270 Cross St
WinchesterMA01890
Homes for Rent in Winchester, MA with Hardwood Floors (68 Rentals)
161 Highland Ave
WinchesterMA01890
74 Sharon St
MedfordMA02155
555 Main St
WoburnMA01801
4 Arizona Ter, Unit 5
4 Arizona Ter
ArlingtonMA02474
34 Hamilton Rd, Unit 206
34 Hamilton Rd
ArlingtonMA02474
1033 Massachusetts Ave, Unit 10
1033 Massachusetts Ave
ArlingtonMA02476
3 Colonial Village Dr, Unit 10
3 Colonial Village Dr
ArlingtonMA02474
4 Park St, Unit 1
4 Park St
ArlingtonMA02474
61 Wollaston Ave, Unit 61 Wollaston Ave - 2
61 Wollaston Ave
ArlingtonMA02476
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.
15 Campbell Rd
ArlingtonMA02476
50 Water St, Unit 76
50 Water St
MedfordMA02155
21 Royall St, Unit 3B1B on 2nd FL
21 Royall St
MedfordMA02155
112 College Ave, Unit 1##
112 College Ave
MedfordMA02155
34 Hume Ave, Unit 2
34 Hume Ave
MedfordMA02155
217 Arlington St
MedfordMA02155
479 Fulton St
MedfordMA02155
120 Jerome St, Unit 1
120 Jerome St
MedfordMA02155
230 Fulton St
MedfordMA02155
140 Jerome St
MedfordMA02155
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.
64 Newcomb Rd
StonehamMA02180
14 Massachusetts Ave
LexingtonMA02420
14 Irvington Rd, Unit 14 Irvington Road
14 Irvington Rd
SomervilleMA02144
14 Hamilton Rd, Unit 1a
14 Hamilton Rd
SomervilleMA02144
3 Hamilton Rd
SomervilleMA02144
62 Woods Ave, Unit 2##
62 Woods Ave
SomervilleMA02144
8 Hamilton Rd
SomervilleMA02144
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$7,0005 Bedroom Apartments Available Now
14 Sturtevant Terrace, Unit 1
14 Sturtevant TerraceMedford, MA 02155
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$5,4976 Bedroom Apartments Available Now
36 Gould St
36 Gould StStoneham, MA 02180
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$2,6002 Bedroom Apartments Available Now
66 Mill St, Unit 8
66 Mill StWoburn, MA 01801
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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$2,5002 Bedroom Apartments Available Now
50 Mill St, Unit 5
50 Mill StWoburn, MA 01801
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$2,7501 Bedroom Apartments Available Now
32 Walnut St
32 Walnut StArlington, MA 02476
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$4,0003 Bedroom Apartments Available Sep 1
53 Oakland St, Unit #2
53 Oakland StMedford, MA 02155
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$2,381Studio Apartments Available Now
30 Mill St, Unit Menotomy layout
30 Mill StArlington, MA 02476
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$6,3007 Bedroom Apartments Available Sep 15
15 Bartlett Ave, Unit TH
15 Bartlett AveArlington, MA 02476
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$2,9002 Bedroom Apartments Available Now
92 Sylvia St
92 Sylvia StArlington, MA 02474
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$3,2002 Bedroom Apartments Available Aug 15
2500 Mystic Valley Pkwy, Unit #805
2500 Mystic Valley PkwyMedford, MA 02155
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$2,5002 Bedroom Apartments Available Oct 1
22 High St, Unit 5
22 High StMedford, MA 02155
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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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$3,4003 Bedroom Apartments Available Sep 1
186 Powder House Blvd, Unit 4
186 Powder House BlvdSomerville, MA 02144
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.
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$3,0002 Bedroom Apartments Available Now
10 Davis St, Unit 2
10 Davis StWoburn, MA 01801
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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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$3,2002 Bedroom Apartments Available Sep 1
96 Capen St, Unit #2
96 Capen StMedford, MA 02155
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$4,5003 Bedroom Apartments Available Now
1 College Ave
1 College AveMedford, MA 02155
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$3,0002 Bedroom Apartments Available Sep 1
79 Capen St, Unit 2
79 Capen StMedford, MA 02155
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$3,0003 Bedroom Apartments Available Sep 1
34 Hume Ave, Unit 1
34 Hume AveMedford, MA 02155
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$2,6002 Bedroom Apartments Available Sep 1
22 High St, Unit 11
22 High StMedford, MA 02155
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$5,5005 Bedroom Apartments Available Now
260 Boston Ave, Unit 2
260 Boston AveMedford, MA 02155
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$6,0004 Bedroom Apartments Available Aug 1
27 Emery St, Unit 1
27 Emery StMedford, MA 02155
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.
Showing Results 1-50, Page 1 of 2
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
- Nearby Cities
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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.
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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.
Helpful Local Expert Guides
What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
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Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!
Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
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.
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It
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Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.
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There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
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Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
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.