Neighborhood · Orlando, Florida
Chickasaw Trails
East Orlando living with room to breathe
2
Homes for sale
$457,500
Median list price
$236
Avg price / sqft
76
Median days on market
Chickasaw Trails sits in East Orlando, a settled residential pocket where the homes run to a comfortable mid-size — the median here is right around 1,957 square feet — and the pace is quieter than the tourist corridors to the south. You're about 20 minutes from both downtown Orlando and Orlando International Airport, which makes the day-to-day commute genuinely easy, while Universal is roughly a half hour out when you feel like a bigger outing. Compared with newer master-planned communities like Laureate Park or Eagle Creek, this is an established neighborhood with mature streets rather than a build-out.
For a buyer today, the market is thin and deliberate. There are just 2 active listings, with a median list price of $457,500, and homes are taking a while to move — median days on market sits at 75.5. Over the past year 10 homes sold at a median of $415,000, with sellers collecting about 98% of asking, so well-priced homes still trade close to list even in a patient market.
Chickasaw Trails is a community in Orlando, Florida.
Quick facts
$385,000 – $530K price range
1,957 sqft median home
$49/mo median HOA
10 sold in 12 months
Drive times
On the market now
Homes for sale in Chickasaw Trails
$530,000
3920 RUNNING WATER DRIVE, ORLANDO
4 bd · 2.5 ba · 2,366 sqft
$385,000
8818 RESERVATION DRIVE, ORLANDO
3 bd · 2 ba · 1,547 sqft
Every active listing inside the Chickasaw Trails boundary
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Browse Chickasaw Trails
Where the market lives
The numbers that matter
The Chickasaw Trails market
10
Sold, last 12 months
$415,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
24 days
Median time to sell
Chickasaw Trails vs Orlando
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Chickasaw Trails boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Chickasaw Trails is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Chickasaw Trails home
≈ $2,983/mo
$457,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$49/mo
Median HOA
From current listings inside the boundary
Population
1,119
Median age
41
Median income
$71,209
Median home value
$388,500
Beyond the listings
Living in Chickasaw Trails
Beliefs
Top 4% in the U.S.Spiritual Practices
Making it to church on Sunday, this population is drawn together by their devotion to, primarily Christian, religion. Common activities include worship services and bible studies.
Active
Top 7% in the U.S.Organized Sports
From tryouts and casual pick-up games, to varsity tournaments and intramural matches, this population includes people who participate in organized athletics. Often through schools or public recreational areas.
Food & Drink
Top 7% in the U.S.Fueling for Fitness
A population characterized by healthy eating. Often pre-planning for meals for the purpose of fitness and convenience. Likely to participate in meal prep trends.
Lifestyles
Top 8% in the U.S.Student Life
There's more to student life than academics. It's about the experience - from classes and homecoming, to making lifetime friends and alumni events. These are students at school, taking classes online, or finding other ways to be students in their daily lives.
Hobbies & Interests
Top 8% in the U.S.Green Thumb
From tiny sprouts and window plants, to flower arrangements and designing a landscape, this population has an affinity for all things green.
Beliefs
Top 9% in the U.S.Activism
This population seeks to advocate for a more just world. Common activities include protests, rallies, and spreading awareness to the public about social justice issues.
People who close here
Our Orlando experts
Straight answers
Chickasaw Trails FAQs
Is Chickasaw Trails a good place to live?+
It's a good fit if you want an established East Orlando neighborhood with an easy commute — downtown and the airport are each about 20 minutes away, and Universal is roughly 33 minutes. Homes here are family-scaled at around 1,957 square feet, and the area is zoned for Hidden Oaks Elementary, Liberty Middle, and Colonial High.
Is Chickasaw Trails expensive?+
It sits in the mid-range for the Orlando market, with a median list price of $457,500 and homes trading around $236 per square foot. The median sold price over the past year was $415,000, which is approachable relative to newer communities like Eagle Creek.
What do homes cost in Chickasaw Trails?+
Current active listings range from $385,000 to $530,000, with a median list price of $457,500. Over the last 12 months the 10 homes that sold came in at a median of $415,000, so buyers can expect to land somewhere in the $400,000s for a typical home.
How is the market right now?+
It's a low-inventory, patient market — only 2 homes are active, and the median time on market is 75.5 days. That said, sellers are still getting about 98% of asking, so pricing has stayed disciplined even with the slower pace.
What about HOA fees and property taxes?+
The median HOA runs a modest $49 per month, which is light compared with amenity-heavy communities like Laureate Park. Median annual property tax is about $3,768, in line with what you'd expect for homes in this price band.
Keep exploring
More Orlando neighborhoods
Neighborhood boundary by edgeAI; listings matched to the polygon. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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