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Newest Homes for Rent in Chester, CT

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  • 55 Liberty St, Chester, CT 06412
    55 Liberty St, Chester, CT 06412
    55 Liberty St, Chester, CT 06412
    /21

    $2,500

    Total Monthly Price

    • 2 Beds
    • 3 Baths
    • 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

    55 Liberty St, Chester, CT 06412
  • 68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412
    68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412
    68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412
    /11

    $2,400

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412

    Private 1 bedroom apartment in rear of Victorian estate property. Completely remodeled everything is new and utilities are included. Flexible on length of stay. No smoking, no pets please. Washer/dryer hookups are included. Arrange visit by appointment.

    68 W Main St Unit The Side Door at 68 W Main, Chester, CT 06412
  • 86 Spring St, Chester, CT 06412
    86 Spring St, Chester, CT 06412
    86 Spring St, Chester, CT 06412
    /10

    $1,900

    Total Monthly Price

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

    86 Spring St, Chester, CT 06412

    AVAILABLE OCTOBER 2026: Recently renovated unit of a 2 family house in Chester CT. This 850 sq ft living space is heated by propane, has a flexible floor plan, in-unit laundry, new kitchen area floor & new fridge. 2 private entrances and outdoor space with small fire pit. Perfect for a solo renter or couple. WALK TO TOWN - just 8/10 mile to lovely downtown Chester. This charming, quaint town

    86 Spring St, Chester, CT 06412
Connecticut Middlesex County Chester

Newest Homes for Rent in Chester, CT

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 July 2026, townhouses tend to be the most affordable option while single-family homes and condos 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 21.2, 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 Trends in Chester, CT

There are currently 3 homes available for rent in Chester, CT. The median rent is $2,400 per month, with single-family homes renting at $2,400, townhouses at $1,750 and condos at $2,450.

Rental Home Trends

Number of Homes for Rent
3
Median Rent
$2,400
Median Single Family Home Rent
$2,400
Median Townhouse Rent
$1,750
Median Condo Rent
$2,450
How to Rent a Home

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