43 total properties
Did you mean the neighborhood Oakland?
View 2451 SKY STONE COURT Oakland, FL MLS# S5141292
  • Virtual Tour
1 of 27
$625,000
5

Beds

3.1

Baths

3,007

Sq.Ft.

2451 SKY STONE COURT

Oakland, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 2606 BOBCAT CHASE BOULEVARD Oakland, FL MLS# O6351390
$629,000
4

Beds

2.1

Baths

2,473

Sq.Ft.

2606 BOBCAT CHASE BOULEVARD

Oakland, FL

Courtesy of BHHS FLORIDA REALTY
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 729 STRIHAL LOOP Oakland, FL MLS# O6381069
  • Virtual Tour
1 of 49
$679,900
4

Beds

3.1

Baths

3,583

Sq.Ft.

729 STRIHAL LOOP

Oakland, FL

Courtesy of LIBERTY HOME SALES INC
View 310 E GULLEY AVENUE Oakland, FL MLS# O6389102
$695,000
3

Beds

2.0

Baths

1,763

Sq.Ft.

310 E GULLEY AVENUE

Oakland, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 38 S POLLARD STREET Oakland, FL MLS# O6394442
  • Recently Listed with Virtual Tour
1 of 59
$699,000
4

Beds

2.1

Baths

1,872

Sq.Ft.

38 S POLLARD STREET

Oakland, FL

Courtesy of MS LAND & BUILDING LLC
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 1231 FOLTZ LOOP Oakland, FL MLS# O6393970
  • Recently Listed with Virtual Tour
1 of 30
$874,900
4

Beds

4.1

Baths

3,134

Sq.Ft.

1231 FOLTZ LOOP

Oakland, FL

Courtesy of SOUTHERN REALTY GROUP LLC
View 8 WINTERS LANDING DRIVE Oakland, FL MLS# O6385221
  • Recently Listed with Virtual Tour
1 of 47
$885,000
4

Beds

3.0

Baths

2,850

Sq.Ft.

8 WINTERS LANDING DRIVE

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 624 HULL ISLAND DRIVE Oakland, FL MLS# O6359887
$894,000
4

Beds

2.0

Baths

2,708

Sq.Ft.

624 HULL ISLAND DRIVE

Oakland, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 537 N POLLARD Oakland, FL MLS# O6376984
  • Virtual Tour
1 of 18
$895,000
Studio

Beds

0.0

Baths

537 N POLLARD

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 134 SOUTHERN RAILWAY 7 Oakland, FL MLS# O6300839
  • New Construction with Virtual Tour
1 of 13
$1,220,000
3,248

Sq.Ft.

134 SOUTHERN RAILWAY 7

Oakland, FL

Courtesy of THE MARKS GROUP REALTY, LLC
View 1156 CIVITAS WAY Oakland, FL MLS# O6385496
  • Virtual Tour
1 of 76
$1,275,000
4

Beds

2.1

Baths

2,710

Sq.Ft.

1156 CIVITAS WAY

Oakland, FL

Courtesy of DALTON WADE INC
View 556 WALKER STREET Oakland, FL MLS# O6388702
  • Virtual Tour
1 of 11
$1,295,000
Studio

Beds

0.0

Baths

556 WALKER STREET

Oakland, FL

Courtesy of CORCORAN PREMIER REALTY
View 620 N TUBB STREET Oakland, FL MLS# O6362142
  • Virtual Tour
1 of 62
$1,499,000
6

Beds

7.1

Baths

5,614

Sq.Ft.

620 N TUBB STREET

Oakland, FL

Courtesy of OAKSTRAND REALTY
View 1412 JOHNS COVE LANE Oakland, FL MLS# O6391735
  • Virtual Tour
1 of 78
$1,588,000
4

Beds

4.1

Baths

3,613

Sq.Ft.

1412 JOHNS COVE LANE

Oakland, FL

Courtesy of NEXT RESIDENCE REALTY LLC
View 511 BRILEY AVENUE Oakland, FL MLS# O6391844
  • New Construction with Virtual Tour
1 of 55
$1,949,000
5

Beds

4.1

Baths

3,862

Sq.Ft.

511 BRILEY AVENUE

Oakland, FL

Courtesy of CORCORAN PREMIER REALTY
View 1106 SARAH MATHEWS DRIVE Oakland, FL MLS# O6375487
  • New Construction
1 of 4
$1,975,000
5

Beds

5.1

Baths

3,596

Sq.Ft.

1106 SARAH MATHEWS DRIVE

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 1258 RIDGE LAKE WAY Oakland, FL MLS# O6373776
  • New Construction
1 of 3
$1,998,000
4

Beds

4.0

Baths

4,557

Sq.Ft.

1258 RIDGE LAKE WAY

Oakland, FL

Courtesy of NEW HOMES REAL ESTATE, INC.
View 1146 PRADO LANE Oakland, FL MLS# O6359354
  • New Construction
1 of 16
$2,130,760
5

Beds

5.1

Baths

3,992

Sq.Ft.

1146 PRADO LANE

Oakland, FL

Courtesy of REGENCY REAL ESTATE 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

42

Estimated median home price

$634,250
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 - 100K2
$100K - 200K0
$200K - 300K0
$300K - 400K6
$400K - 500K5
$500K - 600K6
$600K - 700K6
$700K - 800K1
$800K - 900K4
$900K - 1M0
$1M - Max12

Homes for Sale by Type in Oakland, FL

Property TypeCount
Single Family25
Townhouse6
Condo0
Commercial1
Rental3
Lots and Land9
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 4/13/2026)

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 4/14/2026.