40 High St
WinchesterCT06098
Cheap Apartments for Rent in Winchester, CT from $800 (24 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.
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$875
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$875
Total Monthly Price
$875
279 N Main St, Unit 7, Unit 7
279 N Main StWinchester, CT 06098
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$8751 Bedroom Apartments Available Now
279 N Main St, Unit 7
279 N Main StWinchester, CT 06098
277 N Main St
WinchesterCT06098
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$1,0501 Bedroom Apartments Available Now
12 Beach St, Unit 1
12 Beach StWinchester, CT 06098
440 Main St
WinchesterCT06098
22 Upson Ave
WinchesterCT06098
25 Lake St
WinchesterCT06098
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
5 Brookside Ave
WinchesterCT06098
20-22-22 Allen St
WinchesterCT06098
165 Elm St
WinchesterCT06098
174 Main St
WinchesterCT06098
25 Lake St
WinchesterCT06098
165 Elm St
WinchesterCT06098
174 Main St
WinchesterCT06098
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$1,0501 Bedroom Apartments Available Now
12 Beach St, Unit 7
12 Beach StWinsted, CT 06098
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.
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$1,150 - $1,550
Plus Fees12 Month Lease Term
Studio to 2 Bedroom Apartments Available NowGilbert Clock Apartments
13 Wallens StWinsted, CT 06098
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$1,495
Plus Fees12 Month Lease Term
2 Bedroom Apartments Contact Us For AvailabilityLitchfield Heights
15 Mountain View TerraceWinsted, CT 06098
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$1,500 - $1,800
Plus Fees
1 to 2 Bedroom Apartments Available NowMill at Still River
101 Whiting StWinsted, CT 06098
27 Dilliston Rd
New HartfordCT06057
839 Main St
TorringtonCT06790
194 Washington Ave
TorringtonCT06790
21 Woodbine St
TorringtonCT06790
5 Niles Rd
New HartfordCT06057
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.
Showing Results 1-24, 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 an apartment in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Cheap Winchester Studio Apartments | $1,250 | $1,150 | $1,350 |
| Cheap Winchester 1 Bedroom Apartments | $1,096 | $850 | $1,600 |
| Cheap Winchester 2 Bedroom Apartments | $1,577 | $1,200 | $2,500 |
| Cheap Winchester 3 Bedroom Apartments | $1,972 | $1,495 | $2,450 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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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 April 28, 2026 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 279 N Main St Model at 279 N Main St, Unit 7 starting at $875 with a $1.28 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 |
| 279 N Main St, Unit 7 | 279 N Main St | 1BR,1BA | $1.28 |
| Gilbert Clock Apartments | Studio | Studio ,1BA | $1.92 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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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 ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Frequently Asked Questions about Cheap Winchester Apartments
How much is rent for a Cheap One Bedroom Winchester Apartment?
The lowest price for a Cheap One Bedroom Winchester Apartment is $1,250 at Gilbert Clock Apartments.
What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $1,350 at Gilbert Clock Apartments.
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
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.