Neighborhood · Orlando, Florida
Chickasaw Trails
East Orlando living with an easy airport commute
1
Homes for sale
$385,000
Median list price
$249
Avg price / sqft
47
Median days on market
Chickasaw Trails sits in east Orange County, where quiet residential streets put you about 20 minutes from both downtown and Orlando International Airport. It's a practical, low-key pocket of Orlando homes for sale — served by Hidden Oaks Elementary, Liberty Middle, and Colonial High — with the kind of central location that keeps commutes short whether you're heading to work, the airport, or out toward the theme parks. If you like the idea of a settled neighborhood rather than a master-planned enclave like Laureate Park, this is that.
The market here is tight and moves at a measured pace. There's just one active listing at $385,000, while 11 homes sold over the past year at a median of $425,000 — and sellers are collecting 98% of asking, so pricing has stayed disciplined. Buyers weighing this against nearby areas like Metro West or South Semoran will find Chickasaw Trails competitive on value with a friendlier HOA than most.
Chickasaw Trails is a community in Orlando, Florida.
Quick facts
$385,000 – $385K price range
1,547 sqft median home
$32/mo median HOA
$2,295/mo median rent
11 sold in 12 months
Drive times
On the market now
Homes for sale in Chickasaw Trails
Every active listing inside the Chickasaw Trails boundary
Open full map search →The numbers that matter
The Chickasaw Trails market
11
Sold, last 12 months
$425,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
26 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
≈ $2,573/mo
$385,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$32/mo
Median HOA
From current listings inside the boundary
$2,295/mo
Median rent
Homes for rent 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.
On the calendar
Near Chickasaw Trails
Jul
13
Mon
View of Oyster Bay
Explore the View of Oyster Bay, an artistic zenith of proficiency, emphasizing vibrant wisteria vines against serene bay backdrops. Discover stunning harmony as structure…
Jul
14
Tue
I Remember When...Reflections From The RMA Staff
This exhibition, curated by the staff of the Rollins Museum of Art, showcases a diverse range of media and themes, all centered around the concept of memory and storytell…
Jul
14
Tue
Being Outdoors
Celebrating the nation's 250th anniversary, the exhibition Being Outdoors delves into the deep-rooted connections between outdoor recreational activities and American ide…
Jul
14
Tue
Pathways
This exhibition, a collaboration between the Rollins Museum of Art and the UCF Art Gallery, showcases the diverse works of emerging Florida artists, handpicked by a panel…
Jul
14
Tue
The Captivating Unknown
The event, The Captivating Unknown, is an art exhibition that explores humanity's fascination with the cosmos through various artistic mediums. The works on display aim t…
Jul
16
Thu
Thursday Thinks Trivia
7:30pm
This challenging trivia night promises a wide range of engaging questions, ensuring something new and exciting for everyone - from pop culture, geography, and history, to…
People who close here
Our Orlando experts
Straight answers
Chickasaw Trails FAQs
Is Chickasaw Trails a good place to live?+
It's a settled east Orlando neighborhood with a strong location — about 20 minutes to both downtown and MCO, and 33 to Universal. Homes feed Hidden Oaks Elementary, Liberty Middle, and Colonial High, and the low $32/month median HOA keeps carrying costs down. It suits buyers who want central access without the price of a newer planned community like Laureate Park.
Is Chickasaw Trails expensive?+
It's mid-market for the Orlando area, with a median list price of $385,000 and homes selling around a $425,000 median over the past year. At roughly $249 per square foot on a typical 1,547-square-foot home, it lands below many west-side neighborhoods like Metro West.
What do homes cost in Chickasaw Trails?+
The single active listing is priced at $385,000, while the 11 homes sold over the past 12 months closed at a $425,000 median. Expect around $249 per square foot for a home near the typical 1,547-square-foot size.
How is the market in Chickasaw Trails?+
Inventory is very thin — just one home is active right now — and properties take a median of 47 days to sell. Sellers have been getting 98% of their asking price, so well-priced homes move without dramatic negotiation.
What are the HOA fees and property taxes like?+
The median HOA is only $32 a month, which is modest for the Orlando market. Median property taxes run about $3,636 a year, and if you're weighing renting first, the median rent in the area is around $2,295 a month.
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.
Never miss a listing
New Chickasaw Trails homes, in your inbox
A daily digest of new Orlando listings — straight from the MLS. Unsubscribe anytime.