Real Estate

These Are the Most Expensive Homes for Sale on Cape Cod

Including waterfront mansions and an entire private island.

13 Kingsbury Lane, Orleans / Photo courtesy of Robert Paul Properties

Have a spare $10 million lying around? That’s almost how much it’d cost to buy the 10th most expensive home for sale on Cape Cod.

A new report from real estate analytics firm NeighborhoodX crunched the numbers to identify the top 10 most expensive properties for sale on the right arm of Massachusetts. The list, as you’d expect, is a jaw-dropping assortment of estates. From waterfront mansions to an entire private island, there’s something for all of us who’ve been cursed with expensive taste.

While asking prices dip as low as $9,975,000 toward the end of the list, they top out at a whopping $19,955,000. An impressive shingle-clad manse in Chatham takes the cake as the most expensive house for sale on Cape Cod. The home doubles as one of the priciest in the state, and offers more than 10,000 square feet of living space. It’s followed by a nine-acre estate in West Hyannisport, which asks $19,500,000. The compound has a private beach with views of Nantucket Sound and Martha’s Vineyard.

sipson island orleans

Sipson Island / Photo courtesy of Robert Paul Properties

“‘Houses’ isn’t the key word here,” says Constantine Valhouli, director of research at NeighborhoodX. “Compound is more accurate. Waterfront is descriptive. Gatsby-esque works, too.”

The rest of the Cape dream homes can be found in Barnstable, Osterville, and Orleans. Perhaps the most unique one of all is Sipson Island—a sandy oasis surrounded by the blue waters of Pleasant Bay. The private island is made up of nine parcels of land that include multiple dwellings, both seasonal and year-round. There are also two boathouses and three docks which offer deep water boat access for fishing and cruising.

Other costly highlights include a Patrick Ahearn-remodeled home in Osterville.

Envisioning summertime in your future beach house? See the complete list of the Cape’s most expensive homes below.


Madeline Bilis Associate Editor at Boston Magazine @madelinebilis
mbilis@bostonmagazine.com