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By Eileen Woods
From a secluded family compound in North Chatham to Boylston Street penthouses, buyers paid top dollar for pretty spectacular properties.
It’s expected that the Cape, Boston, and Nantucket would dominate the priciest sales list — some streets make more than one apparently — but Martha’s Vineyard, a playland for the rich and powerful, didn’t crack the top 10.
These were the top 12 home sales of 2024, according to The Warren Group, a data analytics firm, and The Boston Globe:

The 10-bed, 11-bath beachfront compound at 41 Jefferson Ave. on Nantucket originally went on the market for $39,000,000, according to Globe writer Emily Sweeney. It was sold to the Nantucket Land Bank, “and the plan is to turn the property into a public beach.”

The most expensive home sale in Massachusetts in 2024 was Penthouse 2E at 776 Boylston St. in Boston, at the Mandarin Oriental. The four-bedroom, 4.5- bath condo features floor-to-ceiling windows on all four sides, 6,929 square feet of living space, and multiple terraces. A writeup by luxury realtor Tracy Campion noted “its stunning floor plan incorporates an expansive central reception hall, opulent living and dining rooms, custom gourmet kitchen with deck and separate chef’s kitchen, utterly magnificent bar/lounge area with terrace, and comfortable family room, all of which are dedicated to entertaining on a grand scale.” It sold in October.
This honor goes to 42 Shimmo Pond Road in Nantucket, or “Little Shimmo,” a 1.25-acre estate that dates to 1928 and offers seven bedrooms with water views, 7.5 bathrooms, and a 400-foot private dock. The write-up by Greg McKechnie at Great Point Properties promises that the “generously proportioned living spaces are artfully designed to foster connection and conviviality, providing the ideal setting for cherished gatherings with family and friends.” It sold in June.
Unit A at 150 Seaport Blvd. in the city’s tony Seaport District sold in October. The two-story condo comes with six bedrooms, eight full baths, and two half baths. It clocks in at a whopping 10,005 square feet.



Boston.com’s Beth Treffeisen reported in June that the sale of 835 Sea View Ave. in Barnstable set a record for the highest-priced real estate transaction ever recorded for a Cape Cod residential property. Ryan Castle, the CEO of the Cape Cod & Islands Association of Realtors, confirmed that this was the largest sale ever recorded on the Multiple Listing Service in Barnstable County, which makes up Cape Cod. The home is in the village of Osterville.
The buyer was James Langway of Rhode Island, who owns and operates several Toyota dealerships in Vermont and Rhode Island. The property was last sold in 2011 for $4.5 million to Amin Khoury, a prominent entrepreneur in medical products, aerospace manufacturing, and oilfield services.
“It’s a beautiful piece of property,” said Paul Grover of Berkshire Hathaway HomeServices Robert Paul Properties, the broker for the sale. “Sea View Avenue is probably one of the most beautiful streets on the Cape and certainly is in Osterville. It’s really quintessential Cape houses with fences and roses and some large estates overlooking the ocean.”
The property has seven bedrooms and 14 baths and sits on 3.66 acres. On a good day, Grover said, one can see Martha’s Vineyard.
The Mandarin Oriental at 776 Boylston St., makes the list again, with Unit E12A, a two-bedroom, three-bath, 4,174-square-foot condo, according to Realtor.com.
The estate at 13 Washing Pond Road on Nantucket sold in June. The write-up by the listing agent, Chandra Miller of Maury People Sotheby’s International Realty, noted that the 2-acre property in the Cliff Road neighborhood is “the ultimate serene setting to unwind and enjoy the beautiful surroundings.” The main house has five bedrooms and six baths, while the detached two-car garage includes two guest suites, two full baths, and two galley kitchenettes.
The four-bedroom single-family home at 279 Marlborough St. in the Back Bay sold in October and features walls of glass, a top-floor terrace with an outdoor fireplace, flooring with radiant heat, an attached garage with parking for two vehicles, electric car charging, an elevator, and heated walkways. Nicholas Mattia at Luxury Residential Group LLC was the listing agent, according to Zillow.com.
This new-build 19-room state at 218 Cliff Road on Nantucket sits on 1.84 acres and has seven bedrooms, seven full baths, and two half baths. It came with a guest cottage, a pool, and the furnishings. The write-up by Fisher Real Estate notes that “the inviting front foyer boasts a custom white oak feature wall, setting the stage for the interior aesthetic — a blend of natural materials that complement the property’s island setting.
Take a virtual tour of the property.
The five-bedroom, seven-bath property at 28 Shimmo Pond Road on Nantucket has a “water view like no other,” wrote the listing agent, Michele Lindstedt of Great Point Properties. “Elevated high on the lot, the main house was designed to take in the expansive views through its perfect window placement. The home is surrounded by rock walls and some of the most impressive perennial gardens that create a vibrant color palette all summer long.” It sold in August.

Originally listed for $18,800,000 in March 2022, the property at 108 Cotchpinicut Road in North Chatham known as “High Scatteree” sold in June.
“The nine-bed, nine-bath estate (seven full, two half) was built as a summer home for the Leeds family of Philadelphia in 1940 in the style of Chatham’s older captain’s houses,” correspondent Megan Johnson wrote for Boston.com. “Set high on a bluff above Pleasant Bay, the estate is located up a long, winding driveway surrounded by meticulously landscaped grounds. The seven-bedroom main house is filled with unique spaces, like the shore room, an addition to the original structure, which is filled with oversized windows. … A central octagonal belvedere and roof deck provide a tremendous 360-degree view of the estate.
“A two-bed, two-bath guest house opens to a rolling lawn, clay tennis court, and impeccable gardens, where the owners, who were avid gardeners, labeled every specimen with a plaque.”

The estate at 144 Plantingfield Way in Edgartown “offers unobstructed views of Edgartown’s outer harbor” and dates to 1920, according to rental write-up by LandVest. The Martha’s Vineyard property offers eight bedrooms, four full baths, two half baths, and multiple sitting rooms and includes a guest house on its 1.5 acres. It sold in December.
Unit 5701 at 1 Dalton St. in the Back Bay has three bedrooms and three baths in 3,696 square feet. It sold in March. At this address, the Four Seasons Hotel and Private Residences, and all the luxury and services that entails. This unit sold in March.
Eileen McEleney Woods is the real estate editor for Boston.com and editor of the Boston Globe's Sunday real estate section (Address).
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