Real Estate

The Five Most Expensive Homes in Massachusetts

Looking for a grandiose new home? Here are a handful of the most expensive homes on the market.

Are you looking for a new home? Or maybe you just like looking at luxurious houses? Take a look at these fives homes currently listed on Zillow.com as the most expensive standalone houses — not including buildable lots, homes with buildable land, condos or commercial structures — in Massachusetts:


97 Tilipi Run St., Chatham — $25 million: With more bathrooms (10) than bedrooms (6), this 10,974-square-foot home is set on 1.9 acres on the Cape Cod shore at Monomoy Islands and Nantucket Sound. The shingle-clad house was built in 2010 and has a banquet-sized dining room, a chef’s kitchen, an 11-seat theatre and a circular one-bedroom carriage house on the property.


30 Orange St., Nantucket — $20 million: Called “Long Hill,” this house has eight bedrooms and 10 bathrooms in a 7,211-square-foot home on a .29-acre lot in Nantucket. The house, along with its formal English garden, is on a historic street and has a view of Nantucket Harbor, Coatue and the town.  

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13 Squam Road, Nantucket — $19.9 million: Described as an “oceanfront, private compound,” this 2.2-acre lot has a main house, a pool, a cabana, decks, a gas firepit, lawn, gardens and a private boardwalk that leads to Squam beach. The main living area is a 10,682-square-foot house with eight bedrooms and eight bathrooms.  


157 Wapoos Trail, Chatham — $18 million: This is 13-plus acres of tranquility on Morris Island in Chatham, which includes a 7,500-square-foot main house built in 1960, a boathouse, a dock, a small chapel, a “child’s retreat” and a garden shed. The main house contains five bedrooms, a formal dining room, a circular staircase, a library, a sunroom, a third-floor craft room, a billiard room, seven fireplaces and eight bathrooms.

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68 & 72 Monomoy Road, Monomoy — $17.95 million: Built in 1954, this home has not been on the market in over 50 years. The seven-bedroom, six-bathroom house sits on a 1.18-acre lot and has a view of Nantucket Harbor, Nantucket Sound and the town, as well as access to a private beach.

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