Image courtesy of Embarc

The first home in this week’s Gossip Report is almost a record-setter: It’s the most expensive Beacon Hill home sold since a $28.25 million sale in 2023. The townhome close to Boston Common was carried out by Crest City Capital and originally listed for $25 million. Technically built in 1825, Crest City’s renovation was so thorough, the new buyers will be able to enjoy completely new structural framing, floor plates and building systems – plus the touch of one of Boston’s major commercial architecture firms, Embarc Design.

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 Feb. 14-20 2026.

1) 46 Chestnut St., Boston

Price: $22,000,000
Buyer: DVS RT
Seller: 46 Chestnut Street LLC
Agent: Brad Cangiamila, CCC Real Estate LLC
Size: 9,380 square feet
Sold: 2/17/2026 

2) 37 Cliff Road, Nantucket

Price: $8,141,000
Buyer: Callmomndad-Onemoretime RT
Seller: 37 Cliff Rd NT
Agent: Bernadette Meyer, Maury People Sotheby’s 
Size: 3,113 square feet on 0.14 acres
Sold: 2/18/2026 

3) 88 Cutler Lane, Brookline

Price: $5,860,000
Buyer: Song Han
Seller: Cutler Lane LLC
Agent: Viktoriya Vilkomir, New England Elite Realty LLC 
Size: 6,791 square feet on 0.78 acres
Sold: 2/18/2026 

4) 439 Sea View Ave., Osterville

Price: $5,800,000
Buyer: 439Sva Osterville LLC
Seller: Mary M. Madden
Agent: Paul E. Grover, BHHS Robert Paul Properties
Size: 4,021 square feet on 1.07 acres
Sold: 2/18/2026 

5) 77 Warren Ave., Boston

Price: $4,920,000
Buyer: Shaune Berg and Steven Berg
Seller: Luke Lesaffre
Agent: Unknown / Not Sold Via MLS
Size: 2,611 square feet
Sold: 2/19/2026