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  1. Building Photo - 200 Swanton St
    1 BED, 1 BATH
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    200 Swanton St Unit 416

    200 Swanton St, Winchester, MA 01890
  2. Building Photo - 22 Baldwin St
    3 BEDS, 2 BATHS
    $4,200
    Total Monthly Price Total Monthly Price New
    Base Rent$4,200
    Required Monthly FeesNone
    Total Monthly Price$4,200

    22 Baldwin St

    22 Baldwin St, Winchester, MA 01890
  3. 6 BEDS, 2 BATHS
    $7,500
    Total Monthly Price Total Monthly Price New
    Base Rent$7,500
    Required Monthly FeesNone
    Total Monthly Price$7,500

    161 Highland Ave

    161 Highland Ave, Winchester, MA 01890
  4. 3 BEDS, 2.5 BATHS
    $5,500
    Total Monthly Price Total Monthly Price New
    Base Rent$5,500
    Required Monthly FeesNone
    Total Monthly Price$5,500

    111 Highland Ave

    111 Highland Ave, Winchester, MA 01890
  5. 3 BEDS, 2.5 BATHS
    $6,500
    Total Monthly Price Total Monthly Price New
    Base Rent$6,500
    Required Monthly FeesNone
    Total Monthly Price$6,500

    60 Graystone Circle

    60 Graystone Circle, Winchester, MA 01890
  6. 4 BEDS, 2 BATHS
    $3,700
    Total Monthly Price Total Monthly Price New
    Base Rent$3,700
    Required Monthly FeesNone
    Total Monthly Price$3,700

    10-12-12 Webster St Unit 1

    10-12-12 Webster St, Winchester, MA 01890
  7. 5 BEDS, 2 BATHS
    $4,950
    Total Monthly Price Total Monthly Price New
    Base Rent$4,950
    Required Monthly FeesNone
    Total Monthly Price$4,950

    79 Bacon St

    79 Bacon St, Winchester, MA 01890
  8. 2 BEDS, 1.5 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    7 Ridge St

    7 Ridge St, Winchester, MA 01890
  9. 3 BEDS, 2 BATHS
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500

    28 East St

    28 East St, Winchester, MA 01890
  10. 2 BEDS, 2 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    666 Main St Unit 315-3

    666 Main St, Winchester, MA 01890
  11. 1 BED, 1 BATH
    $2,700
    Total Monthly Price Total Monthly Price New
    Base Rent$2,700
    Required Monthly FeesNone
    Total Monthly Price$2,700

    115 Washington St Unit 1B

    115 Washington St, Winchester, MA 01890
  12. 2 BEDS, 1.5 BATHS
    $2,600
    Total Monthly Price Total Monthly Price New
    Base Rent$2,600
    Required Monthly FeesNone
    Total Monthly Price$2,600

    16 Lochwan St

    16 Lochwan St, Winchester, MA 01890
  13. 3 BEDS, 1 BATH
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500

    303 Washington St Unit 1

    303 Washington St, Winchester, MA 01890
  14. 3 BEDS, 1.5 BATHS
    $4,400
    Total Monthly Price Total Monthly Price New
    Base Rent$4,400
    Required Monthly FeesNone
    Total Monthly Price$4,400

    79 Church St Unit 1

    79 Church St, Winchester, MA 01890
  15. 2 BEDS, 1 BATH
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800

    200 Swanton St Unit 705

    200 Swanton St, Winchester, MA 01890
  16. 3 BEDS, 1.5 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    5 Quigley Ct

    5 Quigley Ct, Winchester, MA 01890
  17. 5 BEDS, 3 BATHS
    $11,500
    Total Monthly Price Total Monthly Price New
    Base Rent$11,500
    Required Monthly FeesNone
    Total Monthly Price$11,500

    10 Bellevue Ave

    10 Bellevue Ave, Winchester, MA 01890
  18. 2 BEDS, 1 BATH
    $2,400
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400
    Required Monthly FeesNone
    Total Monthly Price$2,400

    1357 Massachusetts Ave Unit 1

    1357 Massachusetts Ave, Arlington, MA 02476
  19. 4 BEDS, 2.5 BATHS
    $4,800
    Total Monthly Price Total Monthly Price New
    Base Rent$4,800
    Required Monthly FeesNone
    Total Monthly Price$4,800

    14 Kings Ct

    14 Kings Ct, Arlington, MA 02474
  20. 3 BEDS, 2 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    49 Prospect St Unit 2

    49 Prospect St, Woburn, MA 01801
  21. 4 BEDS, 1.5 BATHS
    $3,800
    Total Monthly Price Total Monthly Price New
    Base Rent$3,800
    Required Monthly FeesNone
    Total Monthly Price$3,800

    321 Washington St

    321 Washington St, Arlington, MA 02474
  22. 3 BEDS, 2 BATHS
    $4,000
    Total Monthly Price Total Monthly Price New
    Base Rent$4,000
    Required Monthly FeesNone
    Total Monthly Price$4,000

    53 Dickson Ave

    53 Dickson Ave, Arlington, MA 02474
  23. 3 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

    42 Rockland Ave

    42 Rockland Ave, Arlington, MA 02474
  24. 4 BEDS, 3.5 BATHS
    $6,600
    Total Monthly Price Total Monthly Price New
    Base Rent$6,600
    Required Monthly FeesNone
    Total Monthly Price$6,600

    322 Lowell St

    322 Lowell St, Lexington, MA 02420
  25. 5 BEDS, 3 BATHS
    $5,500
    Total Monthly Price Total Monthly Price New
    Base Rent$5,500
    Required Monthly FeesNone
    Total Monthly Price$5,500

    559 Winthrop St

    559 Winthrop St, Medford, MA 02155
  26. 4 BEDS, 3 BATHS
    $5,900
    Total Monthly Price Total Monthly Price New
    Base Rent$5,900
    Required Monthly FeesNone
    Total Monthly Price$5,900

    18 Winchester Dr

    18 Winchester Dr, Lexington, MA 02420
  27. 4 BEDS, 2 BATHS
    $3,950
    Total Monthly Price Total Monthly Price New
    Base Rent$3,950
    Required Monthly FeesNone
    Total Monthly Price$3,950

    15 Governor Rd

    15 Governor Rd, Arlington, MA 02474
  28. 3 BEDS, 1.5 BATHS
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500

    17 Oakledge St Unit 2

    17 Oakledge St, Arlington, MA 02474
  29. 3 BEDS, 2.5 BATHS
    $4,200
    Total Monthly Price Total Monthly Price New
    Base Rent$4,200
    Required Monthly FeesNone
    Total Monthly Price$4,200

    801 Manor Ter

    801 Manor Ter, Lexington, MA 02420
  30. 3 BEDS, 1 BATH
    $2,750
    Total Monthly Price Total Monthly Price New
    Base Rent$2,750
    Required Monthly FeesNone
    Total Monthly Price$2,750

    129 Madison Ave Unit 1

    129 Madison Ave, Arlington, MA 02474
  31. 2 BEDS, 1 BATH
    $2,300
    Total Monthly Price Total Monthly Price New
    Base Rent$2,300
    Required Monthly FeesNone
    Total Monthly Price$2,300

    20-22 Emerson St

    20-22 Emerson St, Stoneham, MA 02180
  32. 1 BED, 1 BATH
    $2,250
    Total Monthly Price Total Monthly Price New
    Base Rent$2,250
    Required Monthly FeesNone
    Total Monthly Price$2,250

    7 Colonial Village Dr Unit 2

    7 Colonial Village Dr, Arlington, MA 02474
  33. 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

    1 Lincoln St Unit 1

    1 Lincoln St, Stoneham, MA 02180
  34. 2 BEDS, 1 BATH
    $2,575
    Total Monthly Price Total Monthly Price New
    Base Rent$2,575
    Required Monthly FeesNone
    Total Monthly Price$2,575

    32 Century St Unit 1

    32 Century St, Medford, MA 02155
  35. 3 BEDS, 1 BATH
    $3,300
    Total Monthly Price Total Monthly Price New
    Base Rent$3,300
    Required Monthly FeesNone
    Total Monthly Price$3,300

    2 Peabody Rd Unit 2

    2 Peabody Rd, Stoneham, MA 02180
  36. 3 BEDS, 1 BATH
    $3,950
    Total Monthly Price Total Monthly Price New
    Base Rent$3,950
    Required Monthly FeesNone
    Total Monthly Price$3,950

    154 Maple St

    154 Maple St, Lexington, MA 02420
  37. 2 BEDS, 1 BATH
    $2,950
    Total Monthly Price Total Monthly Price New
    Base Rent$2,950
    Required Monthly FeesNone
    Total Monthly Price$2,950

    18 Wheelwright Rd Unit 18

    18 Wheelwright Rd, Medford, MA 02155
  38. 2 BEDS, 2 BATHS
    $3,000
    Total Monthly Price Total Monthly Price New
    Base Rent$3,000
    Required Monthly FeesNone
    Total Monthly Price$3,000

    100 Ledgewood Dr Unit 410

    100 Ledgewood Dr, Stoneham, MA 02180
  39. 2 BEDS, 1 BATH
    $2,800
    Total Monthly Price Total Monthly Price New
    Base Rent$2,800
    Required Monthly FeesNone
    Total Monthly Price$2,800

    1 Colonial Village Dr Unit 12

    1 Colonial Village Dr, Arlington, MA 02474
  40. 4 BEDS, 2 BATHS
    $3,800
    Total Monthly Price Total Monthly Price New
    Base Rent$3,800
    Required Monthly FeesNone
    Total Monthly Price$3,800

    7 Gorham Rd Unit 2

    7 Gorham Rd, Medford, MA 02155
  41. Building Photo - 19-21 Orient Ave
    2 BEDS, 1 BATH
    $2,899
    Total Monthly Price Total Monthly Price New
    Base Rent$2,899
    Required Monthly FeesNone
    Total Monthly Price$2,899

    19-21 Orient Ave Unit 21

    19-21-21 Orient Ave, Arlington, MA 02474
  42. Building Photo - 318 Mystic St
    3 BEDS, 2 BATHS
    $4,000
    Total Monthly Price Total Monthly Price New
    Base Rent$4,000
    Required Monthly FeesNone
    Total Monthly Price$4,000

    318 Mystic St

    318 Mystic St, Arlington, MA 02474
Showing 42 of 86 results, Page 2 of 3

Winchester at a Glance

Average Rent

$2,935
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
9

School Rating

out of 10 Rating
Learn more about
Schools in Winchester

Renting in Winchester

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winchester

(For 1 bedroom apartments)

Average Rent in Nearby Cities

(For 1 bedroom apartments)

Education

GreatSchools Rating
Winchester High School

Public High School

Public
Grades 9-12
1,418 Students
GreatSchools Rating
McCall Middle School

Public Middle School

Public
Grades 6-8
1,053 Students
GreatSchools Rating
Ambrose Elementary School

Public Elementary School

Public
Grades K-5
377 Students
GreatSchools Rating
Lincoln Elementary School

Public Elementary School

Public
Grades K-5
338 Students
GreatSchools Rating
Muraco Elementary School

Public Elementary School

Public
Grades K-5
296 Students

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

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