Neighborhood · Kissimmee, Florida
Cypress Shores
Spacious homes and lakeside living in central Kissimmee
1
Homes for sale
$585,800
Median list price
$179
Avg price / sqft
59
Median days on market
Cypress Shores sits in Osceola County, part of a Kissimmee landscape defined by lakes, big lots, and easy access to Central Florida's core. Homes here run large — the median is a roomy 3,269 square feet — and the waterfront setting gives the neighborhood a quieter, more residential feel than the resort communities nearby. Families are drawn to assigned schools like the Osceola County School for the Arts and Osceola High School, and the area connects easily to the wider range of Kissimmee homes for sale and standout communities like Storey Lake and Solara.
For buyers, this is a small, tightly-held market. There's currently one active listing at $598,500, and just four homes have sold in the past year at a median of $570,000. With sellers collecting about 95% of asking, pricing has been disciplined — worth weighing against the more active inventory in Lake Marion Village and Windsor at Westside if you need more to compare.
Cypress Shores is a community in Kissimmee, Florida.
Quick facts
$585,800 – $586K price range
3,269 sqft median home
4 sold in 12 months
On the market now
Homes for sale in Cypress Shores
Every active listing inside the Cypress Shores boundary
Open full map search →Find your fit
Browse Cypress Shores
By feature — on the live map
The numbers that matter
The Cypress Shores market
4
Sold, last 12 months
$570,000
Median sold price
95%
Sale-to-list ratio
What sellers actually get vs asking
27 days
Median time to sell
Cypress Shores vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▲ 8.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Cypress Shores boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Cypress Shores is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Cypress Shores home
≈ $3,573/mo
$585,800 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
Population
135
Median age
39
Median income
$136,012
Median home value
$419,200
Beyond the listings
Living in Cypress Shores
Relationships
Top 1% in the U.S.Happily Ever After
Whether it's the stress of wedding planning or looking back on that special day, this population has their eyes and hearts focused on lifelong commitment.
Lifestyles
Top 5% 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.
Appearance oriented
Top 12% in the U.S.Men's Style
This population is all about finding the latest in men's style - from fashion to grooming. Captures guys looking to stay on trend and significant others assisting with shopping.
Hobbies & Interests
Top 18% 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.
Attitudes
Top 20% in the U.S.Home & Leisure
There's no place like home. This activity is highest when people are feeling relaxed, like sharing a meal with friends or enjoying their morning coffee in their own home.
Food & Drink
Top 20% in the U.S.Sweet Treats
This population has a sweet tooth, and they're looking for treats to satisfy their sugar craving, including candy, cupcakes and flavorful toppings.
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 Shores FAQs
Is Cypress Shores a good place to live?+
It's a good fit if you want a larger home in a quieter, waterfront-leaning corner of Kissimmee. The median home is 3,269 square feet, and students are assigned to well-regarded schools including the Osceola County School for the Arts. It's a residential community rather than a resort-style development, so it appeals to buyers planting roots.
Is Cypress Shores expensive?+
It sits in the mid-to-upper range for the area, with the current listing at $598,500 and last year's homes selling at a median of $570,000. That reflects the larger home sizes here rather than premium finishes. For comparison, communities like Solara offer different price points and product types.
What do homes cost in Cypress Shores?+
The single active listing is priced at $598,500, and the median sold price over the past year was $570,000. That works out to roughly $183 per square foot on a median home size of 3,269 square feet. Inventory is thin, so prices reflect a small set of recent sales.
How is the market in Cypress Shores?+
It's a low-inventory, slow-turnover market — only four homes sold in the past year and there's currently one active listing. Homes take a median of 48 days to sell, and sellers are getting about 95% of their asking price. That balance means well-priced homes move, but there's still room to negotiate.
What about HOA fees and property taxes?+
Property taxes here run a median of about $3,326 per year based on recent data. HOA figures aren't available for the current listings, so confirm any community dues directly on the property you're considering. Your agent can pull the specifics before you make an offer.
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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