$265,000

1638 Windsor Oak Court, Kissimmee, FL 34744

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$265,000

(19,900) 02/11/2026

1638 Windsor Oak Court Kissimmee, FL 34744

For Sale MLS# S5133782

3 beds 3 baths 1,380 sq ft Townhouse/Twinhome

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Data current as of 03/03/2026 21:54:11

Details for 1638 Windsor Oak Court

MLS# S5133782

Description for 1638 Windsor Oak Court, Kissimmee, FL, 34744


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.

Listing Information


Property Type: Residential, Townhouse

Status: Active

Bedrooms: 3

Bathrooms: 3

Lot Size: 0.02 Acres

Square Feet: 1,380 sq ft

Year Built: 1999

Stories: 2 Story

Construction: Block,Stucco

Subdivision: Windsor Oaks

Foundation: Slab

County: Osceola

Room Information


Main Floor

Bathroom 3:

Living Room: 14x15

Porch:

Bedroom 2: 10x9

Dining Room:

Kitchen: 10x9

Upper Floor

Bathroom 2:

Bedroom 3: 14x14

Primary Bathroom:

Primary Bedroom: 14x14

Bathrooms

Full Baths: 2

1/2 Baths: 1

Additonal Room Information

Laundry: Laundry Closet, In Kitchen, Inside

Interior Features


Appliances: Electric Water Heater, Washer, Range, Refrigerator, Dishwasher, Disposal, Dryer, Microwave

Flooring: Ceramic Tile,Laminate

Doors/Windows: Blinds, Window Treatments

Additional Interior Features: Ceiling Fan(s), Living/Dining Room, Window Treatments, Walk-In Closet(s), Built-in Features, Open Floorplan, Upper Level Primary, Kitchen/Family Room Combo, Solid Surface Counters, Wood Cabinets

Utilities


Water: Public

Sewer: Public Sewer

Other Utilities: Cable Available,Electricity Available,Municipal Utilities,Sewer Connected,Water Available

Cooling: Ceiling Fan(s), Central Air

Heating: Electric

Exterior / Lot Features


Roof: Shingle

Pool: Community

Additional Exterior/Lot Features: Rain Gutters, Lighting, Enclosed, Screened, Covered, Porch, Rear Porch, Private, Landscaped, Private Road

Community Features


Community Features: Street Lights, Gated, Pool, Sidewalks

Security Features: Fire Sprinkler System, Gated Community, Smoke Detector(s)

HOA Dues Include: Road Maintenance, Pool(s)

Homeowners Association: Yes

HOA Dues: $180 / Monthly

Driving Directions


From John Young Pkwy, W Carroll St, Michigan Ave and Mill Slough Rd to Windsor Oak Ct in Kissimmee

Financial Considerations


Terms: Cash,Conventional,FHA,VA Loan

Tax/Property ID: 14-25-29-2365-0001-0120

Tax Amount: 2008.32

Tax Year: 2024

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Interest rate and annual percentage rate (APR) are based on current market conditions, are for informational purposes only, are subject to change without notice and may be subject to pricing add-ons related to property type, loan amount, loan-to-value, credit score and other variables. Estimated closing costs used in the APR calculation are assumed to be paid by the borrower at closing. If the closing costs are financed, the loan, APR and payment amounts will be higher. If the down payment is less than 20%, mortgage insurance may be required and could increase the monthly payment and APR. Contact us for details. Additional loan programs may be available. Accuracy is not guaranteed, and all products may not be available in all borrower's geographical areas and are based on their individual situation. This is not a credit decision or a commitment to lend.

Sales History

Date Price
Currently not available.

Tax Summary

Tax Year Estimated Market Value Total Tax
Currently not available.

Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.

Schools nearby 1638 Windsor Oak Court

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Schools nearby Grades Distance Rating
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.

The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.

SchoolDigger ® Rating

The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.

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