Homes for sale · Kissimmee, FloridaSeasons
Gated living minutes from the Disney gates
29
Homes for sale
$474,999
Median list price
$246
Avg price / sqft
51
Median days on market
Seasons sits in the vacation-home corridor of Kissimmee, close enough to the theme parks that a Disney morning is a 25-minute drive and far enough to feel like a residential community rather than a tourist strip. The majority of homes here sit behind gates, with pools a common feature, so it draws a mix of year-round families and owners who want a property that works as both a home and a short-term rental. If you want proximity to the parks without being on top of them, this is the stretch of Kissimmee that balances both.
The market here is steady and mid-priced: 29 homes are active with a median list of $474,999, and over the past year 40 sales closed at a median of $481,000, with sellers collecting about 98% of asking. Expect a well-kept community with HOA fees and property taxes that reflect the amenities and the vacation-rental zoning, so run those numbers early. Nearby communities like Storey Lake and Solara give a sense of how this corridor is built and priced.
Seasons is a community in Kissimmee, Florida.
Quick facts
$270,000 – $749K price range
1,940 sqft median home
$407/mo median HOA
$2,750/mo median rent
38 sold in 12 months
Drive times
Living in Seasons
Seasons is part of the vacation-home belt that defines much of western Osceola County, where the pull of the theme parks shapes how neighborhoods are built and who lives in them. The community leans toward gated layouts and pool homes, giving it a resort-adjacent feel while still functioning as a place people call home. It draws a mix of year-round families, remote workers who value park proximity, and owners who run their properties as short-term rentals when they're not using them.
The location is the central selling point. Walt Disney World is roughly 25 minutes away, and the broader tourism infrastructure — restaurants, shops, and highways built for millions of visitors — surrounds the area. That means daily conveniences are plentiful, though the trade-off is living in a corridor where tourist traffic is a steady background fact of life.
This community suits buyers who want that proximity packaged inside a gated, amenity-oriented setting rather than a standalone subdivision. If your priority is a quiet, purely residential street with no vacation-rental activity, you'll want to weigh that carefully. But for families and investors who value access and a managed community, Seasons fits a clear niche.
Neighborhoods and communities in Seasons
Seasons sits among a cluster of well-known communities along the Kissimmee vacation-home corridor, each with its own character and amenity set. Storey Lake is one of the more recognizable names in the area, built around resort-style amenities and popular with short-term rental owners. Solara follows a similar model, pairing newer homes with community features designed for both residents and vacation guests.
Further afield, Solivita represents a different flavor of community living in the region, and Lake Marion Village adds to the range of options buyers compare when shopping this part of Osceola County. Windsor at Westside is another name in the same orbit of resort-style neighborhoods along the corridor.
When comparing these communities, pay attention to how each handles HOA scope, amenities, and short-term rental rules, since those vary and directly affect your costs and how you can use the home. Touring a few side by side is the fastest way to understand where Seasons lands on price and feel relative to its neighbors.
Homes for sale in Seasons: prices and housing
The current market shows 29 active listings with a median list price of $474,999 and a range running from $270,000 to $749,000. Over the past 12 months, 40 homes sold at a median price of $481,000, and sellers averaged about 98% of their asking price — a sign of a market that holds value without heavy discounting. The average cost is roughly $246 per square foot, on a median home size of 1,940 square feet.
The housing mix leans gated: 18 of the 29 active listings sit behind gates, and seven include a private pool. There is one waterfront listing active, no golf-course or 55+ product in the current set, and no listings above $1 million. There's also no new construction currently active in Seasons itself, so most purchases here are resale homes.
Carrying costs deserve a close look. The median HOA fee is about $407 per month, reflecting the gated access and amenities, and median property taxes run around $7,310 per year. For context on the rental side, the median rent in the area is about $2,750 per month, which matters if you're evaluating the property as an investment or short-term rental.
Schools in Seasons
The schools most commonly assigned to this area include Central Avenue Elementary School, Kissimmee Middle School, and Poinciana High School, with Osceola County School for the Arts also serving students in the broader zone. These assignments give you a starting point, but they are not guaranteed for every address within or near the community.
School attendance boundaries in Osceola County can and do change, and they're set by address rather than by community name. Before making an offer, verify the exact zoned schools for the specific property with the Osceola County School District. This is especially important if school assignment is a deciding factor in your purchase.
If you're weighing specialized programs, confirm eligibility and application requirements directly, since magnet and arts-focused schools often follow different enrollment rules than standard neighborhood schools. Treat the district's official zone lookup as the final word.
Getting around Seasons
Seasons benefits from its position in a well-connected tourism corridor. Walt Disney World is about a 25-minute drive, Universal Orlando roughly 38 minutes, and Downtown Orlando around 40 minutes, putting the region's major destinations within reasonable reach. Orlando International Airport is approximately 33 minutes away, which is convenient for frequent travelers and for owners managing out-of-town guests.
The area relies on the major highways that thread through western Osceola County, feeding toward I-4 and the broader Orlando road network. Those routes carry heavy tourist volume, so travel times can stretch during peak periods around holidays and school breaks.
This is a car-dependent area, as most of suburban Central Florida is. Plan on driving for daily errands, work commutes, and park trips, and factor peak-season traffic into your expectations if you're used to lighter roads.
Is Seasons a good place to live?
For the right buyer, Seasons delivers a clear value proposition: a gated, amenity-oriented community within 25 minutes of Disney, priced in the mid-market with a median around $474,999. The steady sales pace — 40 closings in the past year at 98% of asking — points to a market that holds its value, and the pool-heavy, gated inventory appeals to both families and short-term rental owners.
The trade-offs are real and worth naming. HOA fees near $407 per month and property taxes around $7,310 per year add meaningful carrying costs, and living in a tourism corridor means steady traffic and an active vacation-rental presence among your neighbors. There's also no new construction currently in the community, so buyers wanting the newest product may need to look at adjacent neighborhoods.
Overall, Seasons makes sense if you value park proximity inside a managed, gated setting and you've run the full monthly math on HOA and taxes. It's less of a fit if you want a quiet, purely residential street or new-build inventory. Comparing it directly against neighbors like Storey Lake and Solara is the best way to confirm it's the right spot for you.
On the market now
Homes for sale in Seasons
View all 29 →
$474,999
1315 SEASONS BOULEVARD, KISSIMMEE
6 bd · 5.5 ba · 2,901 sqft
$499,900
7789 FOUR SEASONS BOULEVARD, KISSIMMEE
3 bd · 2.5 ba · 2,360 sqft
$360,000
2043 KEY BAY TRAIL, KISSIMMEE
2 bd · 2 ba · 1,557 sqft
$575,000
1999 LIMESTONE TRAIL, KISSIMMEE
3 bd · 2 ba · 2,202 sqft
$370,000
1915 FLORA PASS PLACE, KISSIMMEE
2 bd · 2 ba · 1,557 sqft
$378,000$399,900
1999 KEY BAY TRAIL, KISSIMMEE
2 bd · 2 ba · 1,583 sqft
$575,000
7890 STONEY BAY LOOP, KISSIMMEE
3 bd · 2 ba · 2,042 sqft
$565,000$575,000
1900 ESTUARY LANE, KISSIMMEE
3 bd · 2 ba · 2,202 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
$457,000$460,000
3058 CADENCE SOUND LANE, KISSIMMEE
4 bd · 2 ba · 1,848 sqft
$349,500
1987 KEY BAY TRAIL, KISSIMMEE
2 bd · 2 ba · 1,437 sqft
Every active listing inside the Seasons boundary
Open full map search →Find your fit
Browse Seasons
By feature — on the live map
Where the market lives
The numbers that matter
The Seasons market
38
Sold, last 12 months
$477,500
Median sold price
98%
Sale-to-list ratio
What sellers actually get vs asking
79 days
Median time to sell
Seasons vs Kissimmee
Median list price
Price per sqft
Days on market
Median sold price — 3-yr, 3-mo rolling
▼ 8.0% yr/yr
Homes sold per month
Live Stellar MLS data — every listing and closed sale inside the Seasons boundary. Rolling medians smooth single-month swings in small communities.
For the school run
Schools Seasons is zoned for
Attendance boundaries overlapping this community — always verify zoning with the district.
What it really costs
Owning here
Owning the median Seasons home
≈ $3,729/mo
$474,999 median · 20% down · 30-yr fixed at 6.9% · taxes/HOA from live listing data · insurance is a Florida estimate.
$407/mo
Median HOA
From current listings inside the boundary
$2,750/mo
Median rent
Homes for rent inside the boundary
Population
595
Median age
42
Median income
$88,125
Median home value
$418,700
Beyond the listings
Living in Seasons
Lifestyles
Top 7% 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.
Hobbies & Interests
Top 9% 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.
Attitudes
Top 16% 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.
Food & Drink
Top 17% 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.
Emotional
Top 25% in the U.S.Happy Place
Expressing feelings of safety, comfort and happiness - especially with loved ones.
Entertainment
Film Lovers
Movie buffs and binge watchers expressing their love for movies, storytelling, and the film making process.
People who close here
Our Kissimmee experts
Iain Robinson
Broker Associate
David Ramirez
Real Estate Agent
Colleen Brown
REALTOR®
Nicholas Giaccone
Director of Agent Success
Straight answers
Seasons FAQs
Is Seasons a good place to live?+
It suits buyers who want a gated, amenity-minded community close to the theme parks, with 18 of 29 active listings behind gates and pools on many homes. The 25-minute drive to Walt Disney World and quick access to MCO make it practical for families and rental owners alike. It's less ideal if you want a quiet, purely residential street with no vacation-rental activity nearby.
Is Seasons expensive?+
It's mid-market for the Kissimmee area, with a median list price of $474,999 and sales ranging from $270,000 to $749,000. The average cost runs about $246 per square foot on a median home size of 1,940 square feet. There are currently no listings over $1 million, so this is not a luxury enclave.
What do homes cost in Seasons?+
Active listings range from $270,000 to $749,000 with a median list of $474,999, while homes that sold over the past 12 months closed at a median of $481,000. At roughly $246 per square foot, a typical 1,940-square-foot home lands near the median. Nearby Solara offers a useful comparison for how the vacation-home corridor is priced.
How is the market in Seasons?+
It's balanced and steady — 29 homes are active and 40 sold in the past year, with a median of 46 days on market. Sellers are getting about 98% of their asking price, so well-priced homes move without heavy negotiation. Buyers have selection but shouldn't expect deep discounts on move-in-ready listings.
What are the HOA fees and property taxes?+
The median HOA fee here runs about $407 per month, which reflects the gated access and community amenities common in this corridor. Median property taxes are around $7,310 per year, partly a function of the vacation-rental zoning in the area. Budget for both when you compare monthly carrying costs against nearby Storey Lake.
What schools serve Seasons?+
The most commonly assigned schools include Central Avenue Elementary, Kissimmee Middle School, and Poinciana High School, with Osceola County School for the Arts also serving the area. School zones can change, so confirm the exact assignment for any specific address with Osceola County Schools before you buy. Attendance boundaries are the deciding factor, not just proximity.
How is the commute from Seasons?+
Orlando International Airport is about 33 minutes away and Downtown Orlando roughly 40 minutes, making this workable for commuters and frequent travelers. Universal Orlando is around 38 minutes and Walt Disney World about 25. Major routes toward I-4 and the 429 keep most of the region within a reasonable drive.
Is there new construction in Seasons?+
There are currently no new-construction listings active in Seasons itself, so most purchases here are resale homes. Buyers wanting newer builds often look to adjacent communities along the same corridor, such as Solivita or other parts of Kissimmee. It's worth comparing resale value against newer inventory nearby before deciding.
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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