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RARE MULTI-GENERATION FAMILY RESIDENCE OR INVESTMENT PROPERTY in Gillespie Park is located within the City of Sarasota’s short term rental policy. This contemporary two-story dual residence is graciously DESIGNED FOR TWO HOUSEHOLDS to reside together, yet independently, under one roof. With its attached THREE CAR GARAGE and paved rear-alley entrance (one of only a couple of blocks in Gillespie Park with an alley), EACH floor has a 2200+ sq. ft. , 2 bedroom/2 bath open floor plan with 10 ft. ceilings, and an abundance of natural light filtered through motorized window blinds. GROUND FLOOR RESIDENCE has both front and rear entrance foyers and a private walled courtyard with outdoor kitchen and hot tub. Its impressive kitchen features Thermador appliances, a natural gas six-burner cook top/built-in ovens and a commodious coffee/wine bar accessible from both the great room and courtyard for easy entertaining. Located just inside the front entry is a second full bath and closet-less office. SECOND FLOOR RESIDENCE: Currently leased through March 2026 has a spacious kitchen with Bosch appliances, laundry room, and two ensuite bedrooms. A large partially-covered balcony brings the outdoors in and opens to the great room and large primary suite. Solar panels, currently connected to the second-floor unit, can be switched to power the ground floor if desired. Each of the two residences are attached to the garage and there is a wide interior stairwell and elevator to second floor. This is an unusual opportunity to live and/or invest in Downtown Sarasota’s vibrant neighborhood of Gillespie Park (with dog run and tennis courts), while just steps from the Rosemary Arts District, Downtown restaurants, shops and theaters.