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Chester, CT Houses 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
  • /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

Frequently Asked Questions

How much does it cost to rent a single-family home in Chester, CT?
The median rent for a single-family 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 22.0, 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 Houses for Rent
2
Median Single Family Home Rent
$2,400
Median 3 Bedroom Single Family Home Rent
$2,600
How to Rent a Home