Neighborhood · Kissimmee, Florida
Cypress Shadows
Quiet Kissimmee living within reach of the parks
Cypress Shadows is a small residential pocket of Kissimmee where the pace is calmer than the resort corridors nearby. Homes here run a comfortable 1,936 square feet on average, and the location keeps you about 36 minutes from Walt Disney World and 42 minutes from Orlando International Airport — close to the action without living in it. Families lean on assigned schools like Sunrise Elementary and the Osceola County School for the Arts, and the surrounding area holds well-known communities including Lake Marion Village and Storey Lake.
For buyers, this is a thin, patient market. There's currently just one active listing at $299,000, and homes have been taking around 166 days to sell — so anyone shopping here should expect limited choice and room to negotiate. Over the last year only four homes changed hands, at a median of $292,500, with sellers netting about 94% of asking. If Cypress Shadows is too quiet on inventory, nearby options like Solara and Windsor at Westside widen the search.
Cypress Shadows is a community in Kissimmee, Florida.
Quick facts
4 sold in 12 months
Drive times
On the market now
Homes for sale in Cypress Shadows
Nothing active right now.
Set an alert below and we’ll email you the moment something lists here.
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 sold price — 3-yr, 3-mo rolling
▼ 23.7% 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.
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®
Straight answers
Cypress Shadows FAQs
Is Cypress Shadows a good place to live?+
It's a quiet, family-oriented corner of Kissimmee with roomy homes and easy reach to the parks — about 36 minutes to Disney and 42 to the airport. Assigned schools include Sunrise Elementary, Horizon Middle, and the Osceola County School for the Arts. If you want a calmer base than the resort corridors, it fits well.
Is Cypress Shadows expensive?+
No — it sits in an accessible price band, with the current listing at $299,000 and last year's median sold price at $292,500. At roughly $154 per square foot, it lands below many resort-style communities nearby in Kissimmee.
What do homes cost in Cypress Shadows?+
The one active listing is priced at $299,000 for about 1,936 square feet. Over the past 12 months, four homes sold at a median of $292,500, so pricing has been very consistent in the high $200s to right around $300,000.
How is the market in Cypress Shadows?+
It's slow and thin — just one home is listed now, and the median time on market is about 166 days. With only four sales in the last year and sellers getting around 94% of asking, buyers have real negotiating room but limited selection.
What are the HOA fees and property taxes?+
HOA dues run about $87 a month, which is modest for the area. Property taxes come in around $4,497 a year at current values.
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.