Homes for Rent in Winchester, MA Under $2,500 (54 Rentals)

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property at 22 High St

22 High St, Unit 11

22 High St
MedfordMA02155

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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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 24 South St

24 South St, Unit 3

24 South St
MedfordMA02155

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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property at 3 Brattle Dr

3 Brattle Dr, Unit 8

3 Brattle Dr
ArlingtonMA02474
property at 1 Brattle Dr

1 Brattle Dr, Unit 1

1 Brattle Dr
ArlingtonMA02474
property at 15 Old Colony Ln

15 Old Colony Ln

ArlingtonMA02476

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 282 Main St

282 Main St, Unit 2

282 Main St
StonehamMA02180
property at 537 Main St

537 Main St

WoburnMA01801
property at 537 Main St

537 Main St

WoburnMA01801
property at 19 Arizona Ter

19 Arizona Ter

ArlingtonMA02474

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.

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Winchester, MA Local Guide

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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Frequently Asked Questions about Winchester

What type of rentals are currently available in Winchester?

There are currently 716 Apartments for Rent in Winchester, MA with pricing that ranges from $1,100 to $10,400. There are also 506 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $975 to $40,000.

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

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $975 to $40,000 with an average monthly rent of $4,958.

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

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,450 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,425 and Four Bedroom Apartments start at $3,000.

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.

decorative image for The 10 Best Affordable Neighborhoods in Boston, MA article

The 10 Best Affordable Neighborhoods in Boston, MA

Written by: Amelia Ramstead

Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

decorative image for The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro article

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

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.

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

Written by: Christine Leonard, Esq.

Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.

decorative image for Roommate Matching: Finding the Right Fit and Avoiding Pitfalls article

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

Written by: Cheryl Bowman

A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.