Exceptional MULTI-GENERATION residence or PRIME INVESTMENT opportunity in Gillespie Park, eligible for SHORT-TERM RENTALS under Sarasota’s 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, tank-less hot water, individual laundry rooms, and abundant natural light enhanced with motorized window blinds. The GROUND FLOOR includes front and rear foyers, a private walled courtyard with an outdoor kitchen and hot tub, and a chef’s 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 BALCONCY 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 Sarasota’s restaurants, shops, and theaters.