Oakglen Estates
Homes for Sale in Winter Garden, FL

Oakglen Estates is a mid-2000s enclave of 62 homes in Winter Garden's Orange County footprint, where the roughly 2,337-square-foot median home and consistent build era make condition the real differentiator between one listing and the next.

Stellar MLS sales records identify 43 homes in Oakglen Estates that have changed hands since 2006, built between 2005 and 2007 (median 2006), with a median living area of about 2,337 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.

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.

Oakglen Estates 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 Oakglen Estates specifically. Momentum Research analysis of MLS records.

• Dillard Street Elem · Elementary
• Lakeview Middle · Middle
• Ocoee High · High

Zoned schools reflect the assignments reported on recent Oakglen Estates 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 Oakglen Estates address.

Everything here was built within a three-year span, so you are looking at a single architectural generation rather than a mix of eras. Homes now roughly two decades old are at the age where major systems — roofs, HVAC, water heaters — either have been replaced already or are due. That is the first thing to check on any Oakglen listing, and it is where value gaps open up between otherwise similar homes.

With about three-quarters of homes homesteaded, this reads as a stable, owner-occupied community that does not churn quickly. That stability tends to keep the stock maintained, but it also means listings are limited. Expect to evaluate homes one at a time as they come available rather than comparing a deep bench of options.

In a 62-home community with limited turnover, the difference between a fair price and an overpay comes down to condition and updates, not headline square footage. We track what actually closes here, help you weight the cost of pending system replacements against a home's asking price, and tell you plainly when a listing is priced for its finishes rather than its bones.

Listings in this community report association dues of about $64 per month ($768 a year) — the median AssociationFee across 4 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, 2026-09.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.