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518 New Castle Ave, Portsmouth
$35,000,000
6 Beds ⋅ 9 Baths ⋅ 5114173 MLS
There are properties that simply cannot be replicated. Privately sited on 7.7 waterfront acres on Portsmouth's coveted Shapleigh Island, 518 New Castle Avenue is a once-in-a-generation New England estate, an extraordinary convergence of scale, privacy, architecture, and waterfront living just moments from the heart of downtown Portsmouth. With 13,450± square feet, this magnificent Shingle Style residence was conceived on a grand scale, pairing timeless coastal architecture with exceptional craftsmanship and sophisticated modern living. Georgian-inspired millwork, stately Tuscan columns, intricate wainscoting, and beautifully proportioned interiors create a residence of remarkable presence, while walls of windows capture sweeping water views and an ever-changing maritime landscape. Across 17 rooms, the estate offers 6 bedrooms, 7 full and 2 half baths, and an impressive collection of formal and informal living spaces equally suited for everyday living and grand-scale entertaining. A newly added balcony overlooking the pool creates an elevated vantage point of the estate's sweeping water views. Beyond the home, manicured grounds descend toward the Piscataqua River, where a private deep-water dock provides direct access to Portsmouth Harbor and the open Atlantic beyond. An attached 3-car garage is complemented by a separate 2-car garage with a finished 1-bedroom, 1-bath guest accommodation above, creating a private and flexible retreat for visitors. Nearly 6,000 square feet of unfinished lower-level space offers exceptional flexibility and storage, while a new roof completed in 2025 represents a significant recent improvement. Yet perhaps the estate's greatest luxury is one that cannot be recreated: complete seclusion across 7.7 waterfront acres while remaining connected to downtown Portsmouth and its cultural, culinary, and coastal lifestyle. 518 New Castle Ave is a landmark NH estate and a rare opportunity to steward one of the region's defining legacy properties.

518 New Castle Ave, Portsmouth

15 Pickering Ave, Portsmouth
$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

395 Little Harbor Rd, Portsmouth
$5,200,000
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

28 Walden St, 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

500 Market St Unit 10R, Portsmouth
$815,000
1 Beds ⋅ 2 Baths ⋅ 5091377 MLS
***OPEN HOUSE, Sunday 10/24 from 10:30 to 12:00.*** WATERFRONT END-UNIT Townhouse with breathtaking views at desirable Noble’s Island! Overlooking scenic North Mill Pond, this immaculate, turnkey condo offers stunning sunsets, ever-changing waterfront scenery, and a front-row seat to local wildlife including Blue Herons, ducks, Cormorants, and even the occasional seal. Enjoy your morning coffee or evening cocktail from the private balcony while taking in the peaceful water views. Located just a short walk to downtown Portsmouth, Prescott Park, Strawbery Banke, and Pierce Island, you will love the convenience of having award-winning restaurants, boutiques, coffee shops, and entertainment just moments away, including The Music Hall, Jimmy's Jazz & Blues Club, 3S Artspace, and Seacoast Repertory Theatre. Inside offers over 1,000 square feet of bright, inviting living space across two levels. The open-concept main floor features a spacious living and dining area centered around a cozy wood-burning fireplace, perfect for relaxing or entertaining. The kitchen is equipped with cherry cabinetry, Corian countertops, a tile backsplash, stainless steel appliances, and a beverage cooler. A powder room and first-floor laundry add convenience. Upstairs, the generous primary suite feels like a private retreat with a sitting area showcasing incredible water views and a full bath with tub. Recent upgrades include fresh paint, new hardwood flooring throughout, a new central A/C and heating system installed in 2026, and a new water heater in 2023. Professionally managed association, and a low condo fee of $432/month. Plenty of easy onsite parking. No pets allowed. Virtual tour and floor plan available. Here is your chance to own affordable waterfront living in one of Portsmouth’s most desirable locations!

500 Market St Unit 10R, Portsmouth

1 Harbour Pl Unit 4i, Portsmouth
$2,333,000
2 Beds ⋅ 2 Baths ⋅ 5085159 MLS
Rare opportunity to own a modern riverfront loft at Portsmouth’s premier downtown address. Walk to dozens of restaurants, concerts, theaters, the farmers market, and seasonal festivals. Residence 4i was custom designed with nearly 2,000± SF including 45± SF storage, 2 bedrooms, and 2 full bathrooms. Giant, sound-resistant full-opening windows provide views of the river, Prescott Park, and the historic city. The open layout, high ceilings, and a spacious 2-island kitchen with abundant storage maximize the sense of space designed for entertaining. Automated Home features such as surround sound, automated lighting, remote-controlled shades, whole-unit water filter and reverse osmosis, bathroom mirror TVs, custom lighting, and blackout shades make your lifestyle at Harbour Place particularly relaxing. 2 HVAC zones are highly energy efficient, requiring minimal heating even in winter. Amenities include 2 assigned garage parking spaces with private Tesla/220V charging, an adjacent 120± SF storage room, and guest parking access. Gaze out over Portsmouth's charming waterfront, watching holiday fireworks, listen to Summer concerts, and monitor the beauty of an active port from the comfort of your living room or the common rooftop deck. Have a boat? There is an option to dock at the building’s private marina! Welcome to your mix of mesmerizing water views and quaint walkable city lifestyle that makes tax-friendly NH, and Portsmouth a recognized a top place to live in the country!

1 Harbour Pl Unit 4i, Portsmouth

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