2 Bedroom Apartments for Rent in Winsted, CT (60 Rentals)

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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
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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

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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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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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.

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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. 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 $2,995. 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
The Preserve at Great PondFarmington1,415 Sq Ft$2,995
The Pointe at Dorset CrossingSycamore1,403 Sq Ft$2,928
Station 2802 Bedroom 2 Bathroom D ADA1,306 Sq Ft$2,700
Greenway Village2 Bedroom1,300 Sq Ft$2,700
Avon PlaceLaurelside1,273 Sq Ft$2,000
Highcroft ApartmentsUpland1,240 Sq Ft$3,285
The Ridge at Talcott MountainB11,152 Sq Ft$2,200
King's Ridge (small quiet community)Two Bedroom 1.5 bath1,115 Sq Ft$2,325

Cheapest Available Winsted and Nearby 2 Bedroom Apartments

As of July 24, 2025 the lowest priced 2 Bedroom apartment unit in Winsted, CT is the Two Bedroom Model starting from $1,250 at Gilbert Clock Apartments . The second most affordable Winsted 2 Bedroom is the Two Bedroom Model at Winthrop Court Apartments starting at $1,250 . The average price for all 2 Bedroom apartments in Winsted is currently $2,657. Here is today’s list of the cheapest available 2 Bedroom options in Winsted:

Apartment ListingModel NamePriced From
Gilbert Clock ApartmentsTwo Bedroom$1,250
Winthrop Court ApartmentsTwo Bedroom$1,250
Litchfield Heights2 bedroom Town House$1,450
22 High StB2$1,575
Mill at Still River2 BD Remodel WD$1,800
Avon PlaceRidgewood$2,000
29 Water St ApartmentsTwo Bedroom$2,000
The Ridge at Talcott MountainB1$2,200
King's Ridge (small quiet community)Two Bedroom$2,250
Alexandria Manor2BD 1BA Remodel$2,255

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Pet Friendly Lifestyle

Ranked #

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

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Best Local Schools in
Winsted, CT

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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

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

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 $1,250.

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

The average rent for a 2 Bedroom Apartment in Winsted is $2,657.

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 1,289 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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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.

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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.