Oak Park At Winter Garden
Homes for Sale in Winter Garden, FL

A compact, single-era community in Winter Garden where nearly three-quarters of homes (74.4%) are owner-occupied under homestead exemption, pointing to a market with limited turnover and a base of long-tenured owners rather than frequent resale churn.

Stellar MLS sales records identify 20 homes in Oak Park At Winter Garden that have changed hands since 2005, built between 1997 and 1999 (median 1998), with a median living area of about 1,602 sq ft and a typical 3-bedroom, 2-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 3 qualified sales in Oak Park At Winter Garden across 2024–2025 (1 in 2024, 2 in 2025), median $482,500 — 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.

Oak Park At Winter Garden is too small for its own price trend, so here is the market around it.

In ZIP 34787, 932 homes are on the market and 29% are under contract — a steady corner of Winter Garden.

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

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.

ZIP and county figures describe the wider market, not Oak Park At Winter Garden specifically. Momentum Research analysis of MLS records.

With only 43 homes in the community and a homestead share of 74.4%, inventory here is inherently thin — this is not a subdivision where dozens of comparable listings hit the market at once. Buyers should expect to move decisively when something in their range and condition preference appears, since the recent median of 6 days on market suggests limited time to deliberate once a listing goes active.

Current MLS data does not identify specific community amenities, so any recreational features, common areas, or HOA-maintained facilities should be confirmed directly rather than assumed. Pricing should be evaluated on a per-home basis: with homes built within a tight 1997-1999 window, the spread in value is more likely driven by renovation level, lot specifics, and finish quality than by structural age differences.

In a community this small, with only 43 homes and a fast median timeline of 6 days, missing a listing by a day can mean missing it entirely. We track this pocket closely enough to flag new listings and shifts in condition-driven pricing before they become common knowledge, and we help you verify amenity and HOA details directly rather than relying on assumptions.

Listings in this community report association dues of about $24 per month ($288 a year) — the median AssociationFee across 78 MLS records, normalised to a monthly figure; most are billed twice a year. 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.