37 Rumford St
WinchesterMA01890
Luxury Homes for Rent in Winchester, MA (425 Rentals)
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
37 Rumford St
WinchesterMA01890
848 Main St
WinchesterMA01890
247 Washington St, Unit 13
247 Washington St
WinchesterMA01890
200 Swanton St, Unit 239
200 Swanton St
WinchesterMA01890
343 Washington St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
4 Norwood St
WinchesterMA01890
34 Glen Rd
WinchesterMA01890
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.
22 Amberwood Dr
WinchesterMA01890
23 Jefferson Rd
WinchesterMA01890
31 Coolidge Rd
WinchesterMA01890
72 Holland St
WinchesterMA01890
271 Washington St
WinchesterMA01890
37 Rumford St
WinchesterMA01890
171 Swanton St
WinchesterMA01890
67 Church St
WinchesterMA01890
38 Florence St
WinchesterMA01890
2 George Rd
WinchesterMA01890
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.
40 Florence St
WinchesterMA01890
247 Washington St
WinchesterMA01890
273 Cross St
WinchesterMA01890
200 Swanton St
WinchesterMA01890
29 Harvard Ave, Unit 33
29 Harvard Ave
MedfordMA02155
100 Emerson Gardens Rd, Unit 100
100 Emerson Gardens Rd
LexingtonMA02420
75 Woodfall Rd
BelmontMA02478
34 Chetwynd Rd, Unit BF
34 Chetwynd 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.
45 Wellesley Rd
BelmontMA02478
82 Sharon St
MedfordMA02155
80 Curtis St, Unit 1
80 Curtis St
SomervilleMA02144
16 Chetwynd Rd
SomervilleMA02144
120 Jerome St, Unit 120
120 Jerome St
MedfordMA02155
232 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
232 Fulton St, Unit T
232 Fulton St
MedfordMA02155
120 Jerome St, Unit T
120 Jerome St
MedfordMA02155
232 Fulton St, Unit 232
232 Fulton St
MedfordMA02155
120 Jerome St
MedfordMA02155
120 Jerome St
MedfordMA02155
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
17 Tesla Ave, Unit 2
17 Tesla Ave
MedfordMA02155
17 Tesla Ave, Unit 2
17 Tesla Ave
MedfordMA02155
122 Jerome St, Unit 1
122 Jerome St
MedfordMA02155
230 Fulton St, Unit 1
230 Fulton St
MedfordMA02155
5 Hamilton Rd, Unit 2
5 Hamilton Rd
SomervilleMA02144
3 Hamilton Rd, Unit 2
3 Hamilton Rd
SomervilleMA02144
3 Hamilton Rd
SomervilleMA02144
70 Curtis St, Unit 1
70 Curtis St
SomervilleMA02144
80 Curtis St
SomervilleMA02144
16 Chetwynd Rd, Unit 16
16 Chetwynd Rd
SomervilleMA02144
16 Chetwynd Rd, Unit 1
16 Chetwynd Rd
SomervilleMA02144
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 | $3,192 | $2,225 | $6,400 |
| Winchester 3 Bedroom Homes for Rent | $3,810 | $3,000 | $5,950 |
| Winchester 4 Bedroom Homes for Rent | $5,064 | $3,300 | $8,900 |
| Winchester 5 Bedroom Homes for Rent | $6,645 | $4,225 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $7,958 | $5,945 | $10,000+ |
| Winchester 7 Bedroom Homes for Rent | $8,231 | $6,995 | $10,000+ |
Browse Top Homes for Rent in Winchester
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Winchester, MA Local Guide
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Quick Rent Budget Calculator
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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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Frequently Asked Questions about Winchester
What type of rentals are currently available in Winchester?
There are currently 803 Apartments for Rent in Winchester, MA with pricing that ranges from $1,450 to $10,400. There are also 471 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $920 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 $920 to $40,000 with an average monthly rent of $4,869.
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 $9,547, while Three Bedroom Homes, Condos, and Townhomes for rent range from $3,000 to $5,950. 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.