Neighborhood · Orlando, Florida
Chickasaw Woods
Established East Orlando living close to everything
Chickasaw Woods sits in east Orlando, an established neighborhood of single-family homes on tree-lined streets that trade the churn of new development for settled, lived-in character. The location does a lot of the heavy lifting: downtown Orlando is about 17 minutes away and Orlando International Airport roughly 18, with Universal Orlando reachable in under half an hour. It's a practical, unflashy pocket that appeals to buyers who want space and a real commute without paying resort-town prices.
The market here is thin and steady rather than frantic. With just one active listing at $390,000 and eight homes sold over the past year at a median of $365,450, inventory is scarce — and sellers have been getting 100% of asking on average, so there's little room to lowball. If you're comparing it against pricier east-side options like Laureate Park or master-planned Hunters Creek to the south, Chickasaw Woods reads as the more attainable, no-frills choice.
Chickasaw Woods is a community in Orlando, Florida.
Quick facts
7 sold in 12 months
Drive times
On the market now
Homes for sale in Chickasaw Woods
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
Every active listing inside the Chickasaw Woods boundary
Open full map search →The numbers that matter
The Chickasaw Woods market
7
Sold, last 12 months
$355,000
Median sold price
100%
Sale-to-list ratio
What sellers actually get vs asking
5 days
Median time to sell
Chickasaw Woods vs Orlando
Median sold price — 3-yr, 3-mo rolling
▼ 10.1% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Chickasaw Woods boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Chickasaw Woods is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
Population
954
Median age
41
Median income
$80,563
Median home value
$305,700
Beyond the listings
Living in Chickasaw Woods
Relationships
Top 1% in the U.S.Networking
Driven to succeed in the business world, this population seeks to progress in their career through networking happy hours, summits, and connecting with other professionals online.
Food & Drink
Top 1% 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.
Food & Drink
Top 1% in the U.S.Asian Food & Culture
Asian culture has a lot to offer, but the Asian cuisine tends to be the most frequently referenced. This population is talking about Asian dishes, holidays, and drinks.
Emotional
Top 1% in the U.S.Gratitude
From generous tipping to standing ovations, this population has a way with giving someone a pat on the back.
Culture
Top 1% in the U.S.Dance Devotion
Some dance for fitness, others for fun, and a few turn it into a profession. No matter how these people groove to the music, their love for dance is what bonds them.
Lifestyles
Top 1% 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.
People who close here
Our Orlando experts
Straight answers
Chickasaw Woods FAQs
Is Chickasaw Woods a good place to live?+
It's a settled east Orlando neighborhood that trades on location — downtown is about 17 minutes out and Orlando International Airport around 18. Assigned schools include Hidden Oaks Elementary, Liberty Middle, and Colonial High. It suits buyers who want a straightforward commute and an established street over resort-style amenities.
Is it expensive to buy here?+
Not by east Orlando standards. The median sold price over the past year was $365,450, and the single active listing is priced at $390,000, which makes it more attainable than pricier options like Hunters Creek. Homes here run about $273 per square foot on a median size of 1,431 square feet.
What do homes cost in Chickasaw Woods?+
Expect roughly $365,000 to $390,000 for a typical single-family home, based on eight sales in the past year and the current $390,000 listing. At about $273 per square foot, that lands you a home around 1,431 square feet. Pool homes do come up — one of the active listings has a pool.
How is the market right now?+
Inventory is very tight, with just one home currently active on the market. Sellers have been getting 100% of asking on average, though the median 151 days on market shows well-priced homes still take time to move. Buyers should be ready to act on the rare listing rather than expect a wide selection.
What about HOA fees and property taxes?+
Property taxes here run a median of about $2,368 per year, which is modest for the area. HOA data isn't available for the neighborhood right now, so confirm any dues directly with the listing before you make an offer. Compared with amenity-heavy communities like Metro West, carrying costs here tend to stay lean.
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 Woods homes, in your inbox
A daily digest of new Orlando listings — straight from the MLS. Unsubscribe anytime.