0 Green St
WoburnMA01801
Cheap Homes for Rent in Winchester, MA from $1,100 (47 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
46-48-48 Moulton Rd
ArlingtonMA02476
9 Woodland Ave
MedfordMA02155
6 Boston Ave
MedfordMA02155
48 Warren Ave
WoburnMA01801
13 Mill St, Unit 1F
13 Mill St
ArlingtonMA02476
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7 Old Colony Ln
ArlingtonMA02476
200 Swanton St
WinchesterMA01890
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.
50 Franklin St
StonehamMA02180
71 Montvale Ave
StonehamMA02180
200 Swanton St
WinchesterMA01890
314 Massachusetts Ave, Unit 11
314 Massachusetts Ave
ArlingtonMA02474
339 Massachusetts Ave, Unit 10
339 Massachusetts Ave
ArlingtonMA02474
3 Brattle Dr, Unit 3
3 Brattle Dr
ArlingtonMA02474
310 Massachusetts Ave, Unit 11
310 Massachusetts Ave
ArlingtonMA02474
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$2,000
Plus Fees
Studio Apartments Available Now385 Massachusetts Ave
385 Massachusetts AveArlington, MA 02474
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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10 Arizona Ter, Unit 4
10 Arizona Ter
ArlingtonMA02474
71 Montvale Ave
StonehamMA02180
6 Harris Cir
ArlingtonMA02474
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422 High St, Unit 10
422 High St
MedfordMA02155
14 Cotting St, Unit 3
14 Cotting St
MedfordMA02155
4 Old Colony Ln
ArlingtonMA02476
27 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.
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60 Pleasant St
ArlingtonMA02476
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$2,150
Plus Fees12 Month Lease Term
1 Bedroom Apartments Available Now276 Massachusetts Ave
276 Massachusetts AveArlington, MA 02474
200 Swanton St
WinchesterMA01890
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$2,200
Plus Fees
1 Bedroom Apartments Available Nov 12898 Massachusetts Ave
898 Massachusetts AveArlington, MA 02476
892 Massachusetts Ave, Unit 50
892 Massachusetts Ave
ArlingtonMA02476
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15 Old Colony Ln
ArlingtonMA02476
993 Massachusetts Ave
ArlingtonMA02476
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.
200 Swanton St
WinchesterMA01890
215 Massachusetts Ave, Unit 47
215 Massachusetts Ave
ArlingtonMA02474
2 Viking Ct
ArlingtonMA02474
69 Grove St
ArlingtonMA02474
3 Colonial Village Dr
ArlingtonMA02474
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1 Brattle Dr, Unit 9
1 Brattle Dr
ArlingtonMA02474
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.
177 Central St
StonehamMA02180
31 Montvale Ave
WoburnMA01801
Showing Results 1-47, Page 1 of 1
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 | $2,991 | $2,075 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,898 | $1,200 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $5,166 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,884 | $4,300 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,479 | $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 Studio unit found at 840-846 Massachusetts Ave in the Arlington Center neighborhood priced from $1,200. Leisure Lane Apartments in the West Side 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 |
|---|---|---|---|
| 840-846 Massachusetts Ave | 840 - Studio | Studio,1BA | $1,200 |
| Leisure Lane Apartments | studio | Studio,1BA | $1,750 |
| Old Colony Apartments | Studio | Studio,1BA | $1,850 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| 119 Pleasant St | Studios | Studio,1BA | $2,100 |
Best Value Apartments for Rent in Winchester, MA
As of October 31, 2025 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 2 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 96 Conwell Ave, Unit 1 | 96 Conwell Ave | 2BR,1BA | $0.30 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.26 |
| 1 Victoria St, Unit #1A | 1 Victoria St | 2BR,1BA | $0.30 |
| 79 Capen St, Unit 1 | 79 Capen St | 2BR,1BA | $0.27 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.26 |
| 29 Capen St, Unit #2 | 29 Capen St | 2BR,1.5BA | $0.30 |
| 8 Cross St | 8 Cross St | 3BR,2BA | $0.28 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
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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 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
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 519 Apartments for Rent in Winchester, MA with pricing that ranges from $1,200 to $9,300. There are also 321 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,100 to $40,000.
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 $1,100 to $40,000 with an average monthly rent of $4,679.
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 $6,900, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,200 to $20,000. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $3,000.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.
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.
Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.
How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!
The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.