Luxury Homes for Rent in Winchester, MA (230 Rentals) Page 4 of 5

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

property at 40 Highland Ave
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
3 Bedroom, 2.5 Bath Home for Rent
Available Nov 1
Luxury

40 Highland Ave

ArlingtonMA02476
property at 582 Massachusetts Ave
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
4 Bedroom, 1.5 Bath Townhome for Rent
Available Now

582 Massachusetts Ave

LexingtonMA02420
property at 72 Cambridge Rd
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
4 Bedroom, 2.5 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

72 Cambridge Rd

WoburnMA01801
property at 24 Oxford St
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

24 Oxford St, Unit 1

24 Oxford St
ArlingtonMA02474
property at 62 Woods Ave
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
3 Bedroom, 1 Bath Condo for Rent
Available Now

62 Woods Ave, Unit 2##

62 Woods Ave
SomervilleMA02144
property at 20 Fieldstone Dr
$4,500

Total Monthly Price

Base Rent$4,500

Total Monthly Price$4,500
12 Month Lease Term
4 Bedroom, 2.5 Bath Home for Rent
Available Now

20 Fieldstone Dr

StonehamMA02180
property at 61 Taft Ave
$4,600

Total Monthly Price

Base Rent$4,600

Total Monthly Price$4,600
3 Bedroom, 2 Bath Home for Rent
Available Now

61 Taft Ave

LexingtonMA02421
property at 5 Stoneham St
$4,625

Total Monthly Price

Base Rent$4,625

Total Monthly Price$4,625
12 Month Lease Term
4 Bedroom, 2.5 Bath Home for Rent
Available Sep 30
Outdoors

5 Stoneham St

WoburnMA01801
property at 421 High St
$4,750

Total Monthly Price

Base Rent$4,750

Total Monthly Price$4,750
2 Bedroom, 2.5 Bath Townhome for Rent
Available Now

421 High St

MedfordMA02155
property at 36 Whittier Rd
$4,750

Total Monthly Price

Base Rent$4,750

Total Monthly Price$4,750
12 Month Lease Term
5 Bedroom, 2.5 Bath Home for Rent
Available Now

36 Whittier Rd

MedfordMA02155
property at 14 Kings Ct
$4,800

Total Monthly Price

Base Rent$4,800

Total Monthly Price$4,800
12 Month Lease Term
4 Bedroom, 2.5 Bath Home for Rent
Available Now
Outdoors

14 Kings Ct

ArlingtonMA02474
property at 14 Kings Ct
$4,800

Total Monthly Price

Base Rent$4,800

Total Monthly Price$4,800
4 Bedroom, 2.5 Bath Home for Rent
Available Now
Luxury

14 Kings Ct

ArlingtonMA02474
property at 9 Peacock Farm Rd
$4,850

Total Monthly Price

Base Rent$4,850

Total Monthly Price$4,850
12 Month Lease Term
3 Bedroom, 2 Bath Home for Rent
Available Now

9 Peacock Farm Rd

LexingtonMA02421
property at 116 Grove St
$4,850

Total Monthly Price

Base Rent$4,850

Total Monthly Price$4,850
12 Month Lease Term
4 Bedroom, 3 Bath Home for Rent
Available Now
Luxury

116 Grove St

MedfordMA02155
property at 34 Salem St
$4,995

Total Monthly Price

Base Rent$4,995

Total Monthly Price$4,995
12 Month Lease Term
3 Bedroom, 2.5 Bath Condo for Rent
Available Now

34 Salem St, Unit 201

34 Salem St
MedfordMA02155
  • Smoke Free
property at 34 Salem St
$4,995

Total Monthly Price

Base Rent$4,995

Total Monthly Price$4,995
3 Bedroom Rentals
Available Now

34 Salem St

MedfordMA02155
  • Smoke Free
property at 8 Brown Rd
$5,250

Total Monthly Price

Base Rent$5,250

Total Monthly Price$5,250
4 Bedroom, 2 Bath Home for Rent
Available Now
Luxury

8 Brown Rd

LexingtonMA02420
property at 559 Winthrop St
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
12 Month Lease Term
5 Bedroom, 3 Bath Home for Rent
Available Now

559 Winthrop St

MedfordMA02155
property at 11 Raymond Ave
$5,500 - $5,600

Total Monthly Price

Base Rent$5,500 - $5,600

Total Monthly Price$5,500 - $5,600
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Jun 1, 2027
Cost Per Sq.Ft.

11 Raymond Ave

SomervilleMA02144
property at 33 Raymond Ave
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Jun 1, 2027

33 Raymond Ave, Unit 2

33 Raymond Ave
SomervilleMA02144
property at 8 Baker Ave
$5,500

Total Monthly Price

Base Rent$5,500

Total Monthly Price$5,500
12 Month Lease Term
4 Bedroom, 2.5 Bath Home for Rent
Available Oct 1
Outdoors

8 Baker Ave

LexingtonMA02421
property at 14 Sturtevant Ter
$5,600

Total Monthly Price

Base Rent$5,600

Total Monthly Price$5,600
12 Month Lease Term
4 Bedroom, 2 Bath Condo for Rent
Available Now
Cost Per Sq.Ft.

14 Sturtevant Ter, Unit 1

14 Sturtevant Ter
MedfordMA02155
property at 18 Winchester Dr
$5,900

Total Monthly Price

Base Rent$5,900

Total Monthly Price$5,900
4 Bedroom, 3 Bath Home for Rent
Available Now
Cost Per Sq.Ft.

18 Winchester Dr

LexingtonMA02420
property at 11 Garrison Rd
$5,950

Total Monthly Price

Base Rent$5,950

Total Monthly Price$5,950
5 Bedroom, 4 Bath Home for Rent
Available Now
Outdoors

11 Garrison Rd

ArlingtonMA02474
property at 38 Courtyard Pl
$6,000

Total Monthly Price

Base Rent$6,000

Total Monthly Price$6,000
3 Bedroom, 4.5 Bath Townhome for Rent
Available Now
Cost Per Sq.Ft.

38 Courtyard Pl

LexingtonMA02420
property at 120 Jerome St
$6,495

Total Monthly Price

Base Rent$6,495

Total Monthly Price$6,495
12 Month Lease Term
6 Bedroom, 5 Bath Condo for Rent
Available Now

120 Jerome St, Unit 1

120 Jerome St
MedfordMA02155
property at 3 Day Cir
$6,500

Total Monthly Price

Base Rent$6,500

Total Monthly Price$6,500
12 Month Lease Term
4 Bedroom, 2 Bath Home for Rent
Available Now

3 Day Cir

WoburnMA01801
property at 322 Lowell St
$6,500

Total Monthly Price

Base Rent$6,500

Total Monthly Price$6,500
4 Bedroom, 3.5 Bath Home for Rent
Available Now
Outdoors

322 Lowell St

LexingtonMA02420
property at 73 Hillsdale Rd
$6,500

Total Monthly Price

Base Rent$6,500

Total Monthly Price$6,500
12 Month Lease Term
5 Bedroom, 2 Bath Condo for Rent
Available Jun 1, 2027
Cost Per Sq.Ft.

73 Hillsdale Rd, Unit 2

73 Hillsdale Rd
MedfordMA02155

Frequently Asked Questions about Winchester

What type of rentals are currently available in Winchester?

There are currently 445 Apartments for Rent in Winchester, MA with pricing that ranges from $825 to $18,885. There are also 283 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winchester ranging from $800 to $18,000.

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 $800 to $18,000 with an average monthly rent of $4,028.

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 $2,500 to $6,718, while Three Bedroom Homes, Condos, and Townhomes for rent range from $2,800 to $6,500. Four Bedroom Single-Family rentals are also available starting from $3,450 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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