Photo courtesy of BHHS Robert Paul Properties
The first and last entries in this week’s roundup of Massachusetts’ most expensive home sales sit on two of Cape Cod’s many winding inlets. Both have easy access to the water, both are built in a contemporary style and both have soaring common areas. The biggest difference is in build date: The Chatham home was erected in 2020 and designed by Salt Architecture, while the other was delivered in 2000. Its listing description did not name the architect.
How we make the Gossip Report
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 solely the most expensive single-family and residential condominium closed sales for Oct. 3-9, 2026. The home or homes described in the introduction are selected purely for their news value or aesthetic considerations.
1) 301 Whidah Road, Chatham
Price: $11,850,000
Buyer: North Chatham Gulch RT
Seller: 301 Whidam Rd RT
Agent: Paul E. Grover, BHHS Robert Paul Properties
Size: 5,008 square feet on 0.92 acres
Sold: 10/5/2026
2) 43 Vestal St., Nantucket
Price: $7,300,000
Buyer: 43 Vestal LLC
Seller: High Tide Homes LLC
Agent: Brian Sullivan, Fisher Real Estate
Size: 2,954 square feet on 0.46 acres
Sold: 10/5/2026
3) 31-33 Commonwealth Ave. #5, Boston
Price: $5,950,000
Buyer: Courtney Dickinson and David Greyzel
Seller: Topol LLC
Agent: Maggie Gold Seelig, MGS Group Real Estate
Size: 3,002 square feet
Sold: 10/5/2026
4) 385 Barnes Road, Oak Bluffs
Price: $5,208,000
Buyer: D2SM Global LLC
Seller: 385 Barnes Road LLC
Agent: Stephanie Roache, Donnelly + Co.
Size: 3,608 square feet on 0.98 acres
Sold: 10/5/2026
5) 476 Baxters Neck Road, Marstons Mills
Price: $4,150,000
Buyer: Sullivans Island Partners LLC
Seller: Evryklia Abodeely RET
Agent: Livia Freitas Monteforte and Jessica Nolan, Compass
Size: 4,252 square feet on 2.09 acres
Sold: 10/9/2026
