Luxury Apartments for Rent in Winchester, MA (305 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

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

close
View Me
10 Webster St, Unit 1
$3,700

Total Monthly Price

Base Rent$3,700

Total Monthly Price$3,700
12 Month Lease Term
4 Bedroom Apartment Available Now

10 Webster St, Unit 1

10 Webster StWinchester, MA 01890
Cost Per Sq.Ft.
  • Smoke Free
property at 24 Lebanon St
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
2 Bedroom, 1 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

24 Lebanon St

WinchesterMA01890
property at 303 Washington St
$3,500

Total Monthly Price

Base Rent$3,500

Total Monthly Price$3,500
3 Bedroom, 1 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

303 Washington St

WinchesterMA01890
property at 10-12-12 Webster St
$3,700

Total Monthly Price

Base Rent$3,700

Total Monthly Price$3,700
4 Bedroom, 2 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

10-12-12 Webster St

WinchesterMA01890
property at 7 Park Ave
$4,100

Total Monthly Price

Base Rent$4,100

Total Monthly Price$4,100
4 Bedroom, 2 Bath Home for Rent
Available Now

7 Park Ave

WinchesterMA01890
property at 79 Church St
$4,400

Total Monthly Price

Base Rent$4,400

Total Monthly Price$4,400
3 Bedroom, 1.5 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

79 Church St

WinchesterMA01890
close
View Me
HCA - 840-846 Mass Ave
$1,775 - $2,900

Total Monthly Price

Base Rent$1,775 - $2,900

Total Monthly Price$1,775 - $2,900
24 Month Lease Term
Studio to 4 Bedroom Apartments Available Now

HCA - 840-846 Mass Ave

840 Massachusetts AveArlington, MA 02476
Affordability
  • Verified
  • Smoke Free

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

close
View Me
Leisure Lane Apartments
$1,810 - $2,585

Total Monthly Price

Base Rent$1,810 - $2,585

Total Monthly Price$1,810 - $2,585
12 Month Lease Term
Studio to 2 Bedroom Apartments Available Now

Leisure Lane Apartments

100 Leisure LnStoneham, MA 02180
Affordability
  • Verified
  • Customer Reviewed
  • Utilities Included
close
View Me
Brattle Drive Apartments
Rent Specials
$1,900 - $2,550

Total Monthly Price

Base Rent$1,900 - $2,550

Total Monthly Price$1,900 - $2,550
12 Month Lease Term
Studio to 2 Bedroom Apartments Available Now

Brattle Drive Apartments

0-12 Brattle DrArlington, MA 02474
Affordability
  • Verified
  • Customer Reviewed
  • Utilities Included
close
View Me
Mill Street Gardens
Rent Specials
$1,950 - $2,600

Total Monthly Price

Base Rent$1,950 - $2,600

Total Monthly Price$1,950 - $2,600
12 Month Lease Term
1 to 2 Bedroom Apartments Available Now

Mill Street Gardens

57 Mill StWoburn, MA 01801
Pet Friendly
  • Verified
  • Customer Reviewed
  • Utilities Included
close
View Me
Old Colony Apartments
$2,100 - $2,500

Total Monthly Price

Base Rent$2,100 - $2,500

Total Monthly Price$2,100 - $2,500
12 Month Lease Term
1 to 2 Bedroom Apartments Available Now

Old Colony Apartments

1-17 Old Colony LnArlington, MA 02476
Affordability
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
Tudor Glen Village
$2,195 - $3,295

Total Monthly Price

Base Rent$2,195 - $3,295

Total Monthly Price$2,195 - $3,295
1 to 2 Bedroom Apartments Available Now

Tudor Glen Village

111 Locust StWoburn, MA 01801
Affordability
  • Verified
  • Utilities Included
  • 3D Tour
close
View Me
369 Boston Ave
$2,200 - $3,800

Total Monthly Price

Base Rent$2,200 - $3,800

Total Monthly Price$2,200 - $3,800
12 Month Lease Term
2 to 4 Bedroom Apartment Available Now

369 Boston Ave

369 Boston AveMedford, MA 02155
Affordability
close
View Me
Mill Street Heights
$2,400 - $3,075

Total Monthly Price

Base Rent$2,400 - $3,075

Total Monthly Price$2,400 - $3,075
12 Month Lease Term
2 Bedroom Apartments Available Soon

Mill Street Heights

59 Mill StWoburn, MA 01801
Pet Friendly
  • Verified
  • Utilities Included
  • 3D Tour
close
View Me
Glenbrook Estates
Rent Specials
$2,450 - $2,900

Total Monthly Price

Base Rent$2,450 - $2,900

Total Monthly Price$2,450 - $2,900
12 Month Lease Term
1 to 2 Bedroom Apartments Available Sep 15

Glenbrook Estates

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

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.

close
View Me
Stonehill Towers
Rent Specials
$2,500 - $3,350

Total Monthly Price

Base Rent$2,500 - $3,350

Total Monthly PriceVaries
12 Month Lease Term
1 to 2 Bedroom Apartments Available Sep 15

Stonehill Towers

5 Stonehill DrStoneham, MA 02180
Corporate Housing
  • Verified
  • Customer Reviewed
  • 3D Tour
close
View Me
14 Irvington Rd, Unit 1
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
12 Month Lease Term
2 Bedroom Apartment Available Now

14 Irvington Rd, Unit 1

14 Irvington RdSomerville, MA 02144
Affordability
  • Smoke Free
close
View Me
60 Adams St, Unit 2
$2,500

Total Monthly Price

Base Rent$2,500

Total Monthly Price$2,500
12 Month Lease Term
2 Bedroom Apartment Available Now

60 Adams St, Unit 2

60 Adams StMedford, MA 02155
Affordability
  • Smoke Free
close
View Me
Hanover Stoneham
Rent Specials
$2,567 - $6,718

Total Monthly Price

Base Rent$2,567 - $6,718

Total Monthly Price$2,567 - $6,718
Studio to 3 Bedroom Apartments Available Now

Hanover Stoneham

95 Maple StStoneham, MA 02180
Luxury
  • Verified
  • Customer Reviewed
  • Utilities Included
close
View Me
The Mave
Rent Specials
$2,640 - $4,930

Total Monthly Price

Base Rent$2,640 - $4,930

Total Monthly PriceVaries
1 Month Lease Term
1 to 2 Bedroom Apartments Available Now

The Mave

225 Fallon RdStoneham, MA 02180
Family Friendly
  • Verified
  • Customer Reviewed
  • 3D Tour

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.

close
View Me
44 Montvale Avenue
$2,700 - $2,800

Total Monthly Price

Base Rent$2,700 - $2,800

Total Monthly Price$2,700 - $2,800
1 Month Lease Term
1 Bedroom Apartments Available Now

44 Montvale Avenue

44 Montvale AveWoburn, MA 01801
Furnished
  • Verified
  • Utilities Included
  • 3D Tour
close
View Me
Arlington 360
$2,812 - $8,675

Total Monthly Price

Base Rent$2,812 - $8,675

Total Monthly PriceVaries
Studio to 3 Bedroom Apartments Available Now

Arlington 360

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

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.

close
View Me
29 Capen St
$3,000 - $5,600

Total Monthly Price

Base Rent$3,000 - $5,600

Total Monthly Price$3,000 - $5,600
12 Month Lease Term
2 to 4 Bedroom Apartment Available Jun 1, 2027

29 Capen St

29 Capen StMedford, MA 02155
Cost Per Sq.Ft.
close
View Me
132 W Adams St, Unit 132
$3,000

Total Monthly Price

Base Rent$3,000

Total Monthly Price$3,000
12 Month Lease Term
2 Bedroom Apartment Available Oct 1

132 W Adams St, Unit 132

132 W Adams StSomerville, MA 02144
Affordability
  • Smoke Free
close
View Me
1 Victoria St
$3,100 - $4,500

Total Monthly Price

Base Rent$3,100 - $4,500

Total Monthly Price$3,100 - $4,500
12 Month Lease Term
2 to 4 Bedroom Apartment Available Now

1 Victoria St

1 Victoria StSomerville, MA 02144
Cost Per Sq.Ft.
close
View Me
97 W Quincy St, Unit 1
$3,195

Total Monthly Price

Base Rent$3,195

Total Monthly Price$3,195
12 Month Lease Term
2 Bedroom Apartment Available Now

97 W Quincy St, Unit 1

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

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.

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.

Read Article
Decorative image

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 Article

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

Read Article
Decorative image

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
Decorative image

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.

decorative image of people with a giant lease agreement

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winchester, MA Rentals by Map

View Map
Winchester, MA Apartments Map
View Map
Winchester, MA Rental Homes Map

Frequently Asked Questions about Winchester

How much are Studio apartments in Winchester?

There are currently 98 Studio Apartments in Winchester with rent ranges from $1,750 to $3,448 with an average price of $2,397.

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 $825 to $4,534 with an average monthly rent of $2,643.

What does renting a Two Bedroom Apartment in Winchester cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winchester range from $1,100 to $5,401. Today's average rental price for Two Bedrooms here is $3,282.

How expensive are Winchester Three Bedroom Apartments?

There are currently 92 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,718 - averaging $3,803 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

decorative image for Moving to Boston Without Losing Your Mind: A Renter’s Guide to a Smooth Move article

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.

decorative image for What It Really Costs to Live in Boston: A Local Renter's Guide article

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.

decorative image for Close to Boston, Easier to Rent: Your Guide to 5 Key Neighboring Cities article

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!

decorative image for Top Short-Term Rental Neighborhoods in Boston: Tips from a Local Expert   article

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

decorative image for Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My! article

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.

decorative image for Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags   article

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.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

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.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

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.