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Cheap Apartments for Rent in Winchester, MA

272 Rentals
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  1. Building Photo - 18 Reed St
    2 BEDS, 1 BATH
    $2,900
    Total Monthly Price Total Monthly Price New
    Base Rent$2,900
    Required Monthly FeesNone
    Total Monthly Price$2,900

    18 Reed St Unit 1

    18 Reed St, Arlington, MA 02474
  2. Building Photo - 286 Main St
    2 BEDS, 2 BATHS
    $2,995
    Total Monthly Price Total Monthly Price New
    Base Rent$2,995
    Required Monthly FeesNone
    Total Monthly Price$2,995
         - 12 Month Lease

    286 Main St Unit 3

    286 Main St, Woburn, MA 01801
  3. Building Photo - 36 Cross St
    2 BEDS, 1 BATH
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    36 Cross St Unit 1

    36 Cross St, Winchester, MA 01890
  4. Building Photo - 200 Swanton St
    2 BEDS, 1 BATH
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    200 Swanton St Unit T35

    200 Swanton St, Winchester, MA 01890
  5. 3 BEDS, 1 BATH
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    97 Bow St Unit 2

    97 Bow St, Arlington, MA 02474
  6. 2 BEDS, 1 BATH
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    47 Lincoln St Unit 1

    47 Lincoln St, Stoneham, MA 02180
  7. 2 BEDS, 2.5 BATHS
    $3,300
    Total Monthly Price Total Monthly Price New
    Base Rent$3,300
    Required Monthly FeesNone
    Total Monthly Price$3,300

    7 Conant Rd

    7 Conant Rd, Winchester, MA 01890
  8. Frontyard and Main Entry - 2 George Rd
    3 BEDS, 2 BATHS
    $3,400
    Total Monthly Price Total Monthly Price New
    Base Rent$3,400
    Required Monthly FeesNone
    Total Monthly Price$3,400
         - 12 Month Lease

    2 George Rd

    2 George Rd, Winchester, MA 01890
    Apply
  9. Building Photo - 38 Norwich Cir
    3 BEDS, 1.5 BATHS
    $3,650
    Total Monthly Price Total Monthly Price New
    Base Rent$3,650
    Required Monthly FeesNone
    Total Monthly Price$3,650

    38 Norwich Cir

    38 Norwich Cir, Medford, MA 02155
  10. Building Photo - 66-68 Summit St
    3 BEDS, 2 BATHS
    $3,650
    Total Monthly Price Total Monthly Price New
    Base Rent$3,650
    Required Monthly FeesNone
    Total Monthly Price$3,650

    66-68 Summit St

    66-68 Summit St, Arlington, MA 02474
  11. Building Photo - 67 Dunster Ln
    2 BEDS, 1 BATH
    $3,700
    Total Monthly Price Total Monthly Price New
    Base Rent$3,700
    Required Monthly FeesNone
    Total Monthly Price$3,700
         - 12 Month Lease

    67 Dunster Ln

    67 Dunster Ln, Winchester, MA 01890
    Apply
  12. Building Photo - 2 Stratton Dr
    2 BEDS, 2 BATHS
    $3,750
    Total Monthly Price Total Monthly Price New
    Base Rent$3,750
    Required Monthly FeesNone
    Total Monthly Price$3,750

    2 Stratton Dr Unit 102

    2 Stratton Dr, Woburn, MA 01801
  13. Building Photo - 2012 Symmes Cir
    2 BEDS, 2.5 BATHS
    $4,000
    Total Monthly Price Total Monthly Price New
    Base Rent$4,000
    Required Monthly FeesNone
    Total Monthly Price$4,000
         - 12 Month Lease

    2012 Symmes Cir Unit 1

    2012 Symmes Cir, Arlington, MA 02474
  14. Building Photo - 69 Westminster Ave
    3 BEDS, 1.5 BATHS
    $4,000
    Total Monthly Price Total Monthly Price New
    Base Rent$4,000
    Required Monthly FeesNone
    Total Monthly Price$4,000

    69 Westminster Ave

    69 Westminster Ave, Arlington, MA 02474
  15. Building Photo - 10 Webster St
    4 BEDS, 2 BATHS
    $4,150
    Total Monthly Price Total Monthly Price New
    Base Rent$4,150
    Required Monthly FeesNone
    Total Monthly Price$4,150
         - 17 Month Lease

    10 Webster St Unit 1

    10 Webster St, Winchester, MA 01890
    Apply
  16. Building Photo - 5 Sheridan Cir
    4 BEDS, 2 BATHS
    $4,200
    Total Monthly Price Total Monthly Price New
    Base Rent$4,200
    Required Monthly FeesNone
    Total Monthly Price$4,200
         - 12 Month Lease

    5 Sheridan Cir Unit 5

    5 Sheridan Cir, Winchester, MA 01890
    Apply
  17. Building Photo - 99 Garfield Ave
    4 BEDS, 1.5 BATHS
    $4,200
    Total Monthly Price Total Monthly Price New
    Base Rent$4,200
    Required Monthly FeesNone
    Total Monthly Price$4,200

    99 Garfield Ave

    99 Garfield Ave, Woburn, MA 01801
  18. Building Photo - 13 Garfield Ave
    4 BEDS, 3 BATHS
    $4,400
    Total Monthly Price Total Monthly Price New
    Base Rent$4,400
    Required Monthly FeesNone
    Total Monthly Price$4,400
         - 12 Month Lease

    13 Garfield Ave

    13 Garfield Ave, Woburn, MA 01801
    Apply
  19. Building Photo - 11 Garfield Ave
    4 BEDS, 3 BATHS
    $4,400
    Total Monthly Price Total Monthly Price New
    Base Rent$4,400
    Required Monthly FeesNone
    Total Monthly Price$4,400
         - 12 Month Lease

    11 Garfield Ave

    11 Garfield Ave, Woburn, MA 01801
  20. Building Photo - 8 Richardson St
    2 BEDS, 2 BATHS
    $4,500
    Total Monthly Price Total Monthly Price New
    Base Rent$4,500
    Required Monthly FeesNone
    Total Monthly Price$4,500

    8 Richardson St Unit 2

    8 Richardson St, Winchester, MA 01890
  21. Building Photo - 2009 Symmes Cir
    2 BEDS, 2.5 BATHS
    $5,000
    Total Monthly Price Total Monthly Price New
    Base Rent$5,000
    Required Monthly FeesNone
    Total Monthly Price$5,000

    2009 Symmes Cir

    2009 Symmes Cir, Arlington, MA 02474
  22. Building Photo - 3 Day Cir
    4 BEDS, 2 BATHS
    $6,500
    Total Monthly Price Total Monthly Price New
    Base Rent$6,500
    Required Monthly FeesNone
    Total Monthly Price$6,500
         - 12 Month Lease

    3 Day Cir

    3 Day Cir, Woburn, MA 01801
    Apply
  23. Building Photo - 3 Day Cir
    4 BEDS, 2 BATHS
    $6,500
    Total Monthly Price Total Monthly Price New
    Base Rent$6,500
    Required Monthly FeesNone
    Total Monthly Price$6,500

    3 Day Cir

    3 Day Cir, Woburn, MA 01801
  24. Building Photo - 322 Lowell St
    4 BEDS, 3.5 BATHS
    $6,800
    Total Monthly Price Total Monthly Price New
    Base Rent$6,800
    Required Monthly FeesNone
    Total Monthly Price$6,800

    322 Lowell St

    322 Lowell St, Lexington, MA 02420
  26. Building Photo - 31 Fells Rd
    3 BEDS, 2 BATHS
    $8,000
    Total Monthly Price Total Monthly Price New
    Base Rent$8,000
    Required Monthly FeesNone
    Total Monthly Price$8,000

    31 Fells Rd

    31 Fells Rd, Winchester, MA 01890
  27. Building Photo - 53 Old Mystic St
    5 BEDS, 2.5 BATHS
    $9,000
    Total Monthly Price Total Monthly Price New
    Base Rent$9,000
    Required Monthly FeesNone
    Total Monthly Price$9,000

    53 Old Mystic St

    53 Old Mystic St, Arlington, MA 02474
  28. 6 BEDS, 4.5 BATHS
    $9,500
    Total Monthly Price Total Monthly Price New
    Base Rent$9,500
    Required Monthly FeesNone
    Total Monthly Price$9,500

    23 Jefferson Rd

    23 Jefferson Rd, Winchester, MA 01890
  29. 6 BEDS, 4.5 BATHS
    $10,000
    Total Monthly Price Total Monthly Price New
    Base Rent$10,000
    Required Monthly FeesNone
    Total Monthly Price$10,000

    282 High St

    282 High St, Winchester, MA 01890
  30. 3 BEDS, 2.5 BATHS
    $16,000
    Total Monthly Price Total Monthly Price New
    Base Rent$16,000
    Required Monthly FeesNone
    Total Monthly Price$16,000

    37 Beverly Rd

    37 Beverly Rd, Arlington, MA 02474
  31. 5 BEDS, 6 BATHS
    $19,500
    Total Monthly Price Total Monthly Price New
    Base Rent$19,500
    Required Monthly FeesNone
    Total Monthly Price$19,500

    30 Whipple Rd

    30 Whipple Rd, Lexington, MA 02420
Showing 42 of 73 results, Page 2 of 2

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Winchester at a Glance

Average Rent

$2,863
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
9

School Rating

out of 10 Rating
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Schools in Winchester

Renting in Winchester

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Education

GreatSchools Rating
Winchester High School

Public High School

Public
Grades 9-12
Students
GreatSchools Rating
McCall Middle

Public Middle School

Public
Grades 6-8
Students
GreatSchools Rating
Ambrose Elementary

Public Elementary School

Public
Grades K-5
Students
GreatSchools Rating
Lincoln Elementary

Public Elementary School

Public
Grades K-5
Students
GreatSchools Rating
Muraco Elementary

Public Elementary School

Public
Grades K-5
Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

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