Windward Cay
Homes for Sale in Kissimmee, FL
All 2,887 homes for sale in Kissimmee, FL · median $374,999 · 781 homes for sale in 34746 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Over the 12 months ending 2026-09-20, 5 recorded sales closed at a median of $340,000, $244 per square foot, a median 93 days on market, sellers accepting 91% of original asking (-10% versus the prior year). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,180 ($4,580 with the full homestead exemption).
| Location | Kissimmee, Osceola County, FL · ZIP 34746 |
|---|---|
| Homes in the community | 144 (FL DOR 2025 assessment roll) |
| Years built | 1991–1998 (median 1992.0) |
| Typical living area | 1,780 sq ft (median) |
| Sale prices, last 12 months | $340,000 median across 5 closed sales · $244 per sq ft · -10.5% vs the prior 12 months |
| Days on market (closed sales) | 93 median |
| Owner-occupied (homestead) share | 52% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2006 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Windward Cay Unit I key facts,” movewithmomentum.com/neighborhoods/windward-cay-unit-i, data as of September 20, 2026.
Windward Cay right now
🔴 Off the recent peak. The trailing-12-month median ($340K) is down 10.5% from the prior 12 months ($380K). With about 4 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Low (5 and 3 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 5, 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 Windward CayHomes for Sale in Kissimmee, FL 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
Windward Cay market snapshot (as of September 20, 2026): the median sale price is about $340K ($244 per sq ft over the trailing 12 months of closed sales), and a median 93 days on market for closed sales. The trailing-12-month median is down 10% from the prior 12 months, computed from record-level Stellar MLS closed sales (5 closings in the current window).
In ZIP 34746 (Kissimmee), 1,623 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.3% year over year, with a median 67 days on market. Right now 435 active and 80 pending listings put supply at about 6.7 months — a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.
County records show 9 qualified sales in Windward Cay across 2024–2025 (8 in 2024, 1 in 2025), median $358,900 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Windward Cay is a community of 144 homes in Kissimmee, Osceola County, built between 1991 and 1998 (median 1992.0), with a median living area of about 1,780 square feet. 52% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($340K) IS the median in the snapshot above, and the move from 2025 ($380K) IS the -10.5% one-year change.
Windows contain 0 to 12 sales each (5 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 2006 through 2026. Deemed reliable but not guaranteed.
16% of homes for sale in ZIP 34746 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 (2026-09-20).
Housing distress & ownership in Windward Cay Unit I, 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.
The Windward Cay buying strategy.
If we were buying in Windward Cay 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 Windward Cay.
A closer look at the Windward Cay market
At a median of $244 per square foot, Windward Cay prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
The trailing-12-month median down 10% year over year. Homes that do trade take a median 93 days on market, useful leverage on any listing that has lingered.
The housing stock is 144 homes built between 1991 and 1998, and 52% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Windward Cay. 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 Windward Cay 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 (4.2). Basis: Recent Direction -10.5% year-over-year; Owner Commitment 52% owner-occupied; Pricing Power 90.9% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
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 Windward Cay 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 Windward Cay sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windward Cay, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windward Cay home worth?
Get a no-obligation home value based on real comparable sales in Windward Cay, 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 Windward Cay?
How long do homes in Windward Cay take to sell?
How many homes are in Windward Cay?
What share of Windward Cay is owner-occupied?
When were the homes in Windward Cay built?
Who is the best real estate agent for Windward Cay?
How do I find a top Kissimmee real estate agent who knows Windward Cay?
Can Momentum Realty connect me with an agent for Windward Cay?
Where is Windward Cay, and what county is it in?
Is Windward Cay a good place to live?
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (5 streets, ZIP 34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2006 (62 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 Windward Cay Unit I fits the bigger picture — live prices, inventory, and Momentum Scores:
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