The five highest-priced home sales reported in Fairfield County for the week ending October 11, 2026, came from three towns: two in New Canaan, two in Darien and one in Greenwich. Together they totaled $24.45 million.
The group runs from a renovated 1938 Colonial to a 2004 home with an elevator and a wine room. Houlihan Lawrence agents listed three of the five homes.
No. 1 — $7,000,000 · 30 Oenoke Lane, New Canaan, Connecticut
The week’s highest-priced sale was a California Contemporary in New Canaan, and its story begins with an architect and a family. James Evans, a New Canaan modernist who studied under Louis Kahn and worked with Paul Rudolph, designed the home in 1996 for the McKays, the clients for whom he had already designed a mid-century modern residence in town in 1959. The family came back to him nearly four decades later for the home they planned to live in next, and it was completed in 1997.
The home sits on 4.85 level, landscaped acres that border open space, with a pond, a waterfall, mature trees, native plantings and winding paths. The listing says the grounds are recognized in the Smithsonian’s Gardens of America. Walls of glass open the rooms to the landscape, and the property also has terraces, a patio, a balcony and stone walls. Downtown New Canaan and the train station are a short walk away.
Inside, the home has five bedrooms, six bathrooms, two fireplaces and 7,259 square feet of living space. The primary suite is on the first floor, an elevator serves the home, and there are several rooms that can work as offices. A separate guest suite has its own living room, kitchenette, full bath and entrance while still connecting to the main second level. A circular driveway leads to an attached three-car garage.
The home sold for $7,000,000. During negotiations, the buyer and seller agreed to add two more parcels of 1.66 acres and 1.03 acres, and the price covers the residence and all three parcels.
Susan C. Leone and Danna Rogers of Higgins Group Bedford Square were the listing agents, and Melissa Rwambuya of William Raveis Real Estate represented the buyer in the highest-priced sale of the week.
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No. 2 — $5,250,000 · 57 Clapboard Ridge Rd, Greenwich, Connecticut
In Greenwich’s Mid-Country, a 1955 clapboard Colonial on 2.11 acres went under contract 13 days after it was listed and sold for $5,250,000, $155,000 above its $5.095 million asking price. The property last sold for $2.8 million in 2001.
The grounds are parklike, with gardens, a broad lawn, a covered terrace and a private pool. The home has six bedrooms, five bathrooms, four fireplaces and 5,416 square feet. Its eat-in kitchen, with an island and a pantry, opens to the family room, and there is also a den and an office. The primary suite has a spa-style bath, and a back staircase links the floors. Schools, the train and the shops and restaurants of Greenwich Avenue are close by.
Maria Kelce Crowley of Houlihan Lawrence was the listing agent, and Max Metalios, also of Houlihan Lawrence, represented the buyer. The sale was one of three homes in this Top 5 listed by Houlihan Lawrence agents.
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No. 3 — $4,675,000 · 85 Harrison Avenue, New Canaan, Connecticut
The newest home in the group, and the largest at 8,070 square feet, went under contract one day after it was listed. The 2004 Colonial on Harrison Avenue, an in-town New Canaan address, sold for its full asking price of $4,675,000.
It sits on just over half an acre and has six bedrooms and eight bathrooms, more than any other home in this Top 5. An elevator connects the floors. The main level centers on an open kitchen with a large quartz island, double sinks, custom built-ins and a new Wolf range, with clear views through the breakfast room and family room to the deck. The living and family rooms have detailed millwork, the office has a coffered ceiling, and two mudrooms sit side by side.
The primary bedroom has two walk-in closets and a bathroom redone in 2026 with quartz and Rohl fixtures, and most of the other bathrooms were renovated the same year. The finished third level has room for a guest suite with a full bath, a gym, a recreation room or another office. The walk-out lower level has a wine room and a wet bar. Outside are a gunite pool, tiered stone patios, a fire pit and evergreen screening.
Wendy Werneburg and Hannelore Kaplan of William Raveis Real Estate were the listing agents. Nadia Kachwaha of KW Legacy Partners represented the buyer.
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No. 4 — $4,000,000 · 32 Birch Road, Darien, Connecticut
The oldest home in this Top 5 was built in 1938 and has since been completely renovated. Nordic Custom Builders redid the Darien Colonial, putting in new windows and doors, wide white oak floors, a cedar roof, custom moldings and new landscaping. The home on Birch Road has beach access, four bedrooms, five bathrooms and 4,695 square feet on 0.77 acres.
French doors run from the formal living and dining rooms out to a bluestone patio and the pool. The office has a vaulted shiplap ceiling and its own marble wet bar with a wine refrigerator. The kitchen has Thermador appliances, a Sub-Zero refrigerator and freezer, banquette seating and a second wet bar, and it opens to a screened porch whose plexiglass panels can be put in for cooler months. The family room has oversized windows, built-ins and a fireplace, and a sound system runs through the home.
The primary suite has a large walk-in closet and a marble bath with a steam shower and heated floors. The finished lower level has a full bath and two large rooms that could serve as a gym, a media room or a fifth bedroom. Out back are a heated gunite pool, a hot tub and a pool house. The property last sold for $1.859 million in 2011.
The home went under contract 24 days after it was listed and sold for $4,000,000, just above its $3.995 million asking price. Deb Hidy of Houlihan Lawrence was the listing agent, and Ingrid Hess of Compass Connecticut, LLC represented the buyer.
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No. 5 — $3,525,000 · 18 Phillips Lane, Darien, Connecticut
Phillips Lane is a cul-de-sac in Darien, and the 1941 Cape Cod at No. 18 went under contract 11 days after it was listed. It sold for $3,525,000, which was $275,000 above its $3.25 million asking price. The property last sold for $1.615 million in 2013.
The home has five bedrooms, four bathrooms and 4,567 square feet on just over half an acre. Its center is a great room with a vaulted ceiling, a gas fireplace and a wet bar that opens to the outdoor living area. The kitchen has quartz counters and white oak cabinetry, and meals are taken in a sunroom with a built-in banquette or in a formal dining area. The living room has a wood-burning fireplace.
Upstairs, the primary suite has a walk-in closet and a bath with a double shower. Outside, a large deck has a hot tub, an outdoor kitchen and a gas fire pit, and stone steps go down to a flat, private yard.
Amanda Spatola of Houlihan Lawrence was the listing agent, giving the firm its third listing in this week’s Top 5. Caroline Shen of Corcoran Centric 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 11, 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 Fairfield County market page.
