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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.
$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. OH SUN 9/13

8 Orchard Road Unit B, Gloucester

Listing courtesy of Listing Agent: Bode Well Team from Listing Office: Compass.
$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.
$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.
$1,395,000
2 Beds ⋅ 4 Baths ⋅ 73528259 MLS ⋅ ACTIVE Status ⋅ ['Magnolia Shores'] BLDG.
Imagine the scale of a single-family home, the maintenance freedom of a luxury condominium, and the draw of the New England coast--all just around the corner from both the quaint seaside town of Manchester and the bustling Gloucester Center. Set within the exclusive Village at Magnolia Shores nestled on 50 park-like acres, this exceptional 2+bedroom, 3.5-bath, 3000+ sq ft residence redefines condominium living. Step inside to soaring 10ft coffered ceilings and a sun-flooded great room anchored by a gas fireplace, where living, dining, and a beautifully appointed designer kitchen open naturally into one another. An adjacent sunroom captures light from sunrise to sunset making it a spa-like sanctuary year round. The primary suite with a luxurious bath and walk-in closet, a second ensuite bedroom, and an inviting library/office make for easy first floor living. The lower level is a third suite: bedroom, full bath, and a spacious family room with sliders opening to the outdoors--it's where kids can play, teens can hide, and houseguests can find a home within your home!

28 Kennedy Rd Unit B, Gloucester

Listing courtesy of Listing Agent: Meg McGowan from Listing Office: Gibson Sotheby's International Realty.
$1,850,000
3 Beds ⋅ 4 Baths ⋅ 73510260 MLS ⋅ ACTIVE Status
Perched above the Atlantic, this brand-new luxury condo at The Overlook offers breathtaking views of the crashing waves and surfers at Good Harbor Beach. This is the last remaining opportunity to own in Gloucester’s most sought-after new development, The Overlook. Designed to maximize its dramatic elevation, the home features panoramic ocean vistas from every level. The interior is a study in light and volume, boasting soaring cathedral ceilings and a sophisticated 3-BR, 3.5-BA layout. The crowning jewel is the top-floor roof deck and flex suite with a wet bar—the ultimate setting for a high-end home office, art studio, or sunset lounge. Outside, expansive decks and a private rear patio offer seamless indoor-outdoor entertaining and provides places to relax and enjoy the views. With premium finishes and a track record of high demand, the peak of coastal living has arrived. Grab your surfboard and head to Good Harbor Beach or enjoy the view from your own home.

18R Starknaught Heights Unit A, Gloucester

Listing courtesy of Listing Agent: Nest | Syndi Zaiger Group from Listing Office: Compass.
$998,000
2 Beds ⋅ 4 Baths ⋅ 73466532 MLS ⋅ ACTIVE Status ⋅ ['5 Samoset Road Condominium'] BLDG.
Great New Pricing, on this one remaining luxurious unit at 5 Samoset Rd that present an unparalleled opportunity to experience refined living within its open concept floorplan with sunset views out over the Little River Estuary to the Annisquam River. The custom McCormick kitchen is a culinary dream with a large island, perfect for both casual dining and entertaining; featuring integrated paneled Bosch appliances, shaker cabinets, and stone countertops that blend seamlessly, creating a space that is as functional as it is beautiful. Solid White oak flooring throughout. All 3.5 baths feature Kohler fixtures and beautiful stone tile work. Large primary suite includes "wet room" experience ceiling-mounted rainhead shower along with a freestanding tub. The top floor can used as a second BR w/ its own full bath and walk-in closet or as the perfect getaway, the views across Ipswich Bay are unparalleled. The outside is landscaped with perennial plantings, native granite pathway & lush lawn. Large garage with work area 1/2 bath and storage

5 Samoset Rd Unit B, Gloucester

Listing courtesy of Listing Agent: Ann Rick Gloucester Group 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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