Oakland Florida Homes for Sale

Sorry, no results were found from your filter criteria.

Please try a new search or expand your current search.

37 total properties
Did you mean the neighborhood Oakland?
View 510 BRILEY AVENUE Oakland, FL MLS# O6422258
  • New Construction with Virtual Tour
1 of 100
$3,575,000
5

Beds

5.2

Baths

5,478

Sq.Ft.

510 BRILEY AVENUE

Oakland, FL

View 1128 PRADO LANE Oakland, FL MLS# O6413047
  • New Construction with Virtual Tour
1 of 13
$2,800,000
6

Beds

6.1

Baths

4,658

Sq.Ft.

1128 PRADO LANE

Oakland, FL

View 529 JOHNS LANDING WAY Oakland, FL MLS# O6419615
  • Recently Listed with Virtual Tour
1 of 45
$639,000
4

Beds

3.0

Baths

2,650

Sq.Ft.

529 JOHNS LANDING WAY

Oakland, FL

Courtesy of REAL BROKER, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 710 REGINA CIRCLE Oakland, FL MLS# O6415350
    1 of 47
    OPEN HOUSE: Saturday 7/11 12:00 PM - 2:00 PM
    $669,900
    5

    Beds

    4.0

    Baths

    3,285

    Sq.Ft.

    710 REGINA CIRCLE

    Oakland, FL

    View 402 N POLLARD STREET Oakland, FL MLS# O6405707
    • New Construction with Virtual Tour
    1 of 63
    OPEN HOUSE: Wednesday 7/8 11:00 AM - 4:00 PM
    $3,495,000
    5

    Beds

    5.1

    Baths

    5,001

    Sq.Ft.

    402 N POLLARD STREET

    Oakland, FL

    View 1143 HULL ISLAND DRIVE Oakland, FL MLS# O6413213
    $749,000
    4

    Beds

    4.0

    Baths

    2,788

    Sq.Ft.

    1143 HULL ISLAND DRIVE

    Oakland, FL

    View 16 OAKLAND POINTE CIRCLE Oakland, FL MLS# TB8513260
    $799,999
    5

    Beds

    3.0

    Baths

    3,413

    Sq.Ft.

    16 OAKLAND POINTE CIRCLE

    Oakland, FL

    Courtesy of JACK KELLER INC
    View 2247 WHITE FEATHER LOOP Oakland, FL MLS# S5150852
    $457,900
    3

    Beds

    2.1

    Baths

    1,838

    Sq.Ft.

    2247 WHITE FEATHER LOOP

    Oakland, FL

    View 1108 RIVERWAY DRIVE Oakland, FL MLS# O6407380
    $1,025,000
    5

    Beds

    3.0

    Baths

    2,999

    Sq.Ft.

    1108 RIVERWAY DRIVE

    Oakland, FL

    View 918 HULL ISLAND DRIVE Oakland, FL MLS# O6404554
    $729,900
    4

    Beds

    3.0

    Baths

    2,268

    Sq.Ft.

    918 HULL ISLAND DRIVE

    Oakland, FL

    Courtesy of BHHS FLORIDA REALTY
    View 1137 PRADO LANE Oakland, FL MLS# O6402288
    • New Construction
    1 of 4
    $2,395,000
    5

    Beds

    5.1

    Baths

    4,527

    Sq.Ft.

    1137 PRADO LANE

    Oakland, FL

    Courtesy of REGENCY REAL ESTATE LLC
    View 556 WALKER STREET Oakland, FL MLS# O6402404
    • Virtual Tour
    1 of 5
    $1,295,000
    Studio

    Beds

    0.0

    Baths

    556 WALKER STREET

    Oakland, FL

    View 2017 BOSS HEWETT STREET Oakland, FL MLS# O6402045
    $724,900
    4

    Beds

    4.0

    Baths

    2,852

    Sq.Ft.

    2017 BOSS HEWETT STREET

    Oakland, FL

    Courtesy of CHARLES RUTENBERG REALTY ORLANDO
    View 219 LARGOVISTA DRIVE Oakland, FL MLS# O6401756
    • Virtual Tour
    1 of 24
    $1,025,000
    5

    Beds

    4.0

    Baths

    3,951

    Sq.Ft.

    219 LARGOVISTA DRIVE

    Oakland, FL

    Courtesy of NOVARE REAL ESTATE LLC
    View 250 N WALKER STREET Oakland, FL MLS# G5110973
    • Virtual Tour
    1 of 76
    $1,145,000
    4

    Beds

    2.1

    Baths

    2,469

    Sq.Ft.

    250 N WALKER STREET

    Oakland, FL

    View 1937 STANDING ROCK CIRCLE Oakland, FL MLS# O6398113
    $499,000
    3

    Beds

    2.1

    Baths

    2,069

    Sq.Ft.

    1937 STANDING ROCK CIRCLE

    Oakland, FL

    Courtesy of REAL BROKER, LLC
    View 15992 W COLONIAL DRIVE Oakland, FL MLS# O6395167
    $3,200,000
    41

    Beds

    75.0

    Baths

    17,021

    Sq.Ft.

    15992 W COLONIAL DRIVE

    Oakland, FL

    Courtesy of REMAX SUNSTATE REALTY
    View 38 S POLLARD STREET Oakland, FL MLS# O6394442
    • New Construction with Virtual Tour
    1 of 56
    $629,999
    4

    Beds

    2.1

    Baths

    1,872

    Sq.Ft.

    38 S POLLARD STREET

    Oakland, FL

    Courtesy of MS LAND & BUILDING LLC
    View 812 JOHNS POINT DRIVE Oakland, FL MLS# O6393574
    $2,699,000
    5

    Beds

    6.0

    Baths

    4,373

    Sq.Ft.

    812 JOHNS POINT DRIVE

    Oakland, FL

    View 2117 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6385739
    $360,000
    2

    Beds

    2.1

    Baths

    1,497

    Sq.Ft.

    2117 GOPHER TORTOISE TERRACE

    Oakland, FL

    Courtesy of SERHANT

    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

    37

    Estimated median home price

    $874,900
    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 - 200K0
    $200K - 300K0
    $300K - 400K3
    $400K - 500K2
    $500K - 600K4
    $600K - 700K4
    $700K - 800K5
    $800K - 900K2
    $900K - 1M0
    $1M - Max17

    Homes for Sale by Type in Oakland, FL

    Property TypeCount
    Single Family29
    Townhouse3
    Condo0
    Commercial0
    Rental2
    Lots and Land4
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms0

    (Data as of 7/8/2026)

    Information deemed reliable but not guaranteed.

    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 7/8/2026.