The second home in this week’s roundup of Massachusetts’ most expensive home sales comes with the opportunity to get a new neighbor. The huge plot just across from Nantucket’s Tuppancy Links has the potential to be subdivided to add a second home with a pool and outbuildings, as suggested in a September 2024 listing that was subsequently taken down.

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. Property size sourced from public records. Homes represent the most expensive single-family and residential condominium transactions for June 9-17, 2025.

1) 552 Shore Road, Chatham

Price: $11,250,000
Buyer: Judith Gibbons and Francesco Scattone
Seller: Upland Road LT
Agent: Paul E. Grover, BHHS Robert Paul Properties
Size: 5,868 square feet on 2.86 acres
Sold: 6/9/2025

2) 166 Cliff Road, Nantucket

Price: $10,050,000
Buyer: Rockefeller T
Seller: Charles A Ernst III RT
Agent: Lucie Cristler, Maury People Sotheby’s
Size: 3,217 square feet on 1.99 acres
Sold: 6/12/2025

3) 749 South Main St., Centerville

Price: $6,500,000
Buyer: 749 Sandcastle LLC
Seller: Sandcastle Family Holdings LLC
Agent: Katie Clancy, William Raveis Real Estate
Size: 8,834 square feet on 1.79 acres
Sold: 6/12/2025

4) 119 Belle Lane, Needham

Price: $6,200,000
Buyer: Kristen E Webber RET
Seller: 119 Belle Lane RT
Agent: Not listed on MLS
Size: 8,236 square feet on 1 acre
Sold: 6/13/2025

5) 32 Bowdoin St., Cambridge

Price: $5,600,000
Buyer: Cecilia A. Cordeiro and Eduardo E. Cordeiro
Seller: Peter W. Choo and Stephanie S. Choo
Agent: John O’Neil, Lauren Segal and Lauren Holleran, Gibson Sotheby’s
Size: 4,748 square feet on 0.12 acres
Sold: 6/10/2025