6 Glenmere Ave, Unit 4
6 Glenmere Ave
FloridaNY10921
Cheap Homes for Rent in Chester, NY from $1,500 (13 Rentals)
Search the lowest-cost Homes available for rent right now in Chester.
3102 Whispering Hills Dr
ChesterNY10918
20 Peddler Hill Rd
MonroeNY10950
222 Lehigh Ave
ChesterNY10918
33 Schnabel Rd
ChesterNY10918
6 Glenmere Ave, Unit 1
6 Glenmere Ave
FloridaNY10921
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.
20 Lexington Hills Rd
HarrimanNY10926
5 Point O Pine
MonroeNY10950
649 Lakes Rd
MonroeNY10950
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$2,1002 Bedroom Apartments Available Sep 15
53 Main St, Unit 4
53 Main StChester, NY 10918
25 Gloria Trail
MonroeNY10950
11 Lexington Hills Rd
HarrimanNY10926
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.
82 High St, Unit 5
82 High St
ChesterNY10918
Showing Results 1-13, Page 1 of 1
Chester, NY Local Guide
Checkers by darronb 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 | $2,332 | $1,750 | $3,295 |
| Chester 3 Bedroom Homes for Rent | $3,247 | $2,600 | $4,200 |
| Chester 4 Bedroom Homes for Rent | $4,232 | $2,895 | $7,500 |
| Chester 5 Bedroom Homes for Rent | $4,200 | $4,200 | $4,200 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Chester, NY Local Guide
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Cheapest Available Chester Apartments for Rent
The cheapest available apartment rental in Chester, NY is a 1 Bed unit found at Monroe Commons in the Estates of Briarcliff neighborhood priced from $783. Devon Woods has the second lowest priced unit, which is a 1 Bed apartment currently listed from $914. Here is today’s list of the most affordable Chester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Monroe Commons | 1 Bed, 1 bath | 1BR,1BA | $783 |
| Devon Woods | 2nd Fl 1br | 1BR,1BA | $914 |
| Hearthstone Apartments | 1 Bed / 1 Bath - 60% | 1BR,1BA | $1,214 |
| Sutton Hill Apartments | Sutton Hill Type 3 | 1BR,1BA | $1,740 |
| Crestwood Apartments | 1-Bedroom | 1BR,1BA | $1,750 |
Best Value Apartments for Rent in Chester, NY
As of September 05, 2026 the best value apartment in the Chester area is the $2.12 price per square foot Westchester Model at Summit Terrace Luxury Apartments in the in the Brighton Green neighborhood starting from $2,500. The second greatest value Chester apartment is the 2x1 Model at Sherwood Forest Garden Apartments starting at $2,250 with a $2.07 price per square foot in the Middletown Goshen 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. |
|---|---|---|---|
| Summit Terrace Luxury Apartments | Westchester | 2BR,2BA | $2.12 |
| Sherwood Forest Garden Apartments | 2x1 | 2BR,1BA | $2.07 |
| Sterling Parc at Middletown | Glenmore | 1BR,1.5BA | $2.34 |
| Woodbury Gardens | Two Bedroom | 2BR,1BA | $2.28 |
| Imperial Gardens Apartment Homes | Two Bedroom 1.5 Bath-916 sqft | 2BR,1BA | $2.35 |
| Carriage Hill Apartments | 1BR/ 1BA Deluxe | 1BR,1BA | $2.27 |
| Hawkins Apartments | 1 Bed, 1 bath | 1BR,1BA | $2.26 |
| Devon Woods | 1st Fl 1br | 1BR,1BA | $1.47 |
| Hearthstone Apartments | 1 Bed / 1 Bath - 60% | 1BR,1BA | $2.02 |
| Monroe Commons | 1 Bed, 1 bath | 1BR,1BA | $1.38 |
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 Article
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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.
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See the most popular apartments and homes in Chester, NY
Frequently Asked Questions about Chester
What type of rentals are currently available in Chester?
There are currently 60 Apartments for Rent in Chester, NY with pricing that ranges from $515 to $15,802. There are also 47 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,500 to $7,500.
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 $1,500 to $7,500 with an average monthly rent of $3,020.
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.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.