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Cheap Apartments for Rent in Winchester, MA

248 Rentals
.
  1. Building Photo - 3 Melo Rd
    3 BEDS, 1 BATH
    $3,650
    Total Monthly Price Total Monthly Price New
    Base Rent$3,650
    Required Monthly FeesNone
    Total Monthly Price$3,650

    3 Melo Rd

    3 Melo Rd, Woburn, MA 01801
  3. 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
  4. Building Photo - 224 Park St
    3 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

    224 Park St

    224 Park St, Stoneham, MA 02180
  5. Building Photo - 5 Sheridan Cir
    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
         - 12 Month Lease

    5 Sheridan Cir Unit 5

    5 Sheridan Cir, Winchester, MA 01890
    Apply
  6. Building Photo - 63 Holland St
    2 BEDS, 1 BATH
    $4,100
    Total Monthly Price Total Monthly Price New
    Base Rent$4,100
    Required Monthly FeesNone
    Total Monthly Price$4,100

    63 Holland St

    63 Holland St, Winchester, MA 01890
  7. Building Photo - 10-12-12 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

    10-12-12 Webster St Unit 1

    10-12-12 Webster St, Winchester, MA 01890
  8. 2 BEDS, 1 BATH
    $4,400
    Total Monthly Price Total Monthly Price New
    Base Rent$4,400
    Required Monthly FeesNone
    Total Monthly Price$4,400

    67 Church St

    67 Church St, Winchester, MA 01890
  9. 3 BEDS, 3 BATHS
    $4,450
    Total Monthly Price Total Monthly Price New
    Base Rent$4,450
    Required Monthly FeesNone
    Total Monthly Price$4,450

    11 Highland View Ave

    11 Highland View Ave, Winchester, MA 01890
  10. 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
  11. Building Photo - 12 Headland Way
    3 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
         - 12 Month Lease

    12 Headland Way

    12 Headland Way, Medford, MA 02155
    Apply
  12. Building Photo - 488 Washington St
    4 BEDS, 1.5 BATHS
    $4,850
    Total Monthly Price Total Monthly Price New
    Base Rent$4,850
    Required Monthly FeesNone
    Total Monthly Price$4,850

    488 Washington St

    488 Washington St, Winchester, MA 01890
  13. Building Photo - 12 Knowles Farm Rd
    4 BEDS, 2.5 BATHS
    $5,250
    Total Monthly Price Total Monthly Price New
    Base Rent$5,250
    Required Monthly FeesNone
    Total Monthly Price$5,250
         - 12 Month Lease

    12 Knowles Farm Rd

    12 Knowles Farm Rd, Arlington, MA 02474
  14. Building Photo - 17 Cardinal St
    3 BEDS, 3.5 BATHS
    $5,500
    Total Monthly Price Total Monthly Price New
    Base Rent$5,500
    Required Monthly FeesNone
    Total Monthly Price$5,500

    17 Cardinal St

    17 Cardinal St, Winchester, MA 01890
  15. Building Photo - 15 Winchester Dr
    4 BEDS, 2 BATHS
    $5,800
    Total Monthly Price Total Monthly Price New
    Base Rent$5,800
    Required Monthly FeesNone
    Total Monthly Price$5,800

    15 Winchester Dr

    15 Winchester Dr, Lexington, MA 02420
  16. 3 BEDS, 3 BATHS
    $6,200
    Total Monthly Price Total Monthly Price New
    Base Rent$6,200
    Required Monthly FeesNone
    Total Monthly Price$6,200

    334 Mystic St

    334 Mystic St, Arlington, MA 02474
  17. 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
  18. 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
  19. 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
  20. 3 BEDS, 2.5 BATHS
    $7,400
    Total Monthly Price Total Monthly Price New
    Base Rent$7,400
    Required Monthly FeesNone
    Total Monthly Price$7,400

    6 Risley Rd

    6 Risley Rd, Winchester, MA 01890
  21. 4 BEDS, 2.5 BATHS
    $7,900
    Total Monthly Price Total Monthly Price New
    Base Rent$7,900
    Required Monthly FeesNone
    Total Monthly Price$7,900

    18 Grant Rd

    18 Grant Rd, Winchester, MA 01890
  22. 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
  23. 3 BEDS, 2.5 BATHS
    $10,000
    Total Monthly Price Total Monthly Price New
    Base Rent$10,000
    Required Monthly FeesNone
    Total Monthly Price$10,000

    37 Beverly Rd

    37 Beverly Rd, Arlington, MA 02474
  24. 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
  25. 7 BEDS, 3.5 BATHS
    $11,500
    Total Monthly Price Total Monthly Price New
    Base Rent$11,500
    Required Monthly FeesNone
    Total Monthly Price$11,500

    34 Glen Rd

    34 Glen Rd, Winchester, MA 01890
  26. 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
  27. Building Photo - 25 Falmouth Rd
    5 BEDS, 3.5 BATHS
    $13,950
    Total Monthly Price Total Monthly Price New
    Base Rent$13,950
    Required Monthly FeesNone
    Total Monthly Price$13,950
         - 12 Month Lease

    25 Falmouth Rd

    25 Falmouth Rd, Arlington, MA 02474
    Apply
  28. Building Photo - 20 Amberwood Dr
    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
  29. Building Photo - 186 Ridge St
    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 71 results, Page 2 of 2

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Winchester at a Glance

Average Rent

$2,986
(All bedrooms and property types)
Learn more about
Average Rent in Winchester
8

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)

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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