5500 Gulf Blvd
Rarely Available PENTHOUSE.....2BED/LIVING ROOM/3Bath/Balcony at TradeWinds Island Resorts – Spectacular Gulf & Beach Views and TERRIFIC OPPORTUNITY with rental income history available! Experience the ultimate in beachfront ownership with this exceptional penthouse at the iconic TradeWinds Island Resorts on world-famous St. Pete Beach. Breathtaking views of the Gulf of Mexico, sugar-sand beaches, and the resort's tropical grounds, along with a history of investment potential in one extraordinary package! Beautifully appointed and completely turnkey, this spacious penthouse accommodates up to eight guests and features two bedrooms, including a primary suite with a king bed and a guest bedroom with two queen beds, a living room with sleeper sofa, dining area, three full bathrooms. The expansive balcony provides front-row seating for unforgettable sunsets, sparkling Gulf waters, and the vibrant resort atmosphere below. Unlike a timeshare, this is a fee-simple condominium that you own. Owners can enjoy up to 28 days of personal use annually while benefiting from participation in the resort's professionally managed rental program, providing the opportunity to generate income to offset ownership expenses. The villa is fully furnished and professionally maintained, beautifully decorated, and includes daily housekeeping and resort services—allowing for truly effortless ownership with monthly rental income distributions. Situated on approximately 40 tropical acres and 1,600 feet of pristine Gulf frontage, TradeWinds Island Resorts is one of Florida's most recognized beachfront destinations. Resort amenities include nine swimming pools, fifteen restaurants and dining venues, a full-service spa, fitness center, pickleball courts, beach cabanas, watersports, family activity programs, live entertainment, and endless opportunities for recreation and relaxation. Located within 30minutes to Tampa airport, major sports & spring training & entertainment venues, museums, shopping and world-class dining establishments. Known as a premier destination for weddings, conventions, family vacations, and memorable beachfront getaways, ownership also includes valuable owner privileges such as discounts on dining, beverages, and resort activities. Potential tax advantages, 1031 Exchange or self-directed IRA opportunities may further enhance the investment appeal. Whether you're seeking a beachfront retreat for family gatherings, a legacy property to create lasting memories, an income-producing investment, or the perfect combination of all three, this penthouse villa presents a rare opportunity to purchase. THIS is Florida Gulf-front living! *** JUST LET GO ***
Listing Information
Facts & Features
Location
Community Information
Architecture
Features & Amenities
Property Features
Square Footage
Tax & Financial Information
Schools
Pasadena Fundamental Elementary School
Thurgood Marshall Fundamental
Gulfport Montessori Elementary School
St. Petersburg Collegiate High School
Disston Academy
Gulf Beaches Elementary Magnet School
Bear Creek Elementary School
Extended Transition Countywide
School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.
Historical Data
Price History
| Date | Event | Price |
|---|---|---|
| 06/02/2026 | Listed for sale | $695,000 |
Listed by Sharon Griffin · FLORIDA WEST COAST REALTY · 7278670002
Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, Stellar MLS. All rights reserved.
Last Updated: August 21, 2026 at 4:17 PM | Source: Stellar MLS | MLS#: TB8514778

Similar Homes For Sale In St Pete Beach
Start Your Real Estate Journey
Whether you have questions about this listing, want to schedule a showing, or just want to talk through your options, Alene Civil is here to help. Reach out and expect a response within one business day.
How can I help?
Alene Civil is here to help. Reach out and expect a response within one business day.
Thanks — Alene Civil will be in touch shortly.
Make A Plan For Your Purchase
Know what you can afford before you start shopping — then run the numbers on any home you have in mind.
How much house can I afford?
- Principal & interest
- Property taxes
- Homeowner's insurance
- HOA dues
If your monthly savings are applied to the loan principal.
Enter your income, debts, and down payment to see how much home you may qualify for. Estimates only — not a lending decision.
Want to know more?
Keisha is here to help. Reach out and expect a response within one business day.
✓ Thanks — Keisha will be in touch shortly.
Your Next Chapter Starts With Just A Few Steps
Before you fall in love with a home, know what you can afford. Fill out a quick pre-approval so you're ready to make your move — on your timeline.

Pre-approval made easy
We're here to help you find the best option, not to help the best option find you. Trust that your information will not be shared with many different lenders like so many platforms do.
What type of home are you looking for?
How do you plan to use your new home?
Where are you in the home buying process?
Are you currently working with a real estate agent?
Do you currently own a home?
Is this your first time purchasing a home?
Do you plan to sell your current home before purchasing a new one?
Have you or your spouse served in the US military?
Veterans and active US military may be eligible for a $0 down VA loan.
What is your price range?
What is your current employment status?
What is your household pre-tax annual income?
What is your credit score?
Have you had a bankruptcy or foreclosure in the past 3 years?
Almost done — where can we reach you?
✓ Thank you for your time!
You'll hear back within one business day with your next steps.





