3 Bedroom Homes for Rent in Chestertown, NY (25 Rentals)

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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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property at 45 Bakery Ln

45 Bakery Ln

MiddleburyVT05753

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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Showing Results 1-25, Page 1 of 1

Chestertown, NY Local Guide

Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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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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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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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 Chestertown, NY Rentals by Map

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See the most popular apartments and homes in Chestertown, NY

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Chestertown, NY Apartments Map
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Chestertown, NY Rental Homes Map

Frequently Asked Questions about Chestertown

What type of rentals are currently available in Chestertown?

There are currently 50 Apartments for Rent in Chestertown, NY with pricing that ranges from $985 to $4,309. There are also 42 Single Family Homes for rent, Condos, and Townhome rentals currently available in Chestertown ranging from $1,000 to $48,500.

What is the current price range for Rental Homes in Chestertown?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Chestertown ranges from $1,000 to $48,500 with an average monthly rent of $5,019.

How much are larger Three and Four Bedroom Rentals in Chestertown?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Chestertown range from $1,225 to $4,263, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,425 to $40,000. Four Bedroom Single-Family rentals are also available starting from $2,250 and Four Bedroom Apartments start at $2,500.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.