Homes for Rent in Chester, NY (41 Rentals)

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property at 28 Academy Ave

$2,695

Total Monthly Price

Total Monthly Price

Base Rent
$2,695
Total Monthly Price
$2,695

3 Bedroom, 1 Bath Home for Rent

Available Now

28 Academy Ave, Unit 2

28 Academy Ave
ChesterNY10918
property at 2722 Whispering Hills Dr

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950
Total Monthly Price
$2,950

3 Bedroom, 3 Bath Condo for Rent

Available Now

2722 Whispering Hills Dr, Unit 542

2722 Whispering Hills Dr
ChesterNY10918

Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

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The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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property at 24 Cromwell Hill Rd

$1,750

Total Monthly Price

Total Monthly Price

Base Rent
$1,750
Total Monthly Price
$1,750

1 Bedroom, 1 Bath Home for Rent

Available Now

24 Cromwell Hill Rd

MonroeNY10950
Showing Results 1-41, Page 1 of 1

Chester, NY Local Guide

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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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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Quick 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.

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Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Chester, NY Rentals by Map

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See the most popular apartments and homes in Chester, NY

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Frequently Asked Questions about Chester

What type of rentals are currently available in Chester?

There are currently 61 Apartments for Rent in Chester, NY with pricing that ranges from $495 to $15,652. There are also 40 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chester ranging from $1,750 to $6,000.

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 $1,750 to $6,000 with an average monthly rent of $3,249.

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

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Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

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Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

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Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.