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Former Obama estate tops list of most expensive home sales in Mass. in 2025 — see top 3
These are the three most expensive homes sold in Massachusetts in 2025, according to MLS and Zillow data.
The saying goes “money talks, wealth whispers,” but the eye-popping homes — complete with eye-popping price tags — behind the biggest residential real estate transactions across Massachusetts in 2025 are talkers.
At a time when the $925,000 median sales price for a single-family home in Greater Boston already seems out of reach for many, this top trio is in a mortgage payment (or cash offer) league of their own.
As for the locations, the neighborhood backdrop to these transactions isn’t shocking: Martha’s Vineyard, Boston’s Back Bay, and Nantucket rule the roost. Here are the three priciest home sales in the Bay State in 2025, according to MLS and Zillow data.
41 Cobbs Hill Road, Chilmark, Martha’s Vineyard
Price: $37,000,000
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Sold: July 10, 2025
The crown jewel home of 2025 came with a presidential seal of approval alongside its $37 million price tag. Blue Heron Farm in Chilmark, better known as the former Summer White House for the Obama family, officially claimed the year’s top spot. Spanning nearly 30 acres on Tisbury Great Pond, this compound is a self-contained ecosystem of luxury, featuring a 150-year-old barn relocated from Pennsylvania.
Beyond eight bedrooms and a private beach, the ultimate flex is the Norman Foster-designed pool house — why shouldn’t your swim break come with ties to a Pritzker Prize-winning architect? Listed by Maggie Gold Seelig of MGS Group Real Estate, this sale confirms that privacy isn’t priceless — it can be acquired on the Vineyard for tens of millions of dollars.
59 Commonwealth Avenue, Boston
Price: $21,000,000
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Sold: Nov. 24, 2025
If you’ve ever walked down the French boulevard-inspired stretch of Commonwealth Avenue in the Back Bay and wondered who owns those entire townhouses, the most up-to-date answer is the new owner of Number 59. Fetching a cool $21 million in November, this “sunny side” (aka the southern-facing stretch) stunner on the “Gold Coast” between Berkeley and Clarendon Streets defies the Back Bay trend of chopping grand estates into condos — remaining a glorious, 11,300-square-foot single-family monolith.
With 8 bedrooms, 10 bathrooms (8 full and two half baths), elevator access to all floors, and an attached garage (a Back Bay rarity), it is the architectural equivalent of a unicorn. Also listed by Maggie Gold Seelig, who had a firm hand on eight-figure deals this year, this 1910 masterpiece includes a separate staff or guest apartment.
14 Lincoln Avenue, Nantucket
Price: $21,000,000
Sold: Jan. 7, 2025
Tying with our Back Bay entry for the silver medal at $21 million, this Nantucket compound proves that “The Cliff” is just as much its own tax bracket as it is a neighborhood. This restored 6-bedroom, 10-bathroom grand dame dating to 1908 was listed by Gary Winn of Maury People Sotheby’s and includes a separate guest house. The real showstopper, however, is the more-than-900-square-foot rooftop deck — allegedly the largest of any residential property on the island — offering 360-degree views that practically demand a champagne toast at sunset. Inside, the home features a secret study hidden behind a foyer panel, which is frankly the only rational place to hide when you have a full house of summer guests.
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