Photo courtesy of William Raveis

This week’s roundup of the most expensive home sales in Massachusetts is all about the vacation. All five homes come from exclusive coastal or near-coastal neighborhoods, with amenities to match their seven- and eight-figure pricetags: Pools, private docks, ensuite bathrooms with every bedroom, sweeping ocean views or walking distance from downtown Nantucket’s restaurants and shops – take your pick.

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 Dec. 13-19, 2025.

1) 391 Sea View Ave., Osterville

Price: $10,500,000
Seller: G & D Johansen FT
Buyer: 391 Webster NT
Agent: Gene Orloff, Sotheby’s International Realty
Size: 5,502 square feet on 1.23 acres
Sold: 12/16/2025

2) 240 Polpis Road, Nantucket

Price: $ 8,565,000
Seller: 240 Polpis LLC
Buyer: Michael J. Omara
Agent: Robert Sarkisian, BHHS Island Properties
Size: 4,498 square feet on 3.47 acres
Sold: 12/16/2025

3) 115 Surfside Road, Nantucket

Price: $7,950,000
Seller: One Fifteen Surfside LLC
Buyer: Rose Miller and Peter Miller
Agent: Lucie Cristler, Maury People Sotheby’s
Size: 5,512 square feet on 0.96 acres
Sold: 12/17/2025

4) 27 Cato Lane, Nantucket

Price: $7,850,000
Seller: David Gilberg and Margaret Gilberg
Buyer: Cato LLC
Agent: Rebecca M Becker, J Pepper Frazier Co.
Size: 6,811 square feet on 0.51 acres
Sold: 12/16/2025

5) 1 Chester St., Nantucket

Price: $7,400,000
Seller: One Chester RT
Buyer: One Chester LLC
Agent: Robert Young, William Raveis Nantucket
Size: 3,467 square feet on 0.12 acres
Sold: 12/16/2025