Windward Cay Unit I
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
Windward Cay Unit I right now
🔴 Off the recent peak. The trailing-12-month median ($340K) is down 8.0% from the prior 12 months ($369K). 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 July 15. Confidence: Low (5 and 4 sales in the two windows).
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Updated July 15, 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
Windward Cay Unit I market snapshot (as of July 15, 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 8% from the prior 12 months, computed from record-level Stellar MLS closed sales (5 closings in the current window).
Windward Cay Unit I 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 July 15 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 ($369K) IS the -8.0% 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 %s through %s. Deemed reliable but not guaranteed.
The Windward Cay Unit I buying strategy.
If we were buying in Windward Cay Unit I 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 Unit I.
A closer look at the Windward Cay Unit I market
At a median of $244 per square foot, Windward Cay Unit I 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 8% 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 Unit I. 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 Unit I 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 (4.4). Basis: Recent Direction -8.0% year-over-year; Owner Commitment 52% owner-occupied; Pricing Power 90.9% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA — confirm current dues
- 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 Unit I 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 Unit I 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 Unit I, 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 Unit I home worth?
Get a no-obligation home value based on real comparable sales in Windward Cay Unit I, 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 Windward Cay Unit I on the map →
Frequently Asked Questions
What is the median home price in Windward Cay Unit I?
How long do homes in Windward Cay Unit I take to sell?
How many homes are in Windward Cay Unit I?
What share of Windward Cay Unit I is owner-occupied?
When were the homes in Windward Cay Unit I built?
Do cash buyers compete in Windward Cay Unit I?
Who is the best real estate agent for Windward Cay Unit I?
How do I find a top Kissimmee real estate agent who knows Windward Cay Unit I?
Can Momentum Realty connect me with an agent for Windward Cay Unit I?
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 15, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (5 streets, ZIP 34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2006 (60 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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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 your area comps.
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