The five highest-priced home sales reported in Mid-Fairfield County, Connecticut, for the week ending November 8, 2026, came to a combined $18.82 million. All five were single-family homes, spread across Westport, Norwalk, Fairfield and Weston, which had two of the sales.
The group ranged from a Colonial built in 1950 to one finished in 2003, and in setting from a gated waterfront enclave to wooded acreage across from a country club.
No. 1 — $6,350,000 · 69 Beachside Avenue, Westport, Connecticut
The week’s top sale was 69 Beachside Avenue in the Greens Farms section of Westport, which sold for $6.35 million. The property sits behind gates on 4 acres, the largest parcel of the five, and is reached by a long drive.
The home, built in 1982, blends Contemporary and Mediterranean design in stone and stucco. Inside, high ceilings and expanses of glass look out over the grounds, and a chef’s kitchen anchors the main living spaces, opening to both formal and casual rooms. The home has six bedrooms, seven bathrooms, four fireplaces and 6,585 square feet of living space, and its primary bath has just been redone as a spa-style retreat.
Much of the appeal is outdoors. The grounds include a heated saltwater pool and spa, broad terraces and a full Har-Tru tennis court, as well as a gazebo, rolling lawns and mature plantings. It is a waterfront property, and a pond is among its features. Westport’s beaches, the Longshore Club and downtown are all nearby, and the property has direct access to Greens Farms Academy.
John Raus of Berkshire Hathaway NE Prop. was the listing agent, and Sarah Fair of William Raveis Real Estate represented the buyer in the highest-priced sale of the week.
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No. 2 — $4,750,000 · 3 Canfield Crossing, Norwalk, Connecticut
At 3 Canfield Crossing, in the Marvin Beach area of Norwalk, the water is the point. The shingle-sided Colonial stands in a gated waterfront enclave tucked behind Shorehaven Country Club, and from almost every room there are views of the tide coming and going. The record also lists views of the golf course.
Built in 2003, it is the newest home in this group, and at 8,947 square feet it is also the largest, set on the smallest lot of the five, a 0.32-acre corner parcel. A NanaWall folds open to join the newly renovated kitchen and living areas to a broad waterfront terrace and an infinity-edge pool with a spa. Kayaks and paddleboards can be launched right from the backyard.
The home has six bedrooms, each with its own bath, seven bathrooms in all and four fireplaces. An elevator connects its floors, and the finished lower level is heated and cooled and has walk-out access. Two parts of the home can work as separate guest or au pair quarters. The property last sold for $4.2 million in 2005, and this time it sold for $4.75 million.
Carly Woodard of William Pitt Sotheby’s Int’l was the listing agent, and Aaron Greenberger, also of William Pitt Sotheby’s Int’l, represented the buyer.
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No. 3 — $3,500,000 · 4 Good Hill Road, Weston, Connecticut
Few homes come with a museum. The property at 4 Good Hill Road in Lower Weston, which sold for $3.5 million, includes a private art museum of 6,500 square feet that the owner built to display the art collection of the owner’s father, along with a fully renovated barn.
The home itself dates to 1970 and has been renovated, mixing Colonial and Modern design with cedar vertical siding and block on the outside and an open floor plan within. It has three bedrooms, the fewest of the five, along with three bathrooms, a fireplace and 8,500 square feet of living space. The landscaped 3.25-acre corner property includes cleared ground as well as wetlands, a patio and beach access.
The property last sold for $410,000 in 2013, 13 years ago. Kim Harizman of Compass Connecticut, LLC was the listing agent, and Donald W. Fish of D.W. Fish Real Estate represented the buyer.
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No. 4 — $2,122,700 · 50 Brookbend Road, Fairfield, Connecticut
The oldest home in the group, 50 Brookbend Road in Fairfield’s Winton Park Association, was built in 1950 and sold for $2,122,700. The cedar-shake Colonial sits on 1.78 level acres, close enough to walk into town. The grounds include gardens and a stone wall.
Inside, a grand staircase rises from the foyer, and wide-plank hardwood floors and fine millwork run through the rooms. The living room steps down and is lined with paneling and built-ins around a wood-burning fireplace. French doors lead from the formal dining room to a private patio, while the eat-in kitchen flows into a bright family room with a second fireplace and its own French doors to a brick patio with a waterfall.
The home has five bedrooms, four full baths and a half bath, and 4,512 square feet of living space. The primary suite is upstairs with three other bedrooms. A separate guest suite, with its own entrance, a vaulted ceiling, a fireplace and a full bath, includes the fifth bedroom. An attached three-car garage completes the property.
The home went under contract 25 days after it was listed and sold above its $2.05 million asking price. Kate Cacciatore of William Raveis Real Estate was the listing agent, and Andrea M. Viscuso of Compass Connecticut, LLC represented the buyer.
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No. 5 — $2,100,000 · 10 Weddington Lane, Weston, Connecticut
The second Lower Weston sale of the week, 10 Weddington Lane, sold for $2.1 million, $250,000 above its $1.85 million asking price. Together the two Weston sales came to $5.6 million.
The all-brick Colonial, built in 1992, sits on a cul-de-sac across from the grounds of Aspetuck Valley Country Club, on 2.03 landscaped, partly wooded acres reached by a new circular drive. Its exterior has copper accents, bay windows, several chimneys and a varied roofline.
A floating staircase rises from the foyer. The living room and family room both have cathedral ceilings and fireplaces, and the library, also under a cathedral ceiling, has a third fireplace, built-ins and a bay window. The dining room has a tray ceiling, and the updated kitchen has white cabinetry, double ovens and a breakfast area with a bay window over the gardens.
There are five bedrooms and six bathrooms across 5,866 square feet. A guest room on the main level has a full bath beside it, and the primary suite upstairs includes a sitting nook and a large marble bath. The finished lower level adds a recreation area, a wet bar and another full bath, and a stone terrace opens to level lawns and gardens. The property last sold for $1.25 million in 2014.
Alexander H. Chingas of Coldwell Banker Realty was the listing agent, and Gregory Mason of William Pitt Sotheby’s Int’l 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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