Neighborhood · Kissimmee, Florida
Chelsea Square
Compact, walkable living in the heart of Kissimmee
1
Homes for sale
$224,901
Median list price
$213
Avg price / sqft
60
Median days on market
Chelsea Square is a small, tidy pocket of Kissimmee where homes run efficient in size — the median is right around 1,056 square feet — making it a practical fit for first-time buyers, downsizers, or anyone who wants low-maintenance space close to town. It sits within reach of the schools that anchor central Kissimmee, including the Osceola County School for the Arts, and puts you a short drive from the broader mix of Kissimmee homes for sale across Osceola County.
The market here is genuinely quiet: there's just one active listing at $224,901, and only four homes changed hands over the past year at a median sold price of $193,750. That thin inventory means well-priced homes move at a steady, unhurried pace — the median listing spent about 60 days on market — and sellers are still capturing roughly 98% of asking. If Chelsea Square doesn't have what you need, nearby resort-style communities like Storey Lake, Solara, and Windsor at Westside offer very different options within the same market.
Chelsea Square is a community in Kissimmee, Florida.
Quick facts
$224,901 – $225K price range
1,056 sqft median home
$125/mo median HOA
$1,395/mo median rent
4 sold in 12 months
On the market now
Homes for sale in Chelsea Square
Every active listing inside the Chelsea Square boundary
Open full map search →Find your fit
Browse Chelsea Square
By feature — on the live map
The numbers that matter
The Chelsea Square market
4
Sold, last 12 months
$193,750
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
21 days
Median time to sell
Chelsea Square vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 8.3% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Chelsea Square boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Chelsea Square is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Chelsea Square home
≈ $1,750/mo
$224,901 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$125/mo
Median HOA
From current listings inside the boundary
$1,395/mo
Median rent
Homes for rent inside the boundary
Population
1,672
Median age
31
Median income
$44,418
Beyond the listings
Living in Chelsea Square
Emotional
Top 2% in the U.S.Heartfelt Sharing
This population is characterized by vulnerability. Looking to unload emotional burdens, activities include confessions, apologies, and long-form posts.
Beliefs
Top 13% 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.
Emotional
Top 19% in the U.S.Deep Emotions
Sharing personal struggles and stories overcoming relationship issues, this population seeks to tell others about their emotional journeys.
Beliefs
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.
Beliefs
Mindfulness & Spirituality
Seeking peace and well-being through meditation, gratitude and spirituality.
Attitudes
Past Reflections
This population enjoys thinking about past historical events, including family genealogy, landmarks, and political affairs.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Chelsea Square FAQs
Is Chelsea Square a good place to live?+
It's a good fit if you want a compact, low-maintenance home in central Kissimmee with easy access to town. Assigned schools include the Osceola County School for the Arts and Kissimmee Elementary, and the neighborhood's efficient home sizes make it practical for first-timers and downsizers alike.
Is Chelsea Square expensive?+
No — it's one of the more affordable pockets of the area, with the current listing at $224,901 and homes over the past year selling at a median of $193,750. For a wider range of price points, it's worth comparing against other Kissimmee homes for sale across the county.
What do homes cost in Chelsea Square?+
The single active listing is priced at $224,901, or about $213 per square foot, and recent sales have landed around a $193,750 median. Homes here tend to be compact, with a median size near 1,056 square feet.
How is the market in Chelsea Square right now?+
It's a thin, slow-moving market — just one home is active and only four sold in the past twelve months. Listings take about 60 days to sell, and sellers are averaging roughly 98% of their asking price, so well-priced homes still find buyers.
What are the HOA fees and property taxes like?+
HOA dues run about $125 per month, and the median annual property tax is around $2,757. If you're weighing amenity-heavy alternatives, communities like Solara carry different fee structures worth comparing.
Keep exploring
More Kissimmee 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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