Note: Properties with the Total Monthly Price badge include all required fees. Tap the badge for more details.
-

Bedrooms

Bathrooms

Deals & Discount Filters
All Filters

Deals & Discounts

Price Range

–

Beds & Baths

Beds

Baths

Home Type

Pet Policy

Interior & Community Amenities

Speciality Housing

Keyword Search

Apartments under $2,000 for Rent in Chester, CT

8 Rentals
.
  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 - 70 Pond Meadow Rd
    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
  4. Building Photo - 52 Essex St
    2 BEDS, 1 BATH
    $1,695
    Total Monthly Price Total Monthly Price New
    Base Rent$1,695
    Required Monthly FeesNone
    Total Monthly Price$1,695

    52 Essex St

    52 Essex St, Deep River, CT 06417
  5. 1 BED, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    26 Sunset Terrace Unit C15

    26 Sunset Terrace, Essex, CT 06426

Can't find what you are looking for?

Clear All Filters

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

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.

Education

Private University
Private University
Private University
Public University
Private University
GreatSchools Rating
Chester Elementary School

Public Elementary School

Public
Grades K-5
Students

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

tooltips

I would like to...
0 out of 400 characters
By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to... By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to Apartmentfinder.com’s Privacy Statement and Terms of Service. Consent is not a condition for services. Message and data rates may apply. Read More Read Less

Submitting Request

Thank You

Your email has been sent.

Learn about our ratings.