Windsor at Westside; Windsor/Westside
Homes for Sale in Kissimmee, FL
All 2,920 homes for sale in KISSIMMEE, FL · median $374,990 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 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).
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.
WINDSOR AT WESTSIDE; WINDSOR/WESTSIDE Market Scorecard
WINDSOR AT WESTSIDE; WINDSOR/WESTSIDE is currently a thin data market. Limited supply, a median asking price of $445,000, and homes go under contract in about 36 days.
Typical home value in the 34747 ZIP is $400,438, about 3.4% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
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 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID. Tap any home to ask about it.
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.
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.
Housing distress & ownership in WINDSOR AT WESTSIDE; WINDSOR/WESTSIDE, KISSIMMEE
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period September 2026 through September 2026. Deemed reliable but not guaranteed.
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, tiles © CARTO.
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.
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.
HOA, CDD & Fees
- HOA dues reported around $584/month (about $7,008/yr) · median of 6 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $584 per month ($7,008 a year) - the median AssociationFee across 6 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
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 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 →
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 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. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how WINDSOR AT WESTSIDE; WINDSOR/WESTSIDE fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Windsor at Westside; Windsor/Westside
Where is Windsor at Westside; Windsor/Westside?
Windsor at Westside; Windsor/Westside is a community in KISSIMMEE, Osceola County, Florida.
Are there homes for sale in Windsor at Westside; Windsor/Westside right now?
Yes - 3 active and 0 pending listings as of the last feed refresh (twice daily). They are listed on this page.
Does Windsor at Westside; Windsor/Westside have an HOA or CDD?
No HOA is on record for Windsor at Westside; Windsor/Westside in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
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