WINDSOR POINT
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
Market Heat
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 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 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).
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 POINTWho 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.
WINDSOR POINT Market Scorecard
WINDSOR POINT is currently a buyer's market. About 9.0 months of supply, a median asking price of $429,000, and homes go under contract in about 65 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 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 August 2026 through August 2026. Deemed reliable but not guaranteed.
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 · 37 days
Active · 97 daysActive and pending WINDSOR POINT listings as of 2026-08-23, 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 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 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.
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.
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 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 homes for sale in WINDSOR POINT on the map →
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?
Should you buy in WINDSOR POINT?
An honest fit check. We will tell you when it is not your community.
Nearby Communities
Explore more neighborhoods near WINDSOR POINT 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 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.
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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See how WINDSOR POINT fits the bigger picture — live prices, inventory, and Momentum Scores:
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