Apartments for Rent in the Winchester Highlands Neighborhood of Winchester, MA (167 Rentals) Page 2 of 4

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property at 6 Johnson St
$4,000

Total Monthly Price

Base Rent$4,000

Total Monthly Price$4,000
1 Month Lease Term
4 Bedroom, 1 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

6 Johnson St

WoburnMA01801

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property at 100 Ledgewood Dr
$3,000

Total Monthly Price

Base Rent$3,000

Total Monthly Price$3,000
2 Bedroom, 2 Bath Home for Rent
Available Now

100 Ledgewood Dr

StonehamMA02180
property at 143 Washington St
$2,750

Total Monthly Price

Base Rent$2,750

Total Monthly Price$2,750
2 Bedroom, 1 Bath Home for Rent
Available Now

143 Washington St

WoburnMA01801
property at 1 Lincoln St
$2,800

Total Monthly Price

Base Rent$2,800

Total Monthly Price$2,800
2 Bedroom, 1 Bath Home for Rent
Available Now

1 Lincoln St

StonehamMA02180
property at 49 Prospect St
$3,200

Total Monthly Price

Base Rent$3,200

Total Monthly Price$3,200
3 Bedroom, 2 Bath Home for Rent
Available Now

49 Prospect St

WoburnMA01801
property at 2 Peabody Rd
$3,000

Total Monthly Price

Base Rent$3,000

Total Monthly Price$3,000
2 Bedroom, 1 Bath Home for Rent
Available Now

2 Peabody Rd

StonehamMA02180
property at 65 Winn St
$2,795

Total Monthly Price

Base Rent$2,795

Total Monthly Price$2,795
2 Bedroom, 2 Bath Home for Rent
Available Oct 7
Cost Per Sq.Ft.

65 Winn St

WoburnMA01801
property at 7 Hawthorne St
$3,200

Total Monthly Price

Base Rent$3,200

Total Monthly Price$3,200
3 Bedroom, 2 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

7 Hawthorne St

EverettMA02149
property at 61 Wright St
$2,800

Total Monthly Price

Base Rent$2,800

Total Monthly Price$2,800
2 Bedroom, 2 Bath Condo for Rent
Available Now

61 Wright St

StonehamMA02180
property at 137 Franklin St
$2,550

Total Monthly Price

Base Rent$2,550

Total Monthly Price$2,550
2 Bedroom, 2 Bath Condo for Rent
Available Now

137 Franklin St

StonehamMA02180
property at 39 Montvale Ave
$2,200

Total Monthly Price

Base Rent$2,200

Total Monthly Price$2,200
2 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

39 Montvale Ave

WoburnMA01801
property at 33 Montvale Ave
$2,100

Total Monthly Price

Base Rent$2,100

Total Monthly Price$2,100
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

33 Montvale Ave

WoburnMA01801
property at 177 Franklin St
$2,600

Total Monthly Price

Base Rent$2,600

Total Monthly Price$2,600
2 Bedroom, 1 Bath Condo for Rent
Available Now

177 Franklin St

StonehamMA02180
property at 305 Salem St
$2,250

Total Monthly Price

Base Rent$2,250

Total Monthly Price$2,250
1 Bedroom, 1 Bath Condo for Rent
Available Oct 1
Affordability

305 Salem St

WoburnMA01801
property at 74 Beach St
$1,850

Total Monthly Price

Base Rent$1,850

Total Monthly Price$1,850
1 Bedroom Rentals
Available Now
Affordability

74 Beach St

WoburnMA01801
property at 13 Center St
$1,000

Total Monthly Price

Base Rent$1,000

Total Monthly Price$1,000
2 Bedroom, 1 Bath Home for Rent
Available Now
Affordability

13 Center St

WoburnMA01801
property at 58 Washington St
$3,500

Total Monthly Price

Base Rent$3,500

Total Monthly Price$3,500
4 Bedroom, 2 Bath Home for Rent
Available Now

58 Washington St

StonehamMA02180
property at 159 Main St
$2,750

Total Monthly Price

Base Rent$2,750

Total Monthly Price$2,750
2 Bedroom, 2 Bath Condo for Rent
Available Oct 10

159 Main St

StonehamMA02180
property at 555 Main St
$3,500

Total Monthly Price

Base Rent$3,500

Total Monthly Price$3,500
2 Bedroom, 2.5 Bath Townhome for Rent
Available Now

555 Main St

WoburnMA01801
property at 50 Belle Ave
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
4 Bedroom, 3.5 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

50 Belle Ave

MedfordMA02155
property at 100 Place Ln
$3,900

Total Monthly Price

Base Rent$3,900

Total Monthly Price$3,900
3 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

100 Place Ln

WoburnMA01801
property at 487 Place Ln
$3,550

Total Monthly Price

Base Rent$3,550

Total Monthly Price$3,550
2 Bedroom, 2 Bath Condo for Rent
Available Now
Luxury

487 Place Ln

WoburnMA01801
property at 84 Franklin St
$1,900

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
property at 74 Beach St
$1,850

Total Monthly Price

Base Rent$1,850

Total Monthly Price$1,850
1 Bedroom, 1 Bath Condo for Rent
Available Now
Affordability

74 Beach St, Unit 5-1

74 Beach St
WoburnMA01801
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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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Park Terrace
Studio Apartments

Park Terrace

291 W Wyoming AveStoneham, MA 02180
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The Village
2 to 3 Bedroom Apartments

The Village

171 Swanton StWinchester, MA 01890
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Winchester Gardens
2 to 3 Bedroom Apartments

Winchester Gardens

1-11 George RdWinchester, MA 01890
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Hillside Gardens
1 to 2 Bedroom Apartments

Hillside Gardens

101-116 Hill StStoneham, MA 02180
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The Terraces
1 to 2 Bedroom Apartments

The Terraces

12 Hillside RdStoneham, MA 02180
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588 Main St
1 to 2 Bedroom Apartments

588 Main St

588 Main StStoneham, MA 02180

Frequently Asked Questions about Winchester Highlands

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

As of today, September 21, 2026, there are currently 167 available Winchester Highlands apartments priced from $1,750 to $12,539, with an average monthly rent of $3,426.

How much are Studio apartments in Winchester Highlands?

There are currently 38 Studio Apartments in Winchester Highlands with rent ranges from $1,950 to $2,964 with an average price of $2,506.

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 $1,750 to $4,070 with an average monthly rent of $2,947.

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 $2,375 to $5,354. Today's average rental price for Two Bedrooms here is $3,559.

How expensive are Winchester Highlands Three Bedroom Apartments?

There are currently 16 Three Bedroom Apartments listings available in Winchester Highlands on ApartmentHomeLiving.com. The pricing ranges from $3,200 to $7,312 - averaging $4,890 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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