33 Pleasant Street, Nantucket MA

33 Pleasant Street – Designer-Updated In-Town Nantucket Retreat Welcome to 33 Pleasant Street, a private and serene sanctuary tucked away on one of Nantucket’s most desirable in-town streets. Set back from the road along a charming cobblestone path, the property is enveloped by lush, terraced gardens, mature trees, and beautifully landscaped grounds, creating a tranquil oasis just steps from downtown. Newly updated for 2026, the home features all-new furnishings curated by renowned interior designer Meredith Pakman, with storyboards included in the photos, creating a sophisticated beachy and cohesive aesthetic throughout. The main residence is a classic two-story clapboard home thoughtfully designed across four levels to provide both privacy and versatility. On the first floor, the open-concept layout includes a spacious living room with a gas fireplace, a well-appointed kitchen, and an air-conditioned solarium that bathes the interior in natural light while providing seamless access to the outdoor gazebo and gardens. Nestled behind the main living areas, a large primary bedroom (King) enjoys easy access to a full, tiled bathroom. The second floor features two bright and generously sized bedrooms (King, Twins (2)), one with an ensuite bath and the other with access to a full hall bath, along with a cozy sitting room and office overlooking the front patio, offering a quiet space for work or relaxation. The third floor provides overflow sleeping accommodations with two full beds and a daybed, perfect for children or additional guests with a TV sitting area. A fully finished basement with 4 built in twin bunks adds flexible living space, complete with laundry and a full bathroom. Ping pong table outside. A detached one-bedroom (Queen), one-bathroom cottage offers its own private living space and entrance, making it ideal for guests, extended family, or use as a rental or studio. A Juliet terrace overlooks the manicured gardens, further enhancing the property’s charm and sense of privacy. Split A/C in cottage. 33 Pleasant Street combines thoughtful interior design, expansive living space, and beautifully maintained outdoor areas with a prime in-town location, offering the rare opportunity to enjoy the best of Nantucket living in a serene and elegant setting.