Neighborhood · Orlando, Florida
Chickasaw Oaks
East Orlando living close to the airport and downtown
4
Homes for sale
$428,500
Median list price
$272
Avg price / sqft
52
Median days on market
Chickasaw Oaks sits in east Orlando, a quiet residential pocket where mature trees and modest single-story homes set the tone. It's the kind of neighborhood that trades flash for convenience — you're about 16 minutes from Orlando International Airport, 19 from downtown, and within reach of Universal about half an hour away. Families here feed into Colonial High, Odyssey Middle, and Hidden Oaks Elementary, and neighbors like South Semoran and Metro West put more of the city's shopping and workplaces within an easy drive.
For buyers, this is a small, tightly held market — just 4 active listings right now, with a median list price of $428,500. Homes here are practical in size, around 1,545 square feet at roughly $272 per square foot, and sellers have been getting about 99% of asking over the past year. If you're comparing against pricier east-side options like Laureate Park, Chickasaw Oaks offers a more attainable entry point among broader Orlando homes for sale.
Chickasaw Oaks is a community in Orlando, Florida.
Quick facts
$409,000 – $440K price range
1,545 sqft median home
$18/mo median HOA
23 sold in 12 months
Drive times
On the market now
Homes for sale in Chickasaw Oaks
$439,900
4901 REGINALD ROAD, ORLANDO
4 bd · 2 ba · 1,510 sqft
$438,000
4768 CROSSBOW COURT, ORLANDO
4 bd · 2 ba · 1,510 sqft
$419,000$420,000
8713 CATBRIAR BAY WAY, ORLANDO
3 bd · 2.5 ba · 1,580 sqft
$409,000$414,900
8509 LYONIA DRIVE, ORLANDO
4 bd · 2 ba · 1,704 sqft
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
23
Sold, last 12 months
$368,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
7 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
▼ 3.5% 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
≈ $2,916/mo
$428,500 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$18/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 a solid fit if you value convenience over flash — you're about 16 minutes from MCO, 19 from downtown Orlando, and roughly 31 from Universal. Homes feed into Colonial High, Odyssey Middle, and Hidden Oaks Elementary. The neighborhood is quiet and residential, with easy access to nearby areas like Metro West.
Is Chickasaw Oaks expensive?+
Not by Orlando standards — the median list price is $428,500 and the median sold price over the past year was $378,000. There are no listings above $1M here, and the light $18/month median HOA keeps carrying costs down. Compared to newer east-side communities like Laureate Park, it's a more attainable choice.
What do homes cost in Chickasaw Oaks?+
Active listings currently range from $409,000 to $439,900, with a median around $428,500. Homes run about $272 per square foot on a median size near 1,545 square feet. Expect practical single-family homes rather than sprawling new builds.
How is the market in Chickasaw Oaks right now?+
It's a small, steady market with just 4 active listings and 21 sales over the past 12 months. Homes take a median of 50 days to sell, and sellers are getting about 99% of their asking price. Low inventory means well-priced homes here tend to move without deep discounting.
What about HOA fees and property taxes?+
The HOA is minimal at a median of $18 per month, so community fees won't weigh heavily on your budget. Property taxes run a median of about $5,154 per year. Together, that keeps monthly ownership costs reasonable relative to the price point.
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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