Chickasaw Oaks

Chickasaw Oaks is a community of single family homes in Orlando, Florida, with a range of options priced between $370,000 and $475,000. 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 1,225 square feet, and the largest of the Chickasaw Oaks homes currently on the market has four beds and two baths and is a 2,454 square foot (1,941SF 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 $65 to $227. 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 September 2025) reflects fourteen homes changing hands, with an average asking price of $382,261 and an average selling price of $374,786. This represents a healthy list-to-sell price ratio of 98% and $180 per square foot. During this period, Chickasaw Oaks homes for sale have taken an average of 37 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

$475,000

MLS#MFRO6343366

8620 Crossbay Dr
Orlando, FL 32829

4

2

2

2,454 SqFt

0.31 Acres

4 Days

$415,000

MLS#MFRO6347232

4701 Saddle Creek Pl
Orlando, FL 32829

3

2

2

2,119 SqFt

0.22 Acres

1 Days

$403,000

MLS#MFRS5118657

4749 Hopespring Dr
Orlando, FL 32829

3

2

2

2,089 SqFt

0.7 Acres

227 Days

Reduced

$380,000

$390,000

MLS#MFRO6314136

8767 Grandee Dr
Orlando, FL 32829

3

2

2

1,741 SqFt

0.17 Acres

106 Days

Under Contract

$379,900

MLS#MFRTB8427614

4800 Reginald Rd
Orlando, FL 32829

3

2

2

1,225 SqFt

0.21 Acres

12 Days

Reduced

$370,000

$402,000

MLS#MFRS5127449

4926 Reginald Rd
Orlando, FL 32829

4

2

2

1,883 SqFt

0.17 Acres

124 Days

$345,000

MLS#MFRO6345278

4784 Crossbow Ct
Orlando, FL 32829

2

2

1

1,020 SqFt

0.24 Acres

1 Days

7 Active Listings in Chickasaw Oaks