It’s another showdown of handsome seaside homes in this week’s Gossip Report. In the red corner and the No. 1 spot, it’s a contemporary creation made up of three rectangles and a stone-walled cylinder. Measuring in at 5,808 square feet, it puts its location on top of a short hill to good effect with all-around windows. In the blue corner and the No. 4 spot it’s the challenger, also from 2008 but taking its design cues from homes 150 years older. Measuring in at only 3,824 square feet, this one’s built for cozy family gatherings.

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 sales for April 22-28, 2025.

1) 2 Squibnocket Road, Chilmark

Price: $9,525,000
Buyer: Jarvis 101 LLC
Seller: Mary M. Callagy
Agent: Tina Miller and Claire Callagy, Compass
Size: 5,808 square feet on 4.5 acres
Sold: 4/25/2025

2) 81 Summit Ave., Brookline

Price: $5,112,500
Buyer: Eduardo S. Lisker and Anne K. Snider
Seller: Jm Const & Design LLC
Agent: Marina Fishman, Panorama Realty
Size: 4,045 square feet on 0.27 acres
Sold: 4/25/2025

3) 400 Stuart St. #25E, Boston

Price: $4,850,000
Buyer: Inversiones 5HB Boston Sociedad Limitada
Seller: Charles Magnum and Elaine Magnum
Agent: Tracy Campion, Campion & Co.
Size: 2,495 square feet
Sold: 4/22/2025

4) 79 Barcliff Ave., Chatham

Price: $4,500,000
Buyer: Kathryn A Tinsley RET
Seller: Elizabeth M Gardner T
Agent: Doug Grattan, Christine’s International Atlantic
Size: 3,824 square feet on 0.73 acres
Sold: 4/23/2025

5) 11 Beech Road, Weston

Price: $4,275,000
Buyer: Denise M. Alber and Thomas P. Alber
Seller: 87 Clifton LLC
Agent: Deena Powell and Casey Caso, Advisors Living
Size: 6,700 square feet on 1.47 acres
Sold: 4/22/2025