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$800
Total Monthly Price12 Month Lease Term
1 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$800
Total Monthly Price
$800
279 N Main St, Unit 8
279 N Main StWinchester, CT 06098
Cheap Apartments for Rent in Winchester, CT from $800 (25 Rentals)
Search the lowest-cost Apartments available for rent right now in Winchester.
279 N Main St
WinchesterCT06098
43 Wallens St
WinchesterCT06098
31 Woodruff Ave
WinchesterCT06098
111 Rockwell St, Unit A
111 Rockwell St
WinchesterCT06098
106 Rockwell 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.
88 Spencer St
WinchesterCT06098
I 9 Nanni Dr
WinchesterCT06098
98 Spencer St
WinchesterCT06098
19 Center St
WinchesterCT06098
112 Rockwell St
WinchesterCT06098
335 Taylor Brook Rd
WinchesterCT06098
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.
106 Rockwell St
WinchesterCT06098
88 Spencer St
WinchesterCT06098
936 Main St
WinchesterCT06098
98 Spencer St
WinchesterCT06098
19 Center St
WinchesterCT06098
112 Rockwell St
WinchesterCT06098
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
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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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$1,225
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,225
Total Monthly Price
$1,225
111 Rockwell St, Unit A
111 Rockwell StWinsted, CT 06098
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$1,500 - $1,600
Plus Fees
1 Bedroom Apartments Available NowMill at Still River
101 Whiting StWinsted, CT 06098
27 Dilliston Rd
New HartfordCT06057
47 Scoville Rd
CornwallCT06796
250 Litchfield St
TorringtonCT06790
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.
7 Swaller Hill Rd
SharonCT06069
Showing Results 1-25, 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 | $1,231 | $800 | $1,600 |
| Cheap Winchester 2 Bedroom Apartments | $1,416 | $1,225 | $1,550 |
| Cheap Winchester 3 Bedroom Apartments | $1,550 | $1,550 | $1,550 |
| Cheap Winchester 4 Bedroom Apartments | $1,572 | $1,550 | $1,595 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments 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 29, 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.
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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.
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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
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.
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.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.