Set along the water minutes from Shorehaven Golf Club, the house at 10 Shorehaven Road in Norwalk carries a private dock, a pool and a spa on landscaped grounds, and it previously changed hands for $6,200,000 in 2004. Its September 21, 2026 closing led five reported home sales that combined for $32.04 million across the Bridgeport, Connecticut metro area for the week ending September 27, 2026.
Beyond Norwalk, the week’s real estate record reaches into New Canaan, Darien and Riverside, with Darien represented more than once and one of its houses inside the Tokeneke Association. The five homes were built between 1951 and 2006.
No. 1 — $10,000,000 · 10 Shorehaven Road, Norwalk, Connecticut
A Nantucket-inspired estate on the Shorehaven waterfront in Norwalk sold for $10 million, the highest reported price of the week in the Bridgeport metro area. The sale closed on September 21, 2026. Built in 2000, the house holds five bedrooms across a reported 9,564 square feet.
A curved staircase rises from the entry hall, and the plan opens into formal living and dining rooms, a chef’s kitchen and an adjoining family room finished with a coffered ceiling, a fireplace and French doors. All five bedrooms are ensuite. The second-floor primary suite has two spa-style baths and a balcony with water views, and a custom office with its own balcony and a richly paneled study complete the interiors. Tall windows carry daylight through the rooms.
The landscaped grounds run to the waterfront, where a pool, a spa and a private dock sit close to the tide line, and a veranda spans the length of the house. The property sits in the coastal enclave of Shorehaven, minutes from Shorehaven Golf Club and local amenities. It previously changed hands for $6,200,000 in 2004.
Laurie Morris of Compass Connecticut, LLC was the listing agent. The $10 million closing placed Morris on the listing side of the highest-priced reported sale in RealtyWire’s Bridgeport Metro Area Top 5 for the week. Wendy Ryan of Brown Harris Stevens represented the buyer.
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No. 2 — $6,550,000 · 119 Proprietors Xing, New Canaan, Connecticut
The listing agents were Molly Rubins and Shawn Elliott of Nest Seekers International, and the transaction ranked No. 2 in RealtyWire’s Bridgeport Metro Area Top 5 for the week. Suzanne Dodge of William Raveis Real Estate represented the buyer.
A six-bedroom estate on four private acres at 119 Proprietors Crossing in New Canaan reached $6.55 million in a September 22, 2026 closing, the second-highest reported price in the metro area that week. The house carries a reported 12,510 square feet.
Listing materials identify James E. Gearity as the architect. A private drive and a fountain lead to a soaring foyer hung with a Baccarat chandelier, and seven fireplaces are spread through the house. The chef’s kitchen opens to a great room under a 35.5-foot vaulted ceiling, built around a large quartz island with integrated audio, and a formal dining room sits beneath a second Baccarat chandelier. The west wing holds the primary suite and a study, where a hidden staircase descends to a gym and an 800-square-foot dressing room. An adjacent junior primary suite has its own entrance and sitting room, and four more bedrooms are upstairs.
The finished lower level holds a media room, a fitness center and a wine cellar. Outdoors, the grounds include a dining pavilion, an outdoor kitchen and a newly constructed pool and spa, with room set aside for a tennis or pickleball court. The estate was built with commercial-grade systems, radiant heat and a Welsh slate roof, and it includes a four-car garage and an elevator. The property previously changed hands for $3,915,000 in 2024.
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No. 3 — $6,100,000 · 38 Three Wells Lane, Darien, Connecticut
A Colonial on two private acres in northern Darien closed on September 21, 2026 for $6.1 million. The 1989 house at 38 Three Wells Lane carries five bedrooms and a reported 7,306 square feet.
A living room with a fireplace anchors the formal side of the plan, and the dining room is served by an adjoining butler’s pantry. A study and library, with a fireplace of its own, sits apart from the main entertaining rooms. At the center of the house, the kitchen and family room open directly onto the outdoor entertaining spaces at the rear.
Those grounds hold a pool and a renovated pool house, an outdoor kitchen, a BBQ pit, a pergola and a fire pit. The remodeled lower level was fitted with a custom theater room, a walk-in wine cellar and a sauna. Recent work also covered the pool hardscape, an upgraded HVAC system, a whole-house water filtration system, a newly paved driveway with added front parking, Lutron smart lighting indoors and out, and an Eero whole-home Wi-Fi system. The property previously changed hands for $3,200,000 in 2018.
Laura Hoglund of Berkshire Hathaway NE Prop. listed the property, and the sale closed $905,000 above its final asking price of $5,195,000. The property went under contract 2 days after the current listing date. The transaction ranked No. 3 in RealtyWire’s Bridgeport Metro Area Top 5 for the week. Katharine Gray Bunoski of Compass Connecticut, LLC represented the buyer.
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No. 4 — $4,790,000 · 14 Bradbury Pl, Riverside, Connecticut
A custom Colonial at the end of a quiet cul-de-sac at 14 Bradbury Place in Riverside changed hands for $4.79 million, with a closing date of September 21, 2026. The 2006 house holds five bedrooms across a reported 7,000 square feet.
A two-story center hall foyer opens the plan, flanked by formal living and dining rooms. The open chef’s kitchen runs into a family room with a fireplace and direct access to a stone terrace, and the main level also carries a private home office, a powder room and a laundry room. Upstairs, the primary suite has a fireplace, a custom walk-in closet and a spa-inspired bath, with four additional en-suite bedrooms alongside it.
A walk-out lower level of approximately 2,000 square feet, counted within the home’s total square footage, holds a recreation and playroom with a fireplace, a fitness room, an optional guest bedroom, a full bath and French doors to a fenced, landscaped yard. A walk-up unfinished attic, a yard shed and an oversized garage with electric vehicle charging capability round out the property, which sits near schools, the train and shopping. It previously changed hands for $3,050,000 in 2021.
Sabrina Lanosa of William Pitt Sotheby’s Int’l was the listing agent. The property closed at its full asking price. Lanosa’s listing closed at its full asking price and ranked No. 4 in RealtyWire’s Bridgeport Metro Area Top 5 for the week. Joy Metalios of Houlihan Lawrence represented the buyer.
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No. 5 — $4,600,000 · 6 Searles Road, Darien, Connecticut
Inside Darien’s Tokeneke Association, a classic coastal Connecticut colonial at 6 Searles Road traded at $4.6 million, with a closing date of September 23, 2026. Built in 1951, the five-bedroom house carries a reported 4,740 square feet, a figure that excludes the partially finished basement and the wine cellar.
One of the bedrooms is a first-floor guest suite, with four more on the second level. The main floor runs from a formal living room and dining room to a casual dining area and an office, and the chef’s kitchen opens to a fireplace-lit gathering room. A large mudroom with garage and back-entrance access sits off the main rooms, alongside a separate laundry room. The primary suite has an en-suite bath and two walk-in closets, and the second floor also holds a second en-suite bedroom, two bedrooms sharing a renovated hall bath, and a sitting and work area.
The finished basement holds a wine room with capacity for 1,600 bottles alongside a casual sitting area, and a stone patio looks out over a green yard. The attached garage takes two cars and more, with a third bay in a barn that is still an open shell. Listing materials put the Tokeneke tax at $1,553, covering private security and road maintenance, with a separate social fee of $100 a year. The property previously changed hands for $3,000,000 in 2005.
Susan Massey of Brown Harris Stevens was the listing agent. The $4.6 million closing placed Massey at the listing side of the No. 5 sale in RealtyWire’s Bridgeport Metro Area Top 5 for the week. Kelly Connell 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, September 27, 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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