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Newest Homes for Rent in Chester, CT

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  • 159 W Main St Unit B, Chester, CT 06412
    159 W Main St Unit B, Chester, CT 06412
    159 W Main St Unit B, Chester, CT 06412
    /15

    $1,900 Per Month

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

    159 W Main St Unit B, Chester, CT 06412

    LARGE 2 BEDROOM APARTMENT WITH NEWLY REDONE HARDWOOD FLOORS / FRESHLY PAINTED / UNIT HAS IT'S OWN FULL SIZE STACK WASHER & DRYER / UNIT IS RANCH ON THE SECOND FLOOR

    Tom Clancy William Pitt Sotheby's Int'l

    159 W Main St Unit B, Chester, CT 06412
  • 138 W Main St, Chester, CT 06412
    138 W Main St, Chester, CT 06412
    138 W Main St, Chester, CT 06412
    /13

    $1,695

    Total Monthly Price

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

    138 W Main St, Chester, CT 06412

    Spacious one bedroom apartment in small quiet complex close to the quaint village of Chester. New kitchen, new carpet, wide plank floors, large windows, exposed beams in this antique colonial style restored barn, all set on well manicured grounds including stone walls and gardens; laundry in building; no dogs; easy access to I95 and Route 9. Tenant pays for electricity/heat/hot water. Rent $1695

    138 W Main St, Chester, CT 06412
  • 26 Ferry Rd Unit B, Chester, CT 06412
    26 Ferry Rd Unit B, Chester, CT 06412
    26 Ferry Rd Unit B, Chester, CT 06412
    /25

    $2,700 Per Month

    • 2 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • Apartment for Rent

    26 Ferry Rd Unit B, Chester, CT 06412

    A rare rental offering in one of Chester's most peaceful settings. Tucked into the woods with the Pattaconk Brook running just beyond the property, this beautifully renovated residence offers privacy and a wonderful connection to nature, just minutes from the heart of Chester Village. Inside, soaring ceilings and exposed timber beams create a bright, open living space full of architectural

    Aschly Daggett VC Property Group, LLC

    26 Ferry Rd Unit B, Chester, CT 06412
  • 100 W Main St Unit B, Chester, CT 06412
    100 W Main St Unit B, Chester, CT 06412
    100 W Main St Unit B, Chester, CT 06412
    /20

    $2,500 Per Month

    • 1 Bed
    • 1.5 Baths
    • 800 Sq Ft
    • Apartment for Rent

    100 W Main St Unit B, Chester, CT 06412

    Available 9/1/26! Taking applications now. Something special is happening at 100 W Main. This brand-new residence brings together thoughtful design, beautiful finishes, and the ease of modern living, all just minutes from the heart of Chester Village. **Unit B** has a style all its own. The bright, open living space centers around a beautifully finished kitchen with quartz countertops, a generous

    Aschly Daggett VC Property Group, LLC

    100 W Main St Unit B, Chester, CT 06412
  • 100 W Main St Unit A, Chester, CT 06412
    100 W Main St Unit A, Chester, CT 06412
    100 W Main St Unit A, Chester, CT 06412
    /18

    $2,300 Per Month

    • 1 Bed
    • 1 Bath
    • 750 Sq Ft
    • Apartment for Rent

    100 W Main St Unit A, Chester, CT 06412

    9/1/26 Move in! Taking applications. Something special is happening at 100 W Main. These brand-new residences bring together thoughtful design, beautiful finishes and the ease of modern living, all just minutes from the heart of Chester Village. Each home has its own personality, with carefully chosen kitchens and baths, warm wood tones, beautiful tilework, quality cabinetry and finishes that

    Aschly Daggett VC Property Group, LLC

    100 W Main St Unit A, Chester, CT 06412
Connecticut Middlesex County

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 $2,300 per month, though prices vary by neighborhood, size, and property type. As of August 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 $92,000 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 $2,300 per month in Chester, CT, renters typically need to show $6,900 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 20.5, 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 5 homes available for rent in Chester, CT. The median rent is $2,300 per month, with single-family homes renting at $2,300, townhouses at $1,750 and condos at $2,500.

Rental Home Trends

Number of Homes for Rent
5
Median Rent
$2,300
Median Single Family Home Rent
$2,300
Median Townhouse Rent
$1,750
Median Condo Rent
$2,500
How to Rent a Home

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