Windsor Hills
Homes for Sale in Kissimmee, FL
All 2,920 homes for sale in Kissimmee, FL · median $374,990 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
As of September 2026, windsor hills in Kissimmee, FL has 27 homes for sale and 4 pending, asking from $380,000 to $699,900 (median $589,999). Over the 12 months ending 2026-09-12, 56 recorded sales closed at a median of $597,500, $260 per square foot, a median 25 days on market, sellers accepting 97% of original asking (+4% versus the prior year). Homes listed or recently sold were built 2004 - 2008; 42 of 43 report an HOA (median $171/mo); none of the 38 geocoded homes sit in a FEMA special flood hazard zone (median elevation 118 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $9,100 ($8,500 with the full homestead exemption).
Villages & sections of Windsor Hills
Windsor Hills in Kissimmee, FL is a master-planned community recorded as 4 named villages and sections in the MLS; 2 homes are for sale or pending across them today. Each village has its own page with its listings, sales history and HOA/CDD facts.
- Windsor Hills Ventura at Windsor Hills · 2 for sale
- Windsor Hills Ph 02 · 56 sold/12 mo
- Ventura at Windsor Hills Condo Ph 3 · 23 sold/12 mo
- Ventura at Windsor Hills Windsor Hills
Homes For Sale Right Now in Windsor Hills
Live MLS inventory for Windsor Hills. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active · 1 daysTop listing
Active · 12 days
Active · 1 days
Active · 40 days
Active · 78 days
Active · 49 days
Active · 226 days
Active · 25 days
Active · 5 days
Active · 132 days
Active · 20 days
Active · 8 days
Active · 80 days
Active · 562 daysActive and pending Windsor Hills listings as of 2026-09-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2009 through 2026. Tap any home to ask about it.
Windsor Hills right now
🟡 Balanced market. 5.2 months of supply and 13% of the inventory already under contract put buyers and sellers on roughly even footing.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 12, 2026. Confidence: Very High (31 active and pending listings, 56 closed sales in 12 months).
🟡 Still climbing. The trailing-12-month median ($598K) is up 3.9% from the prior 12 months ($575K).Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 12. Confidence: Very High (56 and 51 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 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 Hills market snapshot (as of September 12, 2026): the median sale price is about $598K ($260 per sq ft over the trailing 12 months of closed sales), a median 25 days on market for closed sales, and 5.2 months of supply, a balanced market. The trailing-12-month median is up 4% from the prior 12 months, computed from record-level Stellar MLS closed sales (56 closings in the current window).
Flood zones in windsor hills: of 38 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.
In ZIP 34746 (Kissimmee), 1,615 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.5% year over year, with a median 67 days on market. Right now 421 active and 72 pending listings put supply at about 6.7 months - a buyer's market. See the live ZIP 34746 housing market and the Osceola County market.
Windsor Hills is a community of 539 homes in Kissimmee, Osceola County, built between 2004 and 2010 (median 2005.0), with a median living area of about 2,634 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 Hills. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Windsor Hills
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Windsor HillsWindsor HillsWindsor HillsPhotos from Stellar MLS listings in Windsor Hills; 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 12 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($598K) IS the median in the snapshot above, and the move from 2025 ($575K) IS the +3.9% one-year change.
Windows contain 0 to 79 sales each (56 in the current window); every figure carries its sample size. Based on Stellar MLS data distributed by MLS GRID for the period 2009 through 2026. Deemed reliable but not guaranteed.
WINDSOR HILLS PHASE THREE Market Scorecard
WINDSOR HILLS PHASE THREE is currently a balanced market. About 5.2 months of supply, a median asking price of $589,999, and homes go under contract in about 49 days.
Typical home value in the 34747 ZIP is $400,438, about 3.4% below the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · 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 hills, 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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Windsor Hills 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 Hills
- Fitness Center · reported on 29 of 34 listings
- Pool · reported on 28 of 34 listings
- Playground · reported on 26 of 34 listings
- Clubhouse · reported on 25 of 34 listings
- Gated Community - Guard · reported on 25 of 34 listings
- Tennis Court(s) · reported on 24 of 34 listings
- Park · reported on 14 of 34 listings
- Gated · reported on 13 of 34 listings
- Basketball Court · reported on 10 of 34 listings
- Cable TV · reported on 9 of 34 listings
- Deed Restrictions · reported on 9 of 34 listings
- Security · reported on 9 of 34 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
- Island Village Elementary School · Elementary
- Celebration K-8 · Middle
- Celebration High · High
Zoned schools reflect the assignments reported on recent Windsor Hills 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 Hills address.
Shop the zone: Homes zoned for Celebration High High School
The Windsor Hills buying strategy.
If we were buying in Windsor Hills 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.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
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 Hills.
A closer look at the Windsor Hills market
At a median of $260 per square foot, Windsor Hills 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 5.2 months of supply, a balanced market and the trailing-12-month median up 4% year over year. Homes that do trade take a median 25 days on market, useful leverage on any listing that has lingered.
The housing stock is 539 homes built between 2004 and 2010, 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 Hills. 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 Hills 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 (5.0). Basis: Recent Direction +3.9% year-over-year; Liquidity & Demand 5.2 months of supply; Owner Commitment 1% owner-occupied; Pricing Power 97.0% sale-to-list. Refreshed with each data update.
HOA, CDD & Fees
- HOA dues reported around $171/month (about $2,052/yr) · median of 84 MLS listings, most billed quarterly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $171 per month ($2,052 a year) - the median AssociationFee across 84 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, 2026-09.
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 Hills 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 Hills sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor Hills, 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 Hills home worth?
Get a no-obligation home value based on real comparable sales in Windsor Hills, 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 hills
Homes in windsor hills 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. 5 on record.
- 2630 Dinville Street · off market
- 2648 Dinville Street · off market
- 2689 Manesty Lane · off market
- 7716 Comrow Street · off market
- 7750 Teascone Boulevard · off market
Frequently Asked Questions
What is the median home price in Windsor Hills?
How long do homes in Windsor Hills take to sell?
Is Windsor Hills a buyer's or seller's market right now?
How many homes are in Windsor Hills?
What share of Windsor Hills is owner-occupied?
When were the homes in Windsor Hills built?
Who is the best real estate agent for Windsor Hills?
How do I find a top Kissimmee real estate agent who knows Windsor Hills?
Can Momentum Realty connect me with an agent for Windsor Hills?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 14, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 12, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (12 streets, ZIP 34746/34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2009 (450 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 local comps.
Looking to buy here? Search homes for sale →
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See how windsor hills fits the bigger picture — live prices, inventory, and Momentum Scores:
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