2 Bedroom Apartments for Rent in Winchester, MA (239 Rentals)

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40 Elmwood Ave
2 Bedroom Apartments

40 Elmwood Ave

40 Elmwood AveWinchester, MA 01890
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10 Winchester Plz
2 Bedroom Apartments

10 Winchester Plz

10 Winchester PlzWinchester, MA 01890
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171 Swanton St
2 Bedroom Apartments

171 Swanton St

171 Swanton StWinchester, 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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Winchester, MA Local Guide

Cheapest Available Winchester 2 Bedroom Apartments

As of March 28, 2025 the lowest priced 2 Bedroom apartment unit in Winchester, MA is the B1M Model starting from $2,300 at Medford Square Riverside in the Edgeworth neighborhood. The second most affordable Winchester 2 Bedroom is the The Birch Model at Tudor Glen Village starting at $2,495 in the Turning Mill neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $3,274. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
Medford Square RiversideB1M$2,300
Tudor Glen VillageThe Birch$2,495
Shaker Glen VillageElm$2,495

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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 2 Bedroom Winchester Apartments

What is the Cheapest apartment in Winchester with 2 Bedroom?

Currently the most affordable 2 Bedroom in Winchester is at Medford Square Riverside listed at $2,300.

How much is the average rent for a 2 Bedroom Winchester Apartment?

The average rent for a 2 Bedroom Apartment in Winchester is $3,274.

What is the largest available 2 Bedroom Winchester Apartment for rent?

Today's apartment with the most square footage in Winchester is a square feet unit at .

What is the average size for Winchester 2 Bedroom Apartments for rent?

The average size for a 2 Bedroom rental in Winchester is currently 2,624 sq ft.

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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Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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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.

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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.