Windsor Hills
Homes for Sale in Kissimmee, FL
All 2,959 homes for sale in KISSIMMEE, FL · median $374,000 · 803 homes for sale in 34746 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Over the 12 months ending 2026-08-02, 56 recorded sales closed at a median of $595,000, $263 per square foot, a median 27 days on market, sellers accepting 97% of original asking (+4% versus the prior year). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $9,060 ($8,460 with the full homestead exemption).
Part of the Windsor Hills master-planned community in Kissimmee, FL — see all Windsor Hills homes for sale (34 listings across 4 villages and sections in the MLS).
Windsor Hills is a mid-2000s community in Kissimmee, with homes built between 2004 and 2006 and a median living area right around 1,451 square feet. The homestead share here is under 2%, which tells you almost everything about how this market behaves: this is not a primary-residence enclave. Pricing is driven by rental and second-home demand far more than by owner-occupant turnover, so condition, furnishings, and rental performance move value more than square footage alone.
With so little owner-occupancy, expect a wide spread between a tired, turnkey-in-name-only unit and a well-kept, rental-ready one. The single median price is your anchor; treat everything above and below it as a condition-and-performance story, not a size story. For sellers, presentation and documented rental history carry weight. For buyers, underwrite the numbers, not the photos.
Windsor Hills right now
🟡 Still climbing. The trailing-12-month median ($595K) is up 4.4% from the prior 12 months ($570K) and up 90% since 2012.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending August 2. Confidence: Very High (56 and 47 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated September 27, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside WINDSOR HILLS PH 02 right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Windsor Hills market snapshot (as of August 2, 2026): the median sale price is about $595K ($263 per sq ft over the trailing 12 months of closed sales), and a median 27 days on market for closed sales. The trailing-12-month median is up 4% from the prior 12 months and up 90% since 2012, computed from record-level Stellar MLS closed sales (56 closings in the current window).
In ZIP 34746 (KISSIMMEE), 1,623 homes closed in the last 12 months at a median of $405K ($199/sq ft), down 4.3% year over year, with a median 67 days on market. Right now 435 active and 80 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 948 homes in Kissimmee, Osceola County, built between 2004 and 2010 (median 2005), with a median living area of about 1,595 square feet. 2% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a uniform, purpose-built community from the mid-2000s where the homes were designed and bought largely as short-term-rental and second-home product rather than year-round residences. That single fact shapes pricing, competition, and how you should evaluate any listing here.
Who Windsor Hills is best for.
Best for
- Investors seeking a short-term-rental or vacation-use property in an established mid-2000s community
- Buyers who will underwrite a purchase on condition and operating numbers rather than square footage
- Second-home buyers comfortable with HOA rules and rental-market dynamics
Probably not for
- Buyers wanting a primary residence in an owner-occupant-dominated neighborhood
- Buyers who need a large or highly customized floor plan beyond the compact norm here
- Buyers unwilling to scrutinize condition, HOA terms, and rental performance before offering
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 ($595K) IS the median in the snapshot above, and the move from 2025 ($570K) IS the +4.4% one-year change.
Windows contain 0 to 84 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.
21% of homes for sale in ZIP 34746 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 (2026-08-01).
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 rental-market community, not an owner-occupant one
With 258 homes and a homestead share below 2%, Windsor Hills functions as an investment and vacation-use market. The build window of 2004 to 2006 means the housing stock is broadly consistent in age and layout, so differentiation comes down to upkeep, updates, and how the unit has been operated. Two homes of nearly identical size can trade very differently depending on condition and rental readiness.
The median living area near 1,451 square feet keeps these homes in a compact, manageable footprint. Because owner-occupancy is minimal, the practical questions are operational: HOA rules, rental permissions, management costs, and the state of the interior. Those factors, not raw dimensions, are what separate a strong buy from a money pit here.
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 (5.4). Basis: Long-Term Appreciation +90% since 2012; Recent Direction +4.4% year-over-year; Owner Commitment 2% owner-occupied; Pricing Power 96.6% sale-to-list. Refreshed with each data update.
Why work with Momentum here
A community this investment-driven rewards analysts, not optimists. We read condition against the median, dig into HOA and rental parameters, and help you separate a turnkey performer from a cosmetic listing. Whether you are buying to operate or selling and need to position against near-identical inventory, we work the numbers before the narrative.
Windsor Hills in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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 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 homes for sale in Windsor Hills on the map →
Frequently Asked Questions
What is the median home price in Windsor Hills?
How long do homes in Windsor Hills take to sell?
How many homes are in Windsor Hills?
What share of Windsor Hills is owner-occupied?
When were the homes in Windsor Hills built?
Do cash buyers compete in Windsor Hills?
Have Windsor Hills home prices gone up?
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 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
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (51 streets, ZIP 34744/34746/34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2009 (442 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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More Kissimmee & Kissimmee, St. Cloud & Osceola County guides
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See how WINDSOR HILLS PH 02 fits the bigger picture — live prices, inventory, and Momentum Scores:
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