Windward Cay
Homes for Sale in Winter Garden, FL

Windward Cay market snapshot (as of September 20, 2026): the median sale price is about $775K ($232 per sq ft over the trailing 12 months of closed sales), and a median 5 days on market for closed sales.

In ZIP 34787 (Winter Garden), 2,123 homes closed in the last 12 months at a median of $595K ($252/sq ft), down 0.9% year over year, with a median 37 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 Windward Cay across 2024 - 2024, median $875,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Windward Cay is a community of 66 homes in Winter Garden, Orange County, built between 2002 and 2004 (median 2003.0), with a median living area of about 3,137 square feet. 92% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

A gated, deed-restricted enclave of 66 homes built in the early 2000s, Windward Cay trades on large living space and low turnover rather than volume - with no active listings at this snapshot, buyers are working from very limited, recent closing data rather than a live inventory to compare.

The homes in Windward Cay were built within a two-year span (2002 - 2004), which gives the community a consistent architectural era and lot pattern rather than the mixed vintages you see in communities built out over a decade or more. Median living area of 3,137 square feet points to larger, multi-bedroom floor plans, and the $232.28 median price per square foot suggests value here is driven primarily by size and condition rather than by a wide spread of product types.

A homestead share of 92.4% is notable - the large majority of homes in this community carry a homestead exemption, which generally indicates owner-occupied use rather than a market with heavy investor or short-term-rental turnover. Combined with zero current active listings, this is a community where inventory simply does not sit on the market waiting for buyers - it's worth setting up a listing alert and being ready to move quickly when something appears.

With no active listings and only a handful of recent closings to reference, pricing a home in Windward Cay accurately takes more than pulling a generic comp sheet - it takes someone tracking this specific 66-home community closely enough to know what the last few sales actually looked like inside. We help sellers price against that thin, real data instead of guesswork, and help buyers move fast and correctly the moment something comes available.

Listings in this community report association dues of about $115 per month ($1,380 a year) - the median AssociationFee across 103 MLS records, normalised to a monthly figure; most are billed quarterly. 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.