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Chester, CT Homes for Rent

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  • /21

    $2,500 Per Month

    • 2 Beds
    • 1.5 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 bustling 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) 981-0835

    55 Liberty St, Chester, CT 06412
  • /9

    $1,500 Per Month

    • 1 Bath
    • 4,060 Sq Ft
    • House for Rent

    184 Middlesex Ave Unit 6, Chester, CT 06412

    Well-maintained studio apartment in a prime Chester location. Bright, open layout with good natural light and efficient use of space. Kitchen includes modern appliances with dishwasher, updated countertops, and solid cabinet storage. In-unit washer and dryer. Quiet setting with landscaped grounds and off-street parking, just minutes to Chester Village shops, restaurants, and local amenities.

    Agent Photo

    Anthony Velez

    VC Property Group, LLC

    (860) 847-7480

    184 Middlesex Ave Unit 6, Chester, CT 06412
  • /13

    $2,600 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,337 Sq Ft
    • House for Rent

    64-68 Middlesex Turnpike, Chester, CT 06412

    1910 Chester Village single family home is ideally located near the town center with easy access to route 9. This comfortable and well maintained 3 bedroom home features an updated kitchen, separate dining room, and a living room with fireplace. There is a full bath that serves the bedrooms on the 2nd floor and a 1/2 bath on the first floor. The walk-up attic provides inside storage while a small

    Pat Callahan Coldwell Banker Realty

    64-68 Middlesex Turnpike, Chester, CT 06412
  • /18

    $2,400

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • House for Rent

    21 Winthrop Rd, Chester, CT 06412

    Charming and private Cape Cod-style home set on 2.81 acres with ample parking and outdoor space. Built in 1930 and recently painted, this well-maintained, move-in ready home offers over 1,200 square feet of living space. The layout features two bedrooms, 1.5 baths, a spacious living room, and a versatile dining room/den. Recent updates include new siding, refinished hardwood floors, new

    21 Winthrop Rd, Chester, CT 06412
  • /2

    $1,150

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • 29-A Main Street

    25-29 W Main St, Chester, CT 06412

    $1,150 per month1 bed, 1 bath2nd floor unit700 sq feetAvailable 6-1-26Tenant pay electricity and heat. Street parking, located in downtown Chester

    25-29 W Main St, Chester, CT 06412
  • /2

    $1,150

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • House for Rent

    42 W Main St, Chester, CT 06412

    $1,150 per month1 bed, 1 bath2nd floor unit700 sq feetAvailable 6-1-26Tenant pay electricity and heat. Street parking, located in downtown Chester

    42 W Main St, Chester, CT 06412
  • /6

    $1,150

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • 25 Main Street

    25 Main St Unit 1, Chester, CT 06412

    1 bed, 1 bath2nd floor unit700 sq feetAvailable 6-1-26Tenant pay electricity and heat. Street parking, located in downtown Chester

    25 Main St Unit 1, 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, 06371, 06426, 06498 and 06469.

Rental Home Trends in Chester, CT

Rental Home Trends

Number of Homes for Rent
7
Median Rent
$2,000
Median Single Family Home Rent
$2,300
Median Townhouse Rent
$1,750
Median Condo Rent
$1,950
How to Rent a Home