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$770,000 -$15,000 (-1.91%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 9 Beds
  • 6 Full Baths
  • 4,391 Sq. Ft.
  • Updated 1 day ago
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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.

Full Property Details for 2199 Tripoli Ct

General

  • Price: $770,000
  • HOA FEE: $563/month
  • Taxes: $11,987 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6383484
  • Updated: 4/6/2026
  • Added to Site: 49 day(s) ago

Rental Information

  • Min. Lease: 1-7 Days

Interior

  • Number of Rooms: 12
  • Interior Features: Ceiling Fan(s), High Ceilings, Primary Bedroom Main Floor, Window Treatments
  • Appliances: Convection Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, Washer
  • Furnishings: Furnished
  • Flooring: Carpet, Ceramic Tile, Luxury Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 6

Bedrooms

  • Total Bedrooms: 9

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Child Safety Fence, Heated, Lighting
  • Spa: Yes
  • Spa Description: Heated, In Ground

Exterior

  • Exterior Features: Irrigation System, Outdoor Grill, Sliding Doors

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34747 - Kissimmee/Celebration
  • County: Osceola
  • Development Name: 34747 - Kissimmee/Celebration
  • Subdivision: WINDSOR AT WESTSIDE
  • Driving 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.
  • Direction Faces: North

Community

  • Community Name: 34747 - Kissimmee/Celebration
  • Community Features: Clubhouse, Fitness Center, Gated Community - Guard, Playground, Pool, Sidewalks, Tennis Court(s)
  • Association: Yes
  • Assoc. Name: Joseph Muniz
  • Assoc. Fees Include: 24-Hour Guard, Cable TV, Common Area Taxes, Community Pool, Internet, Maintenance Grounds, Recreational Facilities, Trash
  • Pet Restrictions: Check with HOA
  • Management Type: Full Time
  • Mgmt. Company: Full Time

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected, Street Lights, Underground Utilities

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Tile
  • Windows: Blinds
  • Stories/Levels: Two
  • Square Feet: 4,391
  • Sq. Ft. Source: Public Records
  • Year Built: 2015

Lot Features

  • Lot Size (Acres): 0.15
  • Lot Size (Sq. Ft.): 6,534
  • Lot Size: 6534
  • Street/Road Desc.: Paved

Financial Considerations

  • Association Fee: $563
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • CDD: Yes
  • Tax Amount: $11,987
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINDSOR AT WESTSIDE PH 1 PB 23 PG 112-118 LOT 205
  • Flood Zone Info: X
  • APN: 182527558700012050
  • Property ID: 182527558700012050
  • Block/Lot/Section: .

Listed by Pabla Properties

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— 2199 Tripoli Ct —

  • Pabla Properties

  • Pabla Properties

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2199 Tripoli Ct

School District:Osceola County School District
NameGradesDistance
Westside K-8 School
2551 Westside Boulevard, Kissimmee, FL 34747
PK-50.5 mi
Celebration High School
1809 Celebration Blvd, Celebration, FL 34747
9-124.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2199 Tripoli Ct Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/06/2026
Price Reduced
$770,000
-1.91%
MLS
3/16/2026
Price Reduced
$785,000
-0.63%
MLS
2/18/2026
Listed
$790,000
-4.36%
MLS
8/08/2024
Sold
$826,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2199 Tripoli Ct

Year
Property Taxes
Change
Tax Assessment
Change
2025
$11,987
-9%
$633,200
-12%
2024
$13,211
9%
$721,100
6%
2023
$12,141
31%
$678,100
36%
2021
$9,297
-12%
$497,500
-17%
2022
$10,557
14%
$599,100
18%
2021
$9,297
3%
$509,800
9%
2019
$9,069
-2%
$467,600
1%
2018
$9,267
3%
$462,200
5%
2017
$9,036
211%
$440,300
1001%
2016
$2,902
508%
$40,000
33%
2015
$477
—
$30,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Pabla Properties

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2199 Tripoli Court, Kissimmee, FL 34747 (MLS# O6383484) is a Single Family property with 9 bedrooms and 6 full bathrooms. 2199 Tripoli Court is currently listed for $770,000 and was received on February 18, 2026. Want to learn more about 2199 Tripoli Court? Do you have questions about finding other Single Family real estate for sale in Kissimmee? You can browse all Kissimmee real estate or contact a Coldwell Banker agent to request more information.

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