3 Bedroom Homes for Rent in Winchester, MA (99 Rentals)

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property at 56 Gordon St

56 Gordon St, Unit 1

56 Gordon St
SomervilleMA02144

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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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 59 Quincy St

59 Quincy St

MedfordMA02155
property at 75 Lyman Ave

75 Lyman Ave

MedfordMA02155
property at 105 Woods Ave

105 Woods Ave, Unit 3

105 Woods Ave
SomervilleMA02144

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 77 Forest St

77 Forest St, Unit 2

77 Forest St
MedfordMA02155
property at 59 Quincy St

59 Quincy St

MedfordMA02155
property at 2 High St

2 High St, Unit 2

2 High St
SomervilleMA02144
property at 2 High St

2 High St, Unit 1

2 High St
SomervilleMA02144

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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property at 21 Jerome St

21 Jerome St

MedfordMA02155
property at 32 Irvington Rd

32 Irvington Rd

SomervilleMA02144
property at 54 Upland Rd

54 Upland Rd, Unit 2

54 Upland Rd
SomervilleMA02144

Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

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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 803 Apartments for Rent in Winchester, MA with pricing that ranges from $1,450 to $10,400. There are also 471 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $920 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 $920 to $40,000 with an average monthly rent of $4,869.

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 $2,500 to $9,547, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $5,950. Four Bedroom Single-Family rentals are also available starting from $3,300 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.

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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.

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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.

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

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

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

decorative image for Know Your Budget: Calculating What You Can Realistically Afford When Renting article

Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.