Photo courtesy of Lee Real Estate

Tucked into a cul-de-sac, the fifth home in this week’s roundup of Massachusetts’ most expensive home sales doesn’t feel like it’s a 20-minute walk from a subway station. The house sits on an almost-half-acre lot atop Cambridge’s Observatory Hill, wrapped in a blanket of trees. It furthers that seclusion with an imposing, nearly-blank wall facing the street, keeping its windows for its more private eastern, southern and western exposures.

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. 11-17, 2025.

1) 258 Polpis Road, Nantucket

Price: $16,850,000
Buyer: 258 Polpis RT
Seller: Stephanie M Stavnes RET
Agent: Jeanne Hicks, Lee Real Estate
Size: 6,083 square feet on 6.43 acres
Sold: 10/15/2025

2) 41 Monomoy Road, Nantucket

Price: $15,000,000
Buyer: Angela Berry and Timothy Berry
Seller: Sopris 715 LLC
Agent: Meg Ruley, Atlantic East Nantucket Real Estate
Size: 4,484 square feet on 0.75 acres
Sold: 10/10/2025

3) 776 Boylston St. #W9B, Boston

Price: $8,000,000
Buyer: Mc Unit LLC
Seller: Hilltopper Boston LLC
Agent: Not Sold Via MLS
Size: 2,494 square feet
Sold: 10/15/2025

4) 25 Osprey Lane, Chilmark

Price: $7,222,546
Buyer: Osprey Gardens LLC
Seller: G & Dene E Feldman T
Agent: Deborah Hancock, Hancock Real Estate
Size: 3,205 square feet on 3.9 acres
Sold: 10/15/2025

5) 18 Hemlock Road, Cambridge

Price: $7,125,000
Buyer: Derek A. Kopon
Seller: Helen H. Bouscaren and Joseph G. Bouscaren
Agent: John Petrowsky, Compass
Size: 5,380 square feet on 0.43 acres
Sold: 10/15/2025