Windsor At Westside
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Homes For Sale Right Now in Windsor At Westside
Live MLS inventory for 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 · 1 daysTop listing
Active · 6 days
Active · 1 days
Active · 0 days
Active · 193 days
Active · 3 days
Active · 80 days
Active · 32 days
Active · 1 days
Active · 52 days
Active · 115 days
Active · 157 days
Active · 43 days
Active · 42 daysActive and pending Windsor At Westside listings as of 2026-10-09, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026. Tap any home to ask about it.
Windsor At Westside right now
🟢 Buyer-leaning market. 10.6 months of supply and 10% 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 20, 2026. Confidence: Very High (84 active and pending listings, 87 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($495K) is down 13.9% from the prior 12 months ($575K). With about 20 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Very High (87 and 36 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 20, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Windsor At Westside market snapshot (as of September 20, 2026): the median sale price is about $495K ($172 per sq ft over the trailing 12 months of closed sales), a median 84 days on market for closed sales, and 10.6 months of supply, a buyer-leaning market. The trailing-12-month median is down 14% from the prior 12 months, computed from record-level Stellar MLS closed sales (87 closings in the current window).
Windsor At Westside is a community of 719 homes in Kissimmee, Osceola County, built between 2015 and 2020 (median 2018.0), with a median living area of about 3,433 square feet. 1% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Windsor At Westside. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Windsor At WestsidePhotos from Stellar MLS listings in Windsor At Westside; content deemed reliable but not guaranteed.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($495K) IS the median in the snapshot above, and the move from 2025 ($575K) IS the -13.9% one-year change.
Windows contain 0 to 87 sales each (87 in the current window); every figure carries its sample size. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026. Deemed reliable but not guaranteed.
12% 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 (2026-09-20).
Windsor At Westside Market Scorecard
Windsor At Westside is currently a buyer-leaning market. About 10.6 months of supply, a median asking price of $521,950, and homes go under contract in about 34 days.
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Windsor At 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 October 2026 through October 2026. Deemed reliable but not guaranteed.
Windsor At 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
- Fitness Center · reported on 54 of 64 listings
- Clubhouse · reported on 53 of 64 listings
- Pool · reported on 53 of 64 listings
- Playground · reported on 48 of 64 listings
- Gated Community - Guard · reported on 46 of 64 listings
- Tennis Court(s) · reported on 31 of 64 listings
- Restaurant · reported on 24 of 64 listings
- Gated · reported on 22 of 64 listings
- Park · reported on 15 of 64 listings
- Deed Restrictions · reported on 15 of 64 listings
- Basketball Court · reported on 12 of 64 listings
- Cable TV · reported on 11 of 64 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 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 At Westside address.
Recent Developments in Windsor At Westside
Development, infrastructure, retail, and school activity affecting Windsor At Westside, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection. The developer projects thousands of jobs at full build-out.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The site is about 7 miles southeast of Windsor At Westside.
Source: Spectrum News 13 - September 2026Infrastructure
CFX holds public meetings on 14-mile toll road through part of Split Oak Forest
The Central Florida Expressway Authority held public meetings on Sept. 16 and 17 for a 14-mile road from State Road 417 near Boggy Creek Road in Orange County to Nova Road in Osceola County. CFX says portions could begin construction next year and that the road would ease traffic on Narcoossee Road. The agency faces a legal challenge from Orange County and is pursuing an eminent domain case.
What it may mean for the marketIf built, the road would add a new east-west route between Lake Nona and St. Cloud, changing commute options and access to east Orange and Osceola land. The project is about 23 miles east of Windsor At Westside, elsewhere in Osceola County.
Source: Spectrum News 13 - September 2026Development
Lake County approves 2,241-acre Panther Run rezoning for up to 2,624 homes near Clermont
The Lake County Commission voted 3-1 on Sept. 1 to rezone about 2,241 acres in the Wellness Way area, north of Sawgrass Bay Boulevard, for GT Homes. The planned unit development allows up to 2,624 residential units and more than 1 million square feet of non-residential space, with sites reserved for a future public high school and public safety facilities. Plans include extending County Road 455 and about 11 miles of public trails.
What it may mean for the marketThe plan adds long-term housing supply, employment space and new connector roads in south Lake County, with infrastructure planned ahead of residential growth. The site is about 8 miles west of Windsor At Westside.
Source: Clermont Sun - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 5 miles southeast of Windsor At Westside.
Source: FOX 35 Orlando - August 2026Civic
St. Cloud council approves $6.7 million downtown apartment and parking garage agreement
The City Council unanimously approved an agreement with Atlantic Housing Partners for apartments and a parking garage next to City Hall. The Community Redevelopment Agency contributes $6.25 million and the city $460,000. The garage would hold 450 to 500 spaces, with 250 reserved for apartment residents.
What it may mean for the marketNew downtown rental housing and public parking would add residents and parking capacity to the St. Cloud core. The project is about 22 miles southeast of Windsor At Westside, elsewhere in Osceola County.
Source: Spectrum News 13
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in the Orlando Metro.
The Windsor At Westside buying strategy.
If we were buying in 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 At Westside.
A closer look at the Windsor At Westside market
At a median of $172 per square foot, Windsor At Westside prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 10.6 months of supply, a buyer-leaning market and the trailing-12-month median down 14% year over year. Homes that do trade take a median 84 days on market, useful leverage on any listing that has lingered.
The housing stock is 719 homes built between 2015 and 2020, and 1% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Windsor At Westside. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Windsor At Westside buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (2.0). Basis: Recent Direction -13.9% year-over-year; Liquidity & Demand 10.6 months of supply; Owner Commitment 1% owner-occupied; Pricing Power 93.0% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Flood & Insurance Context
Of 67 sampled listing addresses in this community: 100% outside the FEMA Special Flood Hazard Area (Zone X/B/C).
Address-sampled; individual parcels vary - verify any specific address at msc.fema.gov. Check any address at FEMA's Flood Map Service Center, and see average home-insurance costs by Florida county.
Source: FEMA National Flood Hazard Layer, address-level lookups (n=67) · as of 2026-10
Tools for a 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 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 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 At Westside home worth?
Get a no-obligation home value based on real comparable sales in 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 homes for sale in Windsor At Westside on the map →
Frequently Asked Questions
What is the median home price in Windsor At Westside?
How long do homes in Windsor At Westside take to sell?
Is Windsor At Westside a buyer's or seller's market right now?
How many homes are in Windsor At Westside?
What share of Windsor At Westside is owner-occupied?
When were the homes in Windsor At Westside built?
Who is the best real estate agent for Windsor At Westside?
How do I find a top Kissimmee real estate agent who knows Windsor At Westside?
Can Momentum Realty connect me with an agent for Windsor At Westside?
Nearby Communities
Explore more neighborhoods near Windsor At Westside with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 9, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (17 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2015 (205 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.
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See how Windsor At Westside fits the bigger picture — live prices, inventory, and Momentum Scores: