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$375,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,305 Sq. Ft.
  • Updated 1 day ago
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Short Sale. Welcome to "Bikinis & Martinis," a unique and beautifully maintained cottage in the highly sought-after Margaritaville Resort Orlando, ideally located just steps from premier resort amenities. This 2-bedroom, 2.5-bathroom, two-story home offers a spacious and functional floor plan, making it perfect as a primary residence, second home, or vacation rental investment. Designed with inviting coastal architecture and filled with natural light, the home features an open-concept living and dining area with modern finishes throughout. The well-appointed kitchen includes quartz countertops, stainless steel appliances, abundant cabinetry, and a breakfast bar with seating-ideal for entertaining or everyday living. A large-capacity washer and dryer, ceiling fans, and thoughtful upgrades further enhance comfort and convenience. Step outside from the kitchen to your private tropical oasis, complete with a patio, lounge chairs, hot tub, lush landscaping, palm trees, and charming shell pathways-perfect for relaxing or hosting guests. Upstairs, both bedrooms offer privacy and feature en-suite bathrooms with glass-enclosed shower stalls. This home includes the Margaritaville Resort Orlando-approved "Sail Away" Ethan Allen furniture and housewares package, valued at over $25,000. Everything conveys with the sale, including blinds, drapes, TVs, artwork, kitchen essentials, dishware, linens, and more-making this property truly turnkey. Located within one of Central Florida's most desirable resort communities, residents and guests enjoy world-class amenities, including multiple resort-style pools, a fitness center, spa services, and an on-site water park. Just a short walk away is the vibrant Sunset Walk entertainment district, featuring popular restaurants, bars, live music, retail, and family-friendly attractions. Conveniently located just minutes from Walt Disney World Resort, as well as Universal Orlando and SeaWorld, this property offers unmatched access to the best of Central Florida. Shopping, dining, and major travel routes-including Orlando International Airport-are all within easy reach. Whether you're seeking a full-time residence, vacation getaway, or income-producing property, this exceptional cottage offers the perfect blend of location, lifestyle, and investment potential-where every day feels like a vacation.

Full Property Details for 3058 Pirate Way

General

  • Price: $375,000
  • HOA FEE: $468/month
  • Taxes: $9,460 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6394128
  • Updated: 4/1/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: 1-7 Days

Interior

  • Number of Rooms: 5
  • Interior Features: Ceiling Fan(s), Open Floorplan, PrimaryBedroom Upstairs
  • Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Furnished
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Inside, Laundry Closet

Additional Information

  • Spa: Yes
  • Spa Description: Above Ground, Heated

Exterior

  • Exterior Features: Irrigation System, Lighting, Rain Gutters, Sidewalk
  • Deck/Patio: Front Porch, Patio
  • Porch/Patio/Deck: Front Porch, Patio

Parking

  • Parking Features: Open

Location

  • Area: 34747 - Kissimmee/Celebration
  • County: Osceola
  • Development Name: 34747 - Kissimmee/Celebration
  • Subdivision: ROLLING OAKS PH 5
  • Driving Directions: From I-4, Take FL 429 North to Exit 192. Head east on 192 take a right onto Inspiration Drive to entrance. Left on Fins Up Cir to Right on Pirate Way. House is on the Right
  • Direction Faces: Southeast

School Information

  • Elementary School: Westside K-8
  • Middle School: West Side
  • High School: Celebration High

Community

  • Community Name: 34747 - Kissimmee/Celebration
  • Community Features: Dog Park, Fitness Center, Gated Community - Guard, Park, Playground, Pool, Sidewalks
  • Association: Yes
  • Assoc. Name: Amanda Narehood
  • Assoc. Fees Include: 24-Hour Guard, Cable TV, Maintenance Grounds, Pest Control, Security, Trash
  • Pet Restrictions: Buyer must verify with HOA all information regarding pet restrictions and County Ordinances.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

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

Structural Information

  • Architectural Info: Florida, Key West
  • Architectural Style: Florida, Key West
  • Exterior Const.: Block, HardiPlank Type, Stucco, Wood Frame
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 1,305
  • Sq. Ft. Source: Public Records
  • Year Built: 2018

Lot Features

  • Lot Size (Acres): 0.02
  • Lot Size (Sq. Ft.): 871
  • Lot Size: 871
  • Lot Dimensions: 24 x 40
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt

Financial Considerations

  • Association Fee: $468
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • CDD: Yes
  • Tax Amount: $9,460.02
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: Short Sale
  • Legal Description: ROLLING OAKS PH 5 PB 26 PGS 132-140 LOT 98
  • Flood Zone Info: X
  • APN: 42527500500010980
  • Property ID: 42527500500010980
  • Block/Lot/Section: 1

Listed by Creegan Group

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Listing agents

— 3058 Pirate Way —

  • Creegan Group

  • Creegan Group

Get Pre-Approved Today

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 3058 Pirate Way

School District:Osceola County School District
NameGradesDistance
Westside K-8 School
2551 Westside Boulevard, Kissimmee, FL 34747
PK-52.8 mi
Celebration High School
1809 Celebration Blvd, Celebration, FL 34747
9-123.6 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 3058 Pirate Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/01/2026
Listed
$375,000
-31.19%
MLS
2/03/2022
Sold
$545,000
—
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 3058 Pirate Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,460
-9%
$414,300
-15%
2024
$10,379
5%
$484,700
7%
2023
$9,921
31%
$454,100
57%
2021
$7,555
-9%
$289,900
-29%
2022
$8,334
10%
$409,500
53%
2021
$7,555
6%
$268,300
8%
2019
$7,097
112%
$248,800
789%
2018
$3,344
—
$28,000
—
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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NMLS#: 1598647

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Listed by Creegan Group

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3058 Pirate Way, Kissimmee, FL 34747 (MLS# O6394128) is a Single Family property with 2 bedrooms, 2 full bathrooms and 1 partial bathroom. 3058 Pirate Way is currently listed for $375,000 and was received on April 01, 2026. Want to learn more about 3058 Pirate Way? 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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