Regency Oaks
Homes for Sale in Winter Garden, FL

Regency Oaks is an established, larger-home enclave in Winter Garden's Orange County footprint, built out over a five-year stretch in the mid-2000s and now settled into low-turnover ownership.

Stellar MLS sales records identify 102 homes in Regency Oaks that have changed hands since 2005, built between 2003 and 2005 (median 2005), with a median living area of about 2,114 sq ft and a typical 4-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.

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.

Regency Oaks 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 Regency Oaks specifically. Momentum Research analysis of MLS records.

With 216 homes built in a tight 2003–2008 band, this is a cohesive community rather than a patchwork of eras. The median living space near 2,483 square feet points to two-story homes with room to spread out, and because everything is roughly the same vintage, buyers are effectively comparing maintenance histories more than architecture. A home with a newer roof and updated systems will read very differently on price than a comparable floor plan that has deferred those items.

The 68% homestead share signals a neighborhood held largely by long-term owners, which historically keeps inventory tight. That works two ways: sellers face little direct competition when they do list, but buyers should be prepared to move decisively when a well-kept home appears, since options at any given moment are limited.

In a low-turnover community with few active listings, pricing lives or dies on condition-adjusted comparisons, not headline averages. We track the mid-2000s systems questions that actually move value here — roof, HVAC, kitchen age — and we help sellers position honestly and buyers underwrite the work a given home still needs.

Listings in this community report association dues of about $99 per month ($1,188 a year) — the median AssociationFee across 9 MLS records, normalised to a monthly figure; most are billed monthly. 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.