4 Waterfront and Massachusetts Estates from Beacon Hill to Duxbury

Along the water’s edge in Jamestown Shores, 129 Seaside Drive offers a true waterfront setting designed around the simple luxury of being near the shoreline. Located in Jamestown, the residence is presented as a residential offering with a coastal address that speaks for itself, where daily life can begin and end with the rhythms of the water just beyond. The listing keeps the focus on place—Jamestown Shores waterfront—letting the setting take center stage rather than a checklist of interiors. From this Seaside Drive location, the experience is about the calming presence of the waterfront and the sense of retreat it brings, whether you’re easing into quiet mornings or winding down as the light shifts over the water.

From its elevated setting on one of Egremont’s most desirable country roads, this contemporary estate takes in sweeping, south-facing views that stretch more than 30 miles across rolling meadows, mountain ranges, and Prospect Lake. Set on approximately 15 private acres, it balances seclusion with the ease of being just minutes from downtown Great Barrington and major Berkshire attractions. Inside, the home was designed to pull the landscape into daily life, with soaring ceilings and sun-filled living spaces oriented to the scenery from nearly every room. A dramatic, light-drenched great room anchors the layout, complemented by three fireplaces and a charming three-season screened porch. The fully finished walk-out lower level adds flexible space—also with views—while outside, a heated gunite pool, multiple entertaining areas, and an outdoor shower extend living into the open air. A two-car attached garage, high-speed internet, and a 1,000-bottle wine cellar complete the experience.

On a classic Beacon Hill address, this 3+ bedroom, 2 bath duplex pairs South Slope elegance with contemporary, industrial edge. A double-height living room with 18-foot ceilings sets a dramatic tone, amplified by oversized windows, polished concrete floors, and steel beam accents. A metal staircase stitches the levels together, while the layout balances spectacle with everyday comfort: an upper-floor sitting room, bedroom, and bath overlook the expansive main level, where the living room and den open to a charming enclosed patio. Two additional bedrooms and a bath sit to one side, while the opposite wing features a large dining room and an oversized kitchen. A private entry from the building’s enclosed courtyard—described as a hidden oasis—adds a welcome sense of arrival, with a common deck offering sweeping views and a live-in super.

Steps from the shoreline near Eagle’s Nest Bay, 104 Standish Street blends antique character with modern comfort in the heart of Duxbury. Sunlit rooms and hardwood floors set a warm, lived-in tone, while historic details nod to the home’s past. A 2009 renovation brought thoughtful updates to the kitchen, baths, and systems, creating an easy rhythm between everyday function and enduring elegance. With five bedrooms and three-and-a-half baths, the layout offers both spacious living areas and quieter private retreats, suited to busy mornings and slower weekends alike. Minutes from Duxbury’s town center and schools, the setting keeps daily errands close while preserving a sense of coastal calm. It’s a timeless place to settle in and enjoy the seasons as they change.