Subdivisions & Condo Buildings in Oakland, FL

Listed below are all the subdivisions and buildings in Oakland with median sale prices for each community. We've also included some recent sales in some of those communities.


Top Subdivisions/Buildings

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 John's Cove with an average of $1,570,000.

John's Cove
$1,570,000
Oakland Park
$1,166,250
Hull Island at Oakland
$827,500
Johns Landing
$588,000
Oakland Trails
$475,000
Longleaf at Oakland
$435,000
Trailside Station
$410,000

Most Recent Homes for Sale in Oakland

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All Subdivisions/Condo Buildings in Oakland

Community Median Price
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Briley Farm

Briley Farm is a single-family home community in Oakland, Florida, built in 2025. It currently has 2 single family homes for sale with an average list price of $2,047,500. The homes have an average size of 3,876 ft2. The average annual property tax for Briley Farm is $2,877. It is located in Orange county.
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Hull Island at Oakland

Hull 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 $1,551.22. It is located in Orange county.
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Hull Island at Oakland

Hull 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 $888,980. The homes range in size from 1,857 ft2 to 4,277 ft2. The average annual property tax for Hull Island at Oakland is $4,768.07. It is located in Orange county.
Median Price: 827,500
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John's Cove

John's Cove is a single-family home community in Oakland, Florida, built between 2001 and 2020. It currently has 1 single family home for sale with a list price of $630,000. The homes range in size from 2,465 ft2 to 6,065 ft2. The average annual property tax for John's Cove is $8,742.05. It is located in Orange county.
Median Price: 1,570,000
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Johns Landing

Johns Landing is a single-family home community in Oakland, Florida, built between 2000 and 2020. It currently has 10 single family homes for sale with an average list price of $660,569.40. The homes range in size from 1,898 ft2 to 5,222 ft2. The average annual property tax for Johns Landing is $5,558.37. It is located in Orange county.
Median Price: 588,000
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Longleaf at Oakland

Longleaf 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 $579,000 and 4 townhouses for sale with an average list price of $407,950. The homes range in size from 1,472 ft2 to 3,059 ft2. The average annual property tax for Longleaf at Oakland is $4,087.02. It is located in Orange county.
Median Price: 435,000
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Oakland Park

Oakland 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 12 single family homes for sale with an average list price of $1,284,194.17. The homes range in size from 1,584 ft2 to 5,754 ft2. The average annual property tax for Oakland Park is $5,404.44. It is located in Orange county.
Median Price: 1,166,250
Oakland Trails

Oakland Trails

Oakland Trails is a single-family home community in Oakland, Florida, built between 2017 and 2020 by Meritage Homes. It currently has 5 single family homes for sale with an average list price of $622,960. The homes range in size from 1,640 ft2 to 3,512 ft2. The average annual property tax for Oakland Trails is $4,677.28. It is located in Orange county.
Median Price: 475,000
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Trailside Station

Trailside 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 $3,340.62. It is located in Orange county.
Median Price: 410,000
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