Photo courtesy of the Nantucket assessor's office
Another week, another blockbuster sale in Nantucket’s Cliff neighborhood in this week’s roundup of Massachusetts’ most expensive home sales. The Nantucket Current reports that the sale was “intra-family” but it fits a pattern of very nearly record-breaking sales in that neighborhood. The most expensive residential sale on record in Massachusetts is 68 and 72 Monomoy Road, which sold to Barstool Sports owner Dave Portnoy in the fall of 2023 for $42 million.
Prices, sale dates and ownership information sourced from The Warren Group, publisher of Banker & Tradesman. Listing agent information sourced from MLS. Property size sourced from public records. Homes represent the most expensive single-family and residential condominium transactions for Oct. 4-10, 2025.
1) 3 Sherburne Way, Nantucket
Price: $37,750,000
Buyer: 3 Sherburne Way NT
Seller: Cliffside 2 LLC
Agent: Not Sold via MLS
Size: 4,626 square feet on 2.39 acres
Sold: 10/8/2025
2) 55 Fayerweather St., Cambridge
Price: $15,750,000
Buyer: FW 55 RT
Seller: Fayerweather 55 NT
Agent: Unknown agent
Size: 5,139 square feet on 0.2 acres
Sold: 10/8/2025
3) 15 Pleasant St., Nantucket
Price: $15,450,000
Buyer: 15 Plesant LLC
Seller: Cavu Pleasant LLC
Agent: Peter Engen, Lee Real Estate
Size: 4,973 square feet on 0.24 acres
Sold: 10/6/2025
4) 3 Tautemo Way, Nantucket
Price: $7,875,000
Buyer: Three Tautemo Way RT
Seller: Jonathan A. Jacoby and Suzanne L. Jacoby
Agent: Chris Kling, J Pepper Frazier Co.
Size: 3,381 square feet on 0.46 acres
Sold: 10/7/2025
5) 15 Byron St., Boston
Price: $6,200,000
Buyer: Eric A. Stein and Lauren K. Stein
Seller: PCJ Chatham Holdings LLC
Agent: Not Sold via MLS
Size: 3,396 square feet
Sold: 10/09/2025
