One Chester Street is an exceptional residence that perfectly blends historic charm with modern luxury. Situated at the edge of Nantucket's historic district where the Cliff area meets Brant Point, this home offers a prime location that provides easy access to the best of island living. This 18th-century ship captain’s home has been meticulously restored, preserving its original details, including five working fireplaces, while integrating contemporary amenities for today's lifestyle. Sold fully furnished with interior design by The Nantucket Looms, the home boasts four levels of living space, with six bedrooms and five and a half baths, it comfortably accommodates large groups, offering ample room for relaxation and privacy. The spacious open kitchen features the original 6' walk-in fireplace, breakfast area, adjoining a bright family/TV room that opens directly onto the rear deck, patio, and garden. The formal dining room features a beautiful lacquered finish. The outdoor space is equally impressive, with a unique artist-built gazebo and fire pit—a perfect spot for evening gatherings. The home’s renovations are top of the line, including all new plumbing, electrical, and HVAC systems, with high-end finishes throughout. The lower level is dedicated to entertainment, with a fully equipped game room including a combination ping pong/pool table, three TVs, a separate seating area, and a kitchenette. For quieter moments, the third-floor guest suite provides access to the roof walk with panoramic views of Nantucket Sound and Harbor, making it a wonderful spot to unwind. One Chester Street is the perfect combination of historic elegance and modern comfort.

Originally built in the 1800s, this exceptional property has been masterfully reimagined through the collaborative efforts of Main Street Construction and Mark Cutone Architecture. The result is a seamless fusion of historic preservation and modern luxury. Located just moments from Main Street in the heart of Nantucket’s historic district, the home’s front façade maintains its timeless charm, while the rear opens to sophisticated contemporary living. A stunning three-story custom staircase, crafted from glass and wood by EeStairs, serves as the visual and architectural centerpiece of the main residence. Spanning four levels, the home features five bedrooms—including one currently utilized as a dressing room—and three elegant living areas, offering a perfect blend of comfort and functionality. Completed in 2018, the detached studio provides additional space for entertaining and relaxation, all overlooking the private, beautifully landscaped yard. High-end finishes are found throughout both structures, including custom wire-brushed white oak flooring, integrated LED lighting, remote-controlled window treatments, and bespoke cabinetry by Faneuil Cabinetry. The property also includes two off-street parking spaces and is being offered fully furnished, presenting a rare turnkey opportunity in one of Nantucket’s most coveted locations.

Commercial CTEC lot. Currently leased until September 30, 2027 with 2, 1 year extensions. Lease has excellent cash flow, making it ideal for an investor who wants to continue to lease it as raw land or recognizes the value for future development. Utilities; town water, (sewer is at 9-11 Nancy Ann) cable and electric are available at the street. The lot is 118x210, is flat and open and is subdividable. CTEC allows for 40% ground cover. There are no structures on the property. The current tenant uses it to store construction equipment and material.

This CN zoned lot allows 40% ground cover. Ideally suited for a multiple of commercial uses. Proposed schematic plans #1 and #2 are in documents. Office building with 4 garage bays and 2 apartments, or multiple structures. See also the zoning chart for approved uses. Schematic plans have not been approved, but are for informational purposes only.