Windsor/Westside Ph 1
Homes for Sale in Kissimmee, FL
True comps, carrying-cost math, and listings before the portals.
Price here is driven far more by the home than by the ground under it. These are large builds — a median of roughly 3,433 square feet on homes dated 2015 to 2020 — and at a median of $400,000, or about $176.6 per square foot, you are buying scale and recent construction. Condition, finish level, and how a given home is furnished or configured will move the number well off that median in both directions, so treat $400,000 as a center of gravity, not a fixed rate.
The market posture is slow and deliberate. Median days on market sits at 155, which tells you buyers are taking their time and sellers who price to the current market — not to what they hoped a year ago — are the ones getting to the closing table. A homestead share near 1% signals this is dominated by non-primary-residence use, so both sides should underwrite this as an investment/second-home market where carrying costs and rental performance, not owner-occupant urgency, set the pace.
The 60-Second Overview
Windsor/Westside Ph 1 market snapshot (as of July 13, 2026): the median sale price is about $400K ($177 per sq ft over the trailing 12 months of closed sales), and a median 155 days on market for closed sales.
Windsor/Westside Ph 1 is a community of 262 homes in Kissimmee, Osceola County, built between 2015 and 2020 (median 2016.0), with a median living area of about 3,433 square feet. 1% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Windsor/Westside Ph 1 is a 262-home, recently built community in Kissimmee, Osceola County, weighted toward large floor plans and non-primary-residence ownership. The long time-on-market and near-zero homestead share make this a market to enter with patience and a clear numbers-first plan.
Who Windsor/Westside Ph 1 is best for.
Best for
- Investors underwriting a rental or second-home purchase who value large square footage and recent construction
- Buyers with the patience to negotiate in a 155-day market and the budget to carry a substantial home
- Buyers who want a 2015-to-2020 build at scale and will price against condition, not a headline median
Probably not for
- Buyers who need to close quickly in a fast-moving market
- Buyers seeking a smaller or lower-carry footprint
- Buyers who want a primary-residence, owner-occupied setting given the near-zero homestead share
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 ($400K) IS the median in the snapshot above.
Windows contain 0 to 38 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 1 buying strategy.
If we were buying in Windsor/Westside Ph 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 1.
A large-format, investment-led market
The defining feature is size paired with recency: a median living area of about 3,433 square feet across a build window of 2015 to 2020, with a median build year of 2016. You are not shopping for a starter footprint here — the inventory skews to substantial homes, and the per-square-foot median of $176.6 reflects that scale. Because the community is small at 262 homes and closings over the trailing three-month window were limited, individual listings can swing the read, so lean on the median rather than any single comp.
The 155-day median on market is the number that should shape strategy. That pace rewards sellers who prepare, price, and stage correctly, and it gives buyers real room to negotiate and inspect without pressure. With a homestead share of roughly 1%, the practical framing is a rental-and-second-home market: the analysis that matters is occupancy potential, HOA and short-term-rental rules, and total carry — not comparisons to owner-occupied neighborhoods across the region.
The location and the amenities are priced into every listing in Windsor/Westside Ph 1. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a thin, slow-moving market like this one, the median can hide as much as it reveals. We price and negotiate off the actual condition and configuration of each home rather than a headline figure, and we tell you plainly when a listing is stale, overpriced against the 155-day reality, or better suited to a different buyer's plan. On a large-format, investment-led community, that discipline is the difference between a clean close and months of carry.
Windsor/Westside Ph 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 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 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 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 1 home worth?
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Frequently Asked Questions
What is the median home price in Windsor/Westside Ph 1?
How long do homes in Windsor/Westside Ph 1 take to sell?
How many homes are in Windsor/Westside Ph 1?
What share of Windsor/Westside Ph 1 is owner-occupied?
When were the homes in Windsor/Westside Ph 1 built?
Do cash buyers compete in Windsor/Westside Ph 1?
Who is the best real estate agent for Windsor/Westside Ph 1?
How do I find a top Kissimmee real estate agent who knows Windsor/Westside Ph 1?
Can Momentum Realty connect me with an agent for Windsor/Westside Ph 1?
Should you buy in Windsor/Westside Ph 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 13, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (street-list match (8 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-07-12 |
| Historical depth | Closed-sale records back to 2016 (68 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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