Neighborhood · Kissimmee, Florida
Four Seasons At Orlando
Gated living minutes from the theme park corridor
20
Homes for sale
$500,000
Median list price
$253
Avg price / sqft
36
Median days on market
Four Seasons At Orlando is a gated community in Kissimmee, built for people who want low-maintenance Florida living without giving up space — the median home here runs just over 2,000 square feet. You're about 24 minutes from Walt Disney World and 41 from Orlando International, which puts the parks, the airport, and everyday errands all within an easy drive. It sits in the same stretch of Osceola County as resort-style neighborhoods like Storey Lake and Solara, but reads more residential than rental.
For a buyer today, there are 20 active listings with a median list price of $500,000, and homes are moving — the typical one sells in about 20 days. Over the past year 34 homes closed at a median of $481,000, with sellers collecting 97% of asking on average, so this is a market where well-priced homes don't linger. If you're comparing it against broader Kissimmee homes for sale or nearby Windsor at Westside, the price range here spans $293,000 to $749,000 depending on size and finishes.
Four Seasons At Orlando is a community in Kissimmee, Florida.
Quick facts
$270,000 – $749K price range
2,006 sqft median home
$410/mo median HOA
34 sold in 12 months
Drive times
On the market now
Homes for sale in Four Seasons At Orlando
View all 20 →
$575,000
1999 LIMESTONE TRAIL, KISSIMMEE
3 bd · 2 ba · 2,202 sqft
$575,000
1900 ESTUARY LANE, KISSIMMEE
3 bd · 2 ba · 2,202 sqft
$345,000
1646 KEY BAY TRAIL, KISSIMMEE
2 bd · 2 ba · 1,557 sqft
$749,000
7969 HANSON BAY PLACE, KISSIMMEE
3 bd · 2.5 ba · 2,194 sqft
$675,000
2016 FLORA PASS PLACE, KISSIMMEE
3 bd · 2 ba · 2,202 sqft
$549,000
1983 LIMESTONE TRAIL, KISSIMMEE
3 bd · 2 ba · 2,202 sqft
$695,000
7748 FOUR SEASONS BOULEVARD, KISSIMMEE
3 bd · 3 ba · 2,754 sqft
$355,000
2042 KEY BAY TRAIL, KISSIMMEE
2 bd · 2 ba · 1,557 sqft
$349,500
1987 KEY BAY TRAIL, KISSIMMEE
2 bd · 2 ba · 1,437 sqft
$419,999
2160 ANTILLES CLUB DRIVE, KISSIMMEE
2 bd · 2 ba · 1,778 sqft
$349,900
1908 FLORA PASS PLACE, KISSIMMEE
2 bd · 2 ba · 1,437 sqft
$549,000
7789 FOUR SEASONS BOULEVARD, KISSIMMEE
3 bd · 2.5 ba · 2,360 sqft
Every active listing inside the Four Seasons At Orlando boundary
Open full map search →Find your fit
Browse Four Seasons At Orlando
By feature — on the live map
Where the market lives
The numbers that matter
The Four Seasons At Orlando market
34
Sold, last 12 months
$481,000
Median sold price
97%
Sale-to-list ratio
What sellers actually get vs asking
91 days
Median time to sell
Four Seasons At Orlando vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 0.7% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Four Seasons At Orlando boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Four Seasons At Orlando is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Four Seasons At Orlando home
≈ $3,981/mo
$500,000 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$410/mo
Median HOA
From current listings inside the boundary
Population
216
Median age
51
Median income
$80,574
Median home value
$345,500
Beyond the listings
Living in Four Seasons At Orlando
Hobbies & Interests
Top 3% 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.
Lifestyles
Top 4% 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.
Entertainment
Top 15% 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.
Entertainment
Top 19% in the U.S.Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
Relationships
Top 20% 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.
Food & Drink
Top 22% in the U.S.Ingredient Attentive
These folks are conscious about what they eat. They're looking for ingredients that not only taste great, but also have great nutritional benefits.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
Dan Schriver
REALTOR®
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Straight answers
Four Seasons At Orlando FAQs
Is Four Seasons At Orlando a good place to live?+
It's a gated Osceola County community that trades a condo-style lifestyle for single-family space, with most of the 20 active listings inside the gates. You're close to the theme park corridor — about 24 minutes to Disney — while still living in a quieter residential pocket of Kissimmee. Assigned schools include Westside K-8 and Celebration High School.
Is it expensive to buy here?+
The median list price is $500,000, with homes ranging from $293,000 up to $749,000, so there's room across budgets. At an average of $254 per square foot for roughly 2,000-square-foot homes, pricing is in line with other gated communities in the area.
What do homes cost in Four Seasons At Orlando?+
Over the last 12 months, 34 homes sold at a median price of $481,000, which sits just under the current $500,000 median list price. That gap is normal — sellers are getting about 97% of asking, so the market is pricing close to reality.
How is the market right now?+
It's active and quick: 20 homes are for sale and the typical listing goes under contract in about 20 days. With 34 sales in the past year and sellers averaging 97% of asking, this is a market where fairly priced homes move fast, much like nearby Lake Marion Village.
What about HOA fees and property taxes?+
The median HOA runs about $410 per month, which covers the gated-community services you'd expect. Median property taxes come in around $8,726 per year, so factor both into your monthly carrying cost when you're comparing homes.
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.
Never miss a listing
New Four Seasons At Orlando homes, in your inbox
A daily digest of new Kissimmee listings — straight from the MLS. Unsubscribe anytime.