Neighborhood · Kissimmee, Florida
Cypress Reserve
Gated living minutes from Disney and the airport
11
Homes for sale
$370,000
Median list price
$198
Avg price / sqft
67
Median days on market
Cypress Reserve sits in the part of Kissimmee where suburban Osceola County living meets easy access to the theme-park corridor. It's a predominantly gated community — six of the eleven active listings are behind a gate — with sensible single-family homes that draw families and commuters alike. You're roughly 26 minutes from Walt Disney World and 27 from Orlando International Airport, which puts both work and weekends within reach. Assigned schools include the well-regarded Osceola County School for the Arts, along with Flora Ridge Elementary and Osceola High.
The market here is steady and mid-priced, not frenzied. The median list price is $370,000 with homes running about $198 per square foot, and over the past year ten homes sold at a median of $437,000 with sellers collecting 96% of asking. With a median 67 days on market, buyers have room to negotiate — and if Cypress Reserve doesn't fit, nearby options like Storey Lake, Solara, and Windsor at Westside round out the broader Kissimmee homes for sale picture.
Cypress Reserve is a community in Kissimmee, Florida.
Quick facts
$300,000 – $670K price range
1,900 sqft median home
$356/mo median HOA
$2,900/mo median rent
10 sold in 12 months
Drive times
On the market now
Homes for sale in Cypress Reserve
$469,900
2868 OCONNELL DRIVE, KISSIMMEE
3 bd · 2 ba · 2,180 sqft
$370,000
2821 PLYMOUTH PLACE, KISSIMMEE
3 bd · 2.5 ba · 1,838 sqft
$367,000
2806 PLYMOUTH PLACE, KISSIMMEE
3 bd · 2.5 ba · 1,838 sqft
$465,000
2886 OCONNELL DRIVE, KISSIMMEE
3 bd · 2 ba · 2,063 sqft
$469,000
2818 OCONNELL DRIVE, KISSIMMEE
5 bd · 2 ba · 2,287 sqft
$370,000$385,000
2101 PAINTER LANE, KISSIMMEE
3 bd · 2.5 ba · 1,820 sqft
$300,000$350,000
2852 EASTHAM LANE, KISSIMMEE
3 bd · 2.5 ba · 1,776 sqft
$335,000$345,000
2420 PAINTER LANE, KISSIMMEE
3 bd · 2 ba · 1,900 sqft
$355,000$360,000
2864 EASTHAM LANE, KISSIMMEE
3 bd · 2.5 ba · 1,890 sqft
$469,000
2831 OCONNELL DRIVE, KISSIMMEE
4 bd · 2 ba · 2,287 sqft
$669,900
2321 HINSDALE DRIVE, KISSIMMEE
5 bd · 3.5 ba · 3,497 sqft
Every active listing inside the Cypress Reserve boundary
Open full map search →Find your fit
Browse Cypress Reserve
By feature — on the live map
Where the market lives
The numbers that matter
The Cypress Reserve market
10
Sold, last 12 months
$437,000
Median sold price
96%
Sale-to-list ratio
What sellers actually get vs asking
74 days
Median time to sell
Cypress Reserve vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 17.5% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Cypress Reserve boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Cypress Reserve is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Cypress Reserve home
≈ $2,969/mo
$370,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$356/mo
Median HOA
From current listings inside the boundary
$2,900/mo
Median rent
Homes for rent inside the boundary
Population
1,318
Median age
40
Median income
$61,747
Median home value
$332,800
Beyond the listings
Living in Cypress Reserve
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.
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 Reserve FAQs
Is Cypress Reserve a good place to live?+
It suits buyers who want a gated, family-oriented setting with fast access to Orlando's job centers and attractions. You're about 27 minutes from Orlando International Airport and 26 from Walt Disney World, and assigned schools include the Osceola County School for the Arts. The neighborhood sits within the wider Kissimmee homes for sale market, so you get suburban quiet without giving up connectivity.
Is Cypress Reserve expensive?+
It's a mid-priced Kissimmee community rather than a luxury one — the median list price is $370,000 and there are currently no homes listed above $1 million. Active listings range from $300,000 to $669,900, so there's a spread depending on size and finish. At about $198 per square foot, it's an accessible entry point compared with higher-end nearby options.
What do homes cost in Cypress Reserve?+
Active listings run from $300,000 to $669,900 with a median list price of $370,000 and a median size around 1,900 square feet. Over the past 12 months, ten homes sold at a median of $437,000, so the gap between list and sold prices reflects a range of home sizes and conditions. Budget around $198 per square foot as a working benchmark.
How is the market in Cypress Reserve right now?+
It's a measured market with 11 active listings and a median 67 days on market, which gives buyers time to evaluate and negotiate. Sellers have been getting about 96% of asking on the ten homes sold over the past year. If inventory feels tight here, communities like Solara offer additional choices nearby.
What about HOA fees and property taxes?+
The median HOA runs about $356 per month, which is consistent with a gated community that maintains shared entrances and grounds. Median property tax is around $5,445 per year. Factor both into your monthly carrying costs alongside the mortgage, especially since much of the inventory here is gated.
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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