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Chester, CT Homes for Rent

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  • /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
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    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    6 Pleasant St Unit 2, Chester, CT 06412

    CLEAN AND SPACIOUS 2 BEDROOM W/ LARGE EAT-IN KITCHEN / PAINTED AND REDONE HARDWOOD FLOORS / NEW REFRIGERATOR AND NEW ELECTRIC OVEN RANGE / HEAT, WATER & TRASH INCLUDED, PLUS A ONE CAR GARAGE!!! DOUBLE PANE INSULATED WINDOWS NICE OUTSIDE COVERED FRONT PORCH ~ I WOULD NOT WAIT ON THIS ONE!!

    Tom Clancy William Pitt Sotheby's Int'l

    6 Pleasant St Unit 2, Chester, CT 06412
  • /18

    $2,100 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
  • /40

    $1,950 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Apartment for Rent

    19 Denlar Dr, Chester, CT 06412

    Large 1200 sf 2 bedroom unit in 6 unit apartment building with updated kitchen and refinished hardwood floors throughout. Apartment features include living room with hardwood floors and sliders to a private balcony. A full bath serves the two 2nd floor bedrooms. The large open room in the lower level can be used as a family room, recreation/playroom or exercise room. The lower level also includes

    Pat Callahan Coldwell Banker Realty

    19 Denlar Dr, Chester, CT 06412
  • /20

    $2,300 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
  • /19

    $5,000 Per Month

    • 4 Beds
    • 2 Baths
    • 2,383 Sq Ft
    • House for Rent

    70 Goose Hill Rd, Chester, CT 06412

    FULLY FURNISHED RENTAL OPPORTUNITY!!! Beautifully remodeled home situated on park-like grounds located in idyllic Chester. The first floor features an open floor plan with remodeled chef's kitchen opening to dining room with wide plank flooring, skylights and vaulted ceilings. Family room includes fireplace and recessed lighting and wood stove. The full bathroom has been recently remodeled and

    Matthew Guida Eagle Eye Realty PLLC

    70 Goose Hill Rd, Chester, CT 06412
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    $2,200 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,481 Sq Ft
    • House for Rent

    64 Winter Ave, Deep River, CT 06417

    3 Bedroom, 1 1/2 bath home conveniently located close to Deep River town center. Enclosed porch, built-in cabinets in living room, hardwood floors, laundry in basement. Security Deposit and Credit Check required.

    Craig Milton Re/Max Valley Shore

    64 Winter Ave, Deep River, CT 06417

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 $2,025 per month, though prices vary by neighborhood, size, and property type. As of September 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 $81,000 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 $2,025 per month in Chester, CT, renters typically need to show $6,075 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 22.6, 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

Number of Homes for Rent
7
Median Rent
$2,025
Median Single Family Home Rent
$2,300
Median Townhouse Rent
$1,750
Median Condo Rent
$2,200
How to Rent a Home