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Rent Specials
$3,879 - $4,063
Plus Fees
2 Bedroom Apartments Available NowSanctuary Winchester West
416 Cambridge StWinchester, MA 01890
2 Bedroom Apartments for Rent in Winchester, MA (175 Rentals)
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Rent Specials
$3,566 - $4,216
Plus Fees
2 Bedroom Apartments Available NowSanctuary Winchester North
25-35 River StWinchester, MA 01890
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
17 Linden St, Unit 17 Linden St
17 Linden StWinchester, MA 01890
36 Cross St
WinchesterMA01890
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2 Bedroom Apartments
40 Elmwood Ave
40 Elmwood AveWinchester, 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 Village
171 Swanton StWinchester, MA 01890
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2 Bedroom Apartments
The Willows at Winchester
7 Conant RdWinchester, MA 01890
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$2,999 - $3,318
Plus Fees
2 Bedroom Apartments Available NowWashington Crossing Apartments
55 Cedar StWoburn, MA 01801
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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Rent Specials
$3,063 - $3,733
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,339 - $5,553
Total Monthly Price
Varies
The Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
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$3,830 - $4,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available Apr 12Total Monthly Price
Base Rent
$2,550 - $4,950
Total Monthly Price
Varies
The Artemis at Arlington Heights
1163 Massachusetts AveArlington, MA 02476
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$3,270 - $5,150
Total Monthly Price1 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,510 - $5,150
Total Monthly Price
Varies
The Mave
225 Fallon RdStoneham, MA 02180
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Rent Specials
$3,595 - $3,885
Plus Fees
2 Bedroom Apartments Available NowBrigham Square Apartments
30 Mill StArlington, MA 02476
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Rent Specials
$2,714 - $4,765
Plus Fees
2 Bedroom Apartments Available NowHanover Stoneham
95 Maple StStoneham, MA 02180
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Rent Specials
$2,600 - $2,850
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowGlenBrook Estates
200 Bedford RdWoburn, 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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$2,800 - $2,900
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowStonehill 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
$2,800 - $4,100
Total Monthly Price
$2,800 - $4,100
The Legacy at Arlington Center
438 Massachusetts AveArlington, MA 02474
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$2,650 - $3,050
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowMill Street Heights
59 Mill StWoburn, MA 01801
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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Rent Specials
$2,900 - $3,200
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Now12 Montvale Ave
12 Montvale AveWoburn, MA 01801
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$2,400 - $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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$3,150
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Apr 1048 Pleasant Street
48 Pleasant StStoneham, MA 02180
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Rent Specials
$2,250 - $2,450
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Jul 1Mill Street Gardens
57 Mill StWoburn, MA 01801
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$4,575 - $5,093
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,396 - $10,426
Total Monthly Price
Varies
Arlington 360
4105 Symmes CirArlington, MA 02474
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$2,300
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowBrattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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$2,250 - $2,645
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowLeisure Lane Apartments
100 Leisure LnStoneham, MA 02180
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$2,575 - $2,625
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Now174 Summer St
174 Summer StArlington, MA 02474
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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
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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$2,400
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowArlington Gardens Apartments
130 Everett StArlington, MA 02474
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$2,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,250
Total Monthly Price
$2,250
25 Arlington Rd, Unit Apt 1-1
25 Arlington RdWoburn, MA 01801
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$2,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
68 High St, Unit 2
68 High StStoneham, MA 02180
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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Apr 1Total Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
15 Wheelwright Rd, Unit 1
15 Wheelwright 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
186 Powder House Blvd, Unit 2
186 Powder House BlvdSomerville, MA 02144
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$3,100
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available May 2Total Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
376 Massachusetts Ave, Unit 32
376 Massachusetts AveArlington, MA 02474
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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 NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
8 Eastern Ave, Unit 1st floor
8 Eastern AveWoburn, MA 01801
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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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$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
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
79 Capen St, Unit 2
79 Capen StMedford, MA 02155
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$2,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$1,850 - $2,000
Total Monthly Price
$1,850 - $2,000
224 Main St
224 Main StWoburn, MA 01801
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$2,950
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,950
Total Monthly Price
$2,950
6 Gloucester St, Unit 2 bedrooms
6 Gloucester StArlington, MA 02476
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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
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
26 Bradlee Rd
26 Bradlee RdMedford, MA 02155
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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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$2,750
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jun 1Total Monthly Price
Base Rent
$2,750
Total Monthly Price
$2,750
221 Massachusetts Ave, Unit 2
221 Massachusetts AveArlington, MA 02474
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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
28 Clark St, Unit 1
28 Clark StMedford, MA 02155
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$3,150
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jun 1Total Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
5 Freeman St, Unit 2
5 Freeman StArlington, MA 02474
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$3,150
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jun 1Total Monthly Price
Base Rent
$3,150
Total Monthly Price
$3,150
5 Freeman St, Unit 1
5 Freeman StArlington, MA 02474
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Studio Apartments | $2,189 | $1,700 | $2,731 |
| Winchester 1 Bedroom Apartments | $2,695 | $1,600 | $4,355 |
Winchester 2 Bedroom Apartments | $3,250 | $2,000 | $5,150 |
| Winchester 3 Bedroom Apartments | $3,672 | $2,300 | $5,761 |
| Winchester 4 Bedroom Apartments | $4,427 | $3,300 | $6,000 |
| Winchester 5 Bedroom Apartments | $6,068 | $1,110 | $10,000+ |
| Winchester 6 Bedroom Apartments | $7,193 | $5,300 | $8,437 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Apartments in Winchester
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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 Old Colony Apartments in the Rock Meadow neighborhood and is 3,070 square feet priced from $2,400. Tudor Glen Village in the Turning Mill neighborhood has the second largest 2 Bedroom, which is sized at 1,500 square feet and currently listed start at $3,295. Here is today’s list of the largest available 2 Bedroom units in Winchester:
| Apartment Listing | Model Name | Square Footage | Priced From |
|---|---|---|---|
| Old Colony Apartments | 2 bedroom | 3,070 Sq Ft | $2,400 |
| Tudor Glen Village | Alder (Townhouse w/basement) | 1,500 Sq Ft | $3,295 |
| Arlington 360 | T1R Townhome | 1,483 Sq Ft | $5,093 |
| Hanover Stoneham | M | 1,322 Sq Ft | $4,360 |
| Stonehill Towers | Two Bedroom | 1,279 Sq Ft | $2,800 |
| Sanctuary Winchester North | 2M Den | 1,253 Sq Ft | $4,116 |
| Brigham Square Apartments | Dallin | 1,178 Sq Ft | $3,885 |
| The Legacy at Arlington Center | 2 Bedroom/2 Bathroom Flat | 1,115 Sq Ft | $3,700 |
| Washington Crossing Apartments | Huntington 2B2B | 1,108 Sq Ft | $3,280 |
| The Devon at Weiss Farm | 2 Bed 2 Bath | 1,108 Sq Ft | $3,063 |
Cheapest Available Winchester 2 Bedroom Apartments
As of March 14, 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 Two Bedroom Model at Brattle Drive Apartments starting at $2,300 in the Rock Meadow neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $3,250. Here is today’s list of the cheapest available 2 Bedroom options in Winchester:
| Apartment Listing | Model Name | Priced From |
|---|---|---|
| Leisure Lane Apartments | 2 bedroom | $2,250 |
| Brattle Drive Apartments | Two Bedroom | $2,300 |
| Old Colony Apartments | 2 bedroom | $2,400 |
| Arlington Gardens Apartments | 2 Bedroom | $2,400 |
| Tudor Glen Village | The Birch | $2,495 |
| 840-846 Massachusetts Ave | 840 - 2 Bedroom | $2,500 |
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.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleTop 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 $3,250.
What is the largest available 2 Bedroom Winchester Apartment for rent?
Today's apartment with the most square footage in Winchester is a 3,070 square feet unit starting from $2,400 at Old Colony Apartments.
What is the average size for Winchester 2 Bedroom Apartments for rent?
The average size for a 2 Bedroom rental in Winchester is currently 1,885 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
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
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Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.