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Apartments for Rent in Winchester, CT

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279 North Main Street #8 - Photo 1 of 1

4d ago

Apartment for rent in Winchester

279 North Main Street #8, Winchester, CT 06098

Air conditioning | On-site laundry | Balcony

1 bed

1 bath

$800

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

Apartment for rent

Available Jul 27

398 Main St #11 - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

5 Elm Street - 11

398 Main St #11, Winsted, CT 06098

On-site laundry | Elevator

2 beds

1 bath

$1,400

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

Apartment for rent

Available Aug 1

31 Woodruff Ave #1 - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

APARTMENT - Winchester, CT

31 Woodruff Ave #1, Winsted, CT 06098

In-unit laundry | Garage parking | Hardwood floor

1 bed

1 bath

$1,200

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

Apartment for rent

L09 Nanni Dr - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

L09 Nanni Dr, Winsted, CT 06098

2 beds

1 bath

$1,495

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

Apartment for rent

335 Taylor Brook Rd #NA - Photo 1 of 1

5d+ ago

House for rent in Winsted

Refurbished 3 Bedroom 1 Bathroom House In Winchester With Great Amenities and Beatiful Location

335 Taylor Brook Rd #NA, Winsted, CT 06098

Assigned parking | Hardwood floor | Deck

3 beds

1 bath

$1,800

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

House for rent

Available Jul 22

111 Rockwell St ##A - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

111 Rockwell St ##A, Winsted, CT 06098

In-unit laundry | Air conditioning | Assigned parking

2 beds

1 bath

$1,225

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

Apartment for rent

43 Wallens St #1st - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

MULTI_FAMILY - Winchester, CT

43 Wallens St #1st, Winsted, CT 06098

On-site laundry

1 bed

1 bath

$1,195

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

Apartment for rent

267 Rockwell St #1stFL - Photo 1 of 1

5d+ ago

Apartment for rent in Winsted

MULTI_FAMILY - Winchester, CT

267 Rockwell St #1stFL, Winsted, CT 06098

On-site laundry

1 bed

1 bath

$1,195

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

Apartment for rent

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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

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

$1,000

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

Apartment for rent

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Balcony

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Storage

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27 Dilliston Rd - Photo 1 of 1

5d+ ago

House for rent in New Hartford

SINGLE_FAMILY - New Hartford, CT

27 Dilliston Rd, New Hartford, CT 06057

In-unit laundry | Furnished

2 beds

1 bath

$1,190

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

House for rent

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

15 Thibault Ave #15 - Photo 1 of 1

4d ago

Apartment for rent in Winsted

15-19 Thibault Ave - 15

15 Thibault Ave #15, Winsted, CT 06098

3 beds

1 bath

$1,250

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

Apartment for rent

Available Jul 24

58 Main Street - Photo 1 of 1

4d ago

8.1

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

15 Mountain View Terrace - Photo 1 of 1

5d+ ago

8.3

Very good

15 Mountain View Terrace

15 Mountain View Ter, Winsted, CT 06098

Dishwasher

2 beds

1 bath

$1,550

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

Apartment for rent

Gilbert Clock Apartments - Photo 1 of 1

4d ago

8.3

Very good

Gilbert Clock Apartments

13 Wallens St, Winsted, CT 06098

On-site laundry | Free parking

Studio–2 beds

1 bath

$1,150–$1,250

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

Apartment for rent

Find sweet deals near Winchester

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$900

Winsted

$1,000

Winsted

$1,190

New Hartford

$1,250

Winsted

22h ago

8.8

Very good

5 Elm Street

5 Elm St, Winsted, CT 06098

On-site laundry | Elevator

2 beds

1 bath

$1,400

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

Apartment for rent

10 Bridge Street Bld 2 - Photo 1 of 1

4d 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

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Listings within 10 miles
34 South Rd - Photo 1 of 1

5d+ ago

Apartment for rent in New Hartford

APARTMENT - New Hartford, CT

34 South Rd, New Hartford, CT 06057

2 beds

1.5 baths

$2,400

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

Apartment for rent

433 Migeon Ave #433 - Photo 1 of 1

4d ago

Apartment for rent in Torrington

MULTI_FAMILY - Torrington, CT

433 Migeon Ave #433, Torrington, CT 06790

In-unit laundry | Garage parking | Storage

2 beds

1 bath

$1,450

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

Apartment for rent

Listings within 20 miles
11 Clover Ct #NA - Photo 1 of 1

1d ago

House for rent in Avon

11 Clover Ct #NA, Avon, CT 06001

In-unit laundry | Air conditioning | Garage parking

3 beds

2 baths

$2,850

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

House for rent

Available Aug 8

13 Meadowbrook Ln - Photo 1 of 1

4d ago

House for rent in Avon

Charming 3 Bed, 1.5 Bath Single Family Home in a cul-de-sac in Avon, CT - $3000/mo

13 Meadowbrook Ln, Avon, CT 06001

In-unit laundry | Garage parking | On-site laundry

3 beds

2 baths

$3,000

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

House for rent

Available Aug 8

604 Huckleberry Hill Rd - Photo 1 of 1

4d ago

House for rent in Avon

604 Huckleberry Hill Rd, Avon, CT 06001

In-unit laundry | Garage parking | Storage

2 beds

1 bath

$2,140

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

House for rent

Available Sep 5

Average rent

The average rent in Winchester, as of July 2026, is flat compared to last month and unchanged year-over-year.
$1,500

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Showing 1 - 25 of 25 results
Home > Apartments in Winchester
Updated: July 29, 2026

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279 N Main St
58 Main St
Oakdale Apartments
River Walk

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Learn more about renting in Winchester, CT

Local insights: What it's like to live in Winchester, CT

Daily life in Winchester, CT has a relaxed vibe that residents appreciate, with plenty of outdoor spaces and local parks for leisurely strolls or family outings. The sense of safety is often highlighted, making it a suitable choice for families. People enjoy the local amenities, especially the small-town shops and eateries. However, some residents express frustration over limited public transportation and the availability of nightlife options, which can make the town feel a bit quiet after dark. Overall, it’s seen as a decent place for those looking for a slower pace and access to nature.

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.

Apartment rentals Winchester, CT FAQ

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

The average size of a 1 bedroom apartment rental in Winchester is 313 square feet. The average size of a 2 bedroom apartment rental in Winchester is 1160 square feet. The average size of a 3 bedroom apartment rental in Winchester is 2066 square feet.

Can I afford an apartment for rent in Winchester, CT?

To help you better understand how much rent you can afford, check out Zumper's rent calculator. Our rent calculator can help you learn more about Winchester average rent prices.

Looking for apartments in Winchester, CT near you?

🔑Available apartment rentals25
💰Best rent deal10 Bridge St Ste 2
✨Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos