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Showing all results in Chester, CT.

  1. Interior Photo - Blueway Commons
    1 BED
    $2,016+
    2 BEDS
    $2,697+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,899 - $2,676
    Required Monthly Fees$117
    Utilities & EssentialsVaries
    Total Monthly Price$2,016 - $2,793

    Blueway Commons

    3 Brookes Ct, Haddam, CT 06438
    (860) 775-7409
  2. Building Photo - 70 Pond Meadow Rd
    2 BEDS
    $1,800
    Plus Fees - 12 Month Lease

    70 Pond Meadow Rd

    70 Pond Meadow Rd, Ivoryton, CT 06442
  3. Building Photo - 2 Orchard Rd
    1 BED, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495
    - 12 Month Lease

    2 Orchard Rd Unit 2nd floor

    2 Orchard Rd, East Haddam, CT 06423
  4. Building Photo - 6 Orchard Rd
    1 BED, 1 BATH
    $1,495
    Total Monthly Price Total Monthly Price New
    Base Rent$1,495
    Required Monthly FeesNone
    Total Monthly Price$1,495
    - 12 Month Lease

    6 Orchard Rd Unit 2

    6 Orchard Rd, East Haddam, CT 06423
  5. 2 BEDS, 1 BATH
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000
    - 12 Month Lease

    100 Main St Unit Carriage House

    100 Main St, Ivoryton, CT 06442
  6. 4 BEDS, 1 BATH
    $2,400
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400
    Required Monthly FeesNone
    Total Monthly Price$2,400
    - 12 Month Lease

    53 Main St Unit A

    53 Main St, Deep River, CT 06417
  7. Building Photo - 23 Main St
    1 BED, 1 BATH
    $1,550
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550
    Required Monthly FeesNone
    Total Monthly Price$1,550

    23 Main St Unit 2 - The Burton Suite

    23 Main St, East Haddam, CT 06423
  8. Building Photo - 33 Prospect St
    2 BEDS, 2 BATHS
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500

    33 Prospect St

    33 Prospect St, Essex, CT 06426
  9. 2 BEDS, 2.5 BATHS
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500

    55 Liberty St

    55 Liberty St, Chester, CT 06412
  10. 2 BEDS, 1 BATH
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800

    70 Pond Meadow Rd

    70 Pond Meadow Rd, Essex, CT 06442
  11. 2 BEDS, 1 BATH
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100

    159 Main St Unit E

    159 Main St, Chester, CT 06412
  12. 1 BED, 1 BATH
    $1,250
    Total Monthly Price Total Monthly Price New
    Base Rent$1,250
    Required Monthly FeesNone
    Total Monthly Price$1,250

    119 Kelseytown Rd

    119 Kelseytown Rd, Clinton, CT 06413
  13. 1 BED, 1 BATH
    $1,795
    Total Monthly Price Total Monthly Price New
    Base Rent$1,795
    Required Monthly FeesNone
    Total Monthly Price$1,795

    25 Park Rd

    25 Park Rd, Essex, CT 06442
  14. 5 BEDS, 3 BATHS
    $9,950
    Total Monthly Price Total Monthly Price New
    Base Rent$9,950
    Required Monthly FeesNone
    Total Monthly Price$9,950

    8 Jacob Ln

    8 Jacob Ln, Killingworth, CT 06419
  15. 3 BEDS, 1 BATH
    $2,200
    Total Monthly Price Total Monthly Price New
    Base Rent$2,200
    Required Monthly FeesNone
    Total Monthly Price$2,200

    15 Laurel St

    15 Laurel St, Chester, CT 06412
  16. 1 BED, 1 BATH
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    33 Main St

    33 Main St, Essex, CT 06442
  17. 1 BED, 1 BATH
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    23 Main St

    23 Main St, East Haddam, CT 06423
  18. 3 BEDS, 2 BATHS
    $3,300
    Total Monthly Price Total Monthly Price New
    Base Rent$3,300
    Required Monthly FeesNone
    Total Monthly Price$3,300

    117 Church Hill Rd

    117 Church Hill Rd, Haddam, CT 06438
  19. 1 BED, 1 BATH
    $1,600
    Total Monthly Price Total Monthly Price New
    Base Rent$1,600
    Required Monthly FeesNone
    Total Monthly Price$1,600

    255 Rte 80

    255 Rte 80, Killingworth, CT 06419
  20. Building Photo - 190 Westbrook Rd
    2 BEDS, 2 BATHS
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800

    190 Westbrook Rd Unit Apt2A

    190 Westbrook Rd, Essex, CT 06426

Chester at a Glance

Average Rent

N/A
(All bedrooms and property types)
6

School Rating

out of 10 Rating
Learn more about
Schools in Chester
0

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Chester
17

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Chester

Chester, CT Apartments for Rent

Located along the Connecticut River, Chester combines New England charm with small-town living. The downtown area features local shops, art galleries, and restaurants in well-preserved historic buildings. Founded in 1836, Chester maintains its historic character while offering contemporary conveniences and easy access to Connecticut's larger cities.

Chester's location in Middlesex County connects residents to recreational opportunities along the Connecticut River and nearby state parks. Covering approximately 16 square miles with about 3,700 residents, the town fosters a community-centered atmosphere. The location near Route 9 and Interstate 95 puts Hartford, New Haven, and the Connecticut shoreline within 30-45 minutes by car. Local traditions like the Chester-Hadlyme Ferry service (the second-oldest continuously operating ferry in Connecticut) and the annual Chester Fair add to the town's appeal while maintaining convenient access to urban areas.

Getting Around Chester

Transportation

29

Car-Dependent

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
17

Somewhat Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
0

Minimal Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Score

Education

Private University
Private University
Private University
Private University
GreatSchools Rating

Public Elementary School

Public
Grades K-6
222 Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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