42 Chuck Hollow Road Nantucket, MA 02554

Welcome to 42 Chuck Hollow Road Nantucket, an extraordinary private estate known as Hollyhock, gracefully positioned atop one of the highest elevations in the coveted Tom Nevers East neighborhood. Set on approximately three acres of beautifully landscaped grounds, this exceptional Nantucket property offers panoramic Atlantic Ocean views, sweeping vistas of conservation land and Tom Nevers Pond, a separate guest cottage, and resort-caliber outdoor amenities rarely found on the island. Surrounded by rolling lawns, mature gardens, and protected natural beauty, 42 Chuck Hollow Road Nantucket delivers an unparalleled sense of privacy and tranquility while showcasing some of the most breathtaking elevated views on Nantucket. From both levels of the residence, expansive vistas stretch across the ocean, pond, and surrounding conservation land, creating an ever-changing coastal backdrop throughout the year. As you arrive, the estate's extraordinary landscaping immediately sets the tone. A sweeping semicircular oyster shell driveway is framed by river birch trees, hydrangeas, rhododendrons, lavender borders, and meticulously curated gardens featuring layers of texture, color, and seasonal interest. The grounds have been thoughtfully designed to complement the natural beauty of the property while creating a sense of arrival befitting a premier Nantucket estate. The main residence features five bedrooms and timeless architectural character, blending classic Nantucket design with sophisticated modern living. Rich in warmth and craftsmanship, the interiors have been thoughtfully enhanced by an owner with an acclaimed design background, resulting in beautifully curated spaces where antique furnishings and architectural elements are elegantly balanced with contemporary comforts and finishes. Adding to the property's appeal is a separate three-bedroom guest cottage, providing exceptional flexibility for extended family, guests, staff, or private accommodations. The guest house complements the main residence while preserving privacy and independence for all who visit. One of the estate's most distinctive features is its historic Shaker-style barn, originally dating to the 1840s and carefully relocated from the Berkshire region of Massachusetts. This remarkable structure contributes character, authenticity, and architectural significance rarely found in Nantucket real estate. Outdoor living at 42 Chuck Hollow Road Nantucket is truly exceptional. A recently added bluestone patio extends into a beautifully designed sunken garden anchored by a commanding stone fireplace, creating a dramatic focal point for entertaining and evening gatherings. Thoughtfully designed outdoor spaces encourage year-round enjoyment of the island's natural beauty. The resort-style amenities continue with a stunning 60-foot by 20-foot heated saline swimming pool complete with a retractable cover. Adjacent to the pool, a custom pavilion and fully equipped outdoor kitchen create the perfect setting for summer entertaining, outdoor dining, and relaxing with family and friends. The entire outdoor living area is enclosed by a secure fenced perimeter, enhancing both privacy and functionality. The elevated Tom Nevers location offers convenient access to Nantucket's South Shore beaches while providing a peaceful retreat removed from the bustle of town. Residents enjoy proximity to conservation trails, open landscapes, and some of the island's most scenic coastal areas. Combining three acres of privacy, panoramic ocean views, a five-bedroom main house, three-bedroom guest cottage, historic barn, heated pool, outdoor kitchen, and extraordinary landscaping, 42 Chuck Hollow Road Nantucket represents one of the island's most compelling estate offerings. Whether envisioned as a family compound, luxury summer retreat, or year-round residence, 42 Chuck Hollow Road Nantucket offers a rare opportunity to own a landmark property where natural beauty, architectural character, and resort-style living come together in one exceptional Nantucket estate.