49 total properties
Did you mean the neighborhood Oakland?
View 150 HAMMOCK PRESERVE LOOP Oakland, FL MLS# O6443416
$879,000
4

Beds

3.0

Baths

2,246

Sq.Ft.

150 HAMMOCK PRESERVE LOOP

Oakland, FL

Courtesy of COMPASS FLORIDA 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 1016 CATORI ROAD Oakland, FL MLS# O6440957
  • Virtual Tour
1 of 76
$825,000
4

Beds

3.1

Baths

3,085

Sq.Ft.

1016 CATORI ROAD

Oakland, FL

Courtesy of HOMEVEST REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1970 STANDING ROCK CIRCLE Oakland, FL MLS# O6361226
$796,000
5

Beds

3.0

Baths

3,528

Sq.Ft.

1970 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of WEMERT GROUP REALTY LLC
View 16 OAKLAND POINTE CIRCLE Oakland, FL MLS# TB8513260
$795,999
5

Beds

3.0

Baths

3,413

Sq.Ft.

16 OAKLAND POINTE CIRCLE

Oakland, FL

Courtesy of JACK KELLER INC
View 1603 Johns Cove Lane Oakland, FL MLS# 1228387
  • Virtual Tour
1 of 41
OPEN HOUSE: Saturday 10/10 12:00 PM - 2:00 PM
$779,000
6

Beds

4.0

Baths

4,001

Sq.Ft.

1603 Johns Cove Lane

Oakland, FL

View 1603 JOHNS COVE LN Oakland, FL MLS# O6419418
  • Virtual Tour
1 of 41
OPEN HOUSE: Saturday 10/10 12:00 PM - 2:00 PM
$779,000
6

Beds

4.0

Baths

4,001

Sq.Ft.

1603 JOHNS COVE LN

Oakland, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
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 906 JOHNS POINT DRIVE Oakland, FL MLS# O6433996
$695,000
0.0

Baths

906 JOHNS POINT DRIVE

Oakland, FL

Courtesy of DALTON WADE INC
View 239 LARGOVISTA DRIVE Oakland, FL MLS# FC321273
  • Virtual Tour
1 of 50
OPEN HOUSE: Sunday 10/11 1:00 PM - 3:00 PM
$675,900
4

Beds

2.1

Baths

3,652

Sq.Ft.

239 LARGOVISTA DRIVE

Oakland, FL

Courtesy of APPROVED PATRIOT REALTY 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 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 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 100 MATHER SMITH DRIVE Oakland, FL MLS# O6443938
  • Recently Listed with Virtual Tour
1 of 30
OPEN HOUSE: Sunday 10/11 1:00 PM - 3:00 PM
$600,000
3

Beds

2.0

Baths

1,571

Sq.Ft.

100 MATHER SMITH DRIVE

Oakland, FL

Courtesy of KELLER WILLIAMS CLASSIC
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 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 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 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 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 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

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

$787,500
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 - 500K3
$500K - 600K10
$600K - 700K5
$700K - 800K5
$800K - 900K4
$900K - 1M2
$1M - Max16

Homes for Sale by Type in Oakland, FL

Property TypeCount
Single Family41
Townhouse2
Condo0
Commercial0
Rental2
Lots and Land4
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 10/7/2026)

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 10/9/2026.

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 10/9/2026.