Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (174 Rentals)

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property at 2 George Rd

$3,400

Total Monthly Price

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 2 Bath Home for Rent

Available Now

2 George Rd

WinchesterMA01890
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10 Webster St, Unit 1, Unit 1
$4,150
Total Monthly Price17 Month Lease Term

Total Monthly Price

Base Rent
$4,150

Total Monthly Price
$4,150
4 Bedroom Apartment Available Now

10 Webster St, Unit 1, Unit 1

10 Webster StWinchester, MA 01890
Cost Per Sq.Ft.
  • Smoke Free
property at 200 Swanton St

$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 Sep 1

200 Swanton St, Unit 3, Unit 3

200 Swanton St
WinchesterMA01890
property at 5 Sheridan Cir

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

4 Bedroom, 2 Bath Townhome for Rent

Available Now

5 Sheridan Cir, Unit 5, Unit 5

5 Sheridan Cir
WinchesterMA01890

Boston's Best Affordable Neighborhoods

Learn about Boston and the best places to live around the area with original content written by our Boston, MA Local Expert Amelia Ramstead

property at 200 Swanton St

$2,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,000

Total Monthly Price
$2,000

1 Bedroom, 1 Bath Rentals

Available Sep 1

200 Swanton St, Unit 310

200 Swanton St
WinchesterMA01890
property at 9 Mt Vernon St

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

3 Bedroom, 2 Bath Home for Rent

Available Now

9 Mt Vernon St

WinchesterMA01890
property at 26 Lebanon St

$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

26 Lebanon St

WinchesterMA01890
property at 36 Cross St

$3,000

Total Monthly Price

Total Monthly Price

Base Rent
$3,000

Total Monthly Price
$3,000

2 Bedroom, 1 Bath Home for Rent

Available Now

36 Cross St

WinchesterMA01890
property at 31 Fells Rd

$8,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$8,000

Total Monthly Price
$8,000

3 Bedroom, 2 Bath Home for Rent

Available Now

31 Fells Rd

WinchesterMA01890
property at 200 Swanton St

$2,000 - $3,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,200

Total Monthly Price
$2,200

1 To 2 Bedroom Rentals

Available Now

200 Swanton St

WinchesterMA01890
property at 8 Richardson St

$4,500

Total Monthly Price

Total Monthly Price

Base Rent
$4,500

Total Monthly Price
$4,500

2 Bedroom, 2 Bath Condo for Rent

Available Now

8 Richardson St

WinchesterMA01890
property at 23 Jefferson Rd

$9,500

Total Monthly Price

Total Monthly Price

Base Rent
$9,500

Total Monthly Price
$9,500

6 Bedroom, 4.5 Bath Home for Rent

Available Now

23 Jefferson Rd

WinchesterMA01890
property at 34 Glen Rd

$12,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$12,000

Total Monthly Price
$12,000

7 Bedroom, 3.5 Bath Home for Rent

Available Now

34 Glen Rd

WinchesterMA01890
property at 200 Swanton St

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available Now

200 Swanton St, Unit 635, Unit 635

200 Swanton St
WinchesterMA01890

The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

property at 200 Swanton St

$2,650

Total Monthly Price

Total Monthly Price

Base Rent
$2,650

Total Monthly Price
$2,650

2 Bedroom, 1 Bath Condo for Rent

Available Now

200 Swanton St, Unit 237, Unit 237

200 Swanton St
WinchesterMA01890
property at 200 Swanton St

$1,890

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,890

Total Monthly Price
$1,890

1 Bedroom, 1 Bath Condo for Rent

Available Now

200 Swanton St, Unit 704, Unit 704

200 Swanton St
WinchesterMA01890
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Hanover Stoneham
Rent Specials
$2,431 - $4,986
Total Monthly Price

Total Monthly Price

Base Rent
$2,431 - $4,986

Total Monthly Price
Varies
Studio to 3 Bedroom Apartments Available Now

Hanover Stoneham

95 Maple StStoneham, MA 02180
Luxury
  • Verified
  • Customer Reviewed
  • Utilities Included
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The Mave
$2,715 - $5,440
Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$2,715 - $5,440

Total Monthly Price
Varies
1 to 2 Bedroom Apartments Available Now

The Mave

225 Fallon RdStoneham, MA 02180
Student Living
  • Verified
  • Customer Reviewed
  • 3D Tour
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Alta Clara
$3,002 - $5,255
Total Monthly Price

Total Monthly Price

Base Rent
$3,002 - $5,255

Total Monthly Price
Varies
1 to 2 Bedroom Apartments Available Now

Alta Clara

21 Executive DrStoneham, MA 02180
Luxury
  • Verified
  • Customer Reviewed
  • 3D Tour

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

property at 476 Fulton St

$4,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,850

Total Monthly Price
$4,850

4 Bedroom, 4.5 Bath Condo for Rent

Available Jun 1

476 Fulton St, Unit 2, Unit 2

476 Fulton St
MedfordMA02155

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.

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48 Nashua St
$1,750 - $2,400
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$1,750 - $2,400

Total Monthly Price
$1,750 - $2,400
Studio to 2 Bedroom Apartment Available Now

48 Nashua St

48 Nashua StWoburn, MA 01801
Affordability
  • Smoke Free
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479 Fulton St, Unit 1, Unit 1
$4,850
Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,850

Total Monthly Price
$4,850
4 Bedroom Apartment Available Jun 1

479 Fulton St, Unit 1, Unit 1

479 Fulton StMedford, MA 02155
Cost Per Sq.Ft.
  • Smoke Free
property at 11 Garfield Ave

$4,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,400

Total Monthly Price
$4,400

4 Bedroom, 3 Bath Townhome for Rent

Available Now

11 Garfield Ave

WoburnMA01801
property at 13 Garfield Ave

$4,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,400

Total Monthly Price
$4,400

4 Bedroom, 3 Bath Townhome for Rent

Available Now

13 Garfield Ave

WoburnMA01801
property at 39 Cottage St

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 1 Bath Condo for Rent

Available May 1

39 Cottage St, Unit 1, Unit 1

39 Cottage St
StonehamMA02180

Frequently Asked Questions about Winchester Highlands

How much are Studio apartments in Winchester Highlands?

There are currently 40 Studio Apartments in Winchester Highlands with rent ranges from $1,750 to $2,700 with an average price of $2,329.

What is the current price range for One Bedroom Winchester Highlands Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Winchester Highlands ranges from $2,050 to $4,215 with an average monthly rent of $3,014.

What does renting a Two Bedroom Apartment in Winchester Highlands cost?

The monthly rent prices of Two Bedroom Apartments currently available in Winchester Highlands range from $2,250 to $5,440. Today's average rental price for Two Bedrooms here is $3,634.

How expensive are Winchester Highlands Three Bedroom Apartments?

There are currently 18 Three Bedroom Apartments listings available in Winchester Highlands on ApartmentHomeLiving.com. The pricing ranges from $2,700 to $5,690 - averaging $4,074 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.

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