42 total properties
Did you mean the neighborhood Oakland?
View 1507 WILD SWEETGRASS WAY Oakland, FL MLS# O6409105
  • Recently Listed with Virtual Tour
1 of 53
$565,000
3

Beds

2.0

Baths

1,975

Sq.Ft.

1507 WILD SWEETGRASS WAY

Oakland, FL

Courtesy of CORCORAN PREMIER REALTY
View 1108 RIVERWAY DRIVE Oakland, FL MLS# O6407380
  • Recently Listed
1 of 78
$1,025,000
5

Beds

3.0

Baths

2,999

Sq.Ft.

1108 RIVERWAY DRIVE

Oakland, FL

Courtesy of BHHS FLORIDA REALTY
View 100 W RAILWAY AVENUE Oakland, FL MLS# O6408609
  • New Construction with Virtual Tour
1 of 11
$2,186,921
3

Beds

4.2

Baths

3,555

Sq.Ft.

100 W RAILWAY AVENUE

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1216 HULL ISLAND DRIVE Oakland, FL MLS# G5112107
  • Recently Listed with Virtual Tour
1 of 82
$1,799,000
5

Beds

4.1

Baths

4,224

Sq.Ft.

1216 HULL ISLAND DRIVE

Oakland, FL

Courtesy of THE FLORIDA PROPERTY SHOP SALE
View 918 HULL ISLAND DRIVE Oakland, FL MLS# O6404554
$729,900
4

Beds

3.0

Baths

2,268

Sq.Ft.

918 HULL ISLAND DRIVE

Oakland, FL

Courtesy of BHHS FLORIDA REALTY
View 1137 PRADO LANE Oakland, FL MLS# O6402288
  • New Construction
1 of 4
$2,395,000
5

Beds

5.1

Baths

4,527

Sq.Ft.

1137 PRADO LANE

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 556 WALKER STREET Oakland, FL MLS# O6402404
  • Virtual Tour
1 of 5
$1,295,000
Studio

Beds

0.0

Baths

556 WALKER STREET

Oakland, FL

Courtesy of CORCORAN PREMIER REALTY
View 505 E GULLEY AVENUE Oakland, FL MLS# O6400317
  • Virtual Tour
1 of 78
$885,000
4

Beds

3.1

Baths

3,399

Sq.Ft.

505 E GULLEY AVENUE

Oakland, FL

Courtesy of CLOCK TOWER REALTY
View 2017 BOSS HEWETT STREET Oakland, FL MLS# O6402045
$749,900
4

Beds

4.0

Baths

2,852

Sq.Ft.

2017 BOSS HEWETT STREET

Oakland, FL

Courtesy of CHARLES RUTENBERG REALTY ORLANDO
View 219 LARGOVISTA DRIVE Oakland, FL MLS# O6401756
  • Virtual Tour
1 of 24
$1,099,000
5

Beds

4.0

Baths

3,951

Sq.Ft.

219 LARGOVISTA DRIVE

Oakland, FL

Courtesy of NOVARE REAL ESTATE LLC
View 2618 BOBCAT CHASE BOULEVARD Oakland, FL MLS# O6400122
$519,000
3

Beds

2.0

Baths

1,565

Sq.Ft.

2618 BOBCAT CHASE BOULEVARD

Oakland, FL

Courtesy of THE REAL ESTATE COLLECTION LLC
View 250 N WALKER STREET Oakland, FL MLS# G5110973
  • Virtual Tour
1 of 76
$1,145,000
4

Beds

2.1

Baths

2,469

Sq.Ft.

250 N WALKER STREET

Oakland, FL

Courtesy of COAST TO COAST REAL ESTATE PRO
View 1937 STANDING ROCK CIRCLE Oakland, FL MLS# O6398113
$515,000
3

Beds

2.1

Baths

2,069

Sq.Ft.

1937 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of REAL BROKER, LLC
View 15992 W COLONIAL DRIVE Oakland, FL MLS# O6395167
$3,200,000
41

Beds

75.0

Baths

17,021

Sq.Ft.

15992 W COLONIAL DRIVE

Oakland, FL

Courtesy of REMAX SUNSTATE REALTY
View 38 S POLLARD STREET Oakland, FL MLS# O6394442
  • New Construction with Virtual Tour
1 of 56
$659,999
4

Beds

2.1

Baths

1,872

Sq.Ft.

38 S POLLARD STREET

Oakland, FL

Courtesy of MS LAND & BUILDING LLC
View 812 JOHNS POINT DRIVE Oakland, FL MLS# O6393574
$2,750,000
5

Beds

6.0

Baths

4,373

Sq.Ft.

812 JOHNS POINT DRIVE

Oakland, FL

Courtesy of WRA BUSINESS & REAL ESTATE
View 2117 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6385739
$364,900
2

Beds

2.1

Baths

1,497

Sq.Ft.

2117 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of SERHANT
View 1231 FOLTZ LOOP Oakland, FL MLS# O6393970
  • 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
$875,000
4

Beds

3.0

Baths

2,850

Sq.Ft.

8 WINTERS LANDING DRIVE

Oakland, FL

Courtesy of REGENCY REAL ESTATE LLC
View 1412 JOHNS COVE LANE Oakland, FL MLS# O6391735
  • Virtual Tour
1 of 78
$1,499,000
4

Beds

4.1

Baths

3,613

Sq.Ft.

1412 JOHNS COVE LANE

Oakland, FL

Courtesy of NEXT RESIDENCE 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

42

Estimated median home price

$880,000
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

PriceCount
$0 - 100K0
$100K - 200K0
$200K - 300K0
$300K - 400K6
$400K - 500K1
$500K - 600K6
$600K - 700K2
$700K - 800K3
$800K - 900K5
$900K - 1M0
$1M - Max19

Homes for Sale by Type in Oakland, FL

Property TypeCount
Single Family29
Townhouse6
Condo0
Commercial1
Rental3
Lots and Land5
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 5/21/2026)

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 5/22/2026.