A waterfront home on 1.49 acres in the Noroton section of Darien sold for $8.20 million, the highest-priced home sale publicly reported in the Bridgeport, Connecticut metro area for the week ending August 16, 2026.
The week’s five highest-priced reported sales combined for $32.88 million, running from that Darien closing down to a pair of $5.80 million transactions in Old Greenwich and New Canaan. The properties behind them are spread across Noroton, Oenoke Ridge, Old Greenwich and New Canaan.
New Canaan accounted for the second-, third- and fifth-ranked closings, with two of those addresses on Oenoke Ridge. The houses date from the late 1890s to 2018, and Houlihan Lawrence held the listings on both the top sale and the fourth-ranked Old Greenwich transaction.
No. 1 — $8,195,000 · 30 Shipway Road, Darien, Connecticut
The waterfront property at 30 Shipway Road in Darien sold for $8,195,000 on August 14, 2026, the highest reported home price in the metro area that week. Built in 1977 and set on 1.49 acres in Noroton, the five-bedroom house carries a reported 6,998 square feet on the harbor side of the neighborhood.
Listing materials identify Chad Nehring as the architect and Pear Tree Point Design as the firm behind the coastal interiors. Nearly every room takes in unobstructed views of the harbor and Long Island Sound. The primary suite sits beneath vaulted ceilings and opens onto its own balcony above the water.
The main living spaces flow outdoors to grounds that hold a deep-water dock, a pool and spa and a gas fire pit. A two-car garage is attached to the house, and a detached three-car garage carries a well-appointed apartment above it, set up for guests or extended family.
Janine Tienken of Houlihan Lawrence was the listing agent. Missy Dye of William Raveis Real Estate represented the buyer. The $8,195,000 closing put Tienken at the listing side of the highest-priced home sale reported anywhere in the Bridgeport metro area for the week; the house went under contract 11 days after the current listing date and closed at its full asking price. The property previously changed hands for $4,100,000 in 2007.
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No. 2 — $6,838,000 · 256 Country Club Road, New Canaan, Connecticut
A 1999 residence at 256 Country Club Road in New Canaan changed hands on August 14, 2026 for $6,838,000, the second-highest reported price in the metro area that week. It stands on nearly three acres bordering protected Land Trust property, minutes from the town center, and carries five bedrooms across a reported 9,473 square feet.
A front-to-back gallery runs off the entry foyer, anchored by mahogany doors that open onto a 33-foot covered porch and outdoor terrace. Millwork, oak floors and French doors carry through the principal rooms, and the kitchen, family room and informal dining area are arranged in an open layout oriented toward the grounds. The primary suite has 12-foot ceilings and dual walk-in closets; four more en suite bedrooms, a substantial bonus room and a third-floor guest suite occupy the upper levels, while the lower level holds a recreation room, a media room, a half bath and a gaming room that walks out to a private terrace.
Outside, stone walls and lawns frame a pool reached through a hornbeam archway. The guest and pool house is built to function independently of the main residence, with a sitting room, kitchen, full bath and bedroom opening through French doors to the pool terrace, and five-plus garage bays serve the property.
Christine D. Saxe and Nikki Glazer of Compass Connecticut, LLC were the listing agents. Jessica Savitsky of Brown Harris Stevens represented the buyer. Saxe and Glazer carried the listing on the transaction that ranked No. 2 in RealtyWire’s Bridgeport Metro Area Top 5 for the week. The property previously changed hands for $3,300,000 in 2020.
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No. 3 — $6,250,000 · 211 Oenoke Ridge, New Canaan, Connecticut
A modern farmhouse at 211 Oenoke Ridge in New Canaan was recorded at $6,250,000 on August 10, 2026, third-highest in the metro area for the week. Completed in 2018, it holds five bedrooms across a reported 6,588 square feet, near the New Canaan Nature Center and its walking trails and within a sidewalk stroll of the village’s restaurants, shops and theater.
A wraparound porch leads into a foyer, an expansive living room with a gas fireplace and a chef’s kitchen built around an oversized center island, a butler’s pantry and a custom bar area. The adjoining family room, anchored by a second fireplace, opens through French doors to the grounds. The primary suite has vaulted ceilings, a spa-inspired bath and expansive walk-in closets, with views over the pool, and four additional en-suite bedrooms sit alongside it.
The backyard carries a Gunite pool and spa, a stone terrace with several seating and lounging areas and a fully equipped outdoor kitchen, set against professional landscaping and a broad flat lawn. The lower level adds a large game room and a gym, and a separate barn on the property is outfitted with a private basketball court.
Melissa Rwambuya of William Raveis Real Estate was the listing agent. Lisa M. Ferrante of Houlihan Lawrence represented the buyer. Rwambuya’s listing produced the third-highest reported home sale in the Bridgeport metro area for the week, at $6,250,000. The property previously changed hands for $1,325,000 in 2018.
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No. 4 — $5,800,000 · 251 Palmer Hill Rd, Old Greenwich, Connecticut
A restored Victorian estate at 251 Palmer Hill Rd in Old Greenwich sold for $5,800,000 on August 15, 2026, the fourth-highest reported price in the metro area that week. The residence dates to the late 1890s and sits on 1.38 acres, with six bedrooms and a reported 6,797 square feet.
Oversized windows light rooms set under soaring ceilings, and window seats and an open flow between rooms carry the original architectural detail through a renovation for modern use. The new kitchen is paired with a butler’s pantry, a spacious laundry room and a mudroom with a shower.
A saltwater pool and a designed pool house give the grounds a private setting, and a gracious wraparound porch faces the lawns.
BK Bates of Houlihan Lawrence was the listing agent. Deborah Needle of Houlihan Lawrence represented the buyer. The $5,800,000 sale ranked No. 4 in RealtyWire’s weekly Bridgeport Metro Area Top 5, with Bates on the listing side; Houlihan Lawrence also held the listing on the week’s highest-priced reported sale. The property previously changed hands for $2,100,000 in 2004.
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No. 5 — $5,800,000 · 140 Stoneleigh Road, New Canaan, Connecticut
The fifth-ranked sale, at 140 Stoneleigh Road in New Canaan, closed August 12, 2026 at $5,800,000. The Colonial chateau-style residence was built in 1996 on two flat, landscaped acres and holds six en suite bedrooms across a reported 10,143 square feet.
Eight indoor fireplaces are spread through the house, which was laid out with multiple family rooms, a dedicated wine cellar and a custom-designed sports den. The main level flows to the exterior amenities, where a built-in pool and an outdoor fireplace anchor the grounds and four garage bays serve the property.
The house stands on a quiet street with no cut-through traffic, in a walking neighborhood with bike and walking routes from the door and an active association, the Hoyt Farm Association, whose members organize seasonal gatherings and neighborhood trick-or-treating.
Aileen Mastey of William Pitt Sotheby’s Int’l was the listing agent. Robbie A. Blosio of William Pitt Sotheby’s Int’l represented the buyer. The $5,800,000 closing rounded out RealtyWire’s Bridgeport Metro Area Top 5 for the week ending August 16, 2026, with Mastey holding the listing. The property previously changed hands for $2,920,000 in 2001.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 16, 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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