To schedule a showing of 1638 Windsor Oak Court, Kissimmee, Florida, Call David Shippey at 863-521-4517 TODAY!
$245,000 | 3 beds | 2 full baths | 1 half baths | 1,380 sqft
Kissimmee, FL 34744
- 3Beds
- 3.00Total Baths
- 2 Full, 1 HalfBaths
- 1,380SqFt
- 1999Year Built
- 0.02Acres
- MLS# S5153418
- Residential
- Townhouse
- Active
- Approx Time on Market6 days
- Area34744 - Kissimmee
- CountyOsceola
- Subdivision Windsor Oaks
Overview
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.
Agriculture / Farm
Association Fees / Info
Community Features: Pool, Gated, StreetLights, Sidewalks
Pets Allowed: Yes
Hoa Frequency Rate: 180
Association: Yes
Hoa Fees Frequency: Monthly
Association Fee Includes: Pools, RoadMaintenance
Bathroom Info
Total Baths: 3.00
Fullbaths: 2
Building Info
Window Features: Blinds, WindowTreatments
Roof: Shingle
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Style: Contemporary
Pool Features: Community
Patio: RearPorch, Covered, Enclosed, Porch, Screened
Exterior Features: Lighting, RainGutters
Fees / Restrictions
Financial
Original Price: $245,000
Disclosures: CovenantsRestrictionsDisclosure
Garage / Parking
Green / Env Info
Interior Features
Floors: CeramicTile, Laminate
Levels: Two
Laundry Features: Inside, LaundryCloset, InKitchen
Interior Features: BuiltInFeatures, CeilingFans, KitchenFamilyRoomCombo, LivingDiningRoom, OpenFloorplan, SolidSurfaceCounters, UpperLevelPrimary, WalkInClosets, WoodCabinets, WindowTreatments
Appliances: Dryer, Dishwasher, ElectricWaterHeater, Disposal, Microwave, Range, Refrigerator, Washer
Lot Info
Direction Remarks: 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
Lot Size Units: Acres
Lot Size Acres: 0.02
Lot Sqft: 871
Vegetation: PartiallyWooded
Lot Desc: Private, PrivateRoad, Landscaped
Misc
Other
Special Conditions: None
Security Features: FireSprinklerSystem, SmokeDetectors, GatedCommunity
Other Rooms Info
Property Info
Section: 14
Class Type: Townhouse
Property Sub Type: Townhouse
Construction Materials: Block, Stucco
Stories: 2
Total Stories: 2
Foundation: Slab
Human Modified: Yes
Room Info
Total Rooms: 10
Sqft Info
Sqft: 1,380
Bulding Area Sqft: 1,490
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,024
Tax Lot: 12
Tax Legal Description: WINDSOR OAKS PB 8 PB 42 LOT 12
Tax Block: 1
Tax Annual Amount: 2008.32
Tax Book Number: 8-42
Unit Info
Utilities / Hvac
Heating: Electric
Water Source: Public
Sewer: PublicSewer
Cool System: CentralAir, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableAvailable, ElectricityAvailable, MunicipalUtilities, SewerConnected, WaterAvailable
Waterfront / Water
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 sideThis listing courtesy of Preferred Real Estate Brokers
MLS# TB8520773 
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MLS IDX data last updated on 07-15-2026 7:43 PM EST.
If you have any questions on 1638 Windsor Oak Court, Kissimmee, Florida, please call David Shippey at 863-521-4517.
MLS# S5153418 located at 1638 Windsor Oak Court, Kissimmee, Florida is brought to you by David Shippey REALTOR®
1638 Windsor Oak Court, Kissimmee, Florida has 3 Beds, 2 Full Bath, and 1 Half Bath.
The MLS Number for 1638 Windsor Oak Court, Kissimmee, Florida is S5153418.
The price for 1638 Windsor Oak Court, Kissimmee, Florida is $245,000.
The status of 1638 Windsor Oak Court, Kissimmee, Florida is Active.
The subdivision of 1638 Windsor Oak Court, Kissimmee, Florida is Windsor Oaks.
The home located at 1638 Windsor Oak Court, Kissimmee, Florida was built in 2026.