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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
Pet Friendly Luxury Apartments for Rent in Winchester, MA (97 Rentals) Page 2 of 2
Pet Friendly Winchester Rentals.
Higher End Luxurious Apartments in Winchester.
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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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$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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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal 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
120 Jerome St
120 Jerome StMedford, MA 02155
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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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$2,950
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$2,950
Total Monthly Price
$2,950
50 Hamilton St, Unit 2
50 Hamilton StMedford, MA 02155
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$4,200
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available Jun 1, 2026Total Monthly Price
Base Rent
$4,200
Total Monthly Price
$4,200
303 Boston Ave, Unit 3
303 Boston 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 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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$3,000
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 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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$3,300
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
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 NowTotal 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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$3,100
Total Monthly Price12 Month Lease Term
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$3,100
Total Monthly Price
$3,100
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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$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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$3,900
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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$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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$3,000
Total Monthly Price12 Month Lease Term
3 Bedroom Apartment Available NowTotal 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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$3,000
Plus Fees
2 Bedroom Apartments Available Now26-28-28 Howard St
26-28-28 Howard StArlington, MA 02476
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$3,200
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Now110 Sharon St
110 Sharon StMedford, MA 02155
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$4,200
Plus Fees12 Month Lease Term
3 Bedroom Apartments Available Jun 1, 2026301-303 Boston Ave Unit #3
301-303 Boston AveMedford, MA 02155
224 Park St
StonehamMA02180
5 Curve St
LexingtonMA02420
26-28-28 Howard St
ArlingtonMA02476
1 Old Colony Ln
ArlingtonMA02476
67 Fairfax St
SomervilleMA02144
60 Auburn St
MedfordMA02155
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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 | $2,150 | $1,650 | $2,871 |
| Winchester 1 Bedroom Apartments | $2,599 | $1,295 | $4,195 |
| Winchester 2 Bedroom Apartments | $3,202 | $2,100 | $4,880 |
| Winchester 3 Bedroom Apartments | $3,638 | $2,500 | $6,900 |
| Winchester 4 Bedroom Apartments | $4,312 | $1,000 | $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.
Explore 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 195 Forest St listed at $1,000.
How much is the average rent for a Pet Friendly Winchester Apartment?
The average rent for a Pet Friendly Apartment in Winchester is $3,580.
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 2,767 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
Written by: Amelia Ramstead
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.