Windsor Hills Ph 2
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Windsor Hills Ph 2 is a mid-2000s community in Kissimmee, with homes built between 2004 and 2008 and a median around 1,451 square feet. What sets price here is condition and finish rather than age — the stock is tightly clustered in vintage, so a buyer is largely paying for how well a specific home has been maintained and updated. The median sits at $406,450, roughly $276 per square foot, and prices have moved up 1.9% year over year, which reads as flat-to-steady rather than a market on the run.
The posture right now is patient on both sides. A median of about 51 days on market — call it just over 50 days — tells you homes are not clearing in a weekend; buyers have room to inspect, negotiate, and walk if the numbers don't work. Sellers should price to the comparable condition, not to a hoped-for ceiling, because the days-on-market data says the pool of buyers is deliberate. One note worth flagging: the homestead share is very low, near 1.6%, which points to a community held largely as non-primary residences — relevant for anyone weighing rental use and HOA rules.
Windsor Hills Ph 2 right now
🟡 Still climbing. The trailing-12-month median ($406K) is up 1.9% from the prior 12 months ($399K). With about 3 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 July 13. Confidence: Medium (18 and 7 sales in the two windows).
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Updated July 13, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Windsor Hills Ph 2 right now
🟡 Still climbing. The trailing-12-month median ($406K) is up 1.9% from the prior 12 months ($399K). With about 3 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 July 13. Confidence: Medium (18 and 7 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated July 13, 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 Ph 2 market snapshot (as of July 13, 2026): the median sale price is about $406K ($276 per sq ft over the trailing 12 months of closed sales), and a median 52 days on market for closed sales. The trailing-12-month median is up 2% from the prior 12 months, computed from record-level Stellar MLS closed sales (18 closings in the current window).
Windsor Hills Ph 2 is a community of 319 homes in Kissimmee, Osceola County, built between 2004 and 2008 (median 2005), with a median living area of about 1,451 square feet. 2% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
This is a compact, uniform community of 319 homes from a single mid-2000s building era, so the shopping decision comes down to condition and layout rather than a wide span of vintages or sizes.
Who Windsor Hills Ph 2 is best for.
Best for
- Buyers targeting a right-sized home near the mid-$400s who value clean, apples-to-apples comparables
- Investors who have confirmed the HOA's rental policy and want a low-owner-occupancy community
- Purchasers who are patient and want negotiating room rather than a fast, competitive close
Probably not for
- Buyers wanting a wide spread of home sizes or newer construction than the 2004–2008 vintage
- Anyone assuming short-term rental is allowed without checking the governing documents first
- Sellers or buyers expecting rapid turnover in a market averaging just over 50 days on market
Median sale price over the trailing 12 months ending July 13 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($406K) IS the median in the snapshot above, and the move from 2025 ($399K) IS the +1.9% one-year change.
Windows contain 0 to 18 sales each (18 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 %s through %s. Deemed reliable but not guaranteed.
The Windsor Hills Ph 2 buying strategy.
If we were buying in Windsor Hills Ph 2 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 Ph 2.
A single-era community priced on condition
With every home built inside a five-year window and a median living area near 1,451 square feet, Windsor Hills Ph 2 offers little variety in bones — which is actually useful when you're comparing. Two homes of similar footprint should trade close together unless one has been meaningfully updated or deferred. That makes inspection and finish quality the real levers on price, and it rewards buyers who look past staging to the mechanicals and roof age typical of 2004–2008 construction.
The very low homestead share is the defining structural fact here. A community where owner-occupancy is the exception tends to function differently — turnover, upkeep patterns, and HOA priorities all lean toward non-primary use. If your plan involves short-term or seasonal rental, confirm what the current governing documents allow before you write an offer, because that policy, not the list price, may be the thing that makes or breaks the investment.
The location and the amenities are priced into every listing in Windsor Hills Ph 2. 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 Ph 2 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 (4.6). Basis: Recent Direction +1.9% year-over-year; Owner Commitment 2% owner-occupied; Pricing Power 95.7% sale-to-list. Refreshed with each data update.
Why work with Momentum here
In a single-era community, the edge is knowing which homes have been kept up and which have been coasting on 2005 systems — and reading the HOA rules that govern rental use, which matter more here than in most Kissimmee communities. We price to condition, not to a hopeful ceiling, and with homes sitting just over 50 days on market we help buyers use that time to negotiate rather than rush.
Windsor Hills Ph 2 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 Hills Ph 2 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 Ph 2 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 Ph 2, 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 Ph 2 home worth?
Get a no-obligation home value based on real comparable sales in Windsor Hills Ph 2, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Frequently Asked Questions
What is the median home price in Windsor Hills Ph 2?
How long do homes in Windsor Hills Ph 2 take to sell?
How many homes are in Windsor Hills Ph 2?
What share of Windsor Hills Ph 2 is owner-occupied?
When were the homes in Windsor Hills Ph 2 built?
Do cash buyers compete in Windsor Hills Ph 2?
Who is the best real estate agent for Windsor Hills Ph 2?
How do I find a top Kissimmee real estate agent who knows Windsor Hills Ph 2?
Can Momentum Realty connect me with an agent for Windsor Hills Ph 2?
Should you buy in Windsor Hills Ph 2?
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 July 13, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (7 streets, ZIP 34746/34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2012 (37 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.
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 13 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($406K) IS the median in the snapshot above, and the move from 2025 ($399K) IS the +1.9% one-year change.
Windows contain 0 to 18 sales each (18 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 %s through %s. Deemed reliable but not guaranteed.
Data sources & freshness
| Community market stats | Stellar MLS closed sales, 12-month windows ending July 13, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (7 streets, ZIP 34746/34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2012 (37 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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