Three Greenwich properties, a beachfront home in Fairfield and a newly built home in Westport were the highest-priced home sales reported in Fairfield County for the week ending October 18, 2026. Together the five sold for $54.055 million.
The two leading sales came within $5,000 of each other, and the group spans nearly a century of building, from a Colonial that dates to 1929 to a home completed this year. Lots range from 0.32 acres on the beach in Fairfield to 6.11 acres in Greenwich.
No. 1 — $18,000,000 · 36-38 0 Game Cock Rd, Greenwich, Connecticut
The top sale of the week was Farwell’s Island, a private island in the Byram section of Greenwich that is reached by its own bridge. It sold for $18 million.
The main home is a cedar-clad Shore Colonial built in 1936. It has seven bedrooms, six bathrooms, two fireplaces, a back staircase and 6,166 square feet of living space. A separate guest house adds three more bedrooms, each with its own bath, in 3,238 square feet. The grounds cover 1.15 acres, with gardens and a parklike setting.
Life here is organized around Long Island Sound. The property has deep water and protected dockage for several boats, along with swimming piers and a private beach. A boat house and patios for entertaining sit on the back side of the island, and the property also has a terrace, a deck, a balcony and an outdoor shower. There is a five-car garage.
The home went under contract 14 days after it was listed. Brett Smith of Brown Harris Stevens CT, LLC was the listing agent with Dianna Smith, also of Brown Harris Stevens CT, LLC, and Evangela Brock of Douglas Elliman of Connecticut represented the buyer.
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No. 2 — $17,995,000 · 19 Khakum Dr, Greenwich, Connecticut
Set on 6.11 acres inside the Khakum Wood Association, with a stream on the property, this European-style estate was the largest home in this week’s Top 5 and sat on the largest lot. Built in 2001, it is finished in limestone, fieldstone and stucco under a graduated slate roof.
Inside are 15,216 square feet of living space, seven bedrooms and 10 bathrooms, eight full and two half, along with six fireplaces, high ceilings and a back staircase. The full basement is finished. There are stone terraces on every level, overlooking broad, level lawns. Outdoors there is a pool, a bocce court, a courtyard and a gas grill, and a garage apartment gives guests or staff their own quarters. The garage has room for seven cars, the most of the five.
The property last sold for $4 million in 1999, before the current home was built.
It sold at its full asking price of $17.995 million. Deborah Ward of Sotheby’s International Realty and Kim Conrad of Sotheby’s International Realty were the listing agents, and Amanda Miller of Houlihan Lawrence represented the buyer.
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No. 3 — $7,500,000 · 55 Calhoun Dr, Greenwich, Connecticut
The oldest home in this week’s group, 55 Calhoun Drive in Rock Ridge dates to 1929 and has since been completely rebuilt. The Colonial, finished in wood siding and stucco, stands on a cul-de-sac in the Calhoun Drive Association. The home is elevated on 1.42 acres of level, parklike grounds with gardens and specimen trees, close to downtown Greenwich.
The home has six bedrooms, 10 bathrooms, four fireplaces and 8,273 square feet of living space. A grand foyer leads to the main rooms, and a wide terrace overlooking the lawn and gardens can be reached from the breakfast room, the sunroom and a family room with a coffered ceiling. The primary suite has a sitting room that opens to a private balcony, walk-in closets and two marble Waterworks bathrooms, and a separate guest suite gives visitors their own space.
The garden level is given over to recreation, with a wine cellar, a media room, a wet bar, a gym with a full bath and a playroom that opens to a covered terrace. The main home has a three-car garage, and a two-story carriage house has room for two more cars.
It sold for $7.5 million. The property last sold for $2.758 million in 2003. Barbara Wells of Houlihan Lawrence was the listing agent, and Julie Church, also of Houlihan Lawrence, represented the buyer.
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No. 4 — $5,410,000 · 1657 Fairfield Beach Road #1657, Fairfield, Connecticut
On Fairfield Beach Road, this 2015 Colonial has direct frontage on the beach, and its water views take in Penfield Lighthouse and the Long Island ferry. Its shingle and shake exterior is set on 0.32 acres, the smallest lot in the Top 5.
The home is built for the beach. A covered porch with a glass fence looks over the heated in-ground pool, which is edged in limestone, and out to the beach beyond. The home has seven outdoor decks, and an elevator runs up from the garage. Inside, a two-story elliptical staircase was designed to suggest a seashell.
The main kitchen is finished in quartzite, with Sub-Zero refrigeration and a Wolf double oven, and a second galley kitchen has its own dishwasher, sink and refrigerator plus a built-in banquette for dining with a view of the water. The home has four bedrooms, six bathrooms, two fireplaces, 3,855 square feet of living space and a two-car garage. An office is on the first floor, and the primary suite has his and hers baths and sliding doors to a large deck.
The home went under contract six days after it was listed and sold for $5.41 million. Joanne K. Landino of Berkshire Hathaway NE Prop. and Nancy Thorne of Berkshire Hathaway NE Prop. were the listing agents, and Rose Ciardiello of William Raveis Real Estate represented the buyer.
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No. 5 — $5,150,000 · 4 Sycamore Drive, Westport, Connecticut
The newest home in this week’s Top 5 was built in 2026 by CCO Habitats on a secluded one-acre lot on a cul-de-sac in the Hunt Club area of Long Lots in Westport. It sold for $5.15 million. The property last sold for $1.3 million in 2025, before the current home was built.
The design is organic modern, with Hardiplank-type siding outside and tilting European windows and sliding doors that bring in daylight. Its 8,935 square feet of living space are spread across three finished levels, with 10-foot ceilings on the first floor. The home has six bedrooms, including a guest bedroom with a full bath on the first floor, and eight bathrooms. There are two offices, one on the first floor and one in a private wing of the second floor with its own staircase, and the home has three wet bars and a dry bar.
The finished lower level is a walkout and can serve as a pool house, with a full bath, a second laundry room and space for entertaining. The saltwater pool measures 20 by 40. A whole-house generator, an EV outlet and a three-car attached garage round out the property.
Maryann Levanti of Higgins Group Bedford Square was the listing agent, and Linda Skolnick 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, October 18, 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.
