21 Plains Rd
East HaddamCT06469
Cheap Homes for Rent in Chester, CT from $1,400 (6 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
1823 Boston Post Rd
WestbrookCT06498
89 Grove Beach Rd S
WestbrookCT06498
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
22 Menunketesuck Rd
WestbrookCT06498
86 Spring St
ChesterCT06412
7 Stephens Ct
ClintonCT06413
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
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Chester, CT Local Guide
Flags over connecticut by Lisa Jacobs is licensed under CC BY 2.0
How much does it cost to rent a home in Chester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chester 2 Bedroom Homes for Rent | $2,750 | $1,800 | $4,500 |
| Chester 3 Bedroom Homes for Rent | $4,185 | $1,800 | $10,000+ |
| Chester 4 Bedroom Homes for Rent | $4,164 | $2,100 | $6,000 |
| Chester 5 Bedroom Homes for Rent | $3,200 | $3,200 | $3,200 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Chester, CT Local Guide
- Chester Neighborhoods
- Nearby Cities
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Cheapest Neighborhoods for Apartments in Chester, CT
Pricing Updated: 07/29/2026Current apartment rentals in the Chester, CT area range in price from to with an overall median price of . Here is today’s list neighborhoods with the lowest median pricing for Chester Apartments for rent:
| Neighborhood | Median Price | Min Price | Available Units |
|---|---|---|---|
| Hadlyme | $10,000 | $3,200 | 2 |
Cheapest Available Chester Apartments for Rent and Nearby
The cheapest available apartment rental in Chester, CT is a 2 Beds unit found at Wharfside Commons in the East Hampton Portland neighborhood priced from $500. Burgundy Apartments in the Cromwell Middletown neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $975. Here is today’s list of the most affordable Chester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Wharfside Commons | 2Bed 2 Bath | 2BR,2BA | $500 |
| Burgundy Apartments | Studio | Studio,1BA | $975 |
| Woodrow Wilson Apartments | studio | Studio,1BA | $1,100 |
Best Value Apartments for Rent in Chester, CT and Nearby
As of July 29, 2026 the best value apartment in the Chester area is the $1.84 price per square foot C1E Model at Northwoods East in the in the Cromwell Middletown neighborhood starting from $2,870. The second greatest value Chester apartment is the 3 bedroom - MKT Model at Rocky Neck Village starting at $2,650 with a $1.88 price per square foot in the South Lyme neighborhood. Here is today’s list of the best values for Chester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Northwoods East | C1E | 3BR,2BA | $1.84 |
| Rocky Neck Village | 3 bedroom - MKT | 3BR,2BA | $1.88 |
| StoneGate Apartments | 2 Bed 1 Bath | 2BR,2BA | $1.54 |
| Colchester Estates | 410 | 2BR,1BA | $1.80 |
| Wharfside Commons | 2Bed 2 Bath | 2BR,2BA | $0.52 |
| Rose Gardens Apartments | Two Bedroom Townhouse | 2BR,1.5BA | $1.89 |
| Stillman School Apartments | 1 bedroom | 1BR,1BA | $1.47 |
| 9 Maple St, Unit E | 9 Maple St | 1BR,1BA | $1.65 |
| Willowcrest | One Bedroom Flat | 1BR,1BA | $1.85 |
| 3 Maple St, Unit 3-1 | 3 Maple St | 1BR,1BA | $1.83 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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Frequently Asked Questions about Chester
What type of rentals are currently available in Chester?
There are currently 70 Apartments for Rent in Chester, CT with pricing that ranges from $500 to $4,771. There are also 35 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,400 to $10,000.
What is the current price range for Rental Homes in Chester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Chester ranges from $1,400 to $10,000 with an average monthly rent of $3,048.
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
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.