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1638 WINDSOR OAK CT

1638 Windsor Oak CourtKissimmee, FL, 34744

3beds
3baths
1,380sqft
Townhouse
Built in 1999
$180 Monthly HOA Fee
$245,000
Sold
Price per sqft
$178
Sold on
Sep 15, 2026
MLS #S5153418Updated Sep 15, 2026

About this property

Whether you live here year-round or use it as your Florida escape, this property offers the best of both worlds, personal enjoyment and rental income potential when you’re away. Welcome to this beautifully maintained and fully upgraded townhome in the heart of Kissimmee, located in the quiet, gated community of Windsor Oaks. This spacious 3-bedroom, 2.5-bath home features a flexible layout with two master suites upstairs and a third bedroom on the main level that can also serve as a home office, den, or gym. Major improvements give this home incredible value and peace of mind: the roof was replaced just 8 months ago, the A/C is only 2 years old, the water heater is brand new, the sliding glass door recently installed new, and all appliances including washer and dryer are included.You’ll find a bright and inviting open-concept living and dining area that flows seamlessly into the kitchen. The kitchen has been fully upgraded with new cabinets, modern fixtures, a farmhouse sink, quartz countertops with a beautiful backsplash, and a new garbage disposal. All bathrooms feature new cabinetry and fixtures, while the upstairs and bedrooms are finished with new laminate flooring. Windsor Oaks provides a low HOA, short-term rental approval, and a community pool, making this property ideal for investors and first-time homeowners alike. With shops, restaurants, and entertainment nearby, this home blends modern upgrades with everyday convenience.

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Property details

Property type
Townhouse
Street address
1638 Windsor Oak Court
City
Kissimmee
State
FL
ZIP code
34744
Year built
1999
New construction
No
Faces
North
Rooms
10
Building stories
2
Living area
1,380 sqft
Total building area
1,490 sqft
Architectural style
Contemporary
Levels
Two

Stellar MLSThe data relating to real estate displayed on this website comes in part from the Internet Data Exchange (IDX) Program of Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; the availability of any listing should always be independently verified. Listing information is provided for consumers' personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.Stellar (MFR) data last updated at October 8, 2026 at 4:01 AM EDT

Price & sale history

EventPrice
SoldMLS #S5153418$245,000
Listed for saleMLS #S5153418$245,000
SoldMLS #S4724823$76,000
Price reducedMLS #S4724823$79,000Change: −18.6%−$18,000
History may be incomplete.
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Location

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1638 WINDSOR OAK CT
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