These are the five highest-priced home sales reported in the Greater New Haven Area, Connecticut for the week ending November 8, 2026, and together they total $6.315 million. Milford accounts for four of them, and the fifth is in East Haven.
The group includes four single-family homes and one condominium, built between 1982 and 2003. Most of them sit close to the water, from a coastal contemporary in Woodmont to a small beach community off Merwin Avenue, and in one sale the same agent was on both sides.
No. 1 — $2,125,000 · 109 Hillside Avenue, Milford, Connecticut
In Woodmont, the top sale of the week is a cedar-clad contemporary on the water, designed by architect Ray Oliver and completed in 2000. From the main living area, a wall of windows looks out over Long Island Sound, and French doors open onto a large waterfront deck.
Inside, the ceilings are high and a stained-glass window adds color and character. The home has five bedrooms, the most of the five, along with four bathrooms (three full and one half) and 2,932 square feet. There are marble baths, an updated kitchen and a walk-in pantry. Upstairs, the primary suite has a Jacuzzi tub and its own water views, and the second floor also includes a reading nook, two more bedrooms and a laundry. Two further bedrooms, each with a walk-in closet, are on the third floor.
Perennial gardens and a fountain greet visitors on arrival, and a kayak can be launched from the property. The 4,791-square-foot lot is on a quiet one-way street with sidewalks, with a playground nearby and restaurants within walking distance. There is an attached two-car garage. The property last sold in 2007 for $1.4 million.
The home went under contract 14 days after it was listed and sold for $150,000 above its $1.975 million asking price. Carrie Sakey of Coldwell Banker Realty was the listing agent, and Karen Brewer of William Pitt Sotheby’s Int’l represented the buyer. Coldwell Banker Realty also listed the No. 4 sale in this Top 5.
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No. 2 — $1,335,000 · 152 West River Street, Milford, Connecticut
Downtown Milford’s shops, restaurants and harbor are within walking distance of this 1982 Colonial, and so is the Metro-North train station. The property is on the waterfront, with river frontage and a pond, and its 0.47-acre lot is wooded and landscaped. From the front porch, the sound of a cascading waterfall carries, along with church bells in the distance.
At 4,700 square feet, it is both the largest and the oldest home in the group, and its five bathrooms (four full and one half) are the most among the five sales. The home has four bedrooms, three fireplaces and hardwood floors, and many of its rooms have water views. It has been freshly painted throughout. A large backyard offers room for gardening and entertaining, and there is an attached two-car garage and a full unfinished basement. The property last sold in 2001 for $610,000.
Frank J. D’Ostilio of Houlihan Lawrence WD was the listing agent, and Anissa L. Paolillo of Redfin Corporation represented the buyer in the second-highest sale of the week.
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No. 3 — $1,050,000 · 104 Franklin Road, Milford, Connecticut
D’Amato Builders custom-built this Colonial in 2003, which makes it the newest of the five homes, and it stands at the end of a quiet cul-de-sac on a 0.51-acre lot. Inside, soaring ceilings and elegant moldings set the tone, and the family room is warmed by a gas fireplace. The primary suite has coffered ceilings and its own bath with a Jacuzzi tub.
The home has four bedrooms, four bathrooms (three full and one half) and 4,674 square feet. A finished bonus room above the three-car garage works well as a home office. The partially finished lower level adds a full bath with a heated floor, a wine cellar area and built-in surround sound. Out back there is a deck, and the property is near the train station, major highways, downtown and the waterfront. It last sold in 2007 for $625,000.
The home sold at its full asking price. Jill M. Taylor of RE/MAX Right Choice was the listing agent.
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No. 4 — $950,000 · 77 Merwin Avenue #A, Milford, Connecticut
This detached townhome is one of just five custom homes in a small community with private access to sandy Burwell Beach on Long Island Sound, and it has its own path down to the sand. Built in 2002 and sold as a condominium, it rises three stories, with an elevator serving the floors.
The main living level is open, with a kitchen built around a center island, dining and living areas, and a gas fireplace. Sliding doors lead out to a private balcony and deck with water and sunset views. On the entry level, a spacious foyer connects to the attached two-car garage, and a full bath there is handy after a day at the beach.
The primary suite takes up a level of its own, with a sitting area and fireplace, an adjoining room suited to an office, oversized walk-in closets and a bath with a Jacuzzi tub, double vanity and separate shower. Two more bedrooms share a full bath on the top floor. In all, the home has three bedrooms, four bathrooms (three full and one half) and 2,555 square feet. Milford’s beaches, downtown, the train station, I-95 and the Merritt Parkway are all close by. The property last sold in 2002 for $509,200.
Barbara Zink of Coldwell Banker Realty was the listing agent and also represented the buyer, so the same agent was on both sides of the sale. It was the second listing in this Top 5 for Coldwell Banker Realty, which also listed the top sale of the week in Woodmont.
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No. 5 — $855,000 · 12 Smith Street, East Haven, Connecticut
The only sale outside Milford is in East Haven, where this 1990 contemporary sits steps from Long Island Sound and the town’s beaches. Tweed New Haven Airport is less than 1.5 miles away, and Yale University and Yale New Haven Hospital are within minutes.
The cedar-sided home has four bedrooms, three bathrooms (two full and one half) and 3,510 square feet, with two fireplaces, a deck and a balcony. A private in-law suite with its own entrance gives the layout flexibility for extended family or guests. The 0.48-acre lot is level and private, with room for gardening and play, and there is a storage shed. The property last sold in 2007 for $572,000.
Joanne Fowler and Robert Bishop, both of Bishop, Edward & Roberts, LLC, were the listing agents, and Tara Davidson of LPT Realty – IConn Team represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, November 8, 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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