3476 Winton Ave
A rare, one of a kind Sarasota investment opportunity offering incredible flexibility, privacy, and income potential! Come invest in one of the most highly desirable areas in Florida. 1 parcel features 3 detached single family homes, plus additional space with potential to build a fourth home. Each residence offers 3 bedrooms and 2 bathrooms with updated interiors, charming individual designs, and lush tropical landscaping throughout. At the heart of the property is an inviting shared pool area with cabana spaces, creating a private tropical setting to relax, entertain, and enjoy the Florida lifestyle. The property is extremely private, with lush surroundings and plenty of room to expand and create an even more impressive compound. Currently income producing, the property includes active vacation rentals, while one cottage is utilized as student housing with bedrooms rented individually. Its proximity to Ringling College of Art and Design and New College of Florida adds another layer of rental potential. Continue the existing strategy or reimagine the property as a multi generational retreat, artist compound, private residential compound, or a unique setup for friends who want to live close while maintaining their own private residences. Tucked away on a private dead end street with no HOA and outside of a designated flood zone, the location is exceptional. Minutes from Downtown Sarasota, The Ringling Museum, Sarasota Bradenton International Airport, Ringling College, New College, dining, shopping, and Sarasota Bay, which is even within walking distance. With 3 existing homes, a pool and cabana area, multiple income possibilities, exceptional privacy, and room for future expansion, opportunities like this are incredibly hard to find in Sarasota. Keep everything operating as is and generate income, or bring your vision and unlock even more potential. Book your private showing today before your next investment opportunity in Sarasota,Florida is gone!
Listing Information
Facts & Features
Location
Community Information
Architecture
Features & Amenities
Property Features
Square Footage
Tax & Financial Information
Schools
Sarasota School Of Arts/Sciences
Sarasota Military Academy
Bay Haven School Of Basics Plus
Emma E. Booker Elementary School
Gocio Elementary School
Sarasota High School
Florine J Abel Elementary School
Booker Middle School
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 |
|---|---|---|
| 09/10/2026 | Listed for sale | $1,400,000 |
Listed by Chandler South · FLORIDA LIFE TEAM LLC · 9413039575
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: September 11, 2026 at 10:54 AM | Source: Stellar MLS | MLS#: A4705532

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