
4 Bedroom Apartments for Rent in Winchester, MA (40 Rentals)


10-12-12 Webster St

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28 Boston Ave, Unit Modern two floor apartment with old charm

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287 Alewife Brook Pky, Unit 2

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369 Boston Ave, Unit 2

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253 Arlington St, Unit 2

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30 Touro Ave, Unit 30 Touro

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15 Taylor St, Unit 1
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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30 Touro Ave, Unit 1

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282 Boston Ave, Unit 1

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82 Quincy St, Unit 2

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10 Pinkham Rd, Unit 2

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1 Victoria St

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288 Boston Ave, Unit 3

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30 Adams St, Unit 1

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12 Raymond Ave, Unit #1
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76 Curtis St, Unit #1

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56 Gordon St, Unit 1

138 W Adams St

79 Harvard Ave, Unit 2

14 Allen St, Unit 2-3

27 Emery St, Unit 1

100 W Adams St, Unit 2

18 Curtis Ave, Unit 1
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21 Sunset Rd, Unit 2

15 Curtis Ave, Unit 1

27 Fairfax St, Unit 2

27 Fairfax St, Unit 1

31 Grafton St

49 Prospect St

7 Gorham Rd

54 Clark St
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44 Orchard St

28 Sunset Rd

3 Burlington St

Brightly Renovated 4-Bed / 2-Bath • 1,800 sq

61 Warren Ave R

18 Belknap St

43 Salem St

Mountain View Terrace
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Winchester, MA Local Guide

How much does it cost to rent an apartment in Winchester?
| Bedroom | Average Price | Cheapest Price | Highest Price |
|---|---|---|---|
| Winchester Studio Apartments | $2,415 | $1,650 | $3,350 |
| Winchester 1 Bedroom Apartments | $2,683 | $1,695 | $4,170 |
| Winchester 2 Bedroom Apartments | $3,359 | $2,200 | $5,440 |
| Winchester 3 Bedroom Apartments | $3,675 | $2,600 | $5,994 |
Winchester 4 Bedroom Apartments | $4,389 | $3,300 | $6,000 |
| Winchester 5 Bedroom Apartments | $6,869 | $4,450 | $10,000+ |
Browse Top Apartments in Winchester
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Winchester, MA Local Guide
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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.
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.
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.
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
How much are Studio apartments in Winchester?
There are currently 106 Studio Apartments in Winchester with rent ranges from $1,650 to $3,350 with an average price of $2,415.
What is the current price range for One Bedroom Winchester Apartments for rent?
Today's rental pricing for One Bedroom Apartments in Winchester ranges from $1,695 to $4,170 with an average monthly rent of $2,683.
What does renting a Two Bedroom Apartment in Winchester cost?
The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,200 to $5,440. Today's average rental price for Two Bedrooms here is $3,359.
How expensive are Winchester Three Bedroom Apartments?
There are currently 78 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,600 to $5,994 - averaging $3,675 for the location.
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

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!

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

Renters Insurance 101: What It Is, What It Covers, and Why You Need It
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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.

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
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There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

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Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.