50 Water St, Unit 12A
50 Water St
MedfordMA02155
Cheap Homes for Rent in Winchester, MA from $1,700 (60 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
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$1,725Studio Apartments Available Now
4 Brattle Dr
4 Brattle DrArlington, MA 02474
15 Piggott Rd
MedfordMA02155
64 Main St, Unit 47B
64 Main St
StonehamMA02180
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$1,780Studio Apartments Available Now
182 Central St
182 Central StStoneham, MA 02180
385 Massachusetts Ave
ArlingtonMA02474
71 Grove St
ArlingtonMA02474
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$1,900Studio Apartments Available Apr 1
50 Mill St
50 Mill StWoburn, MA 01801
159 Franklin St
StonehamMA02180
26 Heath Rd
ArlingtonMA02474
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.
5 Viking Ct
ArlingtonMA02474
71 Montvale Ave
StonehamMA02180
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 3
200 Swanton St
WinchesterMA01890
150 Main St
StonehamMA02180
15 Allen St, Unit 8
15 Allen St
ArlingtonMA02474
15 Allen St, Unit 4
15 Allen St
ArlingtonMA02474
1 Colonial Village Dr
ArlingtonMA02474
422 High St
MedfordMA02155
47 Broadway
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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$2,1501 Bedroom Apartments Available Apr 1
11 Allen St
11 Allen StArlington, MA 02474
69 Grove St
ArlingtonMA02474
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$2,1951 Bedroom Apartments Available Apr 1
68 Mill St
68 Mill StWoburn, MA 01801
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$2,2001 Bedroom Apartments Available Apr 1
898 Massachusetts Ave
898 Massachusetts AveArlington, MA 02476
105 Winthrop St, Unit 1
105 Winthrop St
MedfordMA02155
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$2,2001 Bedroom Apartments Available Jun 1
5 Boston Ave
5 Boston AveMedford, MA 02155
376 Massachusetts Ave, Unit 34
376 Massachusetts Ave
ArlingtonMA02474
67 Grove St
ArlingtonMA02474
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$2,2501 Bedroom Apartments Available Jun 2
8 Brattle Dr
8 Brattle DrArlington, MA 02474
11 Heath Rd
ArlingtonMA02474
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.
7 Arizona Ter, Unit 2
7 Arizona Ter
ArlingtonMA02474
47 Broadway
ArlingtonMA02474
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$2,3001 Bedroom Apartments Available Sep 1
163 Summer St
163 Summer StArlington, MA 02474
1 Viking Ct
ArlingtonMA02474
74 Beach St
WoburnMA01801
375 Massachusetts Ave, Unit 49
375 Massachusetts Ave
ArlingtonMA02474
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$2,381Studio Apartments Available Now
30 Mill St
30 Mill StArlington, MA 02476
47 Broadway
ArlingtonMA02474
5 Arizona Ter, Unit 6
5 Arizona Ter
ArlingtonMA02474
157 Franklin St, Unit A11
157 Franklin St
StonehamMA02180
Explore Like a Local: The Insider's Guide to Boston
Explore Boston like a local with our guide to neighborhoods, history, and hidden gems. Discover the city's best apartments, from historic brownstones to modern high-rises, and find your perfect Boston home.
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$2,4502 Bedroom Apartments Available Now
82 Mill St
82 Mill StWoburn, MA 01801
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$2,4502 Bedroom Apartments Available Jul 1
50 Mill St
50 Mill StWoburn, MA 01801
80 N Warren St
WoburnMA01801
4 Colonial Village Dr, Unit 9
4 Colonial Village Dr
ArlingtonMA02474
4 Colonial Village Dr
ArlingtonMA02474
1 Old Colony Ln, Unit 2
1 Old Colony Ln
ArlingtonMA02476
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
385 Massachusetts Ave
ArlingtonMA02474
374 Massachusetts Ave, Unit 63
374 Massachusetts Ave
ArlingtonMA02474
46 Grafton St, Unit 1st Fl
46 Grafton St
ArlingtonMA02474
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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 | $3,007 | $2,150 | $5,350 |
| Winchester 3 Bedroom Homes for Rent | $4,159 | $2,600 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $5,045 | $3,425 | $7,000 |
| Winchester 5 Bedroom Homes for Rent | $7,177 | $4,325 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,147 | $6,200 | $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
- ZIP codes
- Local Counties
- School Districts
Cheapest Available Winchester Apartments for Rent
The cheapest available apartment rental in Winchester, MA is a 1 Bed unit found at Elmwood Apartments in the Nobility Hill neighborhood priced from $1,500. 79 Montvale Ave in the Walnut Hill neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,700. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Elmwood Apartments | Studio 250 sf | 1BR,1BA | $1,500 |
| 79 Montvale Ave | Studio | Studio,1BA | $1,700 |
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
| Leisure Lane Apartments | studio | Studio,1BA | $1,795 |
| Mass Ave, 385 | Studio 0 Bed 1 Bath 476sf | Studio,1BA | $1,825 |
| 2-15 Winn Park | Studio | Studio,1BA | $1,950 |
| Mass Ave 333-Allen Street Apartments | 1 Bed 1 Bath 650sf | 1BR,1BA | $2,075 |
| Tudor Glen Village | The Beech | 1BR,1BA | $2,095 |
Best Value Apartments for Rent in Winchester, MA
As of March 25, 2026 the best value apartment in the Winchester area is the $0.33 price per square foot 96 Conwell Ave Model at 96 Conwell Ave, Unit 1 in the in the Strawberry Hill neighborhood starting from $3,300. The second greatest value Winchester apartment is the 96 Conwell Ave Model at 96 Conwell Ave, Unit 2 starting at $3,300 with a $0.33 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. |
|---|---|---|---|
| 96 Conwell Ave, Unit 1 | 96 Conwell Ave | 3BR,1BA | $0.33 |
| 96 Conwell Ave, Unit 2 | 96 Conwell Ave | 3BR,1BA | $0.33 |
| 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 |
| 79 Capen St, Unit 1 | 79 Capen St | 2BR,1BA | $0.27 |
| 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 |
| 124 Forest St, Unit 1 | 124 Forest St | 3BR,2BA | $0.35 |
| 258 Boston Ave | 258 Boston Ave | 3BR,1BA | $0.37 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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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.
Read ArticleDon'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 ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash 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.
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 ArticleQuick Rent Budget Calculator
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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 472 Apartments for Rent in Winchester, MA with pricing that ranges from $1,650 to $19,152. There are also 253 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,700 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 $1,700 to $28,000 with an average monthly rent of $4,498.
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 $2,300 to $5,761, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,600 to $16,000. Four Bedroom Single-Family rentals are also available starting from $3,425 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
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
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.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.