60 Lake St
WinchesterMA01890
Pet Friendly Homes for Rent in Winchester, MA (64 Rentals)
Homes for rent in Winchester that love your dogs or cats as much as you do!
200 Swanton St
WinchesterMA01890
7 Ridge St
WinchesterMA01890
5 Quigley Ct
WinchesterMA01890
60 Lake St
WinchesterMA01890
79 Bacon St
WinchesterMA01890
40 Brattle St
ArlingtonMA02476
2 Albert Dr, Unit 10
2 Albert Dr
WoburnMA01801
159 Bedford Rd
WoburnMA01801
4 Senator Rd
WoburnMA01801
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Moving to Boston? Discover how to handle unique rental rules, avoid common moving day pitfalls, and prepare for your first winter in the city
3 Day Cir
WoburnMA01801
47 Mystic St, Unit 5A
47 Mystic St
ArlingtonMA02474
72 Harlow St, Unit 72
72 Harlow St
ArlingtonMA02474
15 Campbell Rd
ArlingtonMA02476
53 Oakland St, Unit TWO
53 Oakland St
MedfordMA02155
34 Salem St, Unit 201
34 Salem St
MedfordMA02155
116 Grove St
MedfordMA02155
177 Central St
StonehamMA02180
56 Gordon St, Unit 1
56 Gordon St
SomervilleMA02144
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$3,000Pet FriendlyCats Allowed
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76 Conwell Ave, Unit #3
76 Conwell AveSomerville, MA 02144
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
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$5,500Pet FriendlyCats Allowed
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69 Raymond Ave, Unit #3
69 Raymond AveSomerville, MA 02144
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$3,600Pet FriendlyCats Allowed
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65 Conwell Ave, Unit #2
65 Conwell AveSomerville, MA 02144
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$2,000Pet FriendlyCats Allowed
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167-169 Summer St #B, Unit #B
167-169 Summer StArlington, MA 02474
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$4,500Pet FriendlyDogs and Cats Allowed
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167-169 Summer St #1, Unit #1
167-169 Summer StArlington, MA 02474
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$2,625Pet FriendlyCats Allowed
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104 Conwell Ave, Unit #1
104 Conwell AveSomerville, MA 02144
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$5,500Pet FriendlyCats Allowed
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65 Conwell Ave, Unit #1
65 Conwell AveSomerville, MA 02144
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$3,200Pet FriendlyCats Allowed
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125 Allston St
125 Allston StMedford, MA 02155
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$6,000Pet FriendlyCats Allowed
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301-303 Boston Ave #2, Unit #2
301-303 Boston AveMedford, MA 02155
15 Governors Ave, Unit 22
15 Governors Ave
MedfordMA02155
89 Burget Ave, Unit 2
89 Burget Ave
MedfordMA02155
What It Really Costs to Live in Boston: A Local Renter’s Guide
Thinking of moving to Boston? Discover the real cost of living in the city. Our local expert guide breaks down rent, hidden utility costs, transportation tips, and neighborhood tradeoffs to help you budget smarter.
89 Burget Ave, Unit 2
89 Burget Ave
MedfordMA02155
15 Governors Ave, Unit 22
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 28
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 2
15 Governors Ave
MedfordMA02155
89 Burget Ave, Unit 2
89 Burget Ave
MedfordMA02155
89 Burget Ave, Unit 2
89 Burget Ave
MedfordMA02155
89 Burget Ave, Unit 2
89 Burget Ave
MedfordMA02155
89 Burget Ave, Unit 2
89 Burget Ave
MedfordMA02155
89 Burget Ave, Unit 2
89 Burget Ave
MedfordMA02155
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Find your perfect apartment outside Boston. We review Quincy, Braintree, Malden, Somerville, and Lynn, covering local hotspots, commute options, and available rental types.
77 Brookings St, Unit 2
77 Brookings St
MedfordMA02155
15 Governors Ave, Unit 22
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 28
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 2
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
102 Raymond Ave
SomervilleMA02144
74 Beach St
WoburnMA01801
555 Main St
WoburnMA01801
39 Harlow St
ArlingtonMA02474
15 Governor Rd
ArlingtonMA02474
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
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Winchester, MA Local Guide
How much does it cost to rent a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,996 | $1,000 | $4,750 |
| Winchester 3 Bedroom Homes for Rent | $3,844 | $2,900 | $6,000 |
| Winchester 4 Bedroom Homes for Rent | $5,066 | $3,450 | $8,750 |
| Winchester 5 Bedroom Homes for Rent | $7,976 | $4,000 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $10,450 | $7,500 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Winchester, MA Local Guide
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10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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Boston Neighborhood Guide: Living Near UMass, MGH, and State Street
Get the local scoop! ApartmentHomeLiving's Boston Expert reveals the best neighborhoods to rent for employees of UMass Boston, Mass General Hospital, State Street, and more.
Read ArticleNavigating 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.
Read ArticleTop Neighborhoods Near Boston Colleges and Universities
Learn About the Best Neighborhoods to Rent Near College Campuses in Boston, MA | Find Boston Off-Campus Student Housing at ApartmentHomeLiving.com
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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Quick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Winchester, MA Rentals by Map
See the most popular apartments and homes in Winchester, MA
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 440 Apartments for Rent in Winchester, MA with pricing that ranges from $825 to $12,539. There are also 280 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $795 to $18,000.
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 $795 to $18,000 with an average monthly rent of $3,905.
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 $7,312, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,450 and Four Bedroom Apartments start at $2,900.
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
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
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Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
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Articles, How-To's, and Tips
How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
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Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.