2 Bedroom Apartments for Rent in Winsted, CT (55 Rentals)

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property at 188 E Lake St

188 E Lake St

WinstedCT06098
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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
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18 Upland Rd
2 Bedroom Apartments

18 Upland Rd

18 Upland RdWinsted, 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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GreenRidge
2 Bedroom Apartments

GreenRidge

111 Torringford StWinsted, CT 06098
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Tellus Bloom
Rent Specials
$2,586 - $2,833
Total Monthly Price

Total Monthly Price

Base Rent
$2,336 - $3,316
Required Monthly Fees
$25

Total Monthly Price
$2,361 - $3,341
2 Bedroom Apartments Available Now

Tellus Bloom

20 Jerome AveBloomfield, CT 06002
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The Preserve at Great Pond
Rent Specials
$2,500 - $3,010
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,920 - $3,350
Required Monthly Fees
$15

Total Monthly Price
$1,935 - $3,365
2 Bedroom Apartments Available Now

The Preserve at Great Pond

100 Lexington StWindsor, CT 06095
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Avon Woods Apartments
$1,895 - $2,350
Total Monthly Price

Total Monthly Price

Base Rent
$1,595 - $2,350

Total Monthly Price
$1,595 - $2,350
2 Bedroom Apartments Available Now

Avon Woods Apartments

75 Avonwood RdAvon, CT 06001
Student Housing
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Mill Commons
Rent Specials
$2,999 - $3,284
Total Monthly Price

Total Monthly Price

Base Rent
$2,999 - $3,284
Required Monthly Fees
$112

Total Monthly Price
$3,111 - $3,396
2 Bedroom Apartments Available Now

Mill Commons

1 Millers WaySimsbury, CT 06070
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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 Pointe at Dorset Crossing
$2,560 - $2,799
Total Monthly Price

Total Monthly Price

Base Rent
$1,842 - $2,799
Required Monthly Fees
$77

Total Monthly Price
$1,919 - $2,876
2 Bedroom Apartments Available Now

The Pointe at Dorset Crossing

55 Dorset Crossing DrSimsbury, CT 06070
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Heirloom Flats
Rent Specials
$2,791 - $3,265
Total Monthly Price

Total Monthly Price

Base Rent
$2,200 - $3,672
Required Monthly Fees
$27

Total Monthly Price
$2,227 - $3,699
2 Bedroom Apartments Available Now

Heirloom Flats

700 Bloomfield AveBloomfield, CT 06002
Pet Friendly
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Highcroft Apartments
$3,010 - $3,605
Total Monthly Price

Total Monthly Price

Base Rent
$2,260 - $4,580
Required Monthly Fees
$48

Total Monthly Price
$2,308 - $4,628
2 Bedroom Apartments Available Now

Highcroft Apartments

900 Highcroft PlWeatogue, CT 06089
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Farmington Court Apartments
$1,995 - $2,235
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,995 - $2,235

Total Monthly Price
$1,995 - $2,235
2 Bedroom Apartments Available Nov 14

Farmington Court Apartments

1449-1495 Farmington AveFarmington, CT 06032
Family Friendly
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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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Tellus Green
Rent Specials
$2,749 - $2,899
Total Monthly Price

Total Monthly Price

Base Rent
$1,838 - $2,874
Required Monthly Fees
$25

Total Monthly Price
$1,863 - $2,899
2 Bedroom Apartments Contact Us For Availability

Tellus Green

713 Bloomfield AveBloomfield, CT 06002
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Canal Place
$2,220 - $2,320
Total Monthly Price

Total Monthly Price

Base Rent
$2,050 - $3,093
Required Monthly Fees
$5

Total Monthly Price
$2,055 - $3,098
2 Bedroom Apartments Available Now

Canal Place

1 Old Canal WayWeatogue, CT 06089
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property at 29 Benton St

29 Benton St

WinchesterCT06098

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.

property at 111 Rockwell St

111 Rockwell St

WinchesterCT06098
property at C 4 Nanni Dr

C 4 Nanni Dr

WinchesterCT06098
property at 217 N Main St

217 N Main St

WinchesterCT06098
property at 161 Kinney St

161 Kinney St

TorringtonCT06790
property at 473 Winchester Rd

473 Winchester Rd

WinchesterCT06098
property at 50 E Hill Rd

50 E Hill Rd

CantonCT06019
property at 213 Ledge Dr

213 Ledge Dr

TorringtonCT06790
property at 29 Benton St

29 Benton St

WinchesterCT06098
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690 Hopmeadow St
2 Bedroom Apartments

690 Hopmeadow St

690 Hopmeadow StSimsbury, CT 06070

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.

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 2,406 square feet priced from $3,500. 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 $3,583. Here is today’s list of the largest available 2 Bedroom units in Winsted:

Apartment ListingModel NameSquare FootagePriced From
The Grand RyefieldTownhome D2,406 Sq Ft$3,500
Highcroft ApartmentsVista1,415 Sq Ft$3,583
The Preserve at Great PondThe Farmington 31,415 Sq Ft$2,810
Mill CommonsThe Ensign1,410 Sq Ft$3,386
The Pointe at Dorset CrossingOak1,385 Sq Ft$2,875
Station 2802 Bedroom 2 Bathroom D ADA1,306 Sq Ft$2,766
Greenway Village2 Bedroom1,300 Sq Ft$2,700

Cheapest Available Winsted and Nearby 2 Bedroom Apartments

As of October 23, 2025 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 $2,606. 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 StB2$1,475
Mill at Still River2 BD Remodel WD$1,800
Avon Woods Apartments2 Bedroom - Classic$1,895
Avon PlaceRidgewood$2,000
Canal PlaceShadowbrook$2,225
Alexandria Manor2BD 1BA Remodel$2,255
King's Ridge (small quiet community)Two Bedroom 1.5 bath$2,325
The Oliver BloomfieldB1$2,401

Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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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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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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Pet Friendly Lifestyle

Ranked #

Among cities in Connecticut for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

Pet Friendly

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

Explore Winsted, CT Rentals by Map

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Getting Around Winsted, CT

Walk Score®

48 / 100

Car-Dependent

Most errands require a car

Bike Score®

24 / 100

Somewhat Bikeable

Minimal bike infrastructure

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 $2,606.

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

Today's apartment with the most square footage in Winsted is a 2,406 square feet unit starting from $3,500 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 1,229 sq ft.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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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.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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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.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.