Discover this well-priced opportunity in the coveted Southside Village neighborhood: a charming 1938 cottage that combines classic character with modern amenities. Nestled on Bougainvillea Street, one of the most picturesque of Sarasota's beloved flower streets, this home features original wood floors, high ceilings, and a renovated kitchen, all while offering roomy storage uncommon for its vintage. Meticulously maintained, the property boasts updates including a newer HVAC system, tankless water heater, and metal roof. The main residence includes two bedrooms, two full baths, and a generously sized kitchen, complemented by spacious formal living and dining areas, a sunlit Florida room, and a convenient laundry/mud room. A cozy finished loft in the attic (not included in the square footage) overlooks the second bedroom and would be ideal for a play area, bunk room, art studio, or extra storage. Low-maintenance hardscaping enhances the outdoor space, while two detached structures at the rear of the property—a sizable garage and a one-bed, one-bath guest studio with a kitchenette—offer incredible versatility. A circular driveway allows for ample off-street parking, and brick-paved patios in back invite seamless indoor-outdoor living. Enjoy leisurely strolls through the neighborhood, with the highly regarded Southside School just a block away, vibrant shops and restaurants nearby in Southside Village, and world-famous Siesta Key just over a mile from your doorstep. This home is easy to maintain and has weathered the recent storms beautifully, making it perfect for year-round living, seasonal use, or a vacation rental.