The five highest-priced home sales publicly reported in the New Haven, Connecticut metro area for the week ending August 9, 2026, combined for $8.28 million. The week’s leader was an 1816 Federal-style residence on Liberty Street in Madison, which closed for $2,200,000 together with its newly built detached barn.
The closings ranged from $1,300,000 to $2,200,000 and stretched across the metro area, with sales recorded in Madison, Guilford, Milford, New Haven and Cheshire β including direct-waterfront properties on Long Island Sound in Guilford and Milford.
RealtyWireβs Top 5 ranks the five highest-priced residential closings it identified in the New Haven, Connecticut metro area for the reporting week. It may omit private, delayed, nondisclosed, or otherwise unreported transactions.
No. 1 — $2,200,000 · 137 Liberty Street, Madison, Connecticut
The week’s top sale closed for $2,200,000 on August 6, 2026: an 1816 Federal-style residence at 137 Liberty Street in Madison, sold with a newly built detached barn designed in a historical style, both renovated or built by design-build firm Gulick & Co., according to the listing. The five-bedroom, six-bath property spans a reported 5,543 square feet, which the listing describes as the house and barn combined β 3,784 square feet in the main residence and 1,776 in the barn.
Inside the main residence, wide-plank floors, custom millwork and formal parlors preserve the home’s early character, while a chef’s kitchen with Sub-Zero and Bosch appliances, a great room with an integrated home theater and an enclosed porch with a fireplace reflect the renovation. The primary suite adds bespoke cabinetry, a coffee station, a bar sink and a bath with a freestanding tub and oversized shower. The two-story barn holds a private office with a full bath upstairs and a first-floor accessory apartment with a full kitchen, oak floors, reclaimed ceiling beams, an accessible bath and its own septic system.
Alison S. Gould of Gould Group LLC was the listing agent. Margaret Muir of William Pitt Sotheby’s International represented the buyer.
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No. 2 — $1,720,000 · 136 Daniel Avenue, Guilford, Connecticut
In Guilford’s Indian Cove section, the waterfront home at 136 Daniel Avenue closed for $1,720,000 on August 5, 2026. Built in 2013, the house has an uncommon layout: a large one-bedroom plan with a bonus study, three baths and a reported 2,041 square feet, centered on a great room with high ceilings, a fireplace and a gourmet kitchen. The listing emphasizes the construction standard, crediting triple-glazed windows and both passive and active solar systems for heat and hot water with keeping utility bills close to nothing. Outside, a two-tiered patio is set into designed landscaping with views of Long Island Sound and Indian Cove, and the property has direct water access for swimming and boating, with an association beach about 100 steps away and an association dock nearby.
Leigh Whiteman of William Raveis Real Estate was the listing agent. Tim Galvin of William Raveis Real Estate represented the buyer.
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No. 3 — $1,699,900 · 216 Broadway, Milford, Connecticut
A direct-waterfront home in Milford’s Wildermere Beach neighborhood took third, closing for $1,699,900 on August 4, 2026. The year-round house at 216 Broadway, built in 1900, holds four bedrooms, two baths and a reported 2,046 square feet, with an open floor plan and water views from nearly every room. A wall of windows in the great room faces Long Island Sound, and French doors open onto a private sandy beach. The dining room seats ten to twelve, a breakfast bar in the kitchen adds seating for four, and a main-level office sits beside a full bathroom. The upper level carries the four bedrooms, an updated full bath and a laundry room. A covered waterfront patio rounds out the outdoor space, and the listing cites an excellent rental history plus quick access to major highways, downtown Milford and the harbor.
Marilyn Heffers of Coldwell Banker Realty was the listing agent. Amber G. Blake of Stacy Blake Realty LLC represented the buyer.
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No. 4 — $1,360,000 · 197 McKinley Avenue, New Haven, Connecticut
In New Haven’s Westville neighborhood, the renovated colonial at 197 McKinley Avenue closed for $1,360,000 on August 6, 2026. Described in the listing as a 1922 build, the five-bedroom, four-bath home keeps its original architectural details alongside updated heat, hot water, central air conditioning and electrical service across a reported 3,759 square feet. The living room holds a center fireplace and French doors to a heated sunroom with a stone fireplace, and the dining room opens to a kitchen with white cabinets, marble counters, a large island, two sink areas and Sub-Zero and Wolf appliances. The primary bedroom has a full bath and a two-section walk-in closet, two more bedrooms and a laundry area share the second floor, and the third floor adds two flexible rooms and a bath with a clawfoot tub. The listing places the house close to Yale, Yale New Haven Hospital and Westville Village.
Betsy Grauer of Betsy Grauer Realty, Inc was the listing agent. Jia Wu of JJ HOMES REAL ESTATE, LLC represented the buyer.
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No. 5 — $1,300,000 · 5 Melrose Drive, Cheshire, Connecticut
The fifth sale, at 5 Melrose Drive in Cheshire, closed for $1,300,000 on August 6, 2026. Built in 2022, the contemporary colonial offers four bedrooms, four baths and a reported 3,423 square feet, and the listing describes a new-construction feel with upgrades already in place. Hardwood floors run throughout, and a two-story great room with a gas fireplace opens to an eat-in kitchen with a center island, a six-burner gas range and a high-powered ventilation hood. The main level also holds a formal dining room, a living room, an office or bedroom beside a full bath, a mudroom and a laundry room. Upstairs, a double-entry primary suite carries an attached bonus room and a custom walk-in closet, and two secondary bedrooms share a Jack-and-Jill bath. A whole-house generator, an EV charger, a farmer’s porch and full irrigation on a level, landscaped lot round out the features.
Iris Meyer of William Raveis Real Estate was the listing agent. Susan Santoro of William Pitt Sotheby’s International represented the buyer.
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RealtyWire selected these transactions from publicly reported residential sales identified for the calendar week ending Sunday, August 9, 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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