23 total properties
Did you mean the neighborhood Oakland?
View 2618 BOBCAT CHASE BOULEVARD Oakland, FL MLS# O6400122
  • Recently Listed with Virtual Tour
1 of 61
OPEN HOUSE: Sunday 4/26 11:00 AM - 2:00 PM
$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 2117 GOPHER TORTOISE TERRACE Oakland, FL MLS# O6385739
$364,900
2

Beds

2.1

Baths

1,472

Sq.Ft.

2117 GOPHER TORTOISE TERRACE

Oakland, FL

Courtesy of SERHANT
The time to sell is now! THE TIME TO SELL IS NOW!
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
$370,000
2

Beds

2.1

Baths

1,472

Sq.Ft.

1318 PAINTED BUNTING AVENUE

Oakland, FL

Courtesy of RE/MAX TOWN & COUNTRY REALTY
View 2660 BOBCAT CHASE BOULEVARD Oakland, FL MLS# G5109325
  • Adult Community with Virtual Tour
1 of 30
$525,000
3

Beds

2.1

Baths

1,811

Sq.Ft.

2660 BOBCAT CHASE BOULEVARD

Oakland, FL

Courtesy of KELLER WILLIAMS ELITE PARTNERS III 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 406 W HERRIOTT AVENUE Oakland, FL MLS# S5145432
$97,000
Studio

Beds

0.0

Baths

406 W HERRIOTT AVENUE

Oakland, FL

Courtesy of V PROPERTIES INC
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 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
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 1227 RIDGE LAKE WAY Oakland, FL MLS# O6376717
$455,000
Studio

Beds

0.0

Baths

1227 RIDGE LAKE WAY

Oakland, FL

Courtesy of THE C SMITH REAL ESTATE GROUP LLC
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 2135 STANDING ROCK CIRCLE Oakland, FL MLS# O6370898
$474,990
3

Beds

2.1

Baths

2,078

Sq.Ft.

2135 STANDING ROCK CIRCLE

Oakland, FL

Courtesy of KELLER WILLIAMS WINTER PARK
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
View 121 S NIXON STREET Oakland, FL MLS# O6352916
$70,000
Studio

Beds

0.0

Baths

121 S NIXON STREET

Oakland, FL

Courtesy of SANCTUM REALTY PROFESSIONALS LLC
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 514 N POLLARD STREET Oakland, FL MLS# O6332783
$575,000
Studio

Beds

0.0

Baths

514 N POLLARD STREET

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

44

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 - 500K6
$500K - 600K6
$600K - 700K5
$700K - 800K1
$800K - 900K4
$900K - 1M0
$1M - Max14

Homes for Sale by Type in Oakland, FL

Property TypeCount
Single Family27
Townhouse6
Condo0
Commercial1
Rental2
Lots and Land9
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms0

(Data as of 4/24/2026)

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 4/24/2026.