Winding Bay Preserve
Homes for Sale in Winter Garden, FL
All 693 homes for sale in WINTER GARDEN, FL · median $585,000 · 116 townhomes for sale in WINTER GARDEN · 639 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, Winding Bay Preserve in Winter Garden, FL has 3 homes for sale. Over the 12 months ending 2026-09-20, 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; 5 of 5 report an HOA (median $338/mo); none of the 5 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).
| Location | WINTER GARDEN, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 34 (FL DOR 2025 assessment roll) |
| Years built | 2019–2021 (median 2020.0) |
| Typical living area | 2,200 sq ft (median) |
| Home types (current listings and sales) | townhouses 100% |
| Amenities listed by sellers | Playground, Pool, Clubhouse, Dog Park, Park, Community Mailbox |
| Sale prices, last 12 months | $385,000 median across 3 closed sales · $191 per sq ft |
| Days on market (closed sales) | 166 median |
| For sale right now | 3 active, 0 pending · median asking $425,000 · 7.2 months of supply |
| Owner-occupied (homestead) share | 56% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Winding Bay Preserve key facts,” movewithmomentum.com/neighborhoods/winding-bay-preserve-winter-garden, data as of September 20, 2026.
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 20, 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 October 5, 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 20, 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), 2,147 homes closed in the last 12 months at a median of $598K ($252/sq ft), down 0.8% year over year, with a median 36 days on market. Right now 352 active and 181 pending listings put supply at about 3.7 months - a balanced market. See the live ZIP 34787 housing market and the Orange County market.
County records show 3 qualified sales in Winding Bay Preserve across 2025 - 2025, median $430,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Winding Bay Preserve is a community of 34 homes in Winter Garden, Orange County, built between 2019 and 2021 (median 2020.0), with a median living area of about 2,200 square feet. 56% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
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
Photos 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 20 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.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
27% of homes for sale in ZIP 34787 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-01).
Winding Bay Preserve Market Scorecard
Winding Bay Preserve is currently a buyer-leaning market. About 7.2 months of supply, a median asking price of $425,000, and homes go under contract in about 68 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. 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.
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 and pending Winding Bay Preserve listings as of 2026-10-01, 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.
Every Home for Sale in Winding Bay Preserve Winter Garden Right Now (1)
All 1 active and pending Winding Bay Preserve Winter Garden listings with a detail page, newest first, refreshed twice a day from the MLS.
- 10509 Spring Arbor Lane · $439,000 · 3 bd / 2.5 ba · listed Jul 27, 2026 · listed by Wra Business & Real Estate
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 housing stock is 34 homes built between 2019 and 2021, and 56% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
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.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Winding Bay Preserve 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 (2.8). Basis: Liquidity & Demand 7.2 months of supply; Owner Commitment 56% owner-occupied; Pricing Power 83.9% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $338/month (about $4,056/yr) · median of 150 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 150 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, 2026-10.
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.
See all homes for sale in Winter Garden →
Recently off market in Winding Bay Preserve
Homes in Winding Bay Preserve 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. 2 on record.
- 11102 Hanlon Terrace Alley · off market
- 11156 Hanlon Terrace Alley · off market
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?
How many homes are in Winding Bay Preserve?
What share of Winding Bay Preserve is owner-occupied?
When were the homes in Winding Bay Preserve built?
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?
Where is Winding Bay Preserve, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (1 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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.
Looking to buy here? Search homes for sale →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Winding Bay Preserve fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Winding Bay Preserve
- Home values · What homes in Winding Bay Preserve actually sell for
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Explore more neighborhoods near Winding Bay Preserve with Momentum Realty’s local guides.