These are the five highest-priced home sales reported in Shoreline & Lower River Valley, Connecticut for the week ending October 25, 2026, and together they total $5.524 million. Three were in Middlesex County and two in New Haven County, with Old Saybrook accounting for two of the sales and Madison, Branford and Westbrook one each.
All five are single-family homes, and their building dates run from 1840 to 2019.
No. 1 — $1,350,000 · 1308 Durham Road, Madison, Connecticut
The oldest home in this Top 5 also has the most land. The Colonial at 1308 Durham Road in Madison was built in 1840 and sits on 4.38 acres, a wooded and landscaped property that borders open space. The property last sold for $1.3 million in 2025.
Inside, oak hardwood floors run through the home, which has three bedrooms, two full baths and a half bath in 2,767 square feet. The updated kitchen has Calacatta Gold marble countertops and stainless steel appliances, and there is a fireplace.
Outdoors, an in-ground gunite pool comes with a pool house, and the property also has a cabana, a porch and a patio. A carriage house has a three-bay garage with a guest suite above it, which has two bedrooms and a full bath of its own. Below the main home is a full walk-out basement.
Nick K. Prevost of William Raveis Real Estate was the listing agent, and David Mayhew of Pearce Real Estate represented the buyer. The sale, the highest-priced of the week, was one of two William Raveis Real Estate listings in this Top 5, along with the No. 3 sale in Stony Creek.
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No. 2 — $1,200,000 · 108 Maple Avenue, Old Saybrook, Connecticut
The home at 108 Maple Avenue in Old Saybrook has 278 feet of frontage on South Cove, on 1.8 acres set well back from the road. The cedar-sided Contemporary was built in 1965 and rebuilt in 1991, with vaulted ceilings and large windows that look toward the water.
At 3,188 square feet it is the largest home in this Top 5, and its four bedrooms and four bathrooms, two full and two half, are the most of the five. In the living room, a gas fireplace and a wet bar sit among custom built-ins, and sliding doors open to a deck overlooking the cove. The kitchen opens into a vaulted family room and to a 300-square-foot enclosed porch.
The primary suite is on the main level, with a vaulted ceiling, water views, access to a deck, two bathrooms and a 120-square-foot walk-in closet. A formal dining room, another bedroom and a laundry room are also on the first floor, and upstairs, two more bedrooms share a Jack-and-Jill bath.
Jessica L. Blancato of William Pitt Sotheby’s Int’l was the listing agent, and Kelly Puorro of Puorro Realty Group represented the buyer in the week’s second-highest sale.
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No. 3 — $1,050,000 · 34 Squaw Brook Road, Branford, Connecticut
Stony Creek, the Branford village known for the Thimble Islands, is the setting for the No. 3 sale. The home at 34 Squaw Brook Road is on a cul-de-sac, on 1.51 acres that border open space, and is steps from the town beach.
Built in 1974, the Contemporary mixes rustic craft with modern lines: beams of locally milled wood, hand-pegged hardwood floors and a brick fireplace that rises from floor to ceiling. The living area, dining area and kitchen share one open main level, and the kitchen has Bosch appliances. There is a window seat as well as a separate dining area, and a cable-railed deck looks out over natural surroundings toward a distant pond.
The primary suite, with its own full bath, is on the main level. So is a flexible room with a barn door and an atrium window that can work as a media room or sitting room. A spiral staircase climbs to a loft, and the lower level has a guest suite or home office with a private entrance. In all, the home has three bedrooms and three full baths in 1,632 square feet.
Vicky Welch and Steve Sinapis, both of William Raveis Real Estate, were the listing agents, giving the firm its second listing in this Top 5 after the No. 1 sale in Madison. Erin Connelly of Coldwell Banker Realty represented the buyer.
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No. 4 — $999,000 · 37 Woodland Drive, Old Saybrook, Connecticut
The smallest home and the smallest lot in this Top 5 belong to 37 Woodland Drive, a 1945 ranch on 0.33 acres in the Knollwood Beach neighborhood of Old Saybrook. It has views of the marsh and South Cove.
The 1,426-square-foot home has been remodeled inside. The white kitchen has quartz counters and a large center island, the family room has a fireplace, and a sunlit dining room that doubles as a sunroom looks out on the marsh and the cove. The primary bedroom is on the first floor, and there are two more bedrooms and two full baths. Outside are a patio and a large deck, and there is a full walk-out basement.
Knollwood Beach is a golf-cart community, and through its association, owners have beach rights, a clubhouse, tennis and pickleball courts and a playground. The property last sold for $620,000 in 2025.
The home sold at its full asking price of $999,000. Joel Lucas of Coldwell Banker Realty was the listing agent, and Heather Dacey of William Raveis Real Estate represented the buyer.
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No. 5 — $925,000 · 4 Autumn Ridge, Westbrook, Connecticut
The newest home in the group is a Cape Cod built in 2019 on a cul-de-sac in Westbrook. The home at 4 Autumn Ridge sits on 1.10 acres, close to Westbrook’s beaches, shopping and dining.
Floor-to-ceiling windows light its open layout and look out on a deck and a patio. The first-floor primary suite has a custom closet system and a soaking tub. The home has three bedrooms, two full baths and a half bath in 2,085 square feet, along with a fireplace and an attached two-car garage.
The home went under contract 18 days after it was listed and sold for $76,000 above its $849,000 asking price. Cara P. Bernard of Coldwell Banker Realty was the listing agent, giving the firm a second listing in this Top 5 along with the Knollwood Beach home, and Jackie Lyman of Lyman 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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