112 Church St
WinchesterMA01890
Pet Friendly Homes for Rent in Winchester, MA (117 Rentals)
Homes for rent in Winchester that love your dogs or cats as much as you do!
10 Farrow St
WinchesterMA01890
31 Coolidge Rd
WinchesterMA01890
378 Washington St
WinchesterMA01890
2 Rangeley Rd
WinchesterMA01890
476 Fulton St, Unit Unit 478
476 Fulton St
MedfordMA02155
14 Brattle Ln, Unit 6
14 Brattle Ln
ArlingtonMA02474
310 Massachusetts Ave, Unit 11
310 Massachusetts Ave
ArlingtonMA02474
11 Brattle Dr, Unit 2
11 Brattle Dr
ArlingtonMA02474
15 Allen St, Unit 8
15 Allen St
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.
339 Massachusetts Ave, Unit 10
339 Massachusetts Ave
ArlingtonMA02474
4 Albert Dr, Unit 11
4 Albert Dr
WoburnMA01801
4 Colonial Village Dr, Unit 9
4 Colonial Village Dr
ArlingtonMA02474
28 Cornell St, Unit 1
28 Cornell St
ArlingtonMA02474
47 Mystic St, Unit 5A
47 Mystic St
ArlingtonMA02474
47 Mystic St, Unit 5A
47 Mystic St
ArlingtonMA02474
995 Massachusetts Ave, Unit 403
995 Massachusetts Ave
ArlingtonMA02476
19 Newland Rd, Unit 2
19 Newland Rd
ArlingtonMA02474
37 Westminster Ave, Unit 2
37 Westminster Ave
ArlingtonMA02474
104 Forest St, Unit 104
104 Forest St
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.
132 Broadway, Unit 1
132 Broadway
ArlingtonMA02474
116 Medford St, Unit 1
116 Medford St
ArlingtonMA02474
47 Webster St, Unit 47
47 Webster St
ArlingtonMA02474
10 Carson Rd
WoburnMA01801
2012 Symmes Cir, Unit 1
2012 Symmes Cir
ArlingtonMA02474
35 Bowdoin St, Unit 35
35 Bowdoin St
ArlingtonMA02474
40 Brattle St
ArlingtonMA02476
3 Day Cir
WoburnMA01801
422 High St, Unit 9
422 High St
MedfordMA02155
177 Central St
StonehamMA02180
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.
9 Circuit St, Unit 1
9 Circuit St
MedfordMA02155
17 Usher Rd, Unit 3
17 Usher Rd
MedfordMA02155
165 Sharon St
MedfordMA02155
260 Boston Ave, Unit 1
260 Boston Ave
MedfordMA02155
258 Boston Ave, Unit 3
258 Boston Ave
MedfordMA02155
227 Boston Ave, Unit 1
227 Boston Ave
MedfordMA02155
165 Gaston St
MedfordMA02155
5 Harris Rd, Unit 1
5 Harris Rd
MedfordMA02155
293 Boston Ave, Unit 2
293 Boston Ave
MedfordMA02155
30 High St, Unit 43
30 High St
MedfordMA02155
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.
5 Harris Rd
MedfordMA02155
207 Boston Ave, Unit A
207 Boston Ave
MedfordMA02155
49 Ripley Rd
MedfordMA02155
10 Greenleaf Ave, Unit 1
10 Greenleaf Ave
MedfordMA02155
217 Arlington St
MedfordMA02155
480 Fulton St, Unit 478
480 Fulton St
MedfordMA02155
217 Arlington St, Unit 1
217 Arlington St
MedfordMA02155
476 Fulton St, Unit 476
476 Fulton St
MedfordMA02155
17 Tesla Ave, Unit 1
17 Tesla Ave
MedfordMA02155
57 Quincy St, Unit 1
57 Quincy St
MedfordMA02155
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.
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 | $2,908 | $2,175 | $5,700 |
| Winchester 3 Bedroom Homes for Rent | $3,678 | $2,800 | $5,500 |
| Winchester 4 Bedroom Homes for Rent | $5,061 | $3,300 | $8,000 |
| Winchester 5 Bedroom Homes for Rent | $6,508 | $2,800 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $8,897 | $5,000 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $7,700 | $7,700 | $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
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 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.
Let everyone know!
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.
Write a Review
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 488 Apartments for Rent in Winchester, MA with pricing that ranges from $1,000 to $9,300. There are also 310 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $1,500 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 $1,500 to $40,000 with an average monthly rent of $4,852.
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 $2,800 to $5,500. Four Bedroom Single-Family rentals are also available starting from $3,300 and Four Bedroom Apartments start at $1,000.
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
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.
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.