171 Swanton St
WinchesterMA01890
3 Bedroom Homes for Rent in Winchester, MA (64 Rentals)
63-65 Harvard St
WinchesterMA01890
22 Baldwin St
WinchesterMA01890
129 Washington St
WinchesterMA01890
31 Fells Rd
WinchesterMA01890
21 Royall St, Unit 3B1B on 2nd FL
21 Royall St
MedfordMA02155
52 Clark St, Unit 1
52 Clark St
MedfordMA02155
333 Alewife Brook Pky, Unit 2
333 Alewife Brook Pky
SomervilleMA02144
31 Lyman Ave
MedfordMA02155
72 Harlow St, Unit 72
72 Harlow St
ArlingtonMA02474
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.
258 Boston Ave
MedfordMA02155
42 Belknap St
SomervilleMA02144
4 Park St, Unit 1
4 Park St
ArlingtonMA02474
106 Boston Ave
MedfordMA02155
14 Hamilton Rd, Unit 1a
14 Hamilton Rd
SomervilleMA02144
21 Jerome St
MedfordMA02155
112 College Ave, Unit 1##
112 College Ave
MedfordMA02155
3 Hamilton Rd
SomervilleMA02144
62 Woods Ave, Unit 2##
62 Woods Ave
SomervilleMA02144
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$4,0003 Bedroom Apartments Available Sep 1
53 Oakland St, Unit #2
53 Oakland StMedford, MA 02155
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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$3,3003 Bedroom Apartments Available Now
72 Bower St, Unit #1
72 Bower StMedford, MA 02155
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$3,1003 Bedroom Apartments Available Now
92 Sylvia St, Unit 2
92 Sylvia StArlington, MA 02476
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$3,4003 Bedroom Apartments Available Sep 1
186 Powder House Blvd, Unit 4
186 Powder House BlvdSomerville, MA 02144
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$3,6003 Bedroom Apartments Available Now
245 Boston Ave, Unit 3
245 Boston AveMedford, MA 02155
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$4,5003 Bedroom Apartments Available Now
1 College Ave
1 College AveMedford, MA 02155
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$2,7003 Bedroom Apartments Available Now
124 Forest St, Unit 3
124 Forest 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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$3,3903 Bedroom Apartments Available Sep 1
127 Hillsdale Rd
127 Hillsdale RdSomerville, MA 02144
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$3,3003 Bedroom Apartments Available Sep 1
333 Alewife Brook Pkwy, Unit 2
333 Alewife Brook PkwySomerville, MA 02144
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$3,9003 Bedroom Apartments Available Jun 1, 2027
102 W Adams St, Unit 1
102 W Adams StSomerville, 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.
21 Jerome St
MedfordMA02155
Unit
371 Salem St
WoburnMA01801
206 Winthrop St
MedfordMA02155
31 Lyman Ave, Unit 1
31 Lyman Ave
MedfordMA02155
20 Bryant St
WoburnMA01801
74 Cambridge Rd
WoburnMA01801
15 Quincy St
MedfordMA02155
4 Park St
ArlingtonMA02474
36 Carroll Rd
WoburnMA01801
12 Anna Rd
WoburnMA01801
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.
12 Stevens St
MedfordMA02155
132 Grant St
LexingtonMA02420
555 Main St
WoburnMA01801
28 Churchill Ave
ArlingtonMA02476
60 Irving St
MedfordMA02155
15 Wason St
MedfordMA02155
42 Rockland Ave
ArlingtonMA02474
122 Massachusetts Ave
LexingtonMA02420
53 Dickson Ave
ArlingtonMA02474
801 Manor Ter
LexingtonMA02420
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.
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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.
Helpful Local Expert Guides
What It Really Costs to Live in Boston: A Local Renter's Guide
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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
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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!
Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & State Street
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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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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.