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Two Bedroom Apartments for Rent in High Street Hill

102 Rentals
  1. Building Photo - 14 Smythe 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

    14 Smythe St Unit 3

    14 Smythe St, Brookline, MA 02445
  2. Building Photo - 7 High St Pl
    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
    - 12 Month Lease

    7 High St Pl Unit 2

    7 High St Pl, Brookline, MA 02445
    (617) 477-0601
  3. Building Photo - 6 Harvard Square
    2 BEDS, 1 BATH
    $12,161
    Total Monthly Price Total Monthly Price New
    Base Rent$11,571
    Required Monthly Fees$589
    Total Monthly Price$12,160

    6 Harvard Square Unit SI FL1-ID1238033P

    6 Harvard Square, Brookline, MA 02445
  4. Building Photo - 137 Walnut St
    2 BEDS, 1 BATH
    $7,000
    Total Monthly Price Total Monthly Price New
    Base Rent$7,000
    Required Monthly FeesNone
    Total Monthly Price$7,000
    - 1 Month Lease

    137 Walnut St Unit #3

    137 Walnut St, Brookline, MA 02445
  5. Building Photo - 95 Chestnut St
    2 BEDS, 1 BATH
    $2,975
    Total Monthly Price Total Monthly Price New
    Base Rent$2,975
    Required Monthly FeesNone
    Total Monthly Price$2,975
    - 12 Month Lease

    95 Chestnut St

    95 Chestnut St, Brookline, MA 02445
  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
    - 12 Month Lease

    227 Washington St

    227 Washington St, Brookline, MA 02445
  7. 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

    91 Walnut St Unit 1

    91 Walnut St, Brookline, MA 02445
  8. 2 BEDS, 1.5 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

    50 Edgehill Rd Unit Carriage House

    50 Edgehill Rd, Brookline, MA 02445
  9. 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
    - 12 Month Lease

    234 Cypress St

    234 Cypress St, Brookline, MA 02445
  10. 2 BEDS, 1 BATH
    $3,300
    Total Monthly Price Total Monthly Price New
    Base Rent$3,300
    Required Monthly FeesNone
    Total Monthly Price$3,300
    - 12 Month Lease

    16 Davis Ave Unit #4

    16 Davis Ave, Brookline, MA 02445
  11. 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
    - 12 Month Lease

    14 Smythe St Unit 2

    14 Smythe St, Brookline, MA 02445
  12. 2 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 Month Lease

    77 Walnut St Unit 1

    77 Walnut St, Brookline, MA 02445
  13. 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
    - 12 Month Lease

    48 Cameron St Unit 3

    48 Cameron St, Brookline, MA 02445
  14. 2 BEDS, 1 BATH
    $2,850
    Total Monthly Price Total Monthly Price New
    Base Rent$2,850
    Required Monthly FeesNone
    Total Monthly Price$2,850
    - 12 Month Lease

    231 High St Unit 1

    231 High St, Brookline, MA 02445
  15. 2 BEDS, 1 BATH
    $4,300
    Total Monthly Price Total Monthly Price New
    Base Rent$4,300
    Required Monthly FeesNone
    Total Monthly Price$4,300
    - 12 Month Lease

    50 Cameron St Unit 4

    50 Cameron St, Brookline, MA 02445
  16. 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
    - 12 Month Lease

    48 Cameron St

    48 Cameron St, Brookline, MA 02445
  17. 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
    - 12 Month Lease

    14 Smythe St Unit 2

    14 Smythe St, Brookline, MA 02445
  18. 2 BEDS, 1 BATH
    $7,000
    Total Monthly Price Total Monthly Price New
    Base Rent$7,000
    Required Monthly FeesNone
    Total Monthly Price$7,000
    - 12 Month Lease

    7 Harvard Sq Unit #5C

    7 Harvard Sq, Brookline, MA 02445
  19. 2 BEDS, 1 BATH
    $3,600
    Total Monthly Price Total Monthly Price New
    Base Rent$3,600
    Required Monthly FeesNone
    Total Monthly Price$3,600
    - 12 Month Lease

    82 Walnut St

    82 Walnut St, Brookline, MA 02445
  20. 2 BEDS, 1 BATH
    $3,100
    Total Monthly Price Total Monthly Price New
    Base Rent$3,100 - $6,825
    Required Monthly FeesNone
    Total Monthly Price$3,100 - $6,825
    - 12 Month Lease

    91 Chestnut St

    91 Chestnut St, Brookline, MA 02445
  21. 2 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

    21 High St Unit 1

    21 High St, Brookline, MA 02445
  22. 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
    - 12 Month Lease

    217 Washington St Unit 1

    217 Washington St, Brookline, MA 02445
  23. 2 BEDS, 2 BATHS
    $4,300
    Total Monthly Price Total Monthly Price New
    Base Rent$4,300
    Required Monthly FeesNone
    Total Monthly Price$4,300
    - 12 Month Lease

    77 Pond Ave

    77 Pond Ave, Brookline, MA 02445
  24. 2 BEDS, 1 BATH
    $3,150
    Total Monthly Price Total Monthly Price New
    Base Rent$3,150
    Required Monthly FeesNone
    Total Monthly Price$3,150
    - 12 Month Lease

    14 Smythe St Unit 3

    14 Smythe St, Brookline, MA 02445
  25. 2 BEDS, 1 BATH
    $3,600
    Total Monthly Price Total Monthly Price New
    Base Rent$3,600
    Required Monthly FeesNone
    Total Monthly Price$3,600
    - 12 Month Lease

    110 Cypress St

    110 Cypress St, Brookline, MA 02445
  26. 2 BEDS, 1 BATH
    $3,400
    Total Monthly Price Total Monthly Price New
    Base Rent$3,400 - $3,550
    Required Monthly FeesNone
    Total Monthly Price$3,400 - $3,550
    - 12 Month Lease

    7 High Street Pl

    7 High Street Pl, Brookline, MA 02445
  27. 2 BEDS, 1 BATH
    $3,600
    Total Monthly Price Total Monthly Price New
    Base Rent$3,600
    Required Monthly FeesNone
    Total Monthly Price$3,600
    - 12 Month Lease

    49 Boylston St Unit 2

    49 Boylston St, Brookline, MA 02445
  28. 2 BEDS, 2 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

    36 Davis Ave

    36 Davis Ave, Brookline, MA 02445
  29. 2 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 Month Lease

    215 Cypress St

    215 Cypress St, Brookline, MA 02445
  30. 2 BEDS, 1 BATH
    $2,850
    Total Monthly Price Total Monthly Price New
    Base Rent$2,850
    Required Monthly FeesNone
    Total Monthly Price$2,850
    - 12 Month Lease

    231 High St Unit 1

    231 High St, Brookline, MA 02445
  31. 2 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

    77 Pond Ave Unit 306

    77 Pond Ave, Brookline, MA 02445
  32. 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
    - 12 Month Lease

    7 High Street Pl Unit 2

    7 High Street Pl, Brookline, MA 02445
  33. 2 BEDS, 1 BATH
    $4,000
    Total Monthly Price Total Monthly Price New
    Base Rent$4,000
    Required Monthly FeesNone
    Total Monthly Price$4,000
    - 12 Month Lease

    46 Cameron St Unit 2

    46 Cameron St, Brookline, MA 02445
  34. 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
    - 12 Month Lease

    7 High Street Pl Unit 2##

    7 High Street Pl, Brookline, MA 02445
  35. 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
    - 12 Month Lease

    7 Rice St Unit #1

    7 Rice St, Brookline, MA 02445
  36. 2 BEDS, 1 BATH
    $4,300
    Total Monthly Price Total Monthly Price New
    Base Rent$4,300
    Required Monthly FeesNone
    Total Monthly Price$4,300
    - 12 Month Lease

    40 Cameron St Unit 1

    40 Cameron St, Brookline, MA 02445
  37. 2 BEDS, 1 BATH
    $3,300
    Total Monthly Price Total Monthly Price New
    Base Rent$3,300
    Required Monthly FeesNone
    Total Monthly Price$3,300
    - 12 Month Lease

    86 Chestnut St Unit 2

    86 Chestnut St, Brookline, MA 02445
  38. 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
    - 12 Month Lease

    7 High Street Pl Unit 2

    7 High Street Pl, Brookline, MA 02445
  39. 2 BEDS, 1 BATH
    $3,300
    Total Monthly Price Total Monthly Price New
    Base Rent$3,300
    Required Monthly FeesNone
    Total Monthly Price$3,300
    - 12 Month Lease

    6 Smythe St Unit 2

    6 Smythe St, Brookline, MA 02445
  40. 2 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 Month Lease

    234 Cypress St Unit 3

    234 Cypress St, Brookline, MA 02445
  41. 2 BEDS, 1 BATH
    $4,300
    Total Monthly Price Total Monthly Price New
    Base Rent$4,300
    Required Monthly FeesNone
    Total Monthly Price$4,300
    - 12 Month Lease

    14 Smythe St Unit 4

    14 Smythe St, Brookline, MA 02445
Showing 42 of 91 results, Page 1 of 3

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High Street Hill Neighborhood in Brookline, MA

So you're looking for the perfect two-bedroom apartment for rent in High Street Hill. With great rent specials, price drops, and the best values in the city, Apartment Finder offers a wide selection of spacious two-bedroom apartments that will fit your lifestyle and budget. Two-bedroom apartments' larger layout and versatile living spaces provide ample room for individuals, couples, or even small families in High Street Hill.

With the shared cost of rent, two-bedroom apartments offer great value for the space you get. Even if you're not searching with roommates, a two-bedroom apartment has practical benefits. Experience the advantages of having an extra bedroom, whether for a home office, guest room, or added storage space. The flexibility of a second bedroom allows you to personalize your home and adapt to changing needs. Enjoy a larger living area, multiple closets, and potentially additional amenities like balconies or in-unit laundry. Choose any of these 91 two-bedroom apartments for rent to view floor plans, see photos, and get more information on amenities and availability.

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