Neighborhood · Kissimmee, Florida
Cypress Reserve
Gated living minutes from Disney and the airport
10
Homes for sale
$457,495
Median list price
$200
Avg price / sqft
181
Median days on market
Cypress Reserve is a small gated community in Kissimmee's Osceola County, the kind of pocket that draws buyers who want space and a lock-behind-you front gate without pushing far from the theme parks. Most of the homes here run around 2,000 square feet, and the location does a lot of the work — Walt Disney World is roughly 26 minutes out, Orlando International Airport about 27, and downtown Orlando around 34. If you're weighing it against the bigger vacation-home enclaves like Storey Lake or Solara, Cypress Reserve reads more as a live-in neighborhood.
The market here is thin and deliberate. There are just 9 active listings with a median list price of $449,990, and homes are sitting an unusually long 175 days before they trade — which means patient buyers have room to negotiate. Over the last 12 months 11 homes sold at a median of $429,000, with sellers netting about 97% of asking, so realistic offers still get done. Compared to nearby Kissimmee homes for sale more broadly, this is a low-inventory corner where the right listing is worth moving on.
Cypress Reserve is a community in Kissimmee, Florida.
Quick facts
$300,000 – $670K price range
2,063 sqft median home
$100/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
$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
$449,990
2885 OCONNELL DRIVE, KISSIMMEE
3 bd · 2 ba · 2,063 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
≈ $3,179/mo
$457,495 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$100/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, residential feel with easy access to the parks and airport — Disney is about 26 minutes away and MCO around 27. Assigned schools include Flora Ridge Elementary, Kissimmee Middle, and Osceola High, plus the Osceola County School for the Arts. It's quieter and more live-in than the short-term rental enclaves nearby.
Is Cypress Reserve expensive?+
It sits in the mid-range for the area, with a median list price of $449,990 and active homes spanning $300,000 to $669,900. At roughly $199 per square foot, it's priced comparably to established Kissimmee neighborhoods rather than the premium vacation communities like Windsor at Westside.
What do homes cost in Cypress Reserve?+
Active listings run from $300,000 to $669,900 with a median around $449,990, while homes that actually sold over the past year did so at a median of $429,000. The typical home is about 2,063 square feet, so you're generally looking at three- to four-bedroom single-family houses.
How is the market right now?+
Inventory is tight at just 9 active listings, and homes are taking about 175 days to sell — a slower pace that favors patient buyers. Still, the 11 sales over the last year closed at roughly 97% of asking, so sellers here aren't giving properties away, and well-priced offers move.
What about HOA fees and property taxes?+
The median HOA is about $100 a month, which is reasonable for a gated community, and the median property tax runs roughly $5,482 a year. If you're considering renting instead, the median rent in the area is around $2,775 a 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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