1638 WINDSOR OAK, KISSIMMEE, FL 34744

$284,900 Was $295,000

Beds: 3

Baths: 2 Full / 1 Half

Sq. Ft.: 1,380 Sq. Ft.

Year Built: 1999

Lot Size: 0.02 Acres

Garage: N/A

Pool: No

DOM: 132

Property Overview

Status: Active

Property Type: Residential

MLS #: 83cc5ece0acc6c558f801961049fbd7d

Subdivision: WINDSOR OAKS

County: Osceola

HOA Fee: $180 (Monthly)

Year Built: 1999

Construction: Block, Stucco

Foundation: Slab

Roof: Shingle

Cooling: Central Air

Heating: Electric

Sewer: Public Sewer

Water Source: Public

Zoning: KSRP

Tax Amount: $2,008.32 (2024)

Listed On: Sep 5, 2025

Description

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.

Exterior Features

Lighting, Rain Gutters, Sidewalk, Sliding Doors

Directions

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

School Information

Elementary: N/A

Middle: N/A

High: N/A

Location

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Mortgage Estimator

*Estimate includes Principal & Interest (P&I) only. It does not include taxes, insurance, HOA fees, or PMI. Rates and payments may vary. Consult a lender for accurate figures.

Listing Information

Provided Courtesy of:

PREFERRED REAL ESTATE BROKERS

Listing Agent: Lissette Escobar

Information is deemed reliable but not guaranteed. Information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data last updated: February 11, 2026, 6:08 pm UTC

MLS Source: Stellar MLS Copyright © 2026

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