Homes for Rent by Owner near Winchester, MA (13 Rentals)

How Many Bedrooms?Done
Price OptionsDone
Price Range
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done
property at 125 Pleasant St
$2,750

Total Monthly Price

Base Rent$2,750

Total Monthly Price$2,750
10 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Now
Luxury

125 Pleasant St, Unit 306

125 Pleasant St
ArlingtonMA02476
  • Smoke Free
property at 40 Brattle St
$4,250

Total Monthly Price

Base Rent$4,250

Total Monthly Price$4,250
12 Month Lease Term
3 Bedroom, 3.5 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

40 Brattle St

ArlingtonMA02476
property at 74 Sharon St
$795

Total Monthly Price

Base Rent$795

Total Monthly Price$795
12 Month Lease Term
1 Bedroom, 2.5 Bath Townhome for Rent
Available Sep 27
Affordability

74 Sharon St

MedfordMA02155
  • Smoke Free
property at 5 Quincy St
$3,200

Total Monthly Price

Base Rent$3,200

Total Monthly Price$3,200
10 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Nov 1
Affordability

5 Quincy St, Unit 5 Quincy St

5 Quincy St
MedfordMA02155
  • Smoke Free
property at 44 Adams St
$8,200

Total Monthly Price

Base Rent$8,200

Total Monthly Price$8,200
12 Month Lease Term
6 Bedroom, 2 Bath Home for Rent
Available Jun 1, 2027

44 Adams St

MedfordMA02155
property at 2 Albert Dr
$2,400

Total Monthly Price

Base Rent$2,400

Total Monthly Price$2,400
12 Month Lease Term
2 Bedroom, 1 Bath Condo for Rent
Available Oct 1

2 Albert Dr, Unit 10

2 Albert Dr
WoburnMA01801
  • 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

property at 159 Bedford Rd
$3,800

Total Monthly Price

Base Rent$3,800

Total Monthly Price$3,800
1 Month Lease Term
3 Bedroom, 1.5 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

159 Bedford Rd

WoburnMA01801
property at 4 Senator Rd
$4,400

Total Monthly Price

Base Rent$4,400

Total Monthly Price$4,400
12 Month Lease Term
4 Bedroom, 1 Bath Townhome for Rent
Available Now
Luxury

4 Senator Rd

WoburnMA01801
property at 21 Royall St
$1,100 - $3,150

Total Monthly Price

Base Rent$1,100 - $3,150

Total Monthly Price$1,100 - $3,150
12 Month Lease Term
1 To 3 Bedroom Townhomes for Rent
Available Now
Furnished

21 Royall St

MedfordMA02155
  • Smoke Free
property at 6 Boston Ave
$1,600 - $1,800

Total Monthly Price

Base Rent$1,600 - $1,800

Total Monthly Price$1,600 - $1,800
12 Month Lease Term
1 Bedroom, 1 Bath Home for Rent
Available Now
Furnished

6 Boston Ave

MedfordMA02155
  • Smoke Free
property at 98 Sharon St
$2,000

Total Monthly Price

Base Rent$2,000

Total Monthly Price$2,000
12 Month Lease Term
1 Bedroom, 1 Bath Home for Rent
Available Now
Furnished

98 Sharon St

MedfordMA02155

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.

property at 2500 Mystic Valley Pky
$3,200

Total Monthly Price

Base Rent$3,200

Total Monthly Price$3,200
12 Month Lease Term
2 Bedroom, 2 Bath Condo for Rent
Available Now
Luxury

2500 Mystic Valley Pky, Unit 702

2500 Mystic Valley Pky
MedfordMA02155
  • Smoke Free

Winchester, MA Local Guide

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

What type of rentals are currently available in Winchester?

There are currently 440 Apartments for Rent in Winchester, MA with pricing that ranges from $825 to $12,539. There are also 280 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $795 to $18,000.

What is the current price range for Rental Homes in Winchester?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester ranges from $795 to $18,000 with an average monthly rent of $3,905.

How much are larger Three and Four Bedroom Rentals in Winchester?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester range from $2,500 to $7,312, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,000. Four Bedroom Single-Family rentals are also available starting from $3,450 and Four Bedroom Apartments start at $2,900.

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 How Commercial-to-Residential Property Conversions Help the Housing Crisis   article

How Commercial-to-Residential Property Conversions Help the Housing Crisis

Written by: Robin Stewart

Many housing markets throughout America share a common complaint: a lack of affordable rental properties.

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.