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$9503 Bedroom Apartments Available Now
13 Center St, Unit 2
13 Center StWoburn, MA 01801
Cheap Homes for Rent in Winchester, MA from $1,200 (49 Rentals)
Search the lowest-cost Homes available for rent right now in Winchester.
74 Sharon St
MedfordMA02155
31 Raymond Ave
SomervilleMA02144
6 Boston Ave
MedfordMA02155
12 Colonial Village Dr
ArlingtonMA02474
84 Franklin St, Unit 2
84 Franklin St
StonehamMA02180
33 Montvale Ave, Unit #3
33 Montvale Ave
WoburnMA01801
15 Governors Ave, Unit 19
15 Governors Ave
MedfordMA02155
7 Harris Cir
ArlingtonMA02474
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.
15 Governors Ave, Unit 19
15 Governors Ave
MedfordMA02155
60 Franklin St
StonehamMA02180
71 Montvale Ave
StonehamMA02180
80 N Warren St
WoburnMA01801
21 Bradlee Rd
MedfordMA02155
67 Grove St
ArlingtonMA02474
77 Fairfax St, Unit B
77 Fairfax St
SomervilleMA02144
8 Old Colony Ln
ArlingtonMA02476
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$2,1501 Bedroom Apartments Available Now
52 Mill St, Unit 11
52 Mill StWoburn, MA 01801
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.
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$2,1501 Bedroom Apartments Available Aug 4
11 Brattle Dr, Unit 5
11 Brattle DrArlington, MA 02474
15 Governors Ave, Unit 8
15 Governors Ave
MedfordMA02155
15 Governors Ave, Unit 5
15 Governors Ave
MedfordMA02155
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$2,2001 Bedroom Apartments Available Aug 4
0 Brattle Dr, Unit 6
0 Brattle DrArlington, MA 02474
12 Brattle Dr, Unit 1
12 Brattle Dr
ArlingtonMA02474
12 Brattle Dr
ArlingtonMA02474
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$2,2001 Bedroom Apartments Available Aug 1
22 High St, Unit 1
22 High StMedford, MA 02155
15 Governors Ave, Unit 24
15 Governors Ave
MedfordMA02155
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$2,2501 Bedroom Apartments Available Aug 4
2 Brattle Dr, Unit 7
2 Brattle DrArlington, MA 02474
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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$2,2501 Bedroom Apartments Available Jul 2
0 Brattle Dr, Unit 10
0 Brattle DrArlington, MA 02474
200 Swanton St
WinchesterMA01890
47 Mystic St
ArlingtonMA02474
14 Arizona Terrace
ArlingtonMA02474
22 Hamilton Rd
ArlingtonMA02474
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$2,3001 Bedroom Apartments Available Jul 2
8 Brattle Dr, Unit 2
8 Brattle DrArlington, MA 02474
34 Hamilton Rd, Unit 206
34 Hamilton Rd
ArlingtonMA02474
29 -2 Arlington Rd, Unit 6
29 -2 Arlington Rd
WoburnMA01801
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$2,4001 Bedroom Apartments Available Sep 1
48 Rawson Rd
48 Rawson RdArlington, MA 02474
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.
121 Cambridge Rd
WoburnMA01801
107 Warren St, Unit 2
107 Warren St
ArlingtonMA02474
49 Broadway, Unit 9
49 Broadway
ArlingtonMA02474
74 Beach St
WoburnMA01801
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$2,4502 Bedroom Apartments Available Jul 1
50 Mill St, Unit 11
50 Mill StWoburn, MA 01801
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
39 Franklin St
WoburnMA01801
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$2,5002 Bedroom Apartments Available Jul 1
7 Totman Dr, Unit 1
7 Totman DrWoburn, MA 01801
2 Manor Ter
LexingtonMA02420
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.
995 Massachusetts Ave
ArlingtonMA02476
993 Massachusetts Ave
ArlingtonMA02476
558 Main St
StonehamMA02180
98 Sylvia St
LexingtonMA02421
Showing Results 1-49, Page 1 of 1
Winchester, MA Local Guide
How much does it cost to rent a home in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $3,069 | $2,100 | $4,500 |
| Winchester 3 Bedroom Homes for Rent | $4,121 | $2,500 | $7,500 |
| Winchester 4 Bedroom Homes for Rent | $5,182 | $1,300 | $10,000+ |
| Winchester 5 Bedroom Homes for Rent | $7,531 | $4,525 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $10,755 | $5,995 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,150 | $5,300 | $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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- Local Counties
- School Districts
Cheapest Available Winchester Apartments for Rent
The cheapest available apartment rental in Winchester, MA is a Studio unit found at 109 Oxford St in the East Arlington neighborhood priced from $1,650. 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 |
|---|---|---|---|
| 109 Oxford St | 3 | Studio,1BA | $1,650 |
| Old Colony Apartments | Studio | Studio,1BA | $1,750 |
| Mill Street Gardens | 1 Bedroom, 1 Bath | 1BR,1BA | $1,950 |
| 2-15 Winn Park | Studio | Studio,1BA | $2,050 |
| Tudor Glen Village | The Cedar | 1BR,1BA | $2,095 |
| Arlington Gardens | 1B1G | 1BR,1BA | $2,200 |
| Shaker Glen Village | Pine | 1BR,1BA | $2,295 |
| 840-846 Massachusetts Ave | Studio | Studio,1BA | $2,300 |
Best Value Apartments for Rent in Winchester, MA
As of June 24, 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 |
| 14 Dow St, Unit 2 | 14 Dow St | 5BR,2BA | $0.64 |
| 56 Gordon St, Unit 2 | 56 Gordon St | 4BR,1BA | $0.40 |
| 77 Fairfax St | 77 Fairfax St | 2BR,1BA | $0.33 |
| 43 Martin St, Unit 1 | 43 Martin St | 4BR,2BA | $0.44 |
| 124 Forest St, Unit 3B | 124 Forest St | 3BR,1BA | $0.27 |
| 19 Adams St, Unit 2A | 19 Adams St | 3BR,2BA | $0.40 |
| 19 Adams St, Unit 2R | 19 Adams St | 3BR,2BA | $0.40 |
| 6 Munroe St, Unit 2 | 6 Munroe St | 3BR,2BA | $0.89 |
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 Article
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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Remember the 3 Rules of Real Estate:Location, Location, Location!
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 392 Apartments for Rent in Winchester, MA with pricing that ranges from $950 to $11,166. There are also 257 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,210 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 $1,210 to $28,000 with an average monthly rent of $5,384.
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 $950 to $6,317, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $7,500. Four Bedroom Single-Family rentals are also available starting from $1,300 and Four Bedroom Apartments start at $2,900.
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.
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Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.
Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.
Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.