Longleaf Oakland

Longleaf is a community of single family homes, and townhomes in Oakland, Florida, with a range of options priced between $375,000 and $660,000. There are currently a total of 5 homes for sale in Longleaf. The smallest Longleaf home presently available is a three bedroom two bathroom residence that is 1,811 square feet (1,554SF Under Air living space), and the largest of the Longleaf homes currently on the market has three beds and two baths and is a 3,957 square foot (3,053SF 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 Longleaf are $276 and $402 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, the community pool, trash removal, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Longleaf home.

Longleaf amenities include a swimming pool. There is also a community park, a playground, as well as walking or jogging trails.

The Longleaf 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 Longleaf - Orlando Executive (ORL), which is eighteen 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 Longleaf.

Longleaf real estate activity on the Oakland MLS during the past year (as of September 2025) reflects ten homes changing hands, with an average asking price of $500,190 and an average selling price of $490,530. This represents a healthy list-to-sell price ratio of 98% and $180 per square foot. During this period, Longleaf homes for sale have taken an average of 71 days to sell.

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 Longleaf are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Longleaf 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.

Longleaf Homes For Sale

Under Contract

$599,900

$615,000

MLS#1055152

2642 Bobcat Chase Blvd
Oakland, FL 34787

3

3

2

2,677 SqFt

Pool

0.12 Acres

40 Days

Reduced

$514,913

$529,500

MLS#MFRG5098929

2755 Bobcat Chase Blvd
Oakland, FL 34787

3

3

2

2,585 SqFt

0.11 Acres

91 Days

Under Contract

$510,000

MLS#MFRG5101412

1143 Bobcat Chase Blvd
Oakland, FL 34787

3

3

2

2,677 SqFt

0.11 Acres

33 Days

Reduced

$390,000

$398,500

MLS#MFRG5099743

2120 Gopher Tortoise Ter
Oakland, FL 34787

3

3

2

2,275 SqFt

0.05 Acres

74 Days

$375,000

MLS#MFRO6342825

2217 Gopher Tortoise Ter
Oakland, FL 34787

2

3

2

2,095 SqFt

0.05 Acres

15 Days

You may also be interested in Longleaf in Melbourne, Longleaf in New Port Richey or Longleaf in Gainesville.

5 Active Listings in Longleaf