5 Bedroom Apartments for Rent near Winchester, MA (44 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
close
View Me
17 Tesla Ave, Unit 1R
$7,600

Total Monthly Price

Base Rent$7,600

Total Monthly Price$7,600
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

17 Tesla Ave, Unit 1R

17 Tesla AveMedford, MA 02155
close
View Me
15 Curtis Ave
$7,000

Total Monthly Price

Base Rent$5,500 - $7,000

Total Monthly Price$5,500 - $7,000
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

15 Curtis Ave

15 Curtis AveSomerville, MA 02144
Cost Per Sq.Ft.
close
View Me
111 Hillsdale Rd
$7,000

Total Monthly Price

Base Rent$7,000 - $8,600

Total Monthly Price$7,000 - $8,600
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

111 Hillsdale Rd

111 Hillsdale RdSomerville, MA 02144
Cost Per Sq.Ft.
close
View Me
17 Tesla Ave, Unit 1
$7,600

Total Monthly Price

Base Rent$7,600

Total Monthly Price$7,600
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

17 Tesla Ave, Unit 1

17 Tesla AveMedford, MA 02155
Cost Per Sq.Ft.
close
View Me
24 Chetwynd Rd, Unit 2
$6,150

Total Monthly Price

Base Rent$6,150

Total Monthly Price$6,150
12 Month Lease Term
5 Bedroom Apartment Available Now

24 Chetwynd Rd, Unit 2

24 Chetwynd RdSomerville, MA 02144
Cost Per Sq.Ft.
close
View Me
17 Tesla Ave, Unit 1
$7,600

Total Monthly Price

Base Rent$7,600

Total Monthly Price$7,600
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

17 Tesla Ave, Unit 1

17 Tesla AveMedford, MA 02155
Cost Per Sq.Ft.

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
249 Boston Ave, Unit 3
$4,450

Total Monthly Price

Base Rent$4,450

Total Monthly Price$4,450
12 Month Lease Term
5 Bedroom Apartment Available Now

249 Boston Ave, Unit 3

249 Boston AveMedford, MA 02155
Cost Per Sq.Ft.
close
View Me
123 Winthrop St, Unit 1
$5,750

Total Monthly Price

Base Rent$5,750

Total Monthly Price$5,750
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

123 Winthrop St, Unit 1

123 Winthrop StMedford, MA 02155
close
View Me
21 Emery St, Unit 1
$6,950

Total Monthly Price

Base Rent$6,950

Total Monthly Price$6,950
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

21 Emery St, Unit 1

21 Emery StMedford, MA 02155
close
View Me
14 Fairmount St, Unit 1
$6,250

Total Monthly Price

Base Rent$6,250

Total Monthly Price$6,250
12 Month Lease Term
5 Bedroom Apartment Available Now

14 Fairmount St, Unit 1

14 Fairmount StMedford, MA 02155
close
View Me
20 Sunset Rd
$7,200

Total Monthly Price

Base Rent$4,200 - $7,200

Total Monthly Price$4,200 - $7,200
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

20 Sunset Rd

20 Sunset RdSomerville, MA 02144
Cost Per Sq.Ft.
  • Smoke Free

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.

close
View Me
47 Pearl St, Unit 2
$6,750

Total Monthly Price

Base Rent$6,750

Total Monthly Price$6,750
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

47 Pearl St, Unit 2

47 Pearl StMedford, MA 02155
  • Smoke Free
close
View Me
47 Pearl St, Unit 2
$6,950

Total Monthly Price

Base Rent$6,950

Total Monthly Price$6,950
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

47 Pearl St, Unit 2

47 Pearl StMedford, MA 02155
close
View Me
260 Boston Ave, Unit 2
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
12 Month Lease Term
5 Bedroom Apartment Available Now

260 Boston Ave, Unit 2

260 Boston AveMedford, MA 02155
close
View Me
119 North St, Unit 2
$4,800

Total Monthly Price

Base Rent$4,800

Total Monthly Price$4,800
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

119 North St, Unit 2

119 North StSomerville, MA 02144
close
View Me
23 Edison Ave, Unit 2
$7,500

Total Monthly Price

Base Rent$7,500

Total Monthly Price$7,500
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

23 Edison Ave, Unit 2

23 Edison AveMedford, MA 02155
close
View Me
42 Sunset Rd, Unit 2
$7,250

Total Monthly Price

Base Rent$7,250

Total Monthly Price$7,250
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

42 Sunset Rd, Unit 2

42 Sunset RdSomerville, MA 02144
close
View Me
43 Teele Ave
$7,000

Total Monthly Price

Base Rent$5,600 - $7,000

Total Monthly Price$5,600 - $7,000
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

43 Teele Ave

43 Teele AveSomerville, 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.

close
View Me
15 Curtis Ave
$7,000

Total Monthly Price

Base Rent$5,500 - $7,000

Total Monthly Price$5,500 - $7,000
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

15 Curtis Ave

15 Curtis AveSomerville, MA 02144
Cost Per Sq.Ft.
close
View Me
136 Burget Ave
$7,000

Total Monthly Price

Base Rent$3,600 - $7,000

Total Monthly Price$3,600 - $7,000
12 Month Lease Term
5 Bedroom Apartment Available Jun 1, 2027

136 Burget Ave

136 Burget 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.

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.

property at 3 Chapel Way
$8,190

Total Monthly Price

Base Rent$7,786
Required Monthly Fees$404

Total Monthly Price$8,190
5 Bedroom, 3 Bath Home for Rent
Available Dec 26
Furnished

3 Chapel Way

StonehamMA02180
property at 34 George St
$6,750

Total Monthly Price

Base Rent$6,750

Total Monthly Price$6,750
5 Bedroom, 2 Bath Home for Rent
Available Jun 1, 2027

34 George St

MedfordMA02155
property at 314 Massachusetts Ave
$4,750

Total Monthly Price

Base Rent$4,750

Total Monthly Price$4,750
5 Bedroom, 2 Bath Home for Rent
Available Now

314 Massachusetts Ave

ArlingtonMA02474
close
View Me
118 Summer St
5 Bedroom Apartments

118 Summer St

118 Summer StMedford, MA 02155

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 100 Studio Apartments in Winchester with rent ranges from $1,650 to $3,360 with an average price of $2,365.

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 $4,305 with an average monthly rent of $2,653.

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 $5,575. Today's average rental price for Two Bedrooms here is $3,291.

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 $6,854 - averaging $3,809 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.