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Oakland was established in 1887 and is one of the oldest municipalities in Orange County. It is part of the Orlando–Kissimmee Metropolitan Statistical Area and features a variety of hiking trails in its nature preserve. Use our custom search tool to view all homes for sale above $600k in Oakland or click here to return to the list of surrounding towns and cities in the Kissimmee area. Have questions? Contact us here or schedule your FREE consultation here.


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  1. Photo of 1011 Johns Cove Lane, Oakland, FL 34787 (MLS # O6260124)
    $639,990
    Photo of 1011 Johns Cove Lane, Oakland, FL 34787 (MLS # O6260124)
    Photo of 1011 Johns Cove Lane, Oakland, FL 34787 (MLS # O6260124)
    1011 Johns Cove Lane, Oakland, FL
    1011 Johns Cove Lane
    Oakland, FL
    • 4 Beds
    • 3 Baths
    • 2,579 Home (sqft)
    • 3 Baths
    • 12,633 Lot (sqft)
  2. Photo of 1215 Johns Cove Lane, Oakland, FL 34787 (MLS # O6261895)
    $649,999
    Photo of 1215 Johns Cove Lane, Oakland, FL 34787 (MLS # O6261895)
    Photo of 1215 Johns Cove Lane, Oakland, FL 34787 (MLS # O6261895)
    1215 Johns Cove Lane, Oakland, FL
    1215 Johns Cove Lane
    Oakland, FL
    • 4 Beds
    • 2 Baths
    • 2,811 Home (sqft)
    • 2 Baths
    • 12,633 Lot (sqft)
  3. Photo of 1740 Standing Rock Circle, Oakland, FL 34787 (MLS # O6250033)
    $665,000
    Photo of 1740 Standing Rock Circle, Oakland, FL 34787 (MLS # O6250033)
    Photo of 1740 Standing Rock Circle, Oakland, FL 34787 (MLS # O6250033)
    1740 Standing Rock Circle, Oakland, FL
    1740 Standing Rock Circle
    Oakland, FL
    • 3 Beds
    • 3 Baths
    • 1,995 Home (sqft)
    • 3 Baths
    • 9,148 Lot (sqft)
  4. Photo of 70 Millholland Street, Oakland, FL 34760 (MLS # O6246862)
    $975,000
    Photo of 70 Millholland Street, Oakland, FL 34760 (MLS # O6246862)
    Photo of 70 Millholland Street, Oakland, FL 34760 (MLS # O6246862)
    70 Millholland Street, Oakland, FL
    70 Millholland Street
    Oakland, FL
    • 5 Beds
    • 3 Baths
    • 2,534 Home (sqft)
    • 3 Baths
    • 13,068 Lot (sqft)
  5. Photo of 110 W Railway Avenue, Oakland, FL 34760 (MLS # O6246673)
    $1,945,000
    Photo of 110 W Railway Avenue, Oakland, FL 34760 (MLS # O6246673)
    Photo of 110 W Railway Avenue, Oakland, FL 34760 (MLS # O6246673)
    17
     
    110 W Railway Avenue, Oakland, FL
    110 W Railway Avenue
    Oakland, FL
    • 5 Beds
    • 5 Baths
    • 3,876 Home (sqft)
    • 5 Baths
    • 13,504 Lot (sqft)
  6. Photo of 141 Millholland Street, Oakland, FL 34760 (MLS # O6243649)
    $1,935,000
    Photo of 141 Millholland Street, Oakland, FL 34760 (MLS # O6243649)
    Photo of 141 Millholland Street, Oakland, FL 34760 (MLS # O6243649)
    141 Millholland Street, Oakland, FL
    141 Millholland Street
    Oakland, FL
    • 4 Beds
    • 4 Baths
    • 3,920 Home (sqft)
    • 4 Baths
    • 1.12 Lot (ac)
  7. Photo of 511 Briley Avenue, Oakland, FL 34760 (MLS # O6228504)
    $1,849,000
    Photo of 511 Briley Avenue, Oakland, FL 34760 (MLS # O6228504)
    Photo of 511 Briley Avenue, Oakland, FL 34760 (MLS # O6228504)
    511 Briley Avenue, Oakland, FL
    511 Briley Avenue
    Oakland, FL
    • 5 Beds
    • 5 Baths
    • 3,665 Home (sqft)
    • 5 Baths
    • 13,504 Lot (sqft)
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