They say real estate tells the story of a place — and nowhere is that more true than Massachusetts. From windswept island estates and presidential retreats to historic Gilded Age mansions and gleaming modern penthouses, the Bay State is home to some of the most extraordinary properties in the world.
I’m Chris, Managing Broker at Remmes & Co., and today I’m taking you inside the ten most expensive homes ever sold in Massachusetts — counting down from #10 to #1. These aren’t just houses. They’re architectural masterpieces and cultural landmarks that capture the essence of New England luxury.
10. 187 Penzance Road, Woods Hole — $20,000,000
We begin our countdown in the coastal village of Woods Hole with a quintessential Cape Cod retreat. Perched on nearly 10 acres of pristine waterfront, 187 Penzance Road is the definition of classic New England living.
The estate features a main residence with panoramic harbor views, a two-bedroom guesthouse, pool, boathouse, deepwater dock, and two private beaches. Inside, chestnut-paneled libraries, French doors, and a sunroom create timeless elegance. Outside, the Atlantic stretches endlessly before you — a daily reminder of Cape Cod’s enduring allure.
9. The Chimneys, 195 Summer Street, Manchester-by-the-Sea — $20,000,000
Heading north to the North Shore, The Chimneys is a Georgian masterpiece set atop a bluff on 28 private acres. At 13,000 square feet, the home feels like something from a novel — complete with 12 fireplaces, hand-painted Chinese wallpaper, and a mahogany dressing room.
Nearly every room offers sweeping views of the Atlantic, and outside, a restored 1906 Olmsted garden and a private beach shared by just seven families make this property feel more like a sanctuary than a residence.
8. 150 Seaport Boulevard, Boston — $20,348,000
From classic estates to sleek city living, 150 Seaport Boulevard is a record-setting condominium in Boston’s Seaport District. This 5,525-square-foot residence merges two units into one palatial home, complete with Italian cabinetry, Sherle Wagner fixtures, and panoramic harbor views.
With five-star St. Regis amenities — including a spa, pool, fitness center, and private lounge — this home offers a lifestyle that feels more like a luxury resort than a condominium.
7. Penthouse PH2E, 776 Boylston Street, Boston — $21,500,000
At number seven, we rise above the Back Bay skyline. Penthouse PH2E at the Mandarin Oriental is one of Boston’s most exclusive addresses. Floating 15 stories above the city, this 7,000-square-foot residence offers 360° views of Boston, Cambridge, and the Charles River.
With two chef’s kitchens, a grand reception hall, bar lounge, and multiple terraces, it’s designed for entertaining on a grand scale. Combine that with five-star hotel services, and you have the pinnacle of urban luxury.
6. 835 Sea View Avenue, Osterville — $22,750,000
Few homes capture the spirit of Cape Cod’s oceanfront lifestyle like 835 Sea View Avenue. Set on 3.66 acres with 280 feet of private sandy beach, the estate features seven en suite bedrooms, a wine cellar, gym, golf simulator, and resort-style pool.
Every room is designed to maximize sweeping views of Nantucket Sound, and every detail reflects coastal luxury at its finest.
5. 150 Woodland Road, Brookline — $23,000,000
Luxury isn’t limited to the coast. At 150 Woodland Road in Brookline, Old World craftsmanship meets modern sophistication in a 27,000-square-foot limestone estate.
Situated on over seven gated acres, the property includes eight fireplaces, a grand library, an elevator, and meticulously manicured grounds. It’s one of New England’s most impressive estates — and a reminder that extraordinary living extends far beyond the shoreline.
4. Swain’s Neck, 260 Polpis Road, Nantucket — $25,000,000
At number four, we return to the island of Nantucket for Swain’s Neck, a 63-acre waterfront estate perched on a private peninsula. Offering unmatched seclusion and panoramic harbor views, the property includes a main residence inspired by Nantucket’s Quaker and whaling heritage, as well as a guest cottage, studio, boathouse, and two moorings.
This isn’t just a vacation home — it’s one of the island’s most exclusive family retreats.
3. 41 Jefferson Avenue, Nantucket — $26,000,000
Once a 1930s beach club, 41 Jefferson Avenue has transformed into one of Nantucket’s most unique and valuable properties. The nearly one-acre resort compound features a four-unit main house, two standalone cottages, and rare residential-commercial zoning.
Whether envisioned as a private estate, boutique hotel, or exclusive beach club, its potential is as remarkable as its beachfront location.
2. Blue Heron Farm, Martha’s Vineyard — $37,000,000
Coming in at number two is Blue Heron Farm, a property steeped in presidential history. Once the summer retreat of President Barack Obama, this nearly 30-acre estate in Chilmark is the epitome of Vineyard luxury.
Highlights include a Norman Foster-designed pool house, equestrian paddocks, guest residences, and a private beach. Surrounded by farmland and framed by Tisbury Great Pond, Blue Heron Farm is as serene as it is significant.
1. Beam Ends, Nantucket — $38,127,000
And finally, the crown jewel — Beam Ends, the most expensive property ever sold in Massachusetts.
Set on nearly four acres surrounded by conservation land, this waterfront compound offers total privacy and direct beach access. The main residence, built in 2008, is complemented by two guest cottages — one dating back to 1910 — and over 15,000 square feet of exquisite living space. From sunrise over the harbor to sunset over the creeks, Beam Ends isn’t just a home. It’s a world unto itself.
A Testament to Craftsmanship and Ambition
These ten remarkable properties are more than just real estate transactions — they’re chapters in the story of Massachusetts itself. Each one reflects the region’s unique blend of history, natural beauty, and architectural ambition.
And as each record is broken, one thing becomes clear: in Massachusetts, luxury has no limits — and the next chapter is still waiting to be written.