Why Oakland, Florida real estate is booming (2026 guide)

Oakland, Florida — a small historic town on the south shore of Lake Apopka in west Orange County — has become one of the area's most sought-after places to build a luxury home.

The draw: small-town charm and tree-lined streets, the revitalization of Lake Apopka, direct access to the West Orange Trail, proximity to downtown Winter Garden, and new luxury communities like Briley Farm. Matt and Chocky Burks of Corcoran Premier Realty are active specialists in Oakland luxury and new construction.

Why is Oakland, FL real estate in demand?

Historic charm, Lake Apopka's revitalization, the West Orange Trail, closeness to downtown Winter Garden, and new luxury communities (e.g., Briley Farm) — where custom homes have recently listed from roughly $1.95M to over $4M, while Oakland's overall median home price is around $635K.

What kind of homes are in Oakland?

A mix of historic homes and new luxury custom builds, including estate lots and lakefront homesites near Lake Apopka.

Who's the expert on Oakland luxury real estate?

Matt Burks of Corcoran Premier Realty, on-site regularly at Briley Farm, with his mother and teammate Chocky Burks (former Sotheby's New Homes Director).