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

$1,699,000

3 Beds ⋅ 3 Baths ⋅ 73531398 MLS

Some homes simply hold furniture. Others hold generations of sandy feet, late-night swims, and the kind of summer memories that seem to stretch on forever. Welcome to 8 Schooner Ridge. Tucked into Gloucester’s coveted Castleview Estates with deeded access to Coffin’s Beach, this sun-filled Acorn contemporary was designed for gathering, unwinding, and living coastal life to the fullest. Vaulted ceilings, walls of glass, and back-to-back fireplaces create warm, dramatic living spaces, while distant views of Ipswich Bay remind you the ocean is never far away. The open floor plan flows easily from kitchen to entertaining spaces to expansive outdoor decking overlooking the pool and beautifully reimagined landscaping. A spacious primary suite, finished lower level for games, workouts or guests, whole-house generator, and oversized 3-car garage complete the retreat. Beach days, pool nights, sea breezes, and space for everyone — this is the rhythm of summer on Cape Ann.

8 Schooner Ridge, 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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