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Cheap Apartments for Rent in Winchester, MA

259 Rentals
.
  1. Building Photo - 12 Anna Rd
    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

    12 Anna Rd

    12 Anna Rd, Woburn, MA 01801
  2. Building Photo - 17 Oakledge St
    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
  3. Building Photo - 10 Webster St
    4 BEDS, 2 BATHS
    $3,900
    Total Monthly Price Total Monthly Price New
    Base Rent$3,900
    Required Monthly FeesNone
    Total Monthly Price$3,900
         - 12 Month Lease

    10 Webster St Unit 1

    10 Webster St, Winchester, MA 01890
    Apply
  4. Building Photo - 10-12-12 Webster St
    4 BEDS, 2 BATHS
    $3,900
    Total Monthly Price Total Monthly Price New
    Base Rent$3,900
    Required Monthly FeesNone
    Total Monthly Price$3,900

    10-12-12 Webster St Unit 1

    10-12-12 Webster St, Winchester, MA 01890
  5. Building Photo - 55 Stone Rd
    3 BEDS, 2 BATHS
    $3,950
    Total Monthly Price Total Monthly Price New
    Base Rent$3,950
    Required Monthly FeesNone
    Total Monthly Price$3,950

    55 Stone Rd

    55 Stone Rd, Arlington, MA 02474
  6. 4 BEDS, 1.5 BATHS
    $3,975
    Total Monthly Price Total Monthly Price New
    Base Rent$3,975
    Required Monthly FeesNone
    Total Monthly Price$3,975

    99 Garfield Ave

    99 Garfield Ave, Woburn, MA 01801
  7. 4 BEDS, 2 BATHS
    $4,100
    Total Monthly Price Total Monthly Price New
    Base Rent$4,100
    Required Monthly FeesNone
    Total Monthly Price$4,100

    7 Gorham Rd Unit 2L

    7 Gorham Rd, Medford, MA 02155
  8. 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
  9. 3 BEDS, 1.5 BATHS
    $4,300
    Total Monthly Price Total Monthly Price New
    Base Rent$4,300
    Required Monthly FeesNone
    Total Monthly Price$4,300

    26 Pearl St

    26 Pearl St, Lexington, MA 02420
  10. 3 BEDS, 2 BATHS
    $4,400
    Total Monthly Price Total Monthly Price New
    Base Rent$4,400
    Required Monthly FeesNone
    Total Monthly Price$4,400

    53 Dickson Ave

    53 Dickson Ave, Arlington, MA 02474
  11. 3 BEDS, 2.5 BATHS
    $4,400
    Total Monthly Price Total Monthly Price New
    Base Rent$4,400
    Required Monthly FeesNone
    Total Monthly Price$4,400

    801 Manor Ter

    801 Manor Ter, Lexington, MA 02420
  13. Building Photo - 488 Washington St
    4 BEDS, 1.5 BATHS
    $4,650
    Total Monthly Price Total Monthly Price New
    Base Rent$4,650
    Required Monthly FeesNone
    Total Monthly Price$4,650

    488 Washington St

    488 Washington St, Winchester, MA 01890
  14. Building Photo - 22 Baldwin St
    3 BEDS, 2 BATHS
    $4,700
    Total Monthly Price Total Monthly Price New
    Base Rent$4,700
    Required Monthly FeesNone
    Total Monthly Price$4,700

    22 Baldwin St

    22 Baldwin St, Winchester, MA 01890
  15. Building Photo - 14 Kings Ct
    4 BEDS, 2.5 BATHS
    $4,950
    Total Monthly Price Total Monthly Price New
    Base Rent$4,950
    Required Monthly FeesNone
    Total Monthly Price$4,950
         - 12 Month Lease

    14 Kings Ct

    14 Kings Ct, Arlington, MA 02474
    Apply
  16. Building Photo - 14 Kings Ct
    4 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

    14 Kings Ct

    14 Kings Ct, Arlington, MA 02474
  17. Building Photo - 129 Washington St
    3 BEDS, 3.5 BATHS
    $5,000
    Total Monthly Price Total Monthly Price New
    Base Rent$5,000
    Required Monthly FeesNone
    Total Monthly Price$5,000

    129 Washington St

    129 Washington St, Winchester, MA 01890
  18. 4 BEDS, 2 BATHS
    $5,000
    Total Monthly Price Total Monthly Price New
    Base Rent$5,000
    Required Monthly FeesNone
    Total Monthly Price$5,000

    15 Governor Rd

    15 Governor Rd, Arlington, MA 02474
  19. 4 BEDS, 3 BATHS
    $5,500
    Total Monthly Price Total Monthly Price New
    Base Rent$5,500
    Required Monthly FeesNone
    Total Monthly Price$5,500

    61 Warren St

    61 Warren St, Medford, MA 02155
  20. 5 BEDS, 3.5 BATHS
    $5,750
    Total Monthly Price Total Monthly Price New
    Base Rent$5,750
    Required Monthly FeesNone
    Total Monthly Price$5,750

    17 Churchill Rd

    17 Churchill Rd, Winchester, MA 01890
  21. Building Photo - 270 Cross St
    4 BEDS, 4 BATHS
    $6,000
    Total Monthly Price Total Monthly Price New
    Base Rent$6,000
    Required Monthly FeesNone
    Total Monthly Price$6,000
         - 12 Month Lease

    270 Cross St

    270 Cross St, Winchester, MA 01890
  22. Building Photo - 31 Fells Rd
    3 BEDS, 2 BATHS
    $6,000
    Total Monthly Price Total Monthly Price New
    Base Rent$6,000
    Required Monthly FeesNone
    Total Monthly Price$6,000

    31 Fells Rd

    31 Fells Rd, Winchester, MA 01890
  23. Building Photo - 6 Lily Pond Ln
    3 BEDS, 2.5 BATHS
    $6,000
    Total Monthly Price Total Monthly Price New
    Base Rent$6,000
    Required Monthly FeesNone
    Total Monthly Price$6,000

    6 Lily Pond Ln

    6 Lily Pond Ln, Lexington, MA 02420
  24. 4 BEDS, 4.5 BATHS
    $6,250
    Total Monthly Price Total Monthly Price New
    Base Rent$6,250
    Required Monthly FeesNone
    Total Monthly Price$6,250

    455 Summer St

    455 Summer St, Arlington, MA 02474
  25. 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
  26. Building Photo - 46 Loring Ave
    4 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

    46 Loring Ave

    46 Loring Ave, Winchester, MA 01890
  27. Building Photo - 18 Winchester Dr
    4 BEDS, 3 BATHS
    $6,500
    Total Monthly Price Total Monthly Price New
    Base Rent$6,500
    Required Monthly FeesNone
    Total Monthly Price$6,500

    18 Winchester Dr

    18 Winchester Dr, Lexington, MA 02420
  28. 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
  29. 5 BEDS, 3 BATHS
    $6,800
    Total Monthly Price Total Monthly Price New
    Base Rent$6,800
    Required Monthly FeesNone
    Total Monthly Price$6,800

    559 Winthrop St

    559 Winthrop St, Medford, MA 02155
  30. 4 BEDS, 2.5 BATHS
    $6,995
    Total Monthly Price Total Monthly Price New
    Base Rent$6,995
    Required Monthly FeesNone
    Total Monthly Price$6,995

    18 Grant Rd

    18 Grant Rd, Winchester, MA 01890
  31. Building Photo - 161 Highland Ave
    6 BEDS, 2.5 BATHS
    $8,500
    Total Monthly Price Total Monthly Price New
    Base Rent$8,500
    Required Monthly FeesNone
    Total Monthly Price$8,500
         - 12 Month Lease

    161 Highland Ave

    161 Highland Ave, Winchester, MA 01890
    Apply
  32. 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
  33. Building Photo - 59 Wedgemere Ave
    4 BEDS, 3.5 BATHS
    $12,000
    Total Monthly Price Total Monthly Price New
    Base Rent$12,000
    Required Monthly FeesNone
    Total Monthly Price$12,000

    59 Wedgemere Ave

    59 Wedgemere Ave, Winchester, MA 01890
  34. 6 BEDS, 7 BATHS
    $15,000
    Total Monthly Price Total Monthly Price New
    Base Rent$15,000
    Required Monthly FeesNone
    Total Monthly Price$15,000

    20 Amberwood Dr

    20 Amberwood Dr, Winchester, MA 01890
  35. 5 BEDS, 4.5 BATHS
    $15,000
    Total Monthly Price Total Monthly Price New
    Base Rent$15,000
    Required Monthly FeesNone
    Total Monthly Price$15,000

    186 Ridge St

    186 Ridge St, Winchester, MA 01890
Showing 42 of 77 results, Page 2 of 2

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Winchester at a Glance

Average Rent

$3,033
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
8

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
1,418 Students
GreatSchools Rating
McCall Middle School

Public Middle School

Public
Grades 6-8
1,053 Students
GreatSchools Rating
McCall Middle

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
Ambrose Elementary

Public Elementary School

Public
Grades K-5
377 Students
GreatSchools Rating
Lincoln Elementary

Public Elementary School

Public
Grades K-5
338 Students

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

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