These are the highest-priced home sales reported in the Boston metro area for the week ending October 11, 2026, and together the five sold for $22.63 million. The list moves from a Back Bay condominium to suburban single-family homes south and west of the city, then up to the New Hampshire Seacoast region, where two of the five sales took place.
The group spans two centuries of building, from a home finished in the early 19th century to one completed in 2020. Four of the five are single-family homes. In two of the sales, the listing agent also represented the buyer.
No. 1 — $5,950,000 · 33 Commonwealth Ave #5, Boston, Massachusetts
The top sale was a condominium on the second block of Commonwealth Avenue in Back Bay, which sold for $5,950,000. The home occupies a full floor on the sunny side of the avenue, with direct elevator access and views out over the Commonwealth Avenue Mall.
Built in 1863, it keeps much of its original character: high ceilings, oversized windows, elaborate moldings and custom built-ins, along with wood floors and two fireplaces. All of its 3,109 square feet are on one level, with three bedrooms and three baths. The primary suite has two bathrooms, one of them with a concealed dressing room, and the home also has two private balconies. Parking comes with it, in the form of a deeded garage space and a deeded outdoor space. Newbury Street, the Charles River Esplanade and the Public Garden are all close by.
The condominium went under contract 15 days after it was listed and sold at its full asking price. Maggie Gold Seelig of MGS Group Real Estate LTD was the listing agent and also represented the buyer, so the same agent was on both sides of the sale.
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No. 2 — $5,005,000 · 32 Arlington Rd, Wellesley, Massachusetts
In Wellesley’s Country Club neighborhood, a renovated Colonial built in 1913 went under contract three days after it was listed. It sold for $5,005,000, which was $310,000 above its asking price of $4.695 million.
At 7,013 square feet, it has the largest living area of the five homes. There are six bedrooms and five bathrooms, four full and one half. The layout is open, joining formal rooms for entertaining with everyday family space, and the first floor has two custom-built offices. The home has four fireplaces, including ones in the living room, the family room and the primary bedroom, as well as a sunroom, a sitting room, a playroom, a mudroom and a wet bar.
The finished lower level adds a recreation room, an arts and crafts area and an au pair suite with a full bathroom next to it. A newer two-car garage also includes space for a gym and a loft. Outside, the level 0.39-acre lot is professionally landscaped and has a stone wall, a patio and a screened porch. The property last sold in 2013 for $2.425 million.
The Lara & Chelsea Collaborative of Coldwell Banker Realty – Wellesley listed the home and represented the buyer, working both sides of the sale.
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No. 3 — $4,375,000 · 75 Canton Ave, Milton, Massachusetts
The oldest home in this group dates to 1820. A Federal-style home on Milton Hill with a post-and-beam frame, it sold for $4,375,000 and sits on 0.94 acres close to Milton Village.
The home has been updated while keeping its architectural detail. It has seven bedrooms and eight bathrooms, five full and three half, the most of any home on the list, in 6,404 square feet. There are six fireplaces, a chef’s kitchen with a La Cornue range, both formal and casual living areas, a wet bar and a finished third floor. A newly completed one-bedroom accessory dwelling unit gives the property a guest house that could also serve as an office or quarters for an au pair or extended family. The four-car garage is the largest among the five sales.
The grounds are fenced and professionally landscaped. A heated inground pool is joined by a pergola, a wraparound deck and a covered patio. Milton Academy is within a few minutes. The property last sold in 2012 for $1.3 million.
The home went under contract 24 days after it was listed. Sarah Glovsky of The Charles Realty and Andrew Glovsky were the listing agents, and Beth Rooney of eXp Realty LLC – Corporate Office represented the buyer.
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No. 4 — $4,100,000 · 74 Saddle Trail Drive, Dover, New Hampshire
Where Fresh Creek meets the Cocheco River in Dover, New Hampshire, a shingle-style home designed by Fiorentino sold for $4,100,000. It stands on 3.60 acres on Saddle Trail Drive, and a private dock gives it a route by water to New Hampshire’s inland coast and on to the Atlantic.
The land is as much a part of the property as the home. There is a heated saltwater pool with an integrated spa and a Pebble Tec finish, a gas firepit facing west toward the sunset and a garden. Down at the water’s edge, a campsite has its own wood-burning firepit along with water and electric service. The lot was planned in advance for a carriage house or a barn with living quarters.
Built in 2009, the two-story home has five bedrooms and five bathrooms, three full and two half, in 5,247 square feet. Cabinetry and built-ins are by Jewett Farms, the kitchen has Sub-Zero and Wolf appliances, and the floors are red birch. Two wood-burning fireplaces anchor the main rooms. The plan includes a three-season sunroom, formal and casual dining spaces, an executive office suite and a recreation room with a wet bar that opens to a covered balcony. A heated three-car garage has a dog wash. Cochecho Country Club, Berwick Academy and downtown Portsmouth are each a few minutes away. The property last sold in 2021 for $2.8 million.
Jamieson Duston of Duston Leddy Real Estate was the listing agent, and John Lonborg of LandVest / Christie’s International Real Estate represented the buyer.
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No. 5 — $3,200,000 · 741 Ocean Boulevard, Hampton, New Hampshire
The newest home on the list sits directly on the ocean in Hampton, New Hampshire, with the sand a few steps from the door. The contemporary home on Ocean Boulevard was completed in 2020 and sold for $3,200,000.
It rises three stories on a 3,485-square-foot corner lot, and an elevator runs from the basement to the top floor. The main living level is oriented toward the Atlantic, with the kitchen, dining area and living room in one open space. The kitchen has Thermador appliances, two dishwashers, quartz counters and bar seating, and a butler’s pantry beside it adds wine and beverage refrigeration and a cocktail sink. That level opens to a covered Azek deck with glass railings and a built-in summer kitchen.
The primary suite takes the top level, with a walk-in closet and a bath that has a Kohler steam shower. A family room on the same floor opens to an upper deck facing the ocean. The other two bedrooms are on the first level, and in all the home has three bedrooms and three baths in 3,612 square feet. A heated one-car garage and an outdoor shower complete it. The property last sold in 2021 for $2.15 million.
It went under contract two days after it was listed and sold at its full asking price. Lauren Stone of Carey Giampa, LLC/Rye was the listing agent, and Nick Ponte of Carey Giampa, LLC/Portsmouth represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 11, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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