Apartments for Rent in Chester, CT (104 Rentals) Page 2 of 3

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property at 23 Main St

$1,550 - $1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900

Total Monthly Price
$1,900

1 Bedroom Rentals

Available Now

23 Main St

East HaddamCT06423
property at 10 Plains Rd

$2,250

Total Monthly Price

Total Monthly Price

Base Rent
$2,250

Total Monthly Price
$2,250

3 Bedroom, 1 Bath Home for Rent

Available Now

10 Plains Rd

East HaddamCT06469
property at 55 Dogwood Rd

$2,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,450

Total Monthly Price
$2,450

2 Bedroom, 1 Bath Home for Rent

Available Now

55 Dogwood Rd

East HaddamCT06469
property at 66 Haywardville Rd

$2,750

Total Monthly Price

Total Monthly Price

Base Rent
$2,750

Total Monthly Price
$2,750

3 Bedroom, 1.5 Bath Home for Rent

Available Now

66 Haywardville Rd

East HaddamCT06423
property at 620 Town St

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom, 2 Bath Home for Rent

Available Now

620 Town St

East HaddamCT06469
property at 740 Little City Rd

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 2 Bath Home for Rent

Available Now

740 Little City Rd

HaddamCT06441
property at 117 Church Hill Rd

$3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 2 Bath Home for Rent

Available Now

117 Church Hill Rd

HaddamCT06438
property at 114 Lakeside Dr

$3,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 1 Bath Home for Rent

Available Now

114 Lakeside Dr

East HaddamCT06423
property at 255 Rte 80

$1,600

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,600

Total Monthly Price
$1,600

1 Bedroom, 1 Bath Home for Rent

Available Now

255 Rte 80

KillingworthCT06419
property at 8 Jacob Ln

$9,950

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$9,950

Total Monthly Price
$9,950

5 Bedroom, 3 Bath Home for Rent

Available Now

8 Jacob Ln

KillingworthCT06419
property at 33 Main St

$1,750

Total Monthly Price

Total Monthly Price

Base Rent
$1,750

Total Monthly Price
$1,750

1 Bedroom, 1 Bath Home for Rent

Available Now

33 Main St

EssexCT06442
property at 25 Park Rd

$1,795

Total Monthly Price

Total Monthly Price

Base Rent
$1,795

Total Monthly Price
$1,795

1 Bedroom, 1 Bath Home for Rent

Available Now

25 Park Rd

EssexCT06442
property at 70 Pond Meadow Rd

$1,800

Total Monthly Price

Total Monthly Price

Base Rent
$1,800

Total Monthly Price
$1,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

70 Pond Meadow Rd

EssexCT06442
property at 190 Westbrook Rd

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 2 Bath Condo for Rent

Available Now

190 Westbrook Rd

EssexCT06426
property at 27 S Main St

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 2.5 Bath Condo for Rent

Available Now

27 S Main St

EssexCT06426
property at 33 Prospect St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 2 Bath Home for Rent

Available Now

33 Prospect St

EssexCT06426
property at 1742 Boston Post Rd

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900

Total Monthly Price
$1,900

2 Bedroom, 1 Bath Condo for Rent

Available Now

1742 Boston Post Rd

WestbrookCT06498
property at 9 Essex Rd

$2,300

Total Monthly Price

Total Monthly Price

Base Rent
$2,300

Total Monthly Price
$2,300

3 Bedroom, 1 Bath Home for Rent

Available Now

9 Essex Rd

WestbrookCT06498
property at 92 Grove Beach Rd S

$2,700

Total Monthly Price

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

3 Bedroom, 1.5 Bath Home for Rent

Available Now

92 Grove Beach Rd S

WestbrookCT06498
property at 6 Leeway Dr

$3,999

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,999

Total Monthly Price
$3,999

3 Bedroom, 3 Bath Home for Rent

Available Now

6 Leeway Dr

WestbrookCT06498
property at 173 Captains Dr

$4,575

Total Monthly Price

Total Monthly Price

Base Rent
$4,575

Total Monthly Price
$4,575

4 Bedroom, 3 Bath Home for Rent

Available Now

173 Captains Dr

WestbrookCT06498
property at 293 Hamburg Rd

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom, 1 Bath Home for Rent

Available Now

293 Hamburg Rd

LymeCT06371
property at 126 Beaver Brook Rd

$2,850

Total Monthly Price

Total Monthly Price

Base Rent
$2,850

Total Monthly Price
$2,850

1 Bedroom, 1 Bath Home for Rent

Available Now

property at 150 Ferry Rd

$5,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

3 Bedroom, 3.5 Bath Home for Rent

Available Now

150 Ferry Rd

LymeCT06371
property at 119 Kelseytown Rd

$1,250

Total Monthly Price

Total Monthly Price

Base Rent
$1,250

Total Monthly Price
$1,250

1 Bedroom, 1 Bath Home for Rent

Available Now

119 Kelseytown Rd

ClintonCT06413
property at 144 E Main St

$1,995

Total Monthly Price

Total Monthly Price

Base Rent
$1,995

Total Monthly Price
$1,995

2 Bedroom, 1 Bath Townhome for Rent

Available Jan 1, 2026

144 E Main St

ClintonCT06413
property at 248 Killingworth Turnpike

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Home for Rent

Available Now

property at 69 Waterside Ln

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

1 Bedroom, 1 Bath Home for Rent

Available Now

69 Waterside Ln

ClintonCT06413
property at 5 Beaver Dam Trail

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

4 Bedroom, 2.5 Bath Home for Rent

Available Now

5 Beaver Dam Trail

Old SaybrookCT06475
property at 101 Legend Hill Rd

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 2 Bath Condo for Rent

Available Now

101 Legend Hill Rd

MadisonCT06443
property at 156 Concord Dr

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 2 Bath Home for Rent

Available Now

156 Concord Dr

MadisonCT06443
property at 1281 Durham Rd

$3,750

Total Monthly Price

Total Monthly Price

Base Rent
$3,750

Total Monthly Price
$3,750

4 Bedroom, 2 Bath Home for Rent

Available Now

1281 Durham Rd

MadisonCT06443
property at 138 School House Rd

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

2 Bedroom, 3 Bath Home for Rent

Available Now

138 School House Rd

Old SaybrookCT06475
property at 101 Cow Hill Rd

$3,995

Total Monthly Price

Total Monthly Price

Base Rent
$3,995

Total Monthly Price
$3,995

4 Bedroom, 2.5 Bath Home for Rent

Available Now

101 Cow Hill Rd

ClintonCT06413
property at 28 Beach Rd W

$4,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

2 Bedroom, 2 Bath Home for Rent

Available Now

28 Beach Rd W

Old SaybrookCT06475
property at 7 Saye St

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

3 Bedroom, 2 Bath Home for Rent

Available Now

7 Saye St

Old SaybrookCT06475
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59-65 Maple St
1 Bedroom Apartments

59-65 Maple St

59-65 Maple StChester, CT 06412
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132 W Main St
1 Bedroom Apartments

132 W Main St

132 W Main StChester, CT 06412
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170 Main St
7 Bedroom Apartments

170 Main St

170 Main StDeep River, CT 06417
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113 Union St
1 to 2 Bedroom Apartments

113 Union St

113 Union StDeep River, CT 06417
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214 Main St
3 Bedroom Apartments

214 Main St

214 Main StDeep River, CT 06417
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93 Main St
1 to 2 Bedroom Apartments

93 Main St

93 Main StDeep River, CT 06417
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26 Sunset Ter
1 to 2 Bedroom Apartments

26 Sunset Ter

26 Sunset TerEssex, CT 06426

Getting Around Chester, CT

Walk Score®

29 / 100

Car-Dependent

Most errands require a car

Bike Score®

17 / 100

Somewhat Bikeable

Minimal bike infrastructure

Frequently Asked Questions about Chester

How much are Studio apartments in Chester?

There are currently 14 Studio Apartments in Chester with rent ranges from $975 to $2,071 with an average price of $1,604.

What is the current price range for One Bedroom Chester Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Chester ranges from $710 to $3,440 with an average monthly rent of $2,003.

What does renting a Two Bedroom Apartment in Chester cost?

The monthly rent prices of Two Bedroom Apartments currently available in Chester range from $864 to $4,301. Today's average rental price for Two Bedrooms here is $2,495.

How expensive are Chester Three Bedroom Apartments?

There are currently 17 Three Bedroom Apartments listings available in Chester on ApartmentHomeLiving.com. The pricing ranges from $1,700 to $3,895 - averaging $3,006 for the location.

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

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

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.