Oakland Trails

Oakland Trails is a community of single family homes in Winter Garden, Florida, with a range of options priced between $474,990 and $796,000. There are currently a total of 6 homes for sale in Oakland Trails. The smallest Oakland Trails home presently available is a three bedroom two bathroom residence that is 2,855 square feet (2,078SF Under Air living space), and the largest of the Oakland Trails homes currently on the market has five beds and three baths and is a 4,682 square foot (3,528SF 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 Trails range from $105 to $399. This fee includes common area maintenance, grounds maintenance, building maintenance, the community pool, real estate taxes for common areas, trash removal, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Oakland Trails home.

Oakland Trails amenities include a clubhouse, and swimming pool. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

The Oakland Trails 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, and there is a restriction on pet size. Dogs and cats are allowed.

There are four commercial airports that serve Oakland Trails - Orlando Executive (ORL), which is nineteen miles away; Kissimmee Gateway (ISM), which is twenty two miles away; Orlando International (MCO), which is twenty three miles away, and Orlando Sanford International (SFB), which is 30 miles away from Oakland Trails.

Oakland Trails real estate activity on the Winter Garden MLS during the past year (as of April 2026) reflects seventeen homes changing hands, with an average asking price of $564,429 and an average selling price of $552,205. This represents a healthy list-to-sell price ratio of 98% and $164 per square foot. During this period, Oakland Trails homes for sale have taken an average of 77 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 Trails are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Oakland Trails 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 Trails Homes For Sale

Reduced

$796,000

$800,000

MLS#MFRO6361226

1970 Standing Rock Cir
Oakland, FL 34787

5

3

3

4,682 SqFt

0.2 Acres

152 Days

Under Contract

$625,000

$735,000

MLS#MFRS5141292

2451 Sky Stone Ct
Oakland, FL 34787

5

4

2

3,216 SqFt

0.17 Acres

102 Days

Under Contract

$574,000

$620,000

MLS#MFRS5141442

1490 Stone Arrow Ct
Winter Garden, FL 34787

5

4

3

4,016 SqFt

0.16 Acres

100 Days

Reduced

$549,900

$560,000

MLS#MFRO6379741

2065 White Feather Loop
Oakland, FL 34787

3

3

2

3,219 SqFt

0.09 Acres

74 Days

Reduced

$525,000

$545,000

MLS#MFRO6381627

2259 White Feather Loop
Oakland, FL 34787

4

3

2

2,866 SqFt

0.09 Acres

67 Days

Under Contract

$474,990

$494,000

MLS#MFRO6370898

2135 Standing Rock Cir
Oakland, FL 34787

3

3

2

2,855 SqFt

0.12 Acres

102 Days

6 Active Listings in Oakland Trails