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Chester, CT Homes for Rent

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  • /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
  • /9

    $1,500 Plus Fees

    • Studio
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    184 Middlesex Turnpike 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

    (959) 666-6357

    184 Middlesex Turnpike Unit 6, Chester, CT 06412
  • /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
  • /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

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

How much does it cost to rent a home in Chester, CT?
The median rent for a home in Chester, CT is $2,400 per month, though prices vary by neighborhood, size, and property type. As of May 2026, townhouses tend to be the most affordable option while condos and single-family homes are currently more expensive.
How much do you need to make to afford rent in Chester, CT?
To comfortably afford the median rent in Chester, CT, a household needs to earn roughly $96,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $2,400 per month in Chester, CT, renters typically need to show $7,200 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Chester, CT?
In Chester, CT, the price-to-rent ratio is 21.6, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Home Trends in Chester, CT

Rental Home Trends

Number of Homes for Rent
5
Median Rent
$2,400
Median Single Family Home Rent
$2,400
Median Townhouse Rent
$1,750
Median Condo Rent
$2,225
How to Rent a Home