Luxury Homes for Rent in Winchester Highlands Neighborhood of Winchester, MA (42 Rentals)

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The most luxurious Homes in the Winchester Highlands area of Winchester with high-end amenities, features, and finishes.

property at 35 Vine St

$2,699

Total Monthly Price

Total Monthly Price

Base Rent
$2,699

Total Monthly Price
$2,699

2 Bedroom, 2 Bath Condo for Rent

Available Now

35 Vine St

WinchesterMA01890
property at 31 Irving St

$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 Sep 1

31 Irving St

WinchesterMA01890
property at 60 Lake St

$3,200

Total Monthly Price

Total Monthly Price

Base Rent
$3,200

Total Monthly Price
$3,200

2 Bedroom, 1.5 Bath Condo for Rent

Available Jul 1

60 Lake St

WinchesterMA01890
property at 7 Conant Rd

$3,400

Total Monthly Price

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2.5 Bath Condo for Rent

Available Aug 1

7 Conant Rd

WinchesterMA01890
property at 63-65 Harvard St

$3,400

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

3 Bedroom, 2 Bath Townhome for Rent

Available Jun 30

63-65 Harvard St

WinchesterMA01890
property at 16 Richardson St

$3,600

Total Monthly Price

Total Monthly Price

Base Rent
$3,600

Total Monthly Price
$3,600

3 Bedroom, 2 Bath Townhome for Rent

Available Jul 1

16 Richardson St

WinchesterMA01890
property at 63 Holland St

$3,800

Total Monthly Price

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

2 Bedroom, 1 Bath Townhome for Rent

Available Now

63 Holland St

WinchesterMA01890

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property at 33 Nelson St

$3,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,800

Total Monthly Price
$3,800

2 Bedroom, 1.5 Bath Home for Rent

Available Aug 1

33 Nelson St

WinchesterMA01890
property at 67 Church St

$4,200

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,200

Total Monthly Price
$4,200

2 Bedroom, 1 Bath Townhome for Rent

Available Aug 1

67 Church St

WinchesterMA01890
property at 41 Cross St

$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 Aug 1

41 Cross St

WinchesterMA01890
property at 488 Washington St

$4,850

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$4,850

Total Monthly Price
$4,850

4 Bedroom, 1.5 Bath Home for Rent

Available Jul 1

488 Washington St

WinchesterMA01890
property at 31 Fells Rd

$6,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$6,000

Total Monthly Price
$6,000

3 Bedroom, 2 Bath Home for Rent

Available Now

31 Fells Rd

WinchesterMA01890
property at 17 Churchill Rd

$6,850

Total Monthly Price

Total Monthly Price

Base Rent
$6,850

Total Monthly Price
$6,850

5 Bedroom, 3.5 Bath Home for Rent

Available Aug 15

17 Churchill Rd

WinchesterMA01890
property at 18 Grant Rd

$7,900

Total Monthly Price

Total Monthly Price

Base Rent
$7,900

Total Monthly Price
$7,900

4 Bedroom, 2.5 Bath Home for Rent

Available Now

18 Grant Rd

WinchesterMA01890
property at 34 Glen Rd

$11,000

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$11,000

Total Monthly Price
$11,000

7 Bedroom, 3.5 Bath Home for Rent

Available Now

34 Glen Rd

WinchesterMA01890

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property at 59 Wedgemere Ave

$12,000

Total Monthly Price

Total Monthly Price

Base Rent
$12,000

Total Monthly Price
$12,000

4 Bedroom, 3.5 Bath Home for Rent

Available Aug 1

59 Wedgemere Ave

WinchesterMA01890
property at 200 Swanton St

$2,675

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,675

Total Monthly Price
$2,675

2 Bedroom, 1 Bath Condo for Rent

Available Now

200 Swanton St, Unit T37

200 Swanton St
WinchesterMA01890
property at 289 Elm St

$2,500

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 2 Bath Condo for Rent

Available Now

289 Elm St, Unit 14

289 Elm St
MedfordMA02155
property at 74 Beach St

$2,700

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,700

Total Monthly Price
$2,700

2 Bedroom, 1 Bath Condo for Rent

Available Now

74 Beach St, Unit 6-12

74 Beach St
WoburnMA01801
property at 40 Sturges St

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

3 Bedroom, 1.5 Bath Condo for Rent

Available Now

40 Sturges St, Unit 1

40 Sturges St
MedfordMA02155
property at 295 W Wyoming Ave

$2,800

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$2,800

Total Monthly Price
$2,800

2 Bedroom, 2 Bath Condo for Rent

Available Jul 1

295 W Wyoming Ave, Unit 1A

295 W Wyoming Ave
StonehamMA02180
property at 841 Fellsway W

$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

841 Fellsway W

MedfordMA02155
property at 479 Fulton St

$5,295

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,295

Total Monthly Price
$5,295

5 Bedroom, 4.5 Bath Condo for Rent

Available Now

479 Fulton St

MedfordMA02155

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property at 64 Newcomb Rd

$15,000

Total Monthly Price1 Month Lease Term

Total Monthly Price

Base Rent
$15,000

Total Monthly Price
$15,000

5 Bedroom, 4 Bath Home for Rent

Available Jun 29

64 Newcomb Rd

StonehamMA02180
property at 39 Franklin St

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

3 Bedroom, 1 Bath Townhome for Rent

Available Now

39 Franklin St

WoburnMA01801
property at 558 Main St

$2,500

Total Monthly Price

Total Monthly Price

Base Rent
$2,500

Total Monthly Price
$2,500

2 Bedroom, 1 Bath Condo for Rent

Available Aug 1

558 Main St

StonehamMA02180

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property at 220 Central 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 Aug 1

220 Central St

StonehamMA02180
property at 202 Central 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 Jul 1

202 Central St

StonehamMA02180
property at 16 Kilby St

$2,900

Total Monthly Price

Total Monthly Price

Base Rent
$2,900

Total Monthly Price
$2,900

4 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

16 Kilby St

WoburnMA01801
property at 1 Main St

$2,950

Total Monthly Price

Total Monthly Price

Base Rent
$2,950

Total Monthly Price
$2,950

2 Bedroom, 1 Bath Home for Rent

Available Now

1 Main St

WoburnMA01801
property at 20 Bryant St

$3,100

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$3,100

Total Monthly Price
$3,100

3 Bedroom, 1 Bath Townhome for Rent

Available Jul 1

20 Bryant St

WoburnMA01801
property at 282 Place Ln

$3,400

Total Monthly Price

Total Monthly Price

Base Rent
$3,400

Total Monthly Price
$3,400

2 Bedroom, 2 Bath Condo for Rent

Available Now

282 Place Ln

WoburnMA01801
property at 6 Philips 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 Aug 1

6 Philips Rd

StonehamMA02180
property at 50 Belle Ave

$5,500

Total Monthly Price

Total Monthly Price

Base Rent
$5,500

Total Monthly Price
$5,500

4 Bedroom, 3.5 Bath Condo for Rent

Available Jul 1

50 Belle Ave

MedfordMA02155

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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 186 Salem St

$5,900

Total Monthly Price12 Month Lease Term

Total Monthly Price

Base Rent
$5,900

Total Monthly Price
$5,900

4 Bedroom, 2.5 Bath Home for Rent

Available Aug 1

186 Salem St

WoburnMA01801
property at 28 Park Ave

$6,500

Total Monthly Price

Total Monthly Price

Base Rent
$6,500

Total Monthly Price
$6,500

3 Bedroom, 3.5 Bath Home for Rent

Available Sep 1

28 Park Ave

MedfordMA02155

Frequently Asked Questions about Winchester Highlands

What type of rentals are currently available in Winchester Highlands?

There are currently 113 Apartments for Rent in Winchester Highlands, MA with pricing that ranges from $950 to $11,016. There are also 54 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester Highlands ranging from $1,900 to $25,000.

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

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winchester Highlands ranges from $1,900 to $25,000 with an average monthly rent of $6,435.

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

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winchester Highlands range from $950 to $6,704, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,500 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,900 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.

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