48 total properties
Did you mean the neighborhood Oakland?
View 510 BRILEY AVENUE Oakland, FL MLS# O6364796
  • New Construction with Virtual Tour
1 of 79
$3,575,000
5

Beds

5.2

Baths

5,478

Sq.Ft.

510 BRILEY AVENUE

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 312 BRILEY AVENUE Oakland, FL MLS# O6360845
  • New Construction
1 of 6
$2,995,000
6

Beds

6.1

Baths

5,144

Sq.Ft.

312 BRILEY AVENUE

Oakland, FL

Courtesy of CORCORAN PREMIER REALTY
View 320 S TUBB STREET Oakland, FL MLS# G5105639
  • Virtual Tour
1 of 38
$2,750,000
3,200

Sq.Ft.

320 S TUBB STREET

Oakland, FL

Courtesy of ARELLANO REALTY & INVESTMENTS
The time to sell is now! THE TIME TO SELL IS NOW!
View 1118 SARAH MATHEWS DRIVE Oakland, FL MLS# O6371802
  • New Construction with Virtual Tour
1 of 66
$2,300,000
4

Beds

4.2

Baths

3,902

Sq.Ft.

1118 SARAH MATHEWS DRIVE

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 1173 PRADO LANE Oakland, FL MLS# O6359359
  • New Construction with Virtual Tour
1 of 17
$2,238,120
5

Beds

5.1

Baths

4,204

Sq.Ft.

1173 PRADO LANE

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 1017 JOHNS POINT DRIVE Oakland, FL MLS# O6363950
$2,160,000
5

Beds

6.0

Baths

6,141

Sq.Ft.

1017 JOHNS POINT DRIVE

Oakland, FL

Courtesy of BAY STREET GROUP FLORIDA LLC
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
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 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 101 N STARR STREET Oakland, FL MLS# O6323162
$1,450,000
3

Beds

3.1

Baths

2,502

Sq.Ft.

101 N STARR STREET

Oakland, FL

Courtesy of BHHS FLORIDA REALTY
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 7
$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
$1,000,000
4

Beds

2.0

Baths

2,708

Sq.Ft.

624 HULL ISLAND DRIVE

Oakland, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION
View 1185 WILDER OAKS WAY Oakland, FL MLS# O6373302
$995,000
4

Beds

3.1

Baths

2,789

Sq.Ft.

1185 WILDER OAKS WAY

Oakland, FL

Courtesy of THE AGENCY FL
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 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
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

PriceCount
$0 - 100K1
$100K - 200K0
$200K - 300K0
$300K - 400K5
$400K - 500K9
$500K - 600K2
$600K - 700K8
$700K - 800K3
$800K - 900K3
$900K - 1M2
$1M - Max15

Homes for Sale by Type in Oakland, FL

Property TypeCount
Single Family32
Townhouse2
Condo0
Commercial3
Rental3
Lots and Land11
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(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 2/9/2026.