
Cheap Apartments for Rent in Chester, CT from $500 (61 Rentals)
Search the lowest-cost Apartments available for rent right now in Chester.


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9 Maple St, Unit E

86 Spring St

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11 Maple St, Unit B

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Wharfside Commons

Amston Village - Active 55+

Burgundy Apartments

Woodrow Wilson Apartments

Stoneycrest Tower

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Encore
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Willowcrest

Middletown at Main

Stillman School Apartments

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Country Place

StoneGate Apartments

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Rocky Neck Village

On Ward Apartments

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Deerfield Village

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Southwind Apartments

The Meriden
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.

Fernwood Apartments

The Wilcox

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Middletown Brooke Apartments

Theresa A. Rook Retirement Community

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Sagamore Hills

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Meadoway Gardens

Midd-Town Apartments

Rose Gardens Apartments

Woodbury Apartments

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Brainerd Place
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

70 Pond Meadow Rd

Bay Point Apartments

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Colchester Estates

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The Edgewater

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The Sound at Gateway Commons

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Haddam Village Commons

23 Main St

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Marshfield Apartments

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The Arlo

Knoll Crest Apartments
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

Northwoods East

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Town Place

562 Main St

The Village at 82 Main

21 Plains Rd

1823 Boston Post Rd

Birchwood Apartments

26 Sunset Ter

584 Main St

South Green Apartments
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
Chester, CT Local Guide

How much does it cost to rent an apartment in Chester?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Chester Studio Apartments | $1,640 | $975 | $1,995 |
| Chester 1 Bedroom Apartments | $1,993 | $710 | $3,818 |
| Chester 2 Bedroom Apartments | $2,497 | $500 | $4,619 |
| Chester 3 Bedroom Apartments | $2,993 | $1,491 | $4,276 |
Browse Top Apartments in Chester
See all Apartments in ChesterExplore Chester
Chester, CT Local Guide
- Chester Neighborhoods
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Cheapest Neighborhoods for Apartments in Chester, CT
Pricing Updated: 07/26/2026Current 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 | $2,000 | $1,100 | 3 |
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 |
| Stoneycrest Tower | Efficiency | Studio,1BA | $1,133 |
| Encore | Encore Apartments | Studio,1BA | $1,300 |
| The Village at 82 Main | 1 Beds, 1 Baths | 1BR,1BA | $1,400 |
| Middletown at Main | 594-studio | Studio,1BA | $1,400 |
| Willowcrest | One Bedroom Flat | 1BR,1BA | $1,400 |
| Woodrow Wilson Apartments | 1 Bedroom | 1BR,1BA | $1,400 |
Best Value Apartments for Rent in Chester, CT and Nearby
As of July 26, 2026 the best value apartment in the Chester area is the $1.83 price per square foot C1E Model at Northwoods East in the in the Cromwell Middletown neighborhood starting from $2,849. 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 | $1.83 |
| 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 |
| 9 Maple St, Unit E | 9 Maple St | 1BR,1BA | $1.65 |
| Woodrow Wilson Apartments | 1 Bedroom | 1BR,1BA | $1.75 |
| 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.
Read ArticleReal 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.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Chester, CT Rentals by Map
See the most popular apartments and homes in Chester, CT
Frequently Asked Questions about Cheap Chester Apartments
What is the Cheapest Studio apartment in Chester?
Currently the most affordable Cheap Studio Apartment in Chester is at Burgundy Apartments listed at $975.
How much is rent for a Cheap One Bedroom Chester Apartment?
The lowest price for a Cheap One Bedroom Chester Apartment is $1,400 at Woodrow Wilson Apartments.
What is the lowest price for a Cheap Two Bedroom Chester Apartment for rent?
Today's best deal for a Cheap Two Bedroom Apartment in Chester is starting from $500 at Wharfside Commons.
What is the most affordable Chester Three Bedroom Apartment?
The best deal on a cheap Chester Three Bedroom Apartment rental is at Rocky Neck Village and starts from $1,491.
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.