Oakland Park Homes for Sale in Winter Garden, FL

Oakland Park market snapshot (as of June 23, 2026): the median sale price is about $1.0M ($398 per sq ft), with homes averaging 39 days on market and 3.0 months of supply, a seller's market. Based on 24 recent closings in live Stellar MLS data.

Oakland Park is a planned traditional neighborhood development straddling the Town of Oakland and the city of Winter Garden, on roughly 258 acres along the south shore of Lake Apopka. Its layout draws on early twentieth-century small-town design, with homes set close to the street, alleys, and front porches, in a mix of Colonial Revival, Victorian, Craftsman, Spanish Colonial, and Florida Vernacular styles (source: liveatoaklandpark.com).

The community markets itself as a certified green neighborhood, with homes built to Florida Green Building Coalition standards, and it is built around open space rather than a golf course: trails, parks, a community garden, pocket lakes including Lake Brim, and frontage on Lake Apopka. Resort-style common amenities include a clubhouse with a zero-entry pool, a playground, pavilions, and picnic areas (source: rockwell-homes.com, liveatoaklandpark.com).

Because the neighborhood has delivered in phases since the late 2000s, buyers will find both resale homes from the early phases and newer construction. Condition, vintage, and which street or pond a home faces drive value more than square footage alone.

The location is the other half of the story. Oakland Park sits on the West Orange Trail in historic Oakland, minutes from downtown Winter Garden and the Plant Street Market, with the State Road 429 Western Beltway close by for the wider Orlando commute. Confirm school zoning and any community development district assessment for a specific address before you offer.