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 14 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 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 November 2025) reflects 52 homes changing hands, with an average asking price of $1,134,629 and an average selling price of $1,116,106. This represents a healthy list-to-sell price ratio of 98% and $290 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

315 Days

New Construction

Reduced

$1,795,000

$1,875,000

MLS#MFRO6339333

854 Tilden Oaks Trl
Winter Garden, FL 34787

5

5

2

3,991 SqFt

Pool

0.26 Acres

67 Days

Under Contract

$1,775,000

$1,975,000

MLS#MFRO6326350

1224 Union Club Dr
Winter Garden, FL 34787

5

6

3

7,426 SqFt

Water Front

0.3 Acres

112 Days

$1,700,000

MLS#MFRO6316643

1207 Ridge Lake Way
Oakland, FL 34787

5

4

3

5,609 SqFt

0.24 Acres

147 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

255 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

53 Days

Under Contract

$935,000

MLS#MFRO6352333

862 Oakland Park Blvd
Winter Garden, FL 34787

4

3

3

4,577 SqFt

0.22 Acres

16 Days

Reduced

$929,500

$989,500

MLS#MFRO6287898

985 Huntspoint St
Winter Garden, FL 34787

5

4

2

4,095 SqFt

0.13 Acres

228 Days

$880,000

MLS#MFRO6351976

1428 Union Club Dr
Winter Garden, FL 34787

4

4

2

3,542 SqFt

0.15 Acres

21 Days

Reduced

$850,000

$879,000

MLS#MFRG5100879

1368 Union Club Dr
Winter Garden, FL 34787

3

3

2

3,486 SqFt

0.24 Acres

72 Days

Reduced

$835,000

$999,900

MLS#MFRO6271175

931 Kylee Aly
Winter Garden, FL 34787

4

4

2

3,603 SqFt

0.07 Acres

277 Days

Under Contract

$835,000

$850,000

MLS#MFRO6322690

836 Gayle Mill Dr
Winter Garden, FL 34787

3

2

2

2,866 SqFt

Pool

0.24 Acres

111 Days

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14 Active Listings in Oakland Park