Cheap Homes for Rent in Winchester, MA from $900 (84 Rentals)

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property at 74 Sharon St

74 Sharon St

MedfordMA02155
property at 6 Boston Ave

6 Boston Ave

MedfordMA02155
property at 19 Arizona Ter

19 Arizona Ter

ArlingtonMA02474

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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property at 537 Main St

537 Main St

WoburnMA01801
property at 537 Main St

537 Main St

WoburnMA01801
property at 3 Brattle Dr

3 Brattle Dr, Unit 8

3 Brattle Dr
ArlingtonMA02474

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 282 Main St

282 Main St, Unit 2

282 Main St
StonehamMA02180
property at 15 Old Colony Ln

15 Old Colony Ln

ArlingtonMA02476
property at 1 Brattle Dr

1 Brattle Dr, Unit 1

1 Brattle Dr
ArlingtonMA02474

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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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 24 South St

24 South St, Unit 3

24 South St
MedfordMA02155

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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property at 22 High St

22 High St

MedfordMA02155
Showing Results 1-50, Page 1 of 2

Winchester, MA Local Guide

Cheapest Available Winchester Apartments for Rent

 
Apartment ListingModel NameBed/BathPriced From
Leisure Lane ApartmentsstudioStudio,1BA$1,750

Best Value Apartments for Rent in Winchester, MA

As of July 27, 2025 the best value apartment in the Winchester area is the $0.19 price per square foot 52 S Border Rd Model at 52 S Border Rd, Unit A in the in the Wyoming neighborhood starting from $1,875. The second greatest value Winchester apartment is the 52 S Border Rd Model at 52 S Border Rd, Unit A starting at $1,875 with a $0.19 price per square foot in the Wyoming neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
52 S Border Rd, Unit A52 S Border RdStudio ,1BA$0.19
52 S Border Rd, Unit A52 S Border RdStudio ,1BA$0.19
52 S Border Rd, Unit A52 S Border RdStudio ,1BA$0.19
54 S Border Rd, Unit A54 S Border Rd1BR,1BA$0.19
79 Capen St, Unit 179 Capen St2BR,1BA$0.27
5 Forest St, Unit #15 Forest St2BR,1BA$0.27
8 Forest St, Unit #18 Forest St2BR,1BA$0.27
29 Capen St, Unit #229 Capen St2BR,1.5BA$0.30
50 Conwell Ave, Unit 250 Conwell Ave3BR,1BA$0.31
69 Conwell Ave, Unit 169 Conwell Ave3BR,1BA$0.31

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 723 Apartments for Rent in Winchester, MA with pricing that ranges from $1,300 to $10,400. There are also 519 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 $4,952.

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 $2,600 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $3,150.

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 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.

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.