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Chester, CT Houses for Sale

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  • /38

    $3,150,000

    • 4 Beds
    • 6 Baths
    • 4,926 Sq Ft

    288 Middlesex Ave, Chester, CT 06412

    Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and

    Nancy Mesham Coldwell Banker Realty

    288 Middlesex Ave, Chester, CT 06412
  • /39

    $695,000

    • 4 Beds
    • 2.5 Baths
    • 2,029 Sq Ft

    226 Middlesex Ave, Chester, CT 06412

    Set back from the road on over two picturesque acres in historic Chester, this custom-built and thoughtfully designed Saltbox Colonial offers the perfect blend of timeless New England charm and modern home comforts. Lovingly maintained by the original owner, a gracious entry leads to a cozy family room centered around the fireplace, creating a warm and welcoming atmosphere year-round. The formal

    Peg Mitchel Coldwell Banker Realty

    226 Middlesex Ave, Chester, CT 06412
  • /38

    $724,000 Coming Soon

    • 5 Beds
    • 2.5 Baths
    • 3,862 Sq Ft

    59 Wig Hill Rd, Chester, CT 06412

    The spacious main house and separate guest/rental house sit on 3.64 park like acres abutting Chester Land Trust property. The front to back living/dining room features two large picture windows overlooking the rear landscape and a vaulted ceiling with second floor balcony. The cook's kitchen features newer appliances, granite counters, tile floor and eating area with sliding glass doors to a deck

    Joseph Kelly William Pitt Sotheby's Int'l

    59 Wig Hill Rd, Chester, CT 06412

Why Live in Chester

Chester, Connecticut, offers a serene lifestyle along the Connecticut River, characterized by its historical charm and picturesque views. The Chester-Hadlyme Ferry, one of the few operational ferries on the river, adds to the town's historical ambiance, especially in the downtown area, which features structures listed on the National Register of Historic Places. Chester's downtown is pedestrian-friendly, with unique architecture and a variety of dining options, such as River Tavern and Whistle Stop, making it a delightful spot for a leisurely afternoon. The town is known for its older Victorian, Cape Cod, and colonial homes, with expansive lot sizes and no homeowners associations. Chester is part of the tri-town area, including Essex and Deep River, and boasts a crime rate lower than the national average. Educational opportunities are strong, with Regional School District 4 and Chester Elementary School receiving high ratings for their academic programs and extracurricular activities. For outdoor enthusiasts, the Pattaconk Recreation Area offers woodland and grassland spaces leading to the reservoir's edge, perfect for picnics and relaxation. Chester is conveniently located near Tweed/New Haven Airport, less than an hour away, and is accessible via Route 9 and CTtransit bus stops, providing efficient transportation options.

Home Trends in Chester, CT

Housing Trends

Median Sale Price
$675,000
Median Single Family Sale Price
$695,000
Average Price Per Sq Ft
$335
Number of Homes for Sale
2
Last 12 months Home Sales
41
Months of Supply
0.60
Median List Price
$695,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
53%
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