3476 WINTON AVENUESARASOTA, FL 34234
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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!
| 3 hours ago | Listing updated with changes from the MLS® | |
| 3 hours ago | Listing first seen on site |
Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-09-10 02:47 PM EDT
