Windward Cay
Homes for Sale in Kissimmee, FL
All 2,933 homes for sale in Kissimmee, FL · median $373,400 · 569 homes for sale in 34746 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Over the 12 months ending 2026-07-13, 3 recorded sales closed at a median of $330,000, $244 per square foot, a median 93 days on market, sellers accepting 91% of original asking. At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,030 ($4,430 with the full homestead exemption).
Windward Cay is a small, single-phase pocket of 86 homes built between 1991 and 1998, so the housing stock reads as a fairly tight age band rather than a mix of eras. With a median price of $330,000 against a median price per square foot of $244.20, value here is driven mostly by individual condition and updates rather than by lot premiums or added community infrastructure — there are no amenities identified from current MLS listings, so buyers are paying for the home itself, not a clubhouse or gate.
A median of 93 days on market signals this is not a snap-decision community; homes take real time to find their buyer, which gives sellers reason to price realistically from day one and gives buyers room to negotiate rather than rush. With only three closings in the most recent window, pricing conclusions should be treated as directional, not a guarantee of where the next sale will land.
Nearby homes for sale
No active listings inside Windward Cay Unit 2 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 July 13, 2026): the median sale price is about $330K ($244 per sq ft over the trailing 12 months of closed sales), and a median 93 days on market for closed sales.
Windward Cay is a community of 86 homes in Kissimmee, Osceola County, built between 1991 and 1998 (median 1993.0), with a median living area of about 1,722 square feet. 50% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Windward Cay is a compact, established Kissimmee community of 86 homes from the early-to-mid 1990s, with a median living area of roughly 1,721 square feet and a homestead share of about half the homes — a mix of owner-occupied and non-homestead ownership that's worth understanding before you buy or list.
Who Windward Cay is best for.
Best for
- Buyers comfortable evaluating an individual home on its own merits rather than relying on shared community amenities
- Buyers with flexibility on timeline who can wait through a market that historically runs closer to 90-plus days to sell
- Buyers targeting a home near the community's median size and price point who want an established, mid-1990s-built property
Probably not for
- Buyers who want clubhouse, pool, or other on-site community amenities as part of the purchase
- Sellers expecting a quick sale without pricing to the community's historical days-on-market pattern
- Buyers relying on a large recent-sales dataset to validate pricing, given the limited number of closings in the current window
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 small sample, a real market
At 86 homes total, Windward Cay is small enough that a handful of sales can shift the read on pricing from one quarter to the next. The median year built of 1993 places most of the stock in a narrow construction window, which means differences in price tend to come down to renovation level, maintenance, and layout rather than era of construction.
The median days-on-market figure of 93 is the number to sit with. It suggests homes here don't move on curb appeal alone — buyers are taking time to compare, and sellers who price aggressively out of the gate are more likely to see that reflected in a longer listing period. With no community amenities identified in current listings, the appeal of any given home rests on the property itself: size, condition, and how it's priced relative to that $330,000 median.
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.
Why work with Momentum here
In a community this small, with only three closings in the current window, pricing a home well means reading the handful of comparable sales correctly rather than leaning on broad Kissimmee averages that don't reflect this specific pocket of 86 homes. We track Windward Cay at that granular level so sellers price to the real local trend and buyers know when an asking price is out of step with what the community has actually supported.
Windward Cay in 15 seconds.
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.
See homes for sale in Windward Cay on the map →
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?
Do cash buyers compete in Windward Cay?
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?
Should you buy in Windward Cay?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 13, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2024 (5 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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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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