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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
Apartments for Rent in Winchester, CT (92 Rentals)
335 Taylor Brook Rd
WinchesterCT06098
111 Rockwell St, Unit A
111 Rockwell St
WinchesterCT06098
279 N Main St
WinchesterCT06098
I 9 Nanni Dr
WinchesterCT06098
112 Rockwell St
WinchesterCT06098
19 Center St
WinchesterCT06098
98 Spencer St
WinchesterCT06098
43 Wallens St
WinchesterCT06098
88 Spencer St
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.
31 Woodruff Ave
WinchesterCT06098
106 Rockwell St
WinchesterCT06098
936 Main St
WinchesterCT06098
34 Rock St
WinchesterCT06098
880 W Wakefield Blvd
WinchesterCT06098
106 Rockwell St
WinchesterCT06098
112 Rockwell St
WinchesterCT06098
19 Center St
WinchesterCT06098
98 Spencer St
WinchesterCT06098
88 Spencer 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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$1,500 - $1,600
Plus Fees
1 Bedroom Apartments Available NowMill at Still River
101 Whiting StWinsted, CT 06098
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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
250 Litchfield St
TorringtonCT06790
56 Doman Dr
TorringtonCT06790
187 Lovers Ln
TorringtonCT06790
24 Country Club Rd
TorringtonCT06790
163 Beechwood Ave
TorringtonCT06790
27 Dilliston Rd
New HartfordCT06057
10 Park Mdw
New HartfordCT06057
Neighborhood & Market Insights: How to Choose the Right Area to Rent
Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.
320 Lakeshore Dr
SandisfieldMA01255
72 Sandy Beach Rd
GoshenCT06756
56 Tyler Lake Heights Rd
GoshenCT06756
205 E Hyerdale Dr
GoshenCT06756
177 W Hyerdale Dr
GoshenCT06756
5 Belshyre Ct
GoshenCT06756
707 Timber Ln
CantonCT06019
444 Cherry Brook Rd
CantonCT06019
15 Lower Rd
North CanaanCT06024
61 Kelly Ln
GranbyCT06035
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.
22 Thronebrook Rd
GranbyCT06090
10 Partridge Ct
SimsburyCT06070
3 Arrowhead Dr
SimsburyCT06092
21 Saddle Ridge Dr
SimsburyCT06092
50 Fox Den Rd
SimsburyCT06092
47 Scoville Rd
CornwallCT06796
63 Cemetery Hill Rd
CornwallCT06796
230 E Litchfield Rd
LitchfieldCT06759
8 Deming Rd
LitchfieldCT06759
174 S Shore Rd
SalisburyCT06068
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.
Showing Results 1-50, Page 1 of 2
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 | $1,231 | $800 | $1,600 |
| Winchester 2 Bedroom Apartments | $1,416 | $1,225 | $1,550 |
| Winchester 3 Bedroom Apartments | $1,550 | $1,550 | $1,550 |
| 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.
How much does it cost to rent a home in Winchester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| 2 Bedroom Homes | $2,088 | $1,190 | $3,700 |
| 3 Bedroom Homes | $4,370 | $1,550 | $10,000+ |
| 4 Bedroom Homes | $5,830 | $1,375 | $10,000+ |
| 5 Bedroom Homes | $7,500 | $3,000 | $10,000+ |
| 7 Bedroom Homes | $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 Apartments in Winchester
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Winchester, CT Local Guide
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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.
Read Article
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.
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.
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Quick Rent Budget Calculator
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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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See the most popular apartments and homes in Winchester, CT
Frequently Asked Questions about Winchester
What is the current pricing and availability for apartments for rent in Winchester, CT?
As of today, July 28, 2026, there are currently 92 available Winchester apartments priced from $800 to $1,600, with an average monthly rent of $1,333.
What is the current price range for One Bedroom Winchester Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $800 to $1,600 with an average monthly rent of $1,231.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,225 to $1,550. Today's average rental price for Two Bedrooms here is $1,416.
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
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.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.