The highest-priced home sales reported in the Bridgeport, Connecticut, metro area for the week ending October 4, 2026, came to a combined $25.61 million. Three of the five were in Greenwich, one was in Old Greenwich and one was in the Coleytown area of Westport, all of them in Fairfield County.
The group ran from a waterfront condominium near Greenwich’s ferry landing to an English Manor home on more than an acre and a Contemporary home in Westport with six bedrooms and seven bathrooms. Coldwell Banker Realty listed two of the five, the No. 1 and No. 5 sales.
No. 1 — $5,947,500 · 633 Steamboat Rd Apt 5, Greenwich, Connecticut
The week’s top sale was a condominium at 633 Steamboat Road in Greenwich, which sold for $5,947,500. Although it is recorded as a condominium, the residence is a freestanding townhouse with clapboard siding, set on tidal waterfront with views over Smith Cove and out to Long Island Sound. It was built in 1989 and has since been renovated.
The home has three bedrooms, three full baths and a half bath in 2,676 square feet, plus a loft of about 143 square feet. A private elevator serves every floor, and each level has tall windows and a door out to its own deck. There is also a terrace, an eat-in kitchen, built-in bookcases and two gas fireplaces. Residents have a stretch of lawn at the water’s edge, and the listing says an association dock for kayaks and canoes is due to be finished in 2026. A two-car garage comes with the home. The property last sold for $4.05 million in 2024.
May Wan Evers of Coldwell Banker Realty was the listing agent, and Joseph Barbieri of Sotheby’s International Realty represented the buyer. Evers also appears at No. 2 on this week’s list, as the agent who represented the buyer of 25 Cove Road.
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No. 2 — $5,800,000 · 25 Cove Rd, Old Greenwich, Connecticut
In the Lucas Point association of Old Greenwich, 25 Cove Road sold for $5,800,000. The Shore Colonial was completed this year by Braydan Construction, and its owners have access to a neighborhood beach and a private pier.
Finished in shingle siding, the home has water views, four bedrooms, four full baths and a half bath across 3,827 square feet. Inside are hand-sewn oak beams, a kitchen built around an island, built-in bookcases and a fireplace. A heated pool sits in the private backyard, framed by landscaping, and the 0.28-acre lot has a stone wall. A two-car garage completes the property. The property last sold for $2.77 million in 2025, before the current house was built.
Alison Leigh of Brown Harris Stevens CT, LLC was the listing agent. May Wan Evers of Coldwell Banker Realty represented the buyer, one of two sales for Evers in this week’s Top 5; Evers was also the listing agent for the No. 1 sale.
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No. 3 — $4,950,000 · 16 Annjim Dr, Greenwich, Connecticut
The largest home on the list, at 6,997 square feet, is a 2015 Colonial at 16 Annjim Drive in the Cos Cob section of Greenwich. It sold for $4,950,000. The shingled home stands on level ground at the end of a quiet cul-de-sac, on 0.36 acres.
The kitchen, with a big center island and room to eat, opens to the family room, and French doors lead from there to a private terrace and the backyard. Each of the five bedrooms has its own bath, and one of them is a guest suite on the finished lower level. The home has five full baths and a half bath in all, three fireplaces, rooms for work, exercise and recreation, and a two-car garage. It is also equipped with a whole-house generator, HEPA air filtration and a water filtration system. The property last sold for $3.195 million in 2015.
Amanda Bates Goodro and BK Bates, both of Houlihan Lawrence, were the listing agents. Erin Brooks of Sotheby’s International Realty represented the buyer.
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No. 4 — $4,650,000 · 17 Brookside Park, Greenwich, Connecticut
The oldest home on this week’s list dates to 1907. The English Manor at 17 Brookside Park in Greenwich, built of stone and shingle and since renovated, sold for $4,650,000. It sits down a private lane on 1.06 level acres, with landscaped grounds and a rock garden.
Four fireplaces run through the home. The renovated eat-in kitchen connects to a dining room with its own fireplace, and French doors from both rooms open to a secluded stone terrace. On the same floor are a sunny living room with a fireplace, a family room built around a large stone fireplace with custom built-ins, a powder room and a second terrace. Upstairs, the primary suite has a sitting room with a fireplace, a walk-in closet and an updated marble bath, and four more bedrooms share the second floor with two full baths.
Above the detached two-car garage is an apartment with a bedroom, a full bath and a walk-in closet, which brings the home to six bedrooms. It has 4,775 square feet, with four full baths and a half bath in all. The property last sold for $2.75 million in 2020.
Alexandra Friedman of Compass Connecticut, LLC was the listing agent, and Jeff Jackson of Corcoran Centric Realty LLC represented the buyer.
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No. 5 — $4,265,000 · 21 Lockwood Circle, Westport, Connecticut
At 21 Lockwood Circle in Westport’s Coleytown neighborhood, a Contemporary home completed this year by Able Construction sold for $4,265,000. Clad in shingle and wood siding, it sits on 0.68 landscaped acres on a quiet street, with a gunite pool, a patio with an outdoor grill and beach access.
The entrance foyer has a wood-accented ceiling and a millwork feature wall, and walls of glass bring light into the rooms beyond. French doors lead from the great room, with its marble fireplace, out to the pool and patio. The kitchen has a large island, stone counters, custom cabinetry, Thermador appliances and a pantry, and the dining room has lighted shelving and looks out over the grounds. An office and a mudroom are also on the main level.
A glass-lined stair tower rises to the bedroom suites. Behind double doors, the primary suite has a balcony, two custom walk-in closets and a bath with a glass shower. That level also has a laundry room with two washers and two dryers, and stairs continue up to finished bonus space. The partially finished lower level includes a fifth bedroom suite, a recreation room, a gym, media space and storage. In all, the home has six bedrooms, six full baths and a half bath, 6,611 square feet and an attached three-car garage. The property last sold for $725,000 in 2024, before the current house was built.
Douglas Bross of Coldwell Banker Realty was on both sides of the sale, as listing agent and buyer’s agent. It was the second Coldwell Banker Realty listing in this week’s Top 5, alongside the No. 1 sale.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 4, 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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