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Winchester, CT Condos for Rent

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  • 15 Upson Ave, Winchester, CT 06098
    15 Upson Ave, Winchester, CT 06098
    15 Upson Ave, Winchester, CT 06098
    /18

    $2,200 Plus Fees

    • 4 Beds
    • 1.5 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    15 Upson Ave, Winchester, CT 06098

    Property Id: 2145815Beautiful 4 bedroom for rent in Winsted Connecticut. Includes living, dining, kitchen,washroom, 4 beds and 1 1/2 bathroomAccepts Section 8

    (860) 407-5294

    15 Upson Ave, Winchester, 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
  • 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
  • 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

    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 Kitchen and Bathroom.• Private Entrances with Slider to backyard • Over 1000 square feet of living space with heat and hot water included.Please come see why at

    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 $1,000 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 $40,000 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 $1,000 per month in Winchester, CT, renters typically need to show $3,000 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 28.8, 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 and Forestville, each with its own character and price range.

Condo Rental Trends in Winchester, CT

There are currently 4 condos available for rent in Winchester, CT. The median rent is $1,000 per month, with 1-bedroom condos renting at $938 and 2-bedroom condos at $1,238.

Rental Home Trends

Number of Condos for Rent
4
Median Condo Rent
$1,000
Median 1 Bedroom Condo Rent
$938
Median 2 Bedroom Condo Rent
$1,238
How to Rent a Home

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