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Chester, CT Homes for Rent

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  • /27

    $2,500 total monthly price

    • 2 Beds
    • 2.5 Baths
    • 1,328 Sq Ft
    • House for Rent

    55 Liberty St, Chester, CT 06412

    Academic rental located in the charming town of Chester Connecticut. Ideally located for access to nearby colleges including Wesleyan and Connecticut College. This adorable, well maintained home is located just over a mile from the inviting downtown center of Chester with its delicious restaurants and interesting shops. The home has a lovely open floor plan on the main level which includes an

    Agent Photo

    Janet Cronin-Rumanoff

    William Pitt Sotheby's Int'l

    (860) 730-1941

    55 Liberty St, Chester, CT 06412
  • /3

    $2,400 per month plus fees

    • 3 Beds
    • 1.5 Baths
    • 1,190 Sq Ft
    • House for Rent

    17 Pratt St, Chester, CT 06412

    Welcome to your new home in the heart of Chester Center, CT! This charming property offers a comfortable living space perfect for those looking for convenience and style. Embrace the vibrant lifestyle with several outstanding restaurants just a stone's throw away, ensuring you’ll always have delightful dining options at your fingertips.The residence features well-appointed bedrooms and

    17 Pratt St, Chester, CT 06412
  • /20

    $2,200 total monthly price

    • 3 Beds
    • 1 Bath
    • 1,366 Sq Ft
    • House for Rent

    15 Laurel St, Chester, CT 06412

    Three-bedroom rental featuring one full bathroom, a private back patio, and an attached one-car garage. The lower level is partially finished, offering additional living or storage space. Located near Cedar Lake, this home includes new double-paned, energy-efficient windows throughout. Credit and background/criminal checks are required with application submission.

    Craig Milton Re/Max Valley Shore

    15 Laurel St, Chester, CT 06412
  • /17

    $1,950 total monthly price

    • 2 Beds
    • 1 Bath
    • 790 Sq Ft
    • Apartment for Rent

    159 W Main St Unit E, Chester, CT 06412

    SPACIOUS 2 BEDROOM RANCH APARTMENT WITH NEWLY RENOVATED KITCHEN / LOCATED IN PICTURESQUE MIXED USE BUILDING / FRESHLY PAINTED WITH NEW APPLIANCES, HARDWOOD FLOORS & 9 FOOT CEILINGS / MAIN BEDROOM HAS WALKIN CLOSET / ENJOY HIKING & LIVING NEXT TO "NORTH QUARTER PARK" AND THE CONVENIENCE OF BEAUTIFUL DOWNTOWN CHESTER

    Tom Clancy William Pitt Sotheby's Int'l

    159 W Main St Unit E, Chester, CT 06412
  • /39

    $7,500 total monthly price

    • 4 Beds
    • 4.5 Baths
    • 4,708 Sq Ft
    • House for Rent

    15 Liberty St, Chester, CT 06412

    Exceptional Rental Opportunity in Chester's Quintessential New England Village. Experience refined living in this estate-like setting, exquisitely furnished and thoughtfully remodeled to the highest standards. Offering over 4,000 sq. ft. of light-filled luxury, this stunning home is available October 2025 through mid-May 2026. Property Highlights: 4 Bedrooms | 5 Baths - including an

    Lynn Lehrman Re/Max Valley Shore

    15 Liberty St, 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.

Frequently Asked Questions

What are the most popular neighborhoods in Chester, CT for renters?
The most popular neighborhood in Chester, CT for renters is Westfield.
What are the most popular zip codes in Chester, CT for renters?
The most popular zip codes in Chester, CT for renters include 06412, 06423, 06371, 06442 and 06426.
How to Rent a Home