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$785,000
Original: $790,000
Active
2199 TRIPOLI COURT
KISSIMMEE, FL 34747 — WINDSOR AT WESTSIDE
9 Beds
6 Baths
4,391 sqft
0.15 acres
Built 2015
2-Car Garage
About This Property
Welcome to 2199 Tripoli, a spacious 9-bedroom, 6-bathroom pool home located in the highly desirable Windsor at Westside Resort — one of the area’s premier short-term rental communities. Designed with large groups and vacationing families in mind, this home offers a functional open-concept layout, generous bedroom count, and entertainment-focused design that makes it ideal for short-term rental use or a private vacation retreat.
A standout feature of the property is its custom-themed bedrooms, including: Assassin’s Creed-inspired room, Pokémon-themed room, Sonic the Hedgehog-themed room. These immersive spaces create a memorable guest experience and strong marketing appeal in the competitive Central Florida vacation rental market.
The main living area flows seamlessly into the dining and kitchen spaces, providing ample room for gathering and entertaining. Step outside to your private screened-in pool area — perfect for relaxing after a day at the parks.
Located within Windsor at Westside, residents and guests enjoy access to resort-style amenities including a clubhouse, lazy river, resort pool, fitness center, sports courts, and gated security. The community’s prime location offers convenient access to major attractions, shopping, dining, and highways.
Whether you are looking for a primary residence, second home, or investment property in a short-term rental approved community, this 9-bedroom home offers exceptional flexibility and opportunity.
A standout feature of the property is its custom-themed bedrooms, including: Assassin’s Creed-inspired room, Pokémon-themed room, Sonic the Hedgehog-themed room. These immersive spaces create a memorable guest experience and strong marketing appeal in the competitive Central Florida vacation rental market.
The main living area flows seamlessly into the dining and kitchen spaces, providing ample room for gathering and entertaining. Step outside to your private screened-in pool area — perfect for relaxing after a day at the parks.
Located within Windsor at Westside, residents and guests enjoy access to resort-style amenities including a clubhouse, lazy river, resort pool, fitness center, sports courts, and gated security. The community’s prime location offers convenient access to major attractions, shopping, dining, and highways.
Whether you are looking for a primary residence, second home, or investment property in a short-term rental approved community, this 9-bedroom home offers exceptional flexibility and opportunity.
Property Details
Basics
- Property Type
- Residential
- Property Subtype
- Single Family Residence
- MLS Number
- O6383484
- Days on Market
- 26
- Year Built
- 2015
- Levels
- Two
- Direction Faces
- North
- Occupant Type
- Tenant
Size & Structure
- Living Area
- 4,391 sqft
- Total Area
- 4,860 sqft
- Lot Size
- 0.15 acres
- Lot Sq Ft
- 6,534 sqft
- Bedrooms
- 9
- Full Baths
- 6
- Garage Spaces
- 2
Interior
- Flooring
- Carpet, Ceramic Tile, Luxury Vinyl
- Appliances
- Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, Washer
- Interior Features
- Ceiling Fans(s), High Ceilings, Primary Bedroom Main Floor, Window Treatments
- Laundry
- Laundry Room
- Windows
- Blinds
- Furnished
- Furnished
- A/C
- Central Air
- Heating
- Central
Exterior & Lot
- Exterior Features
- Outdoor Grill, Sliding Doors
- Construction
- Block, Stucco
- Roof
- Tile
- Foundation
- Slab
Water & Pool
- Pool
- Yes — Child Safety Fence, Heated, Lighting
- Spa
- Yes — Heated, In Ground
Community & HOA
- HOA
- Yes
- HOA Fee
- $563/Monthly
- Community Features
- Clubhouse, Fitness Center, Gated Community - Guard, Playground, Pool, Sidewalks, Tennis Court(s), Street Lights
- Pets Allowed
- Yes
Utilities & Systems
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected, Underground Utilities
- Cooling
- Central Air
- Heating
- Central
- Flood Zone
- X
Financial
- List Price
- $785,000
- Original Price
- $790,000
- Annual Taxes
- $11,987
- Tax Year
- 2025
- Listing Terms
- Cash, Conventional, Private Financing Available
- Special Conditions
- None