Massachusetts leads the list of Most Expensive Homes for Sale in New England this month with a house in Brookline (pictured above). Situated between the Brookline Country Club and the Putterham Meadow Golf Course, this house is its own wooded island. It sits on over 13 arches of woodland that create a dazzling tapestry of ponds, rolling lawns, sculpted rock outcropings, and a horticultural encyclopedia of plantings. Just five miles from central Boston, this house combines the best of city accessibility with the tranquility of a truly private residence. The home itself boasts 26,623 square feet of living space broken down in to 24 rooms, 8 bedrooms, seven full bathrooms, and five half baths. There are also eight fireplaces and parking enough for up to 20 guests. All this for $90,000,000 Have a look at the listing.


Connecticut takes second place with a home priced at $39,950,000. Round Hill Manor is located in fashionable Greenwich and is well-deserving of the “manor” title. It sits on the crest of a plateau, nestled in more than 40 open, rolling acres that offer panoramic views of Long Island Sound. The grounds are graced with majestic specimen trees, old stone walls, and rolling lawns. Inside you’ll find spacious rooms with exquisite detailing, lovely floors, tasteful paneling, and banks upon banks of windows. With nine bedrooms, eight full bathrooms and four half baths, and over 17,000 square feet of living space, this house is truly an estate. Take a look here.


New Hampshire


Coming in third is this $19,800,000 house on the shores of Lake Winnipesaukee. Built in the style of the luxurious mansions of Newport, RI, this house is ideal for anyone who loves the privacy and tranquility of the lakefront. At 63,029 feet, this single family boasts twelve bedrooms and no fewer than 24 bathrooms. With boat houses, manicured landscaping, views of the White Mountains, and over 10 acres of land, there are too many features to mention in this short article. Explore it for yourself here.


There was a day when Bar Harbor, ME, rivaled Newport, RI, as the ideal vacation spot for the likes of Rockefeller and Carnegie. This 15,000  square foot home is a legacy of that era. With eight bedrooms and ten full bathrooms, this jewel of a house overlooks the ocean. Built in 1907, this home retains the original grandeur of the time when Bar Harbor was a playground for the rich and famous. Take a peak.

Rhode Island

Rhode Island has two homes for sale at $12,500,000, one in Westerly and one in Newport, earning them both fifth place on this list. The Westerly home comes with six bedrooms, three and one half baths, and gorgeous oceanfront views, but it is the Newport home that truly stuns.

The Newport home was built in 2012 and has six bedrooms and five and one half bathrooms. Know as “the Bird House,” this home is state-of-the-art in every respect, from geothermal heating and cooling to top-of-the line amenities. Tischler custom windows and doors, three-stop elevator, radiant heated floors, 3-phase 400-amp electrical service, whole house generator, and exquisite landscaping all add to the sense of ultra-modern elegance. Take a look at the Westerly home and the Newport home.


Last but certainly not least is this picture-perfect 200 acre farm in Woodstock, VT. Listed at $9,250,000, this house was designed by internationally renowned architect Rick Joy. Woodstock Farm is a dramatic shingle and stone house and barn set on more than 200 arces of Vermont countryside. The high concept contemporary design is a superb re-imagining of the visual vernacular of the rural northeast. The main residence offers a 152-foot elongated gable house with massive end walls of Lake Champlain bedrock and cedar cladding on the roof and side walls. The property itself includes a deep, spring-fed swimming pond, rolling pastureland, and mixed northern hardwood forests. Take a look here.