The five highest-priced home sales reported in Greater Bridgeport & Lower Naugatuck Valley, Connecticut for the week ending October 25, 2026, totaled $4.831 million. Prices ran from $1,200,000 at the top to $825,000, a price two of the homes shared.
Beyond Trumbull, the list reached Monroe and the Lordship neighborhood of Stratford. The homes were built between 1968 and 1996 and range from 2,744 to 6,241 square feet, and among them are a home within walking distance of the water and another on more than an acre with a three-car garage.
No. 1 — $1,200,000 · 141 Putting Green Road, Trumbull, Connecticut
The week’s top sale was a Georgian-inspired Colonial on a cul-de-sac in Trumbull’s Hillandale neighborhood, which sold for $1,200,000. Built in 1989 on what were once the fairways of the former Hillandale Country Club, the home stands on 2.22 acres, the largest lot among the five. At 6,241 square feet, it is also the largest of the five homes.
The kitchen was recently renovated and has a center island, a peninsula with bar seating and room for prep work, a breakfast nook and direct access outside. Ceilings rise above nine feet, and custom moldings run through the main rooms. The great room on the main level is built around a stone fireplace that reaches from floor to ceiling, with built-in bookshelves and a wet bar, and French doors open from it into a sunroom.
Upstairs are the primary suite and four other bedrooms. The suite has a two-sided fireplace, a sitting area and an updated bath with a soaking tub. On the third level, a large bonus room could serve as an office, a studio or quarters for guests or an au pair. The finished lower level adds 1,260 square feet of recreation space, with a family room of its own, a kitchenette, a full bath and an area for exercise and games.
In all, the home has five bedrooms and five bathrooms, four full and one half, the most bathrooms among the five. It also has four fireplaces, a deck, a two-car attached garage and a whole-house generator. The property last sold in 2020 for $625,000.
Scott Palma of William Raveis Real Estate was the listing agent, and Denise Walsh, also of William Raveis Real Estate, represented the buyer.
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No. 2 — $1,015,000 · 4 Founders Way, Monroe, Connecticut
In Monroe, a 1996 Colonial at 4 Founders Way went under contract eight days after it was listed and sold for $1,015,000, which was $40,000 above its asking price of $975,000. It is the newest of the five homes.
The home stands on a level lot of 1.08 acres. Work this year brought a renovated kitchen with new cabinetry, quartz countertops and all new appliances, along with refinished hardwood floors. The kitchen opens to a family room with a fireplace, and upstairs the primary suite has a walk-in closet and its own bath. The finished lower level walks out to the yard and has two rooms that could serve as a gym, an office or a place for recreation.
Outside, a wraparound deck looks over the level backyard, and there is a three-car attached garage. The home has four bedrooms, three bathrooms (two full and one half) and 3,264 square feet, and it is minutes from Great Hollow Lake, Wolfe Park and the Town Green. The property last sold in 1999 for $460,000.
Marissa Grasso of Carey & Guarrera Real Estate was the listing agent, and James F. Wood of Coldwell Banker Realty represented the buyer.
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No. 3 — $966,000 · 52 Mallett Drive, Trumbull, Connecticut
On a corner lot along Mallett Drive, a level street in Trumbull’s Tashua neighborhood within the Tashua School District, a 1977 Colonial sold for $966,000. Paver walkways lead to a front with bay windows and vinyl siding, on a landscaped lot of one acre.
Hardwood floors, recently refinished, run throughout the interior. The updated kitchen has granite countertops, stainless steel appliances and light cabinetry, and just beyond it is a family room with a vaulted ceiling and a fireplace. A home office on the main level could double as a playroom, and there are separate living and dining spaces as well. Upstairs, the primary bedroom has its own bath and a walk-in closet. A large Trex deck overlooks the level, fully fenced backyard.
The home has four bedrooms, three bathrooms (two full and one half), 2,786 square feet and a two-car attached garage. The property last sold in 2024 for $855,000.
The home went under contract 24 days after it was listed and sold $116,000 above its asking price of $850,000. Matt Nuzie of RE/MAX Right Choice was the listing agent, and Laurie Cingari of Berkshire Hathaway NE Prop. represented the buyer. RE/MAX Right Choice listed two of the homes in this Top 5, this one and the sale on Porters Hill Road.
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No. 4 — $825,000 · 190 5th Avenue, Stratford, Connecticut
In Stratford’s Lordship neighborhood, a shingle-sided Colonial within walking distance of the water, with beach access, sold for $825,000. Built in 1968, it is the oldest of the five homes, and with seven bedrooms it has the most. It also has four bathrooms, three full and one half, in 4,514 square feet, on a lot of 6,969 square feet, the smallest among the five.
Bay windows bring light into both the living room, which has a fireplace, and the dining room. The kitchen has granite countertops and stainless steel appliances, and a sunroom beside it serves for casual meals, with sliding doors looking out to the deck, the gardens and an in-ground pool. A family room also has sliders to the deck and pool. The main level includes a laundry, a full bath, an office that could be used as a bedroom, and a bedroom with its own half bath.
Upstairs are four bedrooms and a hall bath with a second laundry hookup. The primary bedroom has distant water views, sitting areas, a walk-in closet and a full bath with a spa-style tub and a separate shower. Outside there are also a patio and a shed, and the full basement is partly finished. The property last sold in 1991 for $225,000.
The home sold $26,000 above its asking price of $799,000. Marilyn Heffers of Coldwell Banker Realty was the listing agent and also represented the buyer, the only sale in this Top 5 with the same agent on both sides.
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No. 5 — $825,000 · 157 Porters Hill Road, Trumbull, Connecticut
The fifth sale closed at $825,000 as well, matching the Lordship home’s price. It is a 1980 Colonial of stone and vinyl on Porters Hill Road in Trumbull’s Hillandale neighborhood, set on 0.81 acres with an underground sprinkler system and a two-car attached garage.
White cabinetry, quartz countertops, shiplap accents and stainless steel appliances fill the updated kitchen, which has a center island. The family room is anchored by a stone fireplace that runs floor to ceiling, and a den and a formal dining area share the first floor. A large enclosed porch looks out over the grounds. On the second floor, the primary bedroom has an updated bath with a walk-in shower and a double vanity, and two more bedrooms share another updated full bath.
The finished lower level has a recreation room with a wet bar and a beverage refrigerator. Outside, a playhouse comes with a bunk bed and a television. The home has three bedrooms and four bathrooms, three full and one half, in 2,744 square feet. The property last sold in 2010 for $470,000.
The home went under contract 18 days after it was listed and sold $26,000 above its asking price of $799,000. Scott Wright of RE/MAX Right Choice was the listing agent, giving the brokerage its second listing in this Top 5, and Christopher Giolitto of William Raveis Real Estate represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, October 25, 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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