2 Bedroom Apartments for Rent in Winchester, MA (189 Rentals)

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property at 26 Lebanon St

$2,550

Total Monthly Price

Total Monthly Price

Base Rent
$2,550
Total Monthly Price
$2,550

2 Bedroom, 1 Bath Home for Rent

Available Now

26 Lebanon St

WinchesterMA01890
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10 Winchester Plz
2 Bedroom Apartments

10 Winchester Plz

10 Winchester PlzWinchester, MA 01890
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The Village
2 Bedroom Apartments

The Village

171 Swanton StWinchester, MA 01890
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40 Elmwood Ave
2 Bedroom Apartments

40 Elmwood Ave

40 Elmwood AveWinchester, MA 01890

Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

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Hanover Stoneham
Rent Specials
$3,524 - $4,331
Total Monthly Price

Total Monthly Price

Base Rent
$2,141 - $4,986
Total Monthly Price
Varies
2 Bedroom Apartments Available Now

Hanover Stoneham

95 Maple StStoneham, MA 02180
Luxury
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  • Customer Reviewed
  • Utilities Included
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The Mave
$3,270 - $5,440
Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,715 - $5,440
Total Monthly Price
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2 Bedroom Apartments Available Now

The Mave

225 Fallon RdStoneham, MA 02180
Family Friendly
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  • Customer Reviewed
  • 3D Tour

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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Arlington 360
$3,986 - $4,882
Total Monthly Price

Total Monthly Price

Base Rent
$3,353 - $11,325
Total Monthly Price
Varies
2 Bedroom Apartments Available Now

Arlington 360

4105 Symmes CirArlington, MA 02474
Corporate Housing
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  • Customer Reviewed
  • Utilities Included
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Arlington Gardens
$2,200 - $2,400
Total Monthly Price16 Month Lease Term

Total Monthly Price

Base Rent
$2,000 - $2,400
Total Monthly Price
Varies
2 Bedroom Apartments Contact Us For Availability

Arlington Gardens

130 Everett StArlington, MA 02474
Transit Friendly
  • Verified

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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84 North St, Unit 1A, Unit 1A
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200
Total Monthly Price
$3,200
2 Bedroom Apartment Available Jun 1

84 North St, Unit 1A, Unit 1A

84 North StMedford, MA 02155
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538 Main St, Unit 2, Unit 2
$2,650
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,650
Total Monthly Price
$2,650
2 Bedroom Apartment Available Jun 1

538 Main St, Unit 2, Unit 2

538 Main StStoneham, MA 02180
Cost Per Sq.Ft.
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39 Sterling St, Unit 1, Unit 1
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100
Total Monthly Price
$3,100
2 Bedroom Apartment Available Sep 1

39 Sterling St, Unit 1, Unit 1

39 Sterling StSomerville, MA 02144
Cost Per Sq.Ft.
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100 Conwell Ave, Unit 2, Unit 2
$3,100
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100
Total Monthly Price
$3,100
2 Bedroom Apartment Available Jul 1

100 Conwell Ave, Unit 2, Unit 2

100 Conwell AveSomerville, MA 02144
Cost Per Sq.Ft.
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77 Fairfax St
$3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,200 - $3,300
Total Monthly Price
$2,200 - $3,300
2 Bedroom Apartment Available Jun 1

77 Fairfax St

77 Fairfax StSomerville, MA 02144
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48 Nashua St
$2,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,750 - $2,400
Total Monthly Price
$1,750 - $2,400
2 Bedroom Apartment Available Now

48 Nashua St

48 Nashua StWoburn, MA 01801
Affordability
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Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

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Winchester, MA Local Guide

Largest Available Winchester 2 Bedroom Apartments

The largest available 2 Bedroom apartment unit in Winchester, MA is found at Tudor Glen Village in the Turning Mill neighborhood and is 1,500 square feet priced from $3,295. Arlington 360 in the Arlington Center neighborhood has the second largest 2 Bedroom, which is sized at 1,483 square feet and currently listed start at $4,882. Here is today’s list of the largest available 2 Bedroom units in Winchester:

Apartment ListingModel NameSquare FootagePriced From
Tudor Glen VillageAlder (Townhouse w/basement)1,500 Sq Ft$3,295
Arlington 360T1R Townhome1,483 Sq Ft$4,882
Hanover StonehamM1,322 Sq Ft$4,271
Sanctuary Winchester North2M Den1,253 Sq Ft$4,378
GlenBrook Estates2x11,150 Sq Ft$2,750
The Legacy at Arlington Center2 Bedroom/2 Bathroom Flat1,115 Sq Ft$3,700
Washington Crossing ApartmentsHuntington 2B2B1,108 Sq Ft$3,146
The Devon at Weiss Farm2 Bed 2 Bath1,108 Sq Ft$3,387
Brigham Square ApartmentsMoxie1,059 Sq Ft$4,030
The MaveB2AP1,053 Sq Ft$3,630

Cheapest Available Winchester 2 Bedroom Apartments

As of April 28, 2026 the lowest priced 2 Bedroom apartment unit in Winchester, MA is the 2 bedroom Model starting from $2,250 at Leisure Lane Apartments in the West Side neighborhood. The second most affordable Winchester 2 Bedroom is the 2 Bedroom Model at Mill Street Gardens starting at $2,250 in the Nobility Hill neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $3,330. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
Leisure Lane Apartments2 bedroom$2,250
Mill Street Gardens2 Bedroom$2,250
Old Colony Apartments2 bedroom$2,300
Mill Street HeightsA$2,400
840-846 Massachusetts Ave840 - 2 Bedroom$2,500
174 Summer St2 Bedroom$2,575
Shaker Glen VillageElm$2,595

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

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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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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 Leisure Lane Apartments listed at $2,250.

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

The average rent for a 2 Bedroom Apartment in Winchester is $3,330.

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

Today's apartment with the most square footage in Winchester is a 1,500 square feet unit starting from $3,295 at Tudor Glen Village.

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

The average size for a 2 Bedroom rental in Winchester is currently 2,342 sq ft.

Expert Rental Resources

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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