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$1,350,000
4 Beds ⋅ 4 Baths ⋅ 73575871 MLS ⋅ NEW Status
This spectacular property was custom-designed and built over the years by the owner of renowned builders Mill River Carpentry. Set on a beautiful lot along a peaceful street in Gloucester's desirable Riverdale neighborhood, this exceptional home showcases remarkable craftsmanship, expansive living spaces, and seamless indoor-outdoor living. A stone driveway welcomes you to an enormous mudroom that opens into a recently renovated custom kitchen featuring concrete quartz countertops and an impressive 60-inch refrigerator. The spacious living room is anchored by a woodstove with a beautiful granite surround and opens to a generous deck and pool area. The main level also offers a full bath with laundry, a comfortable sitting area off the kitchen, and a large dining room with cathedral ceilings. Exceptional details are found throughout, including radiant heat, tongue-and-groove pine ceilings, five-inch red oak flooring, and oversized windows that fill the home with natural light. The open first-floor layout extends effortlessly to a deck, patio, and screened porch, creating an ideal setting for entertaining and relaxing. The second floor features two bedrooms, a full bath, and an impressive primary bedroom with a cathedral ceiling and an oversized walk-in closet. The walkout portion of the basement provides a dedicated home gym area. A spacious breezeway offers flexible den or office space and leads to an oversized garage equipped with a 12-by-10-foot overhead door, a half bath, and radiant floor heat. Completing this remarkable property is a bright one-bedroom apartment above the garage - ideal for extended family, guests, or potential rental income. The apartment also features a large private deck with beautiful views of the Annisquam River and Ipswich Bay.

18 Holly St, Gloucester

Listing courtesy of Listing Agent: Mark Ventimiglia from Listing Office: Vadala Real Estate.
$620,000
4 Beds ⋅ 2 Baths ⋅ 73575107 MLS ⋅ NEW Status
Fantastic Two-Family Investment Opportunity! Ideally located in a desirable neighborhood walking distance to East Veterans Elementary school, this well-maintained two-family offers an excellent opportunity for investors or buyers looking to owner-occupy while generation rental income. Unit #1 entrance is the front door home with three bedrooms upstairs on the second floor, an open concept kitchen with center island stainless steel appliances, granite countertops, hardwood floor and a full bathroom. The spacious family with stackable laundry in closet. This unit has a parking spot in the driveway and off street parking. Unit # 2 is located in the back of the house, pull in the driveway and walk in your one bedroom, a kitchen, full bathroom, pantry/storage area, and in unit laundry. The property has a sharable yard to have grills and outside table and chairs. Whether you're looking to expand your investment portfolio or get into multifamily ownership with tenants already in place, this offers versatility, convenience, and excellent potential. Don't miss this opportunity to own a two-family in a great neighborhood close commuter rail, downtown Gloucester, parks and beaches.

19 Sadler Street, Gloucester

Listing courtesy of Listing Agent: Jill Michaud 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.
$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.
$2,100,000
4 Beds ⋅ 4 Baths ⋅ 73570897 MLS ⋅ ACTIVE Status
Beyond New Construction, 8 Orchard Road represents a level of customization rarely available in Gloucester. Nearly $350K in custom enhancements above the developer’s original specification have transformed this East Gloucester residence into an exquisite coastal home designed for comfort, entertaining, and effortless time away. Thoughtful floor plan is ideal for owners seeking a long-term home w/o the obligations of a large estate. A first-flr primary suite provides single-level living w/laundry hookups, while a second-flr primary suite offers privacy for guests & family. Both en-suite baths feature radiant heated flrs. Upstairs, a spacious, vaulted gathering room opens to an extended balcony overlooking the yard & grounds. A wet bar alcove features marble countertops, refrigerator, wine storage, and dishwasher and invites morning coffee, evening cocktails, and adds ease to large gatherings. Yorktowne custom cabinetry brings unmistakable quality & elegance to the kitchen, centered around an oversized island w/seating for six. Bosch induction cooking, Kohler Professional Chef Edition faucet, tailored cabinet storage, mixer lift, and networked appliances combine refined design with everyday functionality. The dining area features a custom blown-glass chandelier and nine-foot built-in buffet, while the sitting room is grounded by a striking marble fireplace-surround quarried from Vermont. Loving attention has been given to the exterior landscape as a continuation of the home's comfort, utility and luxury. Extensive hardscape, Corten steel privacy planters, perennial & shrub plantings, a propane fire-pit, and NewAge outdoor kitchen w/grill, sink, year-round storage and seating allow outdoor entertaining to be enjoyable, even for the host. EPE wood shower and changing cabana make beach days & cycling adventures a breeze. Integrated technology adds ease & confidence for owners who travel. Lutron automation controls 63 lighting & shade devices, complemented by whole-house water filtration, Moen water monitoring, remotely accessible irrigation, smart NEST thermostats, and networked appliances. Situated near Gloucester’s beaches, harbor, Rocky Neck Artists' community, and East Gloucester’s dining & galleries, 8 Orchard Road offers a rare combination of architectural distinction, extensive customization, sophisticated technology, and generous outdoor living. This a turnkey coastal home designed for owners who want to arrive, settle in, and simply enjoy. 1st OH 9/12

8 Orchard Road Unit B, Gloucester

Listing courtesy of Listing Agent: Bode Well Team from Listing Office: Compass.
$2,200,000
4 Beds ⋅ 2 Baths ⋅ 73563828 MLS ⋅ ACTIVE Status
Welcome to Coffins Beach, where private roads, rare deeded beach rights, pristine white sand and crystal-clear waters and tennis/pickleball courts all create an exceptional coastal setting. Set on a large lot, this well-maintained 1971 Contemporary offers 2,038 sq. ft. of comfortable living space with four bedrooms and two full baths—equally suited for seasonal escapes or year-round living. Elevated among the trees, the home enjoys expansive bird's-eye views toward the Annisquam River and the Ocean bringing together coastal scenery with the privacy and shade of its wooded surroundings. The open main level is oriented toward the view, with large picture windows and sliding glass doors connecting the living spaces to the deck. A remodeled kitchen with upgraded cabinetry, glass tile backsplash, countertop dining and stone countertops opens to the dining and living areas, while a fireplace adds warmth for cooler evenings and year-round enjoyment. Multiple decks and outdoor spaces extend the living area outside, with plenty of room to relax after a day at the beach or simply enjoy the surrounding landscape that also includes a private patio garden. Four well-proportioned bedrooms provide flexibility for family and guests, while two full baths complete the home. Master suite with vaulted ceilings opens to a private sunroom and deck for stunning view. Move-in ready and set within a highly sought-after coastal community, offering the rare combination of private beach access, water views, privacy and the flexibility to enjoy Gloucester in every season. Schedule a private viewing to experience the setting, views and distinctive lifestyle this property offers. Extensive renovations also include newer roof, windows, exterior, decking, sunroom, energy efficient Viessmann furnace, hot water heater and more. Furnishings and Household items negotiable making this a turn key option.

2 Dune Circle, Gloucester

Listing courtesy of Listing Agent: Suzanne Manley from Listing Office: Charlesgate Realty Group, llc.
$1,995,000
4 Beds ⋅ 5 Baths ⋅ 73560363 MLS ⋅ ACTIVE Status
Experience the best of Gloucester’s coveted coastal lifestyle in this newly renovated home in a truly spectacular location across from Bass Rocks Golf and Tennis Club and just minutes from Good Harbor Beach. Thoughtfully updated for modern living, this spacious residence offers 4 bedrooms, 1 office, 3 full bathrooms, and 2 half bathrooms, including a convenient first-floor primary suite. Designed for effortless entertaining and everyday comfort, the home features a remarkable 700-square-foot covered, wrap-around porch, perfect for enjoying sea breezes, morning coffee, and relaxed gatherings. Above, a 160-square-foot sun deck captures beautiful views of Gloucester Harbor and the Twin Lights, creating an inviting setting for sunset conversations or serene coastal moments. Additional highlights include a detached garage with flexible space above, parking for up to 5 cars, HERS-rated energy performance, and EV Charging Ready infrastructure—an ideal combination of coastal charm, efficiency, and future-ready convenience. OPEN HOUSE SAT 9/12 12:00-2:00 and SUN 9/13 12:00-2:00

45 Beach Road, Gloucester

Listing courtesy of Listing Agent: Ginger Attaya from Listing Office: Gibson Sotheby's International Realty.
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 73544994 MLS ⋅ ACTIVE Status
One of the most extraordinary First Period homes still in private hands, the 1678 William Haskell House overlooks the same shimmering tidal marshes where William Haskell harvested salt hay more than 3 centuries ago. Set on 2½ acres of rolling lawns and marshes, the property includes the remarkably preserved original house, a substantial 1920s ell, and a magnificent antique barn. Largely untouched throughout its 340+ year history, the home offers an authentic glimpse into early New England life. A meticulous restoration has discreetly introduced modern wiring, plumbing, and geothermal heating while preserving the home's soul. Four bedrooms & 3 baths blend seamlessly into the historic fabric. The barn offers a beautifully finished entertaining room & covered porch overlooking the marshes; imagine drinks there at sunset and then dining inside below the antique timbers! An irreplaceable opportunity to become the next steward of one of New England's most remarkable historic properties!

11 Lincoln St, Gloucester

Listing courtesy of Listing Agent: Michael Selbst from Listing Office: Gibson Sotheby's International 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.
$1,189,900
4 Beds ⋅ 3 Baths ⋅ 73531534 MLS ⋅ ACTIVE Status
Breathtaking new construction SF home nestled in the serene Bay View area of Gloucester, offering the perfect blend of modern luxury and seaside charm. Masterfully designed with fine craftsmanship and a coastal lifestyle, this spacious 2,600 sq. ft. home features a seamless open-concept layout. The chef-inspired kitchen boasts a large center island flowing into a cozy family room anchored by a contemporary electric fireplace all just steps to the outside deck. A versatile den/dining room, half bth, and convenient mudroom off the attached 2-car garage complete the main level. Upstairs, retreat to your private primary suite oasis with a stylishly tiled custom shower. 3 additional generous bedrooms share a beautifully appointed full bath, alongside a dedicated home office and separate laundry room. Situated on a tranquil private road, enjoy views of Ipswich Bay. Take a leisurely stroll to the pristine sands of Plum Cove Beach. Don't miss this opportunity to live in this seaside community!

5 Ciaramitaro Ct, Gloucester

Listing courtesy of Listing Agent: Melissa Skomurski from Listing Office: Churchill Properties.
$1,649,000
4 Beds ⋅ 3 Baths ⋅ 73527694 MLS ⋅ PRICE CHANGED Status
Now offered at a compelling new price, with beautiful hardwood floors revealed beneath recently removed carpeting, 8 Atlantic Road presents an exceptional opportunity just one tenth of a mile from the Good Harbor Beach footbridge. Set in an enviable East Gloucester location near the Back Shore, this beloved coastal retreat retains its classic character and features a remarkably spacious primary suite. The hardwood flooring extends throughout the front-to-back living room, dining room, up the staircase to the second floor, and into three of the four bedrooms. Outside, a beautifully landscaped, fenced yard unfolds around a large sparkling pool framed by lush gardens, a pool house with a bath, and a charming one bedroom guesthouse. A truly special offering in one of Gloucester’s most desirable neighborhoods.

8 Atlantic Rd, Gloucester

Listing courtesy of Listing Agent: Brackett Janis Group from Listing Office: Engel & Volkers By the Sea.
$1,099,000
4 Beds ⋅ 2 Baths ⋅ 73523928 MLS ⋅ ACTIVE Status
This beautifully maintained home has been extensively updated, offering true move-in-ready living. The 1st floor features a stunning chef’s kitchen with quartz countertops, custom cabinetry, and quality finishes throughout. Also on the main level are a spacious bedroom, dining area, front-to-back living room with a new gas fireplace, full bath, and an exceptional sunroom overlooking the expansive deck and backyard. Upstairs, you'll find a generously sized primary bedroom, two additional bedrooms, and a second full bath. A standout feature is the 12' x 20' shed with electricity and plumbing, offering exciting potential as a guest suite, in-law space, private office, studio, or workshop. Just steps from the property, enjoy deeded/shared access to the scenic Little River (which flows into the Annisquam), where you can swim, launch kayaks or paddleboards, go clamming, or simply take in the water views and coastal charm that make this location so desirable.

43 Woodward Ave, Gloucester

Listing courtesy of Listing Agent: Barbara Dugan from Listing Office: Engel & Volkers By the Sea.
$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.
$2,999,000
4 Beds ⋅ 5 Baths ⋅ 73433660 MLS ⋅ ACTIVE Status
Just steps from Wingaersheek Beach, 226 Atlantic Street is an extraordinary new home that blends timeless design with coastal living. Crafted for year-round comfort, this residence offers a chef-inspired kitchen with custom cabinetry, Thermador appliances, and walk-in pantry. The great room soars with a cathedral ceiling and stone fireplace, leading to a four-season porch that brings the outside in. Two serene primary suites—including one on the first floor for the ease of single-level living—feature spa-like baths with heated floors and soaking tubs. Expansive decks and a patio with gas hookups create ideal spaces for entertaining. With energy-efficient systems, EV and solar-ready infrastructure, and Wingaersheek’s crystal-clear waters and soft sand just steps away, this home is both a retreat and a destination.

226 Atlantic Street, Gloucester

Listing courtesy of Listing Agent: Nest | Syndi Zaiger Group from Listing Office: Compass.
$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.

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