$1,000
Total Monthly Price
Total Monthly Price
Base Rent
$1,000
Utilities & Essentials
Varies
Total Monthly Price
$1,000
Studio, 1 Bath Condo for Rent
Available Now
3 Goodwin Pl
AvonCT06001
Cheap Homes for Rent in Winchester, CT from $1,000 (8 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
3 Goodwin Pl
AvonCT06001
63 Water St
TorringtonCT06790
21 Prospect St
TorringtonCT06790
29 Benton St
WinchesterCT06098
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
161 Kinney St
TorringtonCT06790
473 Winchester Rd
WinchesterCT06098
130 Main St
CantonCT06019
134 SantaMaria Dr
TorringtonCT06790
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
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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 | $2,533 | $1,600 | $5,500 |
| Winchester 3 Bedroom Homes for Rent | $2,619 | $1,900 | $3,635 |
| Winchester 4 Bedroom Homes for Rent | $3,899 | $2,750 | $6,000 |
| Winchester 5 Bedroom Homes for Rent | $11,500 | $10,000 | $10,000+ |
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 and Nearby
| 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 and Nearby
As of October 27, 2025 the best value apartment in the Winchester area is the $1.97 price per square foot 1BD Classic Model at Mill at Still River in the starting from $1,500. The second greatest value Winchester apartment is the Studio Model at Gilbert Clock Apartments starting at $1,150 with a $1.92 price per square foot . 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. |
|---|---|---|---|
| Mill at Still River | 1BD Classic | 1BR,1BA | $1.97 |
| Gilbert Clock Apartments | Studio | Studio ,1BA | $1.92 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
Read Article
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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleQuick Rent Budget Calculator
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Explore Winchester, CT Rentals by Map
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 50 Apartments for Rent in Winchester, CT with pricing that ranges from $1,150 to $2,500. There are also 36 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,000 to $11,500.
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 $1,000 to $11,500 with an average monthly rent of $3,916.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.