Seasons at Big Sky
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
Homes For Sale Right Now in Seasons at Big Sky
Live MLS inventory for Seasons at Big Sky. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 52 daysTop listing
Active · 108 daysActive · 3 days
Active · 47 days
Active · 222 days
Under Contract · 131 daysActive and pending Seasons at Big Sky listings as of 2026-11-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2023 through 2026. Tap any home to ask about it.
The number that shapes Seasons At Big Sky is the median days on market: at 227 days, this is a slow, patient market where listings sit and pricing is negotiated over time rather than in a weekend. With a median price of $557,000 and a median around $187 per square foot on roughly 2,293 square feet, price here is driven by condition and specifics more than by a hot bidding floor. The wide construction span — homes built between 1940 and 2024, with the median build year at 2024 — tells you there is real variety underneath that single median, so two homes at similar prices can be very different products.
For sellers, the posture is straightforward: expect a long runway and price to the market from day one, because carrying a listing here means months, not days. For buyers, the slow pace is leverage — there is time to inspect, compare, and negotiate rather than chase. The 15.4% year-over-year move signals momentum in values, but with only 7 closings in the window, individual sales carry outsized weight, so lean on comps for the specific product you are buying, not the headline median.
Figures in this note are as of July 13, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Seasons at Big Sky right now
🟢 Still climbing. The trailing-12-month median ($557K) is up 13.1% from the prior 12 months ($493K).Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Medium (7 and 78 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated August 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Seasons at Big Sky market snapshot (as of August 2, 2026): the median sale price is about $557K ($188 per sq ft over the trailing 12 months of closed sales), and a median 150 days on market for closed sales. The trailing-12-month median is up 13% from the prior 12 months, computed from record-level Stellar MLS closed sales (7 closings in the current window).
Seasons at Big Sky is a community of 275 homes in Kissimmee, Osceola County, built between 1940 and 2024 (median 2024), with a median living area of about 2,388 square feet. 56% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Seasons At Big Sky is a 224-home community in Kissimmee, Osceola County, where a very wide age range of housing sits behind a new-construction-weighted median build year, and where homes trade slowly enough that patience is the operative skill on both sides of the table.
The setting & the homes.
Aerial and on-site photos of Seasons at Big Sky. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Seasons at Big Sky
Seasons at Big SkyPhotos from Stellar MLS listings in Seasons at Big Sky; content deemed reliable but not guaranteed.
Who Seasons at Big Sky is best for.
Best for
- Buyers targeting newer, current-year construction who want the median-price product
- Patient buyers who value negotiating room over speed and can wait for the right listing
- Owner-occupant buyers planning to hold, given the meaningful homestead base
Probably not for
- Sellers who need to close quickly and cannot carry a listing for months
- Buyers chasing a fast, competitive close in a hot-market rhythm
- Short-horizon flippers counting on quick turnover in a 227-day market
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($557K) IS the median in the snapshot above, and the move from 2025 ($493K) IS the +13.1% one-year change.
Windows contain 0 to 78 sales each (7 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2023 through 2026. Deemed reliable but not guaranteed.
19% of homes for sale in ZIP 34744 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-08-01).
Seasons at Big Sky Market Scorecard
Seasons at Big Sky is currently a balanced market., and homes go under contract in about 52 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in SEASONS AT BIG SKY, KISSIMMEE
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period November 2026 through November 2026. Deemed reliable but not guaranteed.
Seasons at Big Sky on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap contributors.
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Partin Settlement Elem · Elementary
- Neptune Middle (6-8) · Middle
- Gateway High School (9 12) · High
Zoned schools reflect the assignments reported on recent Seasons at Big Sky listings and can change; always confirm with Osceola County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Seasons at Big Sky address.
The Seasons at Big Sky buying strategy.
If we were buying in Seasons at Big Sky today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Seasons at Big Sky.
A slow market with a wide product spread
The gap between the oldest and newest homes here is the whole story. With a build range from 1940 to 2024 and a median build year of 2024, the community carries both older stock and current-year construction under one name. That means the median price and the median $187 per square foot are useful as anchors, but the actual value of any given home depends heavily on which end of that spectrum it sits on and how it has been maintained or updated.
About 53% of homes here carry a homestead exemption, which points to a meaningful owner-occupied base rather than a purely investor-driven pool. Combined with a 227-day median time on market, the takeaway is a market that rewards preparation over speed: identify the specific product type you want, study its comps, and be ready to move deliberately when the right one appears.
The location and the amenities are priced into every listing in Seasons at Big Sky. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Seasons at Big Sky buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 3 factors (8.3). Basis: Recent Direction +13.1% year-over-year; Owner Commitment 56% owner-occupied; Pricing Power 100.0% sale-to-list. Refreshed with each data update.
Why work with Momentum here
A market this slow and this varied is where representation earns its keep. With homes spanning eight decades of construction and a low closing count, headline stats can mislead — we work the comps down to the specific vintage and condition you are trading, price for a long runway, and use the slow pace as negotiating leverage rather than a source of anxiety.
Seasons at Big Sky in 15 seconds.
Tools for a Seasons at Big Sky buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Seasons at Big Sky sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Seasons at Big Sky, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Seasons at Big Sky home worth?
Get a no-obligation home value based on real comparable sales in Seasons at Big Sky, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See homes for sale in Seasons at Big Sky on the map →
Recent Developments in Seasons At Big Sky
Development, infrastructure, retail, and school activity affecting Seasons At Big Sky, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated November 2026.
- October 2026Parks & Amenities
145,000 sq ft All Sports Dome planned on Gus Road in Kissimmee
All Sports Dome Southeast plans a climate-controlled indoor inflatable dome at 3070 Gus Road with multi-sport courts, turf fields and training areas. It would be the brand's first Greater Orlando location, with an opening expected in 2027 and no exact date given.
What it may mean for the marketAn indoor sports venue would add year-round recreation and event space on Kissimmee's Gus Road area. The project is about 9 miles west of Seasons At Big Sky, elsewhere in Osceola County.
Source: What Now Orlando - October 2026Infrastructure
Turnpike widening in Osceola County runs ahead of schedule at Fortune Road Bridge
Steel beams for the new westbound Fortune Road Bridge are in place a month early as Florida's Turnpike is widened from two to four lanes each way between Partin Settlement Road and Osceola Parkway. Westbound bridge traffic is expected at the start of 2027, and the broader project targets 2031. The bridge adds bike lanes and sidewalks.
What it may mean for the marketDoubling Turnpike capacity through this stretch should ease regional commutes between Kissimmee and the Orlando area once complete. The site is about 5 miles west of Seasons At Big Sky.
Source: WFTV - October 2026Development
Experience Kissimmee launches Film Kissimmee commission to recruit productions
The new film commission markets Osceola County to production companies through an online database of more than 100 filming locations and has hired a location manager. Leaders say productions could become a new economic driver, citing spending on hotels, vehicles, food and crew services.
What it may mean for the marketFilm work could add temporary jobs and visitor spending for hospitality and service businesses across Osceola County. The site is about 6 miles west of Seasons At Big Sky.
Source: WFTV - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The site is about 8 miles northeast of Seasons At Big Sky.
Source: Spectrum News 13 - August 2026Civic
St. Cloud council approves $6.7 million downtown apartment and parking garage agreement
The City Council unanimously approved an agreement with Atlantic Housing Partners for apartments and a parking garage next to City Hall. The Community Redevelopment Agency contributes $6.25 million and the city $460,000. The garage would hold 450 to 500 spaces, with 250 reserved for apartment residents.
What it may mean for the marketNew downtown rental housing and public parking would add residents and parking capacity to the St. Cloud core. The site is about 4 miles south of Seasons At Big Sky.
Source: Spectrum News 13 - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 5 miles north of Seasons At Big Sky.
Source: ClickOrlando
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
Frequently Asked Questions
What is the median home price in Seasons at Big Sky?
How long do homes in Seasons at Big Sky take to sell?
How many homes are in Seasons at Big Sky?
What share of Seasons at Big Sky is owner-occupied?
When were the homes in Seasons at Big Sky built?
Do cash buyers compete in Seasons at Big Sky?
Who is the best real estate agent for Seasons at Big Sky?
How do I find a top Kissimmee real estate agent who knows Seasons at Big Sky?
Can Momentum Realty connect me with an agent for Seasons at Big Sky?
Should you buy in Seasons at Big Sky?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near Seasons at Big Sky with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: November 12, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (10 streets, ZIP 34744)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2023 (146 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
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