The five highest-priced home sales publicly reported in the Bridgeport, Connecticut metro area for the week ending August 9, 2026 combined for $34.79 million. The week was led by the $12,000,000 sale of a 1923 Colonial estate at 122 Round Hill Road in Greenwich, one of two closings on that road to make this week’s ranking.
The list is entirely a Fairfield County affair, with closings in Greenwich, Old Greenwich, Westport and New Canaan.
RealtyWireβs Top 5 ranks the five highest-priced residential closings it identified in the Bridgeport, Connecticut metro area for the reporting week. It may omit private, delayed, nondisclosed, or otherwise unreported transactions.
No. 1 — $12,000,000 · 122 Round Hill Rd, Greenwich, Connecticut
The week’s largest sale closed on August 6, 2026, when the estate at 122 Round Hill Road in Greenwich sold for $12,000,000. Built in 1923, the Connecticut Colonial offers a reported 9,208 square feet with seven bedrooms and seven baths, set on more than seven acres in the town’s mid-country section. The listing notes eight fireplaces, a formal dining room and a slate-tile roof, and says the property had been under one family’s ownership for roughly six decades.
A long private drive climbs from the road, and the grounds open up behind the house to a pond of nearly one acre. The parcel also holds a swimming pool, a tennis court, a two-bedroom guest cottage and a detached three-car garage, a combination the listing characterizes as increasingly hard to find on a single mid-country Greenwich parcel. Round Hill Road, which the listing counts among the town’s most established addresses, also produced the week’s second-ranked sale.
Leslie McElwreath of Sotheby’s International Realty was the listing agent. Natalia Wixom of Compass Connecticut, LLC represented the buyer.
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No. 2 — $6,900,000 · 530 Round Hill Rd, Greenwich, Connecticut
The week’s second-largest sale also closed on Round Hill Road in Greenwich, where a 1937 Georgian Colonial at No. 530 sold for $6,900,000 on August 6, 2026. The brick-and-clapboard house, described in the listing as the original main residence of the historic Field View Farm estate, offers a reported 6,216 square feet with six bedrooms on 4.3 acres, and the listing describes a comprehensive renovation that added a new generator.
A long driveway approaches the house, and the grounds include a pool, a private gym housed in its own standalone building, and a heated four-stall horse stable the listing suggests could be converted to a guest cottage or additional quarters. Terraces and multiple French doors face open fields and a mature evergreen grove, and the property abuts 8.5 acres of protected land-trust acreage.
Danielle Malloy of Serhant Connecticut LLC was the listing agent. Alexandra Friedman of Compass Connecticut, LLC represented the buyer.
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No. 3 — $5,700,000 · 6 Twin Circle Drive, Westport, Connecticut
In Westport’s Long Lots neighborhood, 6 Twin Circle Drive sold for $5,700,000 on August 7, 2026. The 2013-built house sits on a cul-de-sac with a reported 8,717 square feet, six bedrooms and seven baths, and the listing stresses the location’s convenience to Bedford Middle School, Staples High School, downtown Westport, the train, Longshore and Compo Beach.
The backyard is set up for recreation, with a pool and spa, a full outdoor kitchen and a post-tension concrete tennis court. Inside, the kitchen carries high-end appliances and two dishwashers, the main level includes a meditation room, and the primary suite features a steam shower and a dressing room. Upstairs, a playroom is fitted with six built-in beds, while 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.
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No. 4 — $5,390,000 · 7 Grimes Rd, Old Greenwich, Connecticut
In Old Greenwich, 7 Grimes Road closed for $5,390,000 on August 3, 2026. The 1929 house has five bedrooms, four baths and a reported 3,449 square feet, while the listing describes more than 5,000 square feet. The property sits on a cul-de-sac within one of Old Greenwich’s private waterfront associations, which the listing says offers a private beach along with boating and raft docks.
A covered front porch opens to formal living and dining rooms, a family room and an eat-in kitchen with Wolf and Sub-Zero appliances, extending to a south-facing deck above the pool, the terrace and a detached structure the listing casts as a potential cabana. A main-level office carries a full bath, and the upper level, with views of the Sound per the listing, holds the primary suite and three additional bedrooms, one with a private balcony. Systems include a generator, radiant heat and central air.
Professional representation for this transaction was not reported at publication time.
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No. 5 — $4,795,000 · 24 Llewellyn Drive, New Canaan, Connecticut
In New Canaan, 24 Llewellyn Drive sold for $4,795,000 on August 3, 2026. The custom contemporary, built in 2014 on 1.77 acres, carries a reported 6,407 square feet, a total the listing breaks down as roughly 5,640 square feet in the main house plus a 777-square-foot pool house, along with four en-suite bedrooms and five baths. The listing describes high ceilings, an open floor plan, and a geothermal system with radiant-heat floors throughout.
Outside, the grounds hold a heated pool, an in-ground trampoline, and terraces with a fireplace and built-in barbecue stations, while the pool house adds a kitchen, bath, stone fireplace and sleeping loft, all overlooking a spring-fed pond. A detached three-car garage completes the property.
Jaime Sneddon and Kendall Sneddon of William Pitt Sotheby’s International were the listing agents. Jaime Sneddon of William Pitt Sotheby’s International represented the buyer.
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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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See full market data on our Bridgeport, Connecticut market page.
