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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 under $400k 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 527 W Herriott Avenue, Oakland, FL 34760 (MLS # O6240288)
    $309,900
    Photo of 527 W Herriott Avenue, Oakland, FL 34760 (MLS # O6240288)
    Photo of 527 W Herriott Avenue, Oakland, FL 34760 (MLS # O6240288)
    527 W Herriott Avenue, Oakland, FL
    527 W Herriott Avenue
    Oakland, FL
    • 3 Beds
    • 3 Baths
    • 1,019 Home (sqft)
    • 3 Baths
    • 7,841 Lot (sqft)
  2. Photo of 1515 Sweet Apple St, Oakland, FL 34787 (MLS # O6236867)
    $364,000
    Photo of 1515 Sweet Apple St, Oakland, FL 34787 (MLS # O6236867)
    Photo of 1515 Sweet Apple St, Oakland, FL 34787 (MLS # O6236867)
    1515 Sweet Apple St, Oakland, FL
    1515 Sweet Apple St
    Oakland, FL
    • 2 Beds
    • 3 Baths
    • 1,497 Home (sqft)
    • 3 Baths
    • 1,743 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 12/22/24 6:20 PM PST.

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