40 Florence St, Unit 2
40 Florence St
WinchesterMA01890
3 Bedroom Homes for Rent in Winchester, MA (101 Rentals)
2 George Rd
WinchesterMA01890
3 Wainwright Rd
WinchesterMA01890
51 Conn St
WoburnMA01801
12 Pinkham Rd
MedfordMA02155
12 Pinkham Rd, Unit 1
12 Pinkham Rd
MedfordMA02155
56 Gordon St, Unit 1
56 Gordon St
SomervilleMA02144
12 Pinkham Rd, Unit 1
12 Pinkham Rd
MedfordMA02155
12 Pinkham Rd, Unit 1
12 Pinkham Rd
MedfordMA02155
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.
20 Burget Ave, Unit T
20 Burget Ave
MedfordMA02155
333 Alewife Brook Pky
SomervilleMA02144
37 Westminster Ave, Unit 2
37 Westminster Ave
ArlingtonMA02474
123 Forest St, Unit 2
123 Forest St
MedfordMA02155
49 Conwell Ave
SomervilleMA02144
65 Sterling St, Unit 1
65 Sterling St
SomervilleMA02144
260 Boston Ave, Unit 1
260 Boston Ave
MedfordMA02155
112 College Ave, Unit U1
112 College Ave
MedfordMA02155
258 Boston Ave, Unit 2
258 Boston Ave
MedfordMA02155
258 Boston Ave, Unit 3
258 Boston Ave
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.
67 Sterling St
SomervilleMA02144
67 Sterling St
SomervilleMA02144
116 Medford St, Unit 1
116 Medford St
ArlingtonMA02474
8 Vera Ln
StonehamMA02180
59 Quincy St
MedfordMA02155
75 Lyman Ave, Unit 1
75 Lyman Ave
MedfordMA02155
59 Quincy St
MedfordMA02155
75 Lyman Ave
MedfordMA02155
91 Williams St, Unit 91
91 Williams St
ArlingtonMA02476
32 Irvington Rd
SomervilleMA02144
49 Conwell Ave, Unit 2
49 Conwell Ave
SomervilleMA02144
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.
49 Conwell Ave, Unit 2
49 Conwell Ave
SomervilleMA02144
49 Conwell Ave, Unit 2
49 Conwell Ave
SomervilleMA02144
49 Conwell Ave, Unit Conwell Ave
49 Conwell Ave
SomervilleMA02144
77 Forest St, Unit 2
77 Forest St
MedfordMA02155
59 Quincy St
MedfordMA02155
2 High St, Unit 2
2 High St
SomervilleMA02144
2 High St, Unit 1
2 High St
SomervilleMA02144
224 Arlington St, Unit 224
224 Arlington St
MedfordMA02155
106 W Adams St, Unit 1
106 W Adams St
SomervilleMA02144
3 Hamilton Rd, Unit 1
3 Hamilton Rd
SomervilleMA02144
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.
287 Alewife Brook Pky, Unit 2
287 Alewife Brook Pky
SomervilleMA02144
21 Jerome St
MedfordMA02155
32 Irvington Rd
SomervilleMA02144
21 Belknap St, Unit 2
21 Belknap St
SomervilleMA02144
32 Irvington Rd
SomervilleMA02144
30 Chetwynd Rd, Unit 1
30 Chetwynd Rd
SomervilleMA02144
290 Boston Ave, Unit 2
290 Boston Ave
MedfordMA02155
59 Quincy St, Unit 1
59 Quincy St
MedfordMA02155
59 Quincy St, Unit 59
59 Quincy St
MedfordMA02155
44 Upland Rd, Unit 1
44 Upland Rd
SomervilleMA02144
Boston's Best Affordable Neighborhoods
Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead
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 Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Winchester 2 Bedroom Homes for Rent | $3,236 | $2,225 | $6,400 |
| Winchester 3 Bedroom Homes for Rent | $3,793 | $3,000 | $6,000 |
| Winchester 4 Bedroom Homes for Rent | $5,111 | $3,300 | $9,500 |
| Winchester 5 Bedroom Homes for Rent | $6,504 | $4,225 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $7,918 | $5,995 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,798 | $6,995 | $10,000+ |
Browse Top Homes for Rent in Winchester
Explore Winchester
Winchester, MA Local Guide
- Winchester Neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
- School Districts
Quick 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
Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 740 Apartments for Rent in Winchester, MA with pricing that ranges from $1,595 to $10,400. There are also 528 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $950 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 $950 to $40,000 with an average monthly rent of $4,961.
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 $9,484, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $6,000. 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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.