Neighborhood · Kissimmee, Florida
Chelsea Square
Compact Kissimmee living close to the theme parks
2
Homes for sale
$212,951
Median list price
$202
Avg price / sqft
84
Median days on market
Chelsea Square is a small residential pocket of Kissimmee built around modestly sized, attainable homes — the kind of neighborhood where a shorter commute and lower carrying costs matter more than square footage. With Walt Disney World about 19 minutes away, Universal Orlando near 24, and Orlando International Airport roughly 28 minutes out, it puts you inside the region's biggest job and entertainment hubs without paying resort-community prices. Nearby communities like Lake Marion Village and Storey Lake show the range Kissimmee offers, but Chelsea Square keeps things grounded and everyday.
For a buyer today, this is a tight, low-inventory market — there's currently just one active listing, priced at $224,901. Over the last 12 months only four homes sold, at a median of $193,750, with sellers collecting about 98% of asking. Homes here tend to sit a while (median 95 days), which gives a prepared buyer room to negotiate on the right property, unlike the faster pace at resort-style spots like Solara or Windsor at Westside.
Chelsea Square is a community in Kissimmee, Florida.
Quick facts
$210,000 – $216K price range
1,056 sqft median home
$125/mo median HOA
$1,800/mo median rent
3 sold in 12 months
Drive times
On the market now
Homes for sale in Chelsea Square
$210,000
3227 CHESSWOOD AVENUE, KISSIMMEE
3 bd · 2 ba · 1,056 sqft
$215,901$224,901
1947 BENTLEY BOULEVARD, KISSIMMEE
3 bd · 2 ba · 1,056 sqft
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
3
Sold, last 12 months
$195,000
Median sold price
99%
Sale-to-list ratio
What sellers actually get vs asking
38 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
▼ 8.2% 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
≈ $1,688/mo
$212,951 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
$1,800/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®
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.
Never miss a listing
New Chelsea Square homes, in your inbox
A daily digest of new Kissimmee listings — straight from the MLS. Unsubscribe anytime.