Trailside Station

Trailside Station is a community of single family homes in Oakland, Florida, with a range of options priced between $152,000 and $612,000. The smallest Trailside Station home in the community is a three bedroom two bathroom residence that is 2,235 square feet (1,759SF Under Air living space), and the largest of the Trailside Station homes has four beds and three baths and is a 3,224 square foot (2,627SF 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 Trailside Station range from $320 to $360. Please check the individual listing pages for the exact homeowners association fees for a particular Trailside Station home.

The Trailside Station HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

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

Trailside Station real estate activity on the Oakland MLS during the past year (as of September 2025) reflects that just one home changed hands during this time. Offered with an asking price of $419,900 and selling for $410,000, this represents a list/sell ratio of 98%. It took just 13 days from the time it was listed until it sold.

In addition, there are numerous other communities in Oakland to choose from, or you may browse all available Oakland Real Estate, including some new construction opportunities. Homes for sale in Trailside Station are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Trailside Station 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.

Trailside Station Homes For Sale

SOLD 08/03/15

$250,000

MLS#MFRO5374236

1250 Trailside Ct
Oakland, FL 34787

4

2

2

2,663 SqFt

Pool

0.32 Acres

SOLD 04/23/24

$495,000

MLS#MFRU8232929

1210 Trailside Ct
Oakland, FL 34787

4

2

2

2,840 SqFt

0.24 Acres

SOLD 04/27/23

$495,999

$540,000

MLS#MFRO6052695

1150 Trailside Ct
Oakland, FL 34787

3

2

2

2,284 SqFt

0.23 Acres

SOLD 12/12/14

$209,900

MLS#MFRS4805176

1110 Trailside Ct
Oakland, FL 34760

4

2

2,836 SqFt

Pool

0.23 Acres

SOLD 07/10/15

$217,000

MLS#MFRG4809854

1030 Trailside Ct
Oakland, FL 34787

4

2

2

2,628 SqFt

0.24 Acres

SOLD 04/12/24

$612,000

$628,000

MLS#MFRO6160671

1191 Trailside Ct
Oakland, FL 34787

4

3

2

3,224 SqFt

Pool

0.31 Acres

SOLD 05/15/12

$152,000

MLS#MFRO5053129

1071 Railside Way
Oakland, FL 34787

3

2

2

2,401 SqFt

Pool

0.25 Acres

SOLD 10/02/23

$495,990

MLS#MFRO6106984

1111 Railside Way
Oakland, FL 34787

4

3

2

2,873 SqFt

0.41 Acres

SOLD 02/07/25

$419,900

MLS#MFRO6262353

1171 Railside Way
Oakland, FL 34787

4

2

2

2,235 SqFt

0.23 Acres

SOLD 06/02/17

$259,900

MLS#MFRO5506074

1191 Railside Way Way
Oakland, FL 34787

4

3

2

2,969 SqFt

0.23 Acres

SOLD 08/07/17

$239,900

MLS#MFRO5517305

1151 Railside Way
Oakland, FL 34787

4

2

2

2,235 SqFt

0.23 Acres

SOLD 09/13/13

$210,000

MLS#MFRO5170515

1270 Stationside Dr
Oakland, FL 34787

4

2

2

2,487 SqFt

Pool

0.27 Acres

SOLD 03/25/22

$359,000

MLS#MFRG5052693

1071 Stationside Dr
Oakland, FL 34787

3

2

2

2,252 SqFt

0.22 Acres

SOLD 09/29/23

$489,900

$519,900

MLS#MFRO6121941

1271 Stationside Dr
Oakland, FL 34787

4

3

2

3,066 SqFt

0.24 Acres

SOLD 12/01/23

$549,000

MLS#MFRO6128307

1075 Stationside Dr
Oakland, FL 34787

4

2

2

3,067 SqFt

0.43 Acres

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We do not have any properties available for sale in Trailside Station.

0 Active Listings in Trailside Station