Photo courtesy of Sandpiper Realty
The second house in this week’s roundup of Massachusetts’ most expensive home sales hides a lot of house behind an unassuming facade. The main thing anyone passing by sees is a little cottage pushed up close to the sidewalk, a garage and a white picket fence. But go through the gate in that fence and a huge house opens up to you. Its most impressive feature is probably the double-height living areas, connected to a heavily-screened patio and pool by a sliding set of doors that run almost the full width of the living room.
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 Sept. 19-25, 2026. The home or homes described in the introduction are selected purely for their news value or aesthetic considerations.
1) 150 East Chop Drive, Oak Bluffs
Price: $8,300,000
Buyer: Jennifer Ellis Cox and Robert Cox
Seller: Gretchen Massey and Paul Massey
Agent: Andrew McElhinney, Compass
Size: 6,672 square feet on 0.64 acres
Sold: 9/22/2026
2) 43 Peases Point Way South, Edgartown
Price: $8,175,000
Buyer: 43Ppws LLC
Seller: Ppws LLC
Agent: Katie Donahue and Rachel Serwa, Sandpiper Realty
Size: 3,182 square feet on 0.24 acres
Sold: 9/23/2026
3) 198 Hummock Pond Road, Nantucket
Price: $7,400,000
Buyer: Birch Family Investments LLC
Seller: 198 HP LLC
Agent: Unknown / Not sold via MLS
Size: 2,120 square feet on 2 acres
Sold: 9/22/2026
4) 3 Pleasant St., Nantucket
Price: $7,240,000
Buyer: David S. Goldman
Seller: 3 Pleasant St NT
Agent: David Slick and Robin Slick, William Raveis Real Estate
Size: 2,707 square feet on 0.14 acrs
Sold: 9/25/2026
5) 26 Harbor Hill Road, Chilmark
Price: $7,000,000
Buyer: Owen Lynn T
Seller: Trust for the Benefit of Elizabeth Blair Kenney and Trust for the Benefit of Kristen Brock Kenney
Agent: Robert Kenney, Tea Lane Associates
Size: 1,548 square feet on 0.3 acres
Sold: 9/24/2026
