Chickasaw Oaks is a family-friendly residential community in the desirable area of Southeast Orlando, Florida. Minutes away from Orlando International Airport and vibrant city life, the charming neighborhood enjoys the best of suburban living close to metropolitan conveniences.

Chickasaw Oaks Homes for Sale

New

8704 Gopher Lane

$360,000

ORLANDO

MLS® # O6201313

3 Beds, 2 Baths, 1,104 Sf

New

8588 Lyonia Drive

$425,000

ORLANDO

MLS® # O6200097

3 Beds, 2 Baths, 1,582 Sf

8750 Brackenwood Drive

$419,990

ORLANDO

MLS® # O6196795

3 Beds, 2 Baths, 1,428 Sf

Reduced 90%

4812 Hopespring Drive

$315,000

ORLANDO

MLS® # O6190678

3 Beds, 2 Baths, 1,240 Sf

Reduced 2.3%

4878 Red Bay Drive

$429,900

ORLANDO

MLS® # O6193135

3 Beds, 3 Baths, 1,662 Sf

Pending

4915 Holly Bay Way

$455,000

ORLANDO

MLS® # O6188475

4 Beds, 2 Baths, 2,074 Sf

Pending

4869 Myrtle Bay Drive

$375,000

ORLANDO

MLS® # O6172146

3 Beds, 2 Baths, 1,248 Sf

Pending

4909 Reginald Road

$405,000

ORLANDO

MLS® # S5095841

3 Beds, 2 Baths, 1,300 Sf

Built between the 1980s to mid-1990s, Chickasaw Oaks features an assortment of midsize homes and various architectural styles. The Orange County neighborhood boasts multiple tree-lined streets, manicured lawns, and plenty of lush, green space.

Various floorplans feature 2-4 bedrooms, 2-3 bathrooms, attached garages, and 1200-1300 sq ft of living space. Many of the homes feature modern upgrades, gourmet kitchens, large owners' suites, and updated appliances. Additionally, many of the properties also feature screened-in pools and private lanais.

Located at the intersection of S. Chickasaw Trail and Red Bay Drive, residents enjoy easy access to major roadways and Orlando's best offerings. The subdivision is easily accessible to the 408 Expressway, State Roads 528, 417, and I-4. In addition, daily necessities, including top-rated hospitals, Orange County schools, groceries, and more, are located within a 10-mile radius. As a result, everyday living is a breeze.

Residents love the excellent proximity to Lake Nona, Waterford Lakes, downtown Orlando and more. Enjoy decadent dining or shopping in Lake Nona or Thornton Park. Experience a musical at the Dr. Phillips Center for the Performing Arts or a game at Amway Arena. And take advantage of the easy drives to Walt Disney World, Universal Orlando Resort, and SeaWorld.

Find your perfect home at Chickasaw Oaks!

Chickasaw Oaks Community Information

Location: S. Chickasaw Trail and Red Bay Drive 
Year(s) Built: 2007-2021
HOA: Yes
Square Footage: 1,200 - 1,300 
Community Amenities: Trails

Orange County Public Schools

• Hidden Oaks Elementary School: Grades Pre-K - 5th Distance: 1 mile
• Odyssey Middle School: Grades 6-8 Distance: 3 miles
• Colonial High School: Grades 9th - 12th Distance: 7 miles

Dining and Shopping

• Vista Lakes Center with Publix Grocery- Distance: 2 miles
• Waterford Lakes Town Center-Distance: 10 miles
• Restaurant Row- Distance: 20 miles
• Lake Nona Town Center - Distance: 10 miles
• SODO- Distance: 12 miles
• Thornton Park-Distance: 10 miles
• The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance: 15 miles
• Downtown Orlando - Distance: 10 miles

Parks and Recreation

• Dr. Phillips Center for the Performing Arts - Distance: 10 miles
• Amway Center - Distance: 10 miles
• Walt Disney World Resort - Distance :22 miles
• Lake Eola Park - Distance: 10 miles
• Ventura Country Club Golf Club - Distance: 3 miles
• RDV Sports Complex - Distance: 20 miles
• Lake Nona YMCA Family Center - Distance: 7 miles

Hospitals

• AdventHealth East Orlando Hospital - Distance: 5 miles

*Distances are approximately measured from the Chickasaw Oaks community entrance.