Legacy Dunes vs Windsor at Westside
Two Osceola communities, compared on the numbers that decide it — price, pace, and supply — from live MLS data as of 2026-11-12.
| Metric | Legacy Dunes | Windsor at Westside |
|---|---|---|
| Median sale price | $186K | $490K |
| Price per sq ft | $184 | $160 |
| Avg days on market | 177 days | 99 days |
| Months of supply | 3.6 mo | 9.6 mo |
| Market | Buyer-Leaning Market | Buyer's Market |
| 1-year price change | False | False |
| Recent closings | 30 | 95 |
The verdict
Windsor at Westside carries the higher median price — about 163% above Legacy Dunes. Homes in Windsor at Westside sell faster (99 days on market vs 177). Legacy Dunes is the tighter market on inventory (3.6 months of supply).
Where each one is
Legacy Dunes and Windsor at Westside are about 2 miles apart (straight-line, center to center) and share Osceola County.
| Legacy Dunes | Windsor at Westside | |
|---|---|---|
| County | Osceola County, FL | Osceola County, FL |
| City / area | Kissimmee | Kissimmee |
| ZIP | 34747 | 34747 |
| FEMA flood zones (sampled parcels) | not enough parcels sampled | all 67 sampled homes outside a flood zone |
Distances are straight-line; driving distance is usually 15 to 30 percent more. Flood-zone shares come from FEMA flood maps matched to sampled parcels; always check the exact address before you close.
What is for sale today
| Legacy Dunes | Windsor at Westside | |
|---|---|---|
| Homes for sale now | 9 | 76 |
| Under contract | 0 | 9 |
| Asking prices today | $185K to $241K | $380K to $720K |
| Property types listed | Condominium | Single Family Residence, Townhouse |
Live MLS counts, refreshed with every listing pull. Browse them: Legacy Dunes homes for sale · Windsor at Westside homes for sale.
The homes themselves
| Legacy Dunes | Windsor at Westside | |
|---|---|---|
| Homes (parcels) | n/a | 685 |
| Built | n/a | 2015–2020 (median 2018) |
| Typical living area | n/a | 3,433 sq ft |
Housing-stock figures from the Florida Department of Revenue 2025 assessment roll (public records).
Schools the listings are zoned for
| Legacy Dunes | Windsor at Westside | |
|---|---|---|
| Elementary | Westside K-8 | Westside K-8 |
| Middle | Kissimmee Middle | West Side |
| High school | Celebration High | Celebration High |
The school most often recorded on each community's MLS listings. Always confirm a specific address with the district.
Which one fits
On budget alone, Legacy Dunes is the lower entry point (median $186K vs $490K). Sellers get a faster sale in Windsor at Westside (99 days on market on average); buyers get more negotiating room where homes sit longer.
Neither number set decides it: drive both on a weekday evening, check the HOA documents and the flood zone for the exact street, and price the insurance before you write an offer. A Momentum agent who works both communities can pull the comparable sales for any two specific homes.
Questions people ask
Is Windsor at Westside more expensive than Legacy Dunes?
Yes, on recent sales: the median sale price in Windsor at Westside is $490,000 versus $186,000 in Legacy Dunes, about 163% higher.
How far apart are Legacy Dunes and Windsor at Westside?
About 2 miles straight-line, center to center, both in Osceola County; driving distance is usually 15 to 30 percent more.
What high schools serve Legacy Dunes and Windsor at Westside?
Listings in Legacy Dunes most often report Celebration High; listings in Windsor at Westside report Celebration High. Zoning is set by the district and can change - verify by address.
Go deeper on each: Legacy Dunes homes, photos & schools · Windsor at Westside homes, photos & schools
Figures are aggregates from realMLS / DBAAR, updated regularly. Thinking about either? Talk to Momentum Realty.