Step into timeless charm with this beautifully updated 1924 cottage, perfectly situated in Sarasota's coveted West of Trail neighborhood. Combining historic character with modern comforts, the main residence offers approximately 1,460 square feet of thoughtfully designed living space. Original hardwood floors, high ceilings, picture molding, a cozy wood-burning fireplace in the living room and an abundance of windows allowing natural light in all rooms highlight the home's classic appeal. The open-concept layout seamlessly connects the living room, updated kitchen, dining room and enclosed sunroom - perfect for a home office. All of the rooms ar generously sized. The primary bedroom has a spacious en-suite bathroom. Adding even more value is the recently renovated guesthouse, complete with kitchenette, screened-in porch, and private entrance. This versatile space is ideal for visitors, a creative studio, or potential rental income. Additionally both the main home and guesthouse feature brand-new metal roofs. Centrally located near downtown Sarasota, the shops and restaurants of Southside Village, and just minutes to the world-renowned beaches of Lido and Siesta Key, this unique property blends character, convenience, and flexibility.