Winding Bay
Homes for Sale in Winter Garden, FL

Winding Bay market snapshot (as of September 12, 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), 2,162 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 139 homes in Winding Bay that have changed hands since 2020, built between 2019 and 2025 (median 2021), with a median living area of about 2,613 sq ft and a typical 4-bedroom, 3.5-bath layout; 86% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

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.

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.

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.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.