Chickasaw Oaks

Chickasaw Oaks is a community of single family homes in Orlando, Florida, with a range of options priced between $355,900 and $460,000. There are currently a total of 11 homes for sale in Chickasaw Oaks. The smallest Chickasaw Oaks home presently available is a three bedroom two bathroom residence that is 1,589 square feet (1,240SF Under Air living space), and the largest of the Chickasaw Oaks homes currently on the market has four beds and two baths and is a 2,488 square foot (2,025SF 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 Chickasaw Oaks range from $110 to $243. This fee includes real estate taxes for common areas. Please check the individual listing pages for the exact homeowners association fees for a particular Chickasaw Oaks home.

The Chickasaw Oaks HOA rules do allow homeowners to have pets. Dogs and cats are allowed.

There are four commercial airports that serve Chickasaw Oaks - Orlando International (MCO), which is five miles away; Orlando Executive (ORL), which is six miles away; Kissimmee Gateway (ISM), which is seventeen miles away, and Orlando Sanford International (SFB), which is twenty miles away from Chickasaw Oaks.

Chickasaw Oaks real estate activity on the Orlando MLS during the past year (as of March 2026) reflects thirteen homes changing hands, with an average asking price of $361,619 and an average selling price of $354,492. This represents a healthy list-to-sell price ratio of 98% and $200 per square foot. During this period, Chickasaw Oaks homes for sale have taken an average of 55 days to sell.

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

Chickasaw Oaks Homes For Sale

Under Contract

$460,000

$470,000

MLS#MFRO6351003

5078 Loblolly Bay Ln
Orlando, FL 32829

3

2

2

2,488 SqFt

0.18 Acres

150 Days

Under Contract

$440,000

MLS#MFRO6377891

8750 Brackenwood Dr
Orlando, FL 32829

3

2

2

2,013 SqFt

Pool

0.22 Acres

42 Days

Under Contract

$425,000

MLS#MFRO6379439

8644 Lyonia Dr
Orlando, FL 32825

4

2

2

2,071 SqFt

Pool

0.25 Acres

49 Days

$425,000

MLS#MFRS5145852

8509 Lyonia Dr
Orlando, FL 32829

4

2

10,920 SqFt

0.25 Acres

5 Days

$420,000

MLS#MFRS5145480

8713 Catbriar Bay Way
Orlando, FL 32829

3

3

2

2,136 SqFt

0.21 Acres

15 Days

Under Contract

$410,000

MLS#MFRO6383721

4319 Saddle Creek Pl
Orlando, FL 32829

3

2

2

2,260 SqFt

0.19 Acres

34 Days

Under Contract

$380,000

$410,000

MLS#MFRO6370274

4803 Hopespring Dr
Orlando, FL 32829

4

2

2

1,951 SqFt

Pool

0.51 Acres

85 Days

Under Contract

$375,000

MLS#MFRO6383860

8619 Catbriar Ln
Orlando, FL 32829

4

2

2

1,711 SqFt

Pool

0.58 Acres

32 Days

Reduced

$365,000

$384,900

MLS#MFRS5138242

8755 Catbriar Bay Way
Orlando, FL 32829

3

3

2

2,136 SqFt

0.17 Acres

134 Days

$355,900

MLS#MFRO6366980

4814 Myrtle Bay Dr
Orlando, FL 32829

3

2

2

1,950 SqFt

0.18 Acres

99 Days

Under Contract

$355,000

MLS#MFRG5109354

4627 Saddle Creek Pl
Orlando, FL 32829

4

2

2

2,038 SqFt

0.19 Acres

17 Days

11 Active Listings in Chickasaw Oaks