Wingaersheek Real Estate

Welcome to Wingaersheek, a hidden gem nestled in the picturesque city of Gloucester, Massachusetts. This charming coastal community is part of Essex County and is renowned for its stunning beaches, vibrant local culture, and breathtaking natural beauty. Wingaersheek Beach, with its soft sands and gentle waves, is a favorite among families and sun-seekers alike, offering a perfect spot for swimming, picnicking, and enjoying the serene coastal views.

The region boasts a rich maritime history, with Gloucester being one of the oldest seaports in America. Here, you can explore the quaint streets lined with historic homes, galleries, and boutique shops, all while soaking in the vibrant artistic spirit that the area is known for. Wingaersheek is not just about its stunning shoreline; it’s also a place where outdoor enthusiasts can thrive. The nearby salt marshes and tidal flats provide ample opportunities for kayaking, birdwatching, and fishing, making it an ideal location for nature lovers.

As part of Gloucester, Wingaersheek is conveniently located near a variety of dining options, from fresh seafood shacks to upscale restaurants offering locally sourced fare. The community is also committed to preserving its natural beauty, with numerous conservation areas and parks that invite residents and visitors to explore the great outdoors.

Whether you’re considering a permanent move or a seasonal getaway, Wingaersheek offers a unique blend of coastal charm, rich history, and a welcoming community. Discover your slice of paradise in this enchanting corner of Massachusetts!

Newest Listings in Wingaersheek

$4,295,000

4 Beds ⋅ 4 Baths ⋅ 73573613 MLS

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

$4,295,000

4 Beds ⋅ 4 Baths ⋅ 73572954 MLS

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

$2,200,000

4 Beds ⋅ 2 Baths ⋅ 73563828 MLS

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

$2,200,000

73509397 MLS

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

$1,225,000

3 Beds ⋅ 3 Baths ⋅ 73482119 MLS

Moments from the pristine shores of Wingaersheek Beach, this beautifully maintained three bedroom, two and a half bath home offers the perfect weekend retreat, seasonal escape, or year round coastal residence. Set in a picturesque setting with views of the Jones River, the property is filled with natural light and features hardwood floors with comfortable living spaces throughout including a kitchen open to the dining area and a family room with fireplace. The second level features three bedrooms and two full baths, including the primary suite. Outside, established perennial gardens and inviting outdoor spaces create a wonderful setting for relaxing or entertaining. Unfinished basement houses utilities & storage space. Two car garage beneath the home provides convenient parking and additional storage. Thoughtfully updated throughout, the home offers a low maintenance coastal lifestyle just moments from one of Cape Ann’s most beloved beaches.

178 Atlantic Street, Gloucester

$2,999,000

4 Beds ⋅ 5 Baths ⋅ 73433660 MLS

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

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