5 Exceptional Massachusetts Luxury Homes from Nantucket to Lexington

Set on nearly a full acre in Surfside, 121 Surfside Road offers the rare ease of a true Nantucket compound less than a mile from Surfside Beach and The Surf snack shack. The main house is arranged for year-round or seasonal living with three bedrooms and two and a half baths, while a separate guest house provides added privacy with one bedroom and two full bathrooms—ideal for visitors or use as a standalone rental. A garage with a studio apartment and full bath extends the possibilities further, whether for additional income, caretaker quarters, or a dedicated creative workspace. With three distinct living spaces on one spacious lot, the property is thoughtfully suited to multigenerational living, a private island retreat, or flexible long- and short-term rental use. Life here is defined by space, independence, and beach days close at hand.

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Along the edge of Nantucket Sound, this meticulously crafted new build on Oyster Pond Road pairs a light-filled, airy ambiance with a layout designed for both entertaining and quiet retreat. Multiple decks extend the living space outdoors, framing sweeping water views for al fresco dinners or slow mornings with sea air and coastal birds in sight. Inside, hosting feels effortless with a full wet bar, strategically placed beverage fridges, two full-size refrigerators, and a dedicated wine cellar room. Daily life is equally considered, with two laundry rooms and four and a half baths. The primary suite reads like a private sanctuary, featuring two expansive walk-in closets, a lounge area, and a luxurious en suite bath. A formal living and dining room, breakfast bar, game room, den, office, and separate study round out the spaces. Outside, an extra-large two-car garage with storage systems and a spacious shed keep everything neatly tucked away, leaving more time for beaches, the bike path, and in-town Falmouth.

Surrounded by six acres with a one-acre lawn and conservation land beyond, this architect-designed residence in Lincoln balances serene scale with everyday practicality. Built in 2008, it spans 15 rooms with 5+ bedrooms and 6 baths, supported by a 3-car garage, radiant in-floor heating, fresh-air exchange, and energy-efficient 2×6 construction with icynene insulation. The interiors lean quietly distinctive: an authentic tearoom, a Japanese bath, glass shoji doors, and a sunken-table great room. Quarter-sawn oak and bamboo floors pair with a cherrywood kitchen, while windows on two sides of every room invite steady natural light. Indoor and outdoor fireplaces, balconies, and a stone patio extend the living spaces into the landscape. An in-law/au pair suite with its own kitchen, living room, bedroom, and two baths offers flexibility, with a reserve generator supporting key areas as days unfold.

Tucked into Lexington’s desirable Sun Valley neighborhood, this new construction contemporary home pairs high efficiency with a quiet setting abutting the Whipple Hill conservation area. The open-concept chef’s kitchen is built for everyday ease and weekend hosting, with premium appliances, a huge quartz breakfast-bar island, a butler’s pantry, and sleek custom cabinetry. Nearby, an impressive family room is framed by vast windows and anchored by a modern gas fireplace, opening seamlessly to the wraparound deck and yard beyond. Upstairs, the primary suite delivers a true retreat with a huge walk-in closet, dual vanities, a tiled shower, and a soaking tub. A third-level teen/guest suite adds a bedroom, playroom, and bath, while the finished lower level offers a family room, theater, plus an additional bedroom and full bathroom—ideal for unwinding at home.

From its elevated Hill Street address in Lexington, this new construction residence pairs an open-concept layout with a crisp, contemporary point of view. Chic living spaces are finished with impressive millwork and designer details, while the chef’s kitchen anchors daily life with premium appliances, a generous breakfast-bar island, butler’s pantry, and a wine closet—flowing seamlessly into the dining room for easy entertaining. In the family room, a coffered ceiling and fireplace set a warm tone, with views out to a stone patio and private backyard beyond. A main-level office and guest suite add flexibility for work and visitors. The primary suite is a true retreat, offering a huge walk-in closet, dual-sink vanity, tiled oversized shower, and soaking tub. Downstairs, a recreation room, wet bar, media room, and bedroom suite create a dedicated space to unwind.