Cheap Apartments for Rent in Winchester, MA from $1,400 (76 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

Search the lowest-cost Apartments available for rent right now in Winchester.

close
View Me
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

Read Article
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

Best Value Apartments for Rent in Winchester, MA

As of March 16, 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

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.

decorative image of people with a giant lease agreement

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

Explore Winchester, MA Rentals by Map

Decorative image of map

See the most popular apartments and homes in Winchester, MA

View MapWinchester, MA Apartments MapView MapWinchester, MA Rental Homes Map

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.

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 Understanding Amenity Fees: Know Where You Might Be Able to Save Money article

Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

decorative image for What to Know About Fees and Fines When Renting article

What to Know About Fees and Fines When Renting

Written by: Trey Huguley

When it comes to renting a new apartment or home there can be a number of fees that you will want to keep in mind going into the process.

decorative image for Battling the Butts: Your Guide to the Reality of Smoke-Free Renting article

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.