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$284,900

  • For Sale
  • Active
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,380 Sq. Ft.
  • Updated 3 days ago
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Seller is motivated and open to reasonable offers on this upgraded 3-bedroom townhome.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.

Full Property Details for 1638 Windsor Oak Ct

General

  • Price: $284,900
  • HOA FEE: $180/month
  • Taxes: $2,008 (2024)
  • Status: Active
  • Type: Townhouse
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5133782
  • Updated: 1/15/2026
  • Added to Site: 135 day(s) ago

Rental Information

  • Min. Lease: 1-7 Days

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Fan(s), Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: In Kitchen, Inside, Laundry Closet

Additional Information

  • Security/Safety: Fire Sprinkler System, Gated Community, Smoke Detector(s)

Exterior

  • Exterior Features: Lighting, Rain Gutters, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Enclosed, Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Enclosed, Porch, Rear Porch, Screened

Location

  • Area: 34744 - Kissimmee
  • County: Osceola
  • Development Name: 34744 - Kissimmee
  • Subdivision: WINDSOR OAKS
  • Driving Directions: From John Young Pkwy, W Carroll St, Michigan Ave and Mill Slough Rd to Windsor Oak Ct in Kissimmee
  • Direction Faces: North

Community

  • Community Name: 34744 - Kissimmee
  • Community Features: Deed Restrictions, Gated Community - No Guard, Pool, Sidewalks
  • Association: Yes
  • Assoc. Name: Leslie Ludlam / AMG of Central Florida
  • Assoc. Fees Include: Community Pool, Pool Maintenance, Private Road
  • Pet Restrictions: Please contact the Home Owners Association for pet restrictions

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Electricity Available, Public, Sewer Connected, Street Lights, Water Available

Structural Information

  • Architectural Info: Contemporary
  • Architectural Style: Contemporary
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Blinds
  • Stories/Levels: Two
  • Square Feet: 1,380
  • Sq. Ft. Source: Public Records
  • Year Built: 1999

Lot Features

  • Lot Size (Acres): 0.02
  • Lot Size (Sq. Ft.): 871
  • Lot Size: 871
  • Frontage: Street Paved, Private Road
  • Street/Road Desc.: Paved

Financial Considerations

  • Association Fee: $180
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $2,008.32
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINDSOR OAKS PB 8 PB 42 LOT 12
  • Flood Zone Info: X
  • APN: 142529236500010120
  • Property ID: 142529236500010120
  • Block/Lot/Section: 1

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— 1638 Windsor Oak Ct —

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NMLS#: 1598647

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Schools serving 1638 Windsor Oak Ct

School District:Osceola County School District
NameGradesDistance
Mill Creek Elementary School, Kissimmee, FL
1700 Mill Slough Road, Kissimmee, FL 34744
PK-50.5 mi
Denn John Middle School
2001 Denn John Lane, Kissimmee, FL 34744
6-80.3 mi
Gateway High School
93 Panther Paws Trail, Kissimmee, FL 34744
9-121.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1638 Windsor Oak Ct Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/13/2025
Price Reduced
$284,900
-3.42%
MLS
9/05/2025
Listed
$295,000
288.16%
MLS
8/27/2014
Sold
$76,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1638 Windsor Oak Ct

Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,298
14%
$162,329
3%
2024
$2,008
3%
$157,755
3%
2023
$1,949
3%
$153,161
15%
2021
$1,900
1%
$133,200
-10%
2022
$1,873
-1%
$148,700
20%
2021
$1,900
21%
$123,500
62%
2019
$1,567
22%
$76,230
10%
2018
$1,287
1%
$69,300
3%
2017
$1,279
—
$67,500
1%
2016
$1,277
7%
$66,800
10%
2015
$1,189
17%
$60,900
18%
2014
$1,016
2%
$51,700
3%
2013
$997
—
$50,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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1638 Windsor Oak Court, Kissimmee, FL 34744 (MLS# S5133782) is a Townhouse property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 1638 Windsor Oak Court is currently listed for $284,900 and was received on September 05, 2025. Want to learn more about 1638 Windsor Oak Court? Do you have questions about finding other Townhouse real estate for sale in Kissimmee? You can browse all Kissimmee real estate or contact a Coldwell Banker agent to request more information.

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