60 Lake St
WinchesterMA01890
Homes for Rent in Winchester, MA (270 Rentals)
200 Swanton St
WinchesterMA01890
115 Washington St
WinchesterMA01890
63-65 Harvard St
WinchesterMA01890
7 Ridge St
WinchesterMA01890
5 Quigley Ct
WinchesterMA01890
666 Main St
WinchesterMA01890
60 Lake St
WinchesterMA01890
34 Charles Rd
WinchesterMA01890
28 East 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
7 Conant Rd
WinchesterMA01890
79 Bacon St
WinchesterMA01890
111 Highland Ave
WinchesterMA01890
161 Highland Ave
WinchesterMA01890
10 Bellevue Ave
WinchesterMA01890
200 Swanton St, Unit 708
200 Swanton St
WinchesterMA01890
200 Swanton St, Unit 313
200 Swanton St
WinchesterMA01890
63 Holland St
WinchesterMA01890
200 Swanton St, Unit 240
200 Swanton St
WinchesterMA01890
125 Pleasant St, Unit 306
125 Pleasant St
ArlingtonMA02476
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.
40 Brattle St
ArlingtonMA02476
74 Sharon St
MedfordMA02155
5 Quincy St, Unit 5 Quincy St
5 Quincy St
MedfordMA02155
44 Adams St
MedfordMA02155
2 Albert Dr, Unit 10
2 Albert Dr
WoburnMA01801
159 Bedford Rd
WoburnMA01801
4 Senator Rd
WoburnMA01801
3 Day Cir
WoburnMA01801
1033 Massachusetts Ave, Unit 10
1033 Massachusetts Ave
ArlingtonMA02476
3 Colonial Village Dr, Unit 10
3 Colonial Village Dr
ArlingtonMA02474
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.
47 Mystic St, Unit 5A
47 Mystic St
ArlingtonMA02474
4 Park St
ArlingtonMA02474
72 Harlow St, Unit 72
72 Harlow St
ArlingtonMA02474
459 Appleton St
ArlingtonMA02476
164 Mystic Valley Pky, Unit 164 Mystic Valley Pkwy
164 Mystic Valley Pky
ArlingtonMA02474
24 Oxford St, Unit 1
24 Oxford St
ArlingtonMA02474
15 Campbell Rd
ArlingtonMA02476
21 Royall St
MedfordMA02155
6 Boston Ave
MedfordMA02155
98 Sharon St
MedfordMA02155
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.
289 Elm St, Unit 14
289 Elm St
MedfordMA02155
46 Clewley Rd, Unit 3
46 Clewley Rd
MedfordMA02155
31 Lyman Ave
MedfordMA02155
53 Oakland St, Unit TWO
53 Oakland St
MedfordMA02155
2500 Mystic Valley Pky, Unit 702
2500 Mystic Valley Pky
MedfordMA02155
112 College Ave, Unit 1##
112 College Ave
MedfordMA02155
288 Boston Ave
MedfordMA02155
34 Salem St, Unit 201
34 Salem St
MedfordMA02155
116 Grove St
MedfordMA02155
14 Sturtevant Ter, Unit 1
14 Sturtevant Ter
MedfordMA02155
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
Showing Results 1-50, Page 1 of 6
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 | $3,844 | $2,900 | $6,000 |
| Winchester 4 Bedroom Homes for Rent | $5,066 | $3,450 | $8,750 |
| Winchester 5 Bedroom Homes for Rent | $7,976 | $4,000 | $10,000+ |
| Winchester 6 Bedroom Homes for Rent | $10,450 | $7,500 | $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
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Winchester, MA Local Guide
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A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.
Read Article
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.
Read Article
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
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Real 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.
Read Article
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.
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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 440 Apartments for Rent in Winchester, MA with pricing that ranges from $825 to $12,539. There are also 280 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $795 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 $795 to $18,000 with an average monthly rent of $3,905.
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 $7,312, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,000. 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
How Commercial-to-Residential Property Conversions Help the Housing Crisis
Written by: Robin Stewart
Many housing markets throughout America share a common complaint: a lack of affordable rental properties.
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.