Eastbrook
Homes for Sale in Winter Park, FL

Eastbrook is a compact, mid-century Winter Park community of 152 homes built almost entirely between 1954 and 1965, with a typical home running about 1,343 square feet — a scale and era that favors buyers looking for an established footprint over new construction.

Stellar MLS sales records identify 435 homes in Eastbrook that have changed hands since 2004, built between 1954 and 2018 (median 1964), with a median living area of about 1,471 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 Eastbrook across 2024–2025 (2 in 2024, 1 in 2025), median $365,000 — 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.

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

In ZIP 32792, 151 homes are on the market and 19% are under contract — a steady corner of Winter Park.

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

In ZIP 32792 (Winter Park), 617 homes closed in the last 12 months at a median of $408K ($256/sq ft), down 1.9% year over year, with a median 28 days on market. Right now 49 active and 13 pending listings put supply at about 3.4 months — a balanced market. See the live ZIP 32792 housing market and the Orange County market.

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

There's no meaningful spread in construction era here — every home in Eastbrook was built within an 11-year window, with a median year built of 1959. That narrows what actually separates one listing from the next. Original systems versus updated ones, additions versus original footprint, and how a kitchen or bath has aged all carry more weight than they would in a neighborhood with a mix of decades and builders.

Current MLS data doesn't surface any shared community amenities for Eastbrook — no clubhouse, pool, or organized recreational facility tied to the listings. That points to a neighborhood where the appeal is the location and the housing stock itself, not a bundled amenity package, and it's worth factoring into how you weigh this community against nearby options that do carry HOA-run facilities.

In a community this tightly clustered by build year, generic comps don't cut it — we look at what's actually been updated inside each of Eastbrook's 152 homes, not just when the house was built, so pricing and offers reflect real condition rather than a neighborhood average.

Listings in this community report association dues of about $2 per month — the median AssociationFee across 11 MLS records, normalised to a monthly figure; most are billed annually. 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.