The five highest-priced home sales reported in Lower Fairfield County, Connecticut for the week ending November 1, 2026, came to a combined $40.37 million. Three of the homes are in Greenwich, one is in Old Greenwich and one is in New Canaan, and their lots run from 0.48 acres to five acres. Agents from Houlihan Lawrence listed three of the five, and agents from Sotheby’s International Realty listed the other two.
No. 1 — $10,000,000 · 887 Weed Street, New Canaan, Connecticut
The week’s top price, $10 million, was paid for a five-acre estate on Weed Street in New Canaan. The property is across from Irwin Park and borders the trail network of the New Canaan Nature Center, while the village, the train and the schools remain within easy reach.
The main residence is a shingle-sided Colonial built in 2000 by Hobbs Construction, with interiors first done by the designer Alexa Hampton. It has five bedrooms, six full and two half baths, six fireplaces and 11,184 square feet of living space, the largest of the five homes. The rooms are finished with custom millwork, upholstered walls and marble baths, and radiant heat warms the floors. There is also a sound system and a partially finished basement.
A separate guest house of 1,450 square feet has three bedrooms and its own generator, giving family or long-term visitors a place of their own. The level, landscaped grounds have a gated entrance, stone walls, gardens and full deer fencing. A heated in-ground pool and spa, a pool house and a tennis court round out the property, which last sold in 2018 for $5.29 million.
The home went under contract five days after it was listed and sold just above its $9.975 million asking price. Taylor Tait of Houlihan Lawrence was the listing agent, and Jill Abolt, also of Houlihan Lawrence, represented the buyer. It was the first of three homes in this Top 5 listed by Houlihan Lawrence agents.
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No. 2 — $9,500,000 · 50 Zaccheus Mead Ln, Greenwich, Connecticut
At the heart of this home in the Rock Ridge neighborhood of Greenwich is a barn from the 1800s that was moved here from New Hampshire. Records date the home to 1965, the earliest year built among the five, and the home was gut-renovated in 2015.
The great room rises to a high, wood-beamed ceiling and takes in plenty of daylight. The home also has a kitchen with an island and a family room. There are five bedrooms, six full baths and one half bath across 5,953 square feet, along with three fireplaces. The primary suite has two baths of its own, and a separate two-room suite works well for an au pair or in-laws.
The clapboard and stone home sits on two level acres edged with stone walls. Dogwoods and Japanese maples grow on the landscaped grounds, and the property also has a brook, a studio and a greenhouse. Outside, a terrace accompanies a pool with a waterfall. The property last sold in 2014 for $5.09 million.
The home went under contract seven days after it was listed and sold for $9.5 million, $1.5 million above its $8 million asking price, tying it with the Old Greenwich sale that follows. Sally Maloney of Houlihan Lawrence was the listing agent. Leslie McElwreath of Sotheby’s International Realty represented the buyer.
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No. 3 — $9,500,000 · 203 Shore Road, Old Greenwich, Connecticut
The other $9.5 million sale, and the newest home in this Top 5, is in Lucas Point, a private waterfront association in Old Greenwich whose residents share a sandy beach, a dock and boat storage. The coastal shingle-style home was designed by the Greenwich architect Steven Mueller and completed in 2016. It stands on a level lot of 0.48 acres, the smallest of the five, which can be reached from both Shore Road and Middle Way. Tod’s Point, with its trails, beaches and views across Long Island Sound, is just steps away.
The home has nearly 2,000 square feet of covered porches. The ones on the front of the home look out to the sunrise over Long Island Sound, and those facing west catch the evening sunset. Visitors arrive under a porte-cochere into a foyer where a sweeping staircase climbs beneath a coved ceiling on the third floor. French doors open the front and rear of the home to the outdoors.
The kitchen is open to the family room, the living room has a coffered ceiling, and the study has a fireplace and built-ins. The primary suite has a porch of its own with water views, two walk-in closets and a marble bath. Three more bedrooms with their own baths and a laundry room are on the second floor. Up on the third floor, an elevated porch looks out over the Sound and the boats passing through it. The finished lower level has high ceilings, an entertainment room, a fitness room and a fifth bedroom with its own bath. In all the home has five bedrooms, five full baths and one half bath, 6,723 square feet and three fireplaces, with a detached two-car garage.
Privet hedges and hydrangeas frame the landscaped grounds, which include a level lawn and an organic garden planted in raised beds. The property last sold in 2012 for $2.7 million, before the current home was built. Tracey Koorbusch of Sotheby’s International Realty was the listing agent, and Shelly Tretter Lynch of Compass Connecticut, LLC represented the buyer.
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No. 4 — $6,750,000 · 23 Wyckham Hill Ln, Greenwich, Connecticut
This brick Georgian home on Wyckham Hill Lane in Greenwich sold for $6.75 million. Built in 1989, it has six bedrooms, the most of any home in this Top 5, along with five full baths, three half baths, five fireplaces and 8,330 square feet of living space.
Formal rooms sit alongside a library, a family room and a kitchen with a marble island. The primary suite includes a sitting room and its own bath. Back stairs, a wet bar, cedar closets and central vacuum are among the practical touches, and the full basement adds more room.
The 2.16 level acres are set up for life outdoors. There is a pool and spa, terraces, an outdoor kitchen with a pizza oven and grills, and a fire pit. The property also has a greenhouse, organic gardens and a three-car garage. The property last sold in 2016 for $3.625 million.
Eva Penson of Sotheby’s International Realty was the listing agent, one of two homes in this Top 5 listed by agents from that brokerage. Karen Colella of Compass Connecticut, LLC represented the buyer.
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No. 5 — $4,620,000 · 739 Lake Avenue, Greenwich, Connecticut
Set back on 2.38 acres in the Midcountry area of Greenwich, this Colonial on Lake Avenue sold for $4.62 million. The clapboard and brick home was built in 1978 and is about ten minutes from downtown Greenwich, its shops and restaurants, and the train.
Inside, the home keeps its period detail in moldings and archways, and the rooms are arranged for both family life and entertaining. It has five bedrooms, five full baths and one half bath, four fireplaces and 5,281 square feet of living space. The landscaped yard has a heated in-ground pool, a deck and a patio, and a cabana bath attached to the home serves swimmers. Part of the lot is wetland. The property last sold in 1999 for $1.925 million.
The home sold above its $4.5 million asking price. Carissa Larriuz of Houlihan Lawrence was the listing agent, giving that brokerage its third listing in this Top 5, and Jen Turano of Compass Connecticut, LLC 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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