Cheap Apartments for Rent in Winchester, MA from $1,400 (77 Rentals)

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2 Elmwood Ave
1 Bedroom Apartments

2 Elmwood Ave

2 Elmwood AveWinchester, MA 01890

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 11 Allen St

11 Allen St

ArlingtonMA02474
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$1,705
Brookside ApartmentsA11BR,1BA$2,000

Best Value Apartments for Rent in Winchester, MA

As of March 18, 2025 the best value apartment in the Winchester area is the $0.23 price per square foot 78 Decatur St Model at 78 Decatur St, Unit 3 in the in the East Arlington neighborhood starting from $2,300. The second greatest value Winchester apartment is the 1011 Massachusetts Ave Model at 1011 Massachusetts Ave, Unit 2 starting at $2,295 with a $0.23 price per square foot in the Rock Meadow 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.
78 Decatur St, Unit 378 Decatur St1BR,1BA$0.23
1011 Massachusetts Ave, Unit 21011 Massachusetts Ave1BR,1BA$0.23
47 Orchard St, Unit 347 Orchard St3BR,1BA$0.27
79 Capen St, Unit 179 Capen St2BR,1BA$0.27
77 Fairfax St, Unit B77 Fairfax StStudio ,1BA$0.20
101 Boston Ave, Unit 1101 Boston Ave2BR,1BA$0.26
101 Boston Ave, Unit 1101 Boston Ave2BR,1BA$0.26
95 W Adams St, Unit 195 W Adams St2BR,1BA$0.25
96 W Adams St, Unit 296 W Adams St2BR,1BA$0.26
101 Boston Ave, Unit 1101 Boston Ave2BR,1BA$0.26

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Location, Location, Location!

Explore Winchester, MA Rentals by Map

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See the most popular apartments and homes in Winchester, MA

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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 Leisure Lane Apartments listed at $1,705.

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

The lowest price for a Cheap One Bedroom Winchester Apartment is $1,905 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 $2,195 at Leisure Lane Apartments.

What is the most affordable Winchester Three Bedroom Apartment?

The best deal on a cheap Winchester Three Bedroom Apartment rental is at and starts from $2,600.

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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