Photo courtesy of J Pepper Frazier Co.

The first house in this week’s roundup of Massachusetts’ most expensive home sales traded for $13.25 million in 2021 – and $31 million on Sept. 30. What gives? Large upgrades to the property, that’s what. Wetlands regulatory filings show the property got at least a pool, hot tub, pool house, new garage and significant new landscaping in 2022. And it’s not even the biggest sale in the exclusive Cliff neighborhood this fall: 3 Sherburne Way recently traded hands for $37.75 million in an off-market sale.

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 Sept. 27-Oct. 3, 2025.

1) 8 Sachem Road, Nantucket

Price: $31,000,000
Buyer: Nantucket Sojourn LLC
Seller: Sachem T
Agent: J. Pepper Frazier II, J Pepper Frazier Co.
Size: 6,915 square feet on 1.02 acres
Sold: 9/30/2025

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2) 30 Eel Point Road, Nantucket

Price: $19,000,000
Buyer: Sopris 715 LLC
Seller: 30 Eel Point LLC
Agent: Dalton T. Frazier, J Pepper Frazier Co.
Size: 6,117 square feet on 2.65 acres
Sold: 10/1/2025

3) 184 Cliff Road, Wellesley

Price: $14,750,000
Buyer: Alice Marriott Hales RET
Seller: 184 Cliff Road NT
Agent: Melissa Dailey, Coldwell Banker – Wellesley
Size: 10,663 square feet on 2.45 acres
Sold: 9/30/2025

4) 7 North Swift Rock Road, Nantucket

Price: $10,800,000
Buyer: 7 North Swift Rock LLC
Seller: Coulon Realty NT
Agent: Kathy Gallaher, Maury People Sotheby’s
Size: 4,809 square feet on 2.56 acres
Sold: 10/2/2025

5) 10 Old Westmoor Farm Road, Nantucket

Price: $9,570,000
Buyer: 10 OWF LLC
Seller: Lynn K. Mills and Thomas L. Mills
Agent: J. Pepper Frazier II, J Pepper Frazier Co.
Size: 5,838 on 0.55 acres
Sold: 10/1/2025