Luxury Apartments for Rent in Winchester, MA (221 Rentals)

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The most luxurious Apartments in Winchester with high-end amenities, features, and finishes.

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10 Webster St, Unit 1
$3,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,900
Total Monthly Price
$3,900
4 Bedroom Apartment Available Now

10 Webster St, Unit 1

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

$3,900

Total Monthly Price

Total Monthly Price

Base Rent
$3,900
Total Monthly Price
$3,900

4 Bedroom, 2 Bath Home for Rent

Available Now

10-12-12 Webster St

WinchesterMA01890
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77 Fairfax St
$2,100 - $3,300
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,100 - $3,300
Total Monthly Price
$2,100 - $3,300
Studio to 2 Bedroom Apartment Available Now

77 Fairfax St

77 Fairfax StSomerville, MA 02144
Cost Per Sq.Ft.

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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Hanover Stoneham
Rent Specials
$2,256 - $5,628
Total Monthly Price

Total Monthly Price

Base Rent
$2,256 - $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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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 Aug 15

Glenbrook Estates

200 Bedford RdWoburn, MA 01801
Family Friendly
  • Verified
  • Customer Reviewed
  • Utilities Included
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Stonehill Towers
$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
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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.
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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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67 Sterling St
$2,600 - $2,800
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600 - $2,800
Total Monthly Price
$2,600 - $2,800
3 Bedroom Apartment Available Now

67 Sterling St

67 Sterling StSomerville, MA 02144
Affordability
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124 Forest St, Unit 3R
$2,600
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,600
Total Monthly Price
$2,600
3 Bedroom Apartment Available Now

124 Forest St, Unit 3R

124 Forest StMedford, MA 02155
Cost Per Sq.Ft.
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The Mave
$2,680 - $5,440
Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,680 - $5,440
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

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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18 Silk St
$2,825
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,825
Total Monthly Price
$2,825
Studio to 2 Bedroom Apartment Available Now

18 Silk St

18 Silk StArlington, MA 02474
Cost Per Sq.Ft.
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Arlington 360
$2,893 - $8,975
Total Monthly Price

Total Monthly Price

Base Rent
$2,893 - $8,975
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
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38 Rawson Rd, Unit 2
$2,900
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,900
Total Monthly Price
$2,900
2 Bedroom Apartment Available Sep 1

38 Rawson Rd, Unit 2

38 Rawson RdArlington, MA 02474
Cost Per Sq.Ft.
  • Smoke Free
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14 Irvington Rd, 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 Sep 1

14 Irvington Rd, Unit 1

14 Irvington RdSomerville, MA 02144
Affordability
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14 Irvington Rd, 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 Sep 1

14 Irvington Rd, Unit 1

14 Irvington RdSomerville, MA 02144
Affordability
  • Smoke Free

Boston Major Employer Neighborhood Guide: Living Near UMass, MGH, & 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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1 Victoria St
$3,100 - $4,500
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100 - $4,500
Total Monthly Price
$3,100 - $4,500
2 to 4 Bedroom Apartment Available Now

1 Victoria St

1 Victoria StSomerville, MA 02144
Cost Per Sq.Ft.
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97 W Quincy St, Unit 1
$3,195
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,195
Total Monthly Price
$3,195
2 Bedroom Apartment Available Aug 31

97 W Quincy St, Unit 1

97 W Quincy StSomerville, MA 02144
Cost Per Sq.Ft.

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

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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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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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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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 $2,437.

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 $2,688.

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 $3,361.

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 $3,663 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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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

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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

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Hi! I’m Amelia, your ApartmentHomeLiving.com expert for Boston, and I’m excited to help you find your next home!

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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.

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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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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

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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.

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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.