Oakland Shores
Homes for Sale in Maitland, FL

Oakland Shores market snapshot (as of September 20, 2026): the median sale price is about $500K ($322 per sq ft over the trailing 12 months of closed sales), and a median 5 days on market for closed sales.

In ZIP 32751 (Maitland), 301 homes closed in the last 12 months at a median of $470K ($261/sq ft), down 1.0% year over year, with a median 31 days on market. Right now 34 active and 17 pending listings put supply at about 3.4 months — a healthy market. See the live ZIP 32751 housing market and the Orange County market.

County records show 13 qualified sales in Oakland Shores across 2024–2025 (4 in 2024, 9 in 2025), median $500,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.

Oakland Shores is a community of 128 homes in Maitland, Seminole County, built between 1955 and 2015 (median 1958.5), with a median living area of about 1,846 square feet. 85% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

A compact, owner-occupied enclave in Seminole County's slice of Maitland, where mid-century roots meet occasional newer rebuilds and living space runs a practical 1,845 square feet at the median.

The defining feature here is age spread. The median home dates to the late 1950s, but the range runs all the way to 2015, so within these 128 homes you'll find original mid-century construction alongside teardown rebuilds and updated renovations. That mix is why price here is condition-driven: two homes of similar size can sit far apart depending on systems, roof, and finishes.

At a median of roughly 1,845 square feet, floor plans lean toward manageable single-story living rather than sprawling new-build footprints. Buyers evaluating an unrenovated original should budget for the usual mid-century line items and inspect accordingly; buyers targeting a rebuilt or updated home will pay for that work up front and see fewer of them come available.

In a 128-home community with high owner-occupancy and thin turnover, the difference between overpaying and buying well is knowing which homes are original and which have been reworked. We read each listing against its condition and vintage, not a headline price, and we help sellers position updated homes to their advantage and price original ones honestly.

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