Overstreet Crate
Homes for Sale in Winter Garden, FL

A small, established pocket of Winter Garden - 340 homes total - where build years run from 1909 to 2024 and the typical home sits at 1,367 square feet. Just over half of homes here carry homestead status, consistent with an area built out gradually rather than in a single development cycle.

Stellar MLS sales records identify 22 homes in Overstreet Crate that have changed hands since 2015, built between 1924 and 2026 (median 1958), with a median living area of about 1,160 sq ft and a typical 3-bedroom, 2-bath layout; 95% 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.

Overstreet Crate 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 Overstreet Crate specifically. Momentum Research analysis of MLS records.

• William Frangus Elem · Elementary
• Lakeview Middle · Middle
• West Orange High · High

Zoned schools reflect the assignments reported on recent Overstreet Crate 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 Overstreet Crate address.

With 2 active listings and 12 months of supply, Overstreet Crate does not behave like a typical subdivision market. There simply is not enough current inventory to establish a clear trend line - every listing that does come up carries outsized weight in shaping perception of value for the area.

The age range of the housing stock, 1909 through 2024, is the other defining variable. A community built out over more than a century means lot size, layout, and system age vary far more than in a single-phase build. Buyers should expect to evaluate each home on its own condition and recent updates rather than assuming consistency across the area.

In a market this thin - 2 active listings against a full year of supply - pricing a home or making an offer requires reading condition and recent comparable activity carefully rather than leaning on volume trends that do not exist yet. We track the Overstreet Crate listings as they surface and help buyers and sellers price against the realistic pool of comparable homes rather than assumptions built for larger, more active subdivisions.

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