Windswept Estates
Homes for Sale in Freeport, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Emerald Coast MLS
As of November 2026, Windswept Estates in Freeport, FL has 21 homes for sale and 4 pending, asking from $485,000 to $759,500 (median $545,000). Over the 12 months ending 2026-11-09, 8 recorded sales closed at a median of $579,750, a median 28 days on market, sellers accepting 99% of original asking. Homes listed or recently sold were built 2005–2026 with 9 new construction; 37 of 37 report an HOA (median $116/mo); none of the 35 geocoded homes sit in a FEMA special flood hazard zone (median elevation 98 ft). At the median price and Walton County's FY2025-26 rate of 9.758 mills, annual property tax runs about $5,660 ($5,270 with the full homestead exemption).
| Location | Freeport, Walton County, FL · ZIP 32439 |
|---|---|
| Homes in the community | 289 (FL DOR 2025 assessment roll) |
| Years built | 2004–2024 (median 2020.0) |
| Typical living area | 3,158 sq ft (median) |
| Home types (current listings and sales) | detached single family 100% |
| Amenities listed by sellers | Gated, Playground, Pool, Tennis Court(s), Golf, Pets Allowed |
| Sale prices, last 12 months | $579,750 median across 8 closed sales |
| Days on market (closed sales) | 28 median |
| For sale right now | 21 active, 4 pending · median asking $545,000 · 21.0 months of supply |
| Owner-occupied (homestead) share | 71% |
Data as of November 9, 2026. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Windswept Estates key facts,” movewithmomentum.com/neighborhoods/windswept-estates, data as of November 9, 2026.
Last 30 days in Windswept Estates: 1 new listing (median asking $599,000), 4 under contract right now, 2 closed sales (median $750,000). As of November 9, 2026, Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate.
Homes For Sale Right Now in Windswept Estates
Live MLS inventory for Windswept Estates. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 91 daysTop listing
Active · 83 days
Active · 140 days
Active · 507 days
Active · 83 daysActive · 18 days
Active · 66 days
Active · 334 days
Active · 102 days
Active · 111 days
Active · 38 days
Active · 74 days
Active · 102 days
Active · 145 daysActive and pending Windswept Estates listings as of 2026-11-09, priced high to low. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate. Tap any home to ask about it.
Every Home for Sale in Windswept Estates Right Now (23)
All 23 active and pending Windswept Estates listings with a detail page, newest first, refreshed twice a day from the MLS.
- 331 Brushed Dunes Circle · $545,000 · 4 bd / 2.5 ba · listed Oct 2, 2026 · listed by Real Broker LLC
- 59 S Bentgrass Road · $734,900 · 4 bd / 3 ba · pending · listed Sep 11, 2026 · listed by Coldwell Banker Realty
- 503 Tournament Lane · $565,000 · 4 bd / 3 ba · listed Sep 4, 2026 · listed by Real Broker LLC
- 94 S Bentgrass Road · $545,000 · 3 bd / 3 ba · listed Aug 27, 2026 · listed by Real Broker LLC
- 881 Brushed Dune Circle · $565,000 · 4 bd / 3 ba · pending · listed Aug 27, 2026 · listed by Real Broker LLC
- 559 Coastal Breeze Drive · $599,000 · 4 bd / 3.5 ba · listed Aug 21, 2026 · listed by Scenic Sotheby's International Realty
- 492 E Club House Drive · $624,900 · 4 bd / 3 ba · listed Aug 18, 2026 · listed by Coldwell Banker Realty
- 190 Tournament Lane · $735,000 · 4 bd / 3 ba · listed Aug 18, 2026 · listed by Coldwell Banker Realty
- 64 Hollow Log Lane · $515,000 · 3 bd / 3 ba · listed Aug 11, 2026 · listed by RE/MAX by the Sea
- 440 Gentle Wind Court · $546,500 · 3 bd / 2 ba · listed Aug 11, 2026 · listed by Real Broker LLC
- 909 Brushed Dunes Circle · $529,000 · 4 bd / 3 ba · listed Aug 11, 2026 · listed by Berkshire Hathaway HomeServices
- 259 Fairway Crossing · $639,000 · 4 bd / 3 ba · listed Aug 11, 2026 · listed by Cohron Realty Group LLC
- 235 Coastal Breeze Drive · $530,000 · 5 bd / 3 ba · listed Aug 11, 2026 · listed by Pearce Realty Group LLC
- 480 Windswept Boulevard · $485,000 · 4 bd / 2 ba · listed Aug 11, 2026 · listed by Own It Real Estate LLC
- 51 Tournament Lane · $510,000 · 3 bd / 2 ba · listed Aug 11, 2026 · listed by Berkshire Hathaway HomeServices
- 32 Brushed Dune Circle · $558,900 · 4 bd / 3 ba · listed Aug 11, 2026 · listed by EXP Realty LLC
- 155 E Club House Drive · $625,000 · 3 bd / 2 ba · listed Aug 11, 2026 · listed by South Walton Realty Sales LLC
- 961 N Coastal Breeze Drive · $507,990 · 3 bd / 3 ba · listed Aug 11, 2026 · listed by Holiday Builders
- 923 Coastal Breeze Drive · $507,990 · 3 bd / 3 ba · listed Aug 11, 2026 · listed by Holiday Builders
- 132 N Bentgrass Road · $543,790 · 4 bd / 3 ba · listed Aug 11, 2026 · listed by Holiday Builders
- 120 N Bentgrass Road · $558,590 · 4 bd / 3 ba · listed Aug 11, 2026 · listed by Holiday Builders
- 34 S Bentgrass Road · $502,864 · 4 bd / 2 ba · listed Aug 11, 2026 · listed by Holiday Builders
- 69 Fairway Crossing · $699,999 · 4 bd / 3 ba · pending · listed Aug 11, 2026 · listed by HomeBiz Properties
Price here is driven by the homes themselves, not by shared amenities. Windswept Estates leans toward larger, newer construction — a median build around 2020 and a median footprint just over 3,150 square feet — and that size and condition is what supports a median near $532,240. There is no amenity package pulling weight, so what you pay for is square footage and finish level.
The posture right now favors buyers. Prices are off 8.8% year over year, the typical listing sits about 71 days before going under contract, and the market heat score of 25 says nothing is moving in a hurry. With 15 active listings against a modest closing pace, sellers should expect to compete on condition and price rather than count on urgency. Buyers have room to be selective and to negotiate.
Figures in this note are as of July 25, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Windswept Estates right now
🟢 Buyer-leaning market. 21.0 months of supply and 16% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Emerald Coast MLS records, as of November 9, 2026. Confidence: Very High (25 active and pending listings, 8 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 9, 2026 · Live data: Emerald Coast MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Windswept Estates market snapshot (as of November 9, 2026): the median sale price is about $580K, a median 29 days on market for closed sales, and 21.0 months of supply, a buyer-leaning market.
Windswept Estates is a community of 289 homes in Freeport, Walton County, built between 2004 and 2024 (median 2020.0), with a median living area of about 3,158 square feet. 71% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Windswept Estates is a larger community of 355 homes in Freeport with no identified shared amenities, so value tracks the house, not the neighborhood package. The high homestead share of roughly 72% points to a stable, owner-occupied core rather than an investor-heavy street.
The setting & the homes.
Aerial and on-site photos of Windswept Estates. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Windswept EstatesPhotos from Emerald Coast MLS listings in Windswept Estates; content deemed reliable but not guaranteed.
Who Windswept Estates is best for.
Best for
- Buyers wanting substantial square footage in newer construction around the mid-$500s median
- Owner-occupants planning to stay long enough to ride out a soft patch
- Patient buyers who want negotiating leverage and time to compare listings
Probably not for
- Buyers who need pool, clubhouse, or other shared amenities on site
- Sellers who need a fast exit and cannot wait out a roughly 71-day market
- Short-term flippers counting on quick appreciation in a declining-price window
Housing distress & ownership in WINDSWEPT ESTATES, Freeport
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Listing data provided by the Emerald Coast Association of REALTORS®. Information is deemed reliable but is not guaranteed by the MLS to be accurate. Deemed reliable but not guaranteed.
Windswept Estates on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Emerald Coast MLS. Map data © OpenStreetMap contributors.
Schools
- Walton County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Freeport · Elementary
- Freeport · Middle
- Freeport · High
Zoned schools reflect the assignments reported on recent Windswept Estates listings and can change; always confirm with Walton County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Windswept Estates address.
The Windswept Estates buying strategy.
If we were buying in Windswept Estates today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Windswept Estates.
A size-driven market, softening
The homes span build years from 2004 to 2024, with the median around 2020, so most of the inventory here is relatively recent construction. At a median of roughly 3,150 square feet, these are substantial houses, and that scale is the core of the value story. Because pricing is condition- and size-driven, expect a wide spread between listings — updated, larger homes will ask more, and the median is your anchor, not a ceiling or a floor.
The current data shows a cooling market: negative year-over-year movement, a 71-day median time on market, and a low heat score. That combination gives buyers leverage and patience, and it tells sellers to price against recent closings honestly. This is not a market where a stale, over-asked listing gets rescued by momentum.
The location and the amenities are priced into every listing in Windswept Estates. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Windswept Estates buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (5.6). Basis: Liquidity & Demand 21.0 months of supply; Owner Commitment 71% owner-occupied; Pricing Power 99.4% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a softening, condition-driven market like this, the difference between a strong and a weak outcome is pricing and preparation. We read the recent closings against the specific home — its build year, size, and finish level — instead of leaning on a neighborhood-wide average. For buyers, that means knowing where the negotiating room actually is; for sellers, it means positioning against a 71-day norm rather than fighting it.
Windswept Estates in 15 seconds.
Tools for a Windswept Estates buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Windswept Estates sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windswept Estates, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windswept Estates home worth?
Get a no-obligation home value based on real comparable sales in Windswept Estates, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Freeport →
Recently off market in WINDSWEPT ESTATES
Homes in WINDSWEPT ESTATES that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 8 on record.
- 1003 Coastal Breeze Drive · off market
- 132 Gulf Pines Court · off market
- 139 Coastal Breeze Drive · off market
- 307 Coastal Breeze Drive · off market
- 334 Tournament Lane · off market
- 437 Gentle Wind Court · off market
- 513 W Club House Drive · off market
- 810 Brushed Dune Circle · off market
Recently sold in Windswept Estates
- 307 Coastal Breeze Drive · sold $735,000
- 513 W Club House Drive · sold $765,000
- 139 Coastal Breeze Drive · sold $470,000
- 1003 Coastal Breeze Drive · sold $537,500
- 132 Gulf Pines Court · sold $622,000
- 810 Brushed Dune Circle · sold $626,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
Frequently Asked Questions
What is the median home price in Windswept Estates?
How long do homes in Windswept Estates take to sell?
Is Windswept Estates a buyer's or seller's market right now?
How many homes are in Windswept Estates?
What share of Windswept Estates is owner-occupied?
When were the homes in Windswept Estates built?
Who is the best real estate agent for Windswept Estates?
How do I find a top Freeport real estate agent who knows Windswept Estates?
Can Momentum Realty connect me with an agent for Windswept Estates?
Should you buy in Windswept Estates?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Windswept Estates with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Emerald Coast MLS, refreshed twice daily (last: November 9, 2026) |
| Community market stats | Emerald Coast MLS closed sales, 12-month windows ending November 9, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (8 streets, ZIP 32439)) |
| Under-contract shares | Emerald Coast MLS records, as of 2026-11-09 |
| Historical depth | Closed-sale records back to 2026 (8 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Emerald Coast MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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See how WINDSWEPT ESTATES fits the bigger picture — live prices, inventory, and Momentum Scores: