Westside Townhomes
Homes for Sale in Winter Garden, FL

A 90-home townhome enclave in Orange County's Winter Garden, built mostly in the early 2000s with a median build year of 2004 and a compact median footprint near 1,216 square feet. The under-half homestead share signals a meaningful investor and rental presence, which shapes both pricing and community feel.

Stellar MLS sales records identify 204 homes in Westside Townhomes that have changed hands since 2004, built between 1986 and 2005 (median 1990), with a median living area of about 984 sq ft and a typical 3-bedroom, 2-bath layout; 97% are townhomes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

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.

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

In ZIP 34787, 957 homes are on the market and 30% are under contract — a steady corner of Winter Garden.

Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).

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.

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

The build window runs from 1988 to 2005, but the median year built of 2004 tells you the bulk of these townhomes are from the later end of that range. That matters: older units may carry deferred roof, HVAC, and system questions, while the newer wave is closer to move-in condition. In a footprint this compact, the difference between updated and dated interiors is often what separates one price from another.

With homestead status on roughly a third of homes, this community carries a notable share of non-owner-occupied units. That can mean more rental turnover and a broader mix of interior conditions on the market at any given time. Buyers should read the HOA documents carefully for rental rules and reserves; sellers should know they are often competing against investor inventory.

In a community this thin on recent closings, a broker who reads condition and HOA fine print is worth more than a pricing algorithm. We walk the units, weigh the update level against the older systems common in the 1988-to-2005 range, and price against what is actually moving rather than a guessed number. That keeps sellers realistic and buyers from overpaying for cosmetics.

Listings in this community report association dues of about $61 per month ($732 a year) — the median AssociationFee across 3 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.