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5500 Gulf Boulevard #4246, 
St Petersburg, FL 33706

$537,500


2

Beds


2

Baths


835

Sq Ft


Condo


Virtual Tour

Active

Listed by

Chase Walseth

Keller Williams Realty Portfolio Collection

Last updated:

January 3, 2026, 01:09 AM

MLS#

TB8457302

Source:

MFRMLS

About This Home

5500 Gulf Boulevard #4246

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.

Home Facts

Condo

2 Baths

2 Bedrooms

Built in 1990

Price Summary

537,500

$643 per Sq. Ft.

MLS #:

TB8457302

Last Updated:

January 3, 2026, 01:09 AM

Added:

20 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

2

Bathrooms

Total Bathrooms:

2

Full Bathrooms:

2

Interior

Living Area:

835 Sq. Ft.


Structure

Structure

Building Area:

835 Sq. Ft.

Year Built:

1990


Finances & Disclosures

Finances

Price:

$537,500

Price per Sq. Ft:

$643 per Sq. Ft.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.