Windsor Hills Ph 4
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
120 homesBuilt 2005–2005Median sale $400K
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Live · Windsor Hills Ph 4 Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Price
$400K
Median sold · 12 mo
up 2.6% vs the prior 12 months
+2.6%
1-yr price change
n = 7 and 7 sales in the two windows
$278/sf
Sold $/sqft · 12 mo
peak $278 in 2026
95.2%
Sale vs ask
Osceola median: 95.9%
Tempo
34days
Median DOM · closed
34 days at the 2026 low
7
Sold · last 12 mo
10-yr average: about 2 a year
Ownership and context
2%
Owner-occupied · Windsor Hills Ph 4
3 of 120 parcels homesteaded (FL DOR 2025)
98%
Non-owner-occupied · Windsor Hills Ph 4
incl. 21% trust or LLC-held · 77% out-of-state
25%
Cash buyers · Windsor Hills Ph 4
2 of 8 sales, 12 mo ending June 2026
120
Homes in the community
120 residential parcels (FL DOR 2025)
Track record · 15 years of records
Est. 2005
Community established
homes built 2005-2005, median 2005 (FL DOR 2025)
2
Failed listings · 2026
peaked at 18 in 2008
1,440sqft
Median sold home size
12-mo windows, closed sales
5.8%/yr
Turnover rate
about 7 of 120 homes trade a year
Built fromLive Stellar MLS data15 years of closingsFL DOR public recordsUpdated twice daily
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Windsor Hills Ph 4 is a single-vintage pocket — everything here dates to 2005, with a median footprint around 1,448 square feet. When the age and layout of the stock are this uniform, price is set less by what year a home went up and more by condition, finish level, and furnishing. The median sits at $400,000, roughly $278 per square foot, and the spread around that number is driven by how much work a given unit has had, not by neighborhood tiering.

The current posture is balanced-to-brisk: a median of 34 days on market and year-over-year movement of 2.6% say this is a steady market, not a runaway one. For a seller, that means condition and presentation carry the negotiation — a turnkey unit clears faster than a tired one at the same address. For a buyer, there's time to inspect and underwrite properly without the pressure of a bidding frenzy. The homestead share here is very low at 2.5%, which tells you most of this stock trades as something other than an owner's primary residence — plan your due diligence and financing accordingly.

Windsor Hills Ph 4 Housing Pulse · Momentum Research · as of July 13, 2026

Windsor Hills Ph 4 right now

🟡 Still climbing. The trailing-12-month median ($400K) is up 2.6% from the prior 12 months ($390K). 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 July 13. Confidence: Medium (7 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

Windsor Hills Ph 4 Housing Pulse · Momentum Research · as of July 13, 2026

Windsor Hills Ph 4 right now

🟡 Still climbing. The trailing-12-month median ($400K) is up 2.6% from the prior 12 months ($390K). 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 July 13. Confidence: Medium (7 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 4 market snapshot (as of July 13, 2026): the median sale price is about $400K ($278 per sq ft over the trailing 12 months of closed sales), and a median 34 days on market for closed sales. The trailing-12-month median is up 3% from the prior 12 months, computed from record-level Stellar MLS closed sales (7 closings in the current window).

Windsor Hills Ph 4 is a community of 120 homes in Kissimmee, Osceola County, built between 2005 and 2005 (median 2005.0), with a median living area of about 1,448 square feet. 2% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

A compact, uniformly 2005-built community of about 120 homes near Kissimmee's tourist corridor, where the very low homestead share signals a market dominated by second-home and rental use rather than year-round owner occupancy.

Best for

  • A buyer near the $400,000 median seeking a second home in a consistent, single-vintage community
  • An investor comfortable underwriting a short-term or rental-use property after verifying HOA rules
  • A buyer who values clean comparables and a steady ~34-day market over speculative upside

Probably not for

  • A buyer who needs a primary-residence homestead setting with mostly owner-occupied neighbors
  • A buyer expecting a wide range of home ages, sizes, and floorplans to choose from
  • A buyer whose budget or financing depends on owner-occupant terms and can't accommodate investment-use lending

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 ($400K) IS the median in the snapshot above, and the move from 2025 ($390K) IS the +2.6% one-year change.

Windows contain 0 to 7 sales each (7 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.

Homes sold per 12-mo window
024620122014201620182020202220242026
0 to 7 a year; 7 in the current window.
Sellers who gave up · failed listings per year
05101520062008201020122014201620242026
Canceled, expired, or withdrawn. 18 quit in 2008; 2 so far in 2026. The clearest stress gauge a community has.

If we were buying in Windsor Hills Ph 4 today, this is the order of operations we would run for our clients.

1

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.

2

Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.

3

Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.

4

Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.

5

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 4.

Best Buy
Buyers pursuing a second home or income-oriented property in a uniform, low-maintenance-age community.
Biggest Risk
A 2.5% homestead share means this trades as investment stock — resale liquidity and financing follow that reality.
Sweet Spot
A well-maintained, rental-ready unit priced honestly against the $400,000 median clears at a reasonable pace.
Avoid If
You want a primary-residence neighborhood of year-round owner occupants.

One vintage, condition is the variable

Because every home traces to a single build year and the median living area lands near 1,448 square feet, buyers here are comparing largely similar boxes. That simplifies one thing and complicates another: floorplans won't vary wildly, but wear, updates, and — given the low homestead share — furnishing and rental readiness will. Two units at the same $400,000 median can be very different purchases depending on how they've been maintained and equipped.

The 2.5% homestead share is the single most important fact in this snapshot. It points to a community used heavily for short-term or investment purposes rather than primary living. That shapes financing, HOA rules to verify, insurance, and resale liquidity. Read the community documents closely on rental permissions and fees before you write an offer, because the assumptions that work in an owner-occupied neighborhood do not automatically transfer here.

The location and the amenities are priced into every listing in Windsor Hills Ph 4. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty
4.6C- · Buy Score
Recent Direction6.7/10
Owner Commitment0.2/10
Pricing Power6.8/10

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 +2.6% year-over-year; Owner Commitment 2% owner-occupied; Pricing Power 95.2% sale-to-list. Refreshed with each data update.

Why work with Momentum here

In a community where nearly all the stock trades as investment or second-home product, the deal lives in the details — rental rules, furnishing, condition, and how a 34-day median actually behaves for your specific unit. We price to condition rather than to a headline number, verify the HOA and use restrictions before you're committed, and tell you plainly when the math doesn't support the plan.

Windsor Hills Ph 4 in 15 seconds.

Best forBuyers pursuing a second home or income-oriented property in a uniform, low-maintenance-age community.
Biggest advantageA single 2005 vintage and consistent footprint make comparables clean and underwriting straightforward.
Biggest riskA 2.5% homestead share means this trades as investment stock — resale liquidity and financing follow that reality.
Sweet spotA well-maintained, rental-ready unit priced honestly against the $400,000 median clears at a reasonable pace.
Avoid ifYou want a primary-residence neighborhood of year-round owner occupants.

HOA, CDD & Fees

In short
  • 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.

The takeaway

Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Windsor Hills Ph 4 sales matched to your home.

What is your Windsor Hills Ph 4 home worth?

Get a no-obligation home value based on real comparable sales in Windsor Hills Ph 4, 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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Real comps, not an automated estimate.

Frequently Asked Questions

What is the median home price in Windsor Hills Ph 4?
The median sale price in Windsor Hills Ph 4 was $400K over the 12 months ending July 13, 2026 (7 closed sales, Stellar MLS).
How long do homes in Windsor Hills Ph 4 take to sell?
Homes that closed in the 12 months ending July 13, 2026 took a median 34 days on market (7 sales, Stellar MLS).
How many homes are in Windsor Hills Ph 4?
The Florida DOR 2025 assessment roll shows 120 homes in Windsor Hills Ph 4 (public records).
What share of Windsor Hills Ph 4 is owner-occupied?
2% of Windsor Hills Ph 4 parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Windsor Hills Ph 4 built?
Homes in Windsor Hills Ph 4 were built between 2005 and 2005, with a median year built of 2005.0 (FL DOR 2025 roll).
Do cash buyers compete in Windsor Hills Ph 4?
Cash buyers took 25% of Windsor Hills Ph 4 sales in the 12 months ending June 2026 (2 of 8 closings, Stellar MLS).
Who is the best real estate agent for Windsor Hills Ph 4?
The best agent for Windsor Hills Ph 4 is one who actively works Kissimmee and knows the community's pricing, fees, and current inventory. Tell us what you're looking for in the form on this page and Momentum Realty will match you with a local specialist for Windsor Hills Ph 4.
How do I find a top Kissimmee real estate agent who knows Windsor Hills Ph 4?
Share a few details in the form on this page. Momentum Realty has 280+ agents and more than $3.5B in closed sales, and we'll connect you with one who knows Windsor Hills Ph 4 and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Windsor Hills Ph 4?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Windsor Hills Ph 4 purchase or sale - no call center and no pressure.
A buyer near the $400,000 median seeking a second home in a consistent, single-vintage communityExcellent fit
An investor comfortable underwriting a short-term or rental-use property after verifying HOA rulesExcellent fit
A buyer who values clean comparables and a steady ~34-day market over speculative upsideExcellent fit
A buyer who needs a primary-residence homestead setting with mostly owner-occupied neighborsProbably not
A buyer expecting a wide range of home ages, sizes, and floorplans to choose fromProbably not
A buyer whose budget or financing depends on owner-occupant terms and can't accommodate investment-use lendingProbably not

Data sources & freshness

Community market statsStellar MLS closed sales, 12-month windows ending July 13, 2026
Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34747))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2011 (25 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.

Windows contain 0 to 7 sales each (7 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.

Homes sold per 12-mo window
024620122014201620182020202220242026
0 to 7 a year; 7 in the current window.
Sellers who gave up · failed listings per year
05101520062008201020122014201620242026
Canceled, expired, or withdrawn. 18 quit in 2008; 2 so far in 2026. The clearest stress gauge a community has.

Data sources & freshness

Community market statsStellar MLS closed sales, 12-month windows ending July 13, 2026
Housing stock & ownershipFlorida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34747))
Under-contract sharesStellar MLS records, as of 2026-07-12
Historical depthClosed-sale records back to 2011 (25 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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