Michele Weiand

Michele Weiand Realtor 🇺🇸

$790,000.00
2199 TRIPOLI COURT, KISSIMMEE, FL - 34747
9 beds
6 baths
4,391 sqft
$790,000.00
2199 TRIPOLI COURT, KISSIMMEE, FL - 34747
Michele Weiand
$790,000.00
9 beds
6 baths
4,391 sqft
2199 TRIPOLI COURT, KISSIMMEE, FL - 34747
For Sale
Photo 1
  • Built in 2015
  • 2 garage spaces
  • $179.91/sqft
  • Lot size: 6,534 sqft
  • 1 days on market

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.

  • Directions: From I-4 to 192 West, go left on Westside Blvd, stay on Westside Blvd until it ends, turn right at resort main entrance, turn right onto Tripoli Ct and this home is on right.
  • County: Osceola
  • Geo subdivision: WINDSOR AT WESTSIDE

Features

Financial

Let's get in touch!

Michele Weiand

Michele Weiand

Realtor 🇺🇸

See also

For Sale
8811 MACAPA DRIVE, KISSIMMEE, FL - 34747
$790,000.00
9 bds
6 ba
4,391 sqft
8811 MACAPA DRIVE, KISSIMMEE, FL - 34747
For Sale
230 CLAWSON WAY, KISSIMMEE, FL - 34747
$849,000.00
9 bds
8.5 ba
4,630 sqft
230 CLAWSON WAY, KISSIMMEE, FL - 34747
For Sale
1885 GOBI DRIVE, KISSIMMEE, FL - 34747
$790,000.00
8 bds
6 ba
4,041 sqft
1885 GOBI DRIVE, KISSIMMEE, FL - 34747
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6383484
Listing updated: February 19, 2026 at 11:57AM
Listing provided by: Sunny Pabla, PABLA PROPERTIES
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