2 Bedroom Apartments for Rent in Winchester, MA (161 Rentals)

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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
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Glenbrook Estates
$2,800 - $2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,450 - $2,900
Total Monthly Price
$2,450 - $2,900
2 Bedroom Apartments Available Sep 15

Glenbrook Estates

200 Bedford RdWoburn, MA 01801
Family Friendly
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  • Utilities Included

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Hanover Stoneham
Rent Specials
$4,653
Total Monthly Price

Total Monthly Price

Base Rent
$2,256 - $5,628
Total Monthly Price
Varies
2 Bedroom Apartments Available Now

Hanover Stoneham

95 Maple StStoneham, MA 02180
Luxury
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The Mave
$3,325 - $5,440
Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,680 - $5,440
Total Monthly Price
Varies
2 Bedroom Apartments Available Now

The Mave

225 Fallon RdStoneham, MA 02180
Family Friendly
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  • Customer Reviewed
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Stonehill Towers
$3,100 - $3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500 - $3,300
Total Monthly Price
Varies
2 Bedroom Apartments Available Nov 1

Stonehill Towers

5 Stonehill DrStoneham, MA 02180
Corporate Housing
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

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Arlington 360
$4,428 - $4,639
Total Monthly Price

Total Monthly Price

Base Rent
$3,042 - $8,871
Total Monthly Price
Varies
2 Bedroom Apartments Available Sep 11

Arlington 360

4105 Symmes CirArlington, MA 02474
Corporate Housing
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  • Utilities Included
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Arlington Gardens
$2,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,300 - $2,600
Total Monthly Price
Varies
2 Bedroom Apartments Available Aug 11

Arlington Gardens

130 Everett StArlington, MA 02474
Transit Friendly
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38 Rawson Rd, Unit 2
$2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900
Total Monthly Price
$2,900
2 Bedroom Apartment Available Sep 1

38 Rawson Rd, Unit 2

38 Rawson RdArlington, MA 02474
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48 Nashua St, Unit 2
$2,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500
Total Monthly Price
$2,500
2 Bedroom Apartment Available Now

48 Nashua St, Unit 2

48 Nashua StWoburn, MA 01801
Cost Per Sq.Ft.
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18 Silk St
$2,825
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,825
Total Monthly Price
$2,825
2 Bedroom Apartment Available Aug 1

18 Silk St

18 Silk StArlington, MA 02474
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97 W Quincy St, Unit 1
$3,195
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,195
Total Monthly Price
$3,195
2 Bedroom Apartment Available Aug 31

97 W Quincy St, Unit 1

97 W Quincy StSomerville, MA 02144
Cost Per Sq.Ft.

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14 Irvington Rd, Unit 1
$2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900
Total Monthly Price
$2,900
2 Bedroom Apartment Available Sep 1

14 Irvington Rd, Unit 1

14 Irvington RdSomerville, MA 02144
Affordability
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81 Conwell Ave, Unit 3
$4,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200
Total Monthly Price
$4,200
2 Bedroom Apartment Available Sep 1

81 Conwell Ave, Unit 3

81 Conwell AveSomerville, MA 02144
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30 Sterling St, Unit B2
$3,200
Total Monthly Price12 Month Lease Term

Total Monthly Price

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

30 Sterling St, Unit B2

30 Sterling StSomerville, 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
$2,100 - $3,300
Total Monthly Price
$2,100 - $3,300
2 Bedroom Apartment Available Now

77 Fairfax St

77 Fairfax StSomerville, MA 02144
Cost Per Sq.Ft.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

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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 $3,095. Sanctuary Winchester West in the Cummingsville neighborhood has the second largest 2 Bedroom, which is sized at 1,389 square feet and currently listed start at $4,630. 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$3,095
Sanctuary Winchester WestB3 Den1,389 Sq Ft$4,630
Hanover StonehamM1,322 Sq Ft$4,653
Washington Crossing ApartmentsExeter 2B2B1,158 Sq Ft$3,123
The Legacy at Arlington Center2 Bedroom/2 Bathroom Flat1,115 Sq Ft$3,700
The Devon at Weiss Farm2 Bed 2 Bath1,108 Sq Ft$3,516
Sanctuary Winchester North2B1,108 Sq Ft$3,853
Brigham Square ApartmentsMoxie1,059 Sq Ft$3,810
The MaveB2AP1,053 Sq Ft$3,435
840-846 Massachusetts Ave846 - 2 Bedroom1,005 Sq Ft$2,950

Cheapest Available Winchester 2 Bedroom Apartments

As of July 28, 2026 the lowest priced 2 Bedroom apartment unit in Winchester, MA is the 2 Bedroom Model starting from $2,250 at Mill Street Gardens in the Nobility Hill neighborhood. The second most affordable Winchester 2 Bedroom is the 2BR/1.0BA Model at 30 Pomeworth Street starting at $2,295 . The average price for all 2 Bedroom apartments in Winchester is currently $3,347. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:

Apartment ListingModel NamePriced From
Mill Street Gardens2 Bedroom$2,250
30 Pomeworth Street2BR/1.0BA$2,295
Old Colony Apartments2 bedroom$2,300
Brookside ApartmentsB1$2,475

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

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Top Neighborhoods Near Boston Colleges and Universities

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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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Remember the 3 Rules of Real Estate:
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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 Mill Street Gardens 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 $3,347.

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 $3,095 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 1,327 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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