This quintessential Highlands cottage on coveted Cobb Road offers timeless charm, rich history, and an exceptional golf course setting. Perfectly positioned on a beautifully terraced 0.40-acre lot, the property enjoys golf course views, mature landscaping, and the peaceful character of one of Highlands' most sought-after neighborhoods. The screened porch offers a front-row view of the 7th fairway, creating a seamless connection to the course and the relaxed rhythm of club living. Originally built in 1955 as a two-story residence, the home carries a unique and beloved legacy. The current owners first purchased the property in the early 1960s and, after selling, reacquired it in 1995, expanding it to include a third level and transforming it into the spacious mountain retreat it is today. This three-story white clapboard home features 4 bedrooms, 4 full baths, and 2 half baths, offering ample space for family and guests. The main level showcases warm knotty Southern pine walls, creating an inviting mountain ambiance. The den features a beautiful stone fireplace, while the living room offers built-in bookshelves and a vaulted, beamed ceiling. A pristine 1994 American Trader “Princess” canoe stored in the rafters adds a unique nod to craftsmanship and mountain living. The dining area flows seamlessly into the kitchen, where ample counter space makes entertaining effortless. Additional highlights include a versatile craft room, ideal for hobbies or a home office, and a bedroom with golf course views and soft natural light. Upstairs, two spacious bedrooms each feature en-suite bathrooms and walk-in closets. Abundant windows and two skylights fill the level with natural light. The hallway between the two rooms has built-in bookcases and accent lighting, creating an ideal reading nook or study space. The lower level features a spacious living area and game room with a fireplace, along with an additional bedroom and full bath complete with a soaking tub and walk-in shower. An elevator provides convenient access to all levels. This level also includes a single-car garage and walk-out access to the lower yard, where stone terraced steps lead to the golf course. Located just minutes from downtown Highlands and within the prestigious Highlands Country Club community (membership optional), this property offers a rare combination of privacy, history, and proximity to town. A true Highlands classic, ready for the next generation of memories.