Winding Bay Preserve
Homes for Sale in Winter Garden, FL
All 720 homes for sale in WINTER GARDEN, FL · median $575,000 · 106 townhomes for sale in WINTER GARDEN · 509 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, Winding Bay Preserve in Winter Garden, FL has 3 homes for sale. Over the 12 months ending 2026-09-12, 3 recorded sales closed at a median of $385,000, $191 per square foot, a median 166 days on market, sellers accepting 84% of original asking. Homes listed or recently sold were built 2019 - 2021; 8 of 8 report an HOA (median $338/mo); none of the 7 geocoded homes sit in a FEMA special flood hazard zone (median elevation 115 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $6,420 ($5,750 with the full homestead exemption).
Homes For Sale Right Now in Winding Bay Preserve
Live MLS inventory for Winding Bay Preserve. 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 · 1 daysTop listing
Active · 52 days
Active · 7 daysActive and pending Winding Bay Preserve listings as of 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Tap any home to ask about it.
Winding Bay Preserve right now
🟢 Buyer-leaning market. 7.2 months of supply and 0% 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 Stellar MLS records, as of September 12, 2026. Confidence: Medium (3 active and pending listings, 3 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Winding Bay Preserve market snapshot (as of September 12, 2026): the median sale price is about $385K ($191 per sq ft over the trailing 12 months of closed sales), a median 166 days on market for closed sales, and 7.2 months of supply, a buyer-leaning market.
In ZIP 34787 (WINTER GARDEN), 2,162 homes closed in the last 12 months at a median of $595K ($251/sq ft), down 0.6% year over year, with a median 36 days on market. Right now 357 active and 169 pending listings put supply at about 3.8 months - a balanced market. See the live ZIP 34787 housing market and the Orange County market.
Stellar MLS sales records identify 32 homes in Winding Bay Preserve that have changed hands since 2020, built between 2019 and 2021 (median 2020), with a median living area of about 2,037 sq ft and a typical 4-bedroom, 3-bath layout; 94% are townhomes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
The setting & the homes.
Aerial and on-site photos of Winding Bay Preserve. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Winding Bay PreservePhotos from Stellar MLS listings in Winding Bay Preserve; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($385K) IS the median in the snapshot above.
Windows contain 0 to 7 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Deemed reliable but not guaranteed.
WINDING BAY PRESERVE Market Scorecard
WINDING BAY PRESERVE is currently a buyer's market. About 7.2 months of supply, a median asking price of $439,000, and homes go under contract in about 7 days.
Typical home value in the 34787 ZIP is $574,696, right around the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Winding Bay Preserve, WINTER GARDEN
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. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
Winding Bay Preserve on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at Winding Bay Preserve
- Playground · reported on 4 of 4 listings
- Park · reported on 3 of 4 listings
- Pool · reported on 3 of 4 listings
- Clubhouse · reported on 2 of 4 listings
- Dog Park · reported on 2 of 4 listings
- Community Mailbox · reported on 1 of 4 listings
- Fitness Center · reported on 1 of 4 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Orange County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Water Spring Elementary · Elementary
- Water Spring Middle · Middle
- Horizon High School · High
Zoned schools reflect the assignments reported on recent Winding Bay Preserve listings and can change; always confirm with Orange County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Winding Bay Preserve address.
Shop the zone: Homes zoned for Horizon High School
The Winding Bay Preserve buying strategy.
If we were buying in Winding Bay Preserve 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 Winding Bay Preserve.
A closer look at the Winding Bay Preserve market
At a median of $191 per square foot, Winding Bay Preserve prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 7.2 months of supply, a buyer-leaning market. Homes that do trade take a median 166 days on market, useful leverage on any listing that has lingered.
The location and the amenities are priced into every listing in Winding Bay Preserve. The deal is won or lost on condition, the comps, and the renovation math.
HOA, CDD & Fees
- HOA dues reported around $338/month (about $4,056/yr) · median of 24 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $338 per month ($4,056 a year) - the median AssociationFee across 24 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Winding Bay Preserve 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 Winding Bay Preserve sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winding Bay Preserve, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winding Bay Preserve home worth?
Get a no-obligation home value based on real comparable sales in Winding Bay Preserve, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Winding Bay Preserve?
How long do homes in Winding Bay Preserve take to sell?
Is Winding Bay Preserve a buyer's or seller's market right now?
Who is the best real estate agent for Winding Bay Preserve?
How do I find a top Winter Garden real estate agent who knows Winding Bay Preserve?
Can Momentum Realty connect me with an agent for Winding Bay Preserve?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2021 (20 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 Stellar 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.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how Winding Bay Preserve fits the bigger picture — live prices, inventory, and Momentum Scores:
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