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$790,000
4 Days On Site

2199 TRIPOLI COURT
KISSIMMEE, FL 34747

For Sale|Single Family Residence|Active
9
Beds
6
Total Baths
6
Full Baths
4,391
SqFt
$180
/SqFt
2015
Built
Subdivision:
WINDSOR AT WESTSIDE
County:
Osceola
Call Now: 407-495-2546
Is this the listing for you? We can help make it yours.
407-495-2546
2199 TRIPOLI COURT2199 TRIPOLI COURT2199 TRIPOLI COURT2199 TRIPOLI COURT
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Monthly Payment (Est.)

$3,604
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.

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.

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Listing Snapshot
Price 
$790,000
Days On Site 
4 Days
Bedrooms 
9
Inside Area (SqFt) 
4,391 sqft
Total Baths 
6
Full Baths 
6
Partial Baths 
N/A
Lot Size 
0.15 Acres
Year Built 
2015
MLS® Number 
O6383484
Status 
Active
Property Tax 
$11,987
HOA/Condo/Coop Fees 
$563 monthly
Sq Ft Source 
Public Records
Friends & Family
Recent Activity
4 days agoListing updated with changes from the MLS®
4 days agoListing first seen on site
General Features
Acres 
0.15
Attached Garage 
Yes
Direction Faces 
North
Foundation 
Slab
Garage 
Yes
Garage Spaces 
2
Levels 
Two
Parking 
Attached
Pets 
Yes
Property Sub Type 
Single Family Residence
Sewer 
Public Sewer
SqFt Total 
4860
Utilities 
Cable AvailableCable ConnectedElectricity ConnectedUnderground Utilities
Water Source 
Public
Zoning 
SHORT TERM
Interior Features
Appliances 
Convection OvenDishwasherDisposalDryerElectric Water HeaterRangeRefrigeratorWasher
Cooling 
Central Air
Flooring 
CarpetCeramic Tile
Furnished 
Furnished
Heating 
Central
Interior 
High Ceilings
Laundry Features 
Laundry Room
Spa 
Yes
Window Features 
Blinds
Additional Bedroom 
Dimensions - 12x12Level - Second
Bedroom 2 
Dimensions - 10x11Level - First
Bedroom 3 
Dimensions - 11x11Level - Second
Bedroom 4 
Dimensions - 12x11Level - Second
Bedroom 5 
Dimensions - 12x12Level - Second
Kitchen 
Dimensions - 20x18Level - First
Living Room 
Dimensions - 35x30Level - First
Loft 
Dimensions - 15x26Level - Second
Master Bedroom 
Dimensions - 15x18Level - First
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Exterior Features
Construction Details 
BlockStucco
Exterior 
Outdoor Grill
Pool Features 
HeatedPrivate
Private Pool 
Yes
Roof 
Tile
Spa 
Yes
Spa Features 
HeatedIn Ground
Windows/Doors 
Blinds
Community Features
Association Dues 
563
Community Features 
GatedClubhouseFitness CenterPlaygroundPoolSidewalksTennis Court(s)Street Lights
Financing Terms Available 
CashConventionalPrivate Financing Available
HOA Fee Frequency 
Monthly
MLS Area 
34747 - Kissimmee/Celebration
Roads 
Paved
Township 
25
Listing courtesy of PABLA PROPERTIES (407) 967-2757



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-02-22 09:18 PM EST

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
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