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Rent Specials
$3,485 - $4,342
Plus Fees
2 Bedroom Apartments Available NowSanctuary Winchester West
416 Cambridge StWinchester, MA 01890
2 Bedroom Apartments for Rent in Winchester, MA (207 Rentals)
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Rent Specials
$3,482 - $4,720
Plus Fees
2 Bedroom Apartments Available NowSanctuary Winchester North
25-35 River StWinchester, MA 01890
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$2,695
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,695
Total Monthly Price
$2,695
6 Skillings Rd, Unit #2-J
6 Skillings RdWinchester, MA 01890
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$2,695
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,695
Total Monthly Price
$2,695
6 Skillings Rd, Unit 2
6 Skillings RdWinchester, MA 01890
343 Washington St
WinchesterMA01890
35 Vine St
WinchesterMA01890
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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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$2,911 - $3,166
Plus Fees
2 Bedroom Apartments Available NowWashington Crossing Apartments
55 Cedar StWoburn, MA 01801
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Rent Specials
$3,172 - $3,943
Plus Fees
2 Bedroom Apartments Available NowThe Devon at Weiss Farm
168 Franklin StStoneham, MA 02180
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Rent Specials
$3,529 - $4,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,252 - $4,925
Total Monthly Price
$2,252 - $4,925
The Artemis at Arlington Heights
1163 Massachusetts AveArlington, MA 02476
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$3,310 - $5,050
Total Monthly Price1 Month Lease Term
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$2,745 - $5,050
Total Monthly Price
$2,745 - $5,050
The Mave
225 Fallon RdStoneham, MA 02180
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$3,541
Plus Fees
2 Bedroom Apartments Available NowBrigham Square Apartments
30 Mill StArlington, MA 02476
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Rent Specials
$2,714 - $5,128
Plus Fees
2 Bedroom Apartments Available NowHanover Stoneham
95 Maple StStoneham, MA 02180
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$3,095 - $3,295
Plus Fees
2 Bedroom Apartments Available NowTudor Glen Village
111 Locust StWoburn, MA 01801
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Rent Specials
$2,800 - $3,200
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowStonehill Towers
5 Stonehill DrStoneham, MA 02180
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$3,750 - $4,100
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowThe Legacy at Arlington Center
438 Massachusetts AveArlington, MA 02474
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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$3,695 - $3,809
Total Monthly Price
2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$3,060 - $6,857
Total Monthly Price
$3,060 - $6,857
Arlington 360
4105 Symmes CirArlington, MA 02474
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Rent Specials
$2,250 - $2,350
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowMill Street Gardens
57 Mill StWoburn, MA 01801
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$2,195 - $2,525
Plus Fees12 Month Lease Term
2 Bedroom Apartments Available NowLeisure Lane Apartments
100 Leisure LnStoneham, MA 02180
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$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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$2,300
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,300
Total Monthly Price
$2,300
27 North St, Unit 3B
27 North StStoneham, MA 02180
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$2,200
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 Sep 20Total 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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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
110 W Quincy St, Unit 2
110 W Quincy StSomerville, MA 02144
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$3,150
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total 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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$2,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,200
Total Monthly Price
$2,200
505 Main St, Unit 3
505 Main StStoneham, MA 02180
The 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.
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$2,300
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,300
Total Monthly Price
$2,300
132 Madison Ave, Unit 132
132 Madison AveArlington, MA 02474
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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 15Total Monthly Price
Base Rent
$2,700
Total Monthly Price
$2,700
1 Boline Pl, Unit 1 Boline Place
1 Boline PlWoburn, MA 01801
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$3,500
Total Monthly Price9 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
44 Winter St, Unit 1
44 Winter StMedford, MA 02155
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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
60 Hamilton St
60 Hamilton StMedford, MA 02155
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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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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 3Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
2 Clark St, Unit 2
2 Clark StWoburn, 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
52 Mt Vernon St, Unit 1
52 Mt Vernon StArlington, MA 02476
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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.
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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
8 Usher Rd, Unit 1
8 Usher RdMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Mar 1, 2026Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
321 Alewife Brook Pky, Unit 1
321 Alewife Brook PkySomerville, MA 02144
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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 Rawson Rd, Unit 1
28 Rawson 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
110 W Quincy St, Unit #1
110 W Quincy StSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 15Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
50 Marion Rd, Unit 1
50 Marion RdArlington, MA 02474
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$3,295
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,295
Total Monthly Price
$3,295
52 Mt Vernon St, Unit 1
52 Mt Vernon StArlington, MA 02476
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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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$2,875
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,875
Total Monthly Price
$2,875
15 Pond Ln, Unit #26
15 Pond LnArlington, MA 02474
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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
6 Gloucester St
6 Gloucester StArlington, MA 02476
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$2,300
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,300
Total Monthly Price
$2,300
56 Campbell St, Unit 56R
56 Campbell StWoburn, MA 01801
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$2,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
22 Scott St, Unit 1
22 Scott StWoburn, MA 01801
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$2,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
22 Scott St, Unit 1
22 Scott 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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$2,800
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
109 Westmoreland Ave, Unit 109 Westmoreland Ave
109 Westmoreland AveArlington, MA 02474
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 | $2,271 | $1,550 | $2,914 |
| Winchester 1 Bedroom Apartments | $2,815 | $1,850 | $4,350 |
Winchester 2 Bedroom Apartments | $3,234 | $2,195 | $5,128 |
| Winchester 3 Bedroom Apartments | $3,701 | $2,250 | $7,500 |
| Winchester 4 Bedroom Apartments | $4,654 | $3,200 | $6,066 |
| Winchester 5 Bedroom Apartments | $5,988 | $4,000 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,262 | $5,945 | $9,100 |
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 September 14, 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 2 Bedroom Model at Arlington Gardens Apartments starting at $2,200 in the East Arlington neighborhood. The average price for all 2 Bedroom apartments in Winchester is currently $3,234. 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 |
| Arlington Gardens Apartments | 2 Bedroom | $2,200 |
| Mill Street Gardens | 2 Bedroom | $2,250 |
| Medford Square Riverside | B1M | $2,300 |
| Brookside Apartments | B1 | $2,350 |
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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 $3,234.
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 2,169 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.
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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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
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Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.