Welcome to your timeless Sarasota retreat. Discover a blend of old Florida charm and modern living in this meticulously renovated 1932 Gillespie Park bungalow, ideally in the heart of downtown Sarasota. Surrounded by canopy oaks and rich with character, this historic gem offers a rare opportunity to own a piece of Sarasota's past, thoughtfully reimagined for today's lifestyle. Go onto the large, welcoming front porch, a peaceful place to unwind beneath the shade of century-old oak trees on breezy Florida evenings. Inside, the home's original charm greets you immediately, from vintage 10-pane windows (and some new hurricane impact-resistant windows) and warm pine floors to a cozy built-in reading nook with storage. The main house features a spacious one-bedroom layout, a full bath, and a flexible home office or den, ideal for work-from-home needs or overnight guests. A charming powder room showcases the original sink from the home's early days. The bright dine-in kitchen is a culinary dream with custom wood cabinetry, quartz countertops, a walk-in pantry, and striking custom tile backsplash. Premium appliances include a Thermador dishwasher, KitchenAid convection oven, Forno refrigerator/freezer, and custom range hood. A large laundry room features full-size LG front-load washer/dryer and the original utility sink. The spa-inspired primary bath offers a deep soaking tub, a glass-enclosed Carrera marble shower, and dual vanities with black marble countertops and lighted mirrors. Modern comforts meet historic integrity with a 2016 renovation with new French doors, trusses, plumbing, wiring and a 2018 roof. Main house HVAC is from 2010 and separate 2016 HVAC for the ADU and two water heaters. Go outside to a tranquil backyard oasis. A crushed shell driveway leads to a lush, low-maintenance garden with artificial pet-friendly turf, an outdoor shower and plenty of room to enjoy Sarasota's sunshine. A major bonus, the fully permitted two-story carriage house/guest suite (2016) includes a finished two-car garage with hurricane-braced, insulated garage door. Upstairs, antiqued wood floors, one bedroom, spacious living room, oversized walk-in closet with attic access and a bath with granite countertops. The guest kitchenette features a Bosch refrigerator/freezer, quartz counters, cabinetry and a sink, ideal for visitors or extended stays. The ADU is built to code with impact-rated windows and doors and is in the Downtown Neighborhood (DTN) zoning district. Just blocks from Gillespie Park's 10-acre green space, and downtown Sarasota's vibrant cultural scene and Bay Sarasota 53-acre community park. No HOA restrictions or fees. Visit Whole Foods, Sprouts, the farmers market, art galleries, theaters, and ride the free Bay Runner trolley to Lido Beach and St. Armands Circle. This rare, character-filled home is your urban oasis, steeped in history, elevated for modern living.