60 Lake St
WinchesterMA01890
Luxury Homes for Rent in Winchester, MA (211 Rentals)
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
63-65 Harvard St
WinchesterMA01890
63 Holland St
WinchesterMA01890
171 Swanton St
WinchesterMA01890
488 Washington St
WinchesterMA01890
22 Baldwin St
WinchesterMA01890
129 Washington St
WinchesterMA01890
17 Churchill Rd
WinchesterMA01890
31 Fells Rd
WinchesterMA01890
270 Cross St
WinchesterMA01890
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.
46 Loring Ave
WinchesterMA01890
18 Grant Rd
WinchesterMA01890
161 Highland Ave
WinchesterMA01890
161 Highland Ave
WinchesterMA01890
59 Wedgemere Ave
WinchesterMA01890
186 Ridge St
WinchesterMA01890
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$2,5002 Bedroom Apartments Available Now
7 Totman Dr, Unit 1
7 Totman DrWoburn, MA 01801
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
995 Massachusetts Ave
ArlingtonMA02476
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$2,5002 Bedroom Apartments Available Now
68 Mill St, Unit 11
68 Mill StWoburn, MA 01801
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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$2,5002 Bedroom Apartments Available Now
62 Mill St, Unit 6
62 Mill StWoburn, MA 01801
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$2,5002 Bedroom Apartments Available Now
50 Mill St, Unit 5
50 Mill StWoburn, MA 01801
50 Water St
MedfordMA02155
39 Mishawum Rd
WoburnMA01801
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$2,5001 Bedroom Apartments Available Sep 2
898 Massachusetts Ave, Unit 23
898 Massachusetts AveArlington, MA 02476
1033 Massachusetts Ave, Unit 10
1033 Massachusetts Ave
ArlingtonMA02476
898 Massachusetts Ave, Unit 23
898 Massachusetts Ave
ArlingtonMA02476
50 Water St, Unit 76
50 Water St
MedfordMA02155
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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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$2,6002 Bedroom Apartments Available Sep 1
22 High St, Unit 11
22 High StMedford, MA 02155
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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$2,6002 Bedroom Apartments Available Now
66 Mill St, Unit 8
66 Mill StWoburn, MA 01801
202 Central St
StonehamMA02180
27 Highland St
WoburnMA01801
3 Colonial Village Dr, Unit 10
3 Colonial Village Dr
ArlingtonMA02474
177 Central St
StonehamMA02180
100 High St
MedfordMA02155
898 Massachusetts Ave, Unit 24
898 Massachusetts Ave
ArlingtonMA02476
122 Warren St
MedfordMA02155
184 Winthrop St, Unit 2
184 Winthrop St
MedfordMA02155
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$2,7003 Bedroom Apartments Available Now
124 Forest St, Unit 3
124 Forest StMedford, MA 02155
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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$2,7501 Bedroom Apartments Available Now
898 Massachusetts Ave, Unit 31
898 Massachusetts AveArlington, MA 02476
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$2,7501 Bedroom Apartments Available Now
32 Walnut St
32 Walnut StArlington, MA 02476
32 Gourley Rd
MedfordMA02155
46 Clewley Rd, Unit 3
46 Clewley Rd
MedfordMA02155
14 Irvington Rd, Unit 14 Irvington Road
14 Irvington Rd
SomervilleMA02144
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$2,9002 Bedroom Apartments Available Now
92 Sylvia St
92 Sylvia StArlington, MA 02474
34 Hamilton Rd
ArlingtonMA02474
1 Main St
WoburnMA01801
74 Cambridge Rd
WoburnMA01801
27-29-29 Cornell St
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 | $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.
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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.
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
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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.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
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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.