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KISSIMMEE, FL 34747 2199 TRIPOLI COURT

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Presented By: PABLA PROPERTIES with 407-967-2757. - 407-967-3287
  • MLS# O6383484
  • 02/16/2026
  • Request Tour
  • Request Info
  • Beds • 9
  • Baths • 6
  • SQFT • 4,391
  • Garage • 2

Home Details

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.
Presented By: PABLA PROPERTIES with 407-967-2757. - 407-967-3287

Interior Features for 2199 TRIPOLI COURT

Bedrooms

Total Bedrooms9

Bathrooms

Half Baths0
Total Baths6

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringCarpet, Ceramic Tile, Luxury Vinyl
Furnished Y/NFurnished
Heating Y/NYes
Interior AmenitiesCeiling Fan(s), High Ceilings, Primary Bedroom Main Floor, Window Treatments
Laundry FeaturesLaundry Room
Window FeaturesBlinds

General for 2199 TRIPOLI COURT

Additional Parcels Y/NNo
AppliancesConvection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, Washer
Assoc Fee Paid PerMonthly
Association Fee Includes24-Hour Guard, Cable TV, Common Area Taxes, Community Pool, Internet, Maintenance Grounds, Recreational Facilities, Trash
Association NameJoseph Muniz
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityKISSIMMEE
Community FeaturesClubhouse, Fitness Center, Gated Community - Guard, Playground, Pool, Sidewalks, Tennis Court(s)
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountyOsceola
DirectionsFrom 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.
Facing DirectionNorth
Flood Zone CodeX
Flood Zone Code XY
Full Baths6
Garage Spaces2
Garage Y/NYes
HOA Fee$563
HeatingCentral
Home Warranty Y/NNo
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionWINDSOR AT WESTSIDE PH 1 PB 23 PG 112-118 LOT 205
LevelsTwo
Listing TermsCash, Conventional, Private Financing Available
Living Area UnitsSquare Feet
Lot Size Square Feet6534
Lot Size UnitsSquare Feet
MLS Area34747 - Kissimmee/Celebration
Minimum Lease1-7 Days
Monthly HOA Amount563
New ConstructionNo
Occupancy TypeTenant
OwnershipFee Simple
Pets AllowedYes
Pool FeaturesChild Safety Fence, Heated, Lighting
Property SubtypeSingle Family Residence
Property TypeResidential
RoofTile
STELLAR_InLawSuiteYNNo
Senior Community Y/NNo
SewerPublic Sewer
Spa FeaturesHeated, In Ground
Standard StatusActive
StatusActive
Subdivision NameWINDSOR AT WESTSIDE
Tax Annual Amount11987
Tax Lot205
Tax Year2025
TaxOtherAnnualAssessmentAmount2910
Total Rooms12
UtilitiesBB/HS Internet Available, Cable Connected, Electricity Connected, Street Lights, Underground Utilities
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built2015
ZoningSHORT TERM

Exterior for 2199 TRIPOLI COURT

Building Area Total4860
Covered Spaces2
Exterior AmenitiesIrrigation System, Outdoor Grill, Sliding Doors
Foundation DetailsSlab
Lot Size Acres0.15
Lot Size Area6534
Private PoolYes
Road Surface TypePaved
SpaYes
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Schools

High School Hubert H Humphrey Middle School
Middle School N/A
Elementary School Big Hollow Elementary School

Steven Silcock

Broker Owner
Price $785,000
MLS#O6383484
List Date 02/16/2026
Property Type Single Family
Phone 407.574.0218
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