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Opportunities like this are rare - available for the first time in over 40 years! Located in the heart of the Highlands, steps from Cherokee Park, this distinctive five-bedroom, five-bath home is situated at the end of prestigious Bonnycastle Avenue on nearly half an acre. With classic hardwood floors throughout, the home's layout is perfect for comfortable living and entertaining. Upon entry, you'll find a spacious formal living room that flows effortlessly into the rest of the home. French doors lead to a private study filled with natural light from charming stained-glass windows. On the opposite side, additional French doors open to a welcoming sunroom - ideal for relaxing or casual entertaining. The formal dining room connects seamlessly to the spacious eat-in kitchen, perfect for hosting gatherings. A conveniently located powder room is just off the living room. The second floor features a primary bedroom with a generous adjoining sitting room and three additional spacious bedrooms, all with hardwood floors. The finished third-floor space, equipped with its own HVAC system and water heater, includes a fifth bedroom and full bath, providing numerous possibilities as a guest suite, craft room, or personal retreat. Meticulously maintained by the current owners, recent updates include a new main HVAC system (just one year old), newer water heater, new sump pump, and a professionally waterproofed basement with a lifetime warranty. The slate roof beautifully complements the home's historic charm. An attached one-car garage accessible via the alley adds practical convenience.