1638 WINDSOR OAK COURT Kissimmee, FL $ 284,900
1638 WINDSOR OAK COURT
$ 284,900
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1638 WINDSOR OAK COURT

Kissimmee, FL, 34744
$ 284,900
Bedrooms3 Baths2.1 Sq 1,380

Monthly Estimate*

$ 1,777

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Townhouse for sale in Kissimmee, FL

for $284,900 with 3 bedrooms and 2 full baths, 1 half bath. This 1,380 square foot townhouse was built in 1999 on a lot size of 0.02.

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. 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. 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. 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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Townhouse Active

Price

$ 284,900

Bedrooms

3

Full Bath

2

Half Bath

1

Property Type

Townhouse

Taxes

$ 2,008

Style

Contemporary

Lot Size

0.02

Year Built

1999

Town/City

Kissimmee

County/Region

Osceola

MLS | Web ID

S5133782

Features
General
Sewer Public Sewer
Heating Electric
Cooling Central Air
Utilities Cable Available Electricity Available Public Sewer Connected Street Lights Water Available
Possession Close Of Escrow
Roof Shingle
Appliances Dishwasher Disposal Dryer Electric Water Heater Microwave Range Refrigerator Washer
Zoning KSRP
HOA Fee 180
Association Fee Includes Community Pool Pool Maintenance Private Road
Patio/Porch Features Covered Enclosed Porch Rear Porch Screened
Architectural Style Contemporary
Security Features Fire Sprinkler System Gated Community Smoke Detector(s)
Construction Materials Block Stucco
Pets Allowed Yes
Year Built 1999
Levels Two
Property Subtype Townhouse
Tax Year 2024
Ownership Fee Simple
Community Features Deed Restrictions Gated Community - No Guard Pool Sidewalks
Assoc Fee Paid Per Monthly
County Osceola
New Construction false
Property Type Residential
Subdivision Name WINDSOR OAKS
Facing Direction North
Garage Y/N false
Total Rooms 10
Full Baths 2
Status Active
Directions From John Young Pkwy W Carroll St Michigan Ave and Mill Slough Rd to Windsor Oak Ct in Kissimmee
City KISSIMMEE
Association Name Leslie Ludlam / AMG of Central Florida
Senior Community Y/N false
MLS Area 34744 - Kissimmee
Lot Size Units Square Feet
Lot Size Square Feet 871
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Land Lease Y/N false
Tax Annual Amount 2008.32
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/S5133782
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 12
Legal Description WINDSOR OAKS PB 8 PB 42 LOT 12
Minimum Lease 1-7 Days
Water Access Y/N false
Monthly HOA Amount 180
Additional Rooms Inside Utility
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities 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
Flooring Ceramic Tile Laminate
Furnished Y/N Unfurnished
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds
Fireplace Y/N false
Half Baths 1
Laundry Features In Kitchen Inside Laundry Closet
Total Bedrooms 3
Total Baths 3
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Exterior
Exterior Amenities Lighting Rain Gutters Sidewalk Sliding Doors
Vegetation Trees/Landscaped
Lot Features Private Sidewalk
Water Source Public
Lot Size Area 871
Foundation Details Slab
Building Area Total 1490
Lot Size Acres 0.02
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
Road Frontage Type Street Paved Private Road
Road Responsibility Private Maintained Road
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* Excluded Features
List By
Preferred Real Estate Brokers

Broker

getsetwithlissette04@gmail.com

Email

Affordability Calculator

$1,945
Per Month
91%
9%
0%
Monthly Principal & Interest
$1,777
Monthly Property Taxes
$167
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$284,900 Listed Price

Map


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1638 WINDSOR OAK COURT, Kissimmee, FL, 34744 is a Townhouse for sale at $284,900 with 1,380 sqft and a lot size of 0.02. 1638 WINDSOR OAK COURT has 3 bedrooms, 2.1 baths, and was built in 1999. The property's zip code is 34744 which is in Kissimmee, FL