The 2005-built house at 170 Old Mill Road went under contract 9 days after the current listing date and closed $5,000 above its final asking price of $8,495,000, leading five reported home sales across the Bridgeport, Connecticut metro area that combined for $30.83 million for the week ending September 6, 2026.
The top of the metro’s real estate market spanned Greenwich, Old Greenwich, Darien and New Canaan for the week, with sale prices running from $4.7 million to $8.5 million, and Houlihan Lawrence represented the listing side of three of this week’s five highest-priced reported sales.
No. 1 — $8,500,000 · 170 Old Mill Rd, Greenwich, Connecticut
Four gated acres with a pool, a spa, terraces and open lawn surround the seven-bedroom house at 170 Old Mill Road in Greenwich, which sold for $8.5 million. The transaction closed August 31, 2026, and ranked No. 1 in RealtyWire’s weekly Bridgeport Metro Area Top 5.
Inside a reported 13,974 square feet, the 2005-built home centers on a double-height family room, a bar area and an updated kitchen with two oversized islands. The primary suite pairs dual walk-in closets with a spa-style bath, and every additional bedroom is en suite. A first-floor guest suite, a mudroom, a collector’s garage, a finished lower level with a family room and gym, and third-floor storage complete the floor plan.
The property previously changed hands for $4,270,000 in 2020, and the $8.5 million closing marks Joanne Mancuso’s second appearance in a RealtyWire Top 5 roundup for the metro.
Joanne Mancuso of Houlihan Lawrence listed the property, which went under contract 9 days after the current listing date and closed $5,000 above its final asking price of $8,495,000.
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No. 2 — $7,950,000 · 189 Shore Rd, Old Greenwich, Connecticut
A waterfront residence at 189 Shore Road in Old Greenwich took the No. 2 spot at $7.95 million, with the closing recorded September 1, 2026. Built in 1979 and later redesigned by architect Rick Swann, the four-bedroom home holds water views from nearly every room, with high ceilings and an open floor plan oriented toward Long Island Sound.
Walls of glass and French doors anchor the first-floor rooms and open to a wrap-around deck along the water. The kitchen is finished with marble countertops and a generous island, a first-floor den can serve as a fifth bedroom, guest suite or office, and the parcel includes private dock access to the Sound. The house carries a reported 4,262 square feet.
The home previously changed hands for $5,750,000 in 2018. The $7.95 million closing put Joy Metalios of Houlihan Lawrence on the listing side of the second-highest-priced reported home sale in the metro for the week.
Joy Metalios of Houlihan Lawrence was the listing agent. Daphne Lamsvelt-Pol of Sotheby’s International Realty represented the buyer.
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No. 3 — $4,950,000 · 456 Round Hill Rd, Greenwich, Connecticut
History anchors the week’s No. 3 sale. The center hall Colonial at 456 Round Hill Road in Greenwich sits within the Round Hill Historic District, and listing materials date the property to 1795, when it served as the community’s first schoolhouse, before its transformation into the mid-19th-century residence that stands today.
The five-bedroom main house stands high on 4.6 fully fenced acres with broad western exposure and sunset views, and it blends period details, wide plank floors among them, with modern updates. Sweeping lawns, mature landscaping, vegetable and flower gardens and a swimming pool fill out the grounds, along with a separate garage cottage.
The sale closed on September 1, 2026, at $4.95 million, $355,000 above its final asking price of $4,595,000, and the property went under contract 8 days after the current listing date. It previously changed hands for $2,025,000 in 1998.
Krissy Blake of Sotheby’s International Realty was the listing agent. Leslie McElwreath of Sotheby’s International Realty represented the buyer.
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No. 4 — $4,725,000 · 13 Sunswyck Road, Darien, Connecticut
In Darien, a custom-built five-bedroom house at 13 Sunswyck Road sold for $4,725,000, with the transaction closing September 1, 2026. Completed in 2020, the home stands within the Delafield Island Association, near the beach, town, train and schools.
A two-story foyer opens to the dining room and parlor, and an eat-in kitchen with two expansive islands and custom cabinetry flows into the family room and out to a covered terrace with built-in heaters for year-round use. Two home offices, a breakfast nook, two powder rooms and a large mudroom complete the first floor. Upstairs, the primary suite carries a vaulted ceiling, a large walk-in closet, an adjoining sitting room and a bath with radiant heated floors, a soaking tub and an oversized shower, joined by four additional bedrooms and three full baths. The house holds a reported 6,151 square feet, plus a finished basement with high ceilings and a framed-and-plumbed third floor left ready for future build-out.
The property went under contract 17 days after the current listing date, and it previously changed hands for $950,000 in 2019, before the current residence was completed in 2020.
Cheryl Williams of Brown Harris Stevens represented the listing side of the transaction, which ranked No. 4 in RealtyWire’s weekly Bridgeport Metro Area Top 5.
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No. 5 — $4,700,000 · 146 Lambert Road, New Canaan, Connecticut
The week’s fifth-ranked transaction, a five-bedroom house at 146 Lambert Road in New Canaan, sold for $4.7 million on September 1, 2026. The 2000-built home went under contract 6 days after the current listing date and closed $5,000 above its final asking price of $4,695,000.
French doors open from the formal living and dining rooms to a landscaped courtyard, where a fountain and a pool extend the rooms outdoors. The eat-in kitchen holds two islands and dual ovens, the family room rises to a cathedral ceiling above a fieldstone fireplace, and radiant heated stone floors add warmth through the reported 7,443 square feet. The first-floor primary suite includes a newly renovated bath, custom closets and an adjoining private office or den, while four en suite bedrooms, a guest room and a bonus room fill the second floor. Professionally landscaped grounds with specimen trees frame the setting.
The property previously changed hands for $3,850,000 in 2005. The closing rounded out RealtyWire’s Bridgeport Metro Area Top 5 for the week, with Taylor Tait of Houlihan Lawrence on the listing side.
Taylor Tait of Houlihan Lawrence was the listing agent. Bettina Hegel of Brown Harris Stevens represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, September 6, 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 Bridgeport, Connecticut market page.
