These were the five highest-priced home sales reported in Mid-Fairfield County, Connecticut for the week ending October 25, 2026, and together they came to $16.514 million. Every one was a single-family home, and every price landed between $3 million and $3.9 million.
Westport accounted for three of the sales, all in Coleytown, two of them on North Avenue. The other two were in Fairfield’s Beach neighborhood. The group spans nearly eight decades of building, from a Colonial dating to 1937 to a Cape Cod completed in 2016, and William Pitt Sotheby’s Int’l was the listing brokerage on three of the five.
No. 1 — $3,900,000 · 278 North Avenue, Westport, Connecticut
The top sale of the week was a shingle-style Colonial at 278 North Avenue in Westport’s Coleytown neighborhood, which sold for $3,900,000. Built in 2006, it is the largest home in this group, with 9,525 square feet of living space, six bedrooms and nine bathrooms, seven full and two half. Its level, landscaped acre borders the 39-acre Newman Preserve.
The home has 10-foot ceilings and has six fireplaces, along with extensive custom millwork. The kitchen is built around two islands, with Thermador and Wolf appliances, a walk-in pantry and a separate butler’s pantry with a wet bar. In the primary suite, a sitting room set in a turret sits alongside a fireplace and two walk-in closets. A private suite over the garage adds room for guests, and there is a wine cellar along with a three-car attached garage.
The finished lower level, heated and cooled, has its own fireplace and walks out to the grounds. Outside are a heated gunite pool behind a fence, stone patios, a fire pit, a gazebo and a covered porch with a fireplace of its own. The property last sold for $2.799 million in 2014.
Cyd Hamer of William Pitt Sotheby’s Int’l was the listing agent and also represented the buyer, putting the same agent on both sides of the sale.
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No. 2 — $3,350,000 · 4 Charcoal Lane, Westport, Connecticut
At 4 Charcoal Lane, on a cul-de-sac in Coleytown, a farmhouse-style Colonial and a post-and-beam barn share 2.02 acres that border open space, with views out over a 7-acre nature preserve. The property sold for $3,350,000, and its 2.02 acres make it the largest lot among the five.
The main home dates to 1965 and has been extensively renovated. It has five bedrooms, five bathrooms (four full and one half) and 6,015 square feet. A 14-foot island of Calacatta marble anchors the kitchen, which sits near a family room with two fireplaces, and the living room’s tray ceiling was designed with a piano in mind. Upstairs, the primary suite has a spa-style bath.
The barn, built by Country Carpenters and reached by a breezeway with barn doors, has one bedroom, along with 20-foot ceilings, heated floors, a full kitchen and retractable doors that open it to the yard. Outside, a heated gunite pool and hot tub with a waterfall sit beside a blue granite patio, and a porch for entertaining has built-in heaters, a see-through fireplace and an outdoor television. There is also a four-car garage, a whole-house backup generator and a chicken coop wired for electricity. The property last sold for $1.175 million in 2004.
Carol Langeland of William Pitt Sotheby’s Int’l was the listing agent, and Robert Appell of Coldwell Banker Realty represented the buyer.
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No. 3 — $3,260,000 · 297 Lalley Boulevard, Fairfield, Connecticut
The newest home in the group stands at 297 Lalley Boulevard in Fairfield’s Beach neighborhood. Custom built in 2016, the four-bedroom Cape Cod sold for $3,260,000, above its asking price of $2.95 million, after going under contract 11 days after it was listed.
The kitchen centers on an island cut from a single slab of Danby marble, with two dishwashers and generous storage. It opens with the family room toward a fireplace that serves both indoors and out, and the pool and patio lie past it. A third-floor room the listing calls the crow’s nest has a full bath and looks out toward Long Island Sound. The home has five bathrooms, four full and one half, and 3,653 square feet on a 9,147-square-foot lot, the smallest among the five, in a water community within easy reach of the beach, the train and town.
The property last sold for $707,500 in 2011, before the current home was built.
Cindy Raney of Coldwell Banker Realty was the listing agent, and Jeannette Floto of Compass Connecticut, LLC represented the buyer.
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No. 4 — $3,004,000 · 108 Colonial Drive, Fairfield, Connecticut
A center-hall Colonial at 108 Colonial Drive, also in Fairfield’s Beach neighborhood, went under contract six days after it was listed and sold for $3,004,000, above its asking price of $2.795 million. Stone walls and landscaped grounds frame the level corner lot of 0.26 acres.
Built in 2003, the shake-sided home has 3,625 square feet, five bedrooms and four bathrooms, three full and one half. On the main floor, 9-foot ceilings run over formal and casual living and dining areas and a kitchen made for entertaining, with a large mudroom and a half bath by the door to the garage, which has room for two cars. All five bedrooms are upstairs, along with a laundry room. The primary bath has a soaking tub, a shower and a sauna, and built-ins and wainscoting run through the home. The property last sold for $1.48 million in 2020.
Nancy Freedman of William Pitt Sotheby’s Int’l was the listing agent, giving the firm three of the five listings this week, and Laura Hoglund of Berkshire Hathaway NE Prop. represented the buyer.
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No. 5 — $3,000,000 · 240 North Avenue, Westport, Connecticut
Known as Meadow Wood, the estate at 240 North Avenue in Coleytown sold for $3,000,000. The Colonial was built in 1937, the oldest home among the five, and has since been remodeled and expanded. It sits on 1.92 wooded acres on a corner lot, fenced and screened by privacy trees, with gated driveways leading to the main home and to a barn of about 2,447 square feet.
Inside, the home has five bedrooms, five bathrooms (four full and one half) and 3,778 square feet. A living room running front to back has a bay window and two doors to a porch overlooking the grounds. The great room joins a kitchen with a large island and Thermador appliances to a casual dining area, the dining room and a family room whose wall of folding glass doors opens to the outdoors. A bedroom suite with its own entrance is on the main floor. Upstairs, the primary suite has a tray ceiling, a fireplace, a walk-in dressing room and a balcony across much of the back of the home. A patio runs along the heated gunite pool.
Douglas Bross of Coldwell Banker Realty was the listing agent, the firm’s second listing in this week’s top five after 297 Lalley Boulevard, and John Raus of Berkshire Hathaway NE Prop. represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 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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