233 Roosevelt Ave
TorringtonCT06790
Cheap Homes for Rent in Winchester, CT from $700 (11 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
233 Roosevelt Ave
TorringtonCT06790
91 Elm St
WinchesterCT06098
63 Water St
TorringtonCT06790
27 Dilliston Rd
New HartfordCT06057
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
936 Main St
WinchesterCT06098
250 Litchfield St
TorringtonCT06790
24 Rock St
WinchesterCT06098
28 Carpenter Rd
New HartfordCT06057
839 Main St
TorringtonCT06790
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
11 Maple Ave
CantonCT06019
Showing Results 1-11, Page 1 of 1
Winchester, CT Local Guide
Mapple leaves by Marc Berry Reid is licensed under CC BY 2.0
How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,080 | $1,300 | $4,000 |
| Winchester 3 Bedroom Homes for Rent | $3,890 | $2,500 | $5,900 |
| Winchester 4 Bedroom Homes for Rent | $4,033 | $950 | $6,500 |
| Winchester 5 Bedroom Homes for Rent | $7,750 | $3,500 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $5,000 | $5,000 | $5,000 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winchester
Explore Winchester
Winchester, CT Local Guide
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Best Value Homes for Rent in Winchester, CT
As of September 22, 2026 the best value rental home in the Winchester area is the $1.85 price per square foot 506 Main St Model at 506 Main St in the West Granby neighborhood starting from $2,800. The second greatest value Winchester rental home is the 24 Rock St Model at 24 Rock St in the Litchfield County neighborhood starting at $1,500 with a $1.39 price per square foot. Here is today’s list of the best values for Winchester homes based on price per square foot:
| Home Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 506 Main St | 506 Main St | 3BR, 1.5BA | $1.85 |
| 24 Rock St | 24 Rock St | 2BR, 1BA | $1.39 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read Article
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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See the most popular apartments and homes in Winchester, CT
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 49 Apartments for Rent in Winchester, CT with pricing that ranges from $1,150 to $2,500. There are also 48 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $700 to $12,000.
What is the current price range for Rental Homes in Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $700 to $12,000 with an average monthly rent of $3,015.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Articles, How-To's, and Tips
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.