Windsor/Westside-Ph 2B-1
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
What sets price here is scale and newness. This is a compact community of 69 homes built in 2018 and 2019, with a median size north of 4,300 square feet. At a median of $590,000 and roughly $146 per square foot, you are paying for large, recently built floor plans rather than location premium. The per-square-foot figure is modest for the price point, which tells you the square footage is doing the heavy lifting.
Market posture is fast. A median of 3 days on market against 3 recent closings signals thin inventory and quick decisions. Sellers hold the leverage on timing; buyers should come pre-approved and ready to move rather than expecting a long negotiation. Note the homestead share sits at zero, which is consistent with a market oriented toward second homes and short-term use rather than primary occupancy.
The 60-Second Overview
Windsor/Westside-Ph 2B-1 market snapshot (as of July 15, 2026): the median sale price is about $590K ($146 per sq ft over the trailing 12 months of closed sales), and a median 3 days on market for closed sales.
Windsor/Westside-Ph 2B-1 is a community of 69 homes in Kissimmee, Osceola County, built between 2018 and 2019 (median 2019), with a median living area of about 4,353 square feet. 0% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Windsor/Westside-Ph 2B-1 in Kissimmee is a small, all-new-construction pocket of oversized homes. With no homestead presence, it reads as an investment- and vacation-oriented enclave rather than an owner-occupied subdivision.
Who Windsor/Westside-Ph 2B-1 is best for.
Best for
- Investors targeting large, newer homes for short-term-rental income
- Second-home buyers wanting a sizable vacation property in the Westside corridor
- Buyers who can act quickly and arrive pre-approved in a fast-moving segment
Probably not for
- Buyers seeking a small or modest-square-footage home
- Anyone wanting an established owner-occupied, homesteaded neighborhood
- Buyers who need a long, unhurried negotiation window
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending July 15 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($590K) IS the median in the snapshot above.
Windows contain 0 to 6 sales each (3 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/Westside-Ph 2B-1 buying strategy.
If we were buying in Windsor/Westside-Ph 2B-1 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/Westside-Ph 2B-1.
Big new homes, thin supply
The defining traits are size and vintage. Every home dates to 2018 or 2019, and the median living area exceeds 4,300 square feet. That is a lot of house, and it explains why the median sits at $590,000 while the price per square foot stays around $146. You are buying volume, not a premium address.
With only 69 homes and a median of just 3 days on market, this is a small, quick-moving segment. Prices will vary by condition, furnishings, and rental setup rather than by any broad range we can quote. A zero homestead share underlines that this is not a primary-residence community; it functions as short-term-rental and vacation product in Osceola County's Westside corridor.
The location and the amenities are priced into every listing in Windsor/Westside-Ph 2B-1. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a 69-home community turning over in a median of 3 days, timing and preparation decide who wins. We track this specific pocket, know how the large 2018–2019 floor plans differ, and will tell you plainly when a listing is priced for its condition or reaching past it. On the sell side, we position oversized, rental-oriented product for the buyers actually shopping it.
Windsor/Westside-Ph 2B-1 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/Westside-Ph 2B-1 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/Westside-Ph 2B-1 sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor/Westside-Ph 2B-1, 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/Westside-Ph 2B-1 home worth?
Get a no-obligation home value based on real comparable sales in Windsor/Westside-Ph 2B-1, 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/Westside-Ph 2B-1?
How long do homes in Windsor/Westside-Ph 2B-1 take to sell?
How many homes are in Windsor/Westside-Ph 2B-1?
What share of Windsor/Westside-Ph 2B-1 is owner-occupied?
When were the homes in Windsor/Westside-Ph 2B-1 built?
Do cash buyers compete in Windsor/Westside-Ph 2B-1?
Who is the best real estate agent for Windsor/Westside-Ph 2B-1?
How do I find a top Kissimmee real estate agent who knows Windsor/Westside-Ph 2B-1?
Can Momentum Realty connect me with an agent for Windsor/Westside-Ph 2B-1?
Should you buy in Windsor/Westside-Ph 2B-1?
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 15, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (2 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2021 (11 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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