Fairholme Estate, an 1891 manor house in the Belle Haven section of Greenwich, sold with a coachman’s cottage and a separate 5,800-square-foot guest house standing on its 2.74 acres, its interior the work of the designer Alexa Hampton.
That $21.25 million closing led five reported home sales in the Bridgeport, Connecticut metro area for the week ending September 20, 2026, which combined for $53.43 million. Greenwich accounted for all of them but one, a waterfront house on the Five Mile River in Norwalk’s Rowayton section, and Houlihan Lawrence was the listing brokerage on the four highest-priced closings. The oldest house on the list dates to 1891 and the newest was completed this year.
No. 1 — $21,250,000 · 44 & 40 Mayo Ave, Greenwich, Connecticut
Fairholme Estate, at 44 & 40 Mayo Ave, closed on September 15, 2026 at $21.25 million, the highest-priced reported home sale in the metro area for the week. The English Manor holds seven bedrooms and eight bathrooms across a reported 18,217 square feet and sits on 2.74 landscaped acres.
The house has been preserved in its historic character and updated for modern use, with the interior design credited to Alexa Hampton. A wraparound porch fronts the residence, and formal gardens, expansive lawns and a pool fill the grounds.
A coachman’s cottage also stands on the property, and the separate guest house adds 5,800 square feet.
The $21.25 million closing put Joanne Mancuso on the listing side of the highest-priced reported sale in RealtyWire’s Bridgeport metro area Top 5 for the week, and she has listed two earlier RealtyWire Top 5 sales in the metro. Joanne Mancuso of Houlihan Lawrence was the listing agent. Christopher Finlay of Brown Harris Stevens CT, LLC represented the buyer.
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No. 2 — $15,000,000 · 4 Rockwood Lane Spur, Greenwich, Connecticut
A newly built Transitional house at 4 Rockwood Lane Spur sold for $15 million, with the closing recorded September 18, 2026. The residence carries a reported 10,523 square feet over four customized levels, with six bedrooms and 11 bathrooms on 1.64 private acres.
Listing materials identify Christopher Pagliaro Architects as the architect, with East Coast Structures and M&N Development on the build. Behind a brick and cast stone facade, the house is fitted with oversized European Klar windows and white oak floors, and the kitchen rises to double height with a scullery alongside it. Each of the six bedrooms is en suite, and the primary adds a deck and a sitting room.
The walkout lower level holds a game room, a bar, a golf simulator and a gym with a sauna and a steam shower. Outdoors there is a pool and spa, a covered porch, an outdoor shower and a grill.
The house closed at its full asking price, putting Deborah Needle on the listing side of the second-highest reported sale in RealtyWire’s Bridgeport metro area Top 5 for the week. The property previously changed hands for $2,910,000 in 2023, before the current residence was completed in 2026. Deborah Needle of Houlihan Lawrence was the listing agent. Carol Zuckert of Sotheby’s International Realty represented the buyer.
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No. 3 — $6,650,000 · 47 Husted Ln, Greenwich, Connecticut
A single-level Regency-style house at 47 Husted Ln changed hands September 15, 2026 for $6.65 million. Built in 1960, it has four bedrooms and a reported 5,379 square feet.
Large living and entertaining rooms run into one another on the single floor, alongside a dining room and a fitted kitchen, and a separate wing holds the primary suite and the secondary bedrooms. The grounds are landscaped, the house sits close to the town center, schools and transportation, and it was offered with the option to buy it furnished.
The property went under contract 28 days after the current listing date and previously changed hands for $3,500,000 in 2015. The $6.65 million closing ranked No. 3 in RealtyWire’s Bridgeport metro area Top 5 for the week. Sally Maloney of Houlihan Lawrence was the listing agent.
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No. 4 — $5,350,000 · 43 Rowayton Avenue, Norwalk, Connecticut
A 1920 waterfront house at 43 Rowayton Avenue sold for $5.35 million, the closing recorded September 15, 2026. It has four bedrooms and a reported 2,387 square feet on the Five Mile River, in the Rowayton section of Norwalk.
The property comes with a private beach and a dock, and the house takes in Long Island Sound from a terrace with a gas fireplace and two decks. An open floor plan puts water views in nearly every room, and the primary suite is on the first floor. The house stands within the Rowayton Beach Association, a short walk from downtown Rowayton.
The property previously changed hands for $2,515,000 in 2005, and the September 15 closing placed Douglas Milne on the listing side of the No. 4 sale in RealtyWire’s Bridgeport metro area Top 5 for the week. Douglas Milne of Houlihan Lawrence was the listing agent. Keiley Fuller of Compass Connecticut, LLC represented the buyer.
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No. 5 — $5,175,000 · 583 Lake Ave, Greenwich, Connecticut
A washed brick colonial at 583 Lake Ave sold on September 18, 2026 for $5,175,000. Built in 1942, the house has five bedrooms and seven bathrooms across a reported 8,082 square feet, set back behind stone pillars and a circular drive on three acres of lawn.
Listing materials identify the location as the Golden Triangle, abutting Rockwood Lane, and specimen trees and plantings stand across the lawn. French doors open from the large formal rooms onto a flagstone terrace.
A wood-paneled library and a den each have a fireplace. A family room and a bonus recreation room over the garage are lined with windows, and the kitchen carries exposed rustic beams, a soaring ceiling, stainless steel appliances, white cabinets and granite counters, with an adjoining breakfast area and a fireplace. Upstairs, the primary suite has a tray ceiling, walk-in closets and a view over the rear garden, and four more en-suite bedrooms complete the floor, one of them reached by a back staircase. The lower level is finished and opens to the backyard.
The house went under contract 14 days after the current listing date, and the $5,175,000 closing put Cate Keeney on the listing side of the No. 5 sale in RealtyWire’s Bridgeport metro area Top 5 for the week. Cate Keeney of Sotheby’s International Realty was the listing agent. Deborah Needle of Houlihan Lawrence represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, September 20, 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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