2 Bedroom Apartments for Rent in Winsted, CT (50 Rentals)

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18 Upland Rd
2 Bedroom Apartments

18 Upland Rd

18 Upland RdWinsted, CT 06098
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GreenRidge
2 Bedroom Apartments

GreenRidge

111 Torringford StWinsted, CT 06098
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175 Main St
2 Bedroom Apartments

175 Main St

175 Main StWinsted, CT 06098
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398-406 Main St
2 Bedroom Apartments

398-406 Main St

398-406 Main StWinsted, CT 06098

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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Glen Apartments
2 Bedroom Apartments

Glen Apartments

130 Willow StWinsted, CT 06098
Senior Living
  • Utilities Included
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75-95 Hurlbut St
2 Bedroom Apartments

75-95 Hurlbut St

75-95 Hurlbut StWinsted, CT 06098

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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Highcroft Apartments
$2,550 - $2,870
Total Monthly Price

Total Monthly Price

Base Rent
$2,120 - $3,100
Required Monthly Fees
$54

Total Monthly Price
$2,174 - $3,154
2 Bedroom Apartments Available Now

Highcroft Apartments

1100 Highcroft PlSimsbury, CT 06070
Corporate Housing
  • Verified
  • Customer Reviewed
  • Utilities Included

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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Canal Place
$2,340 - $2,440
Total Monthly Price

Total Monthly Price

Base Rent
$1,895 - $3,085
Required Monthly Fees
$5

Total Monthly Price
$1,900 - $3,090
2 Bedroom Apartments Available Apr 22

Canal Place

1 Old Canal WayWeatogue, CT 06089
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour
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ReNew Bristol
$1,951 - $3,001
Total Monthly Price

Total Monthly Price

Base Rent
$1,831 - $3,001

Total Monthly Price
$1,831 - $3,001
2 Bedroom Apartments Available Apr 3

ReNew Bristol

1175 Farmington AveBristol, CT 06010
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property at 22 Upson Ave

$1,500

Total Monthly Price

Total Monthly Price

Base Rent
$1,500

Total Monthly Price
$1,500

2 Bedroom, 1 Bath Home for Rent

Available Now

22 Upson Ave

WinchesterCT06098
property at 83 Hilltop Dr

$2,200

Total Monthly Price

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

83 Hilltop Dr

SimsburyCT06089
property at 444 Prospect St

$2,350

Total Monthly Price

Total Monthly Price

Base Rent
$2,350

Total Monthly Price
$2,350

2 Bedroom, 1 Bath Condo for Rent

Available Now

444 Prospect St

TorringtonCT06790

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

property at 5 Niles Rd

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

2 Bedroom, 1 Bath Home for Rent

Available Now

5 Niles Rd

New HartfordCT06057
property at 187 Lovers Ln

$2,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,450

Total Monthly Price
$2,450

2 Bedroom, 2 Bath Condo for Rent

Available Now

187 Lovers Ln

TorringtonCT06790
property at 178 Edgewood Dr

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 1 Bath Home for Rent

Available Now

178 Edgewood Dr

TorringtonCT06790
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52 High St
2 Bedroom Apartments

52 High St

52 High StBristol, CT 06010
Corporate Housing
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267 Rockwell St
2 Bedroom Apartments

267 Rockwell St

267 Rockwell StWinchester, CT 06098
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Ensign House
2 Bedroom Apartments

Ensign House

690 Hopmeadow StSimsbury, CT 06070
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Holly House
2 Bedroom Apartments

Holly House

23 Holly House StLitchfield, CT 06759
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29 Water St Apartments
2 Bedroom Apartments

29 Water St Apartments

29-57 Water StTorrington, CT 06790
Corporate Housing
  • Utilities Included

Winsted, CT Local Guide

Largest Available Winsted and Nearby 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winsted, CT is found at The Grand Ryefield in the Bloomfield Windsor neighborhood and is 2,237 square feet priced from $3,475. The Preserve at Great Pond in the Poquonock neighborhood has the second largest 2 Bedroom, which is sized at 1,415 square feet and currently listed start at $3,055. Here is today’s list of the largest available 2 Bedroom units in Winsted:

Apartment ListingModel NameSquare FootagePriced From
The Grand RyefieldTownhome F2,237 Sq Ft$3,475
The Preserve at Great PondThe Farmington 21,415 Sq Ft$3,055
Mill CommonsThe Ensign1,410 Sq Ft$3,293
Alexandria Manor2BD 2BA1,311 Sq Ft$2,346
Station 2802 Bedroom 2 Bathroom D1,306 Sq Ft$2,766
Greenway Village2 Bedroom - End Unit1,300 Sq Ft$2,550
Avon PlaceLaurelside1,273 Sq Ft$2,900
Highcroft ApartmentsUpland1,240 Sq Ft$2,924
Aspen Green at Simsbury$2.40/sq.ft. - The Elm1,220 Sq Ft$2,925
The Pointe at Dorset CrossingBeech1,159 Sq Ft$2,492

Cheapest Available Winsted and Nearby 2 Bedroom Apartments

As of March 12, 2026 the lowest priced 2 Bedroom apartment unit in Winsted, CT is the Two Bedroom Model starting from $1,350 at Gilbert Clock Apartments . The second most affordable Winsted 2 Bedroom is the Two Bedroom Model at Winthrop Court Apartments starting at $1,350 . The average price for all 2 Bedroom apartments in Winsted is currently $2,588. Here is today’s list of the cheapest available 2 Bedroom options in Winsted:

Apartment ListingModel NamePriced From
Gilbert Clock ApartmentsTwo Bedroom$1,350
Winthrop Court ApartmentsTwo Bedroom$1,350
Mill at Still River1-2 BD$1,800
Avon Woods Apartments2 Bedroom - Renovated$2,125
Alexandria Manor2BD 1BA Remodel$2,255
King's Ridge (small quiet community)Two Bedroom 1.5 bath$2,325
Avon PlaceBeechwood$2,400
The Oliver BloomfieldB1$2,441
The Pointe at Dorset CrossingBeech$2,492
Greenway Village2 Bedroom$2,550

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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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.

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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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Remember the 3 Rules of Real Estate:
Location, Location, Location!

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Frequently Asked Questions about 2 Bedroom Winsted Apartments

What is the Cheapest apartment in Winsted with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winsted is at Gilbert Clock Apartments listed at $1,350.

How much is the average rent for a 2 Bedroom Winsted Apartment?

The average rent for a 2 Bedroom Apartment in Winsted is $2,588.

What is the largest available 2 Bedroom Winsted Apartment for rent?

Today's apartment with the most square footage in Winsted is a 2,237 square feet unit starting from $3,475 at The Grand Ryefield.

What is the average size for Winsted 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Winsted is currently 1,169 sq ft.

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

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

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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.

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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.

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A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment

Written by: Bob Mallory

Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.