These are the five highest-priced home sales reported in the Barnstable Town, Massachusetts metro area for the week ending October 4, 2026, and together they total $17.53 million. All five are single-family homes in Barnstable County, and they range from a historic Provincetown home to a contemporary Cape. Two of the five are in Provincetown, one is in North Chatham, one is in South Chatham and one is on Popponesset Island in Mashpee.
No. 1 — $6,950,000 · 50 Popponesset Island Road, Mashpee, Massachusetts
Popponesset Island is reached by a one-lane bridge, and the home at 50 Popponesset Island Road looks out across Popponesset Bay toward Nantucket Sound. The 0.80-acre property has its own dock, giving the new owners a way onto the bay and out to the Sound.
The shingle-sided home was built in 1998 and has four bedrooms, four bathrooms and 4,069 square feet of living space, the most of any home in this week’s Top 5. It also has two separate guest areas. There is a deck, a fireplace and hardwood, tile and carpeted floors, and the listing presents the interiors as ready for a new owner to update.
The home went under contract nine days after it was listed. Jack B Cotton, Jr of Sotheby’s International Realty was the listing agent, and Lindsay Sullivan of New Seabury Sotheby’s International Realty represented the buyer in the week’s highest-priced sale.
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No. 2 — $4,000,000 · 40 Middle Road, North Chatham, Massachusetts
The home at 40 Middle Road is in North Chatham’s Harbor Coves Association, which gives its residents beach access on Crows Pond. From the pond there is deep-water access out to Pleasant Bay.
Eastward built the shingle-sided home in 2016, and it has a farmer’s porch at the entrance and a cupola among its architectural details. Inside, the great room has vaulted ceilings, and the kitchen, living and dining areas open to one another, finished with custom cabinetry. A sunroom adds more living space. Outside, a bluestone patio has an outdoor kitchen and a fire pit.
The primary wing is on the main level, with a walk-in closet, its own bath and windows that look out on the grounds. Upstairs, two more bedrooms share a full bath, and there is a lounge and game area as well as a bonus room with its own bath. The home has three bedrooms, three full baths and a half bath, two fireplaces and 3,838 square feet on 0.45 acres with landscaped gardens. There is also a two-car garage. The property last sold for $2.124 million in 2018.
The home went under contract seven days after it was listed and sold for $505,000 above its $3.495 million asking price. Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties was the listing agent, and Chris Rhinesmith of Compass Massachusetts, LLC represented the buyer.
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No. 3 — $2,635,000 · 15 Center Street, Provincetown, Massachusetts
Built in 1800, the home at 15 Center Street is the oldest in this week’s Top 5. It stands on a corner lot one block from Commercial Street, and a turreted corner and a gambrel roofline give it an unmistakable profile. The exterior is clapboard and shingle, and much of its historic detailing remains.
Inside, the kitchen has a fireplace, and there are both formal and informal living areas. A large en suite bedroom is on the first floor, and upstairs are two primary suites, each with its own bath. The home has 2,457 square feet, and its five bedrooms and five bathrooms are the most among the five homes. Two of the bathrooms were recently updated.
A three-season room opens to the outdoors, where there are landscaped gardens and a large deck for entertaining. The 7,405-square-foot lot also has an outbuilding and parking for six or more cars. The property last sold for $1.29 million in 2017.
Iskren ”Isi” Georgiev of Gibson Sotheby’s International Realty was the listing agent, and Holmes Group of Berkshire Hathaway HomeServices Robert Paul Properties represented the buyer. Gibson Sotheby’s International Realty also listed the next sale on this list, another Provincetown home.
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No. 4 — $1,999,500 · 27 Blueberry Avenue, Provincetown, Massachusetts
The kitchen at 27 Blueberry Avenue in Provincetown was renovated in 2023 and opens to the living and dining areas. The clapboard home was built in 1993 and has three bedrooms, two bathrooms and 1,889 square feet on a quarter-acre lot. A bedroom and a full bath are on the first floor, and there is a full basement, a one-car garage and a garden. The home also has owned solar panels and a whole-house generator, and it is near beaches, trails, restaurants, galleries and the center of town.
Joan A Lenane of Gibson Sotheby’s International Realty was the listing agent, and Max Cliggott-Perlt of Berkshire Hathaway HomeServices Robert Paul Properties represented the buyer.
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No. 5 — $1,950,000 · 4 Williams Way, Chatham, Massachusetts
At 4 Williams Way in South Chatham, one of the main living spaces is outdoors. A covered outdoor living room sits under a beadboard ceiling, with a Cambridge ledgestone fireplace and a television set into the wall. Past the covered area, the patio opens to the sky, and a lawn leads to a fenced vegetable garden and a detached shed.
The contemporary Cape was built in 2018, the newest home in this Top 5, and its 1.50 acres make it the largest lot of the five. It is on a cul-de-sac of five homes, 1.7 miles from Cockle Cove Beach and minutes from downtown Chatham.
Inside, an open living area centers on a kitchen with a quartz island that seats four. The primary suite has two walk-in closets and a bath with a soaker tub and a tiled shower. One bedroom is on the main level, and three more bedrooms and a full bath are on the second floor. The half bath on the main floor also serves as the laundry. The home has four bedrooms, two full baths and a half bath in 2,198 square feet, along with a mud room, a full basement and an attached one-car garage with walk-up storage above it. The property last sold for $662,912 in 2018.
The home went under contract eight days after it was listed and sold at its full asking price of $1.95 million. Erin Terkelsen of LPT Realty, LLC was the listing agent, and Stefanie Clifford of Keller Williams Realty Boston Northwest represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 4, 2026. The report may exclude private, off-market, delayed or nondisclosed transactions. Prices, property details and professional representation are reported as available at publication and may be updated following confirmation from transaction participants.
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See full market data on our Barnstable Town, Massachusetts market page.
