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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
Pet Friendly Apartments for Rent in Winchester, MA (157 Rentals) Page 2 of 4
Apartments for rent in Winchester that love your dogs or cats as much as you do!
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$2,800
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
26 Marshall St, Unit 1
26 Marshall StMedford, MA 02155
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
41 Belknap St, Unit 2
41 Belknap 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
66 North St
66 North StSomerville, MA 02144
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$3,400
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,400
Total Monthly Price
$3,400
12 Quincy St, Unit 1
12 Quincy StMedford, MA 02155
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$5,945
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,945
Total Monthly Price
$5,945
3 Hamilton Rd, Unit #2
3 Hamilton RdSomerville, MA 02144
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$3,100
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
44 Russell Rd, Unit 1
44 Russell RdSomerville, MA 02144
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$3,975
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,975
Total Monthly Price
$3,975
54 Upland Rd, Unit 2
54 Upland RdSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
86 Orchard St, Unit 1
86 Orchard StMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 2
5 Harris RdMedford, MA 02155
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$4,400
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,400
Total Monthly Price
$4,400
5 Harris Rd, Unit 2
5 Harris RdMedford, MA 02155
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$3,500
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
293 Boston Ave, Unit 2
293 Boston AveMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
86 Orchard St, Unit 3
86 Orchard StMedford, MA 02155
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$3,600
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,600
Total Monthly Price
$3,600
65 Conwell Ave
65 Conwell AveSomerville, MA 02144
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$6,200
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,200
Total Monthly Price
$6,200
3 Hamilton Rd, Unit #2
3 Hamilton RdSomerville, MA 02144
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$4,800
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,800
Total Monthly Price
$4,800
86 Orchard St, Unit 1
86 Orchard StMedford, MA 02155
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
224 Arlington St
224 Arlington StMedford, MA 02155
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$5,995
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,995
Total Monthly Price
$5,995
3 Hamilton Rd, Unit 2
3 Hamilton RdSomerville, MA 02144
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$6,995
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,995
Total Monthly Price
$6,995
128 Monument St
128 Monument StMedford, MA 02155
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$6,995
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$6,995
Total Monthly Price
$6,995
120 Jerome St
120 Jerome StMedford, MA 02155
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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$3,200
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available Jan 1, 2026Total 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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$3,300
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
1 Victoria St, Unit #1A
1 Victoria StSomerville, MA 02144
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$4,500
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,500
Total Monthly Price
$4,500
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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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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$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
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
50 Hamilton St, Unit 2
50 Hamilton StMedford, MA 02155
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$2,600
Total Monthly Price10 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,600
Total Monthly Price
$2,600
69 Raymond Ave, Unit 1
69 Raymond AveSomerville, MA 02144
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$5,800
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$5,800
Total Monthly Price
$5,800
303 Boston Ave, Unit 3
303 Boston 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
44 Greenleaf Ave, Unit 1
44 Greenleaf AveMedford, 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 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
Base Rent
$3,000
Total Monthly Price
$3,000
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
96 Conwell Ave, Unit 1
96 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
96 Conwell Ave, Unit 2
96 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
96 Conwell Ave, Unit 3
96 Conwell AveSomerville, MA 02144
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
96 Conwell Ave, Unit 2
96 Conwell AveSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
9 Irving St, Unit 1
9 Irving StMedford, MA 02155
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$2,800
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,800
Total Monthly Price
$2,800
9 Irving St, Unit 2
9 Irving StMedford, MA 02155
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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
79 Conwell Ave, Unit 2
79 Conwell AveSomerville, MA 02144
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$3,500
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,500
Total Monthly Price
$3,500
14 Belknap St, Unit 2
14 Belknap StSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
67 Orchard St, Unit 1
67 Orchard 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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$3,300
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$3,300
Total Monthly Price
$3,300
79 Conwell Ave, Unit 1
79 Conwell AveSomerville, MA 02144
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$4,900
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$4,900
Total Monthly Price
$4,900
1 Victoria St, Unit 2
1 Victoria StSomerville, MA 02144
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$3,900
Total Monthly Price12 Month Lease Term
4 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,900
Total Monthly Price
$3,900
56 Gordon St, Unit 1
56 Gordon StSomerville, MA 02144
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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Nov 1Total Monthly Price
Base Rent
$3,000
Total Monthly Price
$3,000
48 Chester Ave, Unit 1
48 Chester AveMedford, MA 02155
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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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$5,945
Total Monthly Price12 Month Lease Term
6 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$5,945
Total Monthly Price
$5,945
5 Hamilton Rd, Unit 1
5 Hamilton 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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$4,200
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Now86 Orchard St
86 Orchard StMedford, 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 Pet Friendly Studio Apartments | $2,171 | $1,200 | $2,829 |
| Winchester Pet Friendly 1 Bedroom Apartments | $2,649 | $1,395 | $4,195 |
| Winchester Pet Friendly 2 Bedroom Apartments | $3,203 | $2,195 | $5,999 |
| Winchester Pet Friendly 3 Bedroom Apartments | $3,704 | $2,500 | $6,900 |
| Winchester Pet Friendly 4 Bedroom Apartments | $4,542 | $3,000 | $8,000 |
| Winchester 5 Bedroom Apartments | $6,089 | $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
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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 Pet Friendly Winchester Apartments
What is the Cheapest Pet Friendly apartment in Winchester?
Currently the most affordable Pet Friendly Apartment in Winchester is at Brattle Drive Apartments listed at $1,800.
How much is the average rent for a Pet Friendly Winchester Apartment?
The average rent for a Pet Friendly Apartment in Winchester is $3,556.
What is the largest Pet Friendly Winchester Apartment for rent?
Today's Pet Friendly apartment with the most square footage in Winchester is a 9,999 square feet unit starting from $2,975 at 1 Victoria St, Unit 1A.
What is the average size for Winchester Pet Friendly Apartments for rent?
The average size for a Pet Friendly rental in Winchester is currently at 2,722 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.