1638 WINDSOR OAK COURT KISSIMMEE FL 34744 MLS #S5133782

1638 WINDSOR OAK COURT
KISSIMMEE, FL, 34744
$265,000
3 Beds
2.5 Baths
1,380 SqFt
0.02 Acres
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MLS #S5133782 image #0
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.

Property Details

Price:
$265,000
MLS #:
S5133782
Status:
Active
Beds:
3
Baths:
2.5
Type:
Townhouse
Subdivision:
WINDSOR OAKS
Neighborhood:
34744kissimmee
Listed Date:
Sep 5, 2025
Finished Sq Ft:
1,380
Total Sq Ft:
1,490
Lot Size:
871 sqft / 0.02 acres (approx)
Year Built:
1999
ContemporaryPoolCommunity Gated34744 – Kissimmee34744kissimmeeWindsor OaksPlease Contact The Home Owners Association For Additional Lease Restrictions1-7 DaysPets Allowed

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Interior

Appliances
Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Ceramic Tile, Laminate
Heating
Electric
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Window Treatments
Laundry Features
In Kitchen, Inside, Laundry Closet
Levels
Two

Exterior

Architectural Style
Contemporary
Community Features
Deed Restrictions, Gated Community – No Guard, Pool, Sidewalks
Construction Materials
Block, Stucco
Direction Faces
North
Exterior Features
Lighting, Rain Gutters, Sidewalk, Sliding Doors
Lot Features
Private, Sidewalk
Patio And Porch Features
Covered, Enclosed, Porch, Rear Porch, Screened
Roof
Shingle
Security Features
Fire Sprinkler System, Gated Community, Smoke Detector(s)
Window Features
Blinds

Financial

HOA Fee
$180
HOA Fee Frequency
Monthly
HOA Includes
Community Pool, Pool Maintenance, Private Road
HOA Name
Leslie Ludlam / AMG of Central Florida
HOA Phone
407-847-9950
Tax Year
2024
Taxes
$2,008

Map

Community

Subdivisions in KISSIMMEE

Market Summary

Current real estate data for Townhouse in KISSIMMEE as of Apr 23, 2026
814
Townhouse Listed
158
Avg DOM
217
Avg $ / SqFt
$368,962
Avg List Price

Property Summary

    Located in the WINDSOR OAKS subdivision, 1638 WINDSOR OAK COURT KISSIMMEE FL is a Townhouse for sale in KISSIMMEE, FL, 34744. It is listed for $265,000 and features 3 beds, 3 baths, and has approximately 1,380 square feet of living space, and was originally constructed in 1999. The current price per square foot is $192. The average price per square foot for Townhouse listings in KISSIMMEE is $217. The average listing price for Townhouse in KISSIMMEE is $368,962. To schedule a showing of MLS#s5133782 at 1638 WINDSOR OAK COURT in KISSIMMEE, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

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