Homes for Rent in Winchester, MA with Swimming Pool (16 Rentals)

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property at 200 Swanton St

$2,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

1 Bedroom, 1 Bath Condo for Rent

Available Now

200 Swanton St, Unit 228

200 Swanton St
WinchesterMA01890
property at 200 Swanton St

$2,100

Total Monthly Price

Total Monthly Price

Base Rent
$2,100

Total Monthly Price
$2,100

1 Bedroom, 1 Bath Condo for Rent

Available Now

200 Swanton St, Unit 412

200 Swanton St
WinchesterMA01890
property at 2500 Mystic Valley Pky

$3,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 2 Bath Condo for Rent

Available Now

2500 Mystic Valley Pky, Unit 702

2500 Mystic Valley Pky
MedfordMA02155
property at 4 Arizona Ter

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Condo for Rent

Available Now

4 Arizona Ter, Unit 5

4 Arizona Ter
ArlingtonMA02474

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

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property at 3 Colonial Village Dr

$2,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

2 Bedroom, 1 Bath Condo for Rent

Available Sep 1

3 Colonial Village Dr, Unit 10

3 Colonial Village Dr
ArlingtonMA02474
property at 15 Campbell Rd

$7,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 3.5 Bath Home for Rent

Available Oct 1

15 Campbell Rd

ArlingtonMA02476
property at 2500 Mystic Valley Pky

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1

2500 Mystic Valley Pky, Unit 805

2500 Mystic Valley Pky
MedfordMA02155
property at 15 Campbell Rd

$7,000

Total Monthly Price

Total Monthly Price

Base Rent
$7,000

Total Monthly Price
$7,000

4 Bedroom, 3.5 Bath Home for Rent

Available Oct 1

15 Campbell Rd

ArlingtonMA02476
property at 146 Marble St

$2,700

Total Monthly Price

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 2 Bath Condo for Rent

Available Sep 1

146 Marble St

StonehamMA02180

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 132 Emerson Gardens Rd

$3,150

Total Monthly Price

Total Monthly Price

Base Rent
$3,150

Total Monthly Price
$3,150

2 Bedroom, 1 Bath Condo for Rent

Available Now

132 Emerson Gardens Rd

LexingtonMA02420
property at 23 Peacock Farm Rd

$4,800

Total Monthly Price

Total Monthly Price

Base Rent
$4,800

Total Monthly Price
$4,800

3 Bedroom, 2 Bath Home for Rent

Available Now

23 Peacock Farm Rd

LexingtonMA02421
property at 29 Hayes Ln

$20,000

Total Monthly Price

Total Monthly Price

Base Rent
$20,000

Total Monthly Price
$20,000

5 Bedroom, 6.5 Bath Home for Rent

Available Aug 15

29 Hayes Ln

LexingtonMA02420
property at 11 Garrison Rd

$6,995

Total Monthly Price

Total Monthly Price

Base Rent
$6,995

Total Monthly Price
$6,995

5 Bedroom, 4 Bath Home for Rent

Available Now

11 Garrison Rd

ArlingtonMA02474
property at 84 Franklin St

$1,900

Total Monthly Price

Total Monthly Price

Base Rent
$1,900

Total Monthly Price
$1,900

1 Bedroom, 1 Bath Condo for Rent

Available Now

84 Franklin St, Unit 2

84 Franklin St
StonehamMA02180

What It Really Costs to Live in Boston: A Local Renter’s Guide

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property at 27 Hermon St

$4,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

3 Bedroom, 2 Bath Home for Rent

Available Now

27 Hermon St

BelmontMA02478

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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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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Frequently Asked Questions about Winchester

What type of rentals are currently available in Winchester?

There are currently 407 Apartments for Rent in Winchester, MA with pricing that ranges from $1,000 to $20,951. There are also 278 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $985 to $20,000.

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 $985 to $20,000 with an average monthly rent of $4,687.

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 $2,600 to $6,000, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,900 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,850 and Four Bedroom Apartments start at $3,300.

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!

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

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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.

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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.

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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.

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

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.