63-65 Harvard St
WinchesterMA01890
3 Bedroom Homes for Rent in Winchester, MA (70 Rentals)
16 Richardson St
WinchesterMA01890
52 Charles Rd
WinchesterMA01890
11 Highland View Ave
WinchesterMA01890
22 Grove Pl
WinchesterMA01890
17 Cardinal St
WinchesterMA01890
31 Fells Rd
WinchesterMA01890
40 Sturges St, Unit 1
40 Sturges St
MedfordMA02155
56 Gordon St
SomervilleMA02144
260 Boston Ave, Unit 1
260 Boston Ave
MedfordMA02155
Renting with Roommates: Realistic Expectations for Shared Lease
Sharing a lease? Learn how to set clear expectations with your roommates on routines, bills, and cleaning to ensure a successful and peaceful shared living arrangement.
72 Harlow St, Unit 72
72 Harlow St
ArlingtonMA02474
258 Boston Ave
MedfordMA02155
258 Boston Ave, Unit 3
258 Boston Ave
MedfordMA02155
207 Boston Ave
MedfordMA02155
7 Greenleaf Ave, Unit 1
7 Greenleaf Ave
MedfordMA02155
88 North St
SomervilleMA02144
31 Lyman Ave
MedfordMA02155
124 Forest St, Unit 1
124 Forest St
MedfordMA02155
4 Park St, Unit 1
4 Park St
ArlingtonMA02474
32 Irvington Rd
SomervilleMA02144
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
5 Harris Rd
MedfordMA02155
62 Newport St, Unit 2
62 Newport St
ArlingtonMA02476
14 Hamilton Rd, Unit 1a
14 Hamilton Rd
SomervilleMA02144
2 High St, Unit 1
2 High St
SomervilleMA02144
38 George St
MedfordMA02155
32 Irvington Rd
SomervilleMA02144
841 Fellsway W
MedfordMA02155
57 Greenleaf Ave, Unit 3
57 Greenleaf Ave
MedfordMA02155
21 Jerome St
MedfordMA02155
112 College Ave, Unit 1##
112 College Ave
MedfordMA02155
Renting Smart: Lease Basics Every Renter Needs
Demystify Your Rental Lease. Learn the basics about renting, deposits, and tenant/landlord responsibilities. Rent smart and avoid surprises. | Renter University at ApartmentHomeLiving.com
127 Hillsdale Rd, Unit Second
127 Hillsdale Rd
SomervilleMA02144
3 Hamilton Rd
SomervilleMA02144
89 Sherwood Rd
MedfordMA02155
62 Woods Ave, Unit 2##
62 Woods Ave
SomervilleMA02144
2 Osgood St, Unit 1
2 Osgood St
SomervilleMA02143
39 Newland Rd
ArlingtonMA02474
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$3,3503 Bedroom Apartments Available Sep 1
32 Curtis Ave, Unit 2
32 Curtis AveSomerville, MA 02144
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$9503 Bedroom Apartments Available Now
13 Center St, Unit 2
13 Center StWoburn, MA 01801
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$3,1003 Bedroom Apartments Available Now
92 Sylvia St, Unit 2
92 Sylvia StArlington, MA 02476
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$4,5003 Bedroom Apartments Available Jul 15
1 College Ave
1 College AveMedford, 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.
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$3,6503 Bedroom Apartments Available Now
38 George St, Unit 1
38 George StMedford, MA 02155
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$4,3503 Bedroom Apartments Available Sep 1
50 Raymond Ave, Unit 2
50 Raymond AveSomerville, MA 02144
33 Raymond Ave, Unit 2
33 Raymond Ave
SomervilleMA02144
35 Stoughton St
MedfordMA02155
10 Spencer St
LexingtonMA02420
16 Kilby St
WoburnMA01801
62 Newport St, Unit 2
62 Newport St
ArlingtonMA02476
21 Jerome St
MedfordMA02155
31 Lyman Ave, Unit 1
31 Lyman Ave
MedfordMA02155
39 Franklin St
WoburnMA01801
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.
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 | $2,100 | $4,500 |
| Winchester 3 Bedroom Homes for Rent | $4,117 | $2,500 | $8,000 |
| Winchester 4 Bedroom Homes for Rent | $5,153 | $1,350 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $8,904 | $4,325 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $10,901 | $6,200 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,400 | $5,300 | $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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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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If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
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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 409 Apartments for Rent in Winchester, MA with pricing that ranges from $950 to $10,993. There are also 289 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,050 to $28,000.
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 $1,050 to $28,000 with an average monthly rent of $5,582.
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 $950 to $6,297, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $8,000. Four Bedroom Single-Family rentals are also available starting from $1,350 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
The 10 Best Affordable Neighborhoods in Boston, MA
Written by: Amelia Ramstead
Boston is known for its exciting combination of early American history and modern high-tech universities and employers.
A Local Experts Guide to the Top Boston Neighborhoods for College Renters
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, Massachusetts! We’re excited to help you find your new home, and getting to know the neighborhood is an important part of that process!
Explore Like a Local: The Insider's Guide to Boston
Written by: Amelia Ramstead
Hello from Boston, Massachusetts! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston, and I’m here to give you the inside scoop on this unique city.
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.
Articles, How-To's, and Tips
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
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.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.
Neighborhood and Market Insights: How to Choose the Right Area to Rent
Written by: Robin Stewart
Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.