Photo courtesy of Compass

The second home in this week’s roundup of Massachusetts most expensive home sales comes with sweeping sunset views. Set on part of the Chatham coastline with a short, private beach, the 13-year-old house is, like all good houses, oriented perfectly to soak up that evening light in the summer as it streams across a salt marsh, an inlet and the ocean and floods its bluestone patio and near-continuous wall of windows.

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 Nov. 15-21, 2025.

1) 12 Derrymore Road, Nantucket

Price: $9,550,000
Buyer: Ack Park LLC
Seller: 12 Derrymore Reaty T
Agent: Dawn Hill, Great Point Properties
Size: 6,548 square feet on 0.22 acres
Sold: 11/14/2025

2) 44 Nickerson Lane, Chatham

Price: $8,650,000
Buyer: Peabody Ter Partners LLC
Seller: 44 Nickerson LLC
Agent: Chris Rhinesmith, Compass
Size: 3,117 square feet on 0.42 acres
Sold: 11/14/2025

3) 59 Chestnut St., Boston

Price: $8,600,000
Buyer: 59 Chestnut Street RT
Seller: Alex A. Rogers and Alexis Rogers
Agent: Tracy Campion, Campion & Co.
Size: 6,442 square feet
Sold: 11/17/2025

4) 165 W. Canton St., Boston

Price: $8,500,000
Buyer: 165 Wc T
Seller: 165 Wc LLC
Agent: Not Sold Via MLS
Size: 4,373 square feet
Sold: 11/14/2025

5) 45 Easton St., Nantucket

Price: $7,800,000
Buyer: 45 Easton St LLC
Seller: Harold Bro Realty LLC
Agent: Ty Costa, William Raveis Real Estate
Size: 2,940 square feet on 0.11 acres
Sold: 11/17/2025