40 total properties
Did you mean the neighborhood Oakland?
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 1106 SARAH MATHEWS DRIVE Oakland, FL MLS# O6375487
  • Recently Listed
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 906 ALLENDALE LANE Oakland, FL MLS# G5107489
$1,809,000
4

Beds

4.0

Baths

3,784

Sq.Ft.

906 ALLENDALE LANE

Oakland, FL

Courtesy of CENTURY 21 CARIOTI
The time to sell is now! THE TIME TO SELL IS NOW!
View 1207 RIDGE LAKE WAY Oakland, FL MLS# O6316643
  • New Construction with Virtual Tour
1 of 7
$1,700,000
5

Beds

3.1

Baths

3,909

Sq.Ft.

1207 RIDGE LAKE WAY

Oakland, FL

Courtesy of NEW HOMES REAL ESTATE, INC.
View 620 N TUBB STREET Oakland, FL MLS# O6362142
  • Virtual Tour
1 of 62
$1,650,000
6

Beds

7.1

Baths

5,614

Sq.Ft.

620 N TUBB STREET

Oakland, FL

Courtesy of OAKSTRAND REALTY
View 1210 JOHNS COVE LANE Oakland, FL MLS# O6384628
  • Recently Listed with Virtual Tour
1 of 75
$1,549,999
4

Beds

2.1

Baths

2,842

Sq.Ft.

1210 JOHNS COVE LANE

Oakland, FL

Courtesy of DALTON WADE INC
View 552 WALKER STREET Oakland, FL MLS# O6302798
$1,250,000
Studio

Beds

0.0

Baths

552 WALKER STREET

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 154 SOUTHERN RAILWAY 1 Oakland, FL MLS# O6300829
  • New Construction with Virtual Tour
1 of 11
$1,220,000
3,536

Sq.Ft.

154 SOUTHERN RAILWAY 1

Oakland, FL

Courtesy of THE MARKS GROUP REALTY, 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 1120 CIVITAS WAY Oakland, FL MLS# O6376905
$1,199,000
4

Beds

3.0

Baths

2,563

Sq.Ft.

1120 CIVITAS WAY

Oakland, FL

Courtesy of THE AGENCY FL
View 624 HULL ISLAND DRIVE Oakland, FL MLS# O6359887
  • Virtual Tour
1 of 25
$993,000
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 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
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 729 STRIHAL LOOP Oakland, FL MLS# O6381069
  • Recently Listed with Virtual Tour
1 of 49
$699,900
4

Beds

3.1

Baths

3,583

Sq.Ft.

729 STRIHAL LOOP

Oakland, FL

Courtesy of LIBERTY HOME SALES INC
View 2450 STANDING ROCK CIRCLE Oakland, FL MLS# O6360017
$695,000
5

Beds

4.0

Baths

3,163

Sq.Ft.

2450 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of PREMIER SOTHEBYS INT'L REALTY
View 2451 SKY STONE COURT Oakland, FL MLS# S5141292
  • Virtual Tour
1 of 27
OPEN HOUSE: Saturday 2/28 1:00 PM - 3:00 PM
$690,000
5

Beds

3.1

Baths

3,007

Sq.Ft.

2451 SKY STONE COURT

Oakland, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
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 2169 BAY LINE ROAD Oakland, FL MLS# O6379555
  • Virtual Tour
1 of 63
$665,000
4

Beds

3.0

Baths

2,274

Sq.Ft.

2169 BAY LINE ROAD

Oakland, FL

Courtesy of LPT REALTY, 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

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

45

Estimated median home price

$690,000
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

Price Count
$0 - 100K 1
$100K - 200K 0
$200K - 300K 0
$300K - 400K 3
$400K - 500K 8
$500K - 600K 4
$600K - 700K 10
$700K - 800K 1
$800K - 900K 2
$900K - 1M 1
$1M - Max 15

Homes for Sale by Type in Oakland, FL

Property Type Count
Single Family 31
Townhouse 2
Condo 0
Commercial 3
Rental 2
Lots and Land 9
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 2/28/2026)

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 2/28/2026.