135 Elm St
WinchesterCT06098
2 Bedroom Apartments for Rent in Winchester, CT (37 Rentals)
31 Benton St
WinchesterCT06098
22 Upson Ave
WinchesterCT06098
31 Benton St
WinchesterCT06098
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Rent Specials
$1,800
Plus Fees
2 Bedroom Apartments Available NowMill at Still River
101 Whiting StWinsted, CT 06098
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$1,495
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowLitchfield Heights
15 Mountain View TerraceWinsted, CT 06098
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Rent Specials
$1,350 - $1,550
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowGilbert Clock Apartments
13 Wallens StWinsted, CT 06098
188 E Lake St
WinstedCT06098
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.
38 Garden Ln
HarwintonCT06791
11 Marion Ave
TorringtonCT06790
161 Kinney St
TorringtonCT06790
77 Marion Ave
TorringtonCT06790
567 Firetown Rd
SimsburyCT06070
305 Timber Ln
CantonCT06019
187 Lovers Ln
TorringtonCT06790
25 Cottage Grove Rd
GoshenCT06756
213 Ledge Dr
TorringtonCT06790
Cash 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.
290 Cliffside Dr
TorringtonCT06790
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The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
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Showing Results 1-37, 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 |
|---|---|---|---|
| Winchester Studio Apartments | $1,250 | $1,150 | $1,350 |
| Winchester 1 Bedroom Apartments | $1,316 | $1,050 | $1,600 |
Winchester 2 Bedroom Apartments | $1,637 | $1,350 | $2,200 |
| Winchester 3 Bedroom Apartments | $1,800 | $1,800 | $1,800 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
See all Apartments in WinchesterExplore Winchester
Winchester, CT Local Guide
- Nearby Cities
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Largest Available Winchester and Nearby 2 Bedroom Apartments
The largest available 2 Bedroom apartment unit in Winchester, CT is found at Litchfield Heights and is 1,095 square feet priced from $1,495. Gilbert Clock Apartments has the second largest 2 Bedroom, which is sized at 1,000 square feet and currently listed start at $1,350. Here is today’s list of the largest available 2 Bedroom units in Winchester:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Litchfield Heights | 2 bedroom Town House | 1,095 Sq Ft | $1,495 |
| Gilbert Clock Apartments | Two Bedroom | 1,000 Sq Ft | $1,350 |
| Mill at Still River | 1-2 BD | 970 Sq Ft | $1,800 |
Cheapest Available Winchester and Nearby 2 Bedroom Apartments
As of December 21, 2025 the lowest priced 2 Bedroom apartment unit in Winchester, CT is the Two Bedroom Model starting from $1,350 at Gilbert Clock Apartments . The second most affordable Winchester 2 Bedroom is the 2 bedroom Town House Model at Litchfield Heights starting at $1,495 . The average price for all 2 Bedroom apartments in Winchester is currently $1,637. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Gilbert Clock Apartments | Two Bedroom | $1,350 |
| Litchfield Heights | 2 bedroom Town House | $1,495 |
| Mill at Still River | 1-2 BD | $1,800 |
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.
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The 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.
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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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Remember the 3 Rules of Real Estate:Location, Location, Location!
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Getting Around Winchester, CT
Walk Score®
17 / 100
Car-Dependent
Almost all errands require a car
Bike Score®
10 / 100
Somewhat Bikeable
Minimal bike infrastructure
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
- Walk Score® measures the walkability of any address.
- Transit Score® measures access to public transit.
- Bike Score® measures the bikeability of any address.
Frequently Asked Questions about 2 Bedroom Winchester Apartments
How much is the average rent for a 2 Bedroom Winchester Apartment?
The average rent for a 2 Bedroom Apartment in Winchester is $1,637.
What is the largest available 2 Bedroom Winchester Apartment for rent?
Today's apartment with the most square footage in Winchester is a 1,095 square feet unit starting from $1,495 at Litchfield Heights.
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
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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.