Neighborhood · Kissimmee, Florida
Cypress Shadows
A quiet Kissimmee address within reach of the parks
1
Homes for sale
$319,900
Median list price
$165
Avg price / sqft
125
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
$319,900 – $320K price range
1,936 sqft median home
$87/mo median HOA
3 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
3
Sold, last 12 months
$290,000
Median sold price
92%
Sale-to-list ratio
What sellers actually get vs asking
65 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
▼ 11.9% 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
≈ $2,357/mo
$319,900 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.
On the calendar
Near Cypress Shadows
Jul
12
Sun
Sunset Saturday Artisan Market
Visitors will revel in the lively Sunset Saturday Artisan Market, teeming with local crafters and unique vendors from Central Florida. Event-goers can enjoy rhythm-filled…
Jul
12
Sun
Sunset Craft, Food, and Drink Market
This market is a bubbling hub of creativity with over 20 artisan vendors from across Florida. Attendees can indulge in hand-crafted food and beverages while dancing to th…
Jul
12
Sun
Rumba Brunch
11:30am
Every Sunday, attendees have the opportunity to immerse themselves in the authentic rumba music played live by wandering guitarists and vocalists. To accompany the riveti…
Jul
12
Sun
Promenade Second Sunday Car and Truck Show
The Second Sunday Car and Truck Show is a monthly gathering of classic to modern vehicles of all makes and models, complete with a DJ spinning a mix of classic rock and t…
Jul
24
Fri
Taste of Wisconsin
Taste of Wisconsin is a must-visit annual event for food enthusiasts looking to indulge in the state's culinary delights. With over 100 food vendors offering a variety of…
Jul
31
Fri
Red Not Chili Peppers
7:00pm
Hailing from Virginia, Red Not Chili Peppers is a tribute band to Red Hot Chili Peppers. Touring around the world, they deliver high-energy performances of chart-topping…
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 Cypress Shadows homes, in your inbox
A daily digest of new Kissimmee listings — straight from the MLS. Unsubscribe anytime.