128 Monument St, Unit 126
128 Monument St
MedfordMA02155
Pet Friendly Homes for Rent in Winchester, MA (117 Rentals) Page 2 of 3
Homes for rent in Winchester that love your dogs or cats as much as you do!
120 Jerome St
MedfordMA02155
120 Jerome St
MedfordMA02155
120 Jerome St
MedfordMA02155
232 Fulton St, Unit T
232 Fulton St
MedfordMA02155
120 Jerome St, Unit 120
120 Jerome St
MedfordMA02155
232 Fulton St, Unit 232
232 Fulton St
MedfordMA02155
19 Shirley Rd
MedfordMA02155
5 Curve St
LexingtonMA02420
24 Tyler Rd
LexingtonMA02420
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
162 E Emerson Rd
LexingtonMA02420
67 Fairfax St, Unit 1
67 Fairfax St
SomervilleMA02144
139 Hillsdale Rd, Unit 2
139 Hillsdale Rd
SomervilleMA02144
94 North St, Unit 1
94 North St
SomervilleMA02144
94 North St
SomervilleMA02144
94 North St
SomervilleMA02144
56 Gordon St, Unit 1
56 Gordon St
SomervilleMA02144
1 Victoria St, Unit 1A
1 Victoria St
SomervilleMA02144
14 Belknap St, Unit 3
14 Belknap St
SomervilleMA02144
14 Belknap St, Unit 3
14 Belknap St
SomervilleMA02144
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
269 Alewife Brook Pky, Unit 1
269 Alewife Brook Pky
SomervilleMA02144
1 Victoria St, Unit 1A
1 Victoria St
SomervilleMA02144
39 Belknap St, Unit 2
39 Belknap St
SomervilleMA02144
32 Irvington Rd
SomervilleMA02144
94 North St, Unit 94
94 North St
SomervilleMA02144
2 High St, Unit 1
2 High St
SomervilleMA02144
56 Gordon St, Unit 2
56 Gordon St
SomervilleMA02144
32 Irvington Rd
SomervilleMA02144
1 Victoria St, Unit 2
1 Victoria St
SomervilleMA02144
1 Victoria St, Unit 2
1 Victoria St
SomervilleMA02144
190 North St, Unit 2
190 North St
SomervilleMA02144
50 Curtis Ave, Unit 1
50 Curtis Ave
SomervilleMA02144
14 Barton St, Unit 2
14 Barton St
SomervilleMA02144
2 Osgood St, Unit 1
2 Osgood St
SomervilleMA02143
77 North St
SomervilleMA02144
64 Chetwynd Rd, Unit 1
64 Chetwynd Rd
SomervilleMA02144
301 Alewife Brook Pky, Unit 301
301 Alewife Brook Pky
SomervilleMA02144
301 Alewife Brook Pky
SomervilleMA02144
3 Hamilton Rd, Unit 2
3 Hamilton Rd
SomervilleMA02144
24 Chetwynd Rd, Unit 2
24 Chetwynd Rd
SomervilleMA02144
4 High St, Unit 1
4 High St
SomervilleMA02144
3 Hamilton Rd, Unit 2
3 Hamilton Rd
SomervilleMA02144
5 Hamilton Rd, Unit 2
5 Hamilton Rd
SomervilleMA02144
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$3,000
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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
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3 Bedroom Apartments Available Jun 1, 2026301-303 Boston Ave Unit #3
301-303 Boston AveMedford, MA 02155
3 Day Cir
WoburnMA01801
11 Pinkham Rd
MedfordMA02155
49 Ripley Rd
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 a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,908 | $2,175 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,678 | $2,800 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $5,061 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,508 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,897 | $5,000 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $7,700 | $7,700 | $7,700 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 488 Apartments for Rent in Winchester, MA with pricing that ranges from $1,000 to $9,300. There are also 310 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,500 to $40,000.
What is the current price range for Rental Homes in Winchester?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $1,500 to $40,000 with an average monthly rent of $4,852.
How much are larger Three and Four Bedroom Rentals in Winchester?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,500 to $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $1,000.
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.