WINDSOR AT WESTSIDE
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
WINDSOR AT WESTSIDE right now
🟢 Buyer-leaning market. 10.8 months of supply and 8% 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 August 2, 2026. Confidence: Very High (80 active and pending listings, 73 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 18 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 August 2. Confidence: Very High (73 and 41 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 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 August 2, 2026): the median sale price is about $495K ($174 per sq ft over the trailing 12 months of closed sales), a median 84 days on market for closed sales, and 10.8 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 (73 closings in the current window).
WINDSOR AT WESTSIDE is a community of 880 homes in KISSIMMEE, Osceola County, built between 2015 and 2020 (median 2018), 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 WESTSIDEPrice History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending August 2 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 73 sales each (73 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.
WINDSOR AT WESTSIDE Market Scorecard
WINDSOR AT WESTSIDE is currently a strong buyer's market. About 10.6 months of supply, a median asking price of $527,000, and homes go under contract in about 57 days.
Go deeper: 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.
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 August 2026 through August 2026. Deemed reliable but not guaranteed.
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 · 110 days
Active · 6 days
Active · 1 days
Active · 15 days
Active · 121 days
Active · 3 days
Active · 80 days
Active · 32 days
Active · 1 days
Active · 115 days
Active · 59 days
Active · 8 days
Active · 138 daysActive and pending WINDSOR AT WESTSIDE listings as of 2026-08-23, 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 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.
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 $174 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 10.8 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 880 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 10.8 months of supply; Owner Commitment 1% owner-occupied; Pricing Power 93.3% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- Mandatory HOA. Confirm current dues
- 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.
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?
Do cash buyers compete in WINDSOR AT WESTSIDE?
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: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2015 (189 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 your area comps.
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