Olympia Heights Annex
Homes for Sale in Winter Park, FL

Olympia Heights Annex is a small, older Winter Park enclave of 127 homes with a century-wide build range, which means the housing stock varies lot by lot rather than reading as one uniform product.

Stellar MLS sales records identify 19 homes in Olympia Heights Annex that have changed hands since 2005, built between 1935 and 2006 (median 1955), with a median living area of about 1,100 sq ft and a typical 3-bedroom, 1-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 9 qualified sales in Olympia Heights Annex across 2024–2025 (4 in 2024, 5 in 2025), median $467,500 — 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.

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

In ZIP 32789, 244 homes are on the market and 25% are under contract — a steady corner of Winter Park.

Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).

In ZIP 32789 (Winter Park), 390 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.6% year over year, with a median 39 days on market. Right now 91 active and 26 pending listings put supply at about 5.2 months — a balanced market. See the live ZIP 32789 housing market and the Orange County market.

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

The defining trait here is age and scale. A median build year of 1956 and a median living area near 1,208 square feet point to compact, mid-century-era homes, with the oldest reaching back to 1920 and the newest built as recently as 2020. That newer end signals teardown-and-rebuild activity or infill — a pattern worth watching, because it changes what a lot is worth independent of the house on it.

Owner-occupancy runs on the lower side, with roughly 41% of homes carrying a homestead exemption. Practically, that means a meaningful share of these homes are held as rentals or second properties, which can affect turnover, upkeep patterns, and the mix of what comes to market. Buyers should underwrite each home's condition individually rather than assume uniform maintenance across the enclave.

A market this varied — century of build years, small footprints, a large renovated-versus-original gap — rewards someone who prices house by house instead of leaning on a neighborhood average. We walk each property for condition, systems, and lot value, and we tell you plainly when a listing's number reflects the work done or just the address.

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