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Rent Specials
$4,615 - $5,161
Plus Fees
2 Bedroom Apartments Available NowSanctuary Winchester West
416 Cambridge StWinchester, MA 01890
2 Bedroom Apartments for Rent in Winchester, MA (162 Rentals)
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Rent Specials
$4,073 - $4,303
Plus Fees
2 Bedroom Apartments Available Jun 17Sanctuary Winchester North
25-35 River StWinchester, MA 01890
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2 Bedroom Apartments
10 Winchester Plz
10 Winchester PlzWinchester, MA 01890
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2 Bedroom Apartments
Winchester Gardens
1-11 George RdWinchester, MA 01890
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2 Bedroom Apartments
The Willows at Winchester
7 Conant RdWinchester, MA 01890
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2 Bedroom Apartments
The Village
171 Swanton StWinchester, MA 01890
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2 Bedroom Apartments
40 Elmwood Ave
40 Elmwood AveWinchester, MA 01890
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$2,968 - $3,747
Plus Fees
2 Bedroom Apartments Available NowWashington Crossing Apartments
55 Cedar StWoburn, MA 01801
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Rent Specials
$3,338 - $4,397
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,410 - $4,397
Total Monthly Price
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The Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
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Rent Specials
$2,865 - $4,241
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,448 - $5,408
Total Monthly Price
Varies
Hanover Stoneham
95 Maple StStoneham, MA 02180
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.
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Rent Specials
$4,030 - $4,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available Jul 1Total Monthly Price
Base Rent
$2,765 - $4,890
Total Monthly Price
Varies
The Artemis at Arlington Heights
1163 Massachusetts AveArlington, MA 02476
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Rent Specials
$2,650
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,400 - $2,650
Total Monthly Price
$2,400 - $2,650
GlenBrook Estates
200 Bedford RdWoburn, MA 01801
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$3,955 - $4,070
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,832 - $5,210
Total Monthly Price
Varies
Brigham Square Apartments
30 Mill StArlington, MA 02476
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$3,325 - $5,440
Total Monthly Price1 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,680 - $5,440
Total Monthly Price
Varies
The Mave
225 Fallon RdStoneham, MA 02180
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$4,995 - $5,095
Plus Fees1 Month Lease Term
2 Bedroom Apartments Available NowTownhomes at 285
285 Locust StWoburn, MA 01801
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$2,495 - $3,295
Plus Fees
2 Bedroom Apartments Available NowTudor Glen Village
111 Locust StWoburn, MA 01801
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$2,400 - $3,075
Plus Fees12 Month Lease Term
2 Bedroom Apartments Contact Us For AvailabilityMill Street Heights
59 Mill StWoburn, MA 01801
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$3,100
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available Jul 25Total Monthly Price
Base Rent
$2,500 - $3,100
Total Monthly Price
Varies
Stonehill Towers
5 Stonehill DrStoneham, MA 02180
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$3,700 - $4,100
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,700 - $4,100
Total Monthly Price
Varies
The Legacy at Arlington Center
438 Massachusetts AveArlington, MA 02474
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$2,900
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Now292 Boston Ave
292 Boston AveMedford, MA 02155
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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$3,100
Plus Fees
2 Bedroom Apartments Available Now69 Raymond Ave
69 Raymond AveSomerville, MA 02144
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Rent Specials
$2,200 - $2,550
Plus Fees12 Month Lease Term
2 Bedroom Apartments Contact Us For AvailabilityBrattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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Rent Specials
$2,250 - $2,700
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
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$3,960 - $4,595
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,047 - $9,344
Total Monthly Price
Varies
Arlington 360
4105 Symmes CirArlington, MA 02474
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$2,300 - $2,500
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowOld Colony Apartments
1-17 Old Colony LnArlington, MA 02476
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$2,600
Plus Fees
2 Bedroom Apartments Available Now49 Summer St
49 Summer StArlington, MA 02474
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$2,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available Jul 10Total Monthly Price
Base Rent
$2,200 - $2,400
Total Monthly Price
Varies
Arlington Gardens
130 Everett StArlington, MA 02474
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$3,025
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Jul 14Lofts at 307 Main LLC
307 Main StWoburn, MA 01801
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$2,500 - $2,700
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Now840-846 Massachusetts Ave
840 Massachusetts AveArlington, MA 02476
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$3,000
Plus Fees
2 Bedroom Apartments Available Now79 Montvale Ave
79 Montvale AveWoburn, MA 01801
Navigating the Rental Market: Tips for First-Time Renters
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jun 15Total Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
106 Elm St, Unit 106 Elm First Fooor
106 Elm StStoneham, MA 02180
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 1, 2027Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
29R Wachusett Ave, Unit 29 R Wachusett Ave.
29R Wachusett AveArlington, MA 02476
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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
491 Main St, Unit 2br apartment
491 Main StWoburn, MA 01801
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
159 Main St
159 Main StStoneham, MA 02180
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
25 Arlington Rd, Unit Apt #3 6
25 Arlington RdWoburn, MA 01801
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$3,150
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
63 Newport St, Unit 63 Newport Street
63 Newport StArlington, MA 02476
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$3,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
27 Orvis Rd, Unit 27 Orvis Rd
27 Orvis RdArlington, MA 02474
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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
66 Cleveland St, Unit 1
66 Cleveland StArlington, MA 02474
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$2,995
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,995
Total Monthly Price
$2,995
286 Main St, Unit 3
286 Main StWoburn, MA 01801
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jul 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
10 Davis St, Unit 10
10 Davis StWoburn, MA 01801
Renting Smart: Lease Basics Every Renter Needs
Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com
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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jun 15Total Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
26 Grove St, Unit 12
26 Grove StArlington, MA 02476
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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
59 Conwell Ave, Unit 1
59 Conwell AveSomerville, MA 02144
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$3,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
165 Radcliffe Rd, Unit #169
165 Radcliffe RdBelmont, MA 02478
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$2,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,750 - $2,400
Total Monthly Price
$1,750 - $2,400
48 Nashua St
48 Nashua StWoburn, MA 01801
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$1,995
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,995
Total Monthly Price
$1,995
102 Main St, Unit B
102 Main StWoburn, MA 01801
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
22 Bradlee Rd
22 Bradlee RdMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
29 Capen St
29 Capen StMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Aug 31Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
1 Victoria St, Unit 1A
1 Victoria StSomerville, MA 02144
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$2,650
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,650
Total Monthly Price
$2,650
15 Wheelwright Rd, Unit 1
15 Wheelwright RdMedford, MA 02155
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$3,550
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Aug 1Total Monthly Price
Base Rent
$3,550
Total Monthly Price
$3,550
37 Clark St, Unit B
37 Clark StMedford, MA 02155
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
Winchester, MA Local Guide
How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Studio Apartments | $2,248 | $1,650 | $2,832 |
| Winchester 1 Bedroom Apartments | $2,696 | $1,110 | $4,215 |
Winchester 2 Bedroom Apartments | $3,356 | $1,995 | $5,440 |
| Winchester 3 Bedroom Apartments | $3,790 | $950 | $6,297 |
| Winchester 4 Bedroom Apartments | $4,172 | $2,900 | $5,300 |
| Winchester 5 Bedroom Apartments | $6,088 | $4,200 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
See all Apartments in WinchesterExplore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
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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. Arlington 360 in the Arlington Center neighborhood has the second largest 2 Bedroom, which is sized at 1,394 square feet and currently listed start at $4,260. Here is today’s list of the largest available 2 Bedroom units in Winchester:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Tudor Glen Village | Alder (Townhouse w/basement) | 1,500 Sq Ft | $3,095 |
| Arlington 360 | B8.1R | 1,394 Sq Ft | $4,260 |
| Sanctuary Winchester West | B3 Den | 1,389 Sq Ft | $5,161 |
| Hanover Stoneham | Ma | 1,322 Sq Ft | $2,865 |
| Washington Crossing Apartments | Exeter 2B2B | 1,158 Sq Ft | $3,013 |
| GlenBrook Estates | 2 Bedroom | 1,150 Sq Ft | $2,650 |
| The Legacy at Arlington Center | 2 Bedroom/2 Bathroom Flat | 1,115 Sq Ft | $3,700 |
| The Devon at Weiss Farm | 2 Bed 2 Bath | 1,108 Sq Ft | $3,338 |
| Brigham Square Apartments | Moxie | 1,059 Sq Ft | $3,801 |
| The Mave | B2AP | 1,053 Sq Ft | $3,480 |
Cheapest Available Winchester 2 Bedroom Apartments
As of June 13, 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 2 bedroom Model at Old Colony Apartments starting at $2,300 in the Rock Meadow neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $3,356. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Mill Street Gardens | 2 Bedroom | $2,250 |
| Old Colony Apartments | 2 bedroom | $2,300 |
| Shaker Glen Village | Elm | $2,495 |
| Tudor Glen Village | The Birch | $2,495 |
| 840-846 Massachusetts Ave | 840 - 2 Bedroom | $2,500 |
| 174 Summer St | 2 Bedroom | $2,575 |
| 49 Summer St | 2x1 | $2,600 |
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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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
Read ArticleReal 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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The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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See the most popular apartments and homes in Winchester, MA
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 $3,356.
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 1,956 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.
Helpful Local Expert Guides
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.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts. Getting to know your new neighborhood is one of the best parts of moving, and we’re excited to help you get started.
Articles, How-To's, and Tips
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.