Neighborhood · Orlando, Florida
Chickasaw Trails
East Orlando living with an easy commute
3
Homes for sale
$370,000
Median list price
$221
Avg price / sqft
20
Median days on market
Chickasaw Trails sits in east Orange County, close enough to the action but with the calmer rhythm of an established residential neighborhood. You're about 20 minutes from both downtown Orlando homes for sale and Orlando International Airport, with Universal Orlando roughly 33 minutes away and Walt Disney World about 45 — the kind of central positioning that makes weekday commutes and weekend outings equally manageable. Homes here feed into Colonial High, Liberty Middle, and Hidden Oaks Elementary.
For buyers, this is a quiet, low-inventory pocket. There's currently just one active listing at $375,000, while the twelve homes sold over the past year closed at a median of $420,000 — a gap worth understanding before you write an offer. Sellers have been getting about 97% of asking, so well-priced homes still move, but the median 171 days on market tells you this isn't a frantic bidding-war zone. Compared with nearby communities like Hunters Creek or Metro West, it's a more understated corner of Orlando.
Chickasaw Trails is a community in Orlando, Florida.
Quick facts
$365,000 – $525K price range
1,547 sqft median home
$32/mo median HOA
$2,200/mo median rent
10 sold in 12 months
Drive times
On the market now
Homes for sale in Chickasaw Trails
$524,999
3785 PEACE PIPE DRIVE, ORLANDO
5 bd · 3 ba · 3,103 sqft
$370,000$390,000
8625 REDSKIN COURT, ORLANDO
3 bd · 2 ba · 1,436 sqft
$365,000$375,000
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
$420,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
22 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
≈ $2,494/mo
$370,000 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
$2,200/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.
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, low-key neighborhood with genuinely central access — downtown Orlando and MCO airport are each about 20 minutes away, and Universal is roughly 33 minutes. Homes are zoned for Colonial High, Liberty Middle, and Hidden Oaks Elementary. The pace is quieter than busier communities like Hunters Creek.
Is Chickasaw Trails expensive?+
It's moderately priced for the Orlando market, with the lone active listing at $375,000 and homes selling over the past year at a median of $420,000. The median property tax is about $3,636 a year and the HOA is just $32 a month, so ongoing costs stay reasonable. It tends to come in below higher-end areas like Laureate Park.
What do homes cost in Chickasaw Trails?+
The current active listing is priced at $375,000, while the twelve homes sold in the last twelve months closed at a median of $420,000. Average price per square foot is about $242, and the median home size is around 1,547 square feet.
How is the market in Chickasaw Trails?+
Inventory is very tight — there's just one active listing right now — and homes have taken a median of 171 days to sell, so this isn't a rushed market. That said, sellers are still getting about 97% of their asking price, which means realistically priced homes do find buyers. For a wider view of options, browse Orlando homes for sale.
What about HOA fees and property taxes?+
The HOA is light here at a median of $32 per month, which keeps monthly carrying costs low. The median property tax runs about $3,636 per year. Between the two, ongoing ownership costs are modest for the area.
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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