Neighborhood · Orlando, Florida
Chickasaw Oaks
Established East Orlando living with an easy commute
1
Homes for sale
$399,900
Median list price
$265
Avg price / sqft
102
Median days on market
Chickasaw Oaks is a settled East Orlando neighborhood where mature trees, single-family lots, and a low-key pace do the talking. It sits within a quick reach of the region's major employment centers — Orlando homes for sale don't often come with a 16-minute run to MCO and a 19-minute drive to downtown built in. Families here draw on Hidden Oaks Elementary, Odyssey Middle, and Colonial High, and neighbors trade notes with nearby communities like Metro West and Hunters Creek.
For a buyer today, this is a tight, competitive corner of the market. Only two homes are active right now, with a median list price of $379,950 and homes trading around $226 per square foot. Sellers over the last year have collected about 99% of asking on average, so plan to come in prepared rather than lowballing — though a median of 44.5 days on market gives you a little room to think.
Chickasaw Oaks is a community in Orlando, Florida.
Quick facts
$399,900 – $400K price range
1,510 sqft median home
$20/mo median HOA
24 sold in 12 months
Drive times
On the market now
Homes for sale in Chickasaw Oaks
Every active listing inside the Chickasaw Oaks boundary
Open full map search →Find your fit
Browse Chickasaw Oaks
By feature — on the live map
The numbers that matter
The Chickasaw Oaks market
24
Sold, last 12 months
$390,950
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
9 days
Median time to sell
Chickasaw Oaks vs Orlando
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 9.0% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Chickasaw Oaks boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Chickasaw Oaks is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Chickasaw Oaks home
≈ $2,778/mo
$399,900 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$20/mo
Median HOA
From current listings inside the boundary
Population
552
Median age
44
Median income
$136,382
Median home value
$274,400
Beyond the listings
Living in Chickasaw Oaks
Emotional
Top 15% in the U.S.Awestruck
Great things are meant to be shared, and this population is eager to show others what they find to be amazing, beautiful and exciting.
Lifestyles
Top 19% in the U.S.Wealth Signaling
Interested in the finer things life has to offer, this population wants to display their lifestyle by discussing luxury products. Often references jewelry, cars, and home features.
Hobbies & Interests
Top 22% in the U.S.Engine Enthusiast
This population loves working on and showing off their cars, trucks and motorcycles. You can find them researching car shows and the hottest models on the lot.
Appearance oriented
Top 22% in the U.S.Trend Trackers
This population lives as fast as the culture. They like to keep up with the latest trends, especially when it comes to apparel and accessories.
Attitudes
Top 25% in the U.S.Deal Seekers
These people are hunting discounts, contests, and promotions. The population loves a good sale, and they can't wait to share their bargain finds and winnings with friends and family.
Hobbies & Interests
Wanderlust
Always thinking about their next destination, this population loves exploring new places abroad or right in their own backyard. They hold onto past trips by sharing their favorite memories and pictures year round.
People who close here
Our Orlando experts
Straight answers
Chickasaw Oaks FAQs
Is Chickasaw Oaks a good place to live?+
It's an established East Orlando neighborhood built around single-family homes, mature landscaping, and a low HOA of about $20 a month. The location is a big draw, with roughly 16 minutes to Orlando International Airport and 19 to downtown. It's assigned to Hidden Oaks Elementary, Odyssey Middle, and Colonial High.
Is Chickasaw Oaks expensive?+
Not by Orlando's higher-end standards — the median list price is $379,950 and homes trade around $226 per square foot. Active listings currently range from $350,000 to $409,900, and there are no $1M+ homes on the market. It compares reasonably with newer communities like Laureate Park while keeping a more established feel.
What do homes cost in Chickasaw Oaks?+
The median list price is $379,950, and over the past 12 months the median sold price was $378,000 — so listing and closing numbers line up closely. Homes run about $226 per square foot with a median size near 1,726 square feet.
How is the market in Chickasaw Oaks?+
It's a low-inventory market with just two active listings right now and 25 homes sold over the past year. Sellers average about 99% of asking, and the median time on market is 44.5 days. That combination means well-priced homes move, but buyers still have a little breathing room to evaluate.
What about HOA fees and property taxes?+
The median HOA here is a modest $20 a month, which is low for the Orlando area. Property taxes run a median of about $5,642 per year. Between the two, ongoing carrying costs stay reasonable relative to nearby communities like Hunters Creek.
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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