Cheap Apartments for Rent in Winchester, MA from $1,300 (56 Rentals)

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

property at 7 Old Colony Ln

7 Old Colony Ln

ArlingtonMA02476

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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property at 4 Colonial Village Dr

4 Colonial Village Dr

ArlingtonMA02474
property at 455 Main St

455 Main St

StonehamMA02180

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 4 Old Colony Ln

4 Old Colony Ln

ArlingtonMA02476
property at 121 Franklin St

121 Franklin St

StonehamMA02180
property at 276 Massachusetts Ave

276 Massachusetts Ave

ArlingtonMA02474

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street

Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

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4 Colonial Village Dr, Unit 4
$2,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,200
Total Monthly Price
$2,200
1 Bedroom Apartment Available Now

4 Colonial Village Dr, Unit 4

4 Colonial Village DrArlington, MA 02474
Affordability
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The Devon at Weiss Farm
Rent Specials
$2,247 - $5,435
Total Monthly Price

Total Monthly Price

Base Rent
$2,247 - $5,435
Total Monthly Price
$2,247 - $5,435
Studio to 3 Bedroom Apartments Available Now

The Devon at Weiss Farm

168 Franklin StStoneham, MA 02180
Pet Friendly
  • Verified
  • Utilities Included
  • Matterport 3D Tour
property at 22 Franklin St

22 Franklin St

WoburnMA01801

Explore Like a Local: The Insider's Guide to Boston

Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.

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property at 50 Cambridge Rd

50 Cambridge Rd

WoburnMA01801
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The Artemis at Arlington Heights
Rent Specials
$2,252 - $4,950
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,252 - $4,950
Total Monthly Price
$2,252 - $4,950
Studio to 3 Bedroom Apartments Available Now

The Artemis at Arlington Heights

1163 Massachusetts AveArlington, MA 02476
Affordability
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  • Customer Reviewed
  • Matterport 3D Tour
property at 8 Menotomy Rd

8 Menotomy Rd

ArlingtonMA02476
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667 Main St
1 Bedroom Apartments

667 Main St

667 Main StWoburn, MA 01801
  • Utilities Included
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Stoneham House
Studio to 2 Bedroom Apartments

Stoneham House

180-222 Central StStoneham, MA 02180
  • Utilities Included
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411 Main St
1 to 2 Bedroom Apartments

411 Main St

411 Main StStoneham, MA 02180
  • Utilities Included

Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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Winchester, MA Local Guide

Cheapest Available Winchester Apartments for Rent

 

The cheapest available apartment rental in Winchester, MA is a 1 Bed unit found at Leisure Lane Apartments in the West Side neighborhood priced from $1,695. Old Colony Apartments in the Rock Meadow neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,850. Here is today’s list of the most affordable Winchester apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Leisure Lane Apartmentssmall 1 bedroom1BR,1BA$1,695
Old Colony ApartmentsStudioStudio,1BA$1,850
Mass Ave 333-Allen Street Apartments1 Bed 1 Bath 650sf1BR,1BA$1,950
Mill Street Gardens1 Bedroom, 1 Bath1BR,1BA$1,950
Brattle Drive ApartmentsOne Bedroom1BR,1BA$1,950

Best Value Apartments for Rent in Winchester, MA

As of October 24, 2025 the best value apartment in the Winchester area is the $0.30 price per square foot 1 Victoria St Model at 1 Victoria St, Unit 1A in the in the Strawberry Hill neighborhood starting from $2,975. The second greatest value Winchester apartment is the 96 Conwell Ave Model at 96 Conwell Ave, Unit 1 starting at $3,000 with a $0.30 price per square foot in the Strawberry Hill 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.
1 Victoria St, Unit 1A1 Victoria St2BR,1BA$0.30
96 Conwell Ave, Unit 196 Conwell Ave2BR,1BA$0.30
96 Conwell Ave, Unit 296 Conwell Ave2BR,1BA$0.30
96 Conwell Ave, Unit 196 Conwell Ave2BR,1BA$0.30
69 Raymond Ave, Unit 1R69 Raymond Ave2BR,1BA$0.26
1 Victoria St, Unit #1A1 Victoria St2BR,1BA$0.30
79 Capen St, Unit 179 Capen St2BR,1BA$0.27
69 Raymond Ave, Unit 1R69 Raymond Ave2BR,1BA$0.26
29 Capen St, Unit #229 Capen St2BR,1.5BA$0.30
8 Cross St, Unit 18 Cross St3BR,1.5BA$0.30

Apartment Common Area Rules: What Renters Need to Know

From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.

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Boston Neighborhood Guide: Living Near UMass, MGH, and State Street

Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.

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Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Top Neighborhoods Near Boston Colleges and Universities

Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com

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

Explore Winchester, MA Rentals by Map

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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 $1,750.

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

The lowest price for a Cheap One Bedroom Winchester Apartment is $1,695 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.

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.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.