200 Swanton St
WinchesterMA01890
Homes for Rent in Winchester, MA Under $2,500 (47 Rentals)
200 Swanton St, Unit 3
200 Swanton St
WinchesterMA01890
4 Colonial Village Dr
ArlingtonMA02474
4 Colonial Village Dr, Unit 9
4 Colonial Village Dr
ArlingtonMA02474
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
15A Jason St, Unit 2A
15A Jason St
ArlingtonMA02476
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$2,4502 Bedroom Apartments Available Jul 1
50 Mill St
50 Mill StWoburn, MA 01801
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$2,4502 Bedroom Apartments Available Now
82 Mill St
82 Mill StWoburn, MA 01801
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$2,381Studio Apartments Available Now
30 Mill St
30 Mill StArlington, MA 02476
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.
375 Massachusetts Ave, Unit 49
375 Massachusetts Ave
ArlingtonMA02474
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$2,3001 Bedroom Apartments Available Sep 1
163 Summer St
163 Summer StArlington, MA 02474
1 Old Colony Ln, Unit 2
1 Old Colony Ln
ArlingtonMA02476
1 Viking Ct
ArlingtonMA02474
74 Beach St
WoburnMA01801
11 Heath Rd
ArlingtonMA02474
376 Massachusetts Ave, Unit 34
376 Massachusetts Ave
ArlingtonMA02474
5 Arizona Ter, Unit 6
5 Arizona Ter
ArlingtonMA02474
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$2,2501 Bedroom Apartments Available Jun 1
5 Arizona Terrace
5 Arizona TerraceArlington, MA 02474
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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$2,2501 Bedroom Apartments Available Jun 2
8 Brattle Dr
8 Brattle DrArlington, MA 02474
5 Arizona Ter, Unit 6
5 Arizona Ter
ArlingtonMA02474
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$2,2001 Bedroom Apartments Available Jun 1
5 Boston Ave
5 Boston AveMedford, MA 02155
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$2,2001 Bedroom Apartments Available Now
898 Massachusetts Ave
898 Massachusetts AveArlington, MA 02476
105 Winthrop St, Unit 1
105 Winthrop St
MedfordMA02155
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$2,1951 Bedroom Apartments Available Now
68 Mill St
68 Mill StWoburn, MA 01801
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$2,1501 Bedroom Apartments Available Now
11 Allen St
11 Allen StArlington, MA 02474
15 Allen St
ArlingtonMA02474
1 Colonial Village Dr
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.
422 High St
MedfordMA02155
122 Decatur St
ArlingtonMA02474
1 Colonial Village Dr
ArlingtonMA02474
333 Massachusetts Ave
ArlingtonMA02474
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$2,0751 Bedroom Apartments Available Now
11 Allen St
11 Allen StArlington, MA 02474
15 Allen St, Unit 4
15 Allen St
ArlingtonMA02474
150 Main St
StonehamMA02180
14 Arizona Terrace
ArlingtonMA02474
5 Viking Ct
ArlingtonMA02474
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
71 Montvale Ave
StonehamMA02180
26 Heath Rd
ArlingtonMA02474
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$1,900Studio Apartments Available Now
50 Mill St
50 Mill StWoburn, MA 01801
80 N Warren St
WoburnMA01801
71 Grove St
ArlingtonMA02474
385 Massachusetts Ave
ArlingtonMA02474
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$1,780Studio Apartments Available Now
182 Central St
182 Central StStoneham, MA 02180
15 Piggott Rd
MedfordMA02155
64 Main St, Unit 47B
64 Main St
StonehamMA02180
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.
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$1,725Studio Apartments Available Now
4 Brattle Dr
4 Brattle DrArlington, MA 02474
50 Water St, Unit 12A
50 Water St
MedfordMA02155
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 | $3,041 | $2,100 | $5,350 |
| Winchester 3 Bedroom Homes for Rent | $4,138 | $2,600 | $10,000+ |
| Winchester 4 Bedroom Homes for Rent | $4,966 | $3,300 | $7,000 |
| Winchester 5 Bedroom Homes for Rent | $7,442 | $4,325 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,271 | $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
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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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
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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Do you know the Winchester area?
If you’re an expert on all things Winchester, tell us what you love (and don't) by rating it and writing a review.
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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 467 Apartments for Rent in Winchester, MA with pricing that ranges from $1,110 to $19,131. There are also 261 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 $4,548.
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 $2,600 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 $3,300 and Four Bedroom Apartments start at $1,150.
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.