Oakland Park Winter Garden

Oakland Park is a community of single family homes in Winter Garden, Florida, with a range of options priced between $795,900 and $1,998,000. There are currently a total of 11 homes for sale in Oakland Park. The smallest Oakland Park home presently available is a three bedroom two bathroom residence that is 2,830 square feet (1,932SF Under Air living space), and the largest of the Oakland Park homes currently on the market has five beds and four baths and is a 6,309 square foot (4,557SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Oakland Park range from $202 to $1,202. This fee includes common area maintenance, grounds maintenance, building maintenance, the community pool, real estate taxes for common areas, property insurance, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Oakland Park home.

Oakland Park amenities include a clubhouse, swimming pool, and a state-of-the-art fitness center. Sports facilities include pickleball courts. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

The Oakland Park HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have. Dogs and cats are allowed.

There are four commercial airports that serve Oakland Park - Orlando Executive (ORL), which is seventeen miles away; Orlando International (MCO), which is twenty one miles away; Kissimmee Gateway (ISM), which is twenty two miles away, and Orlando Sanford International (SFB), which is twenty eight miles away from Oakland Park.

Oakland Park real estate activity on the Winter Garden MLS during the past year (as of March 2026) reflects 52 homes changing hands, with an average asking price of $1,186,133 and an average selling price of $1,159,281. This represents a healthy list-to-sell price ratio of 98% and $276 per square foot. During this period, Oakland Park homes for sale have taken an average of 49 days to sell.

In addition, there are numerous other communities in Winter Garden to choose from, or you may browse all available Winter Garden Real Estate, including some new construction opportunities. Homes for sale in Oakland Park are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Oakland Park hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Oakland Park Homes For Sale

$1,998,000

MLS#MFRO6373776

1258 Ridge Lake Way
Oakland, FL 34787

4

4

3

6,280 SqFt

0.25 Acres

64 Days

New Construction

$1,899,000

MLS#MFRO6387519

720 Lake Brim Dr
Winter Garden, FL 34787

4

4

2

5,626 SqFt

Pool

0.21 Acres

14 Days

Under Contract

$1,850,000

MLS#MFRO6386910

15198 E Oakland Ave
Winter Garden, FL 34787

4

4

3

5,294 SqFt

Pool

0.37 Acres

16 Days

Reduced

$1,785,000

$1,809,000

MLS#MFRG5107489

906 Allendale Ln
Winter Garden, FL 34787

4

4

3

5,263 SqFt

0.18 Acres

47 Days

$1,700,000

MLS#MFRO6316643

1207 Ridge Lake Way
Oakland, FL 34787

5

4

3

5,609 SqFt

0.24 Acres

284 Days

New Construction

Reduced

$1,275,000

$1,299,999

MLS#MFRO6385496

1156 Civitas Way
Oakland, FL 34787

4

3

3

6,309 SqFt

0.14 Acres

23 Days

Under Contract

$1 Million

MLS#MFRO6385538

1045 Colleton Aly
Winter Garden, FL 34787

4

4

2

3,861 SqFt

0.15 Acres

22 Days

$995,000

MLS#MFRO6388775

744 Lake Brim Dr
Winter Garden, FL 34787

4

4

2

3,948 SqFt

0.15 Acres

10 Days

$875,000

MLS#MFRO6387922

931 Kylee Aly
Winter Garden, FL 34787

4

4

2

3,603 SqFt

0.07 Acres

15 Days

Under Contract

$875,000

MLS#MFRO6383325

855 Oakland Park Blvd
Winter Garden, FL 34787

4

3

2

3,566 SqFt

0.16 Acres

30 Days

Under Contract

$800,000

MLS#MFRO6379734

1087 Huntspoint St
Winter Garden, FL 34787

3

2

2

2,830 SqFt

0.13 Acres

43 Days

You may also be interested in Oakland Park in Port Orange.

11 Active Listings in Oakland Park