The list of Massachusetts’ most expensive single-family and condominium sales of 2022 is very nearly a list of Nantucket’s most expensive home sales of 2022, despite numerous notable transactions involving Boston’s new luxury towers and high-end historic homes last year.

Address: 21 Lincoln Ave., Nantucket
Price: $36,000,000
Buyer: Nantucket Re Invest LLC
Seller: 21 Lincoln Avenue NT
Size: 6,655 square feet on 1.22 acres
Sold: 4/15/2022

The most expensive single-family sale in Nantucket history takes the top spot in this year’s home sales. The 4,903-square-foot main house, built in 1878, and the 1,752-square-foot, 2013-vintage outbuilding sit on 1.22 acres. The property appears to have been substantially renovated after its most recent sale, for $14.02 million in 2012. An off-market transaction, the buyer of the house just over a half-mile from the island’s village center was a Texas LLC.

Address: 63 and 63 ½ Hulbert Ave., Nantucket
Price: $33,000,000
Buyer: 63 Hulbert LLC
Seller: Leigh Q. Failing QPRT and 63 Hulbert Avenue RT
Size: 5,075 square feet on 0.48 acres
Agent: Jeanne Hicks, Lee Real Estate
Sold: 10/3/2022

Second only to a $36 million sale in Nantucket’s Cliff section earlier this year, and ahead of Red Sox owner John Henry’s newly purchased $25 million island estate, this waterfront home on Hulbert Avenue is surprisingly demure for its price. The listing noted only a “recently renovated chef’s kitchen,” dual master suites and a two-bedroom guest house.

Photo courtesy of Maury People Sotheby’s International RealtyAddress: 4 Middle Valley Road, Nantucket
Price: $25,000,000
Buyer: Harbor Hill House LLC
Seller: 4 MVR LLC
Size: 18,012 square feet on 4 acres
Agent: Maury People Sotheby’s International Realty
Sold: 4/22/2022

Boston Red Sox owner John Henry bought this estate through an LLC, and what a purchase he made. The unique, nearly new home plays on classic Nantucket forms with decidedly contemporary architecture designed by Hugh Newell Jacobsen and Simon Jacobsen. It sits on piece of harbor-side high ground and boasts steps down to the sea and “gathering areas for every time of day and season” across several interconnected buildings.

Address: 7 Chase Links Circle, Nantucket
Price: $20,500,000
Buyer: 7 Chase Links LLC
Seller: Worth the Wait NT
Size: 8,530 square feet on 2.1 acres
Agent: Alexandra Coleman Eldridge, Great Point Properties
Sold: 11/9/2022

Built in 2016 and designed by local architects Botticelli & Pohl, it sits on high ground overlooking a salt marsh and Nantucket Sound. A studio guest unit, half a basketball court and a swimming pool round out the property.

Address: 5 Grant Ave., Nantucket
Price: $19,900,000
Buyer: Goldeneye LLC
Seller: Ceruzzi Louis L Jr Est
Size: 6,002 square feet on 0.41 acres
Agent: Michael O’Mara, BHHS Island Properties
Sold: 11/18/2022
This home looks out from top of Nantucket’s Cliff in the exclusive Lincoln Circle. At $3,315 per square foot, what do its new owners get? No gracious, Gilded-Age-esque front yard like nearby 45 Cliff Road (sold for $3,062 per square foot in 2020), but similar views and the two-bedroom guest house and lush garden give them plenty of privacy not far from both beach and town.

Address: 159 Main St., Osterville
Price: $18,500,000
Buyer: Chapin 2 RT
Seller: 159 Main Street T
Size: 10,027 square feet on 6.11 acres
Agent: Robert Kinlin, BHHS Robert Paul Properties
Sold: 9/15/2022

Big vistas looking out on Nantucket Sound are the big draw at this house. The listing also advertised smart-home features, vaulted ceilings in many rooms and custom Travertine marble flooring in the master bath.

Address: 41 Hulbert Ave., Nantucket
Price: $17,600,000
Buyer: 41 Hulbert LLC
Seller: Jebel LLC
Size: 5,390 square feet on 0.25 acres
Agent: Robert Young, William Raveis Nantucket
Sold: 5/12/2022

Enter this home near the heart of Nantucket through a private garden. In total, it and its guest cottage – a converted boathouse – can sleep up to 11 connoisseurs of the island’s July 4th fireworks, which are easily visible from its harborside perch.

Address: 16 Marlborough St., Boston
Price: $16,286,000
Buyer: Jatoba LLC
Seller: Shs Holdings LLC
Size: 6,207 square feet
Sold: 12/27/2022

Not much is publicly available about this property, traded in an off-market sale. Listings for previous sales claim it was built in 1865, making it one of the Back Bay’s earliest homes.

Address: 32 Highland St., Cambridge
Price: $16,025,000
Buyer: Jeneric RT
Seller: Amos Third Corner LLC
Size: 4,828 square feet on 0.35 acres
Sold: 8/9/2022

Another off-market transaction, this early 1900s home appears to have been heavily renovated before its sale in August 2022.

Address: 251 Green Dunes Drive, Centerville
Price: $15,948,246
Buyer: Bank of America, N.A.
Seller: Sheila K RT
Size:
9,679 square feet on 8.93 acres
Sold:
8/24/2022

Built in 1995, this home was sold to mortgage-holder Bank of America, who sold it later in the year for $10.5 million to an LLC controlled by Ward J. Fitzgerald III, a Philadelphia-area real estate investment manager and prominent member of several Catholic organizations.

Meet Massachusetts’ Most Expensive Homes of 2022

by James Sanna time to read: 3 min
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