27 Dilliston Rd
New HartfordCT06057
Cheap Homes for Rent in Winchester, CT from $1,100 (13 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
111 Rockwell St, Unit A
111 Rockwell St
WinchesterCT06098
106 Rockwell St
WinchesterCT06098
47 Scoville Rd
CornwallCT06796
88 Spencer St
WinchesterCT06098
936 Main St
WinchesterCT06098
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.
250 Litchfield St
TorringtonCT06790
98 Spencer St
WinchesterCT06098
19 Center St
WinchesterCT06098
112 Rockwell St
WinchesterCT06098
181 Grove St
TorringtonCT06790
7 Swaller Hill Rd
SharonCT06069
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.
335 Taylor Brook Rd
WinchesterCT06098
Showing Results 1-13, 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 | $2,035 | $1,190 | $3,700 |
| Winchester 3 Bedroom Homes for Rent | $4,370 | $1,550 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $6,106 | $1,550 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $7,500 | $3,000 | $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
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Winchester, CT Local Guide
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Cheapest Available Winchester Apartments for Rent
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Gilbert Clock Apartments | Studio | Studio,1BA | $1,150 |
| Mill at Still River | 1BD Classic | 1BR,1BA | $1,500 |
Best Value Apartments for Rent in Winchester, CT
As of July 31, 2026 the best value apartment in the Winchester area is the $1.44 price per square foot 111 Rockwell St Model at 111 Rockwell St, Unit A in the in the Litchfield County neighborhood starting from $1,225. The second greatest value Winchester apartment is the 1BD Classic Model at Mill at Still River starting at $1,500 with a $1.97 price per square foot in the Litchfield County neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 111 Rockwell St, Unit A | 111 Rockwell St | 2BR,1BA | $1.44 |
| Mill at Still River | 1BD Classic | 1BR,1BA | $1.97 |
| 279 N Main St, Unit 8 | 279 N Main St | 1BR,1BA | $1.28 |
| Gilbert Clock Apartments | Studio | Studio ,1BA | $1.92 |
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
Real 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.
Read Article
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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 51 Apartments for Rent in Winchester, CT with pricing that ranges from $800 to $1,600. There are also 41 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,190 to $19,500.
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 $1,190 to $19,500 with an average monthly rent of $4,384.
How much are larger Three and Four Bedroom Rentals in Winchester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $1,550 to $1,550, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,550 to $15,000. Four Bedroom Single-Family rentals are also available starting from $1,550 and Four Bedroom Apartments start at $1,550.
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.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.