Chickasaw Oaks

Chickasaw Oaks is a community of single family homes in Orlando, Florida, with a range of options priced between $355,000 and $420,000. There are currently a total of 7 homes for sale in Chickasaw Oaks. The smallest Chickasaw Oaks home presently available is a three bedroom two bathroom residence that is 1,950 square feet (1,343SF 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 10,920 square foot (1,704SF 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 $100 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 May 2026) reflects nineteen homes changing hands, with an average asking price of $377,161 and an average selling price of $371,547. This represents a healthy list-to-sell price ratio of 99% and $198 per square foot. During this period, Chickasaw Oaks homes for sale have taken an average of 47 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

$420,000

MLS#MFRS5145480

8713 Catbriar Bay Way
Orlando, FL 32829

3

3

2

2,136 SqFt

0.21 Acres

58 Days

Reduced

$414,900

$425,000

MLS#MFRS5145852

8509 Lyonia Dr
Orlando, FL 32829

4

2

10,920 SqFt

0.25 Acres

48 Days

Under Contract

$400,000

MLS#MFRO6395910

8619 Paola Ct
Orlando, FL 32829

4

3

2

2,268 SqFt

0.25 Acres

24 Days

Under Contract

$386,000

$410,000

MLS#MFRO6370274

4803 Hopespring Dr
Orlando, FL 32829

4

2

2

1,951 SqFt

Pool

0.51 Acres

128 Days

Under Contract

$369,987

MLS#MFRS5148571

8742 Brackenwood Dr
Orlando, FL 32829

3

2

1

1,532 SqFt

0.22 Acres

10 Days

Under Contract

$355,900

MLS#MFRO6366980

4814 Myrtle Bay Dr
Orlando, FL 32829

3

2

2

1,950 SqFt

0.18 Acres

142 Days

Reduced

$355,000

$384,900

MLS#MFRS5138242

8755 Catbriar Bay Way
Orlando, FL 32829

3

3

2

2,136 SqFt

0.17 Acres

177 Days

7 Active Listings in Chickasaw Oaks