Apartments for Rent in Winchester, MA (542 Rentals) Page 7 of 11

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property at 17 Oakledge St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1.5 Bath Home for Rent

Available Sep 1

17 Oakledge St

ArlingtonMA02474
property at 19-21-21 Orient Ave

$2,899

Total Monthly Price

Total Monthly Price

Base Rent
$2,899

Total Monthly Price
$2,899

2 Bedroom, 1 Bath Home for Rent

Available Dec 1

19-21-21 Orient Ave

ArlingtonMA02474
property at 14 Wildwood Ave

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 1 Bath Home for Rent

Available Now

14 Wildwood Ave

ArlingtonMA02476
property at 969 Massachusetts Ave

$2,775

Total Monthly Price

Total Monthly Price

Base Rent
$2,775

Total Monthly Price
$2,775

3 Bedroom, 2 Bath Home for Rent

Available Now

969 Massachusetts Ave

ArlingtonMA02476
property at 19-19 Forest St

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Home for Rent

Available Now

19-19 Forest St

MedfordMA02155
property at 146 W Adams St

$8,100

Total Monthly Price

Total Monthly Price

Base Rent
$8,100

Total Monthly Price
$8,100

6 Bedroom, 2 Bath Home for Rent

Available Jun 1, 2027

146 W Adams St

SomervilleMA02144
property at 455 Massachusetts Ave

$2,695 - $3,450

Total Monthly Price

Total Monthly Price

Base Rent
$2,695

Total Monthly Price
$2,695

Studio To 1 Bedroom Rentals

Available Now

455 Massachusetts Ave

ArlingtonMA02474
property at 41 Monument St

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Home for Rent

Available Now

41 Monument St

MedfordMA02155
property at 6 Prentiss Rd

$2,700

Total Monthly Price

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Home for Rent

Available Sep 1

6 Prentiss Rd

ArlingtonMA02476
property at 314 Massachusetts Ave

$5,000

Total Monthly Price

Total Monthly Price

Base Rent
$5,000

Total Monthly Price
$5,000

5 Bedroom, 2 Bath Home for Rent

Available Now

314 Massachusetts Ave

ArlingtonMA02474
property at 72-74 Harlow St

$4,200

Total Monthly Price

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

6 Bedroom, 2 Bath Home for Rent

Available Sep 1

72-74 Harlow St

ArlingtonMA02474
property at 75 Orchard St

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom Rentals

Available Sep 1

75 Orchard St

MedfordMA02155
property at 3 Forest St

$2,800

Total Monthly Price

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Home for Rent

Available Now

3 Forest St

MedfordMA02155
property at 17 Ashland St

$2,900

Total Monthly Price

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

2 Bedroom, 1 Bath Home for Rent

Available Now

17 Ashland St

MedfordMA02155
property at 44 Ashland St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

2 Bedroom, 1 Bath Home for Rent

Available Now

44 Ashland St

MedfordMA02155
property at 157 Winthrop St

$3,700

Total Monthly Price

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

3 Bedroom, 1 Bath Home for Rent

Available Now

157 Winthrop St

MedfordMA02155
property at 18 Mystic St

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1 Bath Home for Rent

Available Now

18 Mystic St

MedfordMA02155
property at 7 Gorham Rd

$4,000

Total Monthly Price

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 2 Bath Home for Rent

Available Sep 1

7 Gorham Rd

MedfordMA02155
property at 269 Alewife Brook Pkwy

$3,600

Total Monthly Price

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 1 Bath Home for Rent

Available Now

269 Alewife Brook Pkwy

SomervilleMA02144
property at 89 Burget Ave

$4,500

Total Monthly Price

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

4 Bedroom, 2 Bath Home for Rent

Available Sep 1

89 Burget Ave

MedfordMA02155
property at 31 Lyman Ave

$3,100 - $3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom Rentals

Available Now

31 Lyman Ave

MedfordMA02155
property at 437 High St

$3,500

Total Monthly Price

Total Monthly Price

Base Rent
$3,500

Total Monthly Price
$3,500

3 Bedroom, 1 Bath Home for Rent

Available Now

437 High St

MedfordMA02155
property at 117 Auburn St

$2,400

Total Monthly Price

Total Monthly Price

Base Rent
$2,400

Total Monthly Price
$2,400

2 Bedroom, 1 Bath Home for Rent

Available Now

117 Auburn St

MedfordMA02155
property at 30 South St

$3,300

Total Monthly Price

Total Monthly Price

Base Rent
$3,300

Total Monthly Price
$3,300

3 Bedroom, 2 Bath Home for Rent

Available Sep 1

30 South St

MedfordMA02155
property at 87 Forest St

$3,875

Total Monthly Price

Total Monthly Price

Base Rent
$3,875

Total Monthly Price
$3,875

3 Bedroom, 1 Bath Home for Rent

Available Sep 1

87 Forest St

MedfordMA02155
property at 67 Greenleaf Ave

$2,600

Total Monthly Price

Total Monthly Price

Base Rent
$2,600

Total Monthly Price
$2,600

2 Bedroom, 1 Bath Home for Rent

Available Now

67 Greenleaf Ave

MedfordMA02155
property at 44 Orchard St

$4,000

Total Monthly Price

Total Monthly Price

Base Rent
$4,000

Total Monthly Price
$4,000

4 Bedroom, 1 Bath Home for Rent

Available Now

44 Orchard St

MedfordMA02155
property at 1304 Broadway

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

3 Bedroom, 1 Bath Home for Rent

Available Sep 1

1304 Broadway

SomervilleMA02144
property at 9 Hardan Rd

$3,700

Total Monthly Price

Total Monthly Price

Base Rent
$3,700

Total Monthly Price
$3,700

2 Bedroom, 1 Bath Home for Rent

Available Now

9 Hardan Rd

SomervilleMA02144
property at 111 Hillsdale Rd

$5,995

Total Monthly Price

Total Monthly Price

Base Rent
$5,995

Total Monthly Price
$5,995

5 Bedroom, 2 Bath Home for Rent

Available Now

111 Hillsdale Rd

SomervilleMA02144
property at 28 Sunset Rd

$3,600

Total Monthly Price

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

4 Bedroom, 1 Bath Home for Rent

Available Sep 1

28 Sunset Rd

SomervilleMA02144
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3 Burlington St
Studio to 4 Bedroom Apartments

3 Burlington St

3 Burlington StWoburn, MA 01801
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119 Pleasant St
Studio to 1 Bedroom Apartments

119 Pleasant St

119 Pleasant StArlington, MA 02476
Corporate Housing
  • Smoke Free
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292 Boston Ave
2 Bedroom Apartments

292 Boston Ave

292 Boston AveMedford, MA 02155
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Hillcrest Arm
Studio Apartments

Hillcrest Arm

59 Cambridge RdWoburn, MA 01801
  • Smoke Free
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474-482 Main St
3 Bedroom Apartments

474-482 Main St

474-482 Main StWoburn, MA 01801
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24 Oak Knls
1 Bedroom Apartments

24 Oak Knls

24 Oak KnlsArlington, MA 02476
Corporate Housing
  • Smoke Free
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Capitol Square
Studio to 2 Bedroom Apartments

Capitol Square

252 Massachusetts AveArlington, MA 02474
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The Summit House
Studio to 2 Bedroom Apartments

The Summit House

215 Massachusetts AveArlington, MA 02474
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Reading Woods
Studio Apartments

Reading Woods

55 Jacob WayReading, MA 01867
Senior Living
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The Village
2 to 3 Bedroom Apartments

The Village

171 Swanton StWinchester, MA 01890
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40 Elmwood Ave
2 Bedroom Apartments

40 Elmwood Ave

40 Elmwood AveWinchester, MA 01890
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10 Winchester Plz
2 Bedroom Apartments

10 Winchester Plz

10 Winchester PlzWinchester, MA 01890

Frequently Asked Questions about Winchester

What is the current pricing and availability for apartments for rent in Winchester, MA?

As of today, August 29, 2026, there are currently 542 available Winchester apartments priced from $825 to $19,900, with an average monthly rent of $3,446.

What Winchester neighborhoods have the most available apartments?

There are 3 neighborhoods in the Winchester area with available listings as of today. The three neighborhoods with the most options are Kendall Square with 5,841 listings, West End Boston with 5,203 listings, and North Station with 4,692 listings.

How much are Studio apartments in Winchester?

There are currently 103 Studio Apartments in Winchester with rent ranges from $1,725 to $3,350 with an average price of $2,381.

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 $4,070 with an average monthly rent of $2,611.

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 $5,441. Today's average rental price for Two Bedrooms here is $3,265.

How expensive are Winchester Three Bedroom Apartments?

There are currently 95 Three Bedroom Apartments listings available in Winchester on ApartmentHomeLiving.com. The pricing ranges from $2,500 to $6,471 - averaging $3,776 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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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

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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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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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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.

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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.