Windsor/Westside
Homes for Sale in Kissimmee, FL
All 2,944 homes for sale in KISSIMMEE, FL · median $373,250 · 845 homes for sale in 34747 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
Market Heat
Over the 12 months ending 2026-08-02, 8 recorded sales closed at a median of $472,500, $177 per square foot, a median 297 days on market, sellers accepting 84% of original asking (-26% versus the prior year). At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $7,200 ($6,600 with the full homestead exemption).
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.
Windsor/Westside right now
🔴 Off the recent peak. The trailing-12-month median ($472K) is down 26.2% from the prior 12 months ($640K). With about 23 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 August 2. Confidence: Medium (8 and 21 sales in the two windows).
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· Updated October 1, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
Nearby homes for sale
No active listings inside WINDSOR/WESTSIDE PH 1 right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Windsor/Westside market snapshot (as of August 2, 2026): the median sale price is about $472K ($177 per sq ft over the trailing 12 months of closed sales), and a median 298 days on market for closed sales. The trailing-12-month median is down 26% from the prior 12 months, computed from record-level Stellar MLS closed sales (8 closings in the current window).
In ZIP 34747 (KISSIMMEE), 2,599 homes closed in the last 12 months at a median of $460K ($220/sq ft), down 3.8% year over year, with a median 75 days on market. Right now 581 active and 101 pending listings put supply at about 7.3 months — a buyer's market. See the live ZIP 34747 housing market and the Osceola County market.
Windsor/Westside is a community of 804 homes in Kissimmee, Osceola County, built between 2015 and 2020 (median 2018), 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 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 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 August 2 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($472K) IS the median in the snapshot above, and the move from 2025 ($640K) IS the -26.2% one-year change.
Windows contain 0 to 120 sales each (8 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 2016 through 2026. Deemed reliable but not guaranteed.
12% of homes for sale in ZIP 34747 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-08-01).
The Windsor/Westside buying strategy.
If we were buying in Windsor/Westside 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.
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. 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/Westside 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 (0.0). Basis: Recent Direction -26.2% year-over-year; Owner Commitment 1% owner-occupied; Pricing Power 83.9% sale-to-list. Refreshed with each data update.
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 in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- 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 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 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, 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 home worth?
Get a no-obligation home value based on real comparable sales in Windsor/Westside, 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?
How long do homes in Windsor/Westside take to sell?
How many homes are in Windsor/Westside?
What share of Windsor/Westside is owner-occupied?
When were the homes in Windsor/Westside built?
Do cash buyers compete in Windsor/Westside?
Who is the best real estate agent for Windsor/Westside?
How do I find a top Kissimmee real estate agent who knows Windsor/Westside?
Can Momentum Realty connect me with an agent for Windsor/Westside?
Where is Windsor/Westside, and what county is it in?
Is Windsor/Westside a good place to live?
Should you buy in Windsor/Westside?
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 August 2, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (23 streets, ZIP 34747)) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2016 (229 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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See how WINDSOR/WESTSIDE PH 1 fits the bigger picture — live prices, inventory, and Momentum Scores:
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