (Admirals Watch and the Island at Southpointe, inside the City of Naples) totals 9.0514 mills (2025 Collier Taxing Authority Code Descriptions). At $1,000,000 of taxable value, the arithmetic is $12,616.20, $13,616.20 and $9,051.40 respectively. Those are illustrations, not bills: they come before non-ad valorem charges, and a homestead exemption lowers taxable value.
Yes. Windstar has four master gates, Main, Lighthouse, Gulfstar and Regatta, all funded through the master budget (2025 annual meeting outline). Under the 2018 master rules, owners, club members and registered tenants use transponders, guests and vendors are admitted when the owner registers them, and the main gate stands open on weekdays from 8 a.m. to 6 p.m. to keep traffic moving. Visitor passes run through the TekControl system listed on the master association documents page.
Yes. Southpointe Marina sits on Naples Bay at the south end of Windstar; the club and the 1988 Southpointe Yacht Club PUD describe 72 slips, the club says it takes yachts up to 70 feet (Bay Life), and the 2026 county roll carries 73 slip parcels. The marina is run by its own entity, Southpointe at Windstar Marina Association, Inc. (Sunbiz N97000006209), not by the club, and the state lists “Southpointe Marina at Windstar” as an FDEP Clean Marina. Regatta Landing has its own dock-slip association on Haldeman Creek, and Admirals Watch and the Island at Southpointe have private slips.
Not from the bay docks. NOAA’s Coast Pilot 5, chapter 4 places the US 41 bridge, “a 32-foot fixed span with a clearance of 10 feet,” at “the head of the harbor,” north of Windstar; boats from Southpointe Marina and the master dock run south to Gordon Pass without passing under it. The route from Regatta Landing’s docks on Haldeman Creek has not been verified for crossing structures or depth, so a Regatta slip buyer should confirm the creek route for their boat.
Yes, within limits. Article 7.1 of the master declaration, as amended in 2020 (Official Records Book 5764, Page 966), requires leases of not less than 30 days or one calendar month and not more than one year, with no more than three leases per calendar year, and the owner must give the association 20 days’ notice with a copy of the lease and the $145 application (master document compilation; master lease application). Villages can be stricter: Regatta Landing allows no more than two leases in any 12 months (Regatta Landing declaration), and Compass Point South requires board approval (Compass Point South Q and A, 2021). Elsewhere, each village’s Declaration and Rules govern.
No. The recorded master leasing article bars any lease shorter than 30 days or one calendar month, bars transient tenants, room rentals, subleasing and rent-sharing, and treats any paid stay of any length, or any unpaid stay of more than 7 days without the owner, as a lease (master document compilation). Weekly and nightly vacation rentals therefore do not fit Windstar’s rules.
The 2018 master rules require pets to be leashed with waste picked up, keep dogs off the golf course and cart paths, bar pets from the Keewaydin shuttle at any time, and bar them from the island property from October 15 to July 15. Villages add their own limits: Compass Point South allows owners one dog or one cat of 25 pounds or less and no pets for tenants (Compass Point South rules), and Regatta Landing allows two cats or dogs, each under 60 pounds (Regatta Landing rules, 2025). For other villages, that village’s Declaration and Rules govern.
Yes. The master association owns about 5 acres on Keewaydin Island, a barrier island south of Naples (county parcels of 2.68 and 2.74 acres), and reaches it with its own shuttle, the Keewaydin Queen III, on a trip of about 40 minutes (master association, Keewaydin Beach and Shuttle; 2025 annual meeting outline). Because the master association owns and funds it, residents use it whether or not they join the club; non-resident club and marina members gain access through the 25% Recreational Association fee.
The master association’s committee moved the shuttle season to November 1 through July 15 starting with the 2025/26 season (2025 committee reports binder). The Keewaydin page lists a morning session departing 9:30 a.m. and back by 1:00 p.m. and a later session departing 11:30 a.m. and back by 3:30 p.m. Under the booking policy revised December 16, 2025, owners book up to 30 days ahead, non-resident club and marina members 14 days ahead, up to six per household, with a $10 charge per reserved seat for a no-show. Trips can be cancelled for wind or low tide at the captain’s discretion, so check the master association’s current calendar.
Yes, with a permit. The Keewaydin booking and slip policy (revised December 16, 2025) sets a $200 annual dock permit for boats 30 feet or less, $25 per 3-hour slip reservation and a $225 fine for unauthorized docking. The same policy says the island dock is due for replacement in 2026 with cameras and gated access.
Yes, mostly. Of 68 Windstar address points we queried on FEMA’s National Flood Hazard Layer on October 10, 2026, 58 were Zone AE (32 at a base flood elevation of 9 feet NAVD88 and 26 at 8 feet), 10 were shaded Zone X (0.2% annual chance) and none was Zone VE, on FIRM panels 12021C0581J and 12021C0582J, both effective February 8, 2024. Marina Cove is mostly shaded Zone X (seven of eight sampled points), while Yacht Harbour Cove sampled AE 8. The preliminary Collier maps issued March 20, 2025 show no zone or BFE change at the Windstar points on panel 0582. A specific home’s determination comes from its elevation certificate and the lender’s flood determination.
Every Windstar point we tested sits in Collier County Hurricane Evacuation Zone A (county evacuation zone layer, queried October 10, 2026). County staff also placed the Fisherman’s Village tract, now Regatta Landing, inside the Coastal High Hazard Area in 2006 (BCC agenda, October 10, 2006), and the county’s CHHA boundary line runs east of Windstar.
Naples Bay rose sharply in Ian on September 28, 2022, but no surveyed high water mark exists inside Windstar’s gates, so no one can state a water depth inside the community from the public record. The nearest record, the USGS sensor on the Gordon River Bridge in Naples Bay about 3.4 km north, measured 7.1 feet NAVD88, and the NHC report on Ian states, “Maximum inundation of 6 to 9 ft AGL occurred in Naples.” In the census block group that contains Windstar and older neighboring streets, OpenFEMA NFIP claims show 164 Ian claims, 141 paid, about $8.77 million net; for buildings built 1980 or later, a proxy for Windstar-era construction, 89 claims and about $1.70 million.
For NFIP policies in force June 2025 to July 2026 in the census block group that contains Windstar, the median premium was $1,562 for non-condominium buildings (median policy cost $1,973, median building coverage $250,000), $842 for condominium unit owners (cost $1,159, coverage $160,000) and $4,975 for association master policies (cost $6,403, median coverage $1,000,000), per OpenFEMA NFIP policies. Every policy row carries Community Rating System class 6, which FEMA’s CRS schedule ties to a 20% discount in the special flood hazard area and 10% outside it. A specific home’s premium depends on its elevation certificate and rating, so get a quote on the address before you commit.
The county milestone inspection layer lists Windward Cay buildings 4450, 4600 and 4650 Yacht Harbor Drive and Compass Point South’s four buildings as “Milestone Completed, Cycle Completed,” with the next inspection in 2033. Compass Point South has posted its Structural Integrity Reserve Study dated May 29, 2024. Regatta Landing is capped at two stories by its 2013 annexation covenant, Admirals Watch falls under the City of Naples building department and its status is not published, and the Island at Southpointe is ten single-family homes, not a condominium. Ask each condominium association for its SIRS and milestone reports and check the DBPR SIRS reporting page.
Every Windstar address tested in the district’s address lookup for 2026-27, including the City of Naples villages, is zoned to Avalon Elementary, Gulfview Middle and Naples High. The state graded Avalon B (57% of points), Gulfview Middle A (75%) and Naples High A (67%) in its 2025-26 school grades (as of September 1, 2026). Confirm any specific address with the district’s attendance boundaries before you rely on it.
Measured from the Windstar Boulevard entrance on Bayshore Drive with OSRM free-flow routing on October 10, 2026, Fifth Avenue South is 3.1 miles and about 7 minutes, Third Street South 3.6 miles and 9 minutes, the Naples Pier 4.4 miles and 10 minutes, and Lowdermilk Park 5.3 miles and 12 minutes, without traffic. Homes at the Island at Southpointe end add about 3 to 4 minutes to every trip, and season traffic adds more.
From the Windstar entrance, Southwest Florida International Airport (RSW) is 36.5 miles and about 51 minutes without traffic, I-75 Exit 101 is 9.4 miles and 16 minutes, Exit 105 is 10.9 miles and 19 minutes, and Naples Airport is 4.4 miles and 11 minutes (OSRM free-flow routing, October 10, 2026).
The NCH Baker Hospital emergency department at 350 7th Street North, open 24 hours, is about 4.0 miles and 10 minutes from the Windstar entrance, and Physicians Regional Collier Boulevard (130 beds, 24-hour ER) is 6.1 miles and 14 minutes (OSRM free-flow, October 10, 2026). For smaller problems, Physicians Regional East Naples urgent care at 4525 Thomasson Drive takes walk-ins from 7 a.m. to 7 p.m. daily, 1.8 miles and 5 minutes away, and Collier County EMS Medic 22 is stationed at 4375 Bayshore Drive, about 0.3 miles from the entrance (county EMS stations layer).
Windstar has tennis and bocce through the club, but no club pickleball. The Windstar Club lists six Har-Tru tennis courts, two of them lit (club tennis page), and three lighted Har-Tru bocce courts (club bocce page). The club lists no pickleball courts; the public Naples Pickleball Center at East Naples Community Park is about 1.13 miles straight-line from the clubhouse (county parks layer). Spinnaker Pointe keeps two lighted tennis courts of its own for its residents (Spinnaker Pointe page).
No. The club’s published amenity list has no pool or spa (Windstar Club home; Lifestyle); pools are run by the neighborhood associations. Neighborhood pools are listed at Admirals Watch, Marina Cove, Spinnaker Pointe, Windward Cay, Morningstar, Regatta Landing, Somerset at Windstar, Yacht Harbour Cove and Compass Point South, while Clipper Cove, Harrington Sound, Ketch Cay, Spyglass Pointe and Northstar homes have private pools, per the master association’s neighborhood pages and the village association sites.
The club lists four dining venues at the clubhouse: 1700 Grille, the Bayview Dining Room, the Sunset Lounge and Veranda, and The Wine Room (Windstar Club dining). The club notes country-club attire upstairs and casual dress downstairs.
Members approved a $13 million clubhouse renovation and expansion, reported by Club + Resort Business on October 29, 2021, and the county records a clubhouse expansion site plan amendment, PL20210001972, on its CityView projects layer. The club describes the “enhancement of our Clubhouse” on its Our Club page. No completion date has been published in a primary record.
Windstar mixes condominiums, attached villas, coach homes, single-family courtyard and pool homes, and bayfront estates. Grouped by McGreevy and Comisar from the 52 Southwest Florida MLS sales of October 13, 2025 to October 13, 2026, condominiums had a $1,096,250 median across 36 sales, while detached single-family homes (8 sales, $1,375,000 to $6,750,000) and attached villas (8 sales, $660,000 to $1,300,000) were too few for a 12-month median; over 24 months their medians were $1,600,000 across 22 sales and $1,100,000 across 13 sales. By village, the lower end ran from Compass Point South (2 sales, $430,000 and $508,000) and Spinnaker Pointe (5 sales, $525,000 to $905,000) to Marina Cove (6 sales, $507,500 to $745,000); the top included Admirals Watch (3 sales, $2,375,000 to $3,625,000) and one Island at Southpointe sale, at $6,750,000. The full village table sits in the Market Snapshot.
Regatta Landing is the newest: 64 coach homes on Haldeman Creek built from 2016 to 2021, per the year-built field on the Florida Statewide Cadastral layer and the Regatta Landing association site. Its condominium declaration names Standard Pacific of Florida as developer.
No new homes. Both of Windstar’s PUDs are listed by the county as built out on its PUD layer; the last new homes were Regatta Landing’s in 2021. The only active construction inside the gates is the club’s: the club says a new fitness center is due in 2026 and runs a temporary center meanwhile, and the county’s CityView layer shows the fitness center site plan amendment, PL20240013453, under site inspection.
Change near Windstar comes from the Bayshore CRA corridor. The county posted ITN 26-8663 for outparcels of its 17-acre Cultural Arts Village site across Bayshore Drive, about 0.16 miles from the gate, on July 15, 2026 (Bayshore CRA, 17-Acre ITN), and the Bayshore Boardwalk to Sugden Regional Park opened February 26, 2026. Within a mile, the county approved Windward Landing (up to 90 single-family homes, about 0.64 miles away, a separate project and not Windstar’s Windward Cay), The Halcyon (66 condominium units and a 120-slip marina, about 0.95 miles away) and up to 507 multifamily units in the Mini-Triangle MPUD, about 0.79 miles away. The pipeline section above has the sources.
Not on the master property. The 2018 master rules bar boats, trailers, RVs and commercial vehicles from being parked overnight on master roads or common areas, the master association runs no storage yard, and electric vehicles may not be charged on master common areas. What you may keep on your own lot or in your own garage follows your village’s Declaration and Rules.
Windstar is gated, golf-centered and run by a master association over 16 villages, with a $4,130 master assessment in 2025 and a private Keewaydin beach by shuttle; Royal Harbor is an ungated City of Naples canal neighborhood of single-family homes with no mandatory HOA, according to our Royal Harbor page. Both sit south of the fixed US 41 bridge, both are mapped mostly Zone AE in Evacuation Zone A, and both feed Gulfview Middle and Naples High, so the choice usually turns on governance, product and price; the “Windstar vs Royal Harbor” section above has the full decision table, including the two communities’ different 12-month MLS windows.
Windstar on Naples Bay sellers ask about price, timing, closing costs, association paperwork, boat slips and condominium law before they list. The answers below use only the Southwest Florida MLS figures for the 12 months to October 13, 2026, the master association’s published fees and the recorded documents, with each source linked at the point of use.
If you are ready to talk through a sale now, start with how we sell homes in Naples, or Call Jesse direct at (239) 898-6072. The six seller questions answered in the seller section above (top-selling villages, club transfers, estoppel certificates, the owner’s title policy, boat slips and condominium reports) are not repeated here.
McGreevy and Comisar are the #5 real estate team in Florida in the 2026 RealTrends rankings, Top 1% Real Estate Agents Nationally Since 2008, and the #1 team in Southwest Florida since 2012, with over $900 million in personal sales; our brokerage’s Naples record is the sales-sides sentence in the authority block at the top of this page. For a Windstar listing, what matters is pricing by village, explaining the master and village fee layers, and presenting flood and condominium documents before a buyer asks; request a free home valuation or Call Jesse direct at (239) 898-6072.
Your home’s value starts with your own village’s recent sales, not the community-wide figure. In the Southwest Florida MLS for October 13, 2025 to October 13, 2026, no village reached 10 sales, so village figures are ranges: Regatta Landing’s 9 sales ran from $1,090,500 to $1,849,000 and Marina Cove’s 6 from $507,500 to $745,000, with 24-month medians of $1,310,000 (16 sales) and $646,000 (12 sales). The county’s just value on your tax notice is an appraisal figure for tax purposes, not a sale price, so do not price from it. For a figure built on your village, your floor plan, your elevation certificate and your view, get a free home valuation or Call Jesse direct at (239) 898-6072.
We tracked 52 closed sales in Windstar on Naples Bay in the 12 months to October 13, 2026: $70,378,500 in volume, a $1,200,000 median and a range of $350,000 to $6,750,000 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026). With 52 sales the median is the mean of the middle pair, which were both $1,200,000. The average was $1,353,433 ($70,378,500 divided by 52), pulled up by a handful of estate and bayfront sales, so the median is the better guide.
Regatta Landing recorded 9 sales in the 12 months to October 13, 2026, from $1,090,500 to $1,849,000, too few for a 12-month median; over 24 months its 16 sales had a $1,310,000 median (Southwest Florida MLS). Regatta Landing is Windstar’s newest village, 64 coach homes built 2016 to 2021, and it was the most active village in the window.
Marina Cove recorded 6 sales in the 12 months to October 13, 2026, from $507,500 to $745,000 (24 months: 12 sales, median $646,000) (Southwest Florida MLS). Marina Cove is 72 coach-style condominiums with a community center by the Southpointe marina basin (Marina Cove page), and most of it maps as shaded Zone X on the 2024 flood maps, a point worth putting in front of buyers.
Somerset at Windstar recorded 5 sales in the 12 months to October 13, 2026, from $660,000 to $1,300,000 (24 months: 10 sales, median $1,095,000) (Southwest Florida MLS). Somerset is 50 one- and two-story duplex villas on Paget Circle under a homeowners association (Somerset at Windstar site).
Spinnaker Pointe recorded 5 sales in the 12 months to October 13, 2026, from $525,000 to $905,000 (24 months: 11 sales, median $630,000) (Southwest Florida MLS). The $905,000 sale is a record entered into the MLS after closing; it counts in the count and the range. Spinnaker Pointe is 88 carriage homes on Windjammer Circle with its own clubhouse, pool and two lighted tennis courts (Spinnaker Pointe page).
Admirals Watch recorded 3 sales in the 12 months to October 13, 2026, at $2,375,000, $2,935,000 and $3,625,000 (Southwest Florida MLS). Admirals Watch is 16 bayfront condominiums with eight boat slips (Admirals Watch page), inside the City of Naples, which gives it the lowest of Windstar’s three millage rates (9.0514 mills for tax year 2025).
Yacht Harbour Cove recorded 5 sales in the 12 months to October 13, 2026, from $1,200,000 to $2,250,000 (36 months: 11 sales, median $1,700,000) (Southwest Florida MLS). Its 28 coach homes sit on the Southpointe marina basin (Yacht Harbour Cove page).
Compass Point South recorded 2 sales in the 12 months to October 13, 2026, $430,000 and $508,000 (36 months: 14 sales, median $503,500). Northstar recorded two sales, $1,325,000 and $1,375,000, too thin to read as a market rate (Southwest Florida MLS). The two share Haldeman Creek Drive but not much else: Compass Point South is 72 condominiums in four three-story buildings, and Northstar is 16 villas with private pools (Compass Point South site; Northstar page).
Harrington Sound recorded one sale in the 12 months to October 13, 2026, at $2,075,000, too thin to read as a market rate (Southwest Florida MLS). With one sale, pricing a Harrington Sound estate leans on the home itself, the lot, its elevation against the 2024 base flood elevation of 8 feet sampled on Lighthouse Lane, and the wider top of the Windstar market, where 6 of the 52 sales closed at $2,000,000 or more.
Windward Cay recorded 4 sales in the 12 months to October 13, 2026, from $350,000 to $1,075,000. Leeward Cay recorded 3 sales, $800,000, $1,137,000 and $1,270,000 (Southwest Florida MLS). Both sit on Yacht Harbor Drive: Windward Cay is the 48-unit condominium at 4400 to 4800, and Leeward Cay the 16 attached villas at odd addresses between 4401 and 4773.
The 48 Windstar closings that carry a days-on-market figure in the 12 months to October 13, 2026 had a median of 59 days on market, against 34 in the prior 12 months (Southwest Florida MLS; the Sold Data Entry record and three closings recorded at zero days are left out). Time to contract varies by village and price band, and a well-documented listing, with the estoppel figures, the elevation certificate and any condominium inspection reports ready, avoids the delays that come from a buyer waiting on paperwork.
Windstar’s median sold price per square foot for the 12 months to October 13, 2026 was $493 (Southwest Florida MLS). Price per square foot swings widely between a 1980s condominium and a bayfront estate, so compare against your own village’s sales rather than the community figure.
Active Windstar listings in the Southwest Florida MLS at the October 13, 2026 pull: 15, plus 5 pending. For context, the market closed 52 sales in the 12 months to October 13, 2026.
The busiest months in the 12 months to October 13, 2026 were June 2026 (10 closings), April 2026 (8) and December 2025 (7), and July and August 2026 had 2 closings each; the export records no closing after August 25, 2026, so September and the first days of October show none (Southwest Florida MLS); the Market Snapshot has the month-by-month table. That is one year of data, so read it as this window’s pattern, not a rule.
The main seller costs are the listing commission, which is negotiable, and Florida’s documentary stamp tax on the deed, which the seller pays by custom. In Collier County the buyer customarily pays the owner’s title policy, and the contract controls, so it is not a seller cost here. Add any balance owed to the master and village associations, which the estoppel certificates state, plus the estoppel fees themselves, which are set by Florida statute and by each association. A Windstar seller also pays the prorated property tax and, if the home has a Regatta Landing dock certificate or a marina slip, whatever transfer the slip documents require.
In Collier County the buyer customarily pays the owner’s title policy and chooses the closing agent; the purchase contract controls, and it can say otherwise. Custom differs in some other Florida counties, so confirm the split in the contract if your buyer is relocating.
At the master level, the board proposed a resale capital contribution in 2023 (October 2023 newsletter; President’s remarks, October 2023); the amendment certificate recorded in January 2024 (Official Records Book 6322, Page 2115) does not contain one (master document compilation). Buyers confirm on the master estoppel certificate. At the village level, the Regatta Landing declaration defines “Capital Contribution Assessments,” and amounts for Regatta and the other villages are not published; each association’s estoppel certificate states what applies.
They will be paid at closing, one way or another. Under Bylaw 8.3, master assessments are due on the first day of each quarter and delinquent if unpaid by the 11th day of the quarter’s first month, and the master association holds lien rights for unpaid assessments (master document compilation). The estoppel certificate states the balance as of closing, and the title agent pays it from your proceeds, so bring the account current early to keep the closing statement clean.
The master association’s recorded documents read for this page do not publish a purchase-approval step for sales; any approval right for a sale sits in your village’s declaration, so check your own neighborhood or condominium documents (master document compilation). Leases are different: the master association requires 20 days’ notice, a copy of the lease and a $145 application (master lease application), and some villages, such as Compass Point South, require board approval of tenants.
Article 7.1 of the master declaration requires owners to give purchasers copies of the Declaration, Bylaws and Rules before closing (master document compilation). Florida law adds the statutory disclosures: condominium sellers deliver the documents listed in section 718.503 of the Florida Statutes, and sellers in a homeowners-association village give the disclosure summary in section 720.401. Add your village’s rules and budget, the estoppel certificates, your elevation certificate, and for a condominium the association’s milestone and SIRS reports where they apply.
For luxury Windstar sellers, McGreevy and Comisar bring premium marketing, cinematic video, drone, professional photography, a qualified-buyer database, discretion and off-market capability when needed. A Windstar listing also needs the facts buyers test: the village’s own recent sales, the $4,130 master assessment for 2025 and the village fee above it, the flood zone and elevation certificate, and whether the home’s buyer pool is likely to want a Windstar Club membership. To start, request a free home valuation or Call Jesse direct at (239) 898-6072.
Yes. McGreevy and Comisar offer discretion and off-market capability when needed, which suits owners who would rather not advertise a sale inside a gated community or who want to test a price quietly first. Confidential conversations welcome: Call Jesse direct at (239) 898-6072, text or call.
The club’s bylaws govern, and the club’s 2023 fee pages state that the “Windstar Club’s Bylaws does not permit any refund or cessation of fees during the membership year” (2023 club fee pages). How a membership transfers or is resigned when you sell sits in the club’s membership documents, which the club has not published, so ask the club’s membership office before you set a closing date.
Southpointe Marina slips are separate parcels on the county roll; the 2026 preliminary roll carries 73 slip parcels (Florida DOR 2026 preliminary roll). Who may buy a slip and on what terms is set by the marina association’s documents (Southpointe at Windstar Marina Association, Inc., Sunbiz), so read them, and the estoppel the marina association issues, before you split the sale.
Regatta Landing slips are held by Dock Slip Certificate through Regatta Landing Dock Slip Association, Inc. (Sunbiz N17000010798), and they move by the Dock Slip Certificate Assignment form recorded as Exhibit P at Official Records Book 5448, Page 1149. The slips sit outside the condominium and its assessments (Regatta Landing declaration). Under the 2013 annexation terms, slips are offered first to Regatta owners, then to other Windstar owners, and to outsiders only after a year, and outside slip owners pay 25% of the master assessment (master document compilation).
Buyers will see it, so explain it. The master assessment went from $3,250 in 2024 to $4,130 in 2025, an increase of $880 or 27.1%, and $780 of that is the new bulk Hotwire internet and TV line (master association, 2025 annual meeting outline). Put that way, the increase outside the Hotwire line was $100 a year.
The master association’s March 2025 deck projects a reserve outlay of about $1.70 million in 2030 for docks, channel, road and marina entrance dredging, funded from the reserve plan as projected (2025 annual meeting outline); no special assessment is announced in the published sources. A separate master dock dredge is estimated at about $400,000, with permits expected to take 2 to 3 years (2025 committee reports binder). Village and condominium associations set their own budgets, so a special assessment, if any, shows on your association’s estoppel certificate.
Yes, a small one. The master association reported a term loan payable of $287,471 at December 31, 2024, with principal and interest of about $72,000 a year, and the March 2025 deck noted the board may pay it off in 2025 (2025 annual meeting outline). The same deck showed replacement reserve cash of $743,918 and operating cash of $246,693 at that date.
The master association’s hurricane and storm reserve held $632,382 at December 31, 2024, after about $127,000 of 2024 hurricane-fund spending on Debby, Helene, Milton and residual Ian work (2025 annual meeting outline). The 2025 assessment put $250 per home into that reserve, with collections scheduled for 2025 to 2027. Village and condominium associations carry their own storm costs in their own budgets.
Only if it has three habitable stories or more: Florida requires a Structural Integrity Reserve Study for those condominium buildings at least every 10 years, with existing associations due by December 31, 2025 and never later than December 31, 2026 (s. 718.112, Florida Statutes), and chapter 2025-175 lets an association that completed a milestone inspection delay a SIRS up to two consecutive budget years. In Windstar, the county milestone layer lists Windward Cay buildings 4450, 4600 and 4650 Yacht Harbor Drive and Compass Point South’s four buildings as “Milestone Completed, Cycle Completed,” next inspection 2033. Ask your association which applies to your building.
Check the DBPR SIRS reporting page, where associations report completed studies, and ask your association for its own copy. Compass Point South has posted its Structural Integrity Reserve Study dated May 29, 2024 publicly, showing minimum 2025 reserve funding of $118,650. Buyers have a right to these documents, so having them in hand before you list shortens the contract period.
Most likely Zone AE with a base flood elevation of 8 or 9 feet NAVD88: 58 of 68 Windstar address points we queried on FEMA’s National Flood Hazard Layer on October 10, 2026 were AE, on panels effective February 8, 2024. Most of Marina Cove (seven of eight sampled points) is shaded Zone X, Northstar and Morningstar each had one shaded X point, and no sampled home fell in Zone VE. The lender’s flood determination and your elevation certificate settle the answer for your house.
No law requires one to list, but lenders and flood insurers use it, and a buyer will ask for it. Collier County publishes many certificates on its elevation certificate layer; the Windstar certificates sampled for this page show lowest floors from 8.0 to 9.5 feet NAVD88 against base flood elevations of 8 or 9 feet. If yours is not on file, a surveyor can prepare one before you list.
Florida sellers must disclose known facts that materially affect a home’s value and are not readily observable to the buyer, and storm damage and its repair history fall squarely in that category. No Windstar-specific damage record is public, so the disclosure comes from what you and your association know: repairs, insurance claims and any permits. If a building was substantially damaged, federal floodplain rules treat repairs costing 50% or more of market value as substantial improvement (44 CFR 59.1), which a buyer’s lender may ask about.
For-sale signs follow your neighborhood association’s rules and may never go on master association property, and association-approved open house signs are signed out at the guardhouse, under the 2018 master rules. Because Windstar is gated, visitors are admitted when an owner registers them, so plan how open house guests will be cleared at the gate.
That depends on your plans. Leasing in Windstar is limited by the master declaration to terms of 30 days or one calendar month up to one year and no more than three leases a year, with stricter village rules such as Regatta Landing’s two leases in any 12 months (master document compilation), while the sales market recorded 52 closings and a $1,200,000 median in the 12 months to October 13, 2026 (Southwest Florida MLS). To weigh both with your village’s numbers, get a free home valuation or Call Jesse direct at (239) 898-6072.
Jesse McGreevy and Marc Comisar are the Windstar on Naples Bay real estate experts to call, sellers first and buyers too: Jesse has been in Southwest Florida real estate since 2004, McGreevy and Comisar have been Top 1% Real Estate Agents Nationally Since 2008, and McGreevy and Comisar are the #5 real estate team in Florida in the 2026 RealTrends rankings.
Anyone searching “Windstar Naples” is usually weighing one of two decisions: what a home in a particular village is worth today, or which of the 16 villages fits a buyer’s budget, boat and lifestyle. Those answers sit in the village sales, the master and village fee layers, the flood maps and the club’s terms covered on this page, and we walk sellers and buyers through each of them before a price is set or an offer is written.
McGreevy and Comisar lead Domain Realty Group, a team that has sold over $2.5 billion in real estate; learn more about the team at Domain Realty Group. Jesse and Marc alone have over $900 million in sales, and the team has been the #1 team in Southwest Florida since 2012, launched in 2008 and recognized with Gulfshore Life Magazine’s 5 Star Award for Customer Satisfaction for 21 straight years. Jesse has lived in Estero since 2003, and our Naples office is at 9180 Galleria Ct #200, Naples, FL 34109.
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).
Selling your Windstar on Naples Bay home? Get a free home valuation built on your village’s own sales, or Call Jesse direct at (239) 898-6072. Confidential conversations welcome.
Buying in Windstar on Naples Bay? Call Marc at (239) 287-5873 and see how McGreevy and Comisar represent buyers in Naples, from choosing a village to reading its estoppel and flood documents before you commit.
Every fact on this Windstar on Naples Bay page comes from a primary record: the recorded association documents and association websites, the Windstar Club’s own pages, Florida and Collier County government records, federal flood and weather data, school and hospital sites, and county legal notices. Each source below was retrieved in October 2026 unless its title gives another date.
Market figures come from the Southwest Florida MLS (Matrix), closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026; the MLS is cited in words because its records sit behind a member login. Royal Harbor comparison figures come from our live Royal Harbor page, read October 10, 2026, which carries its own primary sources.
633 people live in Windstar on Naples Bay, where the median age is 68 and the average individual income is $62,394. Data provided by the U.S. Census Bureau.
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There's plenty to do around Windstar on Naples Bay, including shopping, dining, nightlife, parks, and more. Data provided by Walk Score and Yelp.
Explore popular things to do in the area, including Windstar on Naples Bay.
Windstar on Naples Bay has 360 households, with an average household size of 2. Data provided by the U.S. Census Bureau. Here’s what the people living in Windstar on Naples Bay do for work — and how long it takes them to get there. Data provided by the U.S. Census Bureau. 633 people call Windstar on Naples Bay home. The population density is 1,838 and the largest age group is Data provided by the U.S. Census Bureau.
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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.
