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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.

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

Perched above the Piscataqua River at the end of what most consider the prettiest road in historic Portsmouth, this exceptionally well-constructed contemporary offers a combination of waterfront living, privacy and recreation. Built into a natural slope overlooking the confluence of the Little Harbor branch of the Piscataqua River and Sagamore Creek, the home captures magnificent views of Little Harbor, New Castle, and the historic Wentworth by the Sea Hotel. Less than 100 yards upriver, the property shares the shoreline with the historic Wentworth-Coolidge Mansion, home of New Hampshire's first royal governor. The setting is quintessential Seacoast. Enjoy your morning coffee from an upper deck or lower-level waterfront patio as lobster boats make their way toward the open ocean. Clam diggers may be working the nearby flats, while striped bass fishermen follow schools of baitfish, and kayakers, paddleboarders and windsurfers enjoy the protected waters. The property's own waterfront tennis court offers a remarkable recreational amenity against the backdrop of Little Harbor and the New Castle shoreline. Multiple decks and outdoor living areas take full advantage of the changing tides, passing boats and expansive views. Just minutes from downtown Portsmouth's historic sites, celebrated restaurants, shops and cultural attractions, this distinctive property combines contemporary architecture, quality construction and an exceptional waterfront setting, where the beauty, history and maritime character of the Seacoast become part of everyday life.

4 Beds ⋅ 3 Baths ⋅ 5108874 MLS

Perched above the Piscataqua River at the end of what most consider the prettiest road in historic Portsmouth, this exceptionally well-constructed contemporary offers a combination of waterfront living, privacy and recreation. Built into a natural slope overlooking the confluence of the Little Harbor branch of the Piscataqua River and Sagamore Creek, the home captures magnificent views of Little Harbor, New Castle, and the historic Wentworth by the Sea Hotel. Less than 100 yards upriver, the property shares the shoreline with the historic Wentworth-Coolidge Mansion, home of New Hampshire's first royal governor. The setting is quintessential Seacoast. Enjoy your morning coffee from an upper deck or lower-level waterfront patio as lobster boats make their way toward the open ocean. Clam diggers may be working the nearby flats, while striped bass fishermen follow schools of baitfish, and kayakers, paddleboarders and windsurfers enjoy the protected waters. The property's own waterfront tennis court offers a remarkable recreational amenity against the backdrop of Little Harbor and the New Castle shoreline. Multiple decks and outdoor living areas take full advantage of the changing tides, passing boats and expansive views. Just minutes from downtown Portsmouth's historic sites, celebrated restaurants, shops and cultural attractions, this distinctive property combines contemporary architecture, quality construction and an exceptional waterfront setting, where the beauty, history and maritime character of the Seacoast become part of everyday life.

395 Little Harbor Rd, Portsmouth

A rare and truly exceptional offering in the heart of downtown Portsmouth—this one-of-a-kind property includes a luxury penthouse residence, a second residential unit, and two commercial storefronts, all offered in its entirety. Built in 2008 and meticulously maintained, the property blends modern construction, upscale amenities, and timeless interior style in an unbeatable downtown location. The main entrance on State Street opens to a foyer with elevator access to both residences and the lower level. A four-car garage is accessed from the rear of the foyer, while two ground-level storefronts with premier State Street frontage flank the entrance. Both retail spaces are leased to established tenants, with one at-will and one under lease. The second floor features a spacious three-bedroom, four-bath garden-style residence with an open-concept floor plan, hardwood floors, gas fireplaces, and three en suite bedrooms. The third and fourth floors comprise a stunning two-story penthouse offering four bedrooms and six baths, including four en suite bedrooms plus a fifth en suite office or guest suite. The expansive main living level showcases a chef’s kitchen with island, casual and formal dining areas, private office, mudroom, and rich cognac-toned wide-pine floors. Expansive decks span all three residential levels, each oriented toward the quiet, sun-filled, south-facing Court Street side. Additional highlights include secure private elevator access to each residence, four deeded garage parking spaces with additional storage, and a finished lower level ideal for a fitness room, wine storage, or flexible use space.Condominium conversion potential presents a rare investment or legacy ownership opportunity. Enjoy the many benefits of New Hampshire living, including no state income or sales tax, close proximity to the scenic coastlines and beaches of NH and Maine, and convenient access to 4 regional and international airports in less than one hour.

8 Beds ⋅ 12 Baths ⋅ 5085575 MLS

A rare and truly exceptional offering in the heart of downtown Portsmouth—this one-of-a-kind property includes a luxury penthouse residence, a second residential unit, and two commercial storefronts, all offered in its entirety. Built in 2008 and meticulously maintained, the property blends modern construction, upscale amenities, and timeless interior style in an unbeatable downtown location. The main entrance on State Street opens to a foyer with elevator access to both residences and the lower level. A four-car garage is accessed from the rear of the foyer, while two ground-level storefronts with premier State Street frontage flank the entrance. Both retail spaces are leased to established tenants, with one at-will and one under lease. The second floor features a spacious three-bedroom, four-bath garden-style residence with an open-concept floor plan, hardwood floors, gas fireplaces, and three en suite bedrooms. The third and fourth floors comprise a stunning two-story penthouse offering four bedrooms and six baths, including four en suite bedrooms plus a fifth en suite office or guest suite. The expansive main living level showcases a chef’s kitchen with island, casual and formal dining areas, private office, mudroom, and rich cognac-toned wide-pine floors. Expansive decks span all three residential levels, each oriented toward the quiet, sun-filled, south-facing Court Street side. Additional highlights include secure private elevator access to each residence, four deeded garage parking spaces with additional storage, and a finished lower level ideal for a fitness room, wine storage, or flexible use space.Condominium conversion potential presents a rare investment or legacy ownership opportunity. Enjoy the many benefits of New Hampshire living, including no state income or sales tax, close proximity to the scenic coastlines and beaches of NH and Maine, and convenient access to 4 regional and international airports in less than one hour.

58 State St, Portsmouth

Distinguished 1814 brick townhome in the heart of historic downtown Portsmouth offering a rare blend of luxury, flexibility, and long-term investment value. Enjoy iconic views of the Piscataqua River, Prescott Park, and Strawbery Banke Museum just steps from Market Square, the waterfront, renowned dining, boutiques, and cultural attractions. The ground floor, currently commercial with soaring 10’ ceilings, offers exceptional potential for conversion to high-end residential or continued mixed-use, opening to a private pocket garden/courtyard and shared one-car parking. Upper levels provide refined living spaces with exposed brick and beams, Rumford-style wood-burning fireplace, formal living and dining areas, solarium with park and river views, private deck for outdoor entertaining, and multiple flexible-use rooms ideal for bedrooms or offices. The fourth floor features two bedrooms with custom built-ins and a tiled three-quarter bath. Full basement with ample storage and second washer/dryer hookup. Retain mixed-use income potential or create a full four-story luxury residence totaling up to 2,982 SF an exceptionally rare offering in downtown Portsmouth. Great opportunity to purchase and entire building in one of the most central locations that this city has to offer. Under an hour from Boston's Logan International Airport. Unit offers a rented garage and a rear pocket garden that may also be capable of parking a very small car onsite with modifications.Offered below city assessment, presenting outstanding value in one of New Hampshire’s most sought-after waterfront cities.

3 Beds ⋅ 2 Baths ⋅ 5075026 MLS

Distinguished 1814 brick townhome in the heart of historic downtown Portsmouth offering a rare blend of luxury, flexibility, and long-term investment value. Enjoy iconic views of the Piscataqua River, Prescott Park, and Strawbery Banke Museum just steps from Market Square, the waterfront, renowned dining, boutiques, and cultural attractions. The ground floor, currently commercial with soaring 10’ ceilings, offers exceptional potential for conversion to high-end residential or continued mixed-use, opening to a private pocket garden/courtyard and shared one-car parking. Upper levels provide refined living spaces with exposed brick and beams, Rumford-style wood-burning fireplace, formal living and dining areas, solarium with park and river views, private deck for outdoor entertaining, and multiple flexible-use rooms ideal for bedrooms or offices. The fourth floor features two bedrooms with custom built-ins and a tiled three-quarter bath. Full basement with ample storage and second washer/dryer hookup. Retain mixed-use income potential or create a full four-story luxury residence totaling up to 2,982 SF an exceptionally rare offering in downtown Portsmouth. Great opportunity to purchase and entire building in one of the most central locations that this city has to offer. Under an hour from Boston's Logan International Airport. Unit offers a rented garage and a rear pocket garden that may also be capable of parking a very small car onsite with modifications.Offered below city assessment, presenting outstanding value in one of New Hampshire’s most sought-after waterfront cities.

36 State St, Portsmouth

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