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 $1,166,250. All the Oakland communities are listed below with links to view the homes for sale in the communities.
| Oakland Park | |
| John's Cove | |
| Hull Island at Oakland | |
| Johns Landing | |
| Trailside Station | |
| Oakland Trails | |
| 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 between 2024 and 2025. It currently has 2 single family homes for sale with an average list price of $1,897,000. The homes range in size from 3,665 ft2 to 3,876 ft2. The average annual property tax for Briley Farm is $2,870. |
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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 average annual property tax for Hull Island at Oakland is $1,551. |
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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 3 single family homes for sale with an average list price of $811,333. The homes range in size from 1,857 ft2 to 4,277 ft2. The average annual property tax for Hull Island at Oakland is $4,335. |
$652,000 |
John's CoveJohn's Cove is a single-family home community in Oakland, Florida, built between 2001 and 2006. It currently has no homes for sale. The homes range in size from 2,465 ft2 to 6,065 ft2. The average annual property tax for John's Cove is $9,084. |
$1,142,500 |
Johns LandingJohns Landing is a single-family home community in Oakland, Florida, built between 2000 and 2020. It currently has 5 single family homes for sale with an average list price of $771,159. The homes range in size from 1,956 ft2 to 5,222 ft2. The average annual property tax for Johns Landing is $5,625. |
$525,000 |
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 1 single family home for sale with a list price of $725,000 and 3 townhouses for sale with an average list price of $386,300. The homes range in size from 1,314 ft2 to 3,059 ft2. The average annual property tax for Longleaf at Oakland is $3,329. |
$405,000 |
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 13 single family homes for sale with an average list price of $1,072,413. The homes range in size from 1,584 ft2 to 5,754 ft2. The average annual property tax for Oakland Park is $4,892. |
$1,166,250 |
Oakland TrailsOakland Trails is a single-family home community in Oakland, Florida, built between 2017 and 2020 by Meritage Homes. It currently has 4 single family homes for sale with an average list price of $552,450. The homes range in size from 1,640 ft2 to 3,467 ft2. The average annual property tax for Oakland Trails is $4,061. |
$487,500 |
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 average annual property tax for Trailside Station is $3,174. |
$525,000 |
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