115 Washington St
WinchesterMA01890
Luxury Homes for Rent in Winchester, MA (231 Rentals)
The most luxurious Homes in Winchester with high-end amenities, features, and finishes.
200 Swanton St, Unit 705
200 Swanton St
WinchesterMA01890
63-65 Harvard St
WinchesterMA01890
7 Ridge St
WinchesterMA01890
5 Quigley Ct
WinchesterMA01890
666 Main St
WinchesterMA01890
60 Lake St
WinchesterMA01890
28 East St
WinchesterMA01890
63 Holland St
WinchesterMA01890
22 Baldwin St
WinchesterMA01890
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Moving to Boston? Discover how to handle unique rental rules, avoid common moving day pitfalls, and prepare for your first winter in the city
79 Bacon St
WinchesterMA01890
111 Highland Ave
WinchesterMA01890
161 Highland Ave
WinchesterMA01890
10 Bellevue Ave
WinchesterMA01890
21 Royall St
MedfordMA02155
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
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$2,5002 Bedroom Apartments Available Oct 1
76 Mill St, Unit 5
76 Mill StWoburn, MA 01801
35 Woods Ave
SomervilleMA02144
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$2,5002 Bedroom Apartments Available Now
78 Mill St, Unit 1
78 Mill StWoburn, MA 01801
100 Ledgewood Dr, Unit 412
100 Ledgewood Dr
StonehamMA02180
Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!
Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.
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$2,5002 Bedroom Apartments Available Now
62 Mill St, Unit 6
62 Mill StWoburn, MA 01801
100 High St
MedfordMA02155
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$2,5002 Bedroom Apartments Available Now
70 Mill St, Unit 3
70 Mill StWoburn, MA 01801
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$2,5002 Bedroom Apartments Available Now
14 Irvington Rd
14 Irvington RdSomerville, MA 02144
137 Franklin St
StonehamMA02180
202 Central St
StonehamMA02180
30 Early Ave
MedfordMA02155
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$2,6002 Bedroom Apartments Available Now
60 Mill St, Unit 11
60 Mill StWoburn, MA 01801
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$2,6002 Bedroom Apartments Available Now
66 Mill St, Unit 1
66 Mill StWoburn, MA 01801
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$2,6002 Bedroom Apartments Available Now
56 Mill St, Unit 1
56 Mill StWoburn, MA 01801
What It Really Costs to Live in Boston: A Local Renter’s Guide
Thinking of moving to Boston? Discover the real cost of living in the city. Our local expert guide breaks down rent, hidden utility costs, transportation tips, and neighborhood tradeoffs to help you budget smarter.
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$2,6002 Bedroom Apartments Available Now
54 Mill St, Unit 6
54 Mill StWoburn, MA 01801
177 Central St
StonehamMA02180
35 Sunnyside Ave
ArlingtonMA02474
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$2,6252 Bedroom Apartments Available Sep 15
104 Conwell Ave, Unit #1
104 Conwell AveSomerville, MA 02144
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$2,6502 Bedroom Apartments Available Sep 15
276 Massachusetts Ave, Unit #203
276 Massachusetts AveArlington, MA 02474
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$2,7003 Bedroom Apartments Available Now
124 Forest St, Unit 3
124 Forest StMedford, MA 02155
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$2,7502 Bedroom Apartments Available Now
7 Totman Dr, Unit 4
7 Totman DrWoburn, MA 01801
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$2,7502 Bedroom Apartments Available Now
30 Hume Ave, Unit #2
30 Hume AveMedford, MA 02155
125 Pleasant St, Unit 306
125 Pleasant St
ArlingtonMA02476
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$2,7501 Bedroom Apartments Available Now
32 Walnut St
32 Walnut StArlington, MA 02476
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Find your perfect apartment outside Boston. We review Quincy, Braintree, Malden, Somerville, and Lynn, covering local hotspots, commute options, and available rental types.
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$2,8002 Bedroom Apartments Available Now
Plus Fees
92 Sylvia St
92 Sylvia StArlington, MA 02474
61 Wright St
StonehamMA02180
1 Colonial Village Dr
ArlingtonMA02474
159 Main St
StonehamMA02180
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$2,8002 Bedroom Apartments Available Now
Plus Fees
100 North St
100 North StMedford, MA 02155
169 Franklin St
StonehamMA02180
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$2,8002 Bedroom Apartments Available Now
2500 Mystic Valley Pkwy, Unit #805
2500 Mystic Valley PkwyMedford, MA 02155
46 Clewley Rd, Unit 3
46 Clewley Rd
MedfordMA02155
898 Massachusetts Ave, Unit 32
898 Massachusetts Ave
ArlingtonMA02476
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$2,8501 Bedroom Apartments Available Oct 2
898 Massachusetts Ave, Unit 32
898 Massachusetts AveArlington, MA 02476
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
Showing Results 1-50, Page 1 of 5
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 | $2,996 | $1,000 | $4,750 |
| Winchester 3 Bedroom Homes for Rent | $3,912 | $2,800 | $6,500 |
| Winchester 4 Bedroom Homes for Rent | $5,150 | $3,450 | $8,750 |
| Winchester 5 Bedroom Homes for Rent | $8,353 | $4,750 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $9,609 | $6,495 | $10,000+ |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
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Winchester, MA Local Guide
- Winchester Neighborhoods
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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.
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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.
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.
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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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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 445 Apartments for Rent in Winchester, MA with pricing that ranges from $825 to $18,885. There are also 283 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $800 to $18,000.
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 $800 to $18,000 with an average monthly rent of $4,028.
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 $6,718, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,450 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
Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
What It Really Costs to Live in Boston: A Local Renter's Guide
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com Local Expert for Boston.
Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities
Written by: Amelia Ramstead
Hello! I’m Amelia, your ApartmentHomeLiving.com expert for Boston!
Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert
Written by: Amelia Ramstead
Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!
Articles, How-To's, and Tips
Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.