2 Bedroom Apartments for Rent in Winsted, CT (56 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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398-406 Main St
2 Bedroom Apartments

398-406 Main St

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

175 Main St

175 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
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Avon Woods Apartments
$2,125 - $2,325
Total Monthly Price

Total Monthly Price

Base Rent
$1,975 - $2,325

Total Monthly Price
$1,975 - $2,325
2 Bedroom Apartments Available Now

Avon Woods Apartments

75 Avonwood RdAvon, CT 06001
Student Housing
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The Preserve at Great Pond
Rent Specials
$2,525 - $3,054
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,920 - $2,995
Required Monthly Fees
$59

Total Monthly Price
$1,979 - $3,054
2 Bedroom Apartments Available Now

The Preserve at Great Pond

100 Lexington StWindsor, CT 06095
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Mill Commons
Rent Specials
$2,944 - $3,181
Total Monthly Price

Total Monthly Price

Base Rent
$2,944 - $3,181
Required Monthly Fees
$85

Total Monthly Price
$3,029 - $3,266
2 Bedroom Apartments Available Now

Mill Commons

1 Millers WaySimsbury, CT 06070
Corporate Housing
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  • Customer Reviewed
  • 3D Tour
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The Pointe at Dorset Crossing
Rent Specials
$2,327 - $2,410
Total Monthly Price

Total Monthly Price

Base Rent
$1,819 - $2,410
Required Monthly Fees
$77

Total Monthly Price
$1,896 - $2,487
2 Bedroom Apartments Available Now

The Pointe at Dorset Crossing

55 Dorset Crossing DrSimsbury, CT 06070
Corporate Housing
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  • Customer Reviewed
  • 3D Tour

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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Tellus Bloom
Rent Specials
$2,394 - $2,656
Total Monthly Price

Total Monthly Price

Base Rent
$2,394 - $3,331
Required Monthly Fees
$25

Total Monthly Price
$2,419 - $3,356
2 Bedroom Apartments Available Jan 27

Tellus Bloom

20 Jerome AveBloomfield, CT 06002
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Heirloom Flats
Rent Specials
$2,553 - $2,888
Total Monthly Price

Total Monthly Price

Base Rent
$1,815 - $2,888
Required Monthly Fees
$45

Total Monthly Price
$1,860 - $2,933
2 Bedroom Apartments Available Now

Heirloom Flats

700 Bloomfield AveBloomfield, CT 06002
Corporate Housing
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Highcroft Apartments
$2,590 - $3,410
Total Monthly Price

Total Monthly Price

Base Rent
$2,095 - $4,475
Required Monthly Fees
$54

Total Monthly Price
$2,149 - $4,529
2 Bedroom Apartments Available Now

Highcroft Apartments

1100 Highcroft PlSimsbury, CT 06070
Corporate Housing
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  • Utilities Included
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Tellus Green
Rent Specials
$2,749 - $2,899
Total Monthly Price

Total Monthly Price

Base Rent
$1,691 - $2,874
Required Monthly Fees
$25

Total Monthly Price
$1,716 - $2,899
2 Bedroom Apartments Contact Us For Availability

Tellus Green

713 Bloomfield AveBloomfield, CT 06002
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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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Farmington Court Apartments
$2,195 - $2,395
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,195 - $2,395

Total Monthly Price
$2,195 - $2,395
2 Bedroom Apartments Available Feb 13

Farmington Court Apartments

1449-1495 Farmington AveFarmington, CT 06032
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ReNew Bristol
$1,931 - $3,401
Total Monthly Price

Total Monthly Price

Base Rent
$1,861 - $3,401

Total Monthly Price
$1,861 - $3,401
2 Bedroom Apartments Available Now

ReNew Bristol

1175 Farmington AveBristol, CT 06010
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property at 31 Benton St

$1,600

Total Monthly Price

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

2 Bedroom, 2 Bath Home for Rent

Available Now

31 Benton St

WinchesterCT06098
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 135 Elm St

$1,700

Total Monthly Price

Total Monthly Price

Base Rent
$1,700

Total Monthly Price
$1,700

2 Bedroom, 1 Bath Home for Rent

Available Now

135 Elm St

WinchesterCT06098
property at 21 Oak Ave Ext

$1,650

Total Monthly Price

Total Monthly Price

Base Rent
$1,650

Total Monthly Price
$1,650

2 Bedroom, 1.5 Bath Condo for Rent

Available Now

21 Oak Ave Ext

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 11 Marion Ave

$1,695

Total Monthly Price

Total Monthly Price

Base Rent
$1,695

Total Monthly Price
$1,695

2 Bedroom, 1 Bath Condo for Rent

Available Now

11 Marion Ave

TorringtonCT06790
property at 98 E Elm St

$2,200

Total Monthly Price

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

2 Bedroom, 1 Bath Home for Rent

Available Now

98 E Elm St

TorringtonCT06790
property at 25 Cottage Grove Rd

$2,250

Total Monthly Price

Total Monthly Price

Base Rent
$2,250

Total Monthly Price
$2,250

2 Bedroom, 1 Bath Home for Rent

Available Now

25 Cottage Grove Rd

GoshenCT06756
property at 187 Lovers Ln

$2,250

Total Monthly Price

Total Monthly Price

Base Rent
$2,250

Total Monthly Price
$2,250

2 Bedroom, 1 Bath Condo for Rent

Available Now

187 Lovers Ln

TorringtonCT06790
property at 290 Cliffside Dr

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 2.5 Bath Condo for Rent

Available Now

290 Cliffside Dr

TorringtonCT06790
property at 6 Partridge Ct

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 2.5 Bath Home for Rent

Available Now

6 Partridge Ct

SimsburyCT06070
property at 31 Benton St

$1,600

Plus Fees12 Month Lease Term

2 Bedroom, 2 Bath Townhome for Rent

Available Now

31 Benton St

WinchesterCT06098
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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

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. Highcroft Apartments in the Terrys Plain neighborhood has the second largest 2 Bedroom, which is sized at 1,415 square feet and currently listed start at $3,464. 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
Highcroft ApartmentsVista1,415 Sq Ft$3,464
Mill CommonsThe Ensign1,410 Sq Ft$3,191
Alexandria Manor2BD 2BA1,311 Sq Ft$2,346
Greenway Village2 Bedroom - End Unit1,300 Sq Ft$2,550
Station 2802 Bedroom 2 Bathroom D3-b1,218 Sq Ft$2,770
ReNew BristolConcord1,200 Sq Ft$2,551
Aspen Green at Simsbury$2.36/sq.ft. - The Dogwood1,200 Sq Ft$2,825

Cheapest Available Winsted and Nearby 2 Bedroom Apartments

As of January 22, 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 $2,581. 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
22 High StB3$1,675
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
The Pointe at Dorset CrossingBeech$2,404
The Grand Luxury Apartments and HomesBirch$2,429
The Oliver BloomfieldB1$2,488

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

Explore Winsted, CT Rentals by Map

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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 $2,581.

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 1,421 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

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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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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.

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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.