Cheap Apartments for Rent in Winchester, MA from $1,400 (69 Rentals)

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Cheap Apartments in Winchester.

property at 200 Swanton St

200 Swanton St

WinchesterMA01890

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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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Read our practical guide to landlord and tenant rights. Understand protected classes, reasonable accommodations, and legal exceptions to prevent housing discrimination.

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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

Cheapest Available Winchester Apartments for Rent

 

The cheapest available apartment rental in Winchester, MA is a Studio unit found at Leisure Lane Apartments in the West Side neighborhood priced from $1,795. Mill Street Gardens in the West Side neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,950. Here is today’s list of the most affordable Winchester apartments for rent:

Apartment ListingModel NameBed/BathPriced From
Leisure Lane ApartmentsstudioStudio,1BA$1,795
Mill Street Gardens1 Bedroom, 1 Bath1BR,1BA$1,950
119 Pleasant StStudiosStudio,1BA$1,950

Best Value Apartments for Rent in Winchester, MA

As of May 02, 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
77 Gordon St, Unit #177 Gordon St2BR,2BA$0.23
78 Gordon St, Unit #178 Gordon St2BR,2BA$0.23
36 Montvale Ave36 Montvale Ave2BR,1BA$0.18
54 West St, Unit #1954 West St1BR,1BA$0.18
3 Forest St, Unit #2023 Forest St1BR,1BA$0.18
95 W Adams St, Unit 195 W Adams St2BR,1BA$0.25
67 Forest St, Unit 23567 Forest St1BR,1BA$0.23
118 Auburn St, Unit 1118 Auburn St2BR,1BA$0.25

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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 $1,795.

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.

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

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Boston is known for its exciting combination of early American history and modern high-tech universities and employers.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.

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Know Your Rights - How Discrimination Laws Impact Landlords and Tenants

Written by: Christine Leonard, Esq.

Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.