Three of the five highest-priced home sales reported in Lower Fairfield County, Connecticut for the week ending November 8, 2026 were in Greenwich, with one each in Darien and Old Greenwich. Together the five sold for $35.89 million.
The group spans more than a century of building, from a Victorian in Old Greenwich to a home finished only this year, and it includes four single-family homes and one condominium. Along the way are a historic estate in the Tokeneke section of Darien, a property beside conservation land and a townhome in downtown Greenwich.
No. 1 — $12,000,000 · 7 Parsonage Rd, Greenwich, Connecticut
Completed in 2026, the brick Colonial at 7 Parsonage Road in Greenwich sold for $12 million. With 10,286 square feet of living space it is both the newest and the largest home in this Top 5. It sits behind an electric gate on a level, parklike lot of 1.12 acres, and it has six bedrooms, eight bathrooms (six full and two half), six fireplaces and an elevator serving every floor.
The principal rooms include a great room with a vaulted ceiling and a fireplace, as well as formal living and dining rooms. The kitchen has an island, custom cabinetry finished inside in walnut and Sub-Zero Designer Series appliances, and there is a butler’s pantry with a wet bar. A floating glass staircase climbs to the upper floors. The primary suite has its own fireplace and coffee bar, two boutique-style dressing rooms and a marble bath with a radiant heated floor, a steam shower and a soaking tub. Three more bedrooms on that floor each have their own bath, and a covered deck on the second floor looks out over the back of the property. On the third floor are another bedroom suite, a room that can serve as an office or a sixth bedroom, and a walk-in cedar closet.
The finished lower level is built for entertaining, with a great room and full bar, a humidity-controlled wine room, a home office with built-ins, and a gym with 11-foot ceilings that is ready for a golf simulator. Outside, a heated 20-by-40-foot pool has an automatic cover, and two covered terraces overlook the lawn. A 300-foot stone wall and motorized gates enclose the grounds, which are planted with 100 arborvitae. Inside the gates, a paver motor court has room for more than 12 cars, in addition to a heated three-car garage. The home is close to downtown Greenwich. The property last sold before the current house was built, for $2.605 million in 2023.
Leslie McElwreath of Sotheby’s International Realty was the listing agent for the week’s top sale, and Julie Church of Houlihan Lawrence represented the buyer.
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No. 2 — $7,340,000 · 16 East Trail, Darien, Connecticut
Built in 1908 in the Tokeneke Association in Darien, the shingle-and-clapboard Colonial at 16 East Trail sold for $7.34 million. The listing says it was among the first homes built in the enclave. Architect Peter Pennoyer renovated it with an eye to its history, designer Katie Ridder did the interiors, and landscape architect Janice Parker designed the grounds.
The home has nine bedrooms and 10 bathrooms, seven full and three half, the most bedrooms and bathrooms of any home in this Top 5. It also has five fireplaces and 8,188 square feet of living space on 2.89 acres. A carriage house is set up as a guest residence with two bedrooms, a bath and a kitchen of its own.
Outdoors there are gardens, fruit trees, stone walls and terraces, along with a heated in-ground saltwater pool of gunite. The property has beach access, and the water is within walking distance. It last sold for $5.275 million in 2010.
Ashley Dineen of Compass Connecticut, LLC was the listing agent, and Richard Higgins Jr of Higgins Group Real Estate represented the buyer. It was the first of three listings in this Top 5 for Compass Connecticut, LLC, which also listed the homes in third and fifth place.
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No. 3 — $6,800,000 · 74 Rock Maple Rd, Greenwich, Connecticut
At 4.08 acres, 74 Rock Maple Road in Greenwich has the largest lot in this Top 5, and it adjoins conservation land. The brick Georgian-style home, built in 1997, sold for $6.8 million. It last sold for $5.65 million in 2022.
The grounds have a pool, a tennis court, open lawns and mature landscaping, and a terrace with a gas grill. The recreation continues indoors, where the home has a private basketball court, a gym and a wine cellar. Its 8,911 square feet include five bedrooms, eight bathrooms (six full and two half) and seven fireplaces, along with built-in bookcases and a back staircase. The kitchen is new, and the bathrooms have been renovated. The home is close to town schools, parks and transportation.
Jenny Allen of Compass Connecticut, LLC and Kristen Studwell, also of Compass Connecticut, LLC, were the listing agents. Jeff Jackson of Corcoran Centric Realty LLC represented the buyer.
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No. 4 — $5,000,000 · 8 Highview Ave, Old Greenwich, Connecticut
The oldest home in this Top 5 is a shingled Victorian built in 1895 at 8 Highview Avenue in Old Greenwich, which sold for $5 million. A wraparound porch runs around it, and inside, the renovated home pairs high ceilings with newly updated interiors.
It has six bedrooms, seven bathrooms (five full and two half) and 4,007 square feet of living space, with flexible rooms that can be used as a gym, a playroom and offices. The level lot measures 10,454 square feet and has a terrace and a deck, and there is a two-car garage. The home is near the Metro North train, Old Greenwich village, restaurants and schools, and it is close to Innis Arden Golf Club.
Megan Epand of Houlihan Lawrence and Joan Epand of Houlihan Lawrence were the listing agents. Carolyn Petersen of Compass Connecticut, LLC represented the buyer.
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No. 5 — $4,750,000 · 80 Milbank Ave Unit A, Greenwich, Connecticut
The one condominium in this Top 5 is a townhome at 80 Milbank Avenue, Unit A, three blocks off Greenwich Avenue in downtown Greenwich. It went under contract four days after it was listed and sold for $4.75 million, $555,000 above its asking price of $4.195 million.
Built in 2017, the townhome has 3,660 square feet of living space, four bedrooms and five bathrooms (four full and one half), with an elevator between floors. A double-height foyer opens to an open floor plan with high ceilings and many windows. On the second floor, the primary suite has a tray ceiling, two walk-in closets and its own bath, and two guest bedrooms each have their own bathroom. The finished lower level has a family room with a fireplace, another guest bedroom, a full bath, a gym and laundry. There is an attached one-car garage, and the home has a private terrace and garden. It last sold for $2.725 million in 2022.
Kevin Sneddon Private Client Team at Compass of Compass Connecticut, LLC was the listing agent, giving the brokerage its third listing in this Top 5. Alexander Chingas of Coldwell Banker 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 8, 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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