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Cheshire, CT Houses for Rent

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  • /3

    $2,495

    Total Monthly Price

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • House for Rent

    84 Main St Unit 1, Cheshire, CT 06410

    Pets allowed with restrictions, renters insurance required, application with credit and background with fee paid by applicant.

    84 Main St Unit 1, Cheshire, CT 06410
  • /7

    $1,600

    Total Monthly Price

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

    356 Highland Ave, Cheshire, CT 06410

    Amazing property and a great place to make a home-- We will have a 1 Bedroom coming available with new White Cabinets-- Also another lower level unit with the cabinets pictured. Don't wait to get in touch with us about these Great units in a fantastic location- No smoking, No pets-- Good credit and Good income needed to qualify. Heat and Hot water, cold water, sewer, trash included in the

    356 Highland Ave, Cheshire, CT 06410
  • /37

    $4,200 Per Month

    • 4 Beds
    • 3 Baths
    • 2,095 Sq Ft
    • House for Rent

    85 Brentwood Dr, Cheshire, CT 06410

    Beautiful 4 Bedroom House *w/ an In-Law* in Cheshire! Garage Parking, Central Air, & a Beautiful Backyard Main House Features: - 3 bedrooms - 2 bathrooms - Bright, open floor plan kitchen/living room with dining nook - Big kitchen with tons of prep space & newer appliances, perfect for any occasion! - Primary bedroom w/ an en-suite bathroom - Finished basement with 4th bedroom, bonus room, and

    Olivia Turek Farnam Realty Group

    85 Brentwood Dr, Cheshire, CT 06410
  • /35

    $3,990

    Total Monthly Price

    • 5 Beds
    • 3.5 Baths
    • 2,392 Sq Ft
    • House for Rent

    205 Jinny Hill Rd, Cheshire, CT 06410

    Experience comfort, space, and privacy in this one of a kind 5-bedroom, 3.5-bath home set beautifully landscaped acres. Designed with inspiration from Frank Lloyd Wright, this home offers a blend of character, modern updates, and flexible living space. Mini spits throughout the property for year round comfort.The remodeled kitchen features granite countertops, stainless steel appliances,

    205 Jinny Hill Rd, Cheshire, CT 06410
  • /21

    $2,500 Per Month

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

    1335 Wolf Hill Rd, Cheshire, CT 06410

    Renovated rental available in desirable Cheshire!

    George Daniolos eRealty Advisors, Inc.

    1335 Wolf Hill Rd, Cheshire, CT 06410
  • /15

    $3,340

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft
    • House for Rent

    233 S Rolling Acres Rd, Cheshire, CT 06410

    Welcome home to this spacious 3-bedroom, 2-bathroom home featuring beautiful hardwood floors throughout and central air conditioning for year-round comfort. The kitchen comes fully equipped with a stove, refrigerator, and dishwasher, while the partially finished basement offers additional living space, perfect for a family room, home office, or recreation area. Enjoy a private backyard with a

    233 S Rolling Acres Rd, Cheshire, CT 06410
  • /10

    $850 Per Month

    • 1 Bath
    • 184 Sq Ft
    • House for Rent

    19 Stony Hill Rd Unit 12, Cheshire, CT 06410

    Studio apartment ready for occupancy!! Heat and Hot Water included. Convenient location. 2 month's security plus 1st month's rent required to move in. Application, credit check, background and eviction check required. No Pets!! No smoking or any kind!! No laundry in unit or on site!! Excellent credit required.

    Ann Micacci Berkshire Hathaway NE Prop.

    19 Stony Hill Rd Unit 12, Cheshire, CT 06410
  • /17

    $2,000 Per Month

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

    1335 Wolf Hill Rd Unit 2nd Floor, Cheshire, CT 06410

    Renovated rental available in desirable Cheshire!

    George Daniolos eRealty Advisors, Inc.

    1335 Wolf Hill Rd Unit 2nd Floor, Cheshire, CT 06410
  • /23

    $3,000 Per Month

    • 3 Beds
    • 1.5 Baths
    • 2,200 Sq Ft
    • House for Rent

    402 W Main St, Cheshire, CT 06410

    You will not be disappointed in this newly remodeled 3 BR apt with modern appliances, new floors, walls, ceilings, and paint. Upgrades include the furnace system for efficiency. This is minutes away from major highways, great restaurants, and shopping. Off-street parking, a large level yard, and the landlord takes care of snow and lawn care. The property is immaculate and ready to be your next

    Joe Rodorigo Keystone Realty, LLC

    402 W Main St, Cheshire, CT 06410

Frequently Asked Questions

How much does it cost to rent a single-family home in Cheshire, CT?
The median rent for a single-family home in Cheshire, CT is $2,760 per month, though prices vary by neighborhood, size, and property type. As of July 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Cheshire, CT?
To comfortably afford the median rent in Cheshire, CT, a household needs to earn roughly $99,800 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 $2,495 per month in Cheshire, CT, renters typically need to show $7,485 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 Cheshire, CT?
In Cheshire, CT, the price-to-rent ratio is 17.7, 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.
What neighborhoods in Cheshire, CT are best for renting a single-family home?
The best neighborhood for renting in Cheshire, CT depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a single-family home include East End District, North End District, South End District, Village of Waterbury and Bunker Hill, each with its own character and price range.

Rental Home Trends

Number of Houses for Rent
9
Median Single Family Home Rent
$2,760
Median 3 Bedroom Single Family Home Rent
$2,750
Median 4 Bedroom Single Family Home Rent
$3,775
Median 5 Bedroom Single Family Home Rent
$3,990
How to Rent a Home