Windsor at Westside; Windsor/Westside
Homes for Sale in Kissimmee, FL
All 3,127 homes for sale in Kissimmee, FL · median $375,000 · 797 townhomes for sale in Kissimmee · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, Windsor at Westside; Windsor/Westside in Kissimmee, FL has 3 homes for sale. Homes listed or recently sold were built 2019 - 2019; 3 of 3 report an HOA (median $584/mo); none of the 3 geocoded homes sit in a FEMA special flood hazard zone (median elevation 123 ft).
Homes For Sale Right Now in Windsor at Westside; Windsor/Westside
Live MLS inventory for Windsor at Westside; Windsor/Westside. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Windsor at Westside; Windsor/Westside listings as of 2026-10-26, priced high to low. Based on Stellar MLS data distributed by MLS GRID. Tap any home to ask about it.
Windsor at Westside is a gated, resort-style community in Kissimmee with a deep amenity package - clubhouse, pool, spa, fitness center, tennis, trails, and guard-gated entry. In a community like this, price is driven less by location alone and more by a home's condition, size, and furnishing status. With only 3 active listings as of August 2026, the visible inventory is thin, which means each listing carries outsized weight in setting the tone.
For buyers, a shallow pool of choices rewards decisiveness and patience in equal measure - you may wait for the right floor plan rather than negotiate hard across many options. For sellers, scarce competition can help, but the amenity-heavy profile means your home is being compared on presentation and condition, not just address. Price the home to the comps and the condition, not to the HOA brochure.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
The 60-Second Overview
This is a guard-gated, amenity-rich community in the Westside corridor of Kissimmee, Osceola County, built around resort-style common areas rather than a single home type.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
The setting & the homes.
Aerial and on-site photos of Windsor at Westside; Windsor/Westside. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Windsor at Westside; Windsor/Westside
Windsor at Westside; Windsor/Westside
Windsor at Westside; Windsor/WestsidePhotos from Stellar MLS listings in Windsor at Westside; Windsor/Westside; content deemed reliable but not guaranteed.
Who Windsor at Westside; Windsor/Westside is best for.
Best for
- Buying to use a resort-style amenity set as part of daily living
- Looking for a guard-gated community in the Kissimmee Westside corridor
- Willing to wait for the right floor plan given limited active listings
Probably not for
- Wanting minimal HOA rules and low monthly dues
- Needing a broad selection of homes to compare on short notice
- Seeking a community without resort amenities and their associated costs
The market around Windsor at Westside; Windsor/Westside
Windsor at Westside; Windsor/Westside is too small for its own price trend, so here is the market around it.
Across Osceola County, 4,396 homes are active and 1,122 pending (20% under contract).
ZIP and county figures describe the wider market, not Windsor at Westside; Windsor/Westside specifically. Momentum Research analysis of MLS records.
Windsor at Westside; Windsor/Westside on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap contributors.
Life at Windsor at Westside; Windsor/Westside
- Clubhouse · reported on 3 of 3 listings
- Fitness Center · reported on 3 of 3 listings
- Gated · reported on 3 of 3 listings
- Park · reported on 3 of 3 listings
- Playground · reported on 3 of 3 listings
- Pool · reported on 3 of 3 listings
- Tennis Court(s) · reported on 3 of 3 listings
- Trail(s) · reported on 3 of 3 listings
- Gated Community - Guard · reported on 3 of 3 listings
- Spa/Hot Tub · reported on 1 of 3 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
The Windsor at Westside; Windsor/Westside buying strategy.
If we were buying in Windsor at Westside; Windsor/Westside 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 Windsor at Westside; Windsor/Westside.
A guard-gated resort build
The amenity list here is unusually full for a residential community: clubhouse, fitness center, pool, spa/hot tub, tennis courts, a park, playground, and trails, all behind a guarded gate. That infrastructure signals an HOA with real responsibilities and ongoing cost, so the dues and the rules matter as much as the house. Confirm current fees, access, and any rental or usage restrictions directly with the HOA before you write an offer.
Because the community leans into short-term-rental territory common to the Westside corridor, condition and furnishing status can swing value meaningfully from one listing to the next. Treat each of the small handful of active homes individually; two units with the same square footage can sit at different places on price depending on turnkey readiness.
The location and the amenities are priced into every listing in Windsor at Westside; Windsor/Westside. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
With inventory this thin, the value is in knowing which of the few listings is actually priced to its condition and which is coasting on the amenity list. We read the comps against furnishing, upkeep, and HOA terms, and we verify access and fees with the association so you are not guessing at carrying costs. On the sell side, we position your home on presentation, where it competes, not on the brochure.
Windsor at Westside; Windsor/Westside in 15 seconds.
Tools for a Windsor at Westside; Windsor/Westside 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 Windsor at Westside; Windsor/Westside sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor at Westside; Windsor/Westside, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Windsor at Westside; Windsor/Westside home worth?
Get a no-obligation home value based on real comparable sales in Windsor at Westside; Windsor/Westside, 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 all homes for sale in Kissimmee →
Should you buy in Windsor at Westside; Windsor/Westside?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 26, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-08-18 |
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. A Momentum agent can price yours against live local comps.
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See how WINDSOR AT WESTSIDE; WINDSOR/WESTSIDE fits the bigger picture — live prices, inventory, and Momentum Scores:
Email me new listings in Windsor at Westside; Windsor/Westside
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Windsor at Westside; Windsor/Westside
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windsor at Westside; Windsor/Westside will answer, and the answer is published on this page for the next buyer.
What it really costs to own in Windsor at Westside; Windsor/Westside
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| CDD / special assessments | Listings here report a median of $1,144/yr in CDD or special-district assessments on the tax bill (3 listings, MLS, 2026-11-14). The amount is per lot and set by the district: confirm it on the parcel's TRIM notice. |
|---|---|
| HOA dues | Median $584/month across 3 MLS listings (most billed monthly; 2026-11-14). Dues cover what the documents say they cover; ask for the budget and reserve study. |
| Home and flood insurance | The average Citizens Property Insurance premium in Osceola County is $1,735/yr (2,188 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. |
| Roof and age | Median build year 2019 across 3 listings. Newer roofs and current wind-mitigation features usually mean the lower end of insurance quotes. |
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Osceola County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Osceola County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.