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$9,500,000
4 Beds ⋅ 4 Baths ⋅ 5109617 MLS
Pickerings Neck. A truly rare opportunity on the waterfront in Portsmouth’s historic South End. Pickerings Neck is more than a property, it is a piece of Portsmouth’s maritime history and an opportunity to create a family compound unlike anything else in the city. Located on historic Pickering’s Neck, whose story reaches back to John Pickering’s arrival in 1633, this waterfront site later became part of Portsmouth’s important shipbuilding tradition. Today, the property offers an extraordinary collection of buildings and waterfront amenities, including a principal residence with an apartment, small warehouse, waterfront decks, docks, mooring and a separate building currently home to the South End Yacht Club.The real opportunity may lie in what comes next. Situated in the Commercial zoning district and within Portsmouth’s Historic District, the property presents a compelling canvas for creating an exceptional private family compound. Envision expanding and reimagining the existing residence or exploring the potential for a larger estate home, while repurposing the distinctive yacht club building into a remarkable waterfront guest residence or complementary living space. Few properties combine this degree of waterfront access, multiple existing structures, boating amenities, history and proximity to downtown Portsmouth. Step from your home to your dock, explore the Piscataqua and Portsmouth Harbor, or walk into the heart of the city. 15 Pickering offers something that simply cannot be recreated: the opportunity to write the next chapter of an extraordinary Portsmouth waterfront property.

15 Pickering Ave, Portsmouth
$1,520,000
2 Beds ⋅ 3 Baths ⋅ 5102368 MLS
Direct tidal waterfront just minutes from downtown Portsmouth is an extraordinary rarity, and this beautifully restored c.1810 home with a detached legal accessory dwelling unit (ADU) offers the opportunity to enjoy both, blending historic New England character with thoughtful modern updates in an exceptional waterfront setting. Designed to embrace its surroundings, the home captures sweeping water views and spectacular sunrises through windows on three sides. The custom cook's kitchen with handcrafted cabinetry opens to an inviting living area where a wall of glass frames the ever-changing waterfront landscape. Gentle ocean breezes and abundant natural light create a comfortable atmosphere throughout the seasons. Outside, a climbing hydrangea arbor welcomes you to a private brick patio and beautifully established gardens overlooking the water. It's an ideal setting for morning coffee, afternoon gatherings, or simply enjoying the peaceful shoreline. Launch a kayak or paddleboard directly from your backyard and explore the protected cove, home to a variety of coastal birds and marine life. The detached legal ADU offers exceptional flexibility as a guest house, private office, or income-producing rental. Filled with natural light, it features a vaulted ceiling, dramatic floor-to-ceiling window, loft sleeping area, full kitchen and bath, and a cozy gas fireplace. Located on a quiet dead-end street, yet only minutes from Portsmouth's celebrated restaurants, boutiques, galleries, The Music Hall, Prescott Park, Strawbery Banke Museum, and the city's vibrant waterfront, the property offers the perfect balance of peaceful waterfront living with proximity to amenities. A mahogany entry deck overlooks the granite cobblestone driveway with parking for three vehicles. A distinctive Seacoast property where historic charm, modern comfort, and waterfront living come together. Total square footage includes the detached legal ADU.

28 Walden St, Portsmouth
$3,300,000
2 Beds ⋅ 3 Baths ⋅ 5072206 MLS
For over two centuries, the Leonard Cotton House, a Portsmouth landmark, has stood as a centerpiece of Portsmouth’s historic Puddle Dock area. This Federal-style residence offers sweeping views across Strawberry Banke Historic Museum, Prescott Park, and the Piscataqua River. As one of the largest privately owned parcels in Portsmouth’s popular South End, it features off-street parking with room to construct a garage or carriage house. Situated on the corner of Hancock and Washington Streets, this property is a five-minute walk from Portsmouth’s cultural epicenter, Market Square. Genuine moldings, original eight panel doors, and distinctive dental moldings throughout, reflect the architectural grace of the mid-18th century. The finished attic, with its exposed beams and wide pine floors, provides a most inviting retreat. Originally home to the famous Capt. John Blunt, it became home to Leonard Cotton, a well known West Indies trade merchant. This historic property has served as law offices for forty years. It is anticipated that because of its flexible layout and phenomenal location it will be restored to its original prominence, as one of the city’s more distinguished residences. The Leonard Cotton House is not merely a piece of real estate; it is part of Portsmouth's legacy, awaiting its next steward.

144 Washington St, Portsmouth

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