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Winchester, CT Condos for Rent

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  • 17 Upson Ave Unit A, Winchester, CT 06098
    17 Upson Ave Unit A, Winchester, CT 06098
    17 Upson Ave Unit A, Winchester, CT 06098
    /6

    $1,200 Plus Fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    17 Upson Ave Unit A, Winchester, CT 06098

    Property Id: 2602485Beautiful and modest Studio for rent. Utilities included depending on occupancy amount. Area is surrounded by lakes, rivers and springs.

    (860) 421-4800

    17 Upson Ave Unit A, Winchester, CT 06098
  • 15 Upson Ave Unit Upson ave, Winsted, CT 06098
    15 Upson Ave Unit Upson ave, Winsted, CT 06098
    15 Upson Ave Unit Upson ave, Winsted, CT 06098
    /9

    $2,200

    Total Monthly Price

    • 4 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • Condo for Rent

    15 Upson Ave Unit Upson ave, Winsted, CT 06098

    Property is completely vacant and ready for move in. Serious inquiries only

    15 Upson Ave Unit Upson ave, Winsted, CT 06098
  • 215 N Main St Unit One bedroom, Winsted, CT 06098
    215 N Main St Unit One bedroom, Winsted, CT 06098
    215 N Main St Unit One bedroom, Winsted, CT 06098
    /10

    $1,050

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Condo for Rent

    215 N Main St Unit One bedroom, Winsted, CT 06098

    Available June 15th or July 1st. For rent, 1 bedroom apartment on the second floor of a 3 family home near NWCCC in Winsted. Spacious kitchen, large closet, porch overlooking the yard, off-street parking for 1 car. No smoking. No dogs. Cats ok. Water and trash pickup included. 1,050 a month. First month and 2 months security a start of 1 year lease. Tenant pays gas heat, electric, and

    215 N Main St Unit One bedroom, Winsted, CT 06098
  • I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
    /6

    $1,475

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,045 Sq Ft
    • 2 Bedroom Townhouse Apartment

    I 9 Nanni Dr Unit F-09, Winchester, CT 06098

    Discover the charm of Litchfield County living at Litchfield Heights. Our generously sized townhomes — over 1,000 square feet — have been thoughtfully upgraded with brand new white shaker cabinets, granite countertops, stainless steel appliances, and new vinyl plank flooring. Spacious bedrooms, remodeled bathrooms, private entrances, and backyard sliders round out everything you need to feel

    I 9 Nanni Dr Unit F-09, Winchester, CT 06098
Connecticut Litchfield County Winchester

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 $1,100 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while single-family homes 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 $48,000 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 $1,200 per month in Winchester, CT, renters typically need to show $3,600 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 24.0, 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.

Condo Rental Trends in Winchester, CT

There are currently 4 condos available for rent in Winchester, CT. The median rent is $1,100 per month, with 1-bedroom condos renting at $1,100 and 2-bedroom condos at $1,238.

Rental Home Trends

Number of Condos for Rent
4
Median Condo Rent
$1,100
Median 1 Bedroom Condo Rent
$1,100
Median 2 Bedroom Condo Rent
$1,238
How to Rent a Home

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