Windsor Oaks
Homes for Sale in Kissimmee, FL
All 2,887 homes for sale in KISSIMMEE, FL · median $374,999 · 721 townhomes for sale in KISSIMMEE · 328 homes for sale in 34744 · Osceola County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, Windsor Oaks in Kissimmee, FL has 2 homes for sale. Over the 12 months ending 2026-09-20, 3 recorded sales closed at a median of $250,500, $188 per square foot, a median 7 days on market, sellers accepting 96% of original asking. At the median price and Osceola County's FY2025-26 rate of 15.23 mills, annual property tax runs about $3,820 ($3,210 with the full homestead exemption).
Windsor Oaks right now
🟢 Buyer-leaning market. 12.0 months of supply and 33% of the inventory already under contract give buyers above-average negotiating leverage.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 September 12, 2026. Confidence: Low (3 active and pending listings, 0 closed sales in 12 months).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 5, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
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
Photos from Stellar MLS listings in Windsor Oaks; content deemed reliable but not guaranteed.
The market around Windsor Oaks
Windsor Oaks is too small for its own price trend, so here is the market around it.
In ZIP 34744, 418 homes are on the market and 21% are under contract — a steady corner of Kissimmee.
Across Osceola County, 4,423 homes are active and 1,079 pending (20% under contract).
ZIP and county figures describe the wider market, not Windsor Oaks specifically. Momentum Research analysis of MLS records.
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 2026-09-12, 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.
Every Home for Sale in Windsor Oaks Kissimmee Right Now (2)
All 2 active and pending Windsor Oaks Kissimmee listings with a detail page, newest first, refreshed twice a day from the MLS.
- 1661 Windsor Oak Court · $245,000 · 3 bd / 2.5 ba · pending · listed Sep 9, 2026 · listed by Better Homes And Gardens Real Estate Mann Global P
- 1647 Windsor Oak Court · $245,000 · 3 bd / 2.5 ba · listed by Advisers Realty & Management
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.
Shop the zone: Homes zoned for Gateway High School (9 12)
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.
Use your leverage. With inventory sitting, there is room to negotiate on anything dated or overpriced and to ask for repairs or a rate buydown.
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
Inventory runs at 12.0 months of supply, a buyer-leaning market.
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.
HOA, CDD & Fees
- HOA dues reported around $180/month (about $2,160/yr) · median of 27 MLS listings, most billed monthly
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $180 per month ($2,160 a year) - the median AssociationFee across 27 MLS records, normalised to a monthly figure; most are billed monthly. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
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 all homes for sale in Kissimmee →
Recently off market in Windsor Oaks
Homes in Windsor Oaks that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 3 on record.
- 1638 Windsor Oak Court · off market
- 1647 Windsor Oak Court · off market
- 1661 Windsor Oak Court · off market
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Osceola County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Osceola County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
18% of homes for sale in ZIP 34744 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 (2026-10-01).
WINDSOR OAKS Market Scorecard
WINDSOR OAKS is currently a buyer's market. About 8.0 months of supply, a median asking price of $245,000, and homes go under contract in about 152 days.
Go deeper: county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Frequently Asked Questions
Is Windsor Oaks a buyer's or seller's market right now?
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?
Where is Windsor Oaks, and what county is it in?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| 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 local comps.
Looking to buy here? Search homes for sale →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Windsor Oaks fits the bigger picture — live prices, inventory, and Momentum Scores:
More Kissimmee & Kissimmee, St. Cloud & Osceola County guides
Compare before you commit - every guide covers pricing, HOA/CDD, insurance posture, and fit. Browse all of Kissimmee, St. Cloud & Osceola County or the full Neighborhood Finder.
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