A 1923 Connecticut Colonial on Round Hill Road in Greenwich sold for $12 million, the highest-priced home sale publicly reported in the Bridgeport, Connecticut metro area for the week ending August 9, 2026. The five leading closings reported across the metro that week combined for $34.79 million in Bridgeport-area real estate.
The week’s sales were recorded at addresses in Greenwich, Old Greenwich, Westport and New Canaan, and the metro’s two highest reported closings both stand on Round Hill Road in Greenwich. Build years run from 1923 to 2014, pairing three pre-war houses with two custom homes completed since 2013, and acreage figures throughout the group.
No. 1 — $12,000,000 · 122 Round Hill Rd, Greenwich, Connecticut
More than seven acres in mid-country Greenwich hold the Connecticut Colonial at 122 Round Hill Rd, which closed on August 6, 2026 for $12,000,000. Completed in 1923, the seven-bedroom, seven-bathroom house carries a reported 9,208 square feet on one of the town’s long-established addresses.
A long private drive rises from the road, and the land opens up gradually behind it: a pond of nearly one acre at the back of the property, a swimming pool, a tennis court, a two-bedroom guest cottage and a detached three-car garage. The house keeps its period detail, including eight fireplaces, a formal dining room and a slate-tile roof. Listing materials credit some six decades of ownership by a single family.
Leslie McElwreath of Sotheby’s International Realty was the listing agent. Natalia Wixom of Compass Connecticut, LLC represented the buyer. The $12,000,000 closing put McElwreath at the listing side of RealtyWire’s highest-priced reported home sale in the Bridgeport metro area for the week ending August 9, 2026, ranking No. 1 in the metro’s weekly Top 5.
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No. 2 — $6,900,000 · 530 Round Hill Rd, Greenwich, Connecticut
The original main residence of Field View Farm, a pre-war Georgian Colonial at 530 Round Hill Rd in Greenwich, changed hands for $6,900,000 in a closing recorded August 6, 2026. Built in 1937, the six-bedroom house carries a reported 6,216 square feet on 4.3 acres.
A long sweeping driveway leads to the brick and clapboard home, comprehensively renovated and fitted with a new generator. The grounds carry a pool, a private gym in its own standalone structure and a heated four-stall horse stable set up for conversion to a guest cottage. Terraces and French doors face open fields and a mature evergreen grove, and the property abuts 8.5 acres of protected land trust property.
Danielle Malloy of Serhant Connecticut LLC was the listing agent. Alexandra Friedman of Compass Connecticut, LLC represented the buyer. The transaction ranked No. 2 in RealtyWire’s Bridgeport Metro Area Top 5 home sales for the week ending August 9, 2026, the second Round Hill Road closing on this week’s list.
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No. 3 — $5,700,000 · 6 Twin Circle Drive, Westport, Connecticut
A post-tension concrete tennis court, the surface used at elite clubs and college facilities, is among the amenities at 6 Twin Circle Drive in Westport’s Long Lots neighborhood, which sold for $5,700,000 on August 7, 2026. The 2013 house on a quiet cul-de-sac has six bedrooms, seven bathrooms and a reported 8,717 square feet.
The backyard is built around a pool with a spa, lounging areas and a full outdoor kitchen alongside the court. Indoors, an open floor plan runs to a chef’s kitchen with high-end appliances and two dishwashers, a private meditation room and a primary suite with a spa-inspired bath and steam shower. An upstairs playroom is fitted with six built-in beds, and the walk-out lower level holds a media room, gym, office and guest suite.
Judy Michaelis of Coldwell Banker Realty was the listing agent. Meredith Kamo of Compass Connecticut, LLC represented the buyer. The house went under contract the same day the current listing went live, and the sale closed $700,000 above its final asking price of $5,000,000, putting Michaelis at the listing side of the No. 3 transaction in RealtyWire’s Bridgeport Metro Area Top 5 for the week. It previously changed hands for $2,800,000 in 2018.
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No. 4 — $5,390,000 · 7 Grimes Rd, Old Greenwich, Connecticut
A 1929 house at 7 Grimes Rd sits within one of Old Greenwich’s private waterfront associations, which carries a private beach along with boating and raft docks, and it changed hands for $5,390,000 in a closing recorded August 3, 2026. The five-bedroom, four-bathroom residence carries a reported 3,449 square feet.
A covered front porch opens to formal living and dining rooms, a family room and a partially vaulted eat-in kitchen by Putnam Design with Wolf and Sub-Zero appliances, which extends to a south-facing deck above the pool, terrace and a detached 240-square-foot structure framed as a potential cabana. The upper floor holds the primary suite, with two custom walk-in closets and a dressing room, plus three further bedrooms, one with a private balcony. The property previously changed hands for $1,387,500 in 2004.
The agents on this sale could not be verified for publication, and RealtyWire invites a correction from the professionals involved. The house went under contract 12 days after the current listing date and closed at its full asking price, ranking No. 4 in RealtyWire’s Bridgeport Metro Area Top 5 home sales for the week ending August 9, 2026.
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No. 5 — $4,795,000 · 24 Llewellyn Drive, New Canaan, Connecticut
A spring-fed pond anchors the 1.77 acres at 24 Llewellyn Drive in New Canaan, where a custom house completed in 2014 brought $4,795,000 in a closing recorded August 3, 2026. The four-bedroom, five-bathroom residence carries a reported 6,407 square feet.
Soaring ceilings and an open-concept plan run through the contemporary design, which holds four en suite bedrooms and a geothermal energy system with radiant heat floors throughout. Outside, the acreage carries a heated pool, an in-ground trampoline, terraces with a fireplace and built-in grills, a detached three-car garage and a pool house with its own kitchen, bath, stone fireplace and sleeping loft facing the pond. The property previously changed hands for $560,000 in 1997, before the current residence was completed in 2014.
Jaime Sneddon and Kendall Sneddon of William Pitt Sotheby’s Int’l were the listing agents. Jaime Sneddon of William Pitt Sotheby’s Int’l represented the buyer. The $4,795,000 transaction ranked No. 5 in RealtyWire’s Bridgeport Metro Area Top 5 home sales for the week ending August 9, 2026.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 9, 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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