Windsor Hills
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 hills in Kissimmee, FL has 31 homes for sale and 4 pending, asking from $270,000 to $729,000 (median $585,000). Over the 12 months ending 2026-11-13, 17 recorded sales closed at a median of $615,000, $248 per square foot, a median 29 days on market, sellers accepting 97% of original asking. Homes listed or recently sold were built 2004 - 2008; 47 of 47 report an HOA (median $171/mo); none of the 46 geocoded homes sit in a FEMA special flood hazard zone (median elevation 121 ft). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $9,370 ($8,770 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; 3 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 · 3 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
Last 30 days in Windsor Hills: 9 new listings (median asking $649,000), 4 under contract right now, 6 closed sales (median $595,500). As of November 13, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
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 · 23 daysTop listing
Active · 92 days
Active · 12 days
Active · 20 days
Active · 154 days
Active · 122 days
Active · 137 days
Active · 1 days
Active · 21 days
Active · 306 days
Active · 208 days
Active · 94 days
Active · 67 days
Active · 86 daysActive and pending Windsor Hills listings as of 2026-11-13, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2018 through 2026. Tap any home to ask about it.
Windsor Hills is a guard-gated resort community built in a tight window from 2004 to 2010, so the housing stock is consistent in age and generous in size, with a median around 2,634 square feet. The median sits at $600,000, but with a homestead share near 1%, this is overwhelmingly an investment and short-term-rental market, and what sets price here is less about location than about condition, furnishing package, and rental performance. Two homes of the same floor plan can trade far apart depending on how they're set up to produce income.
At 5.2 months of supply the market reads balanced, with a median of 26 days on market and 28 active listings against 57 recent closings. Prices are up 4.8% year over year. For sellers, that posture means you can hold your number if the home shows and rents well, but you won't dictate terms. For buyers, there's room to negotiate and time to underwrite the rental math before committing.
Figures in this note are as of October 26, 2026. The live market numbers elsewhere on this page update nightly and are newer.
Windsor Hills right now
🟢 Buyer-leaning market. 21.9 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 (35 active and pending listings, 17 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 Hills market snapshot (as of November 13, 2026): the median sale price is about $615K ($248 per sq ft over the trailing 12 months of closed sales), a median 29 days on market for closed sales, and 21.9 months of supply, a buyer-leaning market.
County records show 64 qualified sales in windsor hills across 2024 - 2025 (36 in 2024, 28 in 2025), median $550,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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.
Flood zones in Windsor Hills: of 39 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 Hills is a community of 576 homes in Kissimmee, Osceola County, built between 2004 and 2010 (median 2005), 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).
This is a guard-gated, deed-restricted resort community where the amenity package and short-term-rental orientation drive most buying decisions. Expect to evaluate homes as income-producing assets as much as residences.
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.
Who Windsor Hills is best for.
Best for
- Buying to operate a short-term rental inside a gated, amenity-rich resort community
- Buyers who want consistent 2004-to-2010 construction and generous square footage near 2,634 feet
- Investors willing to underwrite condition, furnishing, and booking performance before offering
Probably not for
- Buying a primarily owner-occupied home on a quiet street with little rental activity
- Buyers who want to avoid HOA deed restrictions and short-term-rental rules
- Anyone expecting price to track a single number rather than condition and income
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 ($615K) IS the median in the snapshot above.
Windows contain 0 to 17 sales each (17 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 2018 through 2026. Deemed reliable but not guaranteed.
11% of homes for sale in Windsor Hills 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 HILLS PHASE THREE Market Scorecard
WINDSOR HILLS PHASE THREE is currently a strong buyer's market. About 31.0 months of supply, a median asking price of $585,000, and homes go under contract in about 122 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 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 contributors.
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.
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 Hills.
A resort-rental market first
The amenity list reads like a resort rather than a subdivision: guard-gated entry, clubhouse, fitness center, pool and spa, tennis and basketball courts, playground, and park space, all under deed restrictions and HOA management. That package is the product here, because the near-total absence of homesteaded owners tells you most homes are run as short-term rentals. Verify current amenity access, rental rules, and HOA terms directly before you underwrite anything.
Because condition and furnishing drive value in a rental community, the spread between the best-prepared homes and the tired ones is wide even within a single floor plan. The median price of $600,000 and median price per square foot near $260 are useful anchors, but the right read on any individual home depends on how it shows, how it's furnished, and how it books. That's where diligence pays.
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 3 factors (2.8). Basis: Liquidity & Demand 21.9 months of supply; Owner Commitment 1% owner-occupied; Pricing Power 97.3% sale-to-list. Refreshed with each data update.
Why work with Momentum here
A resort-rental community rewards buyers and sellers who treat the home as an operating asset. We help you separate the homes that are priced on income performance from the ones that are priced on hope, read the HOA and deed restrictions that govern short-term use, and position a listing to show well against the comparable floor plans that actually compete with it.
Windsor Hills in 15 seconds.
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. 13 on record.
- 2500 Renshaw Street · off market
- 2534 Maneshaw Lane · off market
- 2630 Dinville Street · off market
- 2648 Daulby Street · off market
- 2689 Manesty Lane · off market
- 7667 Otterspool Street · off market
- 7677 Fitzclarence Street · off market
- 7716 Comrow Street · off market
| Location | Kissimmee, Osceola County, FL · ZIP 34747 |
|---|---|
| Homes in the community | 576 (FL DOR 2025 assessment roll) |
| Years built | 2004–2010 (median 2005) |
| Typical living area | 2,634 sq ft (median) |
| Home types (current listings and sales) | single-family 60%, townhouses 36% |
| Amenities listed by sellers | Pool, Fitness Center, Clubhouse, Gated Community - Guard, Playground, Tennis Court(s) |
| Sale prices, last 12 months | $615,000 median across 17 closed sales · $248 per sq ft |
| Days on market (closed sales) | 29 median |
| For sale right now | 31 active, 4 pending · median asking $585,000 · 21.9 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 2018 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Windsor Hills key facts,” movewithmomentum.com/neighborhoods/windsor-hills-phase-three-kissimmee, data as of November 13, 2026.
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 November 2026 through November 2026. Deemed reliable but not guaranteed.
Just listed in Windsor Hills
The newest homes for sale in Windsor Hills right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 2687 Manesty Lane $649,900 · 5 bd · 5 ba · 2,342 sq ft · listed Nov 12, 2026 Courtesy of REAL BROKER, LLC
- 7670 Otterspool Street $459,000 · 3 bd · 3 ba · 1,440 sq ft · listed Nov 11, 2026 Courtesy of REAL BROKER, LLC
- 2553 Maneshaw Lane $439,000 · 3 bd · 3 ba · 1,440 sq ft · listed Nov 6, 2026 Courtesy of COMPASS FLORIDA LLC
- 2579 Maneshaw Lane $470,000 · 3 bd · 3 ba · 1,440 sq ft · listed Nov 5, 2026 Courtesy of REAL BROKER, LLC
- 2564 Archfeld Boulevard $695,000 · 6 bd · 4 ba · 2,812 sq ft · listed Nov 2, 2026 Courtesy of OLYMPUS EXECUTIVE REALTY INC
- 2788 Almaton Loop #102 $270,000 · 2 bd · 2 ba · 1,081 sq ft · listed Oct 26, 2026 Courtesy of LPT REALTY, LLC
Checked against the MLS nightly. All new listings in this market.
Every Home for Sale in Windsor Hills Phase Three Kissimmee Right Now (34)
All 34 active and pending Windsor Hills Phase Three Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2687 Manesty Lane · $649,900 · 5 bd / 5 ba · listed Nov 12, 2026 · listed by Real Broker, Llc
- 7670 Otterspool Street · $459,000 · 3 bd / 3 ba · listed Nov 10, 2026 · listed by Real Broker, Llc
- 2593 Maneshaw Lane · $360,000 · 3 bd / 3 ba · pending · listed Nov 7, 2026 · listed by Creegan Group
- 2579 Maneshaw Lane · $470,000 · 3 bd / 3 ba · listed Nov 5, 2026 · listed by Real Broker, Llc
- 2553 Maneshaw Lane · $439,000 · 3 bd / 3 ba · listed Nov 4, 2026 · listed by Compass Florida Llc
- 2564 Archfeld Boulevard · $695,000 · 6 bd / 4 ba · listed Nov 1, 2026 · listed by Olympus Executive Realty Inc
- 2669 Manesty Lane · $678,000 · 6 bd / 4 ba · listed Oct 24, 2026 · listed by Ratio Real Estate, Llc
- 2788 Almaton Loop #102 · $270,000 · 2 bd / 2 ba · listed Oct 23, 2026 · listed by Lpt Realty, Llc
- 2648 Dinville Street · $649,000 · 5 bd / 5 ba · listed Oct 23, 2026 · listed by Lpt Realty, Llc
- 2624 Bowring Street · $729,000 · 6 bd / 4 ba · listed Oct 20, 2026 · listed by Holiday Realty Llc
- 7769 Teascone Boulevard · $610,000 · 5 bd / 5 ba · pending · listed Sep 26, 2026 · listed by Alliance Real Estate Group
- 2592 Maneshaw Lane · $419,000 · 3 bd / 3 ba · listed Sep 18, 2026 · listed by La Rosa Realty Llc
- 2536 Holtrock Street · $698,000 · 6 bd / 4 ba · listed Sep 10, 2026 · listed by Ratio Real Estate, Llc
- 7674 Otterspool Street · $425,000 · 3 bd / 3 ba · listed Sep 10, 2026 · listed by La Rosa Realty Llc
- 2545 Renshaw Street · $409,000 · 3 bd / 3 ba · listed Sep 10, 2026 · listed by Exp Realty Llc
- 7742 Comrow St · $699,900 · 5 bd / 5 ba · pending · listed Sep 10, 2026 · listed by Hopkey Realty
- 2671 Manesty Lane · $620,000 · 6 bd / 4 ba · listed Sep 6, 2026 · listed by Alliance Real Estate Group
- 7743 Comrow Street · $675,000 · 4 bd / 4 ba · listed Sep 2, 2026 · listed by Real Broker, Llc
- 7795 Basnett Circle · $599,900 · 5 bd / 5 ba · listed Aug 21, 2026 · listed by The Agency Fl
- 7777 Teascone Boulevard · $629,000 · 5 bd / 5 ba · listed Aug 16, 2026 · listed by Frontline Florida Realty, Inc.
- 2530 Maneshaw Lane · $419,000 · 3 bd / 3 ba · listed Aug 15, 2026 · listed by Exp Realty Llc
- 7765 Tosteth Street · $659,000 · 6 bd / 4 ba · listed Aug 15, 2026 · listed by Florida 360 Realty Llc
- 7683 Fitzclarence Street · $395,000 · 3 bd / 3 ba · listed Aug 15, 2026 · listed by Kressler Real Estate
- 2623 Pawnall Street · $655,000 · 6 bd / 4 ba · listed Aug 15, 2026 · listed by Exp Realty Llc
- 7654 Otterspool Street · $394,000 · 3 bd / 3 ba · listed Aug 15, 2026 · listed by La Rosa Realty Llc
- 7755 Grassendale Street · $585,000 · 4 bd / 4 ba · listed Aug 15, 2026 · listed by Florida Realty Results Llc
- 2621 Archfeld Boulevard · $639,000 · 5 bd / 5 ba · listed Aug 15, 2026 · listed by Mainframe Real Estate
- 2556 Renshaw Street · $394,000 · 3 bd / 3 ba · listed Aug 15, 2026 · listed by Luxe Properties Llc
- 7681 Sir Kaufmann Court · $399,000 · 3 bd / 3 ba · listed Aug 15, 2026 · listed by Stockworth Realty Group
- 7788 Basnett Circle · $645,000 · 5 bd / 5 ba · listed Aug 15, 2026 · listed by La Rosa Realty Llc
- 7739 Teascone Boulevard · $537,000 · 4 bd / 4 ba · listed Aug 15, 2026 · listed by Keller Williams Classic
- 7663 Sir Kaufmann Court · $380,000 · 3 bd / 3 ba · listed Aug 15, 2026 · listed by Blue Lighthouse Realty Inc
- 2615 Pawnall Street · $570,000 · 5 bd / 5 ba · listed Aug 15, 2026 · listed by The Property Firm
- 2568 Archfeld Boulevard · $569,900 · 4 bd / 4 ba · pending · listed Aug 15, 2026 · listed by Global Florida Realty
Recently sold in Windsor Hills Phase Three Kissimmee
- 7667 Otterspool Street · sold $445,000
- 7677 Fitzclarence Street · sold $393,000
- 7772 Basnett Circle · sold $680,000
- 7759 Tosteth Street · sold $601,000
- 7805 Beechfield Street · sold $640,000
- 7745 Teascone Boulevard · sold $590,000
- 2500 Renshaw Street · sold $433,000
- 2534 Maneshaw Lane · sold $357,000
- 2648 Daulby Street · sold $615,000
- 7716 Comrow Street · sold $634,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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Florida buyer guides
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What it really costs to own in Windsor Hills
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 $171/month across 49 MLS listings (most billed quarterly; 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 39 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 2005 across 45 listings. An original roof here would be about 21 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 Hills
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 Hills
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Windsor Hills 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 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?
Where is Windsor Hills, and what county is it in?
Is Windsor Hills in a flood zone?
Is Windsor Hills a good place to live?
Should you buy in Windsor Hills?
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: November 13, 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 (13 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-11-13 |
| Historical depth | Closed-sale records back to 2018 (18 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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See how windsor hills fits the bigger picture — live prices, inventory, and Momentum Scores:
