WINDSOR OAKS
Homes for Sale in KISSIMMEE, FL
True comps, carrying-cost math, and listings before the portals.
WINDSOR OAKS right now
🟡 Balanced market. 4.0 months of supply and 50% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of August 2, 2026. Confidence: Low (2 active and pending listings, 3 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
Updated August 2, 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 OAKS market snapshot (as of August 2, 2026): the median sale price is about $264K ($198 per sq ft over the trailing 12 months of closed sales), a median 23 days on market for closed sales, and 4.0 months of supply, a balanced market.
WINDSOR OAKS is a community of 50 homes in KISSIMMEE, Osceola County, built between 1994 and 2000 (median 1999), with a median living area of about 1,412 square feet. 46% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of WINDSOR OAKS. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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WINDSOR OAKSPrice 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 ($264K) IS the median in the snapshot above.
Windows contain 0 to 3 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 2014 through 2025. Deemed reliable but not guaranteed.
WINDSOR OAKS Market Scorecard
WINDSOR OAKS is currently a balanced market. About 4.0 months of supply, a median asking price of $264,900, and homes go under contract in about 1 days.
Go deeper: county scorecard · true cost calculator · affordability calculator.
Live data: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Homes For Sale Right Now in WINDSOR OAKS
Live MLS inventory for WINDSOR OAKS. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending WINDSOR OAKS listings as of 2026-08-23, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2014 through 2025. Tap any home to ask about it.
WINDSOR OAKS on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
Life at WINDSOR OAKS
- Pool · reported on 5 of 5 listings
- Gated Community - No Guard · reported on 4 of 5 listings
- Community Mailbox · reported on 3 of 5 listings
- Deed Restrictions · reported on 2 of 5 listings
- Gated Community · reported on 2 of 5 listings
- No Truck/RV/Motorcycle Parking · reported on 1 of 5 listings
- Gated · reported on 1 of 5 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
Schools
- Osceola County Public Schools
- Verify the zoned schools by address
- Magnet and choice options may be available
- Mill Creek Elem (K 5) · Elementary
- Denn John Middle · Middle
- Gateway High School (9 12) · High
Zoned schools reflect the assignments reported on recent WINDSOR OAKS listings and can change; always confirm with Osceola County Public Schools for a specific address.
Buying with schools in mind? We can confirm the exact zoned schools for any WINDSOR OAKS address.
The WINDSOR OAKS buying strategy.
If we were buying in WINDSOR OAKS 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 OAKS.
A closer look at the WINDSOR OAKS market
At a median of $198 per square foot, WINDSOR OAKS prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 4.0 months of supply, a balanced market. Homes that do trade take a median 23 days on market, useful leverage on any listing that has lingered.
The housing stock is 50 homes built between 1994 and 2000, and 46% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in WINDSOR OAKS. 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 OAKS 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 (5.6). Basis: Liquidity & Demand 4.0 months of supply; Owner Commitment 46% owner-occupied; Pricing Power 94.3% sale-to-list. Refreshed with each data update.
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 OAKS 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 OAKS sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in WINDSOR OAKS, 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 OAKS home worth?
Get a no-obligation home value based on real comparable sales in WINDSOR OAKS, 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 homes for sale in WINDSOR OAKS on the map →
Frequently Asked Questions
What is the median home price in WINDSOR OAKS?
How long do homes in WINDSOR OAKS take to sell?
Is WINDSOR OAKS a buyer's or seller's market right now?
How many homes are in WINDSOR OAKS?
What share of WINDSOR OAKS is owner-occupied?
When were the homes in WINDSOR OAKS built?
Do cash buyers compete in WINDSOR OAKS?
Who is the best real estate agent for WINDSOR OAKS?
How do I find a top KISSIMMEE real estate agent who knows WINDSOR OAKS?
Can Momentum Realty connect me with an agent for WINDSOR OAKS?
Nearby Communities
Explore more neighborhoods near WINDSOR OAKS with Momentum Realty’s local guides.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: August 2, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending August 2, 2026 |
| Housing stock & ownership | Florida DOR 2025 assessment roll (community parcel extract) |
| Under-contract shares | Stellar MLS records, as of 2026-08-01 |
| Historical depth | Closed-sale records back to 2014 (12 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 your area comps.
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