Windsor Point
Homes for Sale in Kissimmee, FL
All 3,084 homes for sale in Kissimmee, FL · median $375,000 · 254 homes for sale in 34741 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of October 2026, Windsor Point in Kissimmee, FL has 4 homes for sale. Over the 12 months ending 2026-08-02, 3 recorded sales closed at a median of $430,000, $212 per square foot, a median 123 days on market, sellers accepting 96% of original asking (+8% versus the prior year). Homes listed or recently sold were built 2003 - 2004; 8 of 8 report an HOA (median $76/mo); none of the 8 geocoded homes sit in a FEMA special flood hazard zone (median elevation 87 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $6,550 ($5,950 with the full homestead exemption).
Homes For Sale Right Now in Windsor Point
Live MLS inventory for Windsor Point. 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 · 53 daysTop listing
Active · 97 days
Active · 181 days
Pending · 36 daysActive and pending Windsor Point listings as of 2026-10-17, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2007 through 2026. Tap any home to ask about it.
Windsor Point is a tight, single-phase community built out between 2003 and 2005, with a median build year of 2004 and a consistent living area around 2,206 square feet. With only 67 homes total and 4 active listings, this is a market where inventory moves in small batches rather than a steady flow, and each listing carries more weight in setting the tone for the rest.
At 12 months of supply, the current posture leans toward buyers, meaning there is room to negotiate on terms and timing rather than compete on multiple offers. Sellers here should expect a more patient process and price realistically for condition and lot, since a thin active count means fewer comparable data points to lean on.
Windsor Point right now
🟢 Buyer-leaning market. 12.0 months of supply and 20% 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: Medium (5 active and pending listings, 3 closed sales in 12 months).
🟡 Still climbing. The trailing-12-month median ($430K) is up 7.5% from the prior 12 months ($400K). With about 2 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: Low (3 and 3 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 18, 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 Point market snapshot (as of August 2, 2026): the median sale price is about $430K ($212 per sq ft over the trailing 12 months of closed sales), a median 123 days on market for closed sales, and 12.0 months of supply, a buyer-leaning market. The trailing-12-month median is up 8% from the prior 12 months, computed from record-level Stellar MLS closed sales (3 closings in the current window).
In ZIP 34741 (Kissimmee), 754 homes closed in the last 12 months at a median of $411K ($205/sq ft), down 0.8% year over year, with a median 44 days on market. Right now 207 active and 46 pending listings put supply at about 6.1 months - a balanced market. See the live ZIP 34741 housing market and the Osceola County market.
Flood zones in Windsor Point: of 8 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 Point is a community of 67 homes in Kissimmee, Osceola County, built between 2003 and 2005 (median 2004), with a median living area of about 2,206 square feet. 70% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
A small, gated enclave in Kissimmee built out in the early 2000s, Windsor Point offers a consistent home size and age profile with a high share of owner-occupied homes, giving the community a settled, low-turnover character.
The setting & the homes.
Aerial and on-site photos of Windsor Point. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Windsor PointPhotos from Stellar MLS listings in Windsor Point; content deemed reliable but not guaranteed.
Who Windsor Point is best for.
Best for
- Buyers seeking a compact, gated community with amenities like a pool, clubhouse, and fitness center rather than an expansive resort-style development.
- Buyers comfortable navigating a market with limited active inventory and willing to move when the right listing appears.
- Buyers who value a consistent home age and size profile for easier apples-to-apples comparisons.
Probably not for
- Buyers who want to compare a large number of active listings before deciding.
- Buyers looking for new construction, since all homes here date to the 2003-2005 build period.
- Buyers seeking varied lot sizes or architectural styles across a bigger master-planned footprint.
Price 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 ($430K) IS the median in the snapshot above, and the move from 2025 ($400K) IS the +7.5% one-year change.
Windows contain 0 to 10 sales each (3 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 2007 through 2026. Deemed reliable but not guaranteed.
11% of homes for sale in ZIP 34741 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 (2026-10-18).
Windsor Point Market Scorecard
Windsor Point is currently a buyer-leaning market. About 12.0 months of supply, a median asking price of $424,500, and homes go under contract in about 97 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.
Windsor Point 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 Point
- Playground · reported on 6 of 6 listings
- Pool · reported on 6 of 6 listings
- Gated · reported on 4 of 6 listings
- Gated Community - No Guard · reported on 4 of 6 listings
- Park · reported on 3 of 6 listings
- Deed Restrictions · reported on 2 of 6 listings
- Community Mailbox · reported on 2 of 6 listings
- Clubhouse · reported on 1 of 6 listings
- Fitness Center · reported on 1 of 6 listings
- Security · reported on 1 of 6 listings
- Gated Community · reported on 1 of 6 listings
- Key Card Entry · reported on 1 of 6 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
- Floral Ridge Elementary · Elementary
- Kissimmee Middle · Middle
- Osceola County School for Arts · High
Zoned schools reflect the assignments reported on recent Windsor Point 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 Point address.
Shop the zone: Homes zoned for Osceola County School For Arts
Recent Developments in Windsor Point
Development, infrastructure, retail, and school activity affecting Windsor Point, 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 2 miles southwest of Windsor Point.
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 15 miles east of Windsor Point, elsewhere in Osceola County.
Source: Spectrum News 13 - 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 4 miles west of Windsor Point.
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 15 miles southeast of Windsor Point, elsewhere in Osceola County.
Source: Spectrum News 13 - March 2026Development
Orlando approves the 380-acre Dowden Central Community Development District in Lake Nona
Orlando approved the Dowden Central Community Development District, a roughly 380-acre district in the Lake Nona area of southeast Orlando, in March 2026. The district provides the framework to build roads, drainage, utilities, and parks for future development phases.
What it may mean for the marketA new community development district lays the groundwork for large-scale growth in the Lake Nona area, a step that typically precedes new housing and commercial activity nearby. The site is about 11 miles east of Windsor Point.
Source: ClickOrlando
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 Point buying strategy.
If we were buying in Windsor Point 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 Point.
A small footprint, a steady profile
With just 67 homes and construction concentrated in a narrow 2003-2005 window, Windsor Point does not offer the variety of a larger master-planned community. What it does offer is consistency: most homes share a similar era, layout scale near 2,206 square feet, and build quality, which simplifies comparisons for buyers evaluating condition versus price.
The homestead share of just over 70% points to a community where most owners occupy their homes rather than lease them, which tends to support more consistent upkeep of individual lots and common areas over time. Amenities reported across MLS listings include a pool, clubhouse, fitness center, playground, and gated access with key card entry, positioned within a deed-restricted, HOA-governed setting. Buyers should confirm current amenity access and any rules directly with the HOA, since MLS-reported features can lag real-world status.
The location and the amenities are priced into every listing in Windsor Point. 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 Point 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 (5.5). Basis: Recent Direction +7.5% year-over-year; Liquidity & Demand 12.0 months of supply; Owner Commitment 70% owner-occupied; Pricing Power 95.6% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a community with only 4 active listings, timing and access matter more than usual. We track Windsor Point's limited inventory closely so buyers see new listings early and sellers understand exactly how their home compares to the handful of others on the market at any given moment.
Windsor Point in 15 seconds.
What it really costs to own in Windsor Point
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $80/month across 244 MLS listings (most billed quarterly; 2026-10-15). 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 8 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 2004 across 7 listings. An original roof here would be about 22 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Windsor Point
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 Point
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windsor Point will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $80/month (about $960/yr) · median of 244 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $80 per month ($960 a year) - the median AssociationFee across 244 MLS records, normalised to a monthly figure; most are billed quarterly. 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, 2026-10.
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 8 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=8) · as of 2026-10
Tools for a Windsor Point 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 Point sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor Point, 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 Point home worth?
Get a no-obligation home value based on real comparable sales in Windsor Point, 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 POINT
Homes in WINDSOR POINT 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. 1 on record.
- 2975 White Cedar Circle · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34741 |
|---|---|
| Homes in the community | 67 (FL DOR 2025 assessment roll) |
| Years built | 2003–2005 (median 2004) |
| Typical living area | 2,206 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Pool, Playground, Gated, Gated Community - No Guard, Community Mailbox, Deed Restrictions |
| Sale prices, last 12 months | $430,000 median across 3 closed sales · $212 per sq ft · +7.5% vs the prior 12 months |
| Days on market (closed sales) | 123 median |
| For sale right now | 4 active, 1 pending · median asking $424,500 · 12.0 months of supply |
| Owner-occupied (homestead) share | 70% |
Data as of August 2, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2007 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Windsor Point key facts,” movewithmomentum.com/neighborhoods/windsor-point-kissimmee, data as of August 2, 2026.
Housing distress & ownership in WINDSOR POINT, 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 Point
The newest homes for sale in Windsor Point right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 2922 Willow Creek Lane $450,000 · 3 bd · 2 ba · 1,796 sq ft · 53 days on market Courtesy of WRA BUSINESS & REAL ESTATE
- 2930 White Cedar Circle $415,000 · 3 bd · 2 ba · 1,782 sq ft · 97 days on market Courtesy of EXP REALTY LLC
- 2925 Willow Creek Lane $395,000 · 3 bd · 2 ba · 1,797 sq ft · 181 days on market Courtesy of SOVEREIGN REAL ESTATE GROUP
Checked against the MLS Oct 18, 2026. All new listings in this market.
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- White Cedar Circle (27 homes on record)
- White Cedar Circle (18 homes on record)
- White Cedar Circle (13 homes on record)
Frequently Asked Questions
What is the median home price in Windsor Point?
How long do homes in Windsor Point take to sell?
Is Windsor Point a buyer's or seller's market right now?
How many homes are in Windsor Point?
What share of Windsor Point is owner-occupied?
When were the homes in Windsor Point built?
Do cash buyers compete in Windsor Point?
Who is the best real estate agent for Windsor Point?
How do I find a top Kissimmee real estate agent who knows Windsor Point?
Can Momentum Realty connect me with an agent for Windsor Point?
Where is Windsor Point, and what county is it in?
Should you buy in Windsor Point?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 17, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2007 (40 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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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.
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See how WINDSOR POINT fits the bigger picture — live prices, inventory, and Momentum Scores:
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More on Windsor Point
- Home values · What homes in Windsor Point actually sell for