Windward Cay Unit 02
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Windward Cay Unit 02 is a small, built-out pocket of 94 homes in Kissimmee, all dating to a tight window between 1991 and 1998. With that little construction spread, the median year built lands around 1993 and the median footprint sits near 1,731 square feet. What moves price here is not vintage or size — those are broadly consistent — but condition and updates. A renovated home and an original one can sit far apart on price, so the single median figure hides a wide, condition-driven spread.
There were no closings in the current window, which means recent comps are thin and pricing takes more judgment than a busy street would. For sellers, that puts the burden on presentation and correct list strategy; for buyers, it means you lean on the fundamentals of the individual house rather than a stack of fresh sales to anchor a number.
Who Windward Cay Unit 02 is best for.
Best for
- Buyers seeking a modest, single-story-era 1990s home around 1,731 square feet without paying for new construction
- Value-minded buyers willing to buy an original home and update it to capture the condition-driven spread
- Long-hold owner-occupants who want a small, established enclave with limited turnover
Probably not for
- Buyers who require newer builds or larger square footage than the mid-'90s stock provides
- Anyone who needs a deep stack of recent sales to feel confident on price
- Investors chasing rapid turnover or frequent inventory to trade in and out of
The market around Windward Cay Unit 02
Windward Cay Unit 02 is a small community — 9 recorded sales on file, most recently in 2023 — too few for its own price trend. Here is the market around it.
Across Osceola County, 4,370 homes are active and 1,137 pending (21% under contract).
Homes here are single family residence.
ZIP and county figures describe the wider market, not Windward Cay Unit 02 specifically. Momentum Research analysis of MLS records.
The Windward Cay Unit 02 buying strategy.
If we were buying in Windward Cay Unit 02 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 02.
A built-out enclave where condition writes the price
With 94 homes and a construction range of just 1991 to 1998, Windward Cay Unit 02 offers a consistent product: mid-'90s builds averaging around 1,731 square feet of living space. That consistency is useful — you know roughly what you are buying — but it also means the differentiator between two homes is almost entirely upkeep, systems age, and renovation, not floor plan novelty.
Homestead share sits near half, which points to a mix of owner-occupied homes and non-homesteaded ones. That blend matters at resale: it signals the community isn't monolithic in how homes are held, and a buyer should confirm the tax posture on any specific property rather than assume the median applies to it.
The location and the amenities are priced into every listing in Windward Cay Unit 02. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a small community with no recent closings, the price is made by reading the individual house against dated comps and current condition — not by copying the last sale. We do that reading honestly, tell you where a home's updates justify the ask and where they don't, and price or offer accordingly rather than guessing at a round number.
Windward Cay Unit 02 in 15 seconds.
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 02 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 02 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 02, 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 02 home worth?
Get a no-obligation home value based on real comparable sales in Windward Cay Unit 02, 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 02 on the map →
Frequently Asked Questions
How many homes are in Windward Cay Unit 02?
What share of Windward Cay Unit 02 is owner-occupied?
When were the homes in Windward Cay Unit 02 built?
Do cash buyers compete in Windward Cay Unit 02?
Who is the best real estate agent for Windward Cay Unit 02?
How do I find a top Kissimmee real estate agent who knows Windward Cay Unit 02?
Can Momentum Realty connect me with an agent for Windward Cay Unit 02?
Should you buy in Windward Cay Unit 02?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (3 streets, ZIP 34746)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2015 (14 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 your area comps.
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