Windsor At Westside Ph 2A
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Price here is driven by scale and finish, not lot premiums. These are large homes built within a tight window, and the median living area sits well above what most Kissimmee communities offer. At a median of $550,000 and roughly $171 per square foot, you are paying for square footage first; condition and furnishing package explain most of the spread from there.
The current posture favors patient buyers. Median days on market sit at 73, and prices are down 16% year over year, so sellers who need a quick exit should expect to negotiate. The very low homestead share tells you this is a rental- and second-home-heavy pocket, which means pricing tracks the short-term-stay market as much as it tracks resale comps. Buyers should underwrite carrying costs carefully; sellers should price to the current window, not to last year.
Windsor At Westside Ph 2A right now
🔴 Off the recent peak. The trailing-12-month median ($550K) is down 16.0% from the prior 12 months ($655K). 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: Medium (12 and 9 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 At Westside Ph 2A right now
🔴 Off the recent peak. The trailing-12-month median ($550K) is down 16.0% from the prior 12 months ($655K). 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: Medium (12 and 9 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 2A market snapshot (as of July 13, 2026): the median sale price is about $550K ($171 per sq ft over the trailing 12 months of closed sales), and a median 73 days on market for closed sales. The trailing-12-month median is down 16% from the prior 12 months, computed from record-level Stellar MLS closed sales (12 closings in the current window).
Windsor At Westside Ph 2A is a community of 152 homes in Kissimmee, Osceola County, built between 2016 and 2019 (median 2018), with a median living area of about 4,353 square feet. 1% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Windsor At Westside Ph 2A is a compact enclave of 152 homes in western Osceola County, built out over a short 2016 to 2019 stretch, so the housing stock is consistent in age and scale. The near-total absence of homestead status signals a community oriented around rental and vacation use rather than primary residence.
Who Windsor At Westside Ph 2A is best for.
Best for
- Investors underwriting a short-term-rental with the carrying costs and days-on-market baked in
- Buyers wanting maximum square footage in newer construction near the western Osceola attractions corridor
- Cash or well-qualified buyers who can afford to wait out a 73-day median rather than overpay for speed
Probably not for
- Buyers seeking an owner-occupied, homestead-heavy primary-residence community
- Anyone needing to sell quickly, given the soft year-over-year pricing and longer market times
- Budget-focused buyers looking for a smaller, lower-priced home than the large floor plans here support
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 ($550K) IS the median in the snapshot above, and the move from 2025 ($655K) IS the -16.0% one-year change.
Windows contain 0 to 12 sales each (12 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 At Westside Ph 2A buying strategy.
If we were buying in Windsor At Westside Ph 2A 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 At Westside Ph 2A.
Big homes, rental-driven pricing
The defining feature here is size. A median living area of 4,353 square feet with a median year built of 2018 means you are buying substantial, relatively new construction under one consistent design era. That scale is what supports the $550,000 median; the per-square-foot figure of roughly $171 is modest, which is typical when large floor plans carry the price.
With a homestead share near zero, this is functionally a short-term-rental and second-home market. That has two consequences for pricing: values move with travel demand and nightly-rate performance, and the 16% year-over-year decline should be read in that context rather than as a general Kissimmee housing signal. The 73-day median on market reflects a buyer pool that is doing investment math, not just choosing a place to live.
The location and the amenities are priced into every listing in Windsor At Westside Ph 2A. 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 At Westside Ph 2A 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 (3.5). Basis: Recent Direction -16.0% year-over-year; Owner Commitment 1% owner-occupied; Pricing Power 97.4% sale-to-list. Refreshed with each data update.
Why work with Momentum here
A rental-oriented community demands a different diligence checklist than a primary-residence neighborhood: HOA short-term-stay rules, furnishing packages, and how a listing's income history is being presented all shape what a home is actually worth. We help buyers separate the real estate from the rental pitch, and we help sellers price to the current 73-day, down-16% window instead of anchoring to a stronger past market.
Windsor At Westside Ph 2A 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 At Westside Ph 2A 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 At Westside Ph 2A sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor At Westside Ph 2A, 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 At Westside Ph 2A home worth?
Get a no-obligation home value based on real comparable sales in Windsor At Westside Ph 2A, 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 At Westside Ph 2A?
How long do homes in Windsor At Westside Ph 2A take to sell?
How many homes are in Windsor At Westside Ph 2A?
What share of Windsor At Westside Ph 2A is owner-occupied?
When were the homes in Windsor At Westside Ph 2A built?
Do cash buyers compete in Windsor At Westside Ph 2A?
Who is the best real estate agent for Windsor At Westside Ph 2A?
How do I find a top Kissimmee real estate agent who knows Windsor At Westside Ph 2A?
Can Momentum Realty connect me with an agent for Windsor At Westside Ph 2A?
Should you buy in Windsor At Westside Ph 2A?
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 (4 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2021 (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.
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 ($550K) IS the median in the snapshot above, and the move from 2025 ($655K) IS the -16.0% one-year change.
Windows contain 0 to 12 sales each (12 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 (4 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2021 (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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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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