0 Green St
WoburnMA01801
Cheap Homes for Rent in Winchester, MA from $1,200 (53 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
190 North St
SomervilleMA02144
200 Swanton St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
74 Beach St, Unit Continental Court
74 Beach St
WoburnMA01801
1 Continental Ct
WoburnMA01801
200 Swanton St
WinchesterMA01890
74 Beach St
WoburnMA01801
50 Franklin St
StonehamMA02180
71 Montvale Ave
StonehamMA02180
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.
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80 N Warren St
WoburnMA01801
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74 Beach St
WoburnMA01801
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$2,100
Plus Fees
1 Bedroom Apartments Available Oct 2333 Massachusetts Ave
333 Massachusetts AveArlington, MA 02476
422 High St, Unit 10
422 High St
MedfordMA02155
9 Ryder St
ArlingtonMA02476
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.
10 Arizona Ter, Unit 4
10 Arizona Ter
ArlingtonMA02474
6 Harris Cir
ArlingtonMA02474
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$2,150
Plus Fees
1 Bedroom Apartments Available Oct 15276 Massachusetts Ave
276 Massachusetts AveArlington, MA 02474
47 Mystic St
ArlingtonMA02474
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71 Montvale Ave
StonehamMA02180
60 Pleasant St
ArlingtonMA02476
993 Massachusetts Ave
ArlingtonMA02476
74 Beach St, Unit 6-9
74 Beach St
WoburnMA01801
993 Massachusetts Ave, Unit 212
993 Massachusetts Ave
ArlingtonMA02476
215 Massachusetts Ave, Unit 47
215 Massachusetts Ave
ArlingtonMA02474
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$2,250
Plus Fees
1 Bedroom Apartments Available Now333 Massachusetts Ave
333 Massachusetts AveArlington, MA 02476
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.
14 Cotting St, Unit 3
14 Cotting St
MedfordMA02155
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22 High St, Unit 9
22 High St
MedfordMA02155
2 Viking Ct
ArlingtonMA02474
20 Hamilton Rd
ArlingtonMA02474
7 Arizona Ter, Unit 2
7 Arizona Ter
ArlingtonMA02474
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The 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.
1 Viking Ct
ArlingtonMA02474
22 High St, Unit 9
22 High St
MedfordMA02155
31 Montvale Ave
WoburnMA01801
22 High St
MedfordMA02155
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6 Skillings Rd
WinchesterMA01890
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
22 High St, Unit 11
22 High St
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.
58 Wright St
StonehamMA02180
79 Mystic St, Unit 2
79 Mystic St
ArlingtonMA02474
35 Vine St
WinchesterMA01890
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 | $3,053 | $2,200 | $6,375 |
| Winchester 3 Bedroom Homes for Rent | $3,890 | $2,850 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $4,990 | $3,425 | $8,500 |
| Winchester 5 Bedroom Homes for Rent | $6,311 | $4,300 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,641 | $5,995 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $7,347 | $6,995 | $7,700 |
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 Leisure Lane Apartments in the West Side neighborhood priced from $1,750. Mill Street Gardens in the Nobility Hill neighborhood has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,950. 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 | $1,750 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| Brattle Drive Apartments | One Bedroom | 1BR,1BA | $1,950 |
| Arlington Gardens Apartments | 1 Bedroom | 1BR,1BA | $2,000 |
| 119 Pleasant St | Studios | Studio,1BA | $2,100 |
| Brookside Apartments | A1 | 1BR,1BA | $2,150 |
Best Value Apartments for Rent in Winchester, MA
As of September 15, 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 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.26 |
| 79 Capen St, Unit 1 | 79 Capen St | 2BR,1BA | $0.27 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.29 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.26 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.29 |
| 69 Raymond Ave, Unit 1R | 69 Raymond Ave | 2BR,1BA | $0.29 |
| 26 Adams St, Unit 3 | 26 Adams St | 2BR,1BA | $0.23 |
| 27 Holton St, Unit 1 | 27 Holton St | 2BR,1BA | $0.30 |
Quick 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 636 Apartments for Rent in Winchester, MA with pricing that ranges from $1,550 to $9,300. There are also 405 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,200 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 $1,200 to $40,000 with an average monthly rent of $4,804.
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 $2,250 to $7,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,850 to $20,000. Four Bedroom Single-Family rentals are also available starting from $3,425 and Four Bedroom Apartments start at $3,200.
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.
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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.
The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.