31 total properties
Did you mean the neighborhood Oakland?
View 2065 WHITE FEATHER LOOP Oakland, FL MLS# O6379741
  • Recently Listed with Virtual Tour
1 of 44
$560,000
3

Beds

2.1

Baths

2,089

Sq.Ft.

2065 WHITE FEATHER LOOP

Oakland, FL

Courtesy of PINK MIAMI
View 2169 BAY LINE ROAD Oakland, FL MLS# O6379555
  • Recently Listed with Virtual Tour
1 of 61
$665,000
4

Beds

3.0

Baths

2,274

Sq.Ft.

2169 BAY LINE ROAD

Oakland, FL

Courtesy of LPT REALTY, LLC
View 537 N POLLARD Oakland, FL MLS# O6376984
  • Recently Listed with Virtual Tour
1 of 18
$895,000
Studio

Beds

0.0

Baths

537 N POLLARD

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 529 N POLLARD STREET Oakland, FL MLS# O6378960
$895,000
Studio

Beds

0.0

Baths

529 N POLLARD STREET

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 2208 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6377704
  • Recently Listed with Virtual Tour
1 of 50
$409,000
3

Beds

2.1

Baths

1,620

Sq.Ft.

2208 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of ORLANDO PROP MGMNT RLTY LLC
View 2100 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6374216
  • Recently Listed with Virtual Tour
1 of 58
$395,000
2

Beds

2.1

Baths

1,620

Sq.Ft.

2100 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of MARKET CONNECT REALTY LLC
View 1227 RIDGE LAKE WAY Oakland, FL MLS# O6376717
  • Recently Listed with Virtual Tour
1 of 5
$455,000
Studio

Beds

0.0

Baths

1227 RIDGE LAKE WAY

Oakland, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
View 570 JOHNS LANDING WAY Oakland, FL MLS# G5107059
$690,000
5

Beds

4.0

Baths

4,030

Sq.Ft.

570 JOHNS LANDING WAY

Oakland, FL

Courtesy of DENIZ REALTY PARTNERS LLC
View 2029 WHITE FEATHER LOOP Oakland, FL MLS# O6374262
  • Virtual Tour
1 of 77
$489,900
3

Beds

2.1

Baths

1,909

Sq.Ft.

2029 WHITE FEATHER LOOP

Oakland, FL

Courtesy of ERIC BRESS REAL ESTATE LLC
View 2139 BAY LINE ROAD Oakland, FL MLS# O6373785
$649,000
4

Beds

3.0

Baths

2,281

Sq.Ft.

2139 BAY LINE ROAD

Oakland, FL

Courtesy of MARKET CONNECT REALTY LLC
View 1490 STONE ARROW COURT Oakland, FL MLS# S5141442
  • Virtual Tour
1 of 48
$620,000
5

Beds

3.1

Baths

3,248

Sq.Ft.

1490 STONE ARROW COURT

Oakland, FL

Courtesy of NUMBER 1 BROKER, LLC
View 2451 SKY STONE COURT Oakland, FL MLS# S5141292
  • Virtual Tour
1 of 53
$715,000
5

Beds

3.1

Baths

3,007

Sq.Ft.

2451 SKY STONE COURT

Oakland, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 321 E GULLEY AVENUE Oakland, FL MLS# O6370362
  • Virtual Tour
1 of 20
$395,000
Studio

Beds

0.0

Baths

321 E GULLEY AVENUE

Oakland, FL

Courtesy of LUXE PROPERTIES LLC
View 2135 STANDING ROCK CIRCLE Oakland, FL MLS# O6370898
$474,990
3

Beds

2.1

Baths

2,078

Sq.Ft.

2135 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of KELLER WILLIAMS WINTER PARK
View 717 STRIHAL LOOP Oakland, FL MLS# O6367476
  • Virtual Tour
1 of 32
$480,000
4

Beds

2.0

Baths

2,065

Sq.Ft.

717 STRIHAL LOOP

Oakland, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 847 CURA COURT Oakland, FL MLS# O6364456
  • Virtual Tour
1 of 49
$639,500
4

Beds

3.0

Baths

3,000

Sq.Ft.

847 CURA COURT

Oakland, FL

Courtesy of URBAN-O REAL ESTATE SOLUTIONS
View 2450 STANDING ROCK CIRCLE Oakland, FL MLS# O6360017
$704,500
5

Beds

4.0

Baths

3,163

Sq.Ft.

2450 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 1970 STANDING ROCK CIRCLE Oakland, FL MLS# O6361226
$800,000
5

Beds

3.0

Baths

3,528

Sq.Ft.

1970 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of WEMERT GROUP REALTY LLC
View 507 W OAKLAND AVENUE Oakland, FL MLS# O6357656
  • Virtual Tour
1 of 48
$364,900
3

Beds

2.0

Baths

1,338

Sq.Ft.

507 W OAKLAND AVENUE

Oakland, FL

Courtesy of REAL BROKER, LLC
View 501 E OAKLAND AVENUE Oakland, FL MLS# O6355030
  • Virtual Tour
1 of 39
$875,000
4

Beds

3.1

Baths

3,448

Sq.Ft.

501 E OAKLAND AVENUE

Oakland, FL

Courtesy of HOMEVEST REALTY

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

$677,500
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

Price Count
$0 - 100K 1
$100K - 200K 0
$200K - 300K 0
$300K - 400K 5
$400K - 500K 9
$500K - 600K 2
$600K - 700K 8
$700K - 800K 3
$800K - 900K 3
$900K - 1M 2
$1M - Max 15

Homes for Sale by Type in Oakland, FL

Property Type Count
Single Family 32
Townhouse 2
Condo 0
Commercial 3
Rental 3
Lots and Land 11
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 2/7/2026)

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 2/8/2026.