5

Winchester, CT Condos for Rent

Section Image
  • 506 Main St, New Hartford, CT 06057
    506 Main St, New Hartford, CT 06057
    506 Main St, New Hartford, CT 06057
    /20

    $2,800 Plus Fees

    • 3 Beds
    • 1.5 Baths
    • 1,510 Sq Ft
    • Condo for Rent

    506 Main St, New Hartford, CT 06057

    Historic charm meets modern convenience in this updated 3-bedroom, 1.5 bath duplex located in the heart of New Hartford, CT. Built circa 1900, this spacious 1,510 sq. ft. home offers preserved character with thoughtful updates throughout. Available for immediate occupancy, the home features a spacious kitchen with new roof, dishwasher, refrigerator, gas range, washer, and gas dryer.

    506 Main St, New Hartford, CT 06057
  • C Dr Unit H-04, Winchester, CT 06098
    C Dr Unit H-04, Winchester, CT 06098
    C Dr Unit H-04, Winchester, CT 06098
    /14

    $1,595

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • H-04 Nanni Drive

    C Dr Unit H-04, Winchester, CT 06098

    Nestled in the Hills of Litchfield County, our Large Town Homes Offer:• Updated eat in kitchen with dishwasher and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Bathroom.• Private Entrances with walk out basements and washer/dryer hookups.• Over 1000 square feet of living space with heat and hot water included.Please come see

    C Dr Unit H-04, Winchester, CT 06098
  • 21 Mountain View Terrace Unit 21-02, Winchester, CT 06098
    21 Mountain View Terrace Unit 21-02, Winchester, CT 06098
    21 Mountain View Terrace Unit 21-02, Winchester, CT 06098
    /15

    $1,595

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,095 Sq Ft
    • 21-02 Mountain View Terrace

    21 Mountain View Terrace Unit 21-02, Winchester, CT 06098

    Nestled in the Hills of Litchfield County, our Large Town Homes Offer:• Updated eat in kitchen with dishwasher and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Bathroom.• Private Entrances with walk out basements and washer/dryer hookups.• Over 1000 square feet of living space with heat and hot water included.Please come see

    21 Mountain View Terrace Unit 21-02, Winchester, CT 06098
  • D 1 Nanni Dr Unit J-01, Winchester, CT 06098
    D 1 Nanni Dr Unit J-01, Winchester, CT 06098
    D 1 Nanni Dr Unit J-01, Winchester, CT 06098
    /17

    $1,595

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • J-01 Nanni Drive

    D 1 Nanni Dr Unit J-01, Winchester, CT 06098

    Nestled in the Hills of Litchfield County, our Large Town Homes Offer:• Updated eat in kitchen with dishwasher and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Bathroom.• Private Entrances with walk out basements and washer/dryer hookups.• Over 1000 square feet of living space with heat and hot water included.Please come see

    D 1 Nanni Dr Unit J-01, Winchester, CT 06098
  • B 7 Nanni Dr Unit G-07, Winchester, CT 06098
    B 7 Nanni Dr Unit G-07, Winchester, CT 06098
    B 7 Nanni Dr Unit G-07, Winchester, CT 06098
    /15

    $1,525

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • G-07 Nanni Drive

    B 7 Nanni Dr Unit G-07, Winchester, CT 06098

    Nestled in the Hills of Litchfield County, Our Large Town Homes Offer:• Updated eat in kitchens with dishwashers and modern flooring. • Spacious bedrooms with new six panel doors and sliders.• Remodeled Bathroom.• Private Entrances, one with a Slider • Over 1000 square feet of living space with heat and hot water included.Please come see why at Litchfield Gardens

    B 7 Nanni Dr Unit G-07, Winchester, CT 06098
Connecticut Litchfield County

Condos for Rent in Winchester, CT

Frequently Asked Questions

How much does it cost to rent a condo in Winchester, CT?
The median rent for a condo in Winchester, CT is $1,560 per month, though prices vary by neighborhood, size, and property type. As of September 2026, single-family homes tend to be the most affordable option while condos and townhouses are currently more expensive.
How much do you need to make to afford rent in Winchester, CT?
To comfortably afford the median rent in Winchester, CT, a household needs to earn roughly $63,800 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 $1,595 per month in Winchester, CT, renters typically need to show $4,785 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 Winchester, CT?
In Winchester, CT, the price-to-rent ratio is 19.3, 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 Winchester, CT are best for renting a condo?
The best neighborhood for renting in Winchester, CT depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a condo include Downtown Bristol, Federal Hill, West End/Bristol and South Bristol, each with its own character and price range.

Condo Rental Trends in Winchester, CT

There are currently 5 condos available for rent in Winchester, CT. The median rent is $1,560 per month, with 1-bedroom condos renting at $1,365 and 2-bedroom condos at $1,595.

Rental Home Trends

Number of Condos for Rent
5
Median Condo Rent
$1,560
Median 1 Bedroom Condo Rent
$1,365
Median 2 Bedroom Condo Rent
$1,595
How to Rent a Home

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