Westside Village
Homes for Sale in Windermere, FL

Westside Village market snapshot (as of September 12, 2026): the median sale price is about $665K ($240 per sq ft over the trailing 12 months of closed sales), a median 53 days on market for closed sales, and 3.7 months of supply, a balanced market. The trailing-12-month median is down 1% from the prior 12 months, computed from record-level Stellar MLS closed sales (12 closings in the current window).

In ZIP 34786 (WINDERMERE), 784 homes closed in the last 12 months at a median of $622K ($262/sq ft), down 1.5% year over year, with a median 38 days on market. Right now 113 active and 37 pending listings put supply at about 3.0 months - a balanced market. See the live ZIP 34786 housing market and the Orange County market.

Flood zones in Westside Village: of 15 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Windermere.

Westside Village is a community of 127 homes in Windermere, Orange County, built between 2008 and 2018 (median 2018.0), with a median living area of about 2,677 square feet. 32% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

• Bay Lake Elementary · Elementary
• Horizon West Middle School · Middle
• Windermere High School · High

Zoned schools reflect the assignments reported on recent Westside Village listings and can change; always confirm with Orange County Public Schools for a specific address.

Buying with schools in mind? We can confirm the exact zoned schools for any Westside Village address.

At a median of $240 per square foot, Westside Village prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.

Inventory runs at 3.7 months of supply, a balanced market and the trailing-12-month median down 1% year over year. Homes that do trade take a median 53 days on market, useful leverage on any listing that has lingered.

The housing stock is 127 homes built between 2008 and 2018, and 32% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.

Listings in this community report association dues of about $122 per month ($1,464 a year) - the median AssociationFee across 51 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.