Windsor at Westside
Homes for Sale in Kissimmee, FL
All 3,127 homes for sale in Kissimmee, FL · median $375,000 · 960 homes for sale in 34747 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 2026, Windsor At Westside in Kissimmee, FL has 60 homes for sale and 8 pending, asking from $380,000 to $720,000 (median $483,500). Over the 12 months ending 2026-11-13, 28 recorded sales closed at a median of $517,500, $164 per square foot, a median 83 days on market, sellers accepting 92% of original asking. Homes listed or recently sold were built 2015 - 2020; 78 of 80 report an HOA (median $584/mo); none of the 80 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 $7,880 ($7,280 with the full homestead exemption).
Last 30 days in Windsor at Westside: 15 new listings (median asking $437,500), 8 under contract right now, 8 closed sales (median $520,000). As of November 14, 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 · 133 daysTop listing
Active · 104 days
Active · 23 days
Active · 154 days
Active · 120 days
Active · 193 days
Active · 92 days
Active · 6 days
Active · 4 days
Active · 4 days
Active · 79 days
Active · 66 days
Active · 79 days
Active · 182 daysActive and pending Windsor at Westside listings as of 2026-11-12, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Tap any home to ask about it.
Price here is driven by size and finish more than location. These are large homes - a median of roughly 3,400 square feet built between 2015 and 2020 - and they trade at about $172 a foot. The median sits at $495,000, but condition and furnishing packages scatter the spread widely, so two comparable floor plans can close well apart depending on how they're outfitted.
The market posture is clearly buyer-leaning. With 10.6 months of supply, 76 active listings, and a median 84 days on market, there is no pressure to move fast. Prices are off 13.9% year over year, which means sellers should expect negotiation and realistic pricing, and buyers have room to be selective. The near-zero homestead share tells you this is an investment- and short-term-rental-oriented community, not an owner-occupied one - that shapes both supply and how aggressively listings are priced.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Windsor at Westside right now
🟢 Buyer-leaning market. 9.6 months of supply and 11% 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 November 13, 2026. Confidence: Very High (85 active and pending listings, 28 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated November 14, 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 November 13, 2026): the median sale price is about $518K ($164 per sq ft over the trailing 12 months of closed sales), a median 83 days on market for closed sales, and 9.6 months of supply, a buyer-leaning market.
In ZIP 34747 (Kissimmee), 1,203 homes closed in the last 12 months at a median of $470K ($220/sq ft), down 3.0% year over year, with a median 75 days on market. Right now 447 active and 67 pending listings. See the live ZIP 34747 housing market and the Osceola County market.
County records show 94 qualified sales in Windsor At Westside across 2024 - 2025 (69 in 2024, 25 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 65 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 706 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).
Windsor At Westside is a gated, guard-staffed resort-style community in Kissimmee built out over 2015 - 2020, where the homes run large and the ownership base skews toward rental and investment use rather than primary residence.
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.
Who Windsor at Westside is best for.
Best for
- Buying to operate a short-term rental backed by resort-style amenities
- Buyers who want negotiating leverage in a market with 10.6 months of supply
- Looking for large, recently built square footage at or near the median price
Probably not for
- Seeking a primarily owner-occupied community for a full-time residence
- Needing to buy or sell quickly in a market where the median listing takes 84 days
- Wanting to avoid HOA deed restrictions and a rental-oriented operating model
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending November 13 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($518K) IS the median in the snapshot above.
Windows contain 0 to 28 sales each (28 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2021 through 2026. Deemed reliable but not guaranteed.
12% 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 (2026-11-14).
WINDSOR AT WESTSIDE Market Scorecard
WINDSOR AT WESTSIDE is currently a strong buyer's market. About 60.0 months of supply, a median asking price of $483,500, and homes go under contract in about 106 days.
Typical home value in the 34747 ZIP is $399,304, about 8.0% above 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 November 2026.
- October 2026Parks & Amenities
145,000 sq ft All Sports Dome planned on Gus Road in Kissimmee
All Sports Dome Southeast plans a climate-controlled indoor inflatable dome at 3070 Gus Road with multi-sport courts, turf fields and training areas. It would be the brand's first Greater Orlando location, with an opening expected in 2027 and no exact date given.
What it may mean for the marketAn indoor sports venue would add year-round recreation and event space on Kissimmee's Gus Road area. The project is about 15 miles southeast of Windsor At Westside, elsewhere in Osceola County.
Source: What Now Orlando - October 2026Infrastructure
Turnpike widening in Osceola County runs ahead of schedule at Fortune Road Bridge
Steel beams for the new westbound Fortune Road Bridge are in place a month early as Florida's Turnpike is widened from two to four lanes each way between Partin Settlement Road and Osceola Parkway. Westbound bridge traffic is expected at the start of 2027, and the broader project targets 2031. The bridge adds bike lanes and sidewalks.
What it may mean for the marketDoubling Turnpike capacity through this stretch should ease regional commutes between Kissimmee and the Orlando area once complete. The project is about 15 miles southeast of Windsor At Westside, elsewhere in Osceola County.
Source: WFTV - October 2026Development
Experience Kissimmee launches Film Kissimmee commission to recruit productions
The new film commission markets Osceola County to production companies through an online database of more than 100 filming locations and has hired a location manager. Leaders say productions could become a new economic driver, citing spending on hotels, vehicles, food and crew services.
What it may mean for the marketFilm work could add temporary jobs and visitor spending for hospitality and service businesses across Osceola County. The project is about 15 miles southeast of Windsor At Westside, elsewhere in Osceola County.
Source: WFTV - 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.
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 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
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 resort-rental community, priced as one
The amenity list reads like a resort: guard-gated entry, clubhouse, pool and spa, fitness center, tennis and basketball courts, a playground, park, and an on-site restaurant, all under deed restrictions. That infrastructure, combined with a homestead share near zero, signals a community organized around short-term stays and investor ownership. If you're buying to live here full-time, you're buying into an operating model built for turnover, and the HOA and deed restrictions deserve a close read before you commit.
For investors, the math is the point: large square footage, a full amenity package, and a buyer-leaning market with 10.6 months of supply mean you can negotiate and you shouldn't overpay. The current year-over-year decline of 13.9% underlines that this is a market where entry price matters more than momentum. Verify current amenity access, rental rules, and fees directly with the HOA - the amenities here are reported from MLS listings and can change.
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 3 factors (1.8). Basis: Liquidity & Demand 9.6 months of supply; Owner Commitment 1% owner-occupied; Pricing Power 92.5% sale-to-list. Refreshed with each data update.
Why work with Momentum here
A community like this rewards diligence over enthusiasm. We'll help you read the HOA documents and deed restrictions, pressure-test asking prices against an 84-day median and a 13.9% annual decline, and separate the furnished short-term-rental listings from true comparables. In a buyer-leaning market with double-digit months of supply, our job is to keep you from overpaying and to flag the operating costs that don't show up in the list price.
Windsor at Westside in 15 seconds.
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. 31 on record.
- 1638 Lima Avenue · off market
- 1682 Lima Avenue · off market
- 1844 Gobi Drive · off market
- 1864 Nice Court · off market
- 1869 Nice Court · off market
- 1953 Majorca Drive · off market
- 2058 Rome Drive · off market
- 2108 Morocco Way · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34747 |
|---|---|
| Homes in the community | 706 (FL DOR 2025 assessment roll) |
| Years built | 2015–2020 (median 2018) |
| Typical living area | 3,433 sq ft (median) |
| Home types (current listings and sales) | single-family 57%, townhouses 42% |
| Amenities listed by sellers | Clubhouse, Fitness Center, Pool, Playground, Gated Community - Guard, Tennis Court(s) |
| Sale prices, last 12 months | $517,500 median across 28 closed sales · $164 per sq ft |
| Days on market (closed sales) | 83 median |
| For sale right now | 76 active, 9 pending · median asking $483,500 · 9.6 months of supply |
| Owner-occupied (homestead) share | 1% |
Data as of November 13, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2021 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 November 13, 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 November 2026 through November 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.
- 2163 Tripoli Court $639,000 · 9 bd · 6 ba · 4,391 sq ft · listed Nov 10, 2026 Courtesy of ICON REALTY ASSOCIATES INC
- 2143 Tripoli Court $639,000 · 9 bd · 6 ba · 4,391 sq ft · listed Nov 10, 2026 Courtesy of ICON REALTY ASSOCIATES INC
- 1813 Nice Court $535,000 · 6 bd · 4.5 ba · 3,142 sq ft · listed Nov 9, 2026 Courtesy of KELLER WILLIAMS REALTY AT THE PARKS
- 8895 Qin Loop $649,000 · 8 bd · 6 ba · 4,041 sq ft · listed Nov 8, 2026 Courtesy of NORTH 2 SOUTH REALTY INTERNATIONAL INC
- 8935 Zurich Lane $488,000 · 5 bd · 4 ba · 2,492 sq ft · listed Nov 6, 2026 Courtesy of TOPSKY REALTY INC
- 8827 Geneve Court $424,900 · 5 bd · 4.5 ba · 2,263 sq ft · listed Nov 5, 2026 Courtesy of LA ROSA REALTY LLC
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Windsor At Westside Right Now (69)
All 69 active and pending Windsor At Westside listings with a detail page, newest first, refreshed twice a day from the MLS. Showing the newest 60 of 69; the carousel above and the map carry the rest.
- 2143 Tripoli Court · $639,000 · 9 bd / 6 ba · listed Nov 9, 2026 · listed by Icon Realty Associates Inc
- 2163 Tripoli Court · $639,000 · 9 bd / 6 ba · listed Nov 8, 2026 · listed by Icon Realty Associates Inc
- 1813 Nice Court · $535,000 · 6 bd / 4.5 ba · listed Nov 7, 2026 · listed by Keller Williams Realty At The Parks
- 8895 Qin Loop · $649,000 · 8 bd / 6 ba · listed Nov 7, 2026 · listed by North 2 South Realty International Inc
- 8935 Zurich Lane · $488,000 · 5 bd / 4 ba · listed Nov 5, 2026 · listed by Topsky Realty Inc
- 8827 Geneve Court · $424,900 · 5 bd / 4.5 ba · listed Nov 5, 2026 · listed by La Rosa Realty Llc
- 8812 Corcovado Drive · $435,000 · 5 bd / 4 ba · listed Nov 4, 2026 · listed by Florida Spirit Homes
- 8834 Geneve Court · $419,000 · 5 bd / 4.5 ba · listed Nov 1, 2026 · listed by Topsky Realty Inc
- 2415 Dubai Street · $415,000 · 5 bd / 4.5 ba · listed Oct 28, 2026 · listed by Jc Premium Realty Llc
- 2441 Dubai Street · $389,900 · 5 bd / 4.5 ba · pending · listed Oct 27, 2026 · listed by Top Florida Homes
- 2422 Dubai Street · $449,990 · 5 bd / 4.5 ba · listed Oct 26, 2026 · listed by Florida Realty Investments
- 1965 Majorca Drive · $437,500 · 5 bd / 4.5 ba · listed Oct 23, 2026 · listed by Concord International Realty
- 8882 Geneve Ct · $415,000 · 4 bd / 3.5 ba · listed Oct 23, 2026 · listed by Market Connect Realty Llc
- 8849 Corcovado Drive · $680,000 · 9 bd / 6 ba · pending · listed Oct 23, 2026 · listed by Unione Realty Inc
- 8817 Corcovado Drive · $678,000 · 9 bd / 6 ba · listed Oct 22, 2026 · listed by Global Sapphire Realty
- 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 · pending · listed Oct 9, 2026 · listed by Kressler Real Estate
- 2433 Dubai Street · $419,000 · 5 bd / 4.5 ba · listed Oct 8, 2026 · listed by Ratio Real Estate, Llc
- 2187 Tripoli Court · $580,000 · 8 bd / 6 ba · listed Oct 8, 2026 · listed by La Rosa Realty Llc
- 2191 Tripoli Court · $580,000 · 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 · $516,000 · 6 bd / 4.5 ba · listed Sep 30, 2026 · listed by Alliance Real Estate Group
- 2462 Dubai Street · $475,000 · 5 bd / 4 ba · listed Sep 11, 2026 · listed by Keller Williams Realty Smart 1
- 2105 Malta Terrace · $629,900 · 8 bd / 6 ba · listed Sep 11, 2026 · listed by Keller Williams Advantage 2 Realty
- 1885 Nice Court · $559,000 · 6 bd / 4.5 ba · listed Sep 11, 2026 · listed by Florida Resort Realty Llc
- 8924 Bengal Court · $639,900 · 9 bd / 6 ba · pending · listed Sep 11, 2026 · listed by Realtycity Inc
- 8891 Geneve Court · $390,000 · 5 bd / 4.5 ba · listed Sep 10, 2026 · listed by La Rosa Realty Llc
- 1599 Lima Avenue · $629,900 · 8 bd / 6 ba · listed Sep 10, 2026 · listed by La Rosa Realty Llc
- 1690 Lima Avenue · $639,000 · 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 · $469,990 · 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 · $464,000 · 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 · $544,990 · 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
- 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
- 2451 Luxor Drive · $720,000 · 8 bd / 6 ba · listed Sep 4, 2026 · listed by Orlando Regional Property Management
- 8930 Sydney Avenue · $389,000 · 5 bd / 4.5 ba · pending · listed Sep 4, 2026 · listed by Kressler Real Estate
- 2015 Majorca Drive · $380,000 · 5 bd / 4.5 ba · listed Sep 1, 2026 · listed by The Landrua Group Real Estate Inc
- 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 · pending · 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 15, 2026 · listed by Re/Max Titanium Group
- 2070 Rome Drive · $415,000 · 5 bd / 4.5 ba · listed Aug 15, 2026 · listed by Real Broker, Llc
- 1888 Gobi Drive · $499,900 · 6 bd / 4.5 ba · listed Aug 15, 2026 · listed by Multi Choice Realty Llc
- 1857 Nice Court · $459,000 · 5 bd / 4 ba · listed Aug 15, 2026 · listed by Ratio Real Estate, Llc
- 1908 Nice Court · $669,990 · 9 bd / 6 ba · listed Aug 15, 2026 · listed by Multi Choice Realty Llc
- 1974 Majorca Drive · $415,000 · 5 bd / 4.5 ba · listed Aug 15, 2026 · listed by Avanti Way Realty Llc
- 8936 Prague Way · $495,000 · 6 bd / 4.5 ba · listed Aug 15, 2026 · listed by Compass Florida Llc
- 1829 Gobi Drive · $570,000 · 8 bd / 6 ba · listed Aug 15, 2026 · listed by La Rosa Realty Llc
Recently sold in Windsor At Westside Kissimmee
- 8849 Corcovado Drive · sold $650,000
- 8816 Corcovado Drive · sold $385,000
- 8879 Qin Loop · sold $680,000
- 8931 Zurich Lane · sold $465,000
- 1638 Lima Avenue · sold $640,000
- 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
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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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 (67 listings, MLS, 2026-11-14). 100% of the 67 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 92 MLS listings (most billed monthly; 2026-11-14). 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 65 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 74 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. |
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Frequently Asked Questions
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Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: November 12, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending November 13, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (16 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-11-13 |
| Historical depth | Closed-sale records back to 2021 (30 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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