Apartments for Rent in Winchester, MA (485 Rentals)

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10 Webster St, Unit 1
$3,700
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,700
Total Monthly Price
$3,700
4 Bedroom Apartment Available Aug 15

10 Webster St, Unit 1

10 Webster StWinchester, MA 01890
Cost Per Sq.Ft.
  • Smoke Free
property at 10-12-12 Webster St

$3,700

Total Monthly Price

Total Monthly Price

Base Rent
$3,700
Total Monthly Price
$3,700

4 Bedroom, 2 Bath Home for Rent

Available Now

10-12-12 Webster St

WinchesterMA01890
property at 926 Main St

$2,900

Total Monthly Price

Total Monthly Price

Base Rent
$2,900
Total Monthly Price
$2,900

2 Bedroom, 1 Bath Home for Rent

Available Sep 1

926 Main St

WinchesterMA01890
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Glenbrook Estates
$2,450 - $2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,450 - $2,900
Total Monthly Price
$2,450 - $2,900
1 to 2 Bedroom Apartments Available Sep 15

Glenbrook Estates

200 Bedford RdWoburn, MA 01801
Family Friendly
  • Verified
  • Customer Reviewed
  • Utilities Included

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

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Hanover Stoneham
Rent Specials
$2,563 - $5,628
Total Monthly Price

Total Monthly Price

Base Rent
$2,563 - $5,628
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Hanover Stoneham

95 Maple StStoneham, MA 02180
Luxury
  • Verified
  • Customer Reviewed
  • Utilities Included
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The Mave
Rent Specials
$2,695 - $5,350
Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,695 - $5,350
Total Monthly Price
Varies
1 to 2 Bedroom Apartments Available Now

The Mave

225 Fallon RdStoneham, MA 02180
Family Friendly
  • Verified
  • Customer Reviewed
  • 3D Tour
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Stonehill Towers
Rent Specials
$2,500 - $3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500 - $3,300
Total Monthly Price
Varies
1 to 2 Bedroom Apartments Available Now

Stonehill Towers

5 Stonehill DrStoneham, MA 02180
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour

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.

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Arlington 360
$2,893 - $8,836
Total Monthly Price

Total Monthly Price

Base Rent
$2,893 - $8,836
Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Arlington 360

4105 Symmes CirArlington, MA 02474
Corporate Housing
  • Verified
  • Customer Reviewed
  • Utilities Included

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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Arlington Gardens
$2,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600
Total Monthly Price
Varies
2 Bedroom Apartments Contact Us For Availability

Arlington Gardens

130 Everett StArlington, MA 02474
Transit Friendly
  • Verified
  • Utilities Included
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51 Winter St, Unit 51
$3,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400
Total Monthly Price
$3,400
4 Bedroom Apartment Available Now

51 Winter St, Unit 51

51 Winter StArlington, MA 02474
Cost Per Sq.Ft.
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249 Boston Ave, Unit 3
$4,450
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,450
Total Monthly Price
$4,450
5 Bedroom Apartment Available Aug 20

249 Boston Ave, Unit 3

249 Boston AveMedford, MA 02155
Cost Per Sq.Ft.

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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48 Nashua St, Unit 2
$2,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500
Total Monthly Price
$2,500
2 Bedroom Apartment Available Now

48 Nashua St, Unit 2

48 Nashua StWoburn, MA 01801
Cost Per Sq.Ft.
  • Smoke Free
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79 Mystic St, Unit #3
$2,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800
Total Monthly Price
$2,800
2 Bedroom Apartment Available Oct 1

79 Mystic St, Unit #3

79 Mystic StArlington, MA 02474
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103 Pleasant St, Unit 2l
$1,895
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,895
Total Monthly Price
$1,895
1 Bedroom Apartment Available Now

103 Pleasant St, Unit 2l

103 Pleasant StWoburn, MA 01801
Affordability
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100 Wildwood Ave, Unit 1
$2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900
Total Monthly Price
$2,900
2 Bedroom Apartment Available Now

100 Wildwood Ave, Unit 1

100 Wildwood AveArlington, MA 02476
Family Friendly
  • Smoke Free

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.

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Winchester, MA Local Guide

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.

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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.

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Top 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.

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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

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See the most popular apartments and homes in Winchester, MA

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Frequently Asked Questions about Winchester

What is the current pricing and availability for apartments for rent in Winchester, MA?

As of today, August 10, 2026, there are currently 485 available Winchester apartments priced from $1,000 to $20,951, with an average monthly rent of $3,455.

What Winchester neighborhoods have the most available apartments?

There are 3 neighborhoods in the Winchester area with available listings as of today. The three neighborhoods with the most options are Kendall Square with 6,122 listings, West End Boston with 5,388 listings, and North Allston with 5,473 listings.

How much are Studio apartments in Winchester?

There are currently 105 Studio Apartments in Winchester with rent ranges from $1,650 to $3,350 with an average price of $2,418.

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 $1,250 to $4,070 with an average monthly rent of $2,691.

What does renting a Two Bedroom Apartment in Winchester cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $2,100 to $5,350. Today's average rental price for Two Bedrooms here is $3,321.

How expensive are Winchester Three Bedroom Apartments?

There are currently 84 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,600 to $6,123 - averaging $3,754 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

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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.

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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.

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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!

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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

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First Apartment Regrets: Real Renters Share What They'd Do Differently

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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.

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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.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

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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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Written by: Robin Stewart

Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.