Neighborhood · Kissimmee, Florida
Cypress Shadows
A quiet Kissimmee address within reach of the parks
1
Homes for sale
$299,000
Median list price
$154
Avg price / sqft
158
Median days on market
Cypress Shadows is a small residential pocket in Osceola County, the kind of place where the pace slows down but the theme parks are still an easy day trip — Walt Disney World sits about 36 minutes away and Orlando International Airport around 42. Homes here run a practical size, with a median footprint near 1,936 square feet, and the neighborhood leans toward buyers who want space and a settled feel over resort-style flash. If you're comparing it against the larger master-planned options around town, it reads calmer and more low-key than communities like Storey Lake or Solara.
The market here is thin and deliberate — there's currently just one active listing, priced at $319,900, so inventory moves at its own tempo. Over the past year three homes sold at a median of $290,000, with sellers collecting about 92% of asking on average and properties taking a median 125 days to close. For a buyer, that means room to negotiate and time to think, which is a different rhythm than the fast-turning Kissimmee homes for sale closer to the attractions or the vacation-rental stock over at Windsor at Westside.
Cypress Shadows is a community in Kissimmee, Florida.
Quick facts
$299,000 – $299K price range
1,936 sqft median home
$87/mo median HOA
4 sold in 12 months
Drive times
On the market now
Homes for sale in Cypress Shadows
Every active listing inside the Cypress Shadows boundary
Open full map search →The numbers that matter
The Cypress Shadows market
4
Sold, last 12 months
$292,500
Median sold price
94%
Sale-to-list ratio
What sellers actually get vs asking
34 days
Median time to sell
Cypress Shadows vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 13.4% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Cypress Shadows boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Cypress Shadows is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Cypress Shadows home
≈ $2,247/mo
$299,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$87/mo
Median HOA
From current listings inside the boundary
Population
882
Median age
36
Median income
$82,141
Median home value
$331,400
Beyond the listings
Living in Cypress Shadows
Lifestyles
Top 4% 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.
Attitudes
Top 9% in the U.S.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.
Beliefs
Top 9% in the U.S.Local Engagement
These citizens want to make their neighborhood a better, more beautiful place to live. They're attentive to the needs and affairs of the local community.
Appearance oriented
Top 10% in the U.S.Body Art
Who says the body isn't a canvas? This population loves talking about tattoos, body art and piercings.
Entertainment
Top 10% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Hobbies & Interests
Top 10% in the U.S.Engine Enthusiast
This population loves working on and showing off their cars, trucks and motorcycles. You can find them researching car shows and the hottest models on the lot.
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.
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