$790,000

2199 TRIPOLI COURT, Kissimmee, FL 34747

9 beds |
6 baths |
4,391 sqft

Single-Family Home
Built in 2015
6,534sqft lot
2 car garage
$180/sqft
Listed 3 days ago

Property Description

Welcome to 2199 Tripoli, a spacious 9-bedroom, 5-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.

Listing Status:: Active
Date Added:: February 18, 2026
Data Last Updated:: February 19, 2026 at 7:24AM
Listing Office:: PABLA PROPERTIES : 407-967-2757
Listing Agent:: Sunny Pabla : 407-967-2757
MLS ID:: O6383484

General: Ceiling Fans(s)High CeilingsPrimary Bedroom Main FloorWindow Treatments
Appliances: Convection OvenDishwasherDisposalDryerElectric Water HeaterRangeRefrigeratorWasher
Laundry: Laundry Room
Flooring: CarpetCeramic TileLuxury Vinyl
A/C: Central Air
Heating: Central

General: Outdoor GrillSliding DoorsHeatedIn Ground
Pool: Child Safety FenceHeatedLighting

Roofing: Tile
Windows: Blinds
General: BlockStuccoTwoSlab

Road/Access: Paved
HOA Amenities: Guard - 24 HourCable TVCommon Area TaxesPoolInternetMaintenance GroundsRecreational FacilitiesTrash563.0Monthly
Originating MLS: Stellar MLS
County: Osceola

Zoning: SHORT TERMWINDSOR AT WESTSIDE PH 1 PB 23 PG 112-118 LOT 20518-25-27-5587-0001-2050

Utilities: BB/HS Internet AvailableCable ConnectedElectricity ConnectedUnderground Utilities
Water: Public
Sewer: Public Sewer

Source: Stellar MLS
Ownership: Fee Simple

This listing courtesy of Sunny Pabla , PABLA PROPERTIES

Monthly Payment

$Est. Payment

Principal & Interest $
Property Taxes $
Home Insurance $
VA Funding Fee $

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Location

Schools Nearby

Westside K-8 School

2551 Westside Blvd, Kissimmee, FL, 34747

Grades KG-8

0.47 miles away

Westside K-8 School

2551 Westside Blvd, Kissimmee, FL, 34747

Grades KG-8

0.47 miles away

Four Corners Upper School

9160 Bella Citta Blvd, Champions Gate, FL, 33896

Grades 6-12

2.92 miles away

Disclaimer: School and School District information courtesy of the National Center for Education Statistics (NCES). School boundaries may change. Proximity to listed schools does not guarantee enrollment eligibility. Contact the school district for more information and exact boundaries.