Seasons at Big Sky
Homes for Sale in Kissimmee, FL
All 2,944 homes for sale in KISSIMMEE, FL · median $373,250 · 333 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
As of October 2026, Seasons at Big Sky in Kissimmee, FL has 6 homes for sale and 1 pending, asking from $345,000 to $559,999 (median $479,000). Over the 12 months ending 2026-08-02, 7 recorded sales closed at a median of $557,000, $188 per square foot, a median 150 days on market, sellers accepting 100% of original asking (+13% versus the prior year). Homes listed or recently sold were built 2023–2025 with 7 new construction; 16 of 16 report an HOA (median $80/mo); none of the 16 geocoded homes sit in a FEMA special flood hazard zone (median elevation 68 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $8,480 ($7,880 with the full homestead exemption).
| Location | KISSIMMEE, Osceola County, FL · ZIP 34744 |
|---|---|
| Homes in the community | 275 (FL DOR 2025 assessment roll) |
| Years built | 1940–2024 (median 2024) |
| Typical living area | 2,388 sq ft (median) |
| Home types (current listings and sales) | single-family 94%, townhouses 6% |
| Amenities listed by sellers | Pool, Playground, Trail(s), Tennis Court(s), Park, Pickleball Court(s) |
| Sale prices, last 12 months | $557,000 median across 7 closed sales · $188 per sq ft · +13.1% vs the prior 12 months |
| Days on market (closed sales) | 150 median |
| Owner-occupied (homestead) share | 56% |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2023 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “SEASONS AT BIG SKY key facts,” movewithmomentum.com/neighborhoods/seasons-at-big-sky, data as of August 2, 2026.
Last 30 days in Seasons at Big Sky: 3 new listings (median asking $460,000), 1 under contract right now. As of October 2, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
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 and pending Seasons at Big Sky listings as of 2026-10-01, 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.
Every Home for Sale in Seasons At Big Sky Right Now (7)
All 7 active and pending Seasons At Big Sky listings with a detail page, newest first, refreshed twice a day from the MLS.
- 3058 Cadence Sound Lane · $460,000 · 4 bd / 2 ba · listed Sep 27, 2026 · listed by La Rosa Realty Kissimmee
- 2949 Gavin Sky Drive · $540,000 · 4 bd / 2 ba · listed Sep 21, 2026 · listed by Lpt Realty, Llc
- 1525 Erin Breeze Lane · $459,000 · 3 bd / 2 ba · listed Sep 8, 2026 · listed by Blue Marlin Real Estate
- 2994 Gavin Sky Drive · $559,999 · 5 bd / 3.5 ba · listed Sep 2, 2026 · listed by Charles Rutenberg Realty Orlando
- 1383 Levy Bend Drive · $498,000 · 4 bd / 3 ba · listed Aug 5, 2026 · listed by La Rosa Realty Kissimmee
- 1528 Erin Breeze Lane · $345,000 · 3 bd / 2.5 ba · listed Jul 2, 2026 · listed by Florida Lakes Realty
- 1491 August Gray Drive · $394,900 · 4 bd / 3 ba · pending · listed Jul 2, 2026 · listed by Keller Williams Advantage Iii
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.
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 October 2, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside SEASONS AT BIG SKY right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
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).
In ZIP 34744 (KISSIMMEE), 789 homes closed in the last 12 months at a median of $406K ($215/sq ft), up 1.2% year over year, with a median 33 days on market. Right now 128 active and 26 pending listings put supply at about 6.7 months — a balanced market. See the live ZIP 34744 housing market and the Osceola County market.
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
Photos 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.
18% 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 (2026-10-02).
Seasons At Big Sky Market Scorecard
Seasons At Big Sky is currently a buyer's market. About 8.0 months of supply, a median asking price of $479,000, and homes go under contract in about 28 days.
Typical home value in the 34744 ZIP is $380,668, about 9.9% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. 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 September 2026 through September 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, tiles © CARTO.
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.
Shop the zone: Homes zoned for Gateway High School (9 12)
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.
HOA, CDD & Fees
- HOA dues reported around $80/month (about $960/yr) · median of 262 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $80 per month ($960 a year) — the median AssociationFee across 262 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
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.
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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?
Where is Seasons at Big Sky, and what county is it in?
Is Seasons at Big Sky a good place to live?
Should you buy in Seasons at Big Sky?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 1, 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.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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See how SEASONS AT BIG SKY fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Seasons at Big Sky with Momentum Realty’s local guides.