Photo courtesy of Tea Lane Associates

The third home in this week’s roundup of the most expensive home sales in Massachusetts started out as a “fishing camp” where local men gathered to fish and drink beer. According to the listing brokerage, Tea Lane Associates, its owner in the 1950s suddenly found himself hard up for cash during a sudden recession and convinced his famed actress neighbor to buy it for “a very good price” by painting its weathered cedar shingles bright blue. From then on, locals knew it as “The Swindle.”

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 Jan. 3-9, 2026.

1) 50 Liberty Drive #PH1B, Boston

Price: $ 14,500,000
Buyer: 50 Liberty Value Growth LLC
Seller: 50 Liberty Drive LLC
Agent: Tracy Campion, Campion & Co.
Size: 3,619 square feet
Sold: 1/7/2026

2) 21 1/2 Hussey St., Nantucket

Price: $6,900,000
Buyer: Mkkh LLC
Seller: Watercolors LLC
Size: 3,800 square feet on 0.12 acres
Sold: 1/7/2026

3) 662 Chappaquonsett Road, Tisbury

Price: $6,825,000
Buyer: 662 Vineyard LLC
Seller: Robert A Schmetterer RET
Agent: Jill Hobby Napior, Tea Lane Associates | Forbes
Size: 1,914 square feet on 1.58 acres
Sold: 1/5/2026

4) 25 Rutland Square, Boston

Price: $6,075,000
Buyer: 25 Rutland Sqauare LLC
Seller: Holly Grace and Benjamin Rubenstein
Size: 3,904 square feet
Sold: 1/7/2026

5) 168 Beacon St. #1, Boston

Price: $5,700,000
Buyer: Scott F Powers 2004 FT
Seller: Violette Aftandilian
Agent: Alene Caldwell and Jonathan Caldwell, Acre Property Advisors LLC
Size: 3,105 square feet
Sold: 1/7/2026