Winding Bay
Homes for Sale in Winter Garden, FL
All 693 homes for sale in Winter Garden, FL · median $585,000 · 639 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-09-20, 19 recorded sales closed at a median of $785,000, $249 per square foot, a median 20 days on market, sellers accepting 97% of original asking (+1% versus the prior year). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $13,090 ($12,420 with the full homestead exemption).
| Location | Winter Garden, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 283 (FL DOR 2025 assessment roll) |
| Years built | 2019–2024 (median 2021) |
| Typical living area | 2,835 sq ft (median) |
| Sale prices, last 12 months | $785,000 median across 19 closed sales · $249 per sq ft · +1.0% vs the prior 12 months |
| Days on market (closed sales) | 20 median |
| Owner-occupied (homestead) share | 69% |
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 Ph 3 key facts,” movewithmomentum.com/neighborhoods/winding-bay-ph-3, data as of September 20, 2026.
Winding Bay Ph 3 sits in the mid-$700s at a median of $725,000, with a median around $238 per square foot. That combination tells you price here is driven more by home size, finish, and lot than by any single entry point — the per-foot figure is moderate, so a larger floor plan does more to move a number than premium finishes alone.
At a median of 55 days on market, this is not a snap-your-fingers market. Homes are taking the better part of two months to trade, which gives a buyer room to inspect, negotiate, and walk if the terms are wrong. For a seller, it means pricing to the current comps and presenting the home well matters more than hoping momentum carries a stretch number.
Winding Bay right now
🟡 Still climbing. The trailing-12-month median ($785K) is up 1.0% from the prior 12 months ($778K). With about 19 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Medium (19 and 6 sales in the two windows).
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
Nearby homes for sale
No active listings inside Winding BayHomes for Sale in Winter Garden, FL right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Winding Bay market snapshot (as of September 20, 2026): the median sale price is about $785K ($249 per sq ft over the trailing 12 months of closed sales), and a median 20 days on market for closed sales. The trailing-12-month median is up 1% from the prior 12 months, computed from record-level Stellar MLS closed sales (19 closings in the current window).
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 32 qualified sales in Winding Bay across 2024–2025 (25 in 2024, 7 in 2025), median $652,800 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Winding Bay is a community of 283 homes in Winter Garden, Orange County, built between 2019 and 2024 (median 2021), with a median living area of about 2,835 square feet. 69% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a Winter Garden community in west Orange County where pricing is condition- and size-driven rather than clustered around a single tier, and where a two-month absorption pace rewards patience on both sides of the table.
Who Winding Bay is best for.
Best for
- Buyers with a mid-$700s budget who want a larger floor plan and a west Orange County location
- Buyers who value time to inspect and negotiate over speed
- Sellers willing to price to current comps and present the home well
Probably not for
- Buyers who need to be under contract in a matter of days
- Sellers expecting to name an above-market number and have it clear quickly
- Buyers working a budget well below the mid-$700s median here
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 ($785K) IS the median in the snapshot above, and the move from 2025 ($778K) IS the +1.0% one-year change.
Windows contain 5 to 39 sales each (19 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.
29% 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 (2026-09-20).
Housing distress & ownership in Winding Bay Ph 3, 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.
The Winding Bay buying strategy.
If we were buying in Winding Bay 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.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
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.
Reading the pace and the price
The closing window here is thin — the snapshot rests on a small number of recent sales — so treat the median as a directional read, not a precise ceiling or floor. When only a handful of homes trade in a window, one large or heavily upgraded sale can nudge the median more than the broader trend warrants. That is a reason to work each listing on its own comps rather than lean on the community average.
The 55-day median is the more durable signal. It says demand is real but measured, and that a well-prepared, correctly-priced home should transact without extraordinary concessions. It also means an overpriced listing will sit and eventually correct — so the discipline is in the initial number, not in chasing the market down later.
The location and the amenities are priced into every listing in Winding Bay. 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 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 (7.1). Basis: Recent Direction +1.0% year-over-year; Owner Commitment 69% owner-occupied; Pricing Power 97.4% sale-to-list. Refreshed with each data update.
Why work with Momentum here
With a thin recent-sales window and a per-foot number that swings on floor plan and finish, the value is in getting the comps right and reading the individual home — not in leaning on a headline median. We price and negotiate off what is actually trading in this pocket of Winter Garden, and we will tell you plainly when a listing is a stretch or when it is worth pressing on days-on-market to win a concession.
Winding Bay in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
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 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 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, 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 home worth?
Get a no-obligation home value based on real comparable sales in Winding Bay, 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?
How long do homes in Winding Bay take to sell?
How many homes are in Winding Bay?
What share of Winding Bay is owner-occupied?
When were the homes in Winding Bay built?
Who is the best real estate agent for Winding Bay?
How do I find a top Winter Garden real estate agent who knows Winding Bay?
Can Momentum Realty connect me with an agent for Winding Bay?
Where is Winding Bay, and what county is it in?
Is Winding Bay a good place to live?
Should you buy in Winding Bay?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2021 (113 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 Ph 3 fits the bigger picture — live prices, inventory, and Momentum Scores:
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