Top Communities in Oakland, FL
We have calculated the top communities in Oakland based on the median sale prices of homes. The Oakland community with the highest average home sale price was Oakland Park with an average of $1,835,000. All the Oakland communities are listed below with links to view the homes for sale in the communities.
| Oakland Park | |
| John's Cove | |
| Winters Landing | |
| Briley Farm | |
| Hull Island at Oakland | |
| Johns Landing | |
| Oakland Trails | |
| Trailside Station | |
| Longleaf at Oakland |
All Subdivisions/Condo Buildings in Oakland
| Community | Median Price |
|---|---|
Briley FarmBriley Farm is a single-family home community in Oakland, Florida, built in 2026. It currently has 9 lots for sale with an average list price of $820,000. The homes have an average size of 6,428 ft2. The HOA fees range from $1,800 to $1,800 per month. The average annual property tax for Briley Farm is $4,711. It is located in Orange County. |
$800,000 |
Grove at the Harvest DistrictGrove at the Harvest District is a single-family home community in Oakland, Florida, built in 2025. It currently has 3 single family homes for sale with an average list price of $2,148,333.33. The homes range in size from 3,596 ft2 to 4,859 ft2. The HOA fees range from $150 to $1,800 per month. The average annual property tax for Grove at the Harvest District is $399. It is located in Orange County. |
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Hull Island at OaklandHull Island at Oakland is a single-family home community in Oakland, Florida, built in 2022 by M/I Homes. It currently has no homes for sale. The homes have an average size of 3,562 ft2. The HOA fees range from $130 to $130 per month. The average annual property tax for Hull Island at Oakland is $1,551.22. It is located in Orange County. |
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Hull Island at OaklandHull Island at Oakland is a single-family home community in Winter Garden (Oakland), Florida, built between 2002 and 2023 by M/I Homes. It currently has 5 single family homes for sale with an average list price of $738,580. The homes range in size from 1,857 ft2 to 4,277 ft2. The HOA fees range from $122 to $188 per month. The average annual property tax for Hull Island at Oakland is $4,844.79. It is located in Orange County. |
$690,000 |
John's CoveJohn's Cove is a single-family home community in Oakland, Florida, built between 2001 and 2020. It currently has 3 single family homes for sale with an average list price of $1,066,329.67. The homes range in size from 2,465 ft2 to 6,065 ft2. The HOA fees range from $600 to $1,889 per month. The average annual property tax for John's Cove is $9,465.11. It is located in Orange County. |
$1,030,000 |
Johns LandingJohns Landing is a picturesque, gated community in Oakland, Florida, nestled along the serene shores of Johns Lake. This upscale neighborhood of approximately 272 single-family homes offers a blend of luxury and tranquility with easy access to the Florida Turnpike, West Orange Trail, and nearby attractions. Residents enjoy a variety of amenities, including a multi-purpose court for tennis, pickleball, and basketball, a colorful children’s playground, and a scenic boat dock and ramp providing direct access to Johns Lake for water activities. Sidewalks winding through the community’s lush foliage and ponds create an inviting setting for strolls or bike rides, enhancing the peaceful, family-friendly atmosphere. Johns Landing is a single-family home community in Oakland (Winter Garden), Florida, built between 2000 and 2020. It currently has 14 single family homes for sale with an average list price of $784,535.43. The homes range in size from 1,621 ft2 to 5,222 ft2. The HOA fees range from $70 to $1,000 per month. The average annual property tax for Johns Landing is $5,513.31. It is located in Orange County. |
$615,000 |
Longleaf at OaklandLongleaf at Oakland is a townhouse and single-family home community in Oakland, Florida, built between 2019 and 2021 by Pulte Homes. It currently has 3 single family homes for sale with an average list price of $546,637.67 and 2 townhouses for sale with an average list price of $403,950. The homes range in size from 1,472 ft2 to 3,059 ft2. The HOA fees range from $164 to $402 per month. The average annual property tax for Longleaf at Oakland is $4,163.74. It is located in Orange County. |
$387,900 |
Oakland ParkOakland Park is a single-family home community in Winter Garden, Florida, built between 2008 and 2025 by David Weekley Homes, Dream Finders Homes, and RockWell Homes. It currently has 10 single family homes for sale with an average list price of $1,232,783. The homes range in size from 1,584 ft2 to 5,754 ft2. The HOA fees range from $125 to $2,188 per month. The average annual property tax for Oakland Park is $5,473.08. It is located in Orange County. |
$1,835,000 |
Oakland TrailsOakland Trails is a single-family home community in Oakland, Florida, built between 2017 and 2020 by Meritage Homes. It currently has 9 single family homes for sale with an average list price of $543,277.78. The homes range in size from 1,640 ft2 to 3,449 ft2. The HOA fees range from $103 to $383 per month. The average annual property tax for Oakland Trails is $4,731.85. It is located in Orange County. |
$545,000 |
Trailside StationTrailside Station is a single-family home community in Oakland (Winter Garden), Florida, built between 2000 and 2002. It currently has no homes for sale. The homes range in size from 1,597 ft2 to 2,627 ft2. The HOA fees range from $350 to $360 per month. The average annual property tax for Trailside Station is $3,340.62. It is located in Orange County. |
$410,000 |
Winters LandingThe community’s prime location provides easy access to the nearby Oakland Nature Preserve for outdoor enthusiasts and the West Orange Trail, perfect for biking, running, or leisurely strolls. Its proximity to major highways like SR 429 and Florida’s Turnpike also ensures convenient commuting to Downtown Orlando and nearby attractions. Winters Landing is a single-family home community in Oakland (Winter Garden), Florida, built between 2005 and 2007. It currently has no homes for sale. The homes range in size from 2,447 ft2 to 3,698 ft2. The HOA fees range from $140 to $250 per month. The average annual property tax for Winters Landing is $5,104.87. It is located in Orange County. |
$840,000 |
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