Windsor Westside Windsor at 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 Westside Windsor At Westside in Kissimmee, FL has 1 home for sale. As of September 2026, the MLS records 5 closed sales in Windsor Westside Windsor At Westside in Kissimmee, FL since 2024, the most recent in August 2025. Across Kissimmee as a whole, 2,431 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,223 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).
Part of the Westside Kissimmee master-planned community in Kissimmee, FL — see all Westside Kissimmee homes for sale (88 listings across 5 villages and sections in the MLS).
Windsor Westside Windsor at Westside right now
🟢 Buyer-leaning market. 12.0 months of supply and 0% of the inventory already under contract give buyers above-average negotiating leverage.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 12, 2026. Confidence: Low (1 active and pending listings, 0 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 14, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The market around Windsor Westside Windsor at Westside
Windsor Westside Windsor at Westside is too small for its own price trend, so here is the market around it.
In ZIP 34747, 1,258 homes are on the market and 12% are under contract — a slower corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
ZIP and county figures describe the wider market, not Windsor Westside Windsor at Westside specifically. Momentum Research analysis of MLS records.
Homes For Sale Right Now in Windsor Westside Windsor at Westside
Live MLS inventory for Windsor Westside Windsor at 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 Westside Windsor at Westside listings as of 2026-09-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2024 through 2025. Tap any home to ask about it.
Life at Windsor Westside Windsor at Westside
- Basketball Court · reported on 2 of 2 listings
- Clubhouse · reported on 2 of 2 listings
- Fitness Center · reported on 2 of 2 listings
- Gated · reported on 2 of 2 listings
- Maintenance · reported on 2 of 2 listings
- Playground · reported on 2 of 2 listings
- Pool · reported on 2 of 2 listings
- Tennis Court(s) · reported on 1 of 2 listings
- Gated Community - Guard · reported on 1 of 2 listings
- Cable TV · reported on 1 of 2 listings
- Park · reported on 1 of 2 listings
- Recreation Facilities · reported on 1 of 2 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.
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Westside K-8 · Elementary
- West Side · Middle
- Celebration High · High
Zoned schools reflect the assignments reported on recent Windsor Westside Windsor at Westside listings and can change; always confirm with Osceola County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any Windsor Westside Windsor at Westside address.
Shop the zone: Homes zoned for Celebration High High School
The Windsor Westside Windsor at Westside buying strategy.
If we were buying in Windsor Westside Windsor at 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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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 Westside Windsor at Westside.
A closer look at the Windsor Westside Windsor at Westside market
Inventory runs at 12.0 months of supply, a buyer-leaning market.
The location and the amenities are priced into every listing in Windsor Westside Windsor at 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 4 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 4 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 Westside Windsor at 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 Westside Windsor at 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 Westside Windsor at 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 Westside Windsor at Westside home worth?
Get a no-obligation home value based on real comparable sales in Windsor Westside Windsor at 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 →
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/WESTSIDE, WINDSOR AT WESTSIDE Market Scorecard
WINDSOR/WESTSIDE, WINDSOR AT WESTSIDE is currently a strong buyer's market. About 12.0 months of supply, a median asking price of $689,995, and homes go under contract in about 192 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.
Frequently Asked Questions
Is Windsor Westside Windsor at Westside a buyer's or seller's market right now?
Who is the best real estate agent for Windsor Westside Windsor at Westside?
How do I find a top Kissimmee real estate agent who knows Windsor Westside Windsor at Westside?
Can Momentum Realty connect me with an agent for Windsor Westside Windsor at Westside?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2024 (5 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 local comps.
Looking to buy here? Search homes for sale →
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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 Westside Windsor At Westside fits the bigger picture — live prices, inventory, and Momentum Scores:
Nearby Communities
Explore more neighborhoods near Windsor Westside Windsor at Westside with Momentum Realty’s local guides.