Exceptional multi-generational residence or prime investment opportunity in Gillespie Park, eligible for short-term rentals under Sarasotas city policy. This contemporary two-story home was thoughtfully designed to accommodate two households living together independently, or easily converted into a spacious single-family residence with a stunning layout. Featuring a rare three-car garage and rear alley access (one of the few blocks in Gillespie Park with this feature), each floor offers over 2,200 sq. ft. of open-concept living space with two bedrooms, two bathrooms, 10-foot ceilings, and abundant natural light enhanced by motorized blinds. The ground floor includes front and rear foyers, a private walled courtyard with an outdoor kitchen and hot tub, and a chefs kitchen equipped with Thermador appliances, a natural gas six-burner cooktop, built-in ovens, two dishwashers, a walk-in pantry, and a spacious coffee/wine bar accessible from both the great room and courtyard-perfect for entertaining. A second full bath and a flexible office space are located just inside the front entry. The second floor, currently leased through March 2026, features a well-appointed kitchen with Bosch appliances, a laundry room, and two ensuite bedrooms. A large, partially covered balcony connects the great room and primary suite, bringing the outdoors in. Solar panels currently power the second-floor unit but can be redirected to the ground floor if desired. Both residences are connected to the garage and share access to a wide interior stairwell and elevator. This is a rare opportunity to live or invest in the vibrant Gillespie Park neighborhood-home to a dog run and tennis courts-and just steps from the Rosemary Arts District, downtown Sarasotas restaurants, shops, and theaters.