Windermere Downs
Homes for Sale in Windermere, FL

Windermere Downs 1St Add is a small, established pocket of about 80 homes in Windermere, Orange County, where a wide age range means the real variable is how much a given home has been updated. A homestead share near 88% points to an owner-occupied, low-turnover street rather than an investor-driven one.

Stellar MLS sales records identify 121 homes in Windermere Downs that have changed hands since 2010, built between 1973 and 2015 (median 1986), with a median living area of about 2,971 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.

County records show 8 qualified sales in Windermere Downs across 2024–2025 (4 in 2024, 4 in 2025), median $835,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Windermere Downs is too small for its own price trend, so here is the market around it.

In ZIP 34786, 282 homes are on the market and 26% are under contract — a steady corner of Windermere.

Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).

In ZIP 34786 (Windermere), 788 homes closed in the last 12 months at a median of $640K ($261/sq ft), down 0.6% year over year, with a median 40 days on market. Right now 131 active and 43 pending listings put supply at about 3.7 months — a balanced market. See the live ZIP 34786 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Windermere Downs specifically. Momentum Research analysis of MLS records.

The story of this community is the gap between its oldest and newest homes. With construction dates running from 1973 through 2023 and the midpoint at 1988, no two sales are truly comparable on paper. A 1970s-era home in original condition and a recent rebuild can share a street and command very different numbers, which is why the $825,000 median tells you the center of gravity but not much about any one house.

At roughly 2,731 median living square feet and about $278 per square foot, homes here are substantial rather than compact. Buyers should underwrite each property on its own renovation level, systems age, and lot. Sellers should recognize that presentation and documented updates are what separate the fast, strong sales from the ones that sit.

A community this small with this much age variation rewards local reading over broad averages. We help sellers position a home against the right comps given its condition, and we help buyers move with speed and discipline when a 7-day median leaves little margin for hesitation.

Listings in this community report association dues of about $83 per month ($996 a year) — the median AssociationFee across 61 MLS records, normalised to a monthly figure; most are billed annually. 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.