These were the highest-priced home sales reported in Cape Cod & the Islands, Massachusetts for the week ending November 1, 2026, and together the five came to $42 million. Three of the homes are on Nantucket, one is in Edgartown and one is in Chatham, and all five are single-family homes.
The group spans close to two centuries of building. The oldest home dates to 1845 and sits on the smallest lot of the five, yet it also has the most living space. The newest was completed in 2026, and the largest piece of land, 1.80 acres, belongs to an Edgartown home built in 2014.
No. 1 — $15,250,000 · 94 Main St, Nantucket, Massachusetts
The Hadwen-Wright House at 94 Main Street is a Greek Revival landmark designed by builder-architect Frederick Brown Coleman, and it was built in 1845. Visitors arrive beneath a monumental Corinthian portico. Inside, a curved staircase rises from the front foyer through soaring ceilings, past original wide-plank pine floors and preserved millwork, to a circular landing under a domed ceiling with ornate plasterwork and Corinthian capitals.
The most remarkable room is upstairs. The home’s original ballroom, with its dome, plasterwork and marble fireplace intact, has been turned into the primary suite. Two more guest suites share that floor, one with paneled walls and an exposed-beam ceiling, the other with a sunny seating alcove above the rear gardens. On the third floor, a hallway is lined with built-in twin sleeping alcoves, and a final staircase climbs to the belvedere, kept as a sitting room with views across Nantucket’s Historic District and toward the harbor.
The main floor has formal living and dining rooms, a renovated kitchen with vaulted ceilings and a large island that opens to the patio, a family room and a guest bedroom with its own bath. Below, the restoration took up the lower level’s original brick floor, numbered each brick and laid it back in place. A recreation room there opens to the brick terrace and gardens and shows off a historic brick-lined well under a glass floor. The home has five bedrooms, seven bathrooms and 6,106 square feet on a 4,356-square-foot lot, and it is subject to historic preservation restrictions. The property last sold for $4.7 million in 2014.
The home went under contract one day after it was listed. Bernadette Meyer of Maury People Sotheby’s International Realty was the listing agent, and Gary Winn, also of Maury People Sotheby’s International Realty, represented the buyer.
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No. 2 — $10,750,000 · 5 Pilgrim Rd, Nantucket, Massachusetts
The home at 5 Pilgrim Road sits in Nantucket’s Cliff neighborhood, close to The Westmoor Club, Steps Beach and Town. Tomaiolo Development completed it in 2019, and Sophie Metz Design was responsible for both the architecture and the interiors. Its six bedrooms and eight bathrooms are the most of any home in this week’s group, in 5,600 square feet on 0.28 acres, and it sold furnished.
The open living room, with its contemporary fireplace, runs into the dining area and a vaulted kitchen, and all three look out to the patio and a pool with an electronic cover. The kitchen has a six-burner Wolf range, a Sub-Zero refrigerator, two Bosch dishwashers and an adjoining bar with a wine fridge. Just steps from the pool, a cabana with vaulted ceilings and sliding doors has a sitting area, a wet bar and a full bathroom.
One primary suite is on the first floor, down a quiet hall, with cathedral ceilings and a bath that has a soaking tub and heated floors. Upstairs are a second primary suite and two guest rooms with their own baths, and a back staircase off the mudroom leads to a separate bedroom suite above the garage. The lower level adds a living space with a TV, a game space and a custom bunk room. The property last sold for $6.1 million in 2019.
Erin Wilson of Fisher Real Estate was the listing agent. Chandra Miller of Maury People Sotheby’s International Realty represented the buyer.
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No. 3 — $7,350,000 · 2 Noras Lane, Edgartown, Massachusetts
The week’s largest lot, 1.80 acres, came with 2 Noras Lane in Edgartown’s Nora’s Meadow neighborhood, close to downtown Edgartown, South Beach and the Katama bike path. The custom shingle home was built in 2014 and has five bedrooms, five bathrooms and 4,389 square feet on three stories.
French doors carry the living room out to the pool patio. Outside are a large pool, an outdoor kitchen, a stone patio and a pool house with a full bath, along with gardens and an outdoor shower. The primary suite is on the first floor, with its own outdoor sitting area tucked into the landscaping, and the finished lower level has a media room and space for a pool table. The two-car garage has unfinished space above it that, the listing says, could become a guest house. The property last sold for $2.4 million in 2015.
The home went under contract 10 days after it was listed and sold for $150,000 above its $7.2 million asking price. Alyssa M Halisky of Wallace & Co. Sotheby’s International Realty was the listing agent.
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No. 4 — $4,400,000 · 135 Surfside Rd, Nantucket, Massachusetts
At 135 Surfside Road on Nantucket, the outdoor space is the main event. A heated saltwater pool measuring 17 by 38 feet sits below an expansive deck, and a bluestone patio surrounds the pool, the spa and a firepit set beneath a pergola. The 0.57-acre property has mature landscaping and pasture views, and the dining room opens to a covered porch that faces east.
Built in 1981 and fully renovated, the home has four bedrooms and three bathrooms in 1,954 square feet. Two of the bedrooms are on the main level, and the kitchen has been updated with high-end appliances. Upstairs, the primary suite has a renovated bath with Italian tile and a heated floor, and a second bedroom opens to a studio room above the garage. It sold furnished. The property last sold for $1.14 million in 2010.
The home went under contract 14 days after it was listed. Penny Dey of Atlantic East Nantucket Real Estate was the listing agent, and Brian Sullivan of Fisher Real Estate represented the buyer.
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No. 5 — $4,250,000 · 222 Barcliff Avenue, Chatham, Massachusetts
The newest home on the list, 222 Barcliff Avenue in Chatham, is a farmhouse built in 2026 by Morgan and Sons, within walking distance of town, the fish pier, the beach and baseball games. On a level 0.47-acre lot, the two-story home has four bedrooms, each with a private bath, along with six bathrooms in all and 3,980 square feet. The exterior mixes clapboard and shingle siding.
The primary suite, a study and the kitchen and dining area are on the first floor, and the living room has vaulted ceilings and a large slider looking out to the pool and patio. A detached outbuilding includes a one-car garage and a 252-square-foot cabana with a living room, a full bath and a wet bar.
The home sold at its full asking price. Lori L Fanning Smith of Compass Massachusetts, LLC was the listing agent, and The Bohman Hartung Group of Gibson 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, November 1, 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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