50 total properties
Did you mean the neighborhood Oakland?
View 320 W SADLER AVENUE Oakland, FL MLS# O6436879
  • Virtual Tour
1 of 47
$199,000
2

Beds

1.0

Baths

722

Sq.Ft.

320 W SADLER AVENUE

Oakland, FL

Courtesy of OFFERPAD BROKERAGE FL LLC
View 1511 SWEET APPLE STREET Oakland, FL MLS# O6439535
$334,950
3

Beds

2.1

Baths

1,620

Sq.Ft.

1511 SWEET APPLE STREET

Oakland, FL

Courtesy of SOUTHERN PRESTIGE REALTY INC
View 2107 GOPHER TORTOISE TERRACE Oakland, FL MLS# S5159312
  • Recently Listed with Virtual Tour
1 of 50
$364,900
2

Beds

2.1

Baths

1,472

Sq.Ft.

2107 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of LPT REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2224 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6443996
$367,500
2

Beds

2.1

Baths

1,652

Sq.Ft.

2224 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 521 W HERRIOTT AVENUE Oakland, FL MLS# O6430972
  • New Construction with Virtual Tour
1 of 34
$415,000
3

Beds

2.0

Baths

1,170

Sq.Ft.

521 W HERRIOTT AVENUE

Oakland, FL

Courtesy of REAL BROKER, LLC
View 2273 STANDING ROCK CIRCLE Oakland, FL MLS# O6439158
    1 of 26
    OPEN HOUSE: Saturday 10/24 11:00 AM - 1:00 PM
    $479,900
    3

    Beds

    2.1

    Baths

    2,082

    Sq.Ft.

    2273 STANDING ROCK CIRCLE

    Oakland, FL

    Courtesy of REAL BROKER, LLC
    View 2199 WHITE FEATHER LOOP Oakland, FL MLS# W7890380
    • Recently Listed
    1 of 39
    $489,900
    3

    Beds

    2.1

    Baths

    1,909

    Sq.Ft.

    2199 WHITE FEATHER LOOP

    Oakland, FL

    Courtesy of DALTON WADE INC
    View 2259 WHITE FEATHER LOOP Oakland, FL MLS# O6381627
    $515,000
    4

    Beds

    2.1

    Baths

    2,204

    Sq.Ft.

    2259 WHITE FEATHER LOOP

    Oakland, FL

    Courtesy of YOUNG REAL ESTATE
    View 2696 BOBCAT CHASE BOULEVARD Oakland, FL MLS# S5158021
    $515,000
    3

    Beds

    2.1

    Baths

    1,811

    Sq.Ft.

    2696 BOBCAT CHASE BOULEVARD

    Oakland, FL

    Courtesy of THE PROPERTY FIRM
    View 990 STATIONSIDE DRIVE Oakland, FL MLS# O6440519
    $525,000
    4

    Beds

    2.0

    Baths

    2,028

    Sq.Ft.

    990 STATIONSIDE DRIVE

    Oakland, FL

    Courtesy of EXP REALTY LLC
    View 223 LARGOVISTA DR. Oakland, FL MLS# O6425925
    • Virtual Tour
    1 of 55
    $540,000
    4

    Beds

    2.1

    Baths

    2,486

    Sq.Ft.

    223 LARGOVISTA DR.

    Oakland, FL

    Courtesy of MARKET CONNECT REALTY LLC
    View 2471 SKY STONE COURT Oakland, FL MLS# S5156522
    • Virtual Tour
    1 of 54
    $559,000
    4

    Beds

    2.1

    Baths

    2,854

    Sq.Ft.

    2471 SKY STONE COURT

    Oakland, FL

    Courtesy of NUMBER 1 BROKER, LLC
    View 2561 SKY STONE COURT Oakland, FL MLS# O6445600
    • Virtual Tour
    1 of 40
    $565,000
    4

    Beds

    2.1

    Baths

    2,576

    Sq.Ft.

    2561 SKY STONE COURT

    Oakland, FL

    Courtesy of RC GROUP REALTY LLC
    View 514 N POLLARD STREET Oakland, FL MLS# O6332783
    $575,000
    0.0

    Baths

    514 N POLLARD STREET

    Oakland, FL

    Courtesy of REGENCY REAL ESTATE LLC
    View 523 WALKER STREET Oakland, FL MLS# O6430636
    • Virtual Tour
    1 of 5
    $595,000
    0.0

    Baths

    523 WALKER STREET

    Oakland, FL

    Courtesy of CORCORAN PREMIER REALTY
    View 100 MATHER SMITH DRIVE Oakland, FL MLS# O6443938
    $600,000
    3

    Beds

    2.0

    Baths

    1,571

    Sq.Ft.

    100 MATHER SMITH DRIVE

    Oakland, FL

    Courtesy of KELLER WILLIAMS CLASSIC
    View 2107 BAY LINE ROAD Oakland, FL MLS# O6443759
    • Virtual Tour
    1 of 57
    $615,000
    3

    Beds

    2.0

    Baths

    1,916

    Sq.Ft.

    2107 BAY LINE ROAD

    Oakland, FL

    Courtesy of KELLER WILLIAMS WINTER PARK
    View 38 S POLLARD STREET Oakland, FL MLS# O6394442
    • New Construction with Virtual Tour
    1 of 56
    $619,000
    4

    Beds

    2.1

    Baths

    1,872

    Sq.Ft.

    38 S POLLARD STREET

    Oakland, FL

    Courtesy of MS LAND & BUILDING LLC
    View 2017 BOSS HEWETT STREET Oakland, FL MLS# O6402045
    $649,900
    4

    Beds

    4.0

    Baths

    2,852

    Sq.Ft.

    2017 BOSS HEWETT STREET

    Oakland, FL

    Courtesy of CHARLES RUTENBERG REALTY ORLANDO
    View 726 REGINA CIRCLE Oakland, FL MLS# O6450677
    • Recently Listed
    1 of 36
    $695,000
    5

    Beds

    4.0

    Baths

    3,641

    Sq.Ft.

    726 REGINA CIRCLE

    Oakland, FL

    Courtesy of HOUWZER INC

    About Oakland

    Ideally located along the shores of Lake Apopka and surrounded by enormous oak trees, the Town of Oakland was first incorporated as long ago as 1887.  Oakland offers a quiet residential retreat and serene country atmosphere to a small population of less than 1,500 residents.  At the same time, the area surrounding the community has experienced considerable growth and development, dotting the region with new subdivisions and beautiful homes.  In fact, maintaining its traditional image of being "Nestled among the Oaks" has been one of the city's greatest challenges in the face of the area's rapid expansion.  Oakland is the proud home of the West Orange Trailhead and the Oakland Nature Preserve, providing excellent opportunities for recreation.  The trailhead attracts thousands of outdoor enthusiasts each year, while the Oakland Nature Preserve ensures a scenic retreat that showcases the splendor of native Florida plant and animal life. Residents and visitors alike appreciate Oakland as the epitome of yesterday's small and charming Florida town.

    Listings in Oakland, FL

    48

    Estimated median home price

    $796,000
    Oakland FL Homes for Sale & Properties

    Weichert Realtors is one of the nation's leading providers of Oakland, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Oakland, FL.

    Homes for Sale by Price in Oakland, FL

    PriceCount
    $0 - 100K0
    $100K - 200K1
    $200K - 300K0
    $300K - 400K3
    $400K - 500K3
    $500K - 600K9
    $600K - 700K4
    $700K - 800K6
    $800K - 900K3
    $900K - 1M2
    $1M - Max17

    Homes for Sale by Type in Oakland, FL

    Property TypeCount
    Single Family41
    Townhouse3
    Condo0
    Commercial0
    Rental2
    Lots and Land3
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms0

    (Data as of 10/21/2026)

    Information deemed reliable but not guaranteed.

    The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

    The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

    Data is updated as of 10/22/2026.

    Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

    Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

    Data is updated as of 10/22/2026.