35 Vine St
WinchesterMA01890
2 Bedroom Homes for Rent in Winchester, MA (54 Rentals)
31 Irving St
WinchesterMA01890
60 Lake St
WinchesterMA01890
7 Conant Rd
WinchesterMA01890
33 Nelson St
WinchesterMA01890
63 Holland St
WinchesterMA01890
67 Church St
WinchesterMA01890
8 Richardson St
WinchesterMA01890
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
35 Century St, Unit 1
35 Century St
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.
46 Clewley Rd, Unit 3
46 Clewley Rd
MedfordMA02155
53 Fairfax St, Unit 1
53 Fairfax St
SomervilleMA02144
1 Watermill Pl, Unit 112
1 Watermill Pl
ArlingtonMA02476
29 Harvard Ave, Unit 33
29 Harvard Ave
MedfordMA02155
1 Victoria St
SomervilleMA02144
245 Boston Ave, Unit 3
245 Boston Ave
MedfordMA02155
95 Capen St, Unit Apt 1
95 Capen St
MedfordMA02155
1 Victoria St
SomervilleMA02144
14 Kilby St
WoburnMA01801
2012 Symmes Cir, Unit 1
2012 Symmes Cir
ArlingtonMA02474
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.
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$2,8952 Bedroom Apartments Available Jul 1
286 Main St, Unit 104
286 Main StWoburn, MA 01801
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$3,0002 Bedroom Apartments Available Jul 1
10 Davis St, Unit 2
10 Davis StWoburn, MA 01801
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$3,0002 Bedroom Apartments Available Now
92 Sylvia St
92 Sylvia StArlington, MA 02474
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$2,7952 Bedroom Apartments Available Now
286 Main St, Unit 206
286 Main StWoburn, MA 01801
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$2,5002 Bedroom Apartments Available Jul 1
7 Totman Dr, Unit 1
7 Totman DrWoburn, MA 01801
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$2,4502 Bedroom Apartments Available Jul 1
50 Mill St, Unit 11
50 Mill StWoburn, MA 01801
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$2,9502 Bedroom Apartments Available Now
10 Fessenden Rd, Unit 2
10 Fessenden RdArlington, MA 02476
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$3,1002 Bedroom Apartments Available Now
385 Massachusetts Ave, Unit 32
385 Massachusetts AveArlington, MA 02474
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$3,0002 Bedroom Apartments Available Sep 1
79 Capen St, Unit 2
79 Capen StMedford, MA 02155
29 -2 Arlington Rd, Unit 6
29 -2 Arlington Rd
WoburnMA01801
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
286 Main St, Unit 104
286 Main St
WoburnMA01801
67 Grove St
ArlingtonMA02474
57 Russell St
WoburnMA01801
121 Cambridge Rd
WoburnMA01801
74 Beach St
WoburnMA01801
2 Manor Ter
LexingtonMA02420
220 Central St
StonehamMA02180
48 Fountain St
MedfordMA02155
202 Central St
StonehamMA02180
100 High St
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
64 Main St
StonehamMA02180
15 1st St
WoburnMA01801
61 Wright St
StonehamMA02180
2500 Mystic Valley Pkwy
MedfordMA02155
32 Williams St
ArlingtonMA02476
1 Main St
WoburnMA01801
32 Gourley Rd
MedfordMA02155
380 Place Ln
WoburnMA01801
282 Place Ln
WoburnMA01801
52 Mt Vernon St
ArlingtonMA02476
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.
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
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Winchester, MA Local Guide
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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 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.