Neighborhood · Kissimmee, Florida
Crestwood
A quiet Kissimmee pocket with room to spread out
3
Homes for sale
$595,000
Median list price
$188
Avg price / sqft
11
Median days on market
Crestwood sits in the heart of Osceola County, a residential corner of Kissimmee where homes run larger than the local average and the pace stays calm. Buyers here lean toward space over density — the median home checks in around 3,119 square feet — and gated streets and private pools show up more often than not. It's an easy base for anyone who works or plays around Central Florida, with Universal Orlando roughly 33 minutes up the road.
The market is small and moves fast: just three active listings right now, with a median list price of $595,000 and homes typically going under contract in about 8 days. Over the past year, sellers have collected 98% of asking on average, so there's little room for lowball offers. If you're comparing nearby options, the vacation-rental communities like Storey Lake and Solara offer a different flavor, while Lake Marion Village trends more traditional.
Crestwood is a community in Kissimmee, Florida.
Quick facts
$479,900 – $650K price range
3,119 sqft median home
$80/mo median HOA
3 sold in 12 months
Drive times
On the market now
Homes for sale in Crestwood
$649,900
3480 FOREST RIDGE LANE, KISSIMMEE
4 bd · 3.5 ba · 3,119 sqft
$479,900
3476 FOREST RIDGE LANE, KISSIMMEE
4 bd · 2 ba · 2,395 sqft
$595,000$600,000
3463 FOREST RIDGE LANE, KISSIMMEE
4 bd · 3.5 ba · 3,807 sqft
Every active listing inside the Crestwood boundary
Open full map search →Find your fit
Browse Crestwood
By feature — on the live map
Where the market lives
The numbers that matter
The Crestwood market
3
Sold, last 12 months
$485,000
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
62 days
Median time to sell
Crestwood vs Kissimmee
Median list price
Price per sqft
Days on market
Live Stellar MLS data — every listing and closed sale inside the Crestwood boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Crestwood is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Crestwood home
≈ $3,760/mo
$595,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$80/mo
Median HOA
From current listings inside the boundary
Population
1,454
Median age
32
Median income
$70,575
Median home value
$265,600
Beyond the listings
Living in Crestwood
Hobbies & Interests
Top 12% in the U.S.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.
Pieces of History
You can find these people researching an upcoming exhibit at the natural history museum or learning about a famous monument. This population enjoys learning about the past.
Lifestyles
Top 24% in the U.S.Nerd Culture
These people aren't afraid to nerd out. Common activities include comic books, video games, and often intellectual pursuits.
Appearance oriented
Top 25% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Attitudes
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.
Active
Outdoor Adventures
Appreciating the outdoors, this population wants to actively engage with nature. Whether it's finding a new hiking trail or looking for the perfect spot to catch the sunset, they seek to explore the world around them.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Crestwood FAQs
Is Crestwood a good place to live?+
It's a calm, residential slice of Kissimmee built around larger homes, with gated streets and pools common among current listings. Assigned schools include Osceola County School for the Arts, Kissimmee Middle School, Flora Ridge Elementary, and Osceola High School. The 33-minute drive to Universal Orlando makes it practical for both work and weekend plans.
Is Crestwood expensive?+
It sits toward the upper-mid range for the area, with a median list price of $595,000 and active listings running from $479,900 to $649,900. There are currently no listings above $1M, so it stays under the luxury tier while still commanding solid prices for its home sizes.
What do homes cost in Crestwood?+
The median list price is $595,000 and homes average about $188 per square foot across a median size of 3,119 square feet. Over the past 12 months the median sold price came in at $485,000, so recent sales have closed below current asking levels — a gap worth watching as you shop the wider Kissimmee market.
How is the market right now?+
Inventory is thin, with just three active listings and three sales in the past year, and homes move fast at a median of 8 days on market. Sellers are averaging 98% of asking, which signals a tight, seller-leaning environment where prepared buyers win.
What about HOA fees and property taxes?+
The median HOA runs about $80 per month, which is modest for a community with gated and pool amenities. Property taxes come in around $4,020 per year at current values, so factor both into your monthly budget.
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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