27 Longwood Drive Nantucket, MA 02554

Welcome to 27 Longwood Drive, Nantucket — a private 2.75-acre estate offering refined coastal living and timeless Nantucket charm. This spacious upside-down home features five bedrooms, three full bathrooms, and one half bathroom, perfectly designed for comfort, entertaining, and relaxation. Step into the inviting foyer with its dramatic curved staircase, leading to a stunning second-floor living area. The open-concept layout includes a cathedral-ceiling great room, custom fireplace, and a large dining space ideal for gatherings. The gourmet kitchen boasts distant views of Sankaty Light, bringing the island’s natural beauty right into your home. From the second-floor deck, enjoy serene mornings with coffee or peaceful evenings under the stars—an unmatched combination of privacy and tranquility. The lower level offers two covered porches, perfect for year-round outdoor entertaining. A beautifully designed carriage house complements the main residence, featuring an oversized two-bay garage, one bedroom, and one bathroom—ideal for guests or extended family seeking privacy. This exceptional Nantucket property at 27 Longwood Drive also allows for an additional 2,200 square feet of ground cover, offering ample opportunity to expand or customize your dream island retreat.