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Rent Specials
$3,572 - $4,087
Total Monthly Price
Base Rent$2,344 - $7,168
Total Monthly PriceVaries
Sanctuary Winchester West
416 Cambridge StWinchester, MA 01890
2 Bedroom Apartments for Rent in Winchester, MA (172 Rentals)
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Rent Specials
$3,740 - $4,592
Total Monthly Price
Base Rent$2,835 - $8,880
Total Monthly PriceVaries
Sanctuary Winchester North
25-35 River StWinchester, MA 01890
24 Lebanon St
WinchesterMA01890
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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 Bedroom Apartments
40 Elmwood Ave
40 Elmwood AveWinchester, MA 01890
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Rent Specials
$2,800 - $3,273
Total Monthly Price
Base Rent$2,485 - $3,603
Total Monthly Price$2,485 - $3,603
Washington Crossing Apartments
55 Cedar StWoburn, MA 01801
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Rent Specials
$3,591 - $4,218
Total Monthly Price
Base Rent$2,418 - $6,306
Total Monthly PriceVaries
The Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
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$3,535 - $3,675
Total Monthly Price
Base Rent$2,641 - $4,716
Total Monthly PriceVaries
Brigham Square Apartments
30 Mill StArlington, MA 02476
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Rent Specials
$3,981 - $5,401
Total Monthly Price
Base Rent$2,567 - $6,718
Total Monthly Price$2,567 - $6,718
Hanover Stoneham
95 Maple StStoneham, MA 02180
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Rent Specials
$2,750 - $2,900
Total Monthly Price
Base Rent$2,450 - $2,900
Total Monthly Price$2,450 - $2,900
Glenbrook Estates
200 Bedford RdWoburn, MA 01801
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Rent Specials
$3,730 - $4,250
Total Monthly Price
Base Rent$2,475 - $4,485
Total Monthly PriceVaries
The Artemis at Arlington Heights
1163 Massachusetts AveArlington, MA 02476
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Rent Specials
$3,325 - $4,930
Total Monthly Price
Base Rent$2,640 - $4,930
Total Monthly PriceVaries
The Mave
225 Fallon RdStoneham, MA 02180
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$4,995 - $5,095
Total Monthly Price
Base Rent$4,995 - $5,295
Total Monthly Price$4,995 - $5,295
Townhomes at 285
285 Locust StWoburn, MA 01801
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$2,695 - $3,295
Total Monthly Price
Base Rent$2,195 - $3,295
Total Monthly Price$2,195 - $3,295
Tudor Glen Village
111 Locust StWoburn, MA 01801
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Rent Specials
$2,950 - $3,350
Total Monthly Price
Base Rent$2,500 - $3,350
Total Monthly PriceVaries
Stonehill Towers
5 Stonehill DrStoneham, MA 02180
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$3,700 - $4,100
Total Monthly Price
Base Rent$2,700 - $4,100
Total Monthly PriceVaries
The Legacy at Arlington Center
438 Massachusetts AveArlington, MA 02474
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$2,400 - $3,075
Total Monthly Price
Base Rent$2,400 - $3,075
Total Monthly Price$2,400 - $3,075
Mill Street Heights
59 Mill StWoburn, MA 01801
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$2,700
Total Monthly Price
Base Rent$1,775 - $2,900
Total Monthly Price$1,775 - $2,900
HCA - 840-846 Mass Ave
840 Massachusetts AveArlington, MA 02476
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$3,100
Total Monthly Price
Base Rent$3,100
Total Monthly Price$3,100
69 Raymond Ave
69 Raymond AveSomerville, MA 02144
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$2,500
Total Monthly Price
Base Rent$2,100 - $2,500
Total Monthly Price$2,100 - $2,500
Old Colony Apartments
1-17 Old Colony LnArlington, MA 02476
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Rent Specials
$2,250 - $2,600
Total Monthly Price
Base Rent$1,950 - $2,600
Total Monthly Price$1,950 - $2,600
Mill Street Gardens
57 Mill StWoburn, MA 01801
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$3,350
Total Monthly Price
Base Rent$3,350
Total Monthly Price$3,350
Pomeworth Corner
22 Pomeworth StStoneham, MA 02180
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Rent Specials
$2,200 - $2,550
Total Monthly Price
Base Rent$1,900 - $2,550
Total Monthly Price$1,900 - $2,550
Brattle Drive Apartments
0-12 Brattle DrArlington, MA 02474
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$2,255 - $2,585
Total Monthly Price
Base Rent$1,810 - $2,585
Total Monthly Price$1,810 - $2,585
Leisure Lane Apartments
100 Leisure LnStoneham, MA 02180
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$4,189 - $4,579
Total Monthly Price
Base Rent$2,812 - $8,675
Total Monthly PriceVaries
Arlington 360
4105 Symmes CirArlington, MA 02474
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$3,150
Total Monthly Price
Base Rent$3,150
Total Monthly Price$3,150
48 Pleasant Street
48 Pleasant StStoneham, MA 02180
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$3,200 - $3,400
Total Monthly Price
Base Rent$3,200 - $3,400
Total Monthly Price$3,200 - $3,400
79 Montvale Ave
79 Montvale AveWoburn, MA 01801
What It Really Costs to Live in Boston: A Local Renter’s Guide
Thinking of moving to Boston? Discover the real cost of living in the city. Our local expert guide breaks down rent, hidden utility costs, transportation tips, and neighborhood tradeoffs to help you budget smarter.
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$2,395
Total Monthly Price
Base Rent$2,395
Total Monthly Price$2,395
32 Pond St, Unit 2
32 Pond StStoneham, MA 02180
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$2,950
Total Monthly Price
Base Rent$2,950
Total Monthly Price$2,950
754 Massachusetts Ave, Unit 754 Massachusetts Ave
754 Massachusetts AveLexington, MA 02420
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$3,000
Total Monthly Price
Base Rent$3,000
Total Monthly Price$3,000
101 North St
101 North StSomerville, MA 02144
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$3,000
Total Monthly Price
Base Rent$3,000
Total Monthly Price$3,000
60 Summit St, Unit 60
60 Summit StArlington, MA 02474
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$2,600
Total Monthly Price
Base Rent$2,600
Total Monthly Price$2,600
42 Hilton St, Unit 1st Floor
42 Hilton StArlington, MA 02474
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$1,100
Total Monthly Price
Base Rent$1,100
Total Monthly Price$1,100
24 Paul Revere Rd, Unit 2
24 Paul Revere RdArlington, MA 02476
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$2,995
Total 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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$2,450
Total Monthly Price
Base Rent$2,450
Total Monthly Price$2,450
25 Arlington Rd, Unit Apt #3 6
25 Arlington RdWoburn, MA 01801
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$2,375
Total Monthly Price
Base Rent$2,375
Total Monthly Price$2,375
48 Nashua St, Unit 2
48 Nashua StWoburn, MA 01801
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$3,000
Total Monthly Price
Base Rent$3,000
Total Monthly Price$3,000
132 W Adams St, Unit 132
132 W Adams StSomerville, MA 02144
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Find your perfect apartment outside Boston. We review Quincy, Braintree, Malden, Somerville, and Lynn, covering local hotspots, commute options, and available rental types.
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$3,200
Total Monthly Price
Base Rent$3,200
Total Monthly Price$3,200
85 Boston Ave, Unit 1
85 Boston AveMedford, MA 02155
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$3,400
Total Monthly Price
Base Rent$3,400
Total Monthly Price$3,400
75 Conwell Ave, Unit 76 Conwell Ave
75 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price
Base Rent$3,300
Total Monthly Price$3,300
47 Curtis Ave, Unit 1
47 Curtis AveSomerville, MA 02144
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$2,500
Total Monthly Price
Base Rent$2,500
Total Monthly Price$2,500
14 Irvington Rd, Unit 1
14 Irvington RdSomerville, MA 02144
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$3,195
Total Monthly Price
Base Rent$3,195
Total Monthly Price$3,195
97 W Quincy St, Unit 1
97 W Quincy StSomerville, MA 02144
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$2,500
Total Monthly Price
Base Rent$2,500
Total Monthly Price$2,500
60 Adams St, Unit 2
60 Adams StMedford, MA 02155
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$3,200
Total 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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$2,200
Total Monthly Price
Base Rent$2,200 - $3,800
Total Monthly Price$2,200 - $3,800
369 Boston Ave
369 Boston AveMedford, MA 02155
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$2,900
Total Monthly Price
Base Rent$2,900
Total Monthly Price$2,900
35 Whitfield Rd, Unit #3
35 Whitfield RdSomerville, MA 02144
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$3,000
Total Monthly Price
Base Rent$3,000
Total Monthly Price$3,000
69 Conwell Ave
69 Conwell AveSomerville, MA 02144
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Looking for the perfect new rental? Learn great ways to spot the perfect apartment for you, identify common red flags, and avoid rental issues and scams with these expert provided actionable tips.
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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 | $2,393 | $1,750 | $3,360 |
| Winchester 1 Bedroom Apartments | $2,648 | $825 | $4,305 |
Winchester 2 Bedroom Apartments | $3,301 | $1,100 | $5,575 |
| Winchester 3 Bedroom Apartments | $3,812 | $2,500 | $6,854 |
| Winchester 4 Bedroom Apartments | $4,668 | $2,900 | $6,750 |
| Winchester 5 Bedroom Apartments | $6,972 | $4,350 | $10,000+ |
| Winchester 6 Bedroom Apartments | $7,696 | $6,300 | $9,600 |
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
- Nearby Cities
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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 $3,195. Hanover Stoneham in the Wyoming neighborhood has the second largest 2 Bedroom, which is sized at 1,322 square feet and currently listed start at $4,652. 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 | $3,195 |
| Hanover Stoneham | M | 1,322 Sq Ft | $4,652 |
| Sanctuary Winchester North | 2K Den | 1,288 Sq Ft | $4,345 |
| Sanctuary Winchester West | B6 Den | 1,260 Sq Ft | $3,572 |
| Washington Crossing Apartments | Clarendon 2B2B | 1,200 Sq Ft | $2,900 |
| 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 | $3,591 |
| 48 Pleasant Street | 2BR/1.5BA | 1,061 Sq Ft | $3,150 |
| Brigham Square Apartments | Moxie | 1,059 Sq Ft | $3,535 |
| Shaker Glen Village | Dogwood | 875 Sq Ft | $2,795 |
Cheapest Available Winchester 2 Bedroom Apartments
As of September 11, 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 B1 Model at Brookside Apartments starting at $2,300 in the Turning Mill neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $3,301. 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 |
| Brookside Apartments | B1 | $2,300 |
| 30 Pomeworth Street | 2BR/1.0BA | $2,495 |
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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Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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 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 $3,301.
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 $3,195 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 1,513 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
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Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
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Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
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Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
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