Windsor at Westside; Windsor/Westside
Homes for Sale in Kissimmee, FL
All 3,104 homes for sale in Kissimmee, FL · median $375,000 · 773 townhomes for sale in Kissimmee · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 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.
9% of homes for sale in ZIP 34747 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-10-25).
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: Stellar MLS, distributed by MLS GRID, 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 2026-09-26, 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.
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.
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.
What it really costs to own in Windsor at Westside; Windsor/WestsideHomes for Sale
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, 2026-10-24). 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; 2026-10-24). 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. |
Email me new listings in Windsor at Westside; Windsor/WestsideHomes for Sale
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/WestsideHomes for Sale
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windsor at Westside; Windsor/WestsideHomes for Sale will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $584/month (about $7,008/yr) · median of 3 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 3 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, 2026-10.
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 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. 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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More Kissimmee & Kissimmee, St. Cloud & Osceola County guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Kissimmee, St. Cloud & Osceola County or the full Neighborhood Finder.
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.
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.
Every Home for Sale in Windsor At Westside Windsor Westside Kissimmee Right Now (3)
All 3 active and pending Windsor At Westside Windsor Westside Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 8932 Sydney Avenue · $449,000 · 5 bd / 4.5 ba · listed Sep 10, 2026 · listed by Golden Sun Realty Inc
- 8942 Sydney Avenue · $445,000 · 5 bd / 4.5 ba · listed Aug 5, 2026 · listed by Golden Sun Realty Inc
- 8904 Sydney Avenue · $419,000 · 5 bd / 4.5 ba · listed by Golden Sun Realty Inc
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Kissimmee guides & data
- Market data
- Cost of living
- Best neighborhoods (ranked by data)
- Best neighborhoods
- Flood zones
- Property taxes (Osceola County)
- Homestead exemption (Osceola County)
- Home insurance cost
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Sydney Avenue (3 homes on record)
Nearby Communities
Explore more neighborhoods near Windsor at Westside; Windsor/Westside with Momentum Realty’s local guides.