Oakland Trails

Oakland Trails is a community of single family homes in Winter Garden, Florida, with a range of options priced between $455,000 and $800,000. There are currently a total of 8 homes for sale in Oakland Trails. The smallest Oakland Trails home presently available is a three bedroom two bathroom residence that is 2,089 square feet (2,010SF Under Air living space), and the largest of the Oakland Trails homes currently on the market has five beds and four 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 $310 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 December 2025) reflects twelve homes changing hands, with an average asking price of $549,365 and an average selling price of $537,833. This represents a healthy list-to-sell price ratio of 98% and $160 per square foot. During this period, Oakland Trails homes for sale have taken an average of 71 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

$800,000

MLS#MFRO6361226

1970 Standing Rock Cir
Oakland, FL 34787

5

3

3

4,682 SqFt

0.2 Acres

16 Days

Under Contract

$749,000

MLS#MFRO6355588

1751 Standing Rock Cir
Oakland, FL 34787

5

3

3

4,590 SqFt

0.18 Acres

38 Days

$714,500

MLS#MFRO6360017

2450 Standing Rock Cir
Oakland, FL 34787

5

4

2

4,175 SqFt

0.17 Acres

21 Days

Reduced

$585,000

$649,900

MLS#MFRO6335263

2090 Standing Rock Cir
Oakland, FL 34787

3

3

2

3,000 SqFt

0.17 Acres

115 Days

Under Contract

$525,000

$560,000

MLS#MFRO6317013

1787 White Feather Loop
Oakland, FL 34787

3

3

2

3,227 SqFt

0.09 Acres

178 Days

$525,000

MLS#MFRO6333932

2375 Standing Rock Cir
Oakland, FL 34787

3

3

2

3,235 SqFt

0.09 Acres

121 Days

Reduced

$475,500

$545,000

MLS#MFRO6325992

2435 Standing Rock Cir
Oakland, FL 34787

4

3

2

2,640 SqFt

0.09 Acres

148 Days

Under Contract

$455,000

$485,000

MLS#MFRO6331070

2023 White Feather Loop
Oakland, FL 34787

3

3

2

2,089 SqFt

0.09 Acres

130 Days

8 Active Listings in Oakland Trails