Windward Cay
Homes for Sale in Winter Garden, FL

Windward Cay market snapshot (as of September 12, 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), 2,162 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 47 homes in Windward Cay that have changed hands since 2006, built between 2002 and 2004 (median 2003), with a median living area of about 3,140 sq ft and a typical 4-bedroom, 3-bath layout; 100% 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.

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 9 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, 2026-09.

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