Windsor Pines
Homes for Sale in Kissimmee, FL
All 2,944 homes for sale in Kissimmee, FL · median $373,250 · 253 homes for sale in 34741 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, the MLS records 4 closed sales in Windsor Pines 02 in Kissimmee, FL since 2016, the most recent in March 2018. Across Kissimmee as a whole, 2,523 homes closed in the last 12 months at a median of $387,990, 62 median days on market, with 1,265 homes for sale today. At that median and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $5,910 ($5,310 with the full homestead exemption).
The honest starting point here is that current MLS activity gives us very little to work with. There are no recent closings in our tracked window and no community amenities identified from active listings, so we cannot responsibly cite a price trend, a typical days-on-market figure, or an inventory count for Windsor Pines 02 right now.
That thin data does not mean nothing is happening on the ground, only that it is not showing up in the feed we monitor. For a buyer or seller, that means going in with eyes open: pricing and timing decisions here should lean on a direct comparison to nearby Kissimmee and Osceola County activity rather than on this community's own recent numbers, until more transactions post.
Nearby homes for sale
No active listings inside Windsor PinesHomes for Sale in Kissimmee, FL 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 Pines 02 sits in Kissimmee, Osceola County, but current MLS data does not show enough recent closing activity or listed amenities to characterize the community's present market rhythm with any precision.
Stellar MLS sales records identify 37 homes in Windsor Pines that have changed hands since 2004, built between 1982 and 1984 (median 1982), with a median living area of about 1,290 sq ft and a typical 2-bedroom, 2-bath layout; 86% are condominiums. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Windsor Pines is best for.
Best for
- A buyer willing to do extra legwork, including a direct walk-through and independent comp pulls, before committing
- Someone already targeting Kissimmee or Osceola County broadly and open to this specific community as one option among several
- A seller comfortable pricing off nearby area activity rather than this community's own recent closings
Probably not for
- A buyer who needs a documented recent price trend before making an offer
- Someone shopping specifically for a listed community amenity, since none are currently identified here
- A buyer on a tight timeline who cannot wait on manual verification of local details
The market around Windsor Pines
Windsor Pines is too small for its own price trend, so here is the market around it.
In ZIP 34741, 299 homes are on the market and 15% are under contract — a slower corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
In ZIP 34741 (Kissimmee), 754 homes closed in the last 12 months at a median of $411K ($205/sq ft), down 0.8% year over year, with a median 44 days on market. Right now 207 active and 46 pending listings put supply at about 6.1 months — a balanced market. See the live ZIP 34741 housing market and the Osceola County market.
ZIP and county figures describe the wider market, not Windsor Pines specifically. Momentum Research analysis of MLS records.
The Windsor Pines buying strategy.
If we were buying in Windsor Pines 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 Pines.
A Quiet Stretch in the Data
When a community shows zero closings in the tracked window, it usually means one of two things: very few homes have changed hands recently, or activity is happening through channels this feed does not capture in full. Either way, we are not going to manufacture a median price or a days-on-market figure that is not there. That is a discipline we hold to even when it makes for a shorter write-up.
The same goes for amenities. Nothing has been identified from current MLS listings for Windsor Pines 02, which is a statement about what is documented in active listing data, not a judgment on the property itself. Anyone considering this community should verify lot specifics, any association details, and nearby infrastructure directly, since the feed simply is not populated with that layer right now.
The location and the amenities are priced into every listing in Windsor Pines. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a data-light community like this, the value of a local broker goes up, not down. We will pull comparable activity from surrounding Kissimmee inventory, walk the property and area in person, and give you a grounded read instead of a generic one built on numbers that do not exist yet in the public feed.
Windsor Pines 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 Pines 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 Pines sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Windsor Pines, 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 Pines home worth?
Get a no-obligation home value based on real comparable sales in Windsor Pines, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Kissimmee →
Should you buy in Windsor Pines?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2016 (4 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.
Own a home here?
You just read the data. Now see what your home is worth.
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 local comps.
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See how Windsor Pines 02 fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Windsor Pines
Where is Windsor Pines?
Windsor Pines is a community in Kissimmee, Osceola County, Florida, ZIP 34741.
Are there homes for sale in Windsor Pines right now?
No active listings inside Windsor Pines at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Windsor Pines have an HOA or CDD?
No HOA is on record for Windsor Pines in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
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