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$2,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Sep 15Total Monthly Price
Base Rent
$2,250
Total Monthly Price
$2,250
74 Beach St, Unit #3-3
74 Beach StWoburn, MA 01801
2 Bedroom Apartments for Rent in Winchester, MA (207 Rentals) Page 2 of 5
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$2,699
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$2,699
Total Monthly Price
$2,699
34 Park Avenue Ext, Unit 34
34 Park Avenue ExtArlington, MA 02474
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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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$2,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,400
Total Monthly Price
$2,400
129 Warren St, Unit 2
129 Warren StArlington, MA 02474
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$3,100
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
86 Orchard St, Unit 3
86 Orchard StMedford, MA 02155
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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
42 Summer St, Unit 42 Summer Street
42 Summer StMedford, MA 02155
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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
53 Oakland St
53 Oakland StMedford, MA 02155
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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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$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
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$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
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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
67 Greenleaf Ave, Unit 1
67 Greenleaf AveMedford, MA 02155
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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
33 Irvington Rd
33 Irvington RdSomerville, MA 02144
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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
136 Sharon St
136 Sharon StMedford, MA 02155
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$3,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,600
Total Monthly Price
$3,600
235 Ashcroft Rd, Unit 235 Ashcroft St
235 Ashcroft RdMedford, MA 02155
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$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
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$4,300
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,300
Total Monthly Price
$4,300
63 Fairfax St, Unit 2
63 Fairfax StSomerville, MA 02144
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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
27 Holton St, Unit 1
27 Holton StMedford, 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
66 North St
66 North StSomerville, MA 02144
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$3,325
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,325
Total Monthly Price
$3,325
235 Ashcroft Rd, Unit 1
235 Ashcroft RdMedford, MA 02155
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$3,300
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
269 Alewife Brook Pky, Unit 1
269 Alewife Brook PkySomerville, MA 02144
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$2,900
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$2,900
Total Monthly Price
$2,900
8 Madison St, Unit 1
8 Madison StMedford, MA 02155
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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
340 High St, Unit 1
340 High StMedford, MA 02155
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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
27 Holton St, Unit 1
27 Holton StMedford, MA 02155
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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
153 W Adams St, Unit 2
153 W Adams StSomerville, MA 02144
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$3,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
1 Victoria St, Unit 1
1 Victoria StSomerville, 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
60 Hamilton St, Unit 1
60 Hamilton StMedford, MA 02155
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$2,650
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,650
Total Monthly Price
$2,650
80 Orchard St, Unit Apt 1
80 Orchard StMedford, 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
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
Base Rent
$2,600
Total Monthly Price
$2,600
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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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
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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
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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
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 Oct 1Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
26 Bradlee Rd, Unit 406
26 Bradlee RdMedford, MA 02155
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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Oct 1Total Monthly Price
Base Rent
$3,200
Total Monthly Price
$3,200
26 Bradlee Rd, Unit 302
26 Bradlee RdMedford, MA 02155
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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
26 Adams St, Unit 3
26 Adams StMedford, MA 02155
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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
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$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
Base Rent
$3,000
Total Monthly Price
$3,000
29 Capen St
29 Capen StMedford, 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
29 Capen St
29 Capen StMedford, 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
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
Base Rent
$3,000
Total Monthly Price
$3,000
1 Victoria St, Unit #1A
1 Victoria StSomerville, MA 02144
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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
29 Capen St, Unit 2
29 Capen StMedford, MA 02155
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$3,400
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
1 Victoria St, Unit 1A
1 Victoria StSomerville, MA 02144
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$3,250
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,250
Total Monthly Price
$3,250
22 Bradlee Rd, Unit 405
22 Bradlee RdMedford, MA 02155
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$2,690
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,690
Total Monthly Price
$2,690
79 Capen St, Unit 1
79 Capen 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
69 Raymond Ave, Unit 1R
69 Raymond AveSomerville, MA 02144
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$2,600
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
37 Pearl St, Unit 1st floor apt near Tufts
37 Pearl StMedford, 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
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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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
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 NowTotal Monthly Price
Base Rent
$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
Base Rent
$3,000
Total Monthly Price
$3,000
96 Conwell Ave, Unit 2
96 Conwell AveSomerville, MA 02144
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$3,325
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,325
Total Monthly Price
$3,325
235 Ashcroft Rd, Unit 1
235 Ashcroft RdMedford, MA 02155
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
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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.
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.
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.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
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.