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Apartments for Rent in Winchester, CT

Average rent

$975
increased by6%

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279 North Main Street #7 - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

Air conditioning | On-site laundry | Hardwood floor

1 bed

1 bath

$875

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

Available Apr 8

Cozy Modern Apartment with Unique Floor Plan

This charming 1-bedroom, 1-bath apartment offers a bright and efficient layout, maximizing space while providing comfort. Enjoy the fresh ambiance with hardwood floors and ample closet space. Situated in a well-maintained 8-unit building, on-site laundry makes life easy. Conveniently located near shopping, dining, and highways, it’s perfect for professionals seeking a hassle-free lifestyle in a welcoming community.

10 Bridge Street Bld 2 - Photo 1 of 1

3d ago

8.6

Very good

10 Bridge Street Bld 2

10 Bridge St Ste 2, Winsted, CT 06098

Air conditioning

Studio

-1 baths

$500–$600

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

Creative Office Space with All-Inclusive Perks

10 Bridge Street Bld 2 offers a charming office space perfect for an art studio or workspace at Mad River Lofts in Winsted, CT. Enjoy free WiFi, all utilities included, and 24-hour building access, complete with a common room kitchenette. Embrace a flexible, convenient, and inspiring environment for your professional needs.

58 Main Street - Photo 1 of 1

3d ago

8.4

Very good

58 Main Street

58/60 Main Street, Winsted, CT 06098

1 bed

1 bath

$1,075

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

Renovated Downtown Living with Convenience & Comfort

Recently renovated, this pet-friendly one-bedroom apartment is perfect for downtown living in Winsted. With heat and hot water included, it features beautiful hardwood floors. Residents enjoy easy access to Route 8, Route 44, and within walking distance of shops, restaurants, parks, and college. A no-cost application is required prior to scheduling viewings. Embrace a vibrant lifestyle in a community brimming with amenities!

450 Main Street - Photo 1 of 1

4d ago

7.7

Very good

450 Main Street

450 Main St, Winsted, CT 06098

On-site laundry

1 bed

1 bath

$950

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

Prime Commercial Space with High Visibility

450 Main Street offers a spacious 650 sq ft commercial unit in the heart of Winchester, perfect for a boutique or professional office. This highly visible location features large front windows and is surrounded by vibrant shopping, dining, and community events. Boasting excellent foot traffic and affordable rent at $650 per month, it's an unbeatable opportunity to establish a business in a thriving downtown district. Don’t let this rare chance slip away!

426 Main Street - Photo 1 of 1

5d+ ago

8.3

Very good

426 Main Street

420 Main St, Winsted, CT 06098

2 beds

1 bath

$1,375

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

Cozy Downtown Walk-Up with Heat Included

Located in downtown Winsted, this 3rd-floor walk-up offers a flexible 2–3 bedroom layout with heat included, a covered back porch for outdoor relaxation, and plenty of storage. Residents benefit from off-street parking and easy access to Route 44 and Route 8, all in a well-maintained building with a one-year lease term.

100 Lake Street - Photo 1 of 1

5d+ ago

8.3

Very good

100 Lake Street

100 LakeStreet, Winsted, CT 06098

1 bed

1 bath

$975

The price shown reflects a 12-month lease and includes base rent plus all required monthly fees provided by the property.

Apartment for rent

Cozy Convenience Steps from Highland Lake

Residents of 100 Lake Street enjoy a cozy third-floor one-bedroom apartment with an extra room for flexible living. This pet-friendly home features gas heating and a gas stove, with on-site laundry facilities available. A short walk leads to beautiful Highland Lake, and easy access to Route 8 and Route 44 makes commuting a breeze. Off-street parking is available, ensuring convenience in a welcoming community. Perfect for those wanting comfort and connection to nature!

100 LakeStreet - 11 #11 - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

100 Lake Street - 11

100 LakeStreet - 11 #11, Winsted, CT 06098

1 bed

1 bath

$975

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available May 1

Bright and Cozy Apartment near Highland Lake

This charming 1-bedroom, 1-bath apartment features recently updated kitchen and bathroom facilities, just minutes from Highland Lake. Enjoy the convenience of on-site laundry and off-street parking for one car. Pet-friendly accommodations are available with a one-time pet fee, making it an ideal retreat for residents and their furry friends. The owner handles snow removal and trash services, ensuring a hassle-free living experience.

22 Upson Ave - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

22 Upson Ave, Winsted, CT 06098

Hardwood floor | High ceilings

2 beds

1 bath

$1,250

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Charming First-Floor Apartment with Modern Flair

Embrace classic charm in this spacious first-floor apartment featuring 2 bedrooms and 1 bath within 1,199 sq ft. Gleaming hardwood floors and high ceilings enhance the inviting atmosphere. An updated kitchen complements the fresh paint and beautiful woodwork throughout. Ideally situated near downtown, enjoy convenient access to shopping, dining, and commuting routes, making this the perfect blend of comfort and convenience.

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277 N Main St #3 - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

APARTMENT - Winchester, CT

277 N Main St #3, Winsted, CT 06098

Air conditioning | On-site laundry | Assigned parking

1 bed

1 bath

$900

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Bright and Affordable Third-Floor Apartment

This freshly painted 1-bed, 1-bath apartment offers a bright, open living space with an efficient layout. Enjoy an in-wall A/C unit, ample cabinet storage, and a clean bath. Convenient on-site coin laundry and two off-street parking spots make life easy. Perfectly situated near shops and dining, this comfortable and affordable rental is all about convenient living!

440 Main St #B - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

APARTMENT - Winchester, CT

440 Main St #B, Winsted, CT 06098

2 beds

1 bath

$1,200

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Convenient Second-Floor Apartment Near Amenities

This cozy two-bedroom apartment features a smart layout with four rooms, perfect for comfortable living. Located on the second floor, it offers easy access to local stores, restaurants, and medical facilities, making it ideal for those seeking convenience in town. Enjoy a compact yet functional space, perfect for your lifestyle needs.

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Find rentals with popular amenities

High Ceilings

Air Conditioning

On-Site Laundry

Hardwood Floor

101 Whiting St #H - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

101 Whiting St #H, Winsted, CT 06098

On-site laundry | High ceilings

1 bed

0 baths

$1,500

The price shown reflects a 12-month lease. Fees may apply.

Apartment for rent

Available Apr 3

Charming Mill Living with Scenic River Views

Experience the unique charm of this turn-of-the-century apartment featuring stunning exposed wood beams, 10-foot ceilings, and oversized industrial windows. This bright unit overlooks the serene Still River, offering a blend of comfort and nature right at your doorstep. Community amenities include convenient same-floor laundry and private parking. Enjoy a welcoming, smoke-free environment in one of the best spots in Winsted, CT.

Showing 1 - 11 of 11 results

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Home > Apartments in Winchester
Updated: April 28, 2026

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Apartment rentals New Haven, CT FAQ

What is the average size of an apartment in New Haven, CT?

The average size of a 1 bedroom apartment rental in New Haven is 239 square feet. The average size of a 2 bedroom apartment rental in New Haven is 1467 square feet. The average size of a 3 bedroom apartment rental in New Haven is 678 square feet.

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🔑Available apartment rentals22
💰Best rent deal10 Bridge St Ste 2
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos