Neighborhood · Kissimmee, Florida
Cypress Ridge
Quiet Kissimmee living minutes from the theme parks
3
Homes for sale
$335,995
Median list price
$194
Avg price / sqft
43
Median days on market
Cypress Ridge is a small, gated pocket of Kissimmee built for people who want everyday calm without giving up proximity to everything Central Florida runs on. You're roughly 27 minutes from Walt Disney World and 26 from Orlando International, so weekend trips and airport runs stay simple. It sits among a well-known cluster of Osceola communities like Storey Lake, Solara, and Windsor at Westside, and assigned schools include the Osceola County School for the Arts.
The market here is genuinely tight — just 3 active listings right now, with a median list price of $335,995 and homes around 1,747 square feet. Over the past year only 6 homes sold, at a median of $330,000, and sellers collected about 97% of asking on average. With a median of 43 days on market, it's a measured pace where well-priced homes move and buyers have room to negotiate without a frenzy.
Cypress Ridge is a community in Kissimmee, Florida.
Quick facts
$325,000 – $360K price range
1,747 sqft median home
$250/mo median HOA
6 sold in 12 months
Drive times
On the market now
Homes for sale in Cypress Ridge
$359,900
2759 PLEASANT CYPRESS CIRCLE, KISSIMMEE
3 bd · 2.5 ba · 1,771 sqft
$325,000$330,000
2724 PLEASANT CYPRESS CIRCLE, KISSIMMEE
3 bd · 2.5 ba · 1,747 sqft
$335,995$345,990
2749 PLEASANT CYPRESS CIRCLE, KISSIMMEE
3 bd · 2.5 ba · 1,747 sqft
Every active listing inside the Cypress Ridge boundary
Open full map search →Find your fit
Browse Cypress Ridge
By feature — on the live map
The numbers that matter
The Cypress Ridge market
6
Sold, last 12 months
$330,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
38 days
Median time to sell
Cypress Ridge vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 2.9% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Cypress Ridge boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Cypress Ridge is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Cypress Ridge home
≈ $2,621/mo
$335,995 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$250/mo
Median HOA
From current listings inside the boundary
Population
265
Median age
40
Median income
$61,747
Median home value
$332,800
Beyond the listings
Living in Cypress Ridge
Appearance oriented
Top 1% in the U.S.Trend Trackers
This population lives as fast as the culture. They like to keep up with the latest trends, especially when it comes to apparel and accessories.
Attitudes
Top 1% 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.
Appearance oriented
Top 2% in the U.S.Smart Chic
Passionate about style, smart chic searches high and low for the perfect look - but not one that will break the bank.
Entertainment
Top 2% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Entertainment
Top 4% in the U.S.Lighthearted Fun
This population is all about keeping the mood light and good, clean fun. Common activities include spending time outdoors, catching up with friends, and dancing.
Hobbies & Interests
Top 4% in the U.S.Bookish
Always seeking the next book, article, or poem to read, this activity is prevalent in areas where reading is a way of life. Although a solo activity, the expression of the love of books is a bonding, communal experience.
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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