Windward Cay Unit 1
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
121 homesBuilt 1991–1998
Free · No obligation
Talk to a Windward Cay Unit 1 Expert

True comps, carrying-cost math, and listings before the portals.

Built fromLive Stellar MLS data4 years of closingsFL DOR public recordsUpdated twice daily
Live · Windward Cay Unit 1 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Tempo
2
Sold · last 12 mo
10-yr average: about 1 a year
Ownership and context
53%
Owner-occupied · Windward Cay Unit 1
64 of 121 parcels homesteaded (FL DOR 2025)
47%
Non-owner-occupied · Windward Cay Unit 1
incl. 5% trust or LLC-held · 27% out-of-state
33%
Cash buyers · Windward Cay Unit 1
1 of 3 sales, 12 mo ending June 2025
121
Homes in the community
121 residential parcels (FL DOR 2025)
Track record · 4 years of records
Est. 1991
Community established
homes built 1991-1998, median 1992 (FL DOR 2025)
0
Failed listings · 2025
peaked at 3 in 2025
1.7%/yr
Turnover rate
about 2 of 121 homes trade a year

The market around Windward Cay Unit 1

Windward Cay Unit 1 is a small community — 4 recorded sales on file, most recently in 2025 — 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 1 specifically. Momentum Research analysis of MLS records.

If we were buying in Windward Cay Unit 1 today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 1.

A closer look at the Windward Cay Unit 1 market

The housing stock is 121 homes built between 1991 and 1998, and 53% 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 1. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty

HOA, CDD & Fees

In short
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Windward Cay Unit 1 sales matched to your home.

What is your Windward Cay Unit 1 home worth?

Get a no-obligation home value based on real comparable sales in Windward Cay Unit 1, 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 1 on the map →

Real comps, not an automated estimate.

Frequently Asked Questions

How many homes are in Windward Cay Unit 1?
The Florida DOR 2025 assessment roll shows 121 homes in Windward Cay Unit 1 (public records).
What share of Windward Cay Unit 1 is owner-occupied?
53% of Windward Cay Unit 1 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Windward Cay Unit 1 built?
Homes in Windward Cay Unit 1 were built between 1991 and 1998, with a median year built of 1992 (FL DOR 2025 roll).
Do cash buyers compete in Windward Cay Unit 1?
Cash buyers took 33% of Windward Cay Unit 1 sales in the 12 months ending June 2025 (1 of 3 closings, Stellar MLS).
Who is the best real estate agent for Windward Cay Unit 1?
The best agent for Windward Cay Unit 1 is one who actively works Kissimmee and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Windward Cay Unit 1.
How do I find a top Kissimmee real estate agent who knows Windward Cay Unit 1?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Windward Cay Unit 1 and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Windward Cay Unit 1?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Windward Cay Unit 1 purchase or sale - no call center and no pressure.

Data sources & freshness

Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (3 streets, ZIP 34746))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2022 (6 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.

Looking to buy here? Search homes for sale →

What’s your home worth in your area?

A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.

By submitting, you agree that EAB RE INVESTMENTS LLC (Momentum Realty) and its agents may call, email, and text you about your inquiry, which may involve automated means and prerecorded or artificial voices. You do not need to consent as a condition of buying any property, goods, or services. To opt out, reply STOP at any time or reply HELP for assistance. You can also click the unsubscribe link in emails. Message and data rates may apply. Message frequency may vary. See our Privacy Policy and SMS Terms.or call (904) 351-6461
CallFree valuation →
Talk to a Local Windward Cay Unit 1 Expert
Call Get Listings