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$2,350
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$2,350
Total Monthly Price
$2,350
14 Cotting St, Unit 3
14 Cotting StMedford, MA 02155
2 Bedroom Apartments for Rent in Winchester, MA (172 Rentals) Page 2 of 4
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$3,500
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$3,500
Total Monthly Price
$3,500
235 Ashcroft Rd
235 Ashcroft RdMedford, MA 02155
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$2,750
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$2,750
Total Monthly Price
$2,750
27 Holton St, Unit 1
27 Holton StMedford, MA 02155
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$2,700
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$2,700
Total Monthly Price
$2,700
8 Madison St, Unit 1
8 Madison StMedford, MA 02155
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$2,700
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2 Bedroom Apartment Available NowTotal Monthly Price
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$2,700
Total Monthly Price
$2,700
340 High St, Unit 1
340 High StMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$3,000
Total Monthly Price
$3,000
29 Capen St, Unit #2
29 Capen StMedford, MA 02155
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$2,600
Total Monthly Price
$2,600
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jan 1, 2026Total Monthly Price
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$3,200
Total Monthly Price
$3,200
26 Bradlee Rd, Unit 406
26 Bradlee RdMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$3,000
Total Monthly Price
$3,000
29 Capen St
29 Capen StMedford, MA 02155
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$3,000
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2 Bedroom Apartment Available NowTotal Monthly Price
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$3,000
Total Monthly Price
$3,000
29 Capen St
29 Capen StMedford, MA 02155
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.
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$3,300
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$3,300
Total Monthly Price
$3,300
77 Fairfax St, Unit #1
77 Fairfax StSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$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
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$3,000
Total Monthly Price
$3,000
1 Victoria St, Unit #1A
1 Victoria StSomerville, MA 02144
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$2,690
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2 Bedroom Apartment Available NowTotal Monthly Price
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$2,690
Total Monthly Price
$2,690
79 Capen St, Unit 1
79 Capen StMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$3,000
Total Monthly Price
$3,000
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$3,000
Total Monthly Price
$3,000
186 Powder House Blvd, Unit 2
186 Powder House BlvdSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$3,000
Total Monthly Price
$3,000
96 Conwell Ave, Unit 2
96 Conwell AveSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$3,000
Total Monthly Price
$3,000
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
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$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 NowTotal Monthly Price
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$3,100
Total Monthly Price
$3,100
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
Navigating the Rental Market: Tips for First-Time Renters
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$2,975
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,975
Total Monthly Price
$2,975
1 Victoria St, Unit 1A
1 Victoria StSomerville, MA 02144
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$3,000
Plus Fees
2 Bedroom Apartments Available Now26-28-28 Howard St
26-28-28 Howard StArlington, MA 02476
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$3,100
Plus Fees
2 Bedroom Apartments Available Now385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
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$3,000
Plus Fees
2 Bedroom Apartments Available Now186 Powder House Blvd
186 Powder House BlvdSomerville, MA 02144
269 Cambridge Rd
WoburnMA01801
88 Quincy St
MedfordMA02155
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
1 Stonehill Dr
StonehamMA02180
932 Massachusetts Ave
ArlingtonMA02476
224 Park St
StonehamMA02180
5 Curve St
LexingtonMA02420
26 Howard St
ArlingtonMA02476
29 Garfield Ave
WoburnMA01801
1 Old Colony Ln
ArlingtonMA02476
28 Cornell St
ArlingtonMA02474
66 Auburn St
MedfordMA02155
69 Raymond Ave
SomervilleMA02144
63 Bow St
ArlingtonMA02474
25 Laurel St
ArlingtonMA02476
390 Fellsway W
MedfordMA02155
23 Wellington St
ArlingtonMA02476
64 Freeman St
ArlingtonMA02474
274 Boston
MedfordMA02155
192 Brookside Pkwy
MedfordMA02155
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MedfordMA02155
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MedfordMA02155
42 Irving St
MedfordMA02155
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 | $2,154 | $1,650 | $2,871 |
| Winchester 1 Bedroom Apartments | $2,610 | $1,295 | $4,195 |
Winchester 2 Bedroom Apartments | $3,208 | $2,100 | $4,880 |
| Winchester 3 Bedroom Apartments | $3,646 | $2,500 | $6,900 |
| Winchester 4 Bedroom Apartments | $4,361 | $1,150 | $6,375 |
| Winchester 5 Bedroom Apartments | $6,259 | $4,500 | $9,300 |
| Winchester 6 Bedroom Apartments | $7,261 | $5,945 | $8,437 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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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 $3,208.
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 1,812 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
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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.
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.