270 Cross St
WinchesterMA01890
4 Bedroom Homes for Rent in Winchester, MA (51 Rentals)
488 Washington St
WinchesterMA01890
46 Loring Ave
WinchesterMA01890
18 Grant Rd
WinchesterMA01890
59 Wedgemere Ave
WinchesterMA01890
280 Boston Ave
MedfordMA02155
30 Touro Ave, Unit 30
30 Touro Ave
MedfordMA02155
56 Gordon St, Unit 1
56 Gordon St
SomervilleMA02144
40 Campbell St
WoburnMA01801
6 Johnson St
WoburnMA01801
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.
8 Hamilton Rd
SomervilleMA02144
24 Oxford St, Unit 1
24 Oxford St
ArlingtonMA02474
14 Sturtevant Ter
MedfordMA02155
33 Raymond Ave, Unit 3
33 Raymond Ave
SomervilleMA02144
14 Kings Ct
ArlingtonMA02474
10 Greenleaf Ave, Unit 1
10 Greenleaf Ave
MedfordMA02155
217 Arlington St
MedfordMA02155
61 Wollaston Ave, Unit 61 Wollaston Ave - 2
61 Wollaston Ave
ArlingtonMA02476
11 Raymond Ave
SomervilleMA02144
2 Michael St
ArlingtonMA02474
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
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3 Day Cir
WoburnMA01801
15 Campbell Rd
ArlingtonMA02476
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$3,9954 Bedroom Apartments Available Sep 1
138 W Adams St
138 W Adams StSomerville, MA 02144
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$3,4004 Bedroom Apartments Available Sep 1
14 Allen St, Unit 2-3
14 Allen StArlington, MA 02474
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$4,0004 Bedroom Apartments Available Now
79 Harvard Ave, Unit 2
79 Harvard AveMedford, MA 02155
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$6,0004 Bedroom Apartments Available Aug 1
27 Emery St, Unit 1
27 Emery StMedford, MA 02155
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$4,5004 Bedroom Apartments Available Jun 1, 2027
100 W Adams St, Unit 2
100 W Adams StSomerville, MA 02144
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$5,6004 Bedroom Apartments Available Jun 1, 2027
18 Curtis Ave, Unit 1
18 Curtis AveSomerville, MA 02144
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$6,0004 Bedroom Apartments Available Jun 4, 2027
21 Sunset Rd, Unit 2
21 Sunset RdSomerville, MA 02144
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$5,7004 Bedroom Apartments Available Jun 1, 2027
15 Curtis Ave, Unit 1
15 Curtis AveSomerville, MA 02144
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.
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$4,5004 Bedroom Apartments Available Sep 1
27 Fairfax St, Unit 2
27 Fairfax StSomerville, MA 02144
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$4,3504 Bedroom Apartments Available Sep 1
27 Fairfax St, Unit 1
27 Fairfax StSomerville, MA 02144
33 Raymond Ave, Unit 2
33 Raymond Ave
SomervilleMA02144
33 Raymond Ave, Unit 3
33 Raymond Ave
SomervilleMA02144
533-535-535 Main St
StonehamMA02180
33 Brookings St
MedfordMA02155
14 Hamilton Rd
SomervilleMA02144
72 Cambridge Rd
WoburnMA01801
63 Summer St
MedfordMA02155
15 Governor Rd
ArlingtonMA02474
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & 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.
14 Kings Ct
ArlingtonMA02474
34 Linden St
BrooklineMA02445
30 Peacock Farm Rd
LexingtonMA02421
61 Warren St
MedfordMA02155
455 Summer St
ArlingtonMA02474
18 Winchester Dr
LexingtonMA02420
82 Arlmont St
ArlingtonMA02476
322 Lowell St
LexingtonMA02420
15 Campbell Rd
ArlingtonMA02476
76 Canal St
MedfordMA02155
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 | $3,079 | $2,400 | $4,250 |
| Winchester 3 Bedroom Homes for Rent | $4,136 | $3,000 | $6,800 |
| Winchester 4 Bedroom Homes for Rent | $5,612 | $3,475 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $9,199 | $5,000 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,941 | $6,495 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Top Homes for Rent in Winchester
Explore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
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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.
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Top 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.
Read ArticleQuick 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 399 Apartments for Rent in Winchester, MA with pricing that ranges from $1,650 to $20,951. There are also 263 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $985 to $20,000.
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 $985 to $20,000 with an average monthly rent of $5,008.
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 $2,600 to $5,994, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,800. Four Bedroom Single-Family rentals are also available starting from $3,475 and Four Bedroom Apartments start at $3,300.
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.
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Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
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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.
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For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.