The five highest-priced home sales reported in Cape Cod & the Islands, Massachusetts for the week ending October 25, 2026, came to a combined $36.55 million. Every one of them sold for more than $6 million.
The group is a varied one. The homes have between four and eight bedrooms, and their lots run from about 10,000 square feet to more than three acres. Among them are a home finished this year and sold with its furnishings, a harbor-view home in Monomoy, a hillside estate in Tom Nevers East and a shingled home on Oyster Pond.
No. 1 — $8,325,000 · 20 W Chester St, Nantucket, Massachusetts
The week’s top sale was a Nantucket home designed by KMS Design and built in 2016. It sold for $8,325,000. The property last sold for $6.995 million in 2024.
A wide foyer with a barrel ceiling leads into the living room, where a full wall of windows brings in daylight and a fireplace sits beside a generous seating area. The den has oversized glass doors and built-in cabinetry. In the kitchen, a center island with seating looks toward a breakfast area that overlooks the three-season porch. French doors from the living room open onto that porch, which has folding glass windows and a gas fireplace. Custom cabinetry and built-ins appear throughout, set against oak floors.
The home has four bedrooms, each a suite, along with six bathrooms, four full and two half, in 3,287 square feet of living space. One suite is on the first floor. Upstairs, two guest suites share a spacious landing at the front of the home, and the primary suite has a west-facing balcony and large south-facing windows. Its bath has a freestanding soaking tub, a floating double vanity and heated floors. The third floor is an open living area with a half bath, two built-in twin daybeds and shiplap walls from floor to ceiling, suited to a playroom or a home office.
The lot covers 10,301 square feet, the smallest of the five. Outdoors, the home has a bluestone patio and a covered side porch, along with a lawn and a fire pit.
Shellie Dunlap of Lee Real Estate was the listing agent for the week’s highest-priced sale, and Sam Parsons of Lee Real Estate represented the buyer.
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No. 2 — $7,400,000 · 57 Somerset Rd, Nantucket, Massachusetts
The newest of the five homes was built in 2026 by Hanley Development in a Hummock Pond neighborhood of Nantucket, and it sold fully furnished for $7,400,000. The property last sold for $1.95 million in 2025, before the current home was built.
The heart of the first floor is one open kitchen, living and dining area under a vaulted ceiling, with plenty of windows. The kitchen has a blue La Cornue range and a Sub-Zero refrigerator and freezer, and a pantry and a small desk area sit next to it. The living room has a fireplace, and doors lead out to a patio and to an outdoor dining area with a grill station. Off the front hall are a private office with built-ins and a den that gets the morning sun.
The primary suite is on the first floor, with two walk-in closets, a soaking tub and direct access to the backyard. The other three bedrooms are on the second floor, each with its own bath, and one of them looks west toward the sunset over Land Bank property. In all, the home has four bedrooms and five bathrooms, four full and one half, in 3,633 square feet on 0.46 acres.
Outside, a 16-by-36-foot pool is paired with a poolside cabana that has a lounge area, a bar with two drink refrigerators, a powder room and an outdoor shower. The yard borders more than 30 acres of protected Land Bank property, and the beach and Cisco Brewery are within biking distance. Below the main floors, a full poured basement of more than 1,800 square feet is still unfinished. The listing includes an example floor plan for it with two more bedroom suites, a game room and a gym with a sauna.
Brian Fox of Hanley Garrette Group LLC was the listing agent, and Jennifer Shalley Allen of Fisher Real Estate represented the buyer.
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No. 3 — $7,225,000 · 61 Monomoy Rd, Nantucket, Massachusetts
In Monomoy, a 1975 home across the street from Nantucket Harbor sold for $7,225,000. The home sits about 16 feet above sea level, outside the flood zones, on 0.72 acres served by town water and sewer. It has been owned by its current owners for more than 50 years, according to the listing.
The main living space is on the second floor. There, an open living area has a wood-burning fireplace and a large picture window facing the harbor, and it opens onto a deck that looks across the water to Brant Point. The dining area, kitchen, pantry and primary bedroom share that floor. The other three bedrooms are on the first floor, one with its own bath, along with a den whose doors open to a rear deck with an attached garden shed. The home has four bedrooms and three bathrooms in 1,656 square feet, the smallest living area of the five.
Bill Liddle of Great Point Properties was on both sides of the sale, as the listing agent and as the buyer’s agent. It was the only sale in this Top 5 with the same agent representing both sides.
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No. 4 — $7,200,000 · 42 Chuck Hollow Rd, Nantucket, Massachusetts
Hollyhock sits on a hill in Tom Nevers East, on 3.01 acres, the largest lot among the five. From both floors, the views take in the Atlantic Ocean, conservation land and Tom Nevers Pond. The home, built in 1982, sold furnished for $7,200,000. The property last sold for $6.2 million in 2023.
The approach is by a semicircular oyster shell driveway lined with river birch, hydrangeas, rhododendron and borders of lavender. Part of the property’s history is an 1840s barn in a Shaker-like style, moved from the Berkshires a few decades ago. The property also includes a guest cottage.
Inside, a two-story entry has a wood-burning fireplace and two open staircases, and the floors are wide-plank historic pine. The formal dining room has raised paneled walls and wainscoting, and the sitting room has custom built-ins. A sunroom with vaulted ceilings opens through French doors to a deck with an outdoor fireplace and ocean views. The primary suite, on the first floor, has its own ocean-view balcony. On the second floor, a living room with a fireplace opens through double French doors to another deck facing the ocean. On the lower level, a living room framed in original stone and wood beams has a wood-burning fireplace.
With 4,514 square feet, eight bedrooms and six bathrooms, four full and two half, it is the largest home of the five and has the most bedrooms. Outdoors, a bluestone patio leads toward a sunken garden built around a stone fireplace. A pavilion stands beside the 60-by-20-foot heated saltwater pool, which has a retractable cover, and there is an outdoor kitchen. The whole perimeter is fenced.
Bruce Beni & Peter Engen of Maury People Sotheby’s International Realty were the listing agents, and Chandra Miller of Maury People Sotheby’s International Realty represented the buyer.
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No. 5 — $6,400,000 · 108 Queen Anne Road, Chatham, Massachusetts
The one Chatham sale on the list is a shingled home on Oyster Pond, within walking distance of the town’s historic village center. It sold for $6,400,000. Built in 1950, it is the oldest of the five homes. The property last sold for $910,000 in 1997.
Privacy fencing and mature plantings set the home apart from the road on a sloped corner lot of 0.75 acres. A private pier and dock have room for two boats, and from there a boat can head out through Stage Harbor to Nantucket Sound. Closer to the home are a deck, a patio, a garden and a hot tub.
The two-story home has five bedrooms and six bathrooms, four full and two half, in 4,248 square feet, plus a full finished basement. It has water views, large windows and a primary suite. The property also includes a guest house and a garage for six cars.
Dawn Boynton of Berkshire Hathaway HomeServices Robert Paul Properties was the listing agent, and Judith L Smith of John C Ricotta & Assoc. represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 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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