48 total properties
Did you mean the neighborhood Oakland?
View 2224 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6443996
$379,900
2

Beds

2.1

Baths

1,652

Sq.Ft.

2224 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of LAKESIDE REALTY WINDERMERE INC
View 2561 SKY STONE COURT Oakland, FL MLS# O6445600
  • Recently Listed with 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 150 HAMMOCK PRESERVE LOOP Oakland, FL MLS# O6443416
  • Recently Listed
1 of 49
OPEN HOUSE: Saturday 10/3 11:00 AM - 1:00 PM
$890,000
4

Beds

3.0

Baths

2,246

Sq.Ft.

150 HAMMOCK PRESERVE LOOP

Oakland, FL

Courtesy of COMPASS FLORIDA LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 2107 BAY LINE ROAD Oakland, FL MLS# O6443759
  • Recently Listed with Virtual Tour
1 of 57
$625,000
3

Beds

2.0

Baths

1,916

Sq.Ft.

2107 BAY LINE ROAD

Oakland, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 100 MATHER SMITH DRIVE Oakland, FL MLS# O6443938
  • Recently Listed with Virtual Tour
1 of 30
$600,000
3

Beds

2.0

Baths

1,571

Sq.Ft.

100 MATHER SMITH DRIVE

Oakland, FL

Courtesy of KELLER WILLIAMS CLASSIC
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 2470 STANDING ROCK CIRCLE Oakland, FL MLS# O6443027
  • Recently Listed with Virtual Tour
1 of 48
$730,000
5

Beds

3.0

Baths

3,430

Sq.Ft.

2470 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of HOMEVEST REALTY
View 81 MILLHOLLAND STREET Oakland, FL MLS# O6442710
  • Recently Listed with Virtual Tour
1 of 73
$1,275,000
3

Beds

3.0

Baths

3,887

Sq.Ft.

81 MILLHOLLAND STREET

Oakland, FL

Courtesy of EXP REALTY LLC
View 1184 BOBCAT CHASE BOULEVARD Oakland, FL MLS# O6442799
  • Recently Listed with Virtual Tour
1 of 52
OPEN HOUSE: Saturday 10/3 12:00 PM - 2:00 PM
$499,900
3

Beds

2.1

Baths

1,811

Sq.Ft.

1184 BOBCAT CHASE BOULEVARD

Oakland, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 1016 CATORI ROAD Oakland, FL MLS# O6440957
  • Recently Listed with Virtual Tour
1 of 76
$825,000
4

Beds

3.1

Baths

3,085

Sq.Ft.

1016 CATORI ROAD

Oakland, FL

View 137 PETRIS AVENUE Oakland, FL MLS# O6440357
  • Recently Listed with Virtual Tour
1 of 74
$1,495,000
4

Beds

3.1

Baths

3,620

Sq.Ft.

137 PETRIS AVENUE

Oakland, FL

View 2273 STANDING ROCK CIRCLE Oakland, FL MLS# O6439158
$479,900
3

Beds

2.1

Baths

2,082

Sq.Ft.

2273 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of REAL BROKER, LLC
View 166 HAMMOCK PRESERVE LOOP Oakland, FL MLS# O6439973
  • New Construction with Virtual Tour
1 of 15
$850,000
4

Beds

4.0

Baths

3,186

Sq.Ft.

166 HAMMOCK PRESERVE LOOP

Oakland, FL

Courtesy of GOYAL & DECOSTER REALTY
View 239 LARGOVISTA DRIVE Oakland, FL MLS# FC321273
  • Virtual Tour
1 of 50
$675,900
4

Beds

2.1

Baths

3,652

Sq.Ft.

239 LARGOVISTA DRIVE

Oakland, FL

Courtesy of APPROVED PATRIOT REALTY LLC
View 226 HAMMOCK PRESERVE LOOP Oakland, FL MLS# G5117627
$889,900
4

Beds

3.0

Baths

2,239

Sq.Ft.

226 HAMMOCK PRESERVE LOOP

Oakland, FL

Courtesy of OLYMPUS EXECUTIVE REALTY INC
View 1511 SWEET APPLE STREET Oakland, FL MLS# O6439535
$355,000
3

Beds

2.1

Baths

1,620

Sq.Ft.

1511 SWEET APPLE STREET

Oakland, FL

View 2696 BOBCAT CHASE BOULEVARD Oakland, FL MLS# S5158021
  • Recently Listed with Virtual Tour
1 of 58
$515,000
3

Beds

2.1

Baths

1,811

Sq.Ft.

2696 BOBCAT CHASE BOULEVARD

Oakland, FL

Courtesy of THE PROPERTY FIRM
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

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

View 1112 HULL ISLAND DRIVE Oakland, FL MLS# O6434371
$1,400,000
4

Beds

3.1

Baths

3,562

Sq.Ft.

1112 HULL ISLAND DRIVE

Oakland, FL

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

49

Estimated median home price

$795,000
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 - 400K2
$400K - 500K4
$500K - 600K10
$600K - 700K5
$700K - 800K5
$800K - 900K4
$900K - 1M1
$1M - Max17

Homes for Sale by Type in Oakland, FL

Property TypeCount
Single Family42
Townhouse2
Condo0
Commercial0
Rental2
Lots and Land4
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 9/29/2026)

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 10/1/2026.

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 10/1/2026.