5500 GULF BOULEVARD 4246, St Petersburg, FL 33706

• 2 beds |
• 2 baths |
• 835 sqft

Property Description

Experience one of the most reliable income-producing opportunities on St. Pete Beach with this fully furnished, turnkey condo-hotel residence located inside the award-winning AAA Four Diamond Tradewinds Island Grand Resort. This rare two-bedroom, two-bath unit delivers exceptional performance, generating over $40,000 in true net annual income after HOA fees, taxes, insurance, and management, making it ideal for investors, 1031 exchange buyers, or anyone seeking a high-ROI Gulf-front rental property. Owners enjoy the unique benefit of up to 28 personal-use days per year, plus exclusive discounts on dining, cabanas, and resort amenities, creating the perfect balance between investment and personal enjoyment. Overlooking lush tropical landscaping and steps from the resort’s world-famous beachfront, this spacious condo features a private balcony, multiple sleeping configurations, a separate living area with sleeper sofa, and a convenient kitchenette with full-size refrigerator, cooktop, microwave, and dishware—ideal for both guests and extended stays. As part of the Tradewinds rental program, all bookings, maintenance, housekeeping, and property management are handled onsite, offering a fully hands-free ownership experience. Demand stays high year-round thanks to the resort’s 1,000+ feet of pristine sugar-sand Gulf shoreline, nationally recognized hospitality, and its continuous calendar of weddings, conventions, corporate retreats, sports groups, and tourism events that consistently boost occupancy. Owners and guests enjoy access to over 40 acres of resort amenities, including nine swimming pools, 13 restaurants and bars, waterslides, parasailing, jet-ski rentals, beach cabanas, tennis and pickleball, mini golf, fitness centers, a full activities program, and even paddleboat rides through the resort’s winding waterways. Nearby, you’ll find all the best of St. Pete Beach—from Corey Avenue shops and waterfront dining to Sunset Beach, Pass-a-Grille, Fort De Soto Park, Johns Pass Village, and convenient access to both Tampa International Airport and St. Pete–Clearwater International Airport. Blending effortless passive income, resort-style living, and unbeatable Gulf Coast appeal, this Tradewinds condo-hotel unit offers everything today’s coastal investors are looking for. A rare opportunity for reliable returns and personal enjoyment in one of Florida’s most iconic beachfront resorts.

Listing Status:

Active

Date Added:

December 17, 2025 at 06:00AM

Listing Office:

KELLER WILLIAMS REALTY PORTFOLIO COLLECTION : 727-489-0800

Listing Agent:

Chase Walseth : 727-755-3830

MLS ID:

TB8457302

Interior

• General: Kitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanSolid Wood CabinetsStone CountersThermostat
• Appliances: CooktopMicrowaveRefrigeratorWine Refrigerator
• Laundry: Common AreaLaundry Room
• Flooring: CarpetCeramic Tile
• A/C: Central Air
• Heating: CentralElectric

Exterior

• General: BalconyBasketball CourtCourtyardDog RunLightingOutdoor ShowerPlaygroundRain GuttersSidewalkSliding DoorsStorageTennis Court(s)Heated
• Other Structures: CabanaGazeboTennis Court(s)Rear PorchCovered
• Pool: GuniteHeatedIn GroundLighting
• Parking: Open

Construction

• Roofing: Built-Up
• Windows: Shades
• General: BlockStuccoOneSlab

Location

• Road/Access: AsphaltPaved
• HOA Amenities: Basketball CourtGolf CoursePickleball Court(s)SaunaSpa/Hot TubCable TVPoolElectricityEscrow Reserves FundInsuranceInternetMaintenance StructureMaintenance GroundsMaintenanceManagementPest ControlPrivate RoadRecreational FacilitiesSecuritySewerTrashWater
• Originating MLS: Stellar MLS
• County: Pinellas

Lot

• Zoning: JACARANDA BEACH VILLAS CONDO PHASE IIIUNIT 424606-32-16-43555-000-4246
• View: PoolWater

Utilities

• Utilities: BB/HS Internet AvailableCable ConnectedElectricity ConnectedPublicSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Condominium

This listing courtesy of Chase Walseth, KELLER WILLIAMS REALTY PORTFOLIO COLLECTION