Oakland Park Winter Garden

Oakland Park is a community of single family homes in Winter Garden, Florida, with a range of options priced between $780,000 and $1,996,500. There are currently a total of 15 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 six beds and five baths and is a 7,426 square foot (5,441SF 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 $601 to $1,179. 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 September 2025) reflects 53 homes changing hands, with an average asking price of $1,087,606 and an average selling price of $1,070,284. This represents a healthy list-to-sell price ratio of 98% and $291 per square foot. During this period, Oakland Park homes for sale have taken an average of 59 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

$1,996,500

MLS#MFRO6265275

1258 Ridge Lake Way
Oakland, FL 34787

4

4

3

6,280 SqFt

0.25 Acres

268 Days

New Construction

$1,949,000

MLS#MFRO6337279

1020 Tildenville School Rd
Winter Garden, FL 34787

5

5

3

5,687 SqFt

Pool

0.35 Acres

26 Days

New Construction

Reduced

$1,895,000

$1,950,000

MLS#MFRO6332237

958 Tildenville School Rd
Winter Garden, FL 34787

5

5

2

5,533 SqFt

Pool

0.35 Acres

48 Days

New Construction

$1,875,000

MLS#MFRO6339333

854 Tilden Oaks Trl
Winter Garden, FL 34787

5

5

2

3,991 SqFt

Pool

0.26 Acres

20 Days

Reduced

$1,850,000

$1,975,000

MLS#MFRO6326350

1224 Union Club Dr
Winter Garden, FL 34787

5

6

3

7,426 SqFt

Water Front

0.3 Acres

65 Days

$1,800,000

MLS#MFRO6318303

102 Hammock Preserve Loop
Winter Garden, FL 34787

6

5

2

5,597 SqFt

Pool

0.22 Acres

93 Days

New Construction

$1,700,000

MLS#MFRO6316643

1207 Ridge Lake Way
Oakland, FL 34787

5

4

3

5,609 SqFt

0.24 Acres

100 Days

New Construction

$1,675,000

MLS#MFRO6283425

166 Hammock Preserve Loop
Winter Garden, FL 34787

4

4

3

5,283 SqFt

0.16 Acres

208 Days

New Construction

$1,050,000

MLS#MFRO6343042

877 Tilden Oaks Trl
Winter Garden, FL 34787

5

4

2

4,193 SqFt

0.18 Acres

6 Days

Reduced

$935,000

$989,500

MLS#MFRO6287898

985 Huntspoint St
Winter Garden, FL 34787

5

4

2

4,095 SqFt

0.13 Acres

181 Days

Reduced

$899,000

$999,900

MLS#MFRO6271175

931 Kylee Aly
Winter Garden, FL 34787

4

4

2

3,603 SqFt

0.07 Acres

230 Days

Reduced

$874,000

$879,000

MLS#MFRG5100879

1368 Union Club Dr
Winter Garden, FL 34787

3

3

2

3,486 SqFt

0.24 Acres

25 Days

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15 Active Listings in Oakland Park