These are the five highest-priced home sales reported in Greater Bridgeport & Lower Naugatuck Valley, Connecticut for the week ending November 8, 2026, and together they came to $3.59 million. All five are single-family homes in Fairfield County, with prices running from $637,000 to $825,000. In two of the sales, the same agent was the listing agent and also represented the buyer.
No. 1 — $824,995 · 18 Woods Way Drive, Shelton, Connecticut
The top sale of the week is a home that has not been built yet. It sold for $825,000 at 18 Woods Way Drive, in the new Woods Way subdivision in Shelton, and it is the only new construction in this Top 5.
The home is the Birch model, a design that draws on both Colonial and ranch styles and places the primary bedroom suite on the first floor, so daily life can stay on one level. The plans call for three bedrooms, two full baths and a half bath, and 2,308 square feet. On the main floor, the kitchen and dining room share one open space that leads into a large family room with vaulted ceilings, and the same floor has an office and its own laundry room. The second floor has two more bedrooms, each with a walk-in closet, and another full bath.
Below, a full unfinished basement leaves room to add living space later. The plans also include an attached two-car garage, a porch and a deck, on a lot of 4,791 square feet, the smallest among the five.
Marissa Grasso of Carey & Guarrera Real Estate was the listing agent with Chris Carey, also of Carey & Guarrera Real Estate. Grasso also represented the buyer, so the same agent was on both sides of the sale that ranks first this week.
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No. 2 — $799,900 · 4 Scenic Hill Lane, Monroe, Connecticut
The main room at 4 Scenic Hill Lane in Monroe rises two stories, with walls of windows, a custom wet bar and a stone fireplace that runs from floor to ceiling, one of two fireplaces in the home. The 1980 Colonial, finished in stone and wood siding with contemporary lines, sits on a landscaped corner lot of 1.07 acres in the Monroe Center neighborhood. That is the largest lot in this group, and at 4,117 square feet the home also has the most living space of the five.
The eat-in kitchen opens directly to the garage, and the laundry is on the first floor. The home has four bedrooms and four full baths, and every level has a full bath. Upstairs is a bonus room. The primary suite has an updated bath with a freestanding soaking tub, a separate shower, dual vanities and heated floors.
The finished lower level walks out to the yard and has a recreation room, an exercise area and a full bath, along with a large unfinished section for storage or a workshop. Outside, several decks look out over a backyard framed by tall trees, stone walls and specimen plantings. The property last sold in 2004 for $526,000.
The home sold for $799,900, its full asking price. Michael Wright of RE/MAX Right Choice was the listing agent and also represented the buyer, so the same agent was on both sides of the sale.
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No. 3 — $675,000 · 77 Lawlor Terrace, Stratford, Connecticut
The oldest home among the five dates to 1940, but 77 Lawlor Terrace in Stratford’s North End was extensively renovated in 2024. That work brought a new kitchen with stainless steel appliances, renovated bathrooms and hardwood floors throughout. The Colonial was also expanded with an attached garage and a primary suite that has its own full bath.
The home has four bedrooms, two full baths and a half bath in 2,539 square feet, on 0.39 acres. A gas fireplace warms the main living area, and a separate room is given over to a bar for entertaining. The private backyard has a patio and a fire pit, and the property comes with beach access. I-95, Route 8, the Merritt Parkway and the Metro-North Railroad are all minutes away, as is the Stratford shoreline. The property last sold in 2024 for $531,000.
The home went under contract 19 days after it was listed and sold for $675,000, which was $50,000 above its $625,000 asking price. Ralph Lewis of Coldwell Banker Realty was the listing agent, and Carrie Levitt Kaplan of Berkshire Hathaway NE Prop. represented the buyer.
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No. 4 — $650,000 · 28 Brook Road, Trumbull, Connecticut
The same owners had 28 Brook Road for 43 years. The cedar-sided 1956 Colonial in Trumbull’s Long Hill section sold for $650,000. It sits on a corner lot of 0.67 acres on a small dead-end street, within the Jane Ryan School District, and Brook Road is less than 1.5 miles from the Merritt Parkway.
Inside are four bedrooms, three full baths and an office on the main level, in 2,205 square feet. Outdoors, a bluestone patio opens onto a spacious yard with a hand-built wooden shed that suits storage or a workshop, and rows of green arborvitae along the sides of the home give it some privacy.
Ryan Miller of William Pitt Sotheby’s Int’l was the listing agent. The home went under contract within 18 days of being listed and sold for $10,000 more than its $640,000 asking price. Alaina E. Capasso of Advise Realty Services represented the buyer.
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No. 5 — $637,000 · 56 Sunrise Avenue, Trumbull, Connecticut
Out back, 56 Sunrise Avenue has an in-ground pool and a large patio, in a yard edged by mature landscaping and trees. The 1960 ranch, also in Trumbull’s Long Hill section, sold for $637,000. It sits on a level half-acre lot on a quiet cul-de-sac.
With 1,488 square feet, three bedrooms and one bath, it is the smallest home of the five, and it is laid out on one level with an open plan. The kitchen has white cabinets, stainless steel appliances and a large center island, and it flows into the living and dining spaces. The home has hardwood floors, recessed lighting and a stone fireplace. A bright room with a vaulted ceiling and a skylight leads out to the backyard and pool. There is also a partially finished basement and an attached two-car garage. The property last sold in 2015 for $339,000.
Brian J. McCarthy of LMS Strategies, Inc. was the listing agent, and the home went under contract 16 days after it was listed. Dawn Damiani of BHGRE Gaetano Marra Homes represented the buyer.
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