Neighborhood · Kissimmee, Florida
Crestwood
Roomy gated living in Osceola County
1
Homes for sale
$569,900
Median list price
$183
Avg price / sqft
63
Median days on market
Crestwood sits in the heart of Kissimmee, a pocket of gated streets and generously sized homes where the median floor plan runs about 3,463 square feet. It's the kind of neighborhood buyers land on when they want space and a sense of enclosure without straying far from central Osceola County — Universal Orlando is roughly a 33-minute drive, and the wider world of Kissimmee homes for sale surrounds you with options like Storey Lake, Solara, and Windsor at Westside nearby.
The market here is thin and deliberate: just two active listings right now, both gated, priced almost identically around $584,950. Homes are selling close to expectations — sellers pulled in 98% of asking over the last year — and the typical property spends about 38 days on the market before it moves. With so little inventory, a buyer who's ready and pre-approved has real leverage when the right home does come up.
Crestwood is a community in Kissimmee, Florida.
Quick facts
$569,900 – $570K price range
3,119 sqft median home
$80/mo median HOA
4 sold in 12 months
Drive times
On the market now
Homes for sale in Crestwood
Every active listing inside the Crestwood boundary
Open full map search →The numbers that matter
The Crestwood market
4
Sold, last 12 months
$521,250
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
46 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
≈ $3,989/mo
$569,900 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 suits buyers who want space and privacy — homes are large, averaging around 3,463 square feet, and the active listings sit behind gates. You're centrally located in Osceola County with Universal Orlando about 33 minutes away, and the surrounding Kissimmee homes for sale give you plenty of nearby amenities.
Is Crestwood expensive?+
It's a mid-to-upper price point for the area, with current listings clustered tightly around $584,950. At roughly $171 per square foot, the pricing reflects the larger homes here rather than a luxury premium — there are no $1M+ listings on the market right now.
What do homes cost in Crestwood?+
The two active listings are priced between $584,900 and $585,000, with a median list price of $584,950. Over the past 12 months, three homes sold at a median of $485,000, so recent closings have landed below current asking prices.
How is the Crestwood market right now?+
Inventory is very tight — only two homes are active at the moment, and just three have sold in the last year. Sellers are averaging 98% of asking and homes take a median of 38 days to sell, so serious buyers should be ready to move quickly when something lists.
What are the HOA fees and property taxes like?+
The median HOA dues run about $80 a month, which is reasonable for a gated community. Property taxes are higher, with a median of roughly $8,643 a year, reflecting the size and value of homes in Storey Lake and comparable nearby communities.
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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