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Chester, CT Homes for Sale

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  • 135 Middlesex Ave, Chester, CT 06412
    135 Middlesex Ave, Chester, CT 06412
    135 Middlesex Ave, Chester, CT 06412
    /34

    $525,000 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    135 Middlesex Ave, Chester, CT 06412

    Did you ever wish that a waterfront home could be affordable?? Look no further .....This WATERFRONT home on Chester Cove has the most spectacular views! Steps to fishing or kayaking! Enjoy watching the wildlife from the 20x10 deck just off the kitchen/dining/living rooms. Wonderful light enters through the numerous windows on the first floor with it's open floor plan, full bath and sliders to the

    Lisa Genovali Re/Max Valley Shore

    135 Middlesex Ave, Chester, CT 06412
  • 288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    288 Middlesex Ave, Chester, CT 06412
    /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
  • 11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    /11

    $238,500

    • Land
    • 1.5 Acres
    • $159,000 per Acre

    11 Kings Hwy, Chester, CT 06412

    1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line

    Rachel Welch William Raveis Real Estate

    11 Kings Hwy, Chester, CT 06412
  • 59 Wig Hill Rd, Chester, CT 06412
    59 Wig Hill Rd, Chester, CT 06412
    59 Wig Hill Rd, Chester, CT 06412
    /38

    $695,000

    • 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
  • 11 Parker Hill Rd, Killingworth, CT 06419
    11 Parker Hill Rd, Killingworth, CT 06419
    11 Parker Hill Rd, Killingworth, CT 06419
    /28

    $690,000

    • 3 Beds
    • 2 Baths
    • 2,349 Sq Ft

    11 Parker Hill Rd, Killingworth, CT 06419

    Welcome to this thoughtfully built new construction ranch, completed in 2025 and set on over an acre in Killingworth. This 3-bedroom, 2 full bath home offers a bright, open layout with a flexible family room that could potentially be converted into a 4th bedroom or private suite, with its own entrance, bathroom and kitchenette. Step inside to a welcoming entryway leading into the open-concept

    Judith Chanman Century 21 Classic Homes

    11 Parker Hill Rd, Killingworth, CT 06419
Connecticut Middlesex County Chester

Real Estate & Homes for Sale in Chester, CT

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.

Learn more about living in Chester

Frequently Asked Questions

What is the average home price in Chester, CT?
Homes for sale in Chester, CT have an average home price of $783,277.
How many homes have sold over the last 12 months in Chester, CT?
41 homes have sold in Chester, CT over the last 12 months.
What are the most popular zip codes in Chester, CT?
The most popular zip codes in Chester, CT include 06412, 06417, 06442, 06419 and 06371.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $649,950. If you put a 20% down payment of $130,000 and had a 30-year fixed mortgage with an interest rate of 6.23%, your estimated principal and interest payment would be $3,190 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $137K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, CT?
Chester, CT has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Lyme-Old Lyme High School, Lyme-Old Lyme Middle School and Haddam-Killingworth High School. Browse all the schools in Chester, CT to learn more.

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 57 days on the market compared to the national average of 56 days. The median sale price for homes in Chester, CT over the last 12 months is $651,500, up 45% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$651,500
Median Single Family Sale Price
$663,250
Average Price Per Sq Ft
$342
Number of Homes for Sale
3
Last 12 months Home Sales
41
Months of Supply
0.90
Median List Price
$649,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
45%
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