The five highest-priced home sales reported on Cape Cod for the week ending October 18, 2026, totaled $33.815 million. The homes stretch from Chatham to Bourne and North Falmouth, with two in Osterville, and their construction spans more than a century, from 1891 to 1993.
Berkshire Hathaway HomeServices Robert Paul Properties listed three of the five, including one of the two homes that tied for first place.
No. 1 — $8,500,000 · 166 Shore Road, Chatham, Massachusetts
Known as The SandBox, the Shore Road home in Chatham sold for $8,500,000, one of two sales tied for first place this week. The property covers 1.12 acres with its own private beachfront, steps from the Chatham Bars Inn. From the home, a staircase lined with flowering plantings descends to a bluestone patio and outdoor entertaining areas above the sand, and a private path continues on to the water.
The home was built in 1940 and is finished in cedar shake and shingle. It has been extensively renovated while keeping the craftsmanship of its original construction. At 1,738 square feet, it is the smallest of the five by living area, a two-story home with four bedrooms and three bathrooms. A shiplap-paneled great room leads into the dining and kitchen areas, which look out at the water, and the primary suite has a bay window of its own. Outside are a garden and an outdoor shower. The property last sold for $2.9 million in 2003.
The Guthrie Schofield Group of Berkshire Hathaway HomeServices Robert Paul Properties listed the home, and Betsy Hargreaves of Gibson Sotheby’s International Realty represented the buyer.
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No. 2 — $8,500,000 · 75 Winsor Rd, Bourne, Massachusetts
The other $8,500,000 sale is an island. Rocky Island, on Winsor Road in the Pocasset section of Bourne, is joined to the mainland by a wooden bridge, so it has the seclusion of an island and the easy access of a mainland property. At 2.84 acres, it is the largest lot in this Top 5.
The Cape-style home dates to 1891, making it the oldest of the five. It was fully renovated in 2014, when its systems were brought up to date and it was winterized for use beyond the summer season. It has seven bedrooms, the most in the group, and each of them has a water view. There are eight bathrooms, seven full and one half, along with three fireplaces and 6,839 square feet of living space. A covered porch wraps around the home and takes in wide views of the harbor and the sunsets.
A pool, a pool house and a detached two-car garage are on the grounds. The shoreline is a privately owned sandy beach, and a deepwater dock is in place for the season. The property last sold for $3.04 million in 2013.
G. Stewart Young of LandVest, Inc. was the listing agent. Nick Fish III of William Raveis R.E. & Home Services represented the buyer.
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No. 3 — $7,250,000 · 168 Garrison Lane, Osterville, Massachusetts
The largest home in the week’s ranking, at 7,565 square feet, is on Garrison Lane in Osterville, and it sold for $7,250,000. Built in 1993, it is also the newest of the five. The 1.48-acre property looks out over West Bay and the Eel River, and it has a private sandy beach and a deep-water dock with access to Nantucket Sound.
The clapboard home has a two-story great room with a wide expanse of windows facing the water. The main level also includes a living room, a formal dining room, a home office, and a chef’s kitchen next to a sunny sitting room. The primary suite is on the first floor and has water views of its own, while a second primary suite and three more bedrooms are upstairs. A tower room offers a 360-degree view of the surroundings and the sunsets.
The finished lower level adds a recreation area, a wet bar and a kitchenette. In all, the home has five bedrooms, six bathrooms, two fireplaces and a three-car garage, and outside are a terrace, a deck, a patio and gardens. The village center of Osterville is only moments away.
Robert B Kinlin of Berkshire Hathaway HomeServices Robert Paul Properties was the listing agent, and W&W Boston/Cape Cod Connection of Compass Massachusetts, LLC represented the buyer.
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No. 4 — $5,000,000 · 150 Waterside Drive, North Falmouth, Massachusetts
In the Seascape community of North Falmouth, the shingled home at 150 Waterside Drive was built in 1971 and has been completely renovated. It looks out across Buzzards Bay, and every room has a view of the water. Built-in steps lead straight down to one of Seascape’s two private association beaches, and residents also share tennis and pickleball courts and a boat dock.
The lot is level and landscaped, and at 0.39 acres it is the smallest in this Top 5. A deck and a patio have an outdoor kitchen and grill, and there are also a hot tub and an outdoor shower. The home has 3,401 square feet of living space with four bedrooms, three full baths and one half bath, a fireplace, a wet bar and a finished basement. The property last sold for $1.8 million in 2006.
The home went under contract the same day it was listed and sold for its full asking price of $5,000,000. Janet Michienzi of William Raveis Real Estate & Home Services was the listing agent.
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No. 5 — $4,565,000 · 313 Bridge Street, Osterville, Massachusetts
On Little Island in Osterville, 313 Bridge Street is a family compound. Besides the main residence, the property has a detached three-car garage with a home gym above it, a swimming pool, a pool house with a kitchenette and a full bath, and a guest house. It sold for $4,565,000. With the Garrison Lane sale, it gives Osterville two of the five, together worth $11,815,000.
The main residence was built in 1940 and has 5,970 square feet of living space. Its interiors are finished with custom millwork, designer wallpaper and vaulted ceilings. The chef’s kitchen has professional-grade appliances, and a smart home system runs the doors and locks. The primary suite is on the first floor, with custom closets and a bath that has a jetted Grohe shower system. Four more bedrooms include a second primary suite on the second floor. The home’s eight bathrooms, seven full and one half, tie the Pocasset home for the most in the group, and there are two fireplaces and a finished lower level.
Outside, the backyard has a poolside terrace with a summer kitchen and a fire pit, set among manicured, park-like grounds on 0.93 acres. There is also a screened porch. The property last sold for $3.55 million in 2021.
Paul E Grover of Berkshire Hathaway HomeServices Robert Paul Properties was the listing agent, the brokerage’s third listing in this week’s Top 5. Ellen Valentgas of Sotheby’s International Realty represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 18, 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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