13 Center St
WoburnMA01801
Cheap Homes for Rent in Winchester, MA from $900 (80 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
74 Sharon St
MedfordMA02155
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$1,500Studio Apartments Available Now
2 Elmwood Ave, Unit 13
2 Elmwood AveWinchester, MA 01890
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$1,7001 Bedroom Apartments Available May 15
532 Main St, Unit L
532 Main StWoburn, MA 01801
15 Piggott Rd
MedfordMA02155
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$1,780Studio Apartments Available Now
182 Central St, Unit 1
182 Central StStoneham, MA 02180
71 Grove St
ArlingtonMA02474
200 Swanton St, Unit 704, Unit 704
200 Swanton St
WinchesterMA01890
12 Colonial Village Dr
ArlingtonMA02474
200 Swanton St, Unit #704
200 Swanton St
WinchesterMA01890
Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Get a local expert's guide to Boston's top 5 short-term rental neighborhoods. Essential tips on Fenway, Beacon Hill, Seaport, and Allston/Brighton.
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$1,9001 Bedroom Apartments Available Now
2 Elmwood Ave, Unit 22
2 Elmwood AveWinchester, MA 01890
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$1,950Studio Apartments Available Aug 1
15 Governors Ave, Unit 19
15 Governors AveMedford, MA 02155
15 Governors Ave, Unit 19
15 Governors Ave
MedfordMA02155
26 Heath Rd
ArlingtonMA02474
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$1,9501 Bedroom Apartments Available Jul 2
0 Brattle Dr, Unit 10
0 Brattle DrArlington, MA 02474
15 Governors Ave, Unit 19
15 Governors Ave
MedfordMA02155
5 Viking Ct
ArlingtonMA02474
71 Montvale Ave
StonehamMA02180
200 Swanton St, Unit 310
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 3, Unit 3
200 Swanton St
WinchesterMA01890
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
4 Brattle Dr, Unit 3
4 Brattle Dr
ArlingtonMA02474
1 Colonial Village Dr
ArlingtonMA02474
60 Pleasant St, Unit 206, Unit 206
60 Pleasant St
ArlingtonMA02476
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$2,000Studio Apartments Available Now
4 Brattle Dr, Unit 3
4 Brattle DrArlington, MA 02474
74 Beach St, Unit Continental Court, Unit Continental Court
74 Beach St
WoburnMA01801
1 Continental Ct
WoburnMA01801
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$2,050Studio Apartments Available Now
2 Elmwood Ave, Unit 53
2 Elmwood AveWinchester, MA 01890
50 Water St
MedfordMA02155
12 Brattle Dr, Unit 1
12 Brattle Dr
ArlingtonMA02474
77 Fairfax St, Unit B
77 Fairfax St
SomervilleMA02144
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
1 Colonial Village Dr, Unit 3
1 Colonial Village Dr
ArlingtonMA02474
269 Cambridge Rd, Unit undisclosed, Unit undisclosed
269 Cambridge Rd
WoburnMA01801
15 Allen St
ArlingtonMA02474
11 Allen St, Unit 3
11 Allen St
ArlingtonMA02474
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$2,1501 Bedroom Apartments Available Now
11 Allen St, Unit 3
11 Allen StArlington, MA 02474
15 Governors Ave
MedfordMA02155
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$2,195
Plus Fees
1 Bedroom Apartments Contact Us For Availability15 Governors Ave
15 Governors AveMedford, MA 02155
15 Governors Ave, Unit 17, Unit 17
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 16
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
15 Governors Ave
MedfordMA02155
12 Brattle Dr, Unit 6
12 Brattle Dr
ArlingtonMA02474
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$2,2001 Bedroom Apartments Available Jun 1
5 Boston Ave, Unit B
5 Boston AveMedford, MA 02155
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$2,2001 Bedroom Apartments Available Now
898 Massachusetts Ave, Unit 45
898 Massachusetts AveArlington, MA 02476
200 Swanton St
WinchesterMA01890
5 Arizona Ter, Unit 6, Unit 6
5 Arizona Ter
ArlingtonMA02474
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$2,2501 Bedroom Apartments Available Jun 1
5 Arizona Terrace, Unit #6
5 Arizona TerraceArlington, MA 02474
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$2,2501 Bedroom Apartments Available Jun 2
8 Brattle Dr, Unit 5
8 Brattle DrArlington, MA 02474
11 Heath Rd
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.
Winchester, MA Local Guide
Downtown Winchester, Massachusetts by Moonshine4711 is licensed under CC BY-SA 3.0
How much does it cost to rent a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $2,886 | $2,299 | $4,500 |
| Winchester 3 Bedroom Homes for Rent | $4,058 | $950 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $4,847 | $3,100 | $7,900 |
| Winchester 5 Bedroom Homes for Rent | $6,996 | $1,250 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,596 | $5,497 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,800 | $5,600 | $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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Cheapest Available Winchester Apartments for Rent
The cheapest available apartment rental in Winchester, MA is a Studio unit found at Leisure Lane Apartments in the West Side neighborhood priced from $1,695. Old Colony Apartments in the Rock Meadow neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,750. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Leisure Lane Apartments | studio | Studio,1BA | $1,695 |
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| Brattle Drive Apartments | Studio | Studio,1BA | $2,000 |
| Mass Ave 333-Allen Street Apartments | 1 Bed 1 Bath 650sf | 1BR,1BA | $2,050 |
| 2-15 Winn Park | Studio | Studio,1BA | $2,050 |
Best Value Apartments for Rent in Winchester, MA
As of May 10, 2026 the best value apartment in the Winchester area is the $0.40 price per square foot 10 Pinkham Rd Model at 10 Pinkham Rd, Unit 2 in the in the North Medford neighborhood starting from $4,000. The second greatest value Winchester apartment is the 1 Victoria St Model at 1 Victoria St starting at $4,500 with a $0.45 price per square foot in the Strawberry Hill neighborhood. Here is today’s list of the best values for Winchester apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| 10 Pinkham Rd, Unit 2 | 10 Pinkham Rd | 4BR,1BA | $0.40 |
| 1 Victoria St | 1 Victoria St | 4BR,2BA | $0.45 |
| 1 Victoria St, Unit #1A | 1 Victoria St | 2BR,1BA | $0.30 |
| 14 Fairmount St, Unit 14.5 | 14 Fairmount St | 5BR,1BA | $0.63 |
| 82 Quincy St, Unit #2 | 82 Quincy St | 4BR,1BA | $0.46 |
| 29 Capen St, Unit #2 | 29 Capen St | 2BR,1.5BA | $0.30 |
| 3 Hamilton Rd, Unit #2 | 3 Hamilton Rd | 6BR,4BA | $0.59 |
| 282 Boston Ave, Unit 2 | 282 Boston Ave | 5BR,2BA | $0.50 |
| 124 Forest St, Unit 2 | 124 Forest St | 3BR,2BA | $0.30 |
| 258 Boston Ave | 258 Boston Ave | 3BR,1BA | $0.37 |
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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Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleTop 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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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 445 Apartments for Rent in Winchester, MA with pricing that ranges from $950 to $12,327. There are also 309 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $950 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 $950 to $28,000 with an average monthly rent of $5,060.
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 $2,699 to $5,950, while Three Bedroom Homes, Condos, and Townhomes for rent range from $950 to $10,000. Four Bedroom Single-Family rentals are also available starting from $3,100 and Four Bedroom Apartments start at $3,100.
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.
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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.
Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.
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Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.