Updated October 2026
Sell your Windstar on Naples Bay home with McGreevy and Comisar, Top 1% Real Estate Agents Nationally Since 2008. Village-by-village pricing from 52 MLS closings, both estoppel certificates ordered early. Call (239) 898-6072.
Updated October 2026 · Jesse McGreevy and Marc Comisar, Domain Realty
Selling a home in Windstar on Naples Bay means pricing one of 16 villages, not one community, and Jesse McGreevy and Marc Comisar build every Windstar listing from the village’s own closed sales, its association layers, its flood record and the buyer pool that home actually draws. Windstar on Naples Bay is a gated golf and boating community in Naples, Florida, ZIP 34112: 618 homes and condominiums in 16 villages on the east shore of Naples Bay off Bayshore Drive, per the Florida Department of Revenue 2026 preliminary tax roll (read October 2026). It is the community off Bayshore Drive, not the cruise line of the same name. Our full guide to the place, from the 1981 PUD to the Keewaydin Island beach, is the Windstar on Naples Bay community guide, and this seller page sits beside it. Everything below answers one owner’s question: how to sell a Regatta Landing coach home, a Marina Cove condominium, a Somerset villa or a bayfront estate for the most money, with the fewest surprises, on a date you choose.
If you want a number first, request a written opinion of value on our Windstar on Naples Bay home valuation page, or call Jesse direct at (239) 898-6072. If you are also buying, our Windstar on Naples Bay buyer page is written for that side of the move.
Windstar on Naples Bay sellers face sixteen separate markets behind one gate: the 12 months to October 13, 2026 produced 52 closed sales from $350,000 to $6,750,000, and no village reached 10 sales in that window (Southwest Florida MLS). McGreevy and Comisar, the #1 Team in Southwest Florida since 2012, price each village from its own closings and run the association paperwork for you.
Jesse McGreevy has worked in Southwest Florida real estate since 2004, and he and Marc Comisar have been Top 1% Real Estate Agents Nationally Since 2008, leading the #1 Team in Southwest Florida since 2012. If you are interviewing listing agents before you choose, our guide to the best real estate agents in Naples compares the teams on the public record. For a Windstar owner the test is simple: ask every agent to show you the closed sales in your own village, explain how the master assessment and your village assessment read on an estoppel certificate, and say how they will answer the club question a buyer asks at the first showing.
These are career figures across Lee and Collier counties, and we label them that way. As the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate, and Jesse and Marc alone have over $900 million in sales inside that number.
You get Jesse and Marc, not a coordinator reading from a template. Jesse McGreevy runs pricing, data, marketing and the association paperwork, which in Windstar means the master association, your village association or condominium and, on some sales, a marina or dock association, all issuing documents on one closing. Marc Comisar runs the field: gate registrations for showings, buyer-agent conversations, inspections, contractors and walkthroughs for owners who are out of state for the summer. Reach Jesse at (239) 898-6072 or Marc at (239) 287-5873, and read how the partnership works on our about McGreevy and Comisar page.
A Windstar buyer is buying more than a floor plan. They are buying a village (with its own association, budget and rules), a share of the master association (the gate, the roads, the lakes, the Windstar dock and the Keewaydin Island beach), a flood profile on the February 8, 2024 FEMA maps, one of three property tax rates, and the option, never the obligation, to join the Windstar Club. Some homes also carry a boat slip that is governed separately from the house. We price and prepare each of those layers before the first showing, because a buyer’s lender, insurer and attorney will read every one of them.
Selling in Windstar on Naples Bay differs from a typical Naples sale in six ways: 16 villages trade as separate markets, every sale carries at least two association layers, the club is optional and separate, two villages sit in the City of Naples, boat slips travel under their own documents, and flood zones vary by village.
Data updated: October 2026
Windstar’s 618 homes split into 9 condominium villages with 428 units and 7 homeowners-association villages with 190 homes, per the DBPR condominium extract and the Florida DOR 2026 preliminary roll (both read October 2026). They were built from 1984, when Windward Cay delivered Windstar’s first homes, to 2021, when Regatta Landing finished its 64 coach homes. A 1,414 square foot Compass Point South condominium (the village’s median living area on the 2026 roll) and a 5,413 square foot Island at Southpointe estate (that village’s median) share a gate and a master assessment and almost nothing a pricing model can use. Our pricing starts by deciding which village market your home is actually in.
Every Windstar home belongs to Windstar on Naples Bay Master Association, Inc., a Chapter 720 homeowners association, and Article 5 of its recorded master declaration assigns each home one equal assessment unit (master association recorded document compilation, posted January 24, 2024). Below it, each village has its own condominium or homeowners association with its own budget. That means at least two estoppel certificates on a closing, two sets of rules a buyer reads, and two budgets the buyer’s lender may ask about. Jesse orders both early, so neither surprises the closing date.
Windstar is not bundled. The Windstar Club states that “Residents within the gates are not required to be Members,” and Section 1.5 of the master declaration says no owner gains club rights “simply by virtue of ownership or occupancy of a Unit.” For a seller this cuts two ways: your buyer pool includes buyers who never want a club, and buyers who want golf will ask how and when they can join. We answer that question in the listing, not in the third week of a contract.
Most of Windstar is unincorporated Collier County, but Admirals Watch and the Island at Southpointe lie inside the City of Naples, per the county’s City Limits layer (queried October 2026). That changes the tax rate a buyer inherits (9.0514 mills against 12.6162 for most of Windstar in tax year 2025, per the 2025 Collier Taxing Authority Code Descriptions) and which building department holds the permit history. We read the right record for your village before we describe your home to a buyer.
Boat slips in Windstar are governed separately from the homes. Southpointe Marina slips sit under Southpointe at Windstar Marina Association, Inc.; Regatta Landing slips are held by Dock Slip Certificate through Regatta Landing Dock Slip Association, Inc.; and Admirals Watch’s eight slips belong to that condominium (master association Admirals Watch page). Whether a slip goes with your sale, and how it transfers, is a document question we settle before the listing goes on the market. Every owner, member or not, keeps access to the master association’s Keewaydin Island beach and its shuttle, which is a selling point for every village.
Of 68 Windstar address points queried against FEMA’s National Flood Hazard Layer on October 10, 2026, 58 were Zone AE with a base flood elevation of 8 or 9 feet NAVD88 and 10 were shaded Zone X, most of them in Marina Cove; none was Zone VE. Panels 12021C0581J and 12021C0582J have been effective since February 8, 2024. A buyer’s lender reads that map, so your village’s zone and your home’s elevation certificate are pricing facts, covered in the pricing and local expertise sections below.
Most Windstar condominium buildings are one or two stories and fall outside Florida’s structural integrity reserve study and milestone inspection rules. The exceptions in the public record are Windward Cay buildings 4450, 4600 and 4650 Yacht Harbor Drive and Compass Point South’s four three-story buildings, which Collier County’s milestone inspection layer lists as “Milestone Completed, Cycle Completed,” next inspection year 2033 (read October 10, 2026). A seller in those buildings who has the reports in hand before listing takes the biggest condominium objection off the table.
Windstar on Naples Bay recorded 52 closed sales and $70,378,500 in volume in the 12 months to October 13, 2026, at a $1,200,000 median (Southwest Florida MLS). These eight facts frame every pricing, marketing and paperwork decision a Windstar seller makes on the pages that follow, each with its source and date.
A Windstar on Naples Bay seller hiring McGreevy and Comisar gets Top 1% Real Estate Agents Nationally Since 2008, the #1 Team in Southwest Florida since 2012, over $900 million in personal sales, and a brokerage with a deep Naples record, applied to a Windstar market we tracked sale by sale: 54 closings and $72,179,000 in 12 months.
Data updated: October 2026 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026)
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, and he and Marc Comisar launched the team in 2008. As the leaders of Domain Realty Group our team has closed over $2.5 billion in real estate, and Jesse and Marc alone have over $900 million in sales. Those are career figures across Southwest Florida. They tell you how many negotiations, inspections and closing-table surprises the people on your listing have already handled, which matters most on a sale with a master association, a village association and sometimes a dock association in the room.
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. That is the brokerage’s Naples figure, not a count for any one community, and we label it that way.
Southwest Florida MLS, 12 months to October 13, 2026 | Closings | Median price | Volume | Range |
|---|---|---|---|---|
All of Windstar on Naples Bay | 52 | $1,200,000 | $70,378,500 | $350,000 to $6,750,000 |
Condominiums (8 villages) | 36 | $1,096,250 | $43,331,500 | $350,000 to $3,625,000 |
Attached villas (Somerset, Leeward Cay) | 8 | no median (fewer than 10 sales) | $8,692,000 | $660,000 to $1,300,000 |
Detached single-family (5 villages) | 8 | no median (fewer than 10 sales) | $18,355,000 | $1,375,000 to $6,750,000 |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026; segments grouped by McGreevy and Comisar from the MLS rows by each village’s recorded form of ownership. One of the 52, a $905,000 Spinnaker Pointe closing on February 27, 2026, is a Sold Data Entry record (a sale entered after it closed). It counts in closings, medians, ranges and 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 closings. Over 24 months, where the villa and detached groups pass 10 sales, villas had a $1,100,000 median (13 sales) and detached homes a $1,600,000 median (22 sales), against $745,000 for condominiums (67 sales).
We judge a Windstar listing on three numbers you can check: days on market against the median for your village and product (59 days across Windstar in the latest 12 months), the sale price against its final list price (a median sale-to-list of 94.7% across Windstar), and whether the home closed on the date you planned. Those are the yardsticks the rest of this page uses, and the ones we report on your own sale.
For a home priced to its own village, yes. Windstar on Naples Bay recorded 52 closings in the 12 months to October 13, 2026 at a $1,200,000 median, with sales in 15 of its 16 villages, and a built-out community means every buyer you meet is choosing among resales, not a builder’s model homes.
Data updated: October 2026 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026)
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) |
Median days on market | 59 days (average 73; the 48 closings with a days-on-market figure) |
Median sale-to-list ratio | 94.7% (average 94.5%; same 48 closings) |
Median price per square foot | $493 (all 52 closings, sold price over living area) |
Median list price | $1,249,500 (median final list price of the 52 closed sales) |
Active listings | 15 active and 5 pending at the October 13, 2026 pull |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026. The average is our arithmetic.
Every Windstar village with a sale in the window is listed below. 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 | Sales | Median or sales listed | Low | High |
|---|---|---|---|---|
Regatta Landing | 9 | no median in 12 months; 24 months: 16 sales, median $1,310,000 | $1,090,500 | $1,849,000 |
Marina Cove | 6 | no median in 12 months; 24 months: 12 sales, median $646,000 | $507,500 | $745,000 |
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 | 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 | 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 | 4 | $350,000, $665,000, $725,000 and $1,075,000 | $350,000 | $1,075,000 |
Admirals Watch | 3 | $2,375,000, $2,935,000 and $3,625,000 | $2,375,000 | $3,625,000 |
Ketch Cay | 3 | $1,375,000, $1,525,000 and $1,750,000 | $1,375,000 | $1,750,000 |
Leeward Cay | 3 | $800,000, $1,137,000 and $1,270,000 | $800,000 | $1,270,000 |
Clipper Cove | 2 | $1,480,000 and $1,625,000 | $1,480,000 | $1,625,000 |
Compass Point South | 2 | $430,000 and $508,000; 36 months: 14 sales, median $503,500 | $430,000 | $508,000 |
Northstar | 2 | $1,325,000 and $1,375,000 | $1,325,000 | $1,375,000 |
Harrington Sound | 1 | one sale, at $2,075,000 (thin) | ||
Island at Southpointe | 1 | one sale, at $6,750,000 (thin) | ||
Spyglass Pointe | 1 | one sale, at $1,775,000 (thin) | ||
Morningstar | 0 | no closed sale in the window |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026. The MLS files the Island at Southpointe’s ten estates under the name “Southpointe Yacht Club” and Northstar as “Northstar Villas.”
Condominiums were 36 of the 52 closings, about seven in ten by count and $43,331,500 of the $70,378,500 in volume, which matches Windstar’s makeup: 428 of its 618 homes are condominium units. The condominium median of $1,096,250 (an even count: the mean of $1,090,500 and $1,102,000) hides a very wide range, from the $350,000 Windward Cay sale to the $3,625,000 Admirals Watch sale, and it mixes 1990s three-story buildings with 2016 to 2021 coach homes. The villa segment is the opposite: two homeowners associations, homes of similar age, and eight sales from $660,000 to $1,300,000. Detached homes, eight sales from $1,375,000 to $6,750,000 (a $1,600,000 median over 24 months, 22 sales), sit above both. A condominium seller in Windstar is really competing in one of five or six separate markets.
Price band, 12 months to October 13, 2026 | Closings |
|---|---|
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.
The bands 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 fell between $750,000 and $999,999: the $905,000 Spinnaker Pointe record and an $800,000 Leeward Cay villa. A seller whose price lands in that gap has few direct comparables, and the first price decides which of the two buyer groups sees the listing.
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.
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, during the winter-resident season. The export records no closing after August 25, 2026. One year of data is not enough to call a seasonal price pattern, and we do not read it as one; what it does show is when Windstar buyers were writing contracts in this window.
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, so a villa or estate seller has no active competitor in the same product today. Inventory changes week to week in a community of 618 homes, so before we set your price we pull the active and pending listings in your own village and price band, because those are the homes your buyer tours the same weekend. A buyer’s appraiser reads closed sales, not asking prices, so we price from the closings and position against the listings.
The median sits at $1,200,000 because the 52 sales cluster between $1,000,000 and $1,499,999 and between $500,000 and $749,999. 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 Windstar home, neither number is the right anchor. 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). The village tables in the pricing section are the ones to use.
We price a Windstar on Naples Bay home from its own village’s closed sales, adjusted for floor plan, view (fairway, lake, bay or marina), condition, roof and openings, the home’s elevation certificate against the 2024 flood map, the village’s fees and reserves and any slip that conveys, then test the number against live listings and what a buyer’s appraiser will find.
Data updated: October 2026 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026; window rule: the 12 months to the pull, with no village median under 10 sales and the 24 or 36-month window named wherever one is used)
The villages do not share comparable sales. A Regatta Landing coach home is valued against Regatta’s own 9 sales and its newer construction; a Marina Cove condominium against Marina Cove’s 6 sales in a tight band; a Harrington Sound estate against its lot, its elevation and the top of the Windstar market, because the village had one sale. We pull the 12-month closings for your village first, then the closest product elsewhere inside the gates, and adjust for the village’s fees and flood zone before we look at anything outside Windstar.
The fairest benchmark for a Windstar home is the neighboring village with the same product, from the same pull. No village has 10 sales in 12 months, so these pairs use the 24 or 36-month median, with the window named, wherever a village reaches 10 sales, and show the sales range where it does not.
Product | Village and median | Nearest comparable village and median | Gap |
|---|---|---|---|
Entry condominium | Marina Cove, $646,000 (12 sales, 24 months) | Spinnaker Pointe, $630,000 (11 sales, 24 months) | $16,000 |
Entry condominium | Compass Point South, $503,500 (14 sales, 36 months) | Spinnaker Pointe, $647,500 (14 sales, 36 months) | $144,000 |
Attached villa | Somerset at Windstar, $1,095,000 (10 sales, 24 months) | Leeward Cay, three sales from $800,000 to $1,270,000 in 12 months | not computed (no Leeward Cay median) |
Coach home | Regatta Landing, $1,310,000 (16 sales, 24 months) | Yacht Harbour Cove, $1,700,000 (11 sales, 36 months) | $390,000 |
Detached courtyard or pool home | Ketch Cay, three sales from $1,375,000 to $1,750,000 in 12 months | Clipper Cove, two sales at $1,480,000 and $1,625,000 in 12 months | not computed (no medians) |
Bayfront condominium | Admirals Watch, three sales from $2,375,000 to $3,625,000 in 12 months | Yacht Harbour Cove, $1,700,000 (11 sales, 36 months) | not computed (no Admirals Watch median) |
Source: Southwest Florida MLS, closed sales October 13, 2023 to October 13, 2026 (36 months), October 13, 2024 to October 13, 2026 (24 months) and the 12 months to October 13, 2026 as labeled; gaps are our arithmetic on the medians.
Two readings matter. Marina Cove and Spinnaker Pointe trade within $16,000 of each other at the 24-month median, so a buyer comparing them will notice any listing priced above its neighbor. Regatta Landing and Yacht Harbour Cove, both coach homes, sit $390,000 apart (24-month against 36-month medians), and the difference is the marina basin and the building age, which is exactly what our adjustments have to explain.
Fifty-two Windstar homes closed in the 12 months to October 13, 2026, in 15 of the 16 villages, so a buyer touring your village this season has seen recent prices for homes like yours. Request a written opinion of value through our Windstar on Naples Bay home valuation page or call Jesse direct at (239) 898-6072. Buying instead? See how we help buyers purchase in Windstar on Naples Bay, read how we represent buyers in Naples or call Marc at (239) 287-5873.
Under 10 closings in the window a median is not a market, so for the villages with one or two sales we list the sales themselves, with the dates as recorded in the Southwest Florida MLS for the 12 months to October 13, 2026. The villages with three to nine sales are given as sale lists and ranges in the village table above.
Village | Sales in the window | Sales on record (date, price) | What a seller there prices from |
|---|---|---|---|
Clipper Cove | 2 | 2025-12-15 $1,480,000; 2026-03-30 $1,625,000 | The two sales, Ketch Cay and Spyglass Pointe detached sales, the village’s pool homes and their lot and elevation |
Compass Point South | 2 | 2025-12-23 $508,000; 2026-05-11 $430,000 | The two sales, and the village’s 14 sales over 36 months (median $503,500, $405,000 to $730,000), plus Windward Cay and Spinnaker Pointe condominium sales |
Northstar | 2 | 2025-12-10 $1,325,000; 2026-05-22 $1,375,000 | The two sales, the villas’ private pools and bay or mangrove view, and Somerset and Leeward Cay villa sales |
Harrington Sound | 1 | 2026-01-28 $2,075,000 | The lot, the home’s size and age (built 1993 to 2009 across the village), its elevation against a sampled BFE of 8 feet, and Windstar’s six $2,000,000-plus sales |
Spyglass Pointe | 1 | 2026-02-12 $1,775,000 | The sale, Ketch Cay and Clipper Cove detached sales, golf and mangrove frontage, and cabana guest suites where present |
Island at Southpointe | 1 | 2026-06-16 $6,750,000 | The sale, the home’s docks on the access channel, City of Naples taxes and permits, and waterfront estate sales beyond the gate |
A single sale is never a market rate, and we never print a median for one. If your home is in one of these villages, the written opinion of value we prepare reads these sales line by line and adjusts them to your lot, view, size and condition.
Morningstar, 24 condominiums at 3601 to 3717 Haldeman Creek Drive built 1986 to 1988, recorded no closed sale in the 12 months to October 13, 2026 (Southwest Florida MLS). That is why it does not appear among the 15 Windstar village names in the pull. A Morningstar owner prices from the village’s own older sales, which we pull by widening the window, and from Compass Point South and Windward Cay condominium sales a short walk away. Few homes there come up for sale, so the next Morningstar owner who sells should call us first, before the price is set.
Inside a village, these move the number more than square footage:
The adjustment amounts come from closings in your village and the nearest comparable villages, never from asking prices.
Collier County publishes elevation certificates for many Windstar addresses on its Elevation Certificates layer. The eight modern certificates our community guide reads compare as follows against the 2024 BFE at the same spot.
Address | Village | Lowest floor ft NAVD88 | 2024 BFE ft | Lowest floor against 2024 BFE |
|---|---|---|---|---|
2481 Breakwater Way | Regatta Landing | enclosure 8.1; living level 13.8 | 9 | living level plus 4.8 |
2542 Windward Ct | Regatta Landing | enclosure 8.0; living level 14.5 | 9 | living level plus 5.5 |
4500 Lighthouse Ln | Harrington Sound | 9.5 | 8 | plus 1.5 |
3660 Haldeman Creek Dr | Northstar | 8.80 | 8 (nearest sampled) | plus 0.8 |
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) | minus 0.5 |
3292 Lookout Ln | Spyglass Pointe | 8.3 | 9 | minus 0.7 |
Source: the 2020 certificate and 2021 certificate at Regatta Landing, the 2022 certificate at 4500 Lighthouse Ln and the other certificates on the county layer; 2024 BFE from the FEMA NFHL, queried October 10, 2026.
A high lowest floor is a selling point and a low one is a negotiating point, and both belong in the price before a buyer’s insurer finds them. The base flood elevation has also moved: certificates surveyed under the 2012 map, when the BFE on Lookout Lane was 7 feet, can show a home above BFE that now sits below the 2024 BFE of 9. If your certificate predates 2024, we read it against today’s map with you before we list.
The 2026 preliminary county just value on your tax notice is an appraisal figure for tax purposes, not a sale price. Set against each village’s sold median, the gap is wide everywhere, which is why we never price from it. Only villages with 10 or more sales in a 24 or 36-month window have a median here, and the window is named in the last column.
Village | 2026 preliminary median county just value | Sold median (window) |
|---|---|---|
Compass Point South | $410,990 | $503,500 (14 sales, 36 months) |
Spinnaker Pointe | $481,040 | $630,000 (11 sales, 24 months) |
Marina Cove | $532,830 | $646,000 (12 sales, 24 months) |
Windward Cay | $568,856 | no median (9 sales in 36 months) |
Somerset at Windstar | $872,400 | $1,095,000 (10 sales, 24 months) |
Leeward Cay | $861,125 | no median (4 sales in 36 months) |
Regatta Landing | $1,043,725 | $1,310,000 (16 sales, 24 months) |
Clipper Cove | $1,199,956 | no median (7 sales in 36 months) |
Ketch Cay | $990,008 | no median (7 sales in 36 months) |
Yacht Harbour Cove | $1,487,970 | $1,700,000 (11 sales, 36 months) |
Admirals Watch | $1,846,545 | no median (7 sales in 36 months) |
Source: just values from the Florida DOR 2026 preliminary roll, read October 10, 2026; sold medians from the Southwest Florida MLS, closed sales October 13, 2023 to October 13, 2026 (36 months) and October 13, 2024 to October 13, 2026 (24 months) as labeled. Villages with fewer than 10 sales in those windows show their just value with no sold median.
An automated model needs many similar recent sales. Windstar produced 52 closings in a year across 16 villages, and 10 of those villages recorded three or fewer. A model also cannot see a lowest-floor elevation, a marina-basin view, a slip certificate, a new roof or a village’s reserve position, and it does not know that two villages pay City of Naples tax rates. Treat an online estimate as a starting question, and treat our written opinion of value as the answer.
Seller question | Condominium village | Villa village (HOA) | Detached or estate village (HOA) |
|---|---|---|---|
12-month closings and median | 36 at a $1,096,250 median | 8 (no median under 10 sales) | 8 (no median under 10 sales) |
Price range in the window | $350,000 to $3,625,000 | $660,000 to $1,300,000 | $1,375,000 to $6,750,000 |
Who insures the structure | The condominium association | Usually the owner; the village’s documents govern | The owner |
What the buyer’s lender and insurer read | Association budget, reserves, master policy, SIRS and milestone where they apply | Village budget, elevation certificate, wind mitigation | Elevation certificate, wind mitigation, survey |
Statutory regime | Chapter 718 condominium, plus the Chapter 720 master | Chapter 720 village and master | Chapter 720 village and master |
What decides the price | Village, building, floor, view, condition | Village, unit position, condition, pool | Lot, frontage, elevation, size, age, docks |
Source: Southwest Florida MLS for the closing figures (October 13, 2025 to October 13, 2026); the master association recorded compilation and the DBPR condominium extract for the regimes.
We market a Windstar on Naples Bay home with professional photography, cinematic video and drone coverage, full Southwest Florida MLS exposure, our qualified-buyer database and, when an owner wants discretion, off-market capability, and we put the village’s documents, fees and flood record in front of buyers from the first day.
A Windstar buyer is buying a setting as much as a floor plan, so the media has to show where the home sits: on a Tom Fazio fairway, on a lake, on the mangroves of Haldeman Creek, on the Southpointe marina basin or on Naples Bay. Drone footage shows the gate, the clubhouse and the water in one frame, which is how a buyer from out of state understands the community before visiting. For a condominium we show the building, the village pool and the view at the hour it is best; for an estate, the frontage and the dock. We do not publish a view claim we cannot photograph.
Listings with their documents ready get fewer surprises. For every Windstar home we assemble the master declaration, bylaws and 2018 Rules and Regulations from the master association’s Documents page, the village’s declaration, rules and current budget, and a request for both estoppel certificates. For a condominium we add the association’s insurance declarations and, for Windward Cay’s three-story buildings and Compass Point South, the milestone and structural integrity reserve study reports. For a detached home or villa we add the elevation certificate (many are on the county’s layer), a wind mitigation report and the survey. A buyer who can see those papers on day one can write a clean offer.
Because the Windstar Club is optional, every listing has to say what it is and is not. We state plainly that buying the home does not make the buyer a member, list the club’s four published categories (Full Golf, WOW, Social Summer Golf and Social, per the club’s Membership Types page) and the club’s stated 350-member golf cap, and point the buyer to the membership office for current terms, because the club’s latest published fee schedule is from 2023. If you are a member, we ask the club in writing, before you list, what happens to your membership when you sell.
Windstar is gated, and showings have to clear the gate. Guests and vendors are admitted when the owner registers them, through the TekControl visitor system linked from the master association’s Documents page, and the main entry gate stays open on weekdays from 8 a.m. to 6 p.m. under the 2018 Rules and Regulations. The same rules sign association-approved open house signs out at the guardhouse and keep for-sale signs off master property, with yard signs governed by your village’s rules. Marc registers every showing, inspector and appraiser in advance so no buyer is turned around at the gate.
About 45.5% of Windstar homes, 281 of 618, carried a homestead exemption on the 2026 roll, a fair stand-in for year-round ownership (our arithmetic on the Florida DOR 2026 preliminary roll). The share ran from 75% at Admirals Watch and 67% at Regatta Landing to 28% at Compass Point South and 21% at Morningstar. That tells us who buys in each village: a lock-and-leave winter buyer for the older condominiums, and a year-round household for the newer coach homes and estates. We schedule showings and media for the buyer your village actually draws, and we prepare a remote showing package for buyers who are not in Florida.
Some Windstar owners, particularly on the Island at Southpointe, at Admirals Watch and in Harrington Sound, prefer a quiet sale inside a gated community. We can run a private or off-market listing to our qualified-buyer database and selected agents, and we will tell you plainly what it costs in exposure compared with a full MLS launch. Confidential conversations are welcome at (239) 898-6072.
You get showing activity, buyer-agent feedback and a plain comparison of your days on market against the median for your village and product (59 days across Windstar in the latest 12 months). If the market answers a price with silence, we tell you in week four, not month four, and we show you the village sales that support the next step.
In Windstar on Naples Bay, Jesse McGreevy and Marc Comisar negotiate every offer personally, from price and closing date to inspection repairs, flood and wind insurance quotes, association document review and slip transfers. With sales in the window ranging from $350,000 to $6,750,000, the negotiation turns on the evidence for your village, and a partner-level negotiator protects it.
The partners who list your home are the people who sit across from the buyer’s agent. We read every offer for what it says about the buyer: how much the price depends on a financing contingency, on a flood or wind insurance quote, on a club membership decision or on the buyer’s own sale, and what the buyer’s attorney will ask the master and village associations for. We answer in writing and we tell you when to hold and when to move.
On a condominium, the buyer has the right to review the governing documents and a frequently asked questions sheet under section 718.503, Florida Statutes, and the buyer’s lender and insurer will read the association’s budget, reserves and master policy. On a villa or detached home, a buyer’s insurance quote, the elevation certificate and the roof decide whether the deal holds together. We negotiate those periods short, schedule the inspector early and keep your closing date intact.
Since August 17, 2024, an offer of buyer-broker compensation can no longer be advertised on the MLS, and buyers must sign a written agreement stating the buyer agent’s compensation before touring, according to the National Association of REALTORS. Commissions are negotiable and not set by law. A seller may still offer to pay or contribute toward the buyer’s agent off the MLS, and may still offer buyer concessions on it. We explain the options and the cost of each before you decide.
Many Windstar sellers want to close around a travel schedule, a northern move-out date or the end of the winter season, and in this window June 2026 was the busiest closing month, with 10 of the 52 closings. A buyer who needs a lender, a flood quote and a village document review has a different clock than a cash buyer, and the contract date should reflect which one you are facing. We trade price for time deliberately, not by accident.
A lender’s appraiser looks first at recent closed sales in the same village and product. In Windstar that can mean three sales, or one. We build that comparable set before you list, including the sales from neighboring villages an appraiser will be forced to adjust, so the price we recommend is one a financed buyer’s appraisal can support. If a low appraisal arrives anyway, we have the evidence for a reconsideration, a renegotiation or a cash-buyer path ready.
The Windstar on Naples Bay sales that matter most are the ones in your own village and product. Below are the twelve most recent closings in the Southwest Florida MLS pull, from a $6,750,000 Island at Southpointe estate to a $507,500 Marina Cove condominium, then five sales and village patterns worked through.
Data updated: October 2026 (Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026)
Closed | Village | Product | Sold price | Days on market | Sale-to-list |
|---|---|---|---|---|---|
2026-08-25 | Regatta Landing | Coach-home condominium | $1,102,000 | 68 | 88.2% |
2026-08-17 | Regatta Landing | Coach-home condominium | $1,150,000 | 19 | 92.1% |
2026-07-10 | Yacht Harbour Cove | Marina-basin coach-home condominium | $1,200,000 | 38 | 87.0% |
2026-07-07 | Regatta Landing | Coach-home condominium | $1,090,500 | 100 | 91.3% |
2026-06-30 | Yacht Harbour Cove | Marina-basin coach-home condominium | $2,250,000 | 157 | 112.8% |
2026-06-30 | Yacht Harbour Cove | Marina-basin coach-home condominium | $1,610,000 | 106 | 85.0% |
2026-06-30 | Marina Cove | Coach-home condominium | $674,000 | 60 | 97.0% |
2026-06-26 | Ketch Cay | Single-family courtyard home or villa | $1,750,000 | 1 | 95.9% |
2026-06-24 | Marina Cove | Coach-home condominium | $715,000 | 7 | 95.5% |
2026-06-23 | Marina Cove | Coach-home condominium | $507,500 | 373 | 92.3% |
2026-06-16 | Island at Southpointe | Waterfront estate, City of Naples | $6,750,000 | 157 | 90.2% |
2026-06-16 | Leeward Cay | Attached villa | $1,137,000 | 25 | 98.9% |
Source: Southwest Florida MLS, closed sales October 13, 2025 to October 13, 2026, pulled October 13, 2026; product from each village’s recorded form of ownership. Sale-to-list is the sold price over the final list price, and days on market are as recorded for each closing.
This is an MLS-recorded sale on the Island at Southpointe, ten waterfront estates at 1300 to 1617 Gulfstar Drive South on a small island in the Southpointe marina basin, reached over a gated stone bridge and inside the City of Naples (tax code 0004, 9.0514 mills for tax year 2025). It closed at $6,750,000 on June 16, 2026, after 157 days on market and at 90.2% of its $7,480,000 final list price, the highest Windstar price in the window and the only sale above $3,625,000. The village had no other sale in the 12 months, so it has no median. A seller there prices from the home’s lot, docks on the access channel and size (the village’s living area runs 3,723 to 17,120 square feet on the 2026 roll), from the two other single-sale estate villages, and from the buyer’s lender and insurer, not from the $1,200,000 community median.
Admirals Watch, 16 bayfront condominiums at 1500 to 1650 Star Point Lane with private elevators, two- and three-car garages and eight boat slips (master association Admirals Watch page), recorded three closings between November 7, 2025 and January 21, 2026: $3,625,000, $2,935,000 and $2,375,000. Three of 16 units in about eleven weeks is a brisk pace for a building that size, and the $1,250,000 spread between them shows how much floor, view and slip rights move the number. The $3,625,000 sale was the highest condominium price in Windstar in the window.
Regatta Landing led Windstar with 9 closings, from $1,090,500 on July 7, 2026 to $1,849,000 on April 23, 2026, a $758,500 spread inside one village of 64 coach homes built 2016 to 2021. Two closed at $1,200,000, in October 2025 and June 2026. The spread follows size (living area runs 2,348 to 3,854 square feet on the 2026 roll), position on Haldeman Creek and finish. The village’s design also helps a seller: its two published elevation certificates show living levels at 13.8 and 14.5 feet NAVD88, about 5 feet above the 2024 BFE of 9, and that belongs in the listing.
Marina Cove’s 6 sales ran from $507,500 to $745,000, the narrowest spread of any Windstar village with more than three sales, and three of them closed in one week in June 2026 ($507,500, $715,000 and $674,000). That makes Marina Cove the easiest Windstar village to price from comparables and the hardest one to overprice: a buyer has seen the band. It is also the one village sampled mostly in shaded Zone X (seven of eight points), outside the federal mandatory-purchase rule, a fact we put in front of financed buyers.
Windward Cay’s four sales, $350,000 and $665,000 on March 17, 2026, $725,000 on April 17, 2026 and $1,075,000 on February 12, 2026, are spread wide because the village is not one product. Its 48 units were built in phases from 1984 to 2004: 14 units from 1984 to 1987, a 16-unit building at 4650 Yacht Harbor Drive in 1998 and three six-unit buildings in 2003 and 2004. A Windward Cay seller prices from the sales in the same building phase, size and floor, and from the milestone status of the three-story buildings, not from a single village-wide figure.
Two Yacht Harbour Cove coach homes on the marina basin closed on June 30, 2026, at $2,250,000 and $1,610,000, and a third closed ten days later at $1,200,000. Three closings in about two weeks from a 28-home village, with a $1,050,000 range among them, show that a marina-basin address alone does not set the price: size (2,437 to 2,961 square feet on the 2026 roll), position on the basin, slip rights and finish do. A buyer’s appraiser sees all three, and so do we when we price the next one.
An appraiser’s first question is which sales within the village closed recently and how they compare in size and condition. With 10 or more sales in a window that is a median and a range; with fewer, it is a list of sales like the ones above and the nearest comparable village. We assemble the same set before you list, and we add the flood, fee and slip facts that explain why one Windstar sale is not another.
Selling a Windstar on Naples Bay home in Collier County costs a negotiated commission, documentary stamp tax at $0.70 per $100 of price, at least two estoppel certificates, any association balance and a property tax proration, plus any mortgage payoff. In Collier County the buyer customarily pays the owner’s title policy, and the contract controls.
Line item | Who customarily pays in Collier County | Amount or rule |
|---|---|---|
Listing commission | Seller | Negotiable; no rate is set by law |
Buyer-agent compensation | Seller, if the seller chooses to offer it | Negotiable; offered off the MLS since August 17, 2024 |
Deed documentary stamp tax | Seller | $0.70 per $100 of price, or portion thereof |
Owner’s title insurance policy | Buyer, who usually chooses the closing agent | Premium set by state rule; the contract controls |
Master association estoppel certificate | Seller | Fee within the limits of section 720.30851; the association’s schedule is not published |
Village or condominium estoppel certificate | Seller | Fee within the limits of section 718.116 or 720.30851; not published |
Dock or marina association documents, where a slip transfers | Per the slip documents | Not published |
Unpaid master or village assessments | Seller | Stated on the estoppel certificates and paid at closing |
Property tax proration | Credit from seller to buyer | The seller’s days of ownership in the tax year |
Mortgage payoff, if any | Seller | Loan balance plus per-diem interest |
The split is custom, not law: the purchase contract you sign controls every line. The estoppel rules are in section 718.116, Florida Statutes for condominiums and section 720.30851 for homeowners associations, and none of Windstar’s associations publishes its fee schedule.
The deed tax is $0.70 per $100 of the price, or portion thereof, under section 201.02, Florida Statutes, and the Florida Department of Revenue shows the method. At Windstar’s community median, the village medians that reach 10 sales in the 24 or 36-month window named in each row, one Admirals Watch sale and the top sale from the 12 months to October 13, 2026, it works out as follows (our arithmetic):
Price (Southwest Florida MLS figure) | Documentary stamp tax |
|---|---|
$503,500 (Compass Point South median, 14 sales over 36 months) | $3,524.50 |
$646,000 (Marina Cove median, 12 sales over 24 months) | $4,522.00 |
$1,200,000 (Windstar median) | $8,400.00 |
$1,310,000 (Regatta Landing median, 16 sales over 24 months) | $9,170.00 |
$2,935,000 (Admirals Watch, the middle of its three 12-month sales) | $20,545.00 |
$6,750,000 (top sale, Island at Southpointe) | $47,250.00 |
Because the tax scales with price, it is one of the two largest seller costs alongside the commission.
Every Windstar home belongs to the master association, which issues its own estoppel certificate stating the master assessment balance and any amounts due, and most homes also belong to a village association or condominium, which issues a second certificate for its own assessments. If a Regatta Landing dock slip goes with the sale, the slip moves by assignment of the Dock Slip Certificate on the dock association’s Dock Slip Certificate Assignment form, recorded as Exhibit P at Official Records Book 5448, Page 1149, which brings that association into the closing too. Each certificate has its own turnaround, so we order them as soon as you are under contract.
At the master level, the board proposed a resale capital contribution in 2023 (October 2023 newsletter; President’s remarks, October 2023), and the amendment certificate recorded in January 2024 (Official Records Book 6322, Page 2115) does not contain one. 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, and who pays it is a contract term, so we settle it in the offer.
Florida property taxes are assessed on a calendar year and paid in arrears, so at a closing before the bill is paid the seller credits the buyer for the days the seller owned the home in the tax year; the title agent usually estimates from the prior year’s bill. In Windstar the rate behind that credit depends on the village: 12.6162 mills for most of Windstar, 13.6162 mills for Regatta Landing (which adds the 1.0000-mill Haldeman Creek MSTU) and 9.0514 mills for Admirals Watch and the Island at Southpointe, all for tax year 2025 per the 2025 Collier Taxing Authority Code Descriptions.
If you are a Windstar Club member, your dues are separate from the sale. 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” (Windstar Club 2023 resident membership offer and fee pages). On that 2023 schedule, Social dues were $6,645 a year and Social Summer Golf dues $9,545 a year. How a membership transfers or is resigned when you sell, and any equity refund, sits in the club’s membership documents, which the club has not published, so we ask the membership office for the current terms in writing before you set a closing date.
Southpointe Marina slips are separate parcels on the county roll: the 2026 preliminary roll carries 73 slip parcels at the marina, one more than the 72 slips the club and the 1988 PUD describe, with a median 2026 preliminary county just value of $251,497 per slip parcel, which is an appraisal figure and not a sale price. Who may buy a slip and on what terms is set by Southpointe at Windstar Marina Association, Inc.’s documents. Regatta Landing slips are held by Dock Slip Certificate outside the condominium, and under the 2013 annexation terms they are offered first to Regatta owners, then to other Windstar owners, and to outside buyers only after a year. We read the slip documents before you decide whether to sell the slip with the home or separately.
Your commission is negotiated, in writing, with no rate set by law. We prepare a written net sheet at your pricing options before you list, and you will see the commission, the documentary stamp tax, the estoppel fees, any association balance, the proration and your payoff on one page. Whether to offer buyer-agent compensation is a pricing decision, not a formality, and we show the cost with and without it.
A Florida seller must disclose known facts that materially affect value and are not readily observable, under the Florida Supreme Court’s decision in Johnson v. Davis, and an as-is clause does not remove that duty; storm damage and its repair history fall squarely in that category. Sellers also give the buyer the property tax disclosure summary required by section 689.261, Florida Statutes, because a new owner’s taxable value is reset after a sale. Condominium sellers provide the governing documents and frequently asked questions sheet under section 718.503.
Windstar mixes a Chapter 720 master association with nine Chapter 718 condominiums, so the homeowners’ association disclosure rule forks. Section 720.401, Florida Statutes requires a disclosure summary to be given to a prospective purchaser before the contract is signed (“before executing the contract for sale”), not at closing. On a resale it is supplied by the parcel owner. The contract must carry the statute’s voidability clause in conspicuous type, and if the summary is not given before signing, the buyer may cancel within 3 days after receiving it or before closing, whichever comes first, a right that cannot be waived and ends at closing. Section 720.401(2) states that the section does not apply to associations under chapters 718, 719, 721 or 723. In practice:
This is information, not legal advice; your closing agent or attorney decides what applies to your sale, and we prepare the documents either way.
The covenant side sits in the master declaration. Article 7.1 requires owners to give purchasers copies of the Declaration, Bylaws and Rules (master association recorded compilation), so the seller owes the documents. On the cost side, no master resale capital contribution appears in the amendment recorded in January 2024, while the Regatta Landing declaration defines capital contribution assessments whose amount is not published. Put together: the seller owes the disclosure and the documents before signing, and any transfer charge a village or the master association imposes shows on its estoppel certificate, payable at closing by whoever the contract names.
A Windstar on Naples Bay owner pays the master assessment ($4,130 per home in 2025, billed $1,032.50 a quarter), a village or condominium assessment, and property tax at one of three millage rates; there is no Community Development District, and club dues and slip dues apply only to owners who chose them.
Layer | Amount | Who pays | Source |
|---|---|---|---|
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 | Every home, one equal share | 2025 Annual Meeting outline, March 31, 2025 |
Village or condominium assessment | Varies; Compass Point South published $1,968 a quarter in 2021, including its share of the master assessment | Members of that village | |
Windstar Club (optional) | 2023 schedule: Social initiation $10,000 and dues $6,645 a year; Social Summer Golf initiation $20,000 and dues $9,545 a year | Club members only | Club 2023 resident offer and fee pages |
Southpointe Marina and Regatta dock dues | Not published | Slip owners | The marina and dock associations’ documents govern |
Community Development District | None | None | County CDD layer, queried October 2026 |
Property tax | 12.6162, 13.6162 or 9.0514 mills by tax code (tax year 2025) | All owners | 2025 Collier Taxing Authority Code Descriptions |
County non-ad valorem charge | $261.91 on many parcels (2025 roll) | Owners of those parcels |
The 2026 master assessment sits in the owner-only financials and on the master estoppel certificate, so a buyer reads that certificate for the current figure; we never carry the 2025 number forward as if it were current. Regatta Landing and Compass Point South collect the master share inside their own budgets, so one quarterly bill there covers both layers.
Buyers will see that the master assessment went from $3,250 in 2024 to $4,130 in 2025, an increase of $880 or 27.1%, so we explain it before they ask. Of that $880, $780 is the new bulk Hotwire line (500/500 Mbps internet, two TV boxes and a 199-channel lineup under a 10-year contract from March 1, 2025, per the master association’s Communications page). Strip the Hotwire line out and the rest of the assessment rose $100 a year. A buyer comparing Windstar with a community that bills internet separately is comparing the wrong numbers until that line is pulled out.
The master association’s December 31, 2024 balance sheet showed replacement reserve cash of $743,918, a hurricane reserve of $632,382 and operating cash of $246,693, against a term loan payable of $287,471 that the March 2025 deck said the board might pay off in 2025 (2025 Annual Meeting outline). The same deck projects a reserve outlay of about $1.70 million in 2030 for docks, the channel, a road and marina-entrance dredging, funded under the reserve plan as projected, and the 2025 Committee Reports Binder puts the master dock dredge at about $400,000. No special assessment is announced in those documents. A seller who can show a buyer the reserve position answers the question that otherwise stalls a contract.
These are illustrations, not bills; the tax collector’s bill and each association’s estoppel certificate control. Each uses tax year 2025 millage and the 2025 master assessment.
Homestead exemptions change taxable value, and a buyer’s first bill is set on the purchase-year assessment, not the seller’s, which is why section 689.261 requires the property tax disclosure summary.
You can get your free Windstar on Naples Bay home valuation in about 60 seconds, then talk it through with Jesse. We read the closed sales in your village and the nearest comparable villages, the active listings, your elevation certificate and the association paperwork a buyer’s lender will ask for, and send a written opinion of value. Or call Jesse direct at (239) 898-6072.
Enter your address in the valuation form below the page’s top banner and we start with the closings that match your product: your village and building for a condominium, your village, lot and frontage for a villa or detached home. For a faster answer, use our dedicated Windstar on Naples Bay home valuation page, which is built around the same Southwest Florida MLS pull as this page. Prefer to talk? Call Jesse direct at (239) 898-6072, text or call. Confidential conversations welcome.
You receive a written opinion of value with the closings we relied on, the active listings you compete with, the adjustments we made for view, elevation, condition and slip rights, and a net sheet at two or three price points with the documentary stamp tax and estoppel lines filled in. We also send a short checklist of the master, village and slip documents your sale will need. There is no obligation, and a valuation is not a listing agreement.
McGreevy and Comisar is a top-reviewed Windstar realtor, and every quote below is a five-star review on our Google Business Profile.
★★★★★ “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
★★★★★ “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
Talk to McGreevy and Comisar before you list your Windstar home, and get a written price, plan and net sheet with no obligation.
A Windstar on Naples Bay seller should know who governs each layer, what the club and the Keewaydin beach include, which leasing, pet and architectural rules a buyer inherits, how the flood, insurance and inspection facts read village by village, and what is changing outside the gate. Each fact below is tied to a public record.
Windstar on Naples Bay Master Association, Inc. (Sunbiz N01881, filed March 9, 1984 and renamed in 1998 and 2009) is the Chapter 720 master association every owner belongs to, self-managed from 1700 Windstar Blvd per its Property Management page. Its base document is the Second Amended and Restated Master Declaration recorded November 24, 2009 at Official Records Book 4512, Page 2575, followed by the 2013 Regatta Landing annexation (OR 4933, PG 1493), the 2020 leasing amendment (OR 5764, PG 966) and the December 2023 amendment recorded January 19, 2024 (OR 6322, PG 2115). Bylaw 4.1 sets a nine-director board. Below it, nine condominium associations and seven homeowners associations govern the villages, and the Windstar Club and the Southpointe marina are separate “Recreational Associations” that no owner joins by buying a home.
The Windstar Club (Windstar Club, Incorporated, Sunbiz N00119, filed December 1, 1983) describes itself as “an equity, Member-owned golf and Country Club that accepts non-resident Members.” It publishes four categories, Full Golf, WOW (“Waiting on Windstar”), Social Summer Golf and Social, and states a golf membership cap of 350 with tee times reservable up to 7 days ahead (Our Club). Its most recent published fee schedule is from 2023: Social initiation $10,000 (with a resident special of $3,000 through December 31, 2023) and dues of $6,645 a year; Social Summer Golf initiation $20,000 and dues of $9,545 a year; a food and beverage minimum of $1,400 family or $700 single; and a reference to a “Full Golf Membership Contribution ($85,000).” Those are 2023 figures; current terms come from the club’s membership office. Members approved a $13 million club renovation in October 2021, per Club + Resort Business.
The club’s 18-hole course is a Tom Fazio design that the club dates to 1983, with eight sets of tees (Windstar Club Golf), on 129.48 acres of club-owned land. Southpointe Marina has 72 slips and “can accommodate yachts up to 70 feet,” per the club’s Bay Life page, and NOAA’s Coast Pilot 5, Chapter 4 places the fixed US 41 bridge (10-foot clearance) at the head of Naples Bay, north of Windstar, so the bay docks run south to Gordon Pass without passing under it. The master association owns about 5 acres on Keewaydin Island and the Keewaydin Queen III shuttle “for the benefit and enjoyment of Windstar residents and non-resident members of the Club and Marina” (Keewaydin Beach and Shuttle), with trips offered November 1 through July 15 from the 2025/26 season. Every owner keeps that beach whether or not they join the club, which belongs in every listing.
Article 7.1 of the master declaration, rewritten in 2020, allows leases of the whole unit only, for not less than 30 days or one calendar month and not more than one year, no more than three times in a calendar year, with 20 days’ notice and a $145 master lease application (2022 lease application). Short-term and vacation rentals are not allowed anywhere in Windstar. Villages can be stricter: Regatta Landing allows no more than two leases in any 12 months, and Compass Point South requires board approval of every lease (Compass Point South Q and A, 2021). For the other villages, the Declaration and Rules of that village govern. An investor buyer reads these first, so we put them in the listing package.
The 2018 master rules require pets on leashes and keep them off the golf course, the Keewaydin shuttle and, from October 15 to July 15, the island property; they set no weight or number limit, so those come from the villages. Compass Point South allows owners one dog or cat of 25 pounds or less and no tenant pets, and Regatta Landing allows two pets each under 60 pounds (Regatta Landing rules, September 5, 2025). Every exterior change needs written village approval and then the master Architectural Review Committee under the Design Guidelines and Tree Policy approved May 26, 2022: submit at least 30 days ahead, approval effective on the 7th day. A seller with unapproved exterior work should resolve it before listing.
Village | Points sampled | Zones | BFE ft NAVD88 | NFIP community |
|---|---|---|---|---|
Regatta Landing | 5 | AE | 9 | Collier County |
Marina Cove | 8 | 7 shaded X, 1 AE | 8 (at 5010 Marina Cove Dr) | Collier County |
Spinnaker Pointe | 4 | AE | 9 | Collier County |
Somerset at Windstar | 4 | AE | 9 | Collier County |
Yacht Harbour Cove | 3 | AE | 8 | Collier County |
Windward Cay | 6 | AE | 8 and 9 | Collier County |
Compass Point South | 3 | AE | 9 | Collier County |
Ketch Cay | 5 | AE | 8 | Collier County |
Clipper Cove | 4 | AE | 9 | Collier County |
Admirals Watch | 4 | AE | 8 to 9 | City of Naples |
Harrington Sound | 6 | AE | 8 | Collier County |
Spyglass Pointe | 2 | AE | 9 | Collier County |
Island at Southpointe | 3 | AE | 8 to 9 | City of Naples |
Northstar | 4 | 3 AE, 1 shaded X | 8 to 9 | Collier County |
Morningstar | 3 | 2 AE, 1 shaded X | 8 | Collier County |
Leeward Cay | 0 direct | neighbors AE 8 to 9 | n/a | Collier County |
Source: FEMA NFHL flood hazard layer, FIRM panel layer and political jurisdictions layer, queried October 10, 2026, panels 12021C0581J and 12021C0582J effective February 8, 2024. Every point also returned Evacuation Zone A on the Collier evacuation zone layer. The points are address points, not buildings, so the lender’s flood determination and the home’s elevation certificate decide your parcel.
FEMA issued preliminary flood map data for Collier County on March 20, 2025, per the FEMA Preliminary NFHL. For Windstar it changes the paper, 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. No effective Letter of Map Revision covers Windstar, and no Windstar building has a Letter of Map Amendment on file. A seller can tell a buyer, with a source, that the coming map does not move the village’s zone.
A federally backed mortgage on a building in Zone AE requires flood insurance. NFIP policies in force June 2025 to July 2026 in the census block group that contains Windstar (which also holds older streets outside the gates) ran a median premium of $1,562 for houses and $842 for condominium unit-owner policies, per OpenFEMA NFIP Policies, and Collier County and the City of Naples both carry Community Rating System class 6, a 20 percent discount inside the Special Flood Hazard Area under FEMA’s Community Rating System schedule. Windstar-specific wind premiums are not published, so we give buyers the wind mitigation report and, for a condominium, the association’s master policy declarations, and we do not quote premiums ourselves.
The National Hurricane Center’s Hurricane Ian report records a USGS sensor at the Gordon River Bridge, about 3.4 kilometres north of Windstar on the same bay, at 7.1 feet NAVD88; no surveyed Ian high water mark sits inside the Windstar gates. In 2024 the NOAA Naples Bay, North gauge peaked at 4.71 feet NAVD88 in Helene and 5.77 feet in Milton. In the NFIP claims for the census block group that contains Windstar, Ian produced about $8.77 million in net payments, of which about $1.70 million went to buildings built 1980 or later, a proxy for Windstar-era construction (OpenFEMA NFIP Claims). Buyers ask about the specific home, so we gather your repair records, permits and any claim history before listing.
Florida requires a structural integrity reserve study at least every 10 years for condominium buildings of three habitable stories or more under section 718.112, Florida Statutes, and a milestone inspection under section 553.899. In Windstar, Windward Cay buildings 4450, 4600 and 4650 Yacht Harbor Drive and Compass Point South’s four buildings show “Milestone Completed, Cycle Completed,” next inspection 2033, and Compass Point South posts its Structural Integrity Reserve Study dated May 29, 2024, with minimum 2025 reserve funding of $118,650. Regatta Landing’s buildings are capped at two stories, Admirals Watch’s status sits with the City of Naples and is not published, and the Island at Southpointe is an HOA, not a condominium.
Every Windstar address the district’s lookup returned for 2026-27 is zoned to Avalon Elementary (graded B in 2026), Gulfview Middle (A) and Naples High (A), including the two City of Naples villages (Collier County Public Schools address lookup; FLDOE 2025-26 school grades, as of September 1, 2026). Avalon is about 0.8 miles and 3 minutes from the entrance. A family buyer should confirm the exact address with the district before signing.
Destination | Drive from the Windstar entrance |
|---|---|
Naples Botanical Garden | about 0.7 mi, 2 min |
Publix, Shops at Hammock Cove | about 1.8 mi, 5 min |
Fifth Avenue South | about 3.1 mi, 7 min |
NCH Baker Hospital emergency department | about 4.0 mi, 10 min |
Naples Pier | about 4.4 mi, 10 min |
Naples Airport | about 4.4 mi, 11 min |
I-75 Exit 101 (Collier Boulevard) | about 9.4 mi, 16 min |
Southwest Florida International Airport (RSW) | about 36.5 mi, 51 min |
Source: free-flow routing from Windstar Boulevard and Bayshore Drive on the OSRM public routing service, run October 10, 2026; in season, allow more time. Homes at the Southpointe end add about 3 to 4 minutes to every trip. Downtown in under 10 minutes is one of Windstar’s strongest selling points, and we lead with it for buyers coming from communities closer to I-75.
Windstar is built out, so change comes from outside the gate. The Bayshore Boardwalk to Sugden Regional Park opened on February 26, 2026, about 0.16 miles from the gate, and the Bayshore CRA posted Invitation to Negotiate 26-8663 for outparcels on the county’s 17-acre site across Bayshore Drive on July 15, 2026, with no award reported as of October 10, 2026. Within about a mile, the Board approved The Halcyon, 66 condominium units and a 120-slip marina on Rock Creek (BCC legal ad), and the 90-home Windward Landing RPUD to the south, a separate project from Windstar’s Windward Cay (BCC legal ad). None adds a golf course, a private beach or a master gate, so Windstar resales compete on a different footing, and we say so to buyers touring both.
Buyers often tour Royal Harbor, an ungated City of Naples canal neighborhood with no mandatory HOA, in the same week as Windstar. Our Royal Harbor page records 21 single-family closings at a $2,975,000 median in its own 12-month window to September 24, 2026, against Windstar’s 8 detached single-family sales from $1,375,000 to $6,750,000 in the 12 months to October 13, 2026, and a $1,600,000 median across 22 detached sales over 24 months (different windows, both Southwest Florida MLS). For a Windstar estate on the water, the buyer’s question is whether they want a gate, an optional club and a master association, or a private canal lot with no mandatory dues; we position a waterfront Windstar listing against that choice directly. Buyers also compare Port Royal, which the club describes as “directly across” Naples Bay, and newer construction at Isles of Collier Preserve.
Windstar on Naples Bay has a full community guide, a dedicated home valuation page and a buyer page, plus our Naples-wide seller guide. This section links each of them, along with the neighboring communities Windstar buyers compare, so a seller can see exactly what a buyer reads before calling.
Our Windstar on Naples Bay community guide covers the history, governance, all 16 villages, the club, golf, boating, the Keewaydin beach, flood zones, schools and drive times in full. If you want a number now, use the dedicated Windstar on Naples Bay home valuation page. If you are also looking to buy, our Windstar on Naples Bay buyer page is written for that side of the move, and Marc Comisar can be reached at (239) 287-5873.
If you own more than one Naples property, or you are comparing Windstar with another community before you list, start with our guide to selling your home in Naples, which sets out the same pricing, marketing and negotiation process for the whole city. Buyers moving from Windstar into another Naples neighborhood can read how McGreevy and Comisar represent buyers or call Marc at (239) 287-5873.
Windstar buyers often look at Royal Harbor and Port Royal on the water, and at gated communities to the east such as Isles of Collier Preserve, Treviso Bay and Lely Resort. Knowing which of them your buyer is also viewing shapes how we position your home.
These are the questions Windstar on Naples Bay sellers ask most, answered from the Southwest Florida MLS pull for the 12 months to October 13, 2026, the master association’s published documents, county and state records and our own process. Call Jesse at (239) 898-6072 for the version that applies to your village.
It starts with your own village’s recent sales, not the community figure. In the 12 months to October 13, 2026, no Windstar 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) (Southwest Florida MLS). For a written opinion of value built on your village, floor plan, elevation certificate and view, request a free Windstar on Naples Bay home valuation or call Jesse.
Interview more than one agent and compare what each can show you. McGreevy and Comisar are Top 1% Real Estate Agents Nationally Since 2008 and lead the #1 Team in Southwest Florida since 2012, with over $900 million in sales between Jesse and Marc. Ask every agent for the closed sales in your village, how they read the master and village estoppel certificates, and how they will answer the club question.
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). The average was $1,353,433, pulled up by a few estate and bayfront sales, so the median is the better guide, and your village’s own figure is better still.
The median days on market for the 48 Windstar closings that carry a days-on-market figure in the 12 months to October 13, 2026 was 59, up from 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 varies by village and price band, and a listing with the estoppel figures, the elevation certificate and any condominium reports ready avoids the delays that come from a buyer waiting on paperwork.
For a home priced to its own village, yes. Windstar recorded 52 closings in 12 months, with sales in 15 of its 16 villages and six at $2,000,000 or more, and because both Windstar PUDs are built out, your buyer is comparing resales, not a builder’s incentives. Active inventory at the October 13, 2026 pull was 15 listings, or 3.5 months of supply at the last 12 months’ closing pace, which we check for your village before setting a price.
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). It is Windstar’s newest village, 64 coach homes built 2016 to 2021, and its published elevation certificates show living levels about 5 feet above the 2024 base flood elevation.
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), the tightest band of any Windstar village with more than three sales (Southwest Florida MLS). Seven of its eight sampled address points are shaded Zone X, outside the federal mandatory flood purchase rule, a fact worth putting in front of financed buyers.
Somerset at Windstar recorded 5 sales from $660,000 to $1,300,000 (24 months: 10 sales, median $1,095,000), and Leeward Cay 3 sales of $800,000, $1,137,000 and $1,270,000, in the 12 months to October 13, 2026 (Southwest Florida MLS). Both are homeowners-association villa groups built 1987 to 1990, and a Leeward Cay sale at $1,137,000 sits close to the Somerset 24-month median, so a buyer comparing them will notice any listing priced above its neighbor.
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.
Yacht Harbour Cove’s 28 marina-basin coach homes recorded 5 sales from $1,200,000 to $2,250,000 (36 months: 11 sales, median $1,700,000), and Admirals Watch’s 16 bayfront condominiums recorded 3 sales of $2,375,000, $2,935,000 and $3,625,000, in the 12 months to October 13, 2026 (Southwest Florida MLS). Admirals Watch lies inside the City of Naples, with the lowest of Windstar’s three tax rates.
Ketch Cay recorded 3 sales ($1,375,000, $1,525,000 and $1,750,000) and Clipper Cove 2 sales ($1,480,000 and $1,625,000) in the 12 months to October 13, 2026; Spyglass Pointe recorded one sale, at $1,775,000, too thin to read as a market rate (Southwest Florida MLS). All three are detached homeowners-association villages, so lot, pool, view and elevation move each price.
We list the sales rather than print a median. Harrington Sound, Spyglass Pointe and the Island at Southpointe each had one sale in the window, Northstar, Clipper Cove and Compass Point South two each and Morningstar none, so we widen the window for the village’s own older sales, adjust the nearest comparable villages inside Windstar for fees, flood zone and size, and test the result against the top of the Windstar market.
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 1,414 square foot Compass Point South condominium and a 5,413 square foot Island at Southpointe estate (the village medians on the 2026 roll), so compare against your own village’s sales rather than the community figure.
The busiest closing 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). That is one year of data, so read it as this window’s pattern, not a rule; closings trail contracts by several weeks.
The main seller costs are the negotiated commission and the documentary stamp tax of $0.70 per $100 of price, which is $8,400 at the $1,200,000 Windstar median. Add the estoppel fees, any balance owed to the master and village associations, the property tax proration and any payoff. In Collier County the buyer customarily pays the owner’s title policy, and the contract controls. We prepare a written net sheet before you list.
In Collier County the buyer customarily pays the owner’s title policy and usually chooses the closing agent; the purchase contract controls, and it can say otherwise. 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. Your title agent’s settlement statement is the final word.
At least two: one from the master association and one from your village association or condominium. A third comes in when a Regatta Landing dock slip transfers, because the slip moves by assignment of the Dock Slip Certificate on the dock association’s form (Exhibit P, OR 5448 PG 1149). None of Windstar’s associations publishes its estoppel fee schedule, and each certificate has its own turnaround, so order them as soon as you are under contract.
The master board proposed a resale capital contribution in 2023, and the amendment certificate recorded in January 2024 (OR 6322, PG 2115) does not contain one. 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, and the contract decides who pays it.
Not automatically, because the membership is not tied to the house. The club states that residents are not required to be members, and Section 1.5 of the master declaration gives no owner club rights by owning a home. Resignation, transfer to your buyer, any equity refund and when dues stop are set by the club’s bylaws and membership documents, which the club has not published, so ask its membership office in writing before you list.
The club’s bylaws govern, and its 2023 fee pages state that the “Windstar Club’s Bylaws does not permit any refund or cessation of fees during the membership year.” On that 2023 schedule Social dues were $6,645 a year. Because the timing of a sale and the membership year may not line up, ask the club’s membership office for the current terms before you set a closing date.
Yes, because Windstar is not bundled and buyers want to know their options. We state in the listing that buying the home does not make the buyer a member, list the club’s four published categories and its 350-member golf cap, and point golfers to the membership office, since the latest published fee schedule is the 2023 one, when Social initiation was $10,000.
It can, but no public sales record prices it. Southpointe Marina slips are separate parcels: the 2026 roll carries 73 slip parcels at the marina with a median 2026 preliminary county just value of $251,497, an appraisal figure, not a sale price. Regatta Landing slips are held by Dock Slip Certificate, and Admirals Watch’s eight slips belong to that condominium. A slip widens the buyer pool; its price comes from its documents and recent slip trades.
Southpointe Marina slips are separate parcels on the county roll, so a separate sale is possible in principle. Who may buy a slip and on what terms is set by the documents of Southpointe at Windstar Marina Association, Inc. (Sunbiz N97000006209), so read them, and the estoppel the marina association issues, before you split the sale. A non-resident slip owner pays the master association 25% of the annual assessment under Bylaw 8.4.
Regatta Landing slips are held by Dock Slip Certificate through Regatta Landing Dock Slip Association, Inc. (Sunbiz N17000010798) and move by the recorded assignment form (Exhibit P, OR 5448 PG 1149). They sit outside the condominium and its assessments. Under the 2013 annexation terms, slips are offered first to Regatta owners, then to other Windstar owners, and to outside buyers only after a year.
The master association’s recorded documents 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. Leases are different: the master association requires 20 days’ notice and a $145 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. Condominium sellers deliver the documents listed in section 718.503, sellers in a homeowners-association village give the section 720.401 disclosure summary before the buyer signs, and every seller gives the property tax disclosure summary. Add your village’s rules and budget, the estoppel certificates and your elevation certificate.
Section 720.401(2) states that the section does not apply to associations under chapters 718, 719, 721 or 723, and Windstar’s nine condominium villages run under chapter 718, while every owner also belongs to the Chapter 720 master association. Whether a summary is owed on your condominium sale is a question for your closing agent or attorney; this is information, not legal advice, and we prepare the documents either way.
Buyers will see it, so explain it. The master assessment went from $3,250 in 2024 to $4,130 in 2025, up $880 or 27.1%, and $780 of that is the new bulk Hotwire internet and TV line (2025 Annual Meeting outline, March 31, 2025). Outside the Hotwire line, the increase was $100 a year, and a buyer comparing communities should count the internet line on both sides.
No special assessment is announced in the master association’s published documents. Its March 2025 deck projects a reserve outlay of about $1.70 million in 2030 for docks, channel, road and marina-entrance dredging, funded under the reserve plan as projected, and a master dock dredge is estimated at about $400,000. Village associations set their own budgets, so any village assessment shows on your village’s estoppel certificate.
The master association’s hurricane and storm reserve held $632,382 at December 31, 2024, after about $127,000 of 2024 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 through 2027. Village and condominium associations carry their own storm costs, and those show in their own budgets.
Only if it has three habitable stories or more. Florida requires a structural integrity reserve study for those buildings at least every 10 years under section 718.112. In Windstar, Windward Cay buildings 4450, 4600 and 4650 Yacht Harbor Drive and Compass Point South’s four buildings appear on the county’s milestone list, next inspection 2033, and Compass Point South has posted its May 29, 2024 study. Most other Windstar condominium buildings are one or two stories.
Most likely Zone AE with a base flood elevation of 8 or 9 feet NAVD88: 58 of 68 Windstar address points queried on October 10, 2026 were AE on panels effective February 8, 2024. Seven of eight Marina Cove points are 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 it 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 Windstar certificates on its elevation certificate layer; the eight modern ones our community guide reads 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 value and are not readily observable, 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, claims and permits. Repairs costing 50% or more of market value count as substantial improvement under 44 CFR 59.1.
It depends on the village. For tax year 2025, most of Windstar paid 12.6162 mills, Regatta Landing 13.6162 mills (including the 1.0000-mill Haldeman Creek MSTU) and Admirals Watch and the Island at Southpointe 9.0514 mills as City of Naples villages. The buyer’s bill is reassessed after the sale, which is why Florida requires the property tax disclosure summary. Windstar has no CDD.
For-sale signs follow your village 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 and Regulations. Because Windstar is gated, visitors are admitted when an owner registers them, so we plan how open house guests and every showing are cleared at the gate.
Yes. We 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. We will tell you plainly what you give up in exposure compared with a full MLS launch. Confidential conversations welcome: call Jesse direct at (239) 898-6072, text or call.
For luxury Windstar sellers we 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, slip rights and the club’s terms.
Yes. Commissions are negotiable and not set by law. Since August 17, 2024, offers of buyer-broker compensation cannot be advertised on the MLS, and buyers sign a written agreement stating their agent’s compensation before touring. A seller may still offer to pay or contribute toward the buyer’s agent off the MLS and may offer buyer concessions on it. We show you the cost of each choice.
That depends on your plans. Leasing 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, and short-term rentals are not allowed. We prepare a net sheet for selling and a lease estimate side by side, so you compare real numbers.
No. We coordinate photography, gate registrations, showings, inspections and the association paperwork for owners who are away, and your closing agent arranges signing logistics. Marc handles the field work, from contractor access to buyer walkthroughs. Tell us your travel dates and we will plan the listing, the showing calendar and the closing around them.
The valuation is free and there is no obligation. We send a written opinion of value with the closings we used, the listings you compete with and a net sheet, and you decide what to do with it. Many owners use it to decide whether to sell this season or wait. Request it from the valuation form or call Jesse.
Call Jesse McGreevy at (239) 898-6072 or request a free valuation. We pull the closings for your village, walk the home, collect the master, village and slip documents, set a price and a plan, and tell you the timeline and net proceeds in writing. Buyers who want to buy in Windstar can call Marc Comisar at (239) 287-5873.
These are the primary sources behind the figures and rules on this page, each 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.
These are the official documents a Windstar on Naples Bay seller is most likely to be asked for, from the master declaration and rules to the slip transfer form and the state’s estoppel and disclosure statutes. Every link goes directly to the publishing association, county or state, not to a summary site.
Document | Publisher | Link |
|---|---|---|
Master declaration, bylaws, articles and amendments (compiled January 24, 2024) | Windstar on Naples Bay Master Association | |
Master Rules and Regulations (May 15, 2018) | Windstar on Naples Bay Master Association | |
Design Guidelines and Tree Policy (May 26, 2022) | Windstar on Naples Bay Master Association | |
2025 Annual Meeting outline (assessment, reserves, debt) | Windstar on Naples Bay Master Association | |
Master lease application | Windstar on Naples Bay Master Association | |
Regatta Landing declaration of condominium | Regatta Landing Condominium Association | |
Regatta Landing dock slip certificate assignment form | Regatta Landing associations | |
Compass Point South Structural Integrity Reserve Study (May 29, 2024) | Compass Point at Windstar Condominium Association | |
Ordinance 93-23, Windstar PUD | Collier County Clerk | |
Florida Statutes section 720.401 (disclosure summary) | Florida Senate | |
Florida Statutes section 718.116 (condominium estoppel certificates) | Florida Legislature | |
Florida Statutes section 720.30851 (HOA estoppel certificates) | Florida Legislature |
Whether you own a Regatta Landing coach home, a Marina Cove condominium, a Somerset villa or a bayfront estate in Windstar on Naples Bay, the next step is a conversation. Talk to McGreevy and Comisar before you list, and get a written price, plan and net sheet with no obligation. To see what your home is worth first, get your free Windstar on Naples Bay home valuation.
If you are thinking, “I need someone to sell my house in Windstar on Naples Bay, Florida,” McGreevy and Comisar helps homeowners price, market, negotiate, and sell with a local strategy built for Naples, Estero, Bonita Springs, Fort Myers, Lee County, Collier County, and Babcock Ranch. Whether you are selling in Regatta Landing, Marina Cove, Spinnaker Pointe, Somerset at Windstar, Yacht Harbour Cove, Windward Cay, Admirals Watch, Harrington Sound, or the Island at Southpointe, our team provides local market guidance, professional listing exposure, and a clear plan to help you sell confidently.
Jesse McGreevy (Sales Associate) and Marc Comisar (Broker Associate) are licensed Florida REALTORS® with Domain Realty; Florida real estate licensure is regulated by the Florida Real Estate Commission (FREC).
McGreevy and Comisar lead Domain Realty Group, a full-service Southwest Florida real estate team. Learn more at DomainRealtyGroup.com.