Photo courtesy of Fisher Real Estate

What kind of views would your dream home have? There are plenty to choose from in this week’s roundup of Massachusetts’ most expensive home sales. The first home in the roundup sits a head taller than its neighbors – and the surrounding scrub oak – thanks to a hill. The third and fifth look out onto two of Chatham’s many coves, and the Back Bay spills out in front of the fourth. Only the second house, nestled in a forest, doesn’t boast vistas.

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 solely the most expensive single-family and residential condominium transactions for May 16-22, 2026. 

1) 4 Shawkemo Hills Lane, Nantucket

Price: $10,000,000
Buyer: Four Shawkemo Nantucket LLC
Seller: Charlotte A. Rogers and Gary L. Rogers
Agent: Brian Sullivan, Fisher Real Estate
Size: 6,065 square feet on 2.39 acres
Sold: 5/20/2026

2) 3 Idlewile Lane, Weston

Price: $9,739,680
Buyer: Weston 3 Idlewile RT
Seller: Lisa Wallack and Neil A. Wallack
Agent: Collin Sullivan and Daniel Resop, William Raveis Real Estate
Size: 9,314 square feet on 6.03 acres
Sold: 5/22/2026

3) 246 Stage Island Road, Chatham

Price: $7,312,500
Buyer: Chatham 246 Sir T
Seller: Patricia S. Gibson and Peter W. Gibson
Agent: Chris Rhinesmith, Jessica Blute LaRocco and Pam Wise, Compass
Size: 3,712 square feet on 0.91 acres
Sold: 5/21/2026

4) 17 Commonwealth Ave. #1, Boston

Price: $7,050,000
Buyer: Cody’s Treats LLC
Seller: Laurie Hollis Glimcher
Agent: Janice Lipof, Hammond Residential Real Estate
Size: 3,500 square feet
Sold: 5/21/2026

5) 330 Seapine Road, Chatham

Price: $5,500,000
Buyer: 15:30 Seapine LLC
Seller: 330 Seapine Road NT
Agent: Unknown / Not sold via MLS
Size: 2,910 square feet on 1.04 acres
Sold: 5/19/2026