close
View Me
Rent Specials
$3,239 - $4,615
Plus Fees
2 Bedroom Apartments Available NowSanctuary Winchester West
416 Cambridge StWinchester, MA 01890
2 Bedroom Apartments for Rent in Winchester, MA (170 Rentals)
close
View Me
Rent Specials
Contact Us For Pricing2 Bedroom Apartments Available Now
Sanctuary Winchester North
25-35 River StWinchester, MA 01890
close
View Me
close
View Me
close
View Me
close
View Me
close
View Me
close
View Me
Rent Specials
$2,947 - $3,869
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,247 - $5,593
Total Monthly Price
$2,247 - $5,593
The Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
close
View Me
$2,671 - $3,181
Plus Fees
2 Bedroom Apartments Available NowWashington Crossing Apartments
55 Cedar StWoburn, MA 01801
close
View Me
Rent Specials
$3,800 - $4,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,252 - $4,950
Total Monthly Price
$2,252 - $4,950
The Artemis at Arlington Heights
1163 Massachusetts AveArlington, MA 02476
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.
close
View Me
Rent Specials
$2,714 - $4,678
Plus Fees
2 Bedroom Apartments Available NowHanover Stoneham
95 Maple StStoneham, MA 02180
close
View Me
$4,196
Plus Fees
2 Bedroom Apartments Available Dec 5Brigham Square Apartments
30 Mill StArlington, MA 02476
close
View Me
Rent Specials
$3,085 - $4,685
Total Monthly Price1 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,465 - $4,685
Total Monthly Price
$2,465 - $4,685
The Mave
225 Fallon RdStoneham, MA 02180
close
View Me
$2,495 - $3,295
Plus Fees
2 Bedroom Apartments Available NowTudor Glen Village
111 Locust StWoburn, MA 01801
close
View Me
Rent Specials
$2,595 - $3,200
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Nov 7Stonehill Towers
5 Stonehill DrStoneham, MA 02180
close
View Me
Rent Specials
$5,999
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$5,999
Total Monthly Price
$5,999
80 Broadway
80 BroadwayArlington, MA 02474
close
View Me
$3,700 - $4,100
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,700 - $4,100
Total Monthly Price
$3,700 - $4,100
The Legacy at Arlington Center
438 Massachusetts AveArlington, MA 02474
close
View Me
$2,600
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowOld Colony Apartments
1-17 Old Colony LnArlington, MA 02476
close
View Me
$2,195 - $2,525
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowLeisure Lane Apartments
100 Leisure LnStoneham, MA 02180
close
View Me
$4,211 - $4,242
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,466 - $7,325
Total Monthly Price
$3,466 - $7,325
Arlington 360
4105 Symmes CirArlington, MA 02474
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.
close
View Me
Rent Specials
$2,300
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Nov 4Brattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
close
View Me
Rent Specials
$2,250 - $2,350
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Nov 1Mill Street Gardens
57 Mill StWoburn, MA 01801
close
View Me
$2,200
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Dec 1Arlington Gardens Apartments
130 Everett StArlington, MA 02474
close
View Me
$2,850 - $2,950
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available Nov 15840-846 Massachusetts Ave
840 Massachusetts AveArlington, MA 02476
close
View Me
$2,350
Total Monthly Price10 Month Lease Term
2 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$2,350
Total Monthly Price
$2,350
220 Hancock St, Unit 1
220 Hancock StStoneham, MA 02180
close
View Me
$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
close
View Me
$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
245 Main St, Unit 2
245 Main StWoburn, MA 01801
close
View Me
$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
14 Massachusetts Ave, Unit 2 Bedroom 1 bath Apt
14 Massachusetts AveLexington, MA 02420
close
View Me
$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
379 Main St, Unit Main Street Woburn MA
379 Main StWoburn, MA 01801
close
View Me
$2,900
Total Monthly Price10 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
25 Laurel St, Unit 25 Laurel St.
25 Laurel StArlington, MA 02476
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.
close
View Me
$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
50 Marion Rd, Unit 1
50 Marion RdArlington, MA 02474
close
View Me
$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
close
View Me
$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
72 Marshall St, Unit 3
72 Marshall StMedford, MA 02155
close
View Me
$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
50 Marion Rd, Unit 1
50 Marion RdArlington, MA 02474
close
View Me
$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
close
View Me
$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
close
View Me
$2,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,250
Total Monthly Price
$2,250
74 Beach St, Unit Unit #3-3
74 Beach StWoburn, MA 01801
close
View Me
$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
82 North St, Unit 2
82 North StMedford, MA 02155
close
View Me
$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Nov 10Total Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
13 Higgins St, Unit 1
13 Higgins StArlington, MA 02476
close
View Me
$2,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
12 Belknap Street, Unit 1
12 Belknap StreetArlington, MA 02474
Cash 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.
close
View Me
$2,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,500
Total Monthly Price
$2,500
110 W Quincy St, Unit #1
110 W Quincy StSomerville, MA 02144
close
View Me
$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
60 Hamilton St
60 Hamilton StMedford, MA 02155
close
View Me
$2,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
8 Usher Rd, Unit 1
8 Usher RdMedford, MA 02155
close
View Me
$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
33 Irvington Rd
33 Irvington RdSomerville, MA 02144
close
View Me
$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
53 Oakland St
53 Oakland StMedford, MA 02155
close
View Me
$2,850
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,850
Total Monthly Price
$2,850
137 Sharon St, Unit 1
137 Sharon StMedford, MA 02155
close
View Me
$2,350
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,350
Total Monthly Price
$2,350
14 Cotting St, Unit 3
14 Cotting StMedford, MA 02155
close
View Me
$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
66 North St
66 North StSomerville, MA 02144
close
View Me
$3,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
235 Ashcroft Rd
235 Ashcroft RdMedford, MA 02155
close
View Me
$2,875
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,875
Total Monthly Price
$2,875
27 Holton St, Unit 1
27 Holton StMedford, MA 02155
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.
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 | $2,166 | $1,200 | $2,829 |
| Winchester 1 Bedroom Apartments | $2,669 | $1,395 | $4,195 |
Winchester 2 Bedroom Apartments | $3,230 | $2,195 | $5,999 |
| Winchester 3 Bedroom Apartments | $3,682 | $2,500 | $6,900 |
| Winchester 4 Bedroom Apartments | $4,567 | $3,000 | $8,000 |
| Winchester 5 Bedroom Apartments | $6,161 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,089 | $5,945 | $8,450 |
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
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Winchester 2 Bedroom Apartments
As of October 31, 2025 the lowest priced 2 Bedroom apartment unit in Winchester, MA is the 2 bedroom Model starting from $2,195 at Leisure Lane Apartments in the West Side neighborhood. The second most affordable Winchester 2 Bedroom is the Elm Model at Shaker Glen Village starting at $2,395 in the Turning Mill neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $3,230. 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 | $2,195 |
| Shaker Glen Village | Elm | $2,395 |
| Tudor Glen Village | The Birch | $2,495 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
Read Article
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.
Read ArticleDon'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 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
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
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.
Let everyone know!
Do you know the Winchester area?
If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, MA Rentals by Map
See the most popular apartments and homes in Winchester, MA
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 Leisure Lane Apartments listed at $2,195.
How much is the average rent for a 2 Bedroom Winchester Apartment?
The average rent for a 2 Bedroom Apartment in Winchester is $3,230.
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 1,888 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.
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.