15 Piggott Rd
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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$1,750Studio Apartments Available Now
2 Elmwood Ave
2 Elmwood AveWinchester, MA 01890
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$1,780Studio Apartments Available Now
182 Central St
182 Central StStoneham, MA 02180
7 Old Colony Ln
ArlingtonMA02476
14 Brattle Ln, Unit 6
14 Brattle Ln
ArlingtonMA02474
200 Swanton St
WinchesterMA01890
71 Grove St
ArlingtonMA02474
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$1,900Studio Apartments Available Now
385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
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$1,900Studio Apartments Available Now
385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
385 Massachusetts Ave
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.
4 Viking Ct
ArlingtonMA02474
14 Church Ave
WoburnMA01801
14 Church Ave
WoburnMA01801
6 Harris Cir
ArlingtonMA02474
12 Brattle Dr
ArlingtonMA02474
0 Brattle Dr
ArlingtonMA02474
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$1,9501 Bedroom Apartments Available Feb 8
35 Prospect St
35 Prospect StWoburn, MA 01801
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$1,9501 Bedroom Apartments Available Now
12 Brattle Dr
12 Brattle DrArlington, MA 02474
19 N Union St
ArlingtonMA02474
26 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.
5 Viking Ct
ArlingtonMA02474
15 Old Colony Ln
ArlingtonMA02476
9 Dudley St, Unit C
9 Dudley St
ArlingtonMA02476
3 Arizona Terrace
ArlingtonMA02474
15 Allen St, Unit 8
15 Allen St
ArlingtonMA02474
15 Allen St, Unit 4
15 Allen St
ArlingtonMA02474
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$2,0501 Bedroom Apartments Available Mar 15
276 Massachusetts Ave
276 Massachusetts AveArlington, MA 02474
71 Montvale Ave
StonehamMA02180
333 Massachusetts Ave
ArlingtonMA02474
995 Massachusetts Ave
ArlingtonMA02476
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.
49 Broadway
ArlingtonMA02474
69 Grove St
ArlingtonMA02474
898 Massachusetts Ave
ArlingtonMA02476
11 Brattle Dr, Unit 5
11 Brattle Dr
ArlingtonMA02474
35 Montvale Ave
WoburnMA01801
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$2,2001 Bedroom Apartments Available Mar 2
898 Massachusetts Ave
898 Massachusetts AveArlington, MA 02476
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$2,2001 Bedroom Apartments Available Jun 1
5 Boston Ave
5 Boston AveMedford, MA 02155
67 Grove St
ArlingtonMA02474
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$2,2501 Bedroom Apartments Available Mar 2
385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
385 Massachusetts Ave
ArlingtonMA02474
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.
47 Broadway
ArlingtonMA02474
11 Heath Rd
ArlingtonMA02474
422 High St, Unit 9
422 High St
MedfordMA02155
56 Warren Ave
WoburnMA01801
74 Beach St
WoburnMA01801
375 Massachusetts Ave, Unit 49
375 Massachusetts Ave
ArlingtonMA02474
177 Central St
StonehamMA02180
12 Davis St
WoburnMA01801
27 Arlington Rd, Unit 5
27 Arlington Rd
WoburnMA01801
43 Harvard St, Unit 1
43 Harvard St
WinchesterMA01890
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 | $2,905 | $2,075 | $5,580 |
| Winchester 3 Bedroom Homes for Rent | $3,640 | $2,500 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $4,884 | $3,425 | $7,000 |
| Winchester 5 Bedroom Homes for Rent | $6,438 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,282 | $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
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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 Old Colony Apartments in the Rock Meadow neighborhood priced from $1,750. Brattle Drive Apartments in the Rock Meadow neighborhood has the second lowest priced unit, which is a Studio apartment currently listed from $1,800. Here is today’s list of the most affordable Winchester apartments for rent:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
| Brattle Drive Apartments | Studio | Studio,1BA | $1,800 |
| 71-73 Winn St | One Bedroom | 1BR,1BA | $1,900 |
| 2-15 Winn Park | Studio | Studio,1BA | $1,950 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| Shaker Glen Village | Oak | 1BR,1BA | $1,995 |
Best Value Apartments for Rent in Winchester, MA
As of February 08, 2026 the best value apartment in the Winchester area is the $0.30 price per square foot 1 Victoria St Model at 1 Victoria St, Unit 1A in the in the Strawberry Hill neighborhood starting from $2,975. The second greatest value Winchester apartment is the 96 Conwell Ave Model at 96 Conwell Ave, Unit 1 starting at $3,000 with a $0.30 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. |
|---|---|---|---|
| 1 Victoria St, Unit 1A | 1 Victoria St | 2BR,1BA | $0.30 |
| 96 Conwell Ave, Unit 1 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 96 Conwell Ave, Unit 1 | 96 Conwell Ave | 3BR,1BA | $0.33 |
| 96 Conwell Ave, Unit 2 | 96 Conwell Ave | 3BR,1BA | $0.33 |
| 96 Conwell Ave, Unit 2 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 1 Victoria St, Unit #1A | 1 Victoria St | 2BR,1BA | $0.30 |
| 79 Capen St, Unit 1 | 79 Capen St | 2BR,1BA | $0.27 |
| 29 Capen St, Unit #2 | 29 Capen St | 2BR,1.5BA | $0.30 |
| 124 Forest St, Unit 2 | 124 Forest St | 3BR,1BA | $0.30 |
| 195 Forest St | 195 Forest St | 4BR,2.5BA | $0.31 |
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 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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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 451 Apartments for Rent in Winchester, MA with pricing that ranges from $900 to $10,016. There are also 248 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,750 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 $1,750 to $28,000 with an average monthly rent of $4,306.
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 $2,500 to $5,595, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,425 and Four Bedroom Apartments start at $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
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.