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$4,500,000
7 Beds ⋅ 6 Baths ⋅ 73575037 MLS ⋅ NEW Status
A landmark of Magnolia's storied coastline, this extraordinary oceanfront estate has graced Shore Road since 1889. Set above the Atlantic on one of Cape Ann's most coveted seaside addresses, the residence masterfully blends timeless architecture with thoughtfully curated updates, creating a home that feels both historically significant and effortlessly livable. Sunlight pours through expansive windows, illuminating gracious rooms designed for intimate gatherings and grand entertaining alike, while six fireplaces add warmth and character throughout. Outside, terraces and gardens frame panoramic ocean vistas where the rhythm of the tides, passing sailboats, and spectacular coastal sunsets become part of everyday life. Just moments from Magnolia Village, beaches and miles of scenic conservation trails, this is a rare opportunity to become the next steward of one of the North Shore's most distinguished waterfront homes.

31 Shore Rd., Gloucester

Listing courtesy of Listing Agent: McDermott Group from Listing Office: Gibson Sotheby's International Realty.
$4,295,000
4 Beds ⋅ 4 Baths ⋅ 73573613 MLS ⋅ ACTIVE Status
OCEANFRONT LIVING AT ITS BEST! Welcome to 41B Wingaersheek Road, an exceptional 2023 modular coastal residence offering a rare combination of modern comfort, energy efficiency, investment potential, and direct access to one of Gloucester’s most coveted stretches of shoreline. Thoughtfully engineered and factory-built in precision-fabricated modules before being assembled on site, the home offers a sophisticated alternative to conventional construction. A combination of structural steel and wood framing creates a durable, highly engineered building envelope while maintaining a clean, modern aesthetic. Designed for year-round comfort and efficiency, this home features extensive closed-cell spray-foam insulation throughout the walls, floors, and roof. The property consists of two beautifully appointed residences, each offering 2 bedrooms and 2 full baths, creating a versatile 4-bedroom, 4-bath configuration. Both units feature bright, open-concept living spaces, sleek kitchens with quartz countertops, center islands, and stainless steel appliances, as well as in-unit washers and dryers. A convenient lockout door provides the option for the two residences to function independently as a multi-family property or be incorporated into one expansive single-family home, offering an ideal setup for extended family, guests, or those seeking additional private space. Steel structural components are integrated throughout the modular system, including engineered connections between modules, resulting in exceptional structural integrity and energy performance. Mechanical systems were carefully incorporated into the design, including heat-pump HVAC and air-conditioning, along with a heat-recovery ventilation system providing continuous whole-house ventilation. Plumbing and electrical systems were substantially installed within the factory-built modules and seamlessly connected during on-site assembly, allowing for an efficient and highly coordinated construction process.Designed for effortless coastal living, this home is equipped for year-round enjoyment. Step outside and follow the private path directly to the beach, where you can spend your days swimming or strolling the shoreline. This home offers the opportunity to create a private family compound, a sought-after vacation retreat, or an income-producing investment. Rarely available, this is a remarkable opportunity to own a piece of the Gloucester coastline.

41-B Wingaersheek Rd, Gloucester

Listing courtesy of Listing Agent: The Apex Team from Listing Office: Apex Realty Group, LLC.
$2,225,000
3 Beds ⋅ 3 Baths ⋅ 73573140 MLS ⋅ ACTIVE Status
A rare waterfront offering on Gloucester’s coveted Annisquam River, where an extraordinary vantage point captures sweeping views directly down the river rather than across to neighboring homes. With a Chapter 91 tidal dock at your doorstep, this 3-bedroom, 2.5-bath residence offers an exceptional connection to the water, from morning coffee overlooking the river to an afternoon boat ride to Wingaersheek Beach.Fully renovated with a second story added in 2012, the home was thoughtfully designed to maximize its remarkable setting. Water views unfold from every room, while each bedroom opens to its own private balcony overlooking the river. The primary suite features an ensuite bath and a front-row perspective of the ever-changing waterfront.At the heart of the home, a spacious, light-filled living and dining area offers an open layout framed by expansive water views and a dramatic floor-to-ceiling stone fireplace. Built-in shelving and a wet bar create an inviting setting for entertaining, while the generous kitchen features an eat-in island and adjoining breakfast nook, all oriented toward the scenery beyond.Step directly from the main living area onto an expansive 414-square-foot waterfront deck, creating a seamless extension of the home for dining, entertaining, or simply watching boats make their way along the Annisquam. An outdoor shower and one-car garage add convenience to a property designed for effortless waterfront living.Just seven minutes from downtown Gloucester yet surrounded by the beauty and tranquility of the river, this is a distinctive opportunity to experience one of Cape Ann’s most extraordinary waterfront settings.

55 Riverview Rd, Gloucester

Listing courtesy of Listing Agent: The Bramhall Team from Listing Office: Churchill Properties.
$4,295,000
4 Beds ⋅ 4 Baths ⋅ 73572954 MLS ⋅ ACTIVE Status
OCEANFRONT LIVING AT ITS BEST! Welcome to 41B Wingaersheek Road, an exceptional 2023 modular coastal residence offering a rare combination of modern comfort, energy efficiency, investment potential, and direct access to one of Gloucester’s most coveted stretches of shoreline. Thoughtfully engineered and factory-built in precision-fabricated modules before being assembled on site, this distinctive property offers a sophisticated alternative to conventional construction, with structural steel and wood framing creating a durable, highly engineered building envelope. Designed for year-round comfort and efficiency, the home features extensive closed-cell spray-foam insulation, heat-pump HVAC and air-conditioning, and a heat-recovery ventilation system providing continuous whole-house ventilation. The property consists of two beautifully appointed residences, each offering 2 bedrooms and 2 full baths, creating a versatile 4-bedroom, 4-bath configuration. Both units feature bright, open-concept living spaces, sleek kitchens with quartz countertops, center islands, stainless steel appliances, and in-unit laundry. Each residence also enjoys its own private deck, creating the perfect setting for morning coffee, outdoor dining, or relaxing while taking in the coastal surroundings. The upper-level residence is further enhanced by beautiful ocean views, offering a true sense of the seaside lifestyle. Step outside and follow the private path directly to the beach, where you can spend your days swimming, strolling the shoreline, and enjoying spectacular sunsets. Whether envisioned as a private family compound, luxurious vacation retreat, or income-producing investment, this property offers exceptional flexibility in one of Gloucester’s most desirable coastal locations. Ideally situated just minutes from Annisquam, downtown Gloucester, renowned restaurants, galleries, marinas, and all that Gloucester has to offer. A rare opportunity to own a distinctive piece of the Gloucester coastline and experience the lifestyle that comes with it. Rarely available, this is a remarkable opportunity to own a piece of the Gloucester coastline.

41-B Wingaersheek Rd, Gloucester

Listing courtesy of Listing Agent: The Apex Team from Listing Office: Apex Realty Group, LLC.
$1,190,000
9 Beds ⋅ 4 Baths ⋅ 73564309 MLS ⋅ ACTIVE Status
Rare opportunity to acquire a fully renovated 3-family property in a highly desirable Gloucester location, just minutes from Good Harbor Beach and offering beautiful ocean views. The property combines strong rental fundamentals with the lifestyle appeal of one of the North Shore’s most sought-after coastal markets. The property has been thoughtfully renovated throughout, featuring updated kitchens and bathrooms, modern finishes, in-unit laundry, and two dedicated parking spaces. The flexible three-family configuration provides multiple income streams and makes the property attractive for both long-term rental and seasonal/vacation rental strategies. With its proximity to Good Harbor Beach, Gloucester’s restaurants, harbor, and downtown amenities, the property is well positioned to benefit from strong demand from both year-round tenants and summer visitors. The property also offers excellent potential for an Airbnb/short-term rental strategy, subject to applicable City of Gloucester regulations and permitting requirements. A major component of the investment opportunity is the separate 368R Main Street lot, located directly behind the property. This additional parcel provides meaningful future upside and could potentially support an ADU, additional residential unit, or other development concept, subject to zoning, permitting, utilities, and site requirements. Please reach out for private showings.

366 Main St, Gloucester

Listing courtesy of Listing Agent: Kristi Gjikondi from Listing Office: Gjikondi Realty.
$1,250,000
5 Beds ⋅ 2 Baths ⋅ 73563023 MLS ⋅ ACTIVE Status
Enchanting Waterfront Cottage w/private dock on peaceful Goose Cove. Enjoy gorgeous water views and looking over the Cove at the most spectacular nightly sunsets. Very serene and much like living on your very own nature preserve. The cottage is warm and welcoming, with a wood paneled, multi-windowed mudroom with storage benches at the entryway, front to back living/dining room, kitchen, first floor bedroom (currently used as a den with pull-out couch) and full bath, a family room/sunroom across the back of the home. The kitchen is older style with a fabulous classic double porcelain sink and tons of storage. You will find four more bedrooms upstairs and a second full bath w/tub and shower. Windows abound throughout the home, offering stellar views from every room, and letting in abundant light and heavenly breezes. The property is beautifully landscaped, providing a continuous rolling display of colorful perennials. Close to Plum Cove Beach, the coveted Lighthouse Beach, the Annisquam River, and multiple trailheads into protected woodlands a short walk from your door.

79 Dennison Street, Gloucester

Listing courtesy of Listing Agent: Nina Quinlan from Listing Office: Melcher Real Estate Group.
$1,675,000
3 Beds ⋅ 3 Baths ⋅ 73562377 MLS ⋅ ACTIVE Status ⋅ ['Harbor Haven At Rocky Neck'] BLDG.
Drift Away! Come for the BOAT SLIP. Stay for the lifestyle. New construction waterfront Condo reimagines a previous 2-BR unit and INCLUDES an exclusive, seasonal deep-water boat slip. Interior photos posted are virtual representations of the open-design entertaining anchor - LR, DR, Kitchen - along with the Primary Ensuite and other living spaces. Review design plans and discuss finishes in the Model (Unit B). Harbor Haven at Rock Neck is unfolding in three phases. Phase 1 offers finished 1-BR options see MLS # 73522248 and #73522580. Enjoy unobstructed water/cityscapes, gentle sea breezes and a tranquil backdrop that feels worlds away, yet is convenient to vibrant galleries, restaurants, theater. This new construction Luxury residence features floor-to-ceiling water facing LR windows, A/C, quartz counterstops, stanless steel appliances, luxury plank flooring, recessed lighting. more. Envisioning a weekend retreat, pied-a-terre by the sea, year-round waterfront residence or an investment? Visit the Unit B (model) and chat about this 3BR option! Condominium Association fee is estimate based on (4) unis. Pets friendly and rentals (minimum 1 month, with 3 times/year limit) allowed. Come discover what makes this property and location so special!

64 Rocky Neck Ave. Unit A, Gloucester

Listing courtesy of Listing Agent: Janet Breiter from Listing Office: Keller Williams Realty Evolution.
$1,585,000
3 Beds ⋅ 2 Baths ⋅ 73557961 MLS ⋅ ACTIVE Status
Waterfront Haven on Goose Cove. Discover a rare opportunity to own an exceptional waterfront property on Cape Ann's North Shore, just an hour from Boston by car or commuter rail. Set directly on Goose Cove offering a private dock for swimming, fishing, and kayaking at any tide, along with sweeping water views and spectacular sunrises and sunsets from nearly every room in the house. Situated across from the Goose Cove Reservation, a Greenbelt Land Trust preserve teeming with shorebirds and waterfowl, this fully winterized home is a true year-round retreat, flooded with natural light and warmed by a cozy fireplace in the living room.Enter to panoramic water views from a bright living room with bay windows, and a gas Fireplace. The kitchen, with dishwasher and ample counter space, is ideal for everything from pancake breakfasts to lobster dinners — and the kitchen island offers views straight out over the cove. The dining area seats up to 10 and opens onto a deck for sunset viewing. Completing the first floor: a full bath and bedroom. a mudroom with washer/dryer leading to the back door and a pocket porch. The second floor offers a spacious primary bedroom with walk-in Cedar closet, a full bath, a family room and a large third bedroom A cozy backyard with a grape arbor leads down to a private dock — perfect for swimming, sunbathing, kayaking, or fishing. A short, scenic walk across the Annisquam River leads to the historic village of Annisquam. Nearby, explore trails around Goose Cove Reservoir and the surrounding locales of Rockport, Lanesville, Dogtown, Gloucester, Essex, and Ipswich — home to farmstands, seafood markets, and antique shops., easy access to swimming and boating, or just the charm of Cape Ann's coastal environs,

11 Dennison St, Gloucester

Listing courtesy of Listing Agent: Kristina Bengston from Listing Office: Annisquam Village Realty.
$4,295,000
4 Beds ⋅ 4 Baths ⋅ 73542573 MLS ⋅ PRICE CHANGED Status
Experience the best of Magnolia waterfront living at 16 Hesperus Circle. Situated at the center of a truly private landscape with unobstructed, breathtaking views of the Atlantic, this exceptional residence offers over 4,000 square feet of living space with 4 bedrooms and 3.5 baths. A flowing open layout is designed to maximize natural light and showcase the spectacular coastal setting, creating an ideal space for both everyday living and entertaining. Step outside to a stunning infinity pool overlooking the water, where endless ocean vistas provide the backdrop for unforgettable gatherings and quiet moments alike. Enjoy the rare combination of privacy and convenience, with Magnolia Beach, downtown Magnolia's shops and restaurants, and all that Cape Ann has to offer just a short walk away. A remarkable opportunity to own a premier waterfront home in one of Gloucester's most coveted seaside neighborhoods.

16 Hesperus Circle, Gloucester

Listing courtesy of Listing Agent: Amanda Armstrong Group from Listing Office: Compass.
$1,499,000
4 Beds ⋅ 3 Baths ⋅ 73534421 MLS ⋅ ACTIVE Status
Enjoy breathtaking, ever-changing ocean views stretching across Eastern Point and beyond. Set in one of Gloucester’s most picturesque locations, this charming property offers unobstructed water vistas and a truly memorable coastal lifestyle. Rich in character, the home is surrounded by lush, professionally landscaped gardens, a welcoming patio, beautiful flowering trees, and vibrant perennial beds. A private beach is just steps from your door, while stunning ocean views can be enjoyed from nearly every room and outdoor space. Wake each morning to spectacular sunrises over the water and spend your days taking advantage of endless opportunities for boating, swimming, and seaside relaxation. With sweeping views, exceptional natural beauty, and an unmatched setting, this is a rare opportunity to create a lifetime of cherished Gloucester memories.

69 Dolliver Neck Rd, Gloucester

Listing courtesy of Listing Agent: Kristin Francoeur from Listing Office: Gibson Sotheby's International Realty.
$2,295,000
2 Beds ⋅ 2 Baths ⋅ 73531602 MLS ⋅ ACTIVE Status
This is more than a home—it’s a coastal lifestyle. Follow the steps to the water and dive into the cove at high tide, or wander the beautiful beach at low tide. The views are simply unparalleled. Spend your evenings on the upper deck as the sunset sets the seascape ablaze with color.The chef’s kitchen features nearly new Thermador appliances, reclaimed American heart pine floors, and an oversized island perfect for casual dining. A 10-foot picture window, installed last year, frames the ever-changing coastal scenery. The living room, with its inviting fireplace, opens to a charming covered porch—ideal for outdoor dining from morning coffee to evening meals.Upstairs, the primary bedroom offers breathtaking views stretching beyond Eastern Point. A second-floor family room with access to the upper deck is especially magical in the summer and could be converted into a third bedroom. Welcome to Rocky Neck—a destination people love to visit and a place you’ll be proud to call home.

8 Bickford Way, Gloucester

Listing courtesy of Listing Agent: Barbara Dugan from Listing Office: Engel & Volkers By the Sea.
$849,000
1 Beds ⋅ 1 Baths ⋅ 73522580 MLS ⋅ ACTIVE Status ⋅ ['Habror Haven At Rocky Neck'] BLDG.
Dock, Dine & Drift Away at Harbor Haven. This newly-created condominium offers a rare opportunity to embrace the quintessential Cape Ann waterfront lifestyle. Tucked away in a secluded harborfront setting, COMPLETE WITH an exclusive seasonal deep-water boat slip accommodating up to a 25-foot vessel—allowing easy access from your private deck to the open waters of Gloucester Harbor and beyond! Enjoy unobstructed water/cityscapes, gentle sea breezes, and a tranquil backdrop that feels worlds away, yet is convenient to vibrant galleries, restaurants, and the maritime charm of Rocky Neck. Thoughtfully refreshed, the residence features A/C, quartz countertops, stainless steel appliances, refinished hardwood floors and individually-metered municipal water service. Envisioning a weekend retreat, pied-à-terre by the sea, year-round waterfront residence, or an investment addition to your portfolio? Harbor Haven is an exceptional offering in one of Cape Ann's most iconic coastal locations.

64 Rocky Neck Ave Unit C, Gloucester

Listing courtesy of Listing Agent: Janet Breiter from Listing Office: Keller Williams Realty Evolution.
$2,699,000
4 Beds ⋅ 5 Baths ⋅ 73510015 MLS ⋅ ACTIVE Status
Exceptional waterfront living on the Mill River, this 2021-built contemporary home offers beautiful unobstructed riverfront views with glimpses extending toward Wingaersheek Beach and Ipswich Bay. Thoughtfully designed with 4 bedrooms and 4.5 baths, the home features an expansive open-concept layout centered around a dramatic great room that flows seamlessly onto a spacious deck, perfect for enjoying the ever-changing waterfront scenery. A chef’s kitchen with walk-in pantry anchors the main living space, complemented by high-end finishes and effortless indoor-outdoor living ideal for entertaining. Step outside to your private dock - an exceptional bonus - offering direct access to the Mill River for boating, kayaking, or paddleboarding right from your backyard. Additional highlights include a dedicated home office, oversized 2-car garage, and energy-efficient systems for modern comfort. A rare opportunity to own a nearly new waterfront home in a prime Gloucester location.

498 Washington St, Gloucester

Listing courtesy of Listing Agent: Atlee Alman from Listing Office: Vadala Real Estate.
$2,200,000
73509397 MLS ⋅ ACTIVE Status
Rare opportunity to own a 3+ acre coastal parcel in Gloucester overlooking Essex Bay and Crane Beach. Set on a private road, this elevated, wooded lot offers exceptional privacy and the potential for a custom home in a premier Cape Ann location. Enjoy close proximity to Wingaersheek Beach, marinas, and downtown Gloucester while surrounded by natural beauty. Generous acreage and topography provide a unique setting to design a year-round residence or seasonal retreat. Buyer to perform all due diligence. Board of Health has denied septic approval; property being sold as-is.

19 Two Penny Ln, Gloucester

Listing courtesy of Listing Agent: McDermott Group from Listing Office: Gibson Sotheby's International Realty.
$4,595,000
5 Beds ⋅ 3 Baths ⋅ 73503067 MLS ⋅ ACTIVE Status
Presenting a rare waterfront Eastern Pt compound spanning 3 contiguous parcels, ideally located between the yacht club and iconic lighthouse. This unique offering includes two single-family homes and a charming bunkhouse. 127 features a two-story, 2-BR home with a flexible first floor: 2 BRs, den, and screened porch which can comfortably host additional sleeping, and the stunning second-floor features an open-concept kitchen, dining, and living area with cathedral ceiling and a 30-foot wraparound deck. 129 is a single level, 3-BR bungalow with an updated kitchen, open living/dining, sunroom, and spacious wraparound deck. Completing the property, 131 has the delightful 11' x 15“ bunkhouse (has electricity, no plumbing), and is outfitted with 4 beds and a waterfront window that opens to an outdoor bar. A one-of-a-kind coastal retreat, with character and versatility - perfect for hosting family and guests. Attached is a feature sheet that provides detailed information about each parcel.

127-131 Eastern Point Blvd, Gloucester

Listing courtesy of Listing Agent: Barbara Dugan from Listing Office: Engel & Volkers By the Sea.
$2,950,000
4 Beds ⋅ 3 Baths ⋅ 73421894 MLS ⋅ ACTIVE Status
OPEN HOUSE SATURDAY SEPT 5 FROM 2:30 - 4. EXCEPTIONAL OPPORTUNITY TO LIVE ON THE HARBOR WITH YOUR OWN DEEP WATER DOCK approx. 290 feet long with a recently renovated 4-bedroom 2 1/2 bath harbor front home on SMITH'S COVE. The dock is fully licensed with a Chapter 91 permit, providing legal compliance for the owner. Sits across the harbor from Rocky Neck, renowned for its artist colonies, galleries, shops, and restaurants, this home offers a front-row seat to the bustling, picturesque harbor and easy access to the vibrant cultural life of Gloucester's waterfront. The home has all the modern conveniences with a state-of-the-art kitchen with all high-end appliances. There is a huge pantry off the kitchen. A spacious primary bedroom suite over the heated garage includes its own bath, while two additional bedrooms feature walkout decks and a skylight in the fourth bedroom. Large deck off living room all ooverlooking this spectacular harbor. There is another room that could be an office and is close to the main bedroom. There are two baths on the second level and a half bath with a washer-dryer hook-up on the first floor.

263 East Main Street, Gloucester

Listing courtesy of Listing Agent: Jeanne Carpenter from Listing Office: J. Barrett & Company.
$1,999,000
5 Beds ⋅ 4 Baths ⋅ 73397445 MLS ⋅ ACTIVE Status
Waterfront living with historic charm. Once a working mill, the structure has been transformed into a warm and inviting home, preserving its architectural heritage while embracing contemporary updates. The open-concept layout offers sunlit living spaces that showcase panoramic vistas of Annisquam River, Wingaersheek Beach, and Ipswich Bay. Whether you’re unwinding on the expansive deck, paddling across the water for a beach day, or gathering clams right from your shoreline, this property delivers a true coastal lifestyle. Inside, the ambiance is both airy and intimate, perfect for hosting family or enjoying quiet evenings. The main house exudes a nautical elegance, with a layout that evokes the feeling of life aboard a luxury vessel. A separate apartment above the garage provides private accommodations for guests, and the partially finished upper level offers opportunities to tailor the home to your future needs.

672 Washington Street, Gloucester

Listing courtesy of Listing Agent: Joshua Mulvey from Listing Office: Mulvey Real Estate, LLC.

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