23 total properties
Did you mean the neighborhood Oakland?
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 505 E GULLEY AVENUE Oakland, FL MLS# O6400317
  • Virtual Tour
1 of 78
$899,000
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 1051 STATIONSIDE DRIVE Oakland, FL MLS# O6398538
$489,000
4

Beds

3.0

Baths

2,120

Sq.Ft.

1051 STATIONSIDE DRIVE

Oakland, FL

Courtesy of CORCORAN PREMIER 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 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 2120 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6389691
$379,900
3

Beds

2.1

Baths

1,620

Sq.Ft.

2120 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of KELLER WILLIAMS ADVANTAGE III
View 1318 PAINTED BUNTING AVENUE Oakland, FL MLS# O6389319
$360,000
2

Beds

2.1

Baths

1,472

Sq.Ft.

1318 PAINTED BUNTING AVENUE

Oakland, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2222 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6389233
$416,900
3

Beds

3.0

Baths

1,809

Sq.Ft.

2222 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of LPT REALTY, LLC
View 2228 GOPHER TORTOISE TERRACE Oakland, FL MLS# G5109117
$395,000
3

Beds

2.1

Baths

1,620

Sq.Ft.

2228 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of ASANO REAL ESTATE LLC
View 1270 STATIONSIDE DRIVE DRIVE Oakland, FL MLS# O6376429
$519,000
4

Beds

2.0

Baths

2,046

Sq.Ft.

1270 STATIONSIDE DRIVE DRIVE

Oakland, FL

Courtesy of HOME INVEST REALTY INC
View 2259 WHITE FEATHER LOOP Oakland, FL MLS# O6381627
$525,000
4

Beds

2.1

Baths

2,204

Sq.Ft.

2259 WHITE FEATHER LOOP

Oakland, FL

Courtesy of YOUNG REAL ESTATE
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 2065 WHITE FEATHER LOOP Oakland, FL MLS# O6379741
$549,900
3

Beds

2.1

Baths

2,089

Sq.Ft.

2065 WHITE FEATHER LOOP

Oakland, FL

Courtesy of PINK MIAMI REAL ESTATE
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 2100 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6374216
$375,000
2

Beds

2.1

Baths

1,620

Sq.Ft.

2100 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of MARKET CONNECT REALTY LLC
View 624 HULL ISLAND DRIVE Oakland, FL MLS# O6359887
$849,000
4

Beds

2.0

Baths

2,708

Sq.Ft.

624 HULL ISLAND DRIVE

Oakland, FL

Courtesy of RE/MAX EXCLUSIVE COLLECTION

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

41

Estimated median home price

$875,000
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 - 500K2
$500K - 600K5
$600K - 700K2
$700K - 800K3
$800K - 900K5
$900K - 1M0
$1M - Max18

Homes for Sale by Type in Oakland, FL

Property TypeCount
Single Family28
Townhouse6
Condo0
Commercial1
Rental3
Lots and Land5
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 5/15/2026)

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 5/17/2026.