Windsor At Westside
Homes for Sale in Kissimmee, FL
All 3,104 homes for sale in Kissimmee, FL · median $375,000 · 950 homes for sale in 34747 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, Windsor At Westside in Kissimmee, FL has 60 homes for sale and 5 pending, asking from $389,000 to $720,000 (median $497,450). Over the 12 months ending 2026-09-20, 87 recorded sales closed at a median of $495,000, $172 per square foot, a median 84 days on market, sellers accepting 93% of original asking (-14% versus the prior year). Homes listed or recently sold were built 2015 - 2020; 75 of 77 report an HOA (median $584/mo); none of the 77 geocoded homes sit in a FEMA special flood hazard zone (median elevation 117 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $7,540 ($6,940 with the full homestead exemption).
Last 30 days in Windsor At Westside: 12 new listings (median asking $428,250), 5 under contract right now, 5 closed sales (median $500,000). As of October 25, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
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 · 112 daysTop listing
Active · 242 days
Active · 83 days
Active · 321 days
Active · 2 days
Active · 133 days
Active · 99 days
Active · 246 days
Active · 172 days
Active · 71 days
Active · 223 days
Active · 58 days
Active · 58 days
Active · 58 daysActive and pending Windsor At Westside listings as of 2026-10-23, 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 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 October 24, 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).
In ZIP 34747 (Kissimmee), 2,599 homes closed in the last 12 months at a median of $460K ($220/sq ft), down 3.8% year over year, with a median 75 days on market. Right now 581 active and 101 pending listings put supply at about 7.3 months - a buyer's market. See the live ZIP 34747 housing market and the Osceola County market.
County records show 92 qualified sales in Windsor At Westside across 2024 - 2025 (68 in 2024, 24 in 2025), median $580,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Windsor At Westside: of 64 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Kissimmee.
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.
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.
8% of homes for sale in Windsor At Westside 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 Market Scorecard
WINDSOR AT WESTSIDE is currently a strong buyer's market. About 57.0 months of supply, a median asking price of $495,000, and homes go under contract in about 98 days.
Typical home value in the 34747 ZIP is $399,304, about 3.0% 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.
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 contributors.
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.
Shop the zone: Homes zoned for Celebration High High School
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.
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 all homes for sale in Kissimmee →
Recently off market in Windsor At Westside
Homes in Windsor At Westside that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 26 on record.
- 1864 Nice Court · off market
- 1869 Nice Court · off market
- 1940 Nice Court · off market
- 1953 Majorca Drive · off market
- 2058 Rome Drive · off market
- 2108 Morocco Way · off market
- 2112 Morocco Way · off market
- 2135 Tripoli Court · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34747 |
|---|---|
| Homes in the community | 719 (FL DOR 2025 assessment roll) |
| Years built | 2015–2020 (median 2018.0) |
| Typical living area | 3,433 sq ft (median) |
| Home types (current listings and sales) | single-family 62%, townhouses 38% |
| Amenities listed by sellers | Pool, Clubhouse, Fitness Center, Playground, Gated Community - Guard, Tennis Court(s) |
| Sale prices, last 12 months | $495,000 median across 87 closed sales · $172 per sq ft · -13.9% vs the prior 12 months |
| Days on market (closed sales) | 84 median |
| For sale right now | 76 active, 8 pending · median asking $521,950 · 10.6 months of supply |
| Owner-occupied (homestead) share | 1% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2015 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Windsor At Westside key facts,” movewithmomentum.com/neighborhoods/windsor-at-westside-kissimmee, data as of September 20, 2026.
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.
Just listed in Windsor At Westside
The newest homes for sale in Windsor At Westside right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 8849 Corcovado Drive $680,000 · 9 bd · 6 ba · 4,391 sq ft · listed Oct 23, 2026 Courtesy of UNIONE REALTY INC
- 1965 Majorca Drive $437,500 · 5 bd · 4.5 ba · 2,263 sq ft · listed Oct 23, 2026 Courtesy of CONCORD INTERNATIONAL REALTY
- 8817 Corcovado Drive $678,000 · 9 bd · 6 ba · 4,391 sq ft · listed Oct 20, 2026 Courtesy of GLOBAL SAPPHIRE REALTY
- 8930 Sydney Avenue $389,000 · 5 bd · 4.5 ba · 2,265 sq ft · listed Oct 16, 2026 Courtesy of KRESSLER REAL ESTATE
- 8843 Geneve Ct $409,990 · 5 bd · 4.5 ba · 2,263 sq ft · listed Oct 15, 2026 Courtesy of FLORIDA CONNEXION PROPERTIES
- 8887 Geneve Court $399,000 · 5 bd · 4.5 ba · 2,265 sq ft · listed Oct 8, 2026 Courtesy of KRESSLER REAL ESTATE
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Windsor At Westside Kissimmee Right Now (64)
All 64 active and pending Windsor At Westside Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS. Showing the newest 60 of 64; the carousel above and the map carry the rest.
- 8882 Geneve Ct · $415,000 · 4 bd / 3.5 ba · listed by Market Connect Realty Llc
- 8843 Geneve Ct · $409,990 · 5 bd / 4.5 ba · listed Oct 15, 2026 · listed by Florida Connexion Properties
- 8887 Geneve Court · $399,000 · 5 bd / 4.5 ba · listed Oct 9, 2026 · listed by Kressler Real Estate
- 2187 Tripoli Court · $570,000 · 8 bd / 6 ba · listed Oct 8, 2026 · listed by La Rosa Realty Llc
- 2433 Dubai Street · $419,000 · 5 bd / 4.5 ba · listed Oct 8, 2026 · listed by Ratio Real Estate, Llc
- 2191 Tripoli Court · $570,000 · 8 bd / 6 ba · listed Oct 6, 2026 · listed by La Rosa Realty Llc
- 2404 Tangier Drive · $416,000 · 5 bd / 4.5 ba · listed Oct 2, 2026 · listed by Lpt Realty, Llc
- 1732 Lima Avenue · $525,000 · 6 bd / 4.5 ba · listed Sep 30, 2026 · listed by Alliance Real Estate Group
- 8879 Qin Loop · $699,000 · 8 bd / 6 ba · pending · listed Sep 19, 2026 · listed by La Rosa Realty Llc
- 1638 Lima Avenue · $650,000 · 9 bd / 6 ba · pending · listed Sep 15, 2026 · listed by Exp Realty Llc
- 2462 Dubai Street · $475,000 · 5 bd / 4 ba · listed Sep 11, 2026 · listed by Keller Williams Realty Smart 1
- 8924 Bengal Court · $639,900 · 9 bd / 6 ba · listed Sep 11, 2026 · listed by Realtycity Inc
- 1885 Nice Court · $559,000 · 6 bd / 4.5 ba · listed Sep 11, 2026 · listed by Florida Resort Realty Llc
- 2105 Malta Terrace · $629,900 · 8 bd / 6 ba · listed Sep 11, 2026 · listed by Keller Williams Advantage 2 Realty
- 8891 Geneve Court · $390,000 · 5 bd / 4.5 ba · listed Sep 10, 2026 · listed by La Rosa Realty Llc
- 1599 Lima Avenue · $649,900 · 8 bd / 6 ba · listed Sep 10, 2026 · listed by La Rosa Realty Llc
- 1690 Lima Avenue · $644,900 · 8 bd / 6 ba · listed Sep 10, 2026 · listed by La Rosa Realty Llc
- 8907 Sydney Avenue · $430,000 · 5 bd / 4.5 ba · listed Sep 10, 2026 · listed by C23 Realty Llc
- 2417 Dubai Street · $495,000 · 5 bd / 4.5 ba · listed Sep 10, 2026 · listed by Realty One Group Inspiration
- 8923 Sydney Avenue · $465,000 · 5 bd / 4.5 ba · listed Sep 10, 2026 · listed by Wra Business & Real Estate
- 8875 Geneve Ct · $420,000 · 5 bd / 4.5 ba · listed Sep 10, 2026 · listed by Newkey Real Estate Llc
- 2426 Tangier Drive · $495,000 · 5 bd / 4.5 ba · listed Sep 10, 2026 · listed by Exp Realty Llc
- 8825 Rhodes Street · $675,000 · 8 bd / 6 ba · listed Sep 10, 2026 · listed by Keller Williams Realty At The Lakes
- 1809 Nice Court · $490,000 · 6 bd / 4.5 ba · listed Sep 10, 2026 · listed by La Rosa Realty Llc
- 8877 Bengal Court · $565,000 · 5 bd / 5.5 ba · listed Sep 10, 2026 · listed by Celebrity Global Realty Llc
- 2440 Tangier Drive · $525,000 · 5 bd / 4 ba · listed Sep 8, 2026 · listed by Exp Realty Llc
- 8812 Macapa Drive · $680,000 · 8 bd / 6 ba · listed Sep 7, 2026 · listed by Intop Realty Llc
- 1917 Nice Court · $549,990 · 5 bd / 4 ba · listed Sep 6, 2026 · listed by Empire Network Realty
- 1744 Lima Avenue · $589,000 · 7 bd / 5.5 ba · listed Sep 6, 2026 · listed by Cornerstone International Property Group Llc
- 8816 Corcovado Drive · $408,000 · 5 bd / 5.5 ba · pending · listed Sep 6, 2026 · listed by Us Reliance Solutions Inc
- 1987 Majorca Drive · $416,999 · 4 bd / 3.5 ba · listed Sep 5, 2026 · listed by Nobska Real Estate Llc
- 8831 Geneve Court · $409,000 · 5 bd / 4.5 ba · pending · listed Sep 5, 2026 · listed by V Enterprises Llc
- 8930 Sydney Avenue · $389,000 · 5 bd / 4.5 ba · listed Sep 4, 2026 · listed by Kressler Real Estate
- 2451 Luxor Drive · $720,000 · 8 bd / 6 ba · listed Sep 4, 2026 · listed by Orlando Regional Property Management
- 2015 Majorca Drive · $412,900 · 5 bd / 4.5 ba · listed Sep 1, 2026 · listed by Realty One Group Inspiration
- 8838 Geneve Court · $435,000 · 5 bd / 4.5 ba · listed Aug 29, 2026 · listed by Orlando Regional Property Management
- 8867 Geneve Court · $404,000 · 4 bd / 3.5 ba · listed Aug 29, 2026 · listed by Providence Realty And Property Management Llc
- 8866 Geneve Court · $469,000 · 5 bd / 4.5 ba · listed Aug 26, 2026 · listed by La Rosa Realty Llc
- 8904 Prague Way · $515,000 · 5 bd / 4 ba · listed Aug 25, 2026 · listed by La Rosa Realty Llc
- 9025 Rhodes Street · $390,000 · 5 bd / 4.5 ba · listed Aug 22, 2026 · listed by Lifestyle International Realty
- 8899 Geneve Ct · $394,900 · 4 bd / 3.5 ba · listed Aug 17, 2026 · listed by Hopkey Realty
- 1610 Lima Avenue · $655,000 · 8 bd / 6 ba · listed Aug 14, 2026 · listed by Re/Max Titanium Group
- 2022 Majorca Drive · $399,990 · 4 bd / 3.5 ba · listed Aug 14, 2026 · listed by Wra Business & Real Estate
- 2070 Rome Drive · $424,900 · 5 bd / 4.5 ba · listed Aug 10, 2026 · listed by Real Broker, Llc
- 8817 Corcovado Drive · $678,000 · 9 bd / 6 ba · listed Aug 9, 2026 · listed by Global Sapphire Realty
- 1857 Nice Court · $459,000 · 5 bd / 4 ba · listed Aug 7, 2026 · listed by Ratio Real Estate, Llc
- 1682 Lima Avenue · $679,000 · 8 bd / 6 ba · listed Jul 26, 2026 · listed by Ratio Real Estate, Llc
- 1888 Gobi Drive · $499,900 · 6 bd / 4.5 ba · listed Jul 25, 2026 · listed by Multi Choice Realty Llc
- 1974 Majorca Drive · $440,000 · 5 bd / 4.5 ba · listed Jul 25, 2026 · listed by Avanti Way Realty Llc
- 1908 Nice Court · $669,990 · 9 bd / 6 ba · listed by Multi Choice Realty Llc
- 8936 Prague Way · $495,000 · 6 bd / 4.5 ba · listed by Compass Florida Llc
- 1829 Gobi Drive · $570,000 · 8 bd / 6 ba · listed by La Rosa Realty Llc
- 1909 Majorca Drive · $424,999 · 5 bd / 4.5 ba · listed by Team Donovan
- 8956 Zurich Lane · $575,000 · 7 bd / 5.5 ba · listed by Epique Realty, Inc.
- 2147 Tripoli Court · $658,000 · 9 bd / 6 ba · listed by Empire Network Realty
- 2410 Tangier Drive · $399,900 · 5 bd / 4.5 ba · listed by Florida Morning Realty Llc
- 8933 Prague Way · $479,000 · 5 bd / 4 ba · listed by Wra Business & Real Estate
- 8931 Zurich Lane · $483,000 · 5 bd / 4 ba · pending · listed by Topsky Realty Inc
- 1844 Gobi Drive · $655,000 · 6 bd / 4.5 ba · listed by Real Broker, Llc
- 9013 Rhodes Street · $550,000 · 6 bd / 4.5 ba · listed by Wra Business & Real Estate
Recently sold in Windsor At Westside Kissimmee
- 8859 Geneve Court · sold $370,000
- 2413 Dubai St · sold $410,000
- 8801 Rhodes Street · sold $575,000
- 8811 Macapa Drive · sold $685,000
- 2438 Tangier Drive · sold $500,000
- 2108 Morocco Way · sold $555,000
- 8922 Zurich Lane · sold $480,000
- 8900 Sydney Avenue · sold $405,000
- 2135 Tripoli Court · sold $630,000
- 8901 Rhodes Street · sold $520,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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Kissimmee guides & data
- Market data
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- Best neighborhoods (ranked by data)
- Best neighborhoods
- Flood zones
- Property taxes (Osceola County)
- Homestead exemption (Osceola County)
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Florida buyer guides
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- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
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What it really costs to own in Windsor At Westside
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 $1,922/yr in CDD or special-district assessments on the tax bill (65 listings, MLS, 2026-10-24). 98% of the 66 listings that report the field show one. The amount is per lot and set by the district: confirm it on the parcel's TRIM notice. |
|---|---|
| HOA dues | Median $584/month across 79 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. Flood: of 64 listing addresses checked against the FEMA flood map, 100% sit outside the high-risk zone. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 2018 across 75 listings. An original roof here is about 8 years old: still inside the 15-year window Florida carriers use, but ask for the roof's permit date before you bind coverage. |
Email me new listings in Windsor At Westside
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
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windsor At Westside will answer, and the answer is published on this page for the next buyer.
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?
Where is Windsor At Westside, and what county is it in?
Is Windsor At Westside in a flood zone?
Is Windsor At Westside a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 23, 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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