Cheap Apartments for Rent in Winchester, MA from $1,300 (88 Rentals)

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property at 200 Swanton St

200 Swanton St

WinchesterMA01890

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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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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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

Best Value Apartments for Rent in Winchester, MA

As of July 24, 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
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
50 Conwell Ave, Unit 250 Conwell Ave3BR,1BA$0.31
29 Capen St, Unit #229 Capen St2BR,1.5BA$0.30
78 Gordon St, Unit #178 Gordon St2BR,2BA$0.23
54 S Border Rd, Unit A54 S Border Rd1BR,1BA$0.19

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

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Getting Around Winchester, MA

Walk Score®

71 / 100

Very Walkable

Most errands can be accomplished on foot

Bike Score®

67 / 100

Bikeable

Some bike infrastructure

Transit Score®

1 / 100

Minimal Transit

It may be possible to get on a bus

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Cheap Winchester Apartments

What is the Cheapest Studio apartment in Winchester?

Currently the most affordable Cheap Studio Apartment in Winchester is at 119 Pleasant St listed at $2,100.

How much is rent for a Cheap One Bedroom Winchester Apartment?

The lowest price for a Cheap One Bedroom Winchester Apartment is $1,925 at Leisure Lane Apartments.

What is the lowest price for a Cheap Two Bedroom Winchester Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Winchester is starting from $2,300 at Medford Square Riverside.

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.

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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.

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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.