Oakland Real Estate

Some of the best housing options in Orange County are in the Oakland Real Estate market, with a variety of single family homes for sale priced between $367,500 and as high as $2,500,000 three to six bedroom homes that range in size from 1,641 to 12,705 square feet.

We have detailed information regarding 7 communities in Oakland, including five non-gated communities of single family homes, and two waterfront communities including some new construction opportunities and open houses. Oakland real estate activity on the MLS indicates 34 properties are currently on the market (as of September 27th, 2025). Whether relocating to Oakland from another state or upsizing or downsizing, whichever of the many homes for sale in Oakland and the entire Central Florida region you choose, our professional Realtors in Oakland Florida can guide you through the home-buying process.

Oakland Homes For Sale

$2.5 Million

Johns Landing

530 Largovista Dr
Oakland, FL 34787

5

5

3

6,172 SqFt

Pool

Water Front

0.56 Acres

74 Days

$2,295,000

MLS#MFRO6296402

1244 Water Maple Dr
Oakland, FL 34787

6

6

2

6,352 SqFt

Pool

0.24 Acres

175 Days

New Construction

$2,175,000

MLS#MFRO6296458

1232 Water Maple Dr
Oakland, FL 34787

5

8

2

6,071 SqFt

Pool

0.25 Acres

175 Days

New Construction

$2,150,000

MLS#MFRO6296225

1238 Water Maple Dr
Oakland, FL 34787

5

6

2

5,446 SqFt

Pool

0.26 Acres

175 Days

New Construction

$1,996,500

Oakland Park

1258 Ridge Lake Way
Oakland, FL 34787

4

4

3

6,280 SqFt

0.25 Acres

278 Days

New Construction

$1,975,000

MLS#MFRO6295799

1149 Prado Lane Dr
Oakland, FL 34787

5

6

2

5,911 SqFt

Pool

0.24 Acres

175 Days

New Construction

$1,700,000

Oakland Park

1207 Ridge Lake Way
Oakland, FL 34787

5

4

3

5,609 SqFt

0.24 Acres

110 Days

New Construction

Under Contract

$1,649,990

Johns Cove

812 Johns Point Dr
Oakland, FL 34787

5

4

3

5,621 SqFt

Pool

Water Front

0.57 Acres

39 Days

$1,450,000

MLS#MFRO6323162

101 N Starr St
Oakland, FL 34760

3

4

3

4,082 SqFt

Pool

0.39 Acres

70 Days

Under Contract

$749,000

$760,000

Oakland Trails

2340 Standing Rock Cir
Oakland, FL 34787

5

3

3

4,609 SqFt

0.19 Acres

114 Days

Reduced

$729,999

$825,000

Johns Cove

1301 Johns Cove Ln
Oakland, FL 34787

4

2

2

12,705 SqFt

Pool

0.29 Acres

117 Days

$728,000

Johns Landing

729 Strihal Loop
Oakland, FL 34787

5

4

2

3,583 SqFt

Pool

0.24 Acres

42 Days

34 Active Listings in Oakland, FL

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Living in Oakland affords you easy access to nearby golf courses, fine dining, entertainment venues and various other amenities and conveniences in the city of Oakland. The I-4 or Florida's Turnpike provide an easy transition to nearby cities such as Montverde, Winter Haven, Ocoee, Gotha, Mascotte, Apopka, Windermere, Ocala, Astatula, Howey In The Hills, Mount Dora, Zellwood, Auburndale, Groveland, and Labelle.

Boating and watersports are integral to the Central Florida lifestyle, offering year-round access to an abundance of lakes, vibrant marine life, and a culture centered around outdoor leisure and recreation. Oakland real estate prices are directly correlated to it's proximity to these amenities.

Additionally, four local airports are easily accessible - Orlando Executive (ORL), Kissimmee Gateway (ISM) in Orlando, Orlando International (MCO), and Orlando Sanford International (SFB). Finally, for private air travel, you may utilize Leesburg International (LEE).

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.