$245,000
1638 Windsor Oak Court
Kissimmee, FL 34744
Listing updated: July 9, 2026 at 10:31 PM ET
Listing courtesy of Preferred Real Estate Brokers · Lissette Escobar · MLS #S5153418 · Active · 407-440-4900Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Flood zone
About this home
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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history0 days on market
- Status: ActiveJul 10, 2026
- Listed$245,000Jul 9, 2026
- Price increased$245,000
Facts & features
- Property type
- Residential
- Sub type
- Townhouse
- Status
- Active
- Days on market
- 0
- Subdivision
- Windsor Oaks
- County
- Osceola
- Year built
- 1999
- Living area
- 1,380 sq ft
- Price/sq ft
- $178
- Building area
- 1,490 sq ft (Public Records)
- Lot size
- 871 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12097C0067G)
- Annual taxes
- $2,008 (2024)
- Parcel #
- 14-25-29-2365-0001-0120
- Zoning
- KSRP
- MLS #
- S5153418
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Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Half bathrooms
- 1
- Flooring
- Ceramic Tile, Laminate
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
- Interior features
- Ceiling Fans(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
- In Kitchen, Inside, Laundry Closet
- Stories / Levels
- Two
- Direction faces
- North
Heating & Cooling
- Heating
- Electric
- Cooling
- Central Air
HOA & Financial
- HOA fee
- $180 / Monthly
- Monthly HOA
- $180/mo
- Total monthly fees
- $180/mo
- Total annual fees
- $2,160
- HOA name
- Leslie Ludlam / AMG of Central Florida
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 1-7 Days
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Please contact the Home Owners Association for additional lease restrictions
Exterior & Construction
- Exterior features
- Lighting, Rain Gutters, Sidewalk, Sliding Doors
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Paved
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available, Electricity Available, Public, Sewer Connected, Water Available
Community
- Pets allowed
- Yes
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Living Room | First | 15x14 |
| Kitchen | First | 9x10 |
| Dining Room | First | |
| Bedroom 2 | First | 9x10 |
| Primary Bedroom | Second | 14x14 |
| Primary Bathroom | Second | |
| Bedroom 3 | Second | 14x14 |
| Bathroom 2 | Second | |
| Balcony/Porch/Lanai | First | |
| Bathroom 3 | First |
Listing Details
- Listing date
- 2026-07-09
- On market date
- 2026-07-09
- Original list price
- $245,000
- Occupant type
- Owner
- MLS area
- 34744 - Kissimmee
- Listing AOR
- Orlando Regional
- Status changed
- 2026-07-10
- Tax legal description
- WINDSOR OAKS PB 8 PB 42 LOT 12
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
Directions
From Main Street in Kissimmee, go east on US HWY 192 to right on Shady Lane, right on Partin Settlement Rd, and left on Stroupe Rd, home is on the right side
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Listing provided by Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively 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.
Based on information submitted to the MLS GRID as of July 9, 2026 at 10:31 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
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