Windsor At Westside Ph 3A
Homes for Sale in Kissimmee, FL

Community in Kissimmee · Osceola County
100 homesBuilt 2019–2020Median sale $532K
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Built fromLive Stellar MLS data2 years of closingsFL DOR public recordsUpdated twice daily
Live · Windsor At Westside Ph 3A Housing Pulse Stellar MLS + public records Analysis by Momentum Realty · $3.5B+ sold · 8,500+ transactions · Top 1% in Florida (RealTrends)
Price
$532K
Median sold · 12 mo
down 2.9% vs the prior 12 months
-2.9%
1-yr price change
n = 9 and 3 sales in the two windows
$187/sf
Sold $/sqft · 12 mo
peak $191 in 2025
95.0%
Sale vs ask
Osceola median: 95.9%
Tempo
75days
Median DOM · closed
75 days at the 2026 low
9
Sold · last 12 mo
10-yr average: about 4 a year
Ownership and context
0%
Owner-occupied · Windsor At Westside Ph 3A
0 of 100 parcels homesteaded (FL DOR 2025)
100%
Non-owner-occupied · Windsor At Westside Ph 3A
incl. 40% trust or LLC-held · 52% out-of-state
22%
Cash buyers · Windsor At Westside Ph 3A
2 of 9 sales, 12 mo ending June 2026
100
Homes in the community
100 residential parcels (FL DOR 2025)
Track record · 2 years of records
Est. 2019
Community established
homes built 2019-2020, median 2020 (FL DOR 2025)
4
Failed listings · 2026
peaked at 8 in 2025
3,142sqft
Median sold home size
12-mo windows, closed sales
9.0%/yr
Turnover rate
about 9 of 100 homes trade a year
Jon Brooks, founder of Momentum Realty
Jon's Current Read

Windsor At Westside Ph 3A is a small, uniform pocket of about 100 homes built in 2019 and 2020, and that consistency is the story on price. With a median around $532,000 and a median near 2,745 square feet, what separates one closing from the next here is condition, finish level, and specific position within the community far more than age or size. The median of $186.6 per square foot is your anchor; treat anything materially above or below it as a signal to look harder at the individual home.

The current posture favors patience on both sides. A median of 75 days on market is a slow clock, and prices are off 2.9% year over year, so sellers should price to the market rather than to last year and expect to negotiate. Buyers have room to be selective and to underwrite carefully, but with a homestead share of zero, this is not an owner-occupied enclave — it reads as an investment- and second-home-oriented market, which shapes both demand and how you should model holding costs.

Windsor At Westside Ph 3A Housing Pulse · Momentum Research · as of July 13, 2026

Windsor At Westside Ph 3A right now

🟡 Off the recent peak. The trailing-12-month median ($532K) is down 2.9% from the prior 12 months ($548K). With about 4 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: Low (9 and 3 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 At Westside Ph 3A market snapshot (as of July 13, 2026): the median sale price is about $532K ($187 per sq ft over the trailing 12 months of closed sales), and a median 75 days on market for closed sales. The trailing-12-month median is down 3% from the prior 12 months, computed from record-level Stellar MLS closed sales (9 closings in the current window).

Windsor At Westside Ph 3A is a community of 100 homes in Kissimmee, Osceola County, built between 2019 and 2020 (median 2020.0), with a median living area of about 2,745 square feet. 0% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).

This is a tight, recently built community near the western resort corridor of Osceola County, and with none of the homes carrying a homestead exemption, it behaves like an investment and short-stay market rather than a primary-residence neighborhood.

Best for

  • Investors underwriting a short-term or rental hold near the resort corridor
  • Second-home buyers who want recent construction and are not in a hurry
  • Patient buyers ready to wait for the right condition at or below the per-square-foot median

Probably not for

  • Buyers who need to close quickly in a market with a 75-day median
  • Sellers unwilling to price to a market that has softened 2.9% year over year
  • Buyers seeking a primary-residence, owner-occupied setting rather than an investment-driven one

If we were buying in Windsor At Westside Ph 3A 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 At Westside Ph 3A.

Best Buy
Buyers targeting a recently built, investment- or second-home-oriented property near the western Osceola corridor.
Biggest Risk
A slow, thin market with prices off 2.9% year over year rewards patience and punishes overpricing.
Sweet Spot
A well-kept home priced at or just below the $186.6 per square foot anchor.
Avoid If
You need a fast sale or a primary-residence owner-occupant setting.

A non-homestead market that trades on condition

With a zero homestead share, expect the buying and selling here to run on rental and second-home math. That changes the diligence: financing, insurance, HOA rules on short-term use, and realistic occupancy all matter more than curb appeal, and they influence what a given home is worth to the next buyer. The homes themselves are close in vintage and layout, so the spread you see in outcomes comes from upkeep, upgrades, and how a property is positioned for its use.

The pace is deliberate. Nine closings in the window against roughly 100 homes and a 75-day median means this is a thin, unhurried market where a mispriced listing sits. That works for a prepared buyer willing to wait for the right unit, and it demands discipline from a seller who wants a clean exit rather than a long carry.

The location and the amenities are priced into every listing in Windsor At Westside Ph 3A. The deal is won or lost on condition, the comps, and the renovation math.

Jon Brooks · Founder, Momentum Realty
4.0C- · Buy Score
Recent Direction5.3/10
Owner Commitment0.0/10
Pricing Power6.7/10

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 (4.0). Basis: Recent Direction -2.9% year-over-year; Owner Commitment 0% owner-occupied; Pricing Power 95.0% sale-to-list. Refreshed with each data update.

Why work with Momentum here

In a thin, non-homestead market like this, the median tells you where to start, not what a specific home is worth. We read each property on condition, finish, and its viability as an investment or second home, then price and negotiate against a real 75-day clock and a market that has softened 2.9% over the year. That is the difference between a clean sale and a listing that lingers.

Windsor At Westside Ph 3A in 15 seconds.

Best forBuyers targeting a recently built, investment- or second-home-oriented property near the western Osceola corridor.
Biggest advantageUniform 2019–2020 construction and consistent size make the median a usable starting benchmark.
Biggest riskA slow, thin market with prices off 2.9% year over year rewards patience and punishes overpricing.
Sweet spotA well-kept home priced at or just below the $186.6 per square foot anchor.
Avoid ifYou need a fast sale or a primary-residence owner-occupant setting.

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 At Westside Ph 3A sales matched to your home.

What is your Windsor At Westside Ph 3A home worth?

Get a no-obligation home value based on real comparable sales in Windsor At Westside Ph 3A, 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 At Westside Ph 3A?
The median sale price in Windsor At Westside Ph 3A was $532K over the 12 months ending July 13, 2026 (9 closed sales, Stellar MLS).
How long do homes in Windsor At Westside Ph 3A take to sell?
Homes that closed in the 12 months ending July 13, 2026 took a median 75 days on market (9 sales, Stellar MLS).
How many homes are in Windsor At Westside Ph 3A?
The Florida DOR 2025 assessment roll shows 100 homes in Windsor At Westside Ph 3A (public records).
What share of Windsor At Westside Ph 3A is owner-occupied?
0% of Windsor At Westside Ph 3A parcels carry a homestead exemption on the 2025 Florida DOR roll, the owner-occupancy proxy in public records.
When were the homes in Windsor At Westside Ph 3A built?
Homes in Windsor At Westside Ph 3A were built between 2019 and 2020, with a median year built of 2020.0 (FL DOR 2025 roll).
Do cash buyers compete in Windsor At Westside Ph 3A?
Cash buyers took 22% of Windsor At Westside Ph 3A sales in the 12 months ending June 2026 (2 of 9 closings, Stellar MLS).
Who is the best real estate agent for Windsor At Westside Ph 3A?
The best agent for Windsor At Westside Ph 3A 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 At Westside Ph 3A.
How do I find a top Kissimmee real estate agent who knows Windsor At Westside Ph 3A?
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 At Westside Ph 3A and the wider Kissimmee area.
Can Momentum Realty connect me with an agent for Windsor At Westside Ph 3A?
Yes. Use the form on this page and we'll introduce you to a local specialist who can guide your Windsor At Westside Ph 3A purchase or sale - no call center and no pressure.
Investors underwriting a short-term or rental hold near the resort corridorExcellent fit
Second-home buyers who want recent construction and are not in a hurryExcellent fit
Patient buyers ready to wait for the right condition at or below the per-square-foot medianExcellent fit
Buyers who need to close quickly in a market with a 75-day medianProbably not
Sellers unwilling to price to a market that has softened 2.9% year over yearProbably not
Buyers seeking a primary-residence, owner-occupied setting rather than an investment-driven oneProbably 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 2024 (12 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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