Charming and timeless, this 1939 residence is located in the coveted WEST OF THE TRAIL and SOUTHSIDE SCHOOL DISTRICT. Classic Florida charm and listed on the historic registry, this beautifully UPDATED home spans nearly 2,200 SF and exudes character from every corner. NEW ROOF installed December 2024. A spacious yard, bordered by lush foliage and colorful landscaping, welcomes you to the large covered front porch. Enter through a beautiful solid wood leaded glass front door and discover wood trim casing framing the windows and doors, with original heart of pine wood floors adding warmth throughout. The oversized living room boasts a wood burning fireplace, built in bookcases, 9 ft ceilings and plantation shutters. Adjacent to the living room is the formal dining room, ideal for intimate meals or hosting gatherings. The updated kitchen is a chefs dream complete with custom Knotty Alder wood cabinets with crown molding and glass front detailed cabinets, granite beveled edge countertops, tile backsplash, stainless steel appliances including a Wolf 4 burner gas range, and wood beams adding charm to the space. Off the kitchen, the large family room features a second wood burning fireplace, vaulted ceiling, a bay window with built in bench seating for casual dining, and French doors leading to the private backyard oasis. The spacious primary bedroom includes a walk in closet with custom built ins and a beautifully updated ensuite bathroom with mosaic tile flooring, double vanity with quartz countertops, built in linen cabinet, charming window seat, and a walk in floor to ceiling tiled shower with frameless glass enclosure. A versatile bonus space off the primary suite is perfect for a nursery, office, studio, or TV room. Two additional bedrooms share a beautifully updated full bathroom that maintains the homes original charm. The backyard offers a true sense of retreat, tucked away behind mature, lush landscaping that provides exceptional privacy and a peaceful atmosphere. Enjoy a Trex deck, spacious paver patio, secluded hot tub, and a fully fenced yard. A detached two car garage with separate ample storage space completes the property. Ideally located just minutes from Southside Village, downtown Sarasota, Marie Selby Botanical Gardens, Sarasota Memorial Hospital, and the world renowned beaches of Siesta Key and Lido. Whether enjoying the shops and restaurants of Southside Village or the vibrant downtown bayfront, this home offers the best of Sarasota living. A rare opportunity to own a historic gem in one of Sarasotas most sought after neighborhoods with MOTIVATED SELLERS ready to negotiate.