Rare Sarasota opportunity with private guest quarters and direct access to the Legacy Trail! Welcome to 2712 Nancy Street, a unique and versatile property offering a spacious 3-bedroom, 2-bath main, 1-Carport residence plus separate guest quarters complete with an additional 4th bedroom, 1.5 baths, kitchen, and custom built-ins — ideal for multigenerational living, extended family, guests, rental income, or a private home office setup. Blending timeless 1950s charm with thoughtful updates, the home showcases beautiful Amish craftsmanship throughout, including custom built-ins, detailed carpentry, arched doorways, and classic barrel ceilings. Recent updates include a newer roof (3 years old), luxury vinyl flooring, granite kitchen countertops, and stainless steel appliances that are approximately 3 years old. The spacious Primary Suite offers exceptional flexibility with a walk-in closet, private bath, hobby room, and sitting room that can easily adapt to a variety of lifestyle needs. Outside, the property is designed for convenience and entertaining. A U-shaped driveway with pavers in both the front and backyard provides excellent and secure parking for a golf cart, boat, RV, or multiple vehicles. The fully fenced backyard features a storage shed and an entertainer’s dream setup complete with a covered patio/bar area and hot tub. With minimal grass cutting required and irrigation in the front yard, the outdoor spaces are both functional and low maintenance. Perfectly positioned in the heart of Sarasota, this home offers an unbeatable lifestyle with the Legacy Trail directly behind the property. Hop on your bike from the backyard and reach Payne Park, Publix, Alta Vista Elementary, Sarasota High School, Arlington Park, and Pinecraft in 15 minutes or less. Downtown Sarasota is just 2 miles away, while Lido Beach and Sarasota’s world-famous beaches are only a short drive away. This location combines convenience and recreation like few others. Walk to events at the Sarasota Fairgrounds without the hassle of parking, enjoy fireworks views from Bayfront Park, or take a quick bike ride for pizza or ice cream in nearby Pinecraft. Sarasota Memorial Hospital is less than 2 miles away, making everyday living exceptionally convenient. Situated on a quiet street where many neighbors have lived there for over 40 years, the neighborhood offers a welcoming atmosphere and a rich blend of cultures and backgrounds that truly make this area special. Whether you are searching for a primary residence, investment opportunity, or flexible multigenerational property, this home delivers location, lifestyle, character, and versatility all in one exceptional Sarasota address.