Neighborhood · Kissimmee, Florida
Cypress Ridge
An easygoing Kissimmee address close to the parks
3
Homes for sale
$345,990
Median list price
$197
Avg price / sqft
16
Median days on market
Cypress Ridge sits in the heart of Osceola County, close enough to the theme parks to feel the energy but tucked into a quieter residential rhythm. Disney is about 27 minutes away, Orlando International Airport around 26, and downtown Orlando a manageable 33 — the kind of location that works for commuters, families, and anyone who wants weekend adventures without living on top of them. It's a small community with a gated pocket, and it shares this stretch of Kissimmee with well-known names like Storey Lake, Solara, and the 55+ Solivita.
For buyers, this is a tight, fast-moving market. There are just 3 active listings right now, with a median list price of $345,990 and homes selling in about 16 days at 97% of asking. If you're comparing it to the broader range of Kissimmee homes for sale or nearby Lake Marion Village, Cypress Ridge lands in the accessible mid-market — but with limited inventory, you'll want to move decisively when the right one comes up.
Cypress Ridge is a community in Kissimmee, Florida.
Quick facts
$330,000 – $360K price range
1,747 sqft median home
$250/mo median HOA
$2,200/mo median rent
4 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
$330,000$335,000
2724 PLEASANT CYPRESS CIRCLE, KISSIMMEE
3 bd · 2.5 ba · 1,747 sqft
$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
4
Sold, last 12 months
$329,500
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
74 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
▼ 6.0% 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
≈ $2,674/mo
$345,990 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
$2,200/mo
Median rent
Homes for rent 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.
On the calendar
Near Cypress Ridge
Jul
11
Sat
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
11
Sat
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
11
Sat
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
11
Sat
Bands, Brew, and BBQ
Bands, Brew, and BBQ delivers the ultimate combination of great music, mouthwatering barbecue, and refreshing craft beer. With live performances by talented artists, an a…
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
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…
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 Ridge FAQs
Is Cypress Ridge a good place to live?+
It's a good fit if you want proximity to the theme parks and airport without the constant crowds — Disney is about 27 minutes away and MCO around 26. The community is zoned for well-regarded schools including Osceola County School for the Arts and Flora Ridge Elementary, and it sits among established Kissimmee neighborhoods like Solara.
Is Cypress Ridge expensive?+
It lands in the accessible mid-market for the Kissimmee area, with a median list price of $345,990 and homes ranging from $330,000 to $359,900. At roughly $197 per square foot, it's a practical option compared to the higher-priced resort communities nearby.
What do homes cost in Cypress Ridge?+
Current listings run from $330,000 to $359,900 with a median of $345,990, and the median home size is about 1,747 square feet. Over the past year, 4 homes sold at a median price of $329,500, so the closing numbers track closely to today's asking prices.
How is the market in Cypress Ridge?+
It's fast and tight — just 3 active listings, a median of 16 days on market, and sellers collecting 97% of asking on average. With that little inventory, serious buyers should be ready to act quickly, much like they would across the broader Kissimmee homes for sale market.
What about HOA fees and property taxes?+
Expect a median HOA of around $250 per month, which is typical for this part of Osceola County. Median property taxes run about $4,689 per year, and if you're weighing renting first, the median rent in the area is roughly $2,200 per month.
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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