Oakland Park is a single-family home community in Winter Garden, Florida, built between 2008 and 2025 by David Weekley Homes, Ashton Woods Homes, Dream Finders Homes, and RockWell Homes. It currently has 11 single family homes for sale with an average list price of $1,244,802.73. For anyone looking for a brand new home, there are 3 new construction homes for sale. The homes range in size from 1,611 ft2 to 5,754 ft2. The HOA fees range from $183 to $625 per month. The average annual property tax for Oakland Park is $10,513.98. It is located in Orange County.
Oakland Park is an award-winning, 258-acre master-planned community in Winter Garden, Florida, nestled along the shores of Lake Apopka and directly connected to the West Orange Trail.
Designed with old-Florida charm, it features majestic live oaks, abundant open space, pedestrian-friendly streets with large front porches and rear-facing garages, and homes built primarily between 2008 and 2025 by builders such as David Weekley Homes, Ashton Woods, Dream Finders, J&J Building, and RockWell Homes in styles ranging from Craftsman and bungalow to Key West and traditional.
Every home meets green-certification standards in this environmentally focused neighborhood, which offers resort-style amenities including a clubhouse, zero-entry pool, playgrounds, parks, fitness facilities, fishing access, and golf-cart-friendly streets.
Residents enjoy quick access to historic downtown Winter Garden’s nationally ranked farmers market, shops, and restaurants, while remaining about 20 minutes from Walt Disney World and 30 minutes from downtown Orlando and the airport, with students served by Orange County schools such as Tildenville Elementary, Lakeview Middle, and West Orange High
Boat Facilities Cats Allowed Clubhouse Community Mailbox Dock Dog Park Dogs Allowed Fishing Fitness Fitness Center Gated Golf Golf Carts OK Lake Maintenance Grounds Marina Park Pickleball Playground Pool (Community) Recreation Area Recreation Facilities Sidewalks Street Lights Tennis Court(s) Trail(s) Water Access Waterfront
