Photo courtesy of LandVest

The highest-grossing residential sale in Martha’s Vineyard history tops this week’s roundup of the most expensive home sales in Massachusetts. Anyone who owns architect Patrick Ahern’s coffee-table book “Timeless” will recognize its formal entry court and gambrel roofs that hide a bowling alley among other amenities, according to the listing. The second home in this week’s roundup is also of note: The seller was investor David Malm, who had sought to renovate the home to add to his portfolio of island luxury rentals but was thwarted by neighborhood opposition.

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 Oct. 25-31, 2025.

1) Address: 48 Witchwood Lane, Edgartown

Price: $37,500,000
Buyer: 48 Witchwood Nt
Seller: Summer Bay LLC
Agent: Gerret Conover and Thomas Leclair, LandVest
Size: 13,071 square feet on 3 acres
Sold: 10/30/2025

2) Address: 81 South Water St., Edgartown

Price: $17,250,000
Buyer: Edward Jepsen
Seller: Goldeneye LLC
Agent: Gerret Conover and Thomas Leclair, LandVest
Size: 3,156 square feet on 0.67 acres
Sold: 10/30/2025

3) Address: 1 Dalton St. #4602, Boston

Price: $12,000,000
Buyer: Sfp Ky 2006 LLC
Seller: Back Bay Hideaway LLC
Agent: Maggie Gold Seelig, MGS Group Real Estate
Size: 4,361 square feet
Sold: 10/27/2025

4) Address: 94 Menemsha Inn Road, Chilmark

Price: $8,178,500
Buyer: Edward R. Damiano and Toby M. Milgrome
Seller: Money Slotch T
Agent: Julianna Flanders, Flanders Real Estate
Size: 2,413 square feet on 5.6 acres
Sold: 10/27/2025

5) Address: 196 Cliff Road, Nantucket

Price: $7,500,000
Buyer: Barry L. Boniface and Lora L. Boniface
Seller: Barbara S. Daley and Paul P. Daley
Agent: John McGarr, Maury People Sotheby’s
Size: 3,788 square feet on 1.84 acres
Sold: 10/28/2025