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Two Bedroom Condos for Rent in High Street Hill

92 Rentals
.
  4. 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
         - 12 Month Lease

    14 Smythe St Unit 3

    14 Smythe St, Brookline, MA 02445
    Apply
  5. Building Photo - 33 Pond Ave
    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
         - 3 Month Lease

    33 Pond Ave

    33 Pond Ave, Brookline, MA 02445
    Apply
  6. 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
    Apply
  7. 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
    Apply
  8. 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 1

    7 High Street Pl, Brookline, MA 02445
    Apply
  9. 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

    7 Harvard Sq Unit 3B

    7 Harvard Sq, Brookline, MA 02445
    Apply
  10. 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
    Apply
  11. 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
    Apply
  12. 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

    199 Boylston St Unit 1

    199 Boylston St, Brookline, MA 02445
    Apply
  13. 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
    Apply
  14. 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

    7 Rice St Unit 1

    7 Rice St, Brookline, MA 02445
    Apply
  15. 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

    199 Boylston St Unit 1

    199 Boylston St, Brookline, MA 02445
    Apply
  16. 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

    199 Boylston St Unit 1

    199 Boylston St, Brookline, MA 02445
    Apply
  17. 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

    14 Smythe St

    14 Smythe St, Brookline, MA 02445
    Apply
  18. 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
         - 12 Month Lease

    85 Chestnut St Unit 2

    85 Chestnut St, Brookline, MA 02445
    Apply
  19. 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

    14 Smythe St Unit 3

    14 Smythe St, Brookline, MA 02445
    Apply
  20. 2 BEDS, 2 BATHS
    $3,600
    Total Monthly Price Total Monthly Price New
    Base Rent$3,600
    Required Monthly FeesNone
    Total Monthly Price$3,600
         - 12 Month Lease

    20 Cameron ST 303 Unit 303

    20 Cameron ST 303, Brookline, MA 02445
    Apply
  21. 2 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
         - 12 Month Lease

    5 Davis Ave Unit 6

    5 Davis Ave, Brookline, MA 02445
  22. 2 BEDS, 1 BATH
    $2,700
    Total Monthly Price Total Monthly Price New
    Base Rent$2,700
    Required Monthly FeesNone
    Total Monthly Price$2,700
         - 12 Month Lease

    19 Roberts St

    19 Roberts St, Brookline, MA 02445
  23. 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
  24. 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
  25. 2 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
         - 12 Month Lease

    5 Davis Ave Unit 6

    5 Davis Ave, Brookline, MA 02445
  26. 2 BEDS, 1 BATH
    $6,500
    Total Monthly Price Total Monthly Price New
    Base Rent$6,500
    Required Monthly FeesNone
    Total Monthly Price$6,500
         - 12 Month Lease

    91 Chestnut St Unit 6

    91 Chestnut St, Brookline, MA 02445
  27. 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 2

    234 Cypress St, Brookline, MA 02445
  28. 2 BEDS, 1 BATH
    $3,100
    Total Monthly Price Total Monthly Price New
    Base Rent$3,100
    Required Monthly FeesNone
    Total Monthly Price$3,100
         - 12 Month Lease

    14 Smythe St Unit 3

    14 Smythe St, Brookline, MA 02445
  29. 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
         - 12 Month Lease

    20 Cameron St Unit 303

    20 Cameron St, Brookline, MA 02445
  30. 2 BEDS, 2 BATHS
    $3,500
    Total Monthly Price Total Monthly Price New
    Base Rent$3,500
    Required Monthly FeesNone
    Total Monthly Price$3,500
         - 12 Month Lease

    22 Chestnut Pl Unit 114

    22 Chestnut Pl, Brookline, MA 02445
  31. 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

    7 Rice St Unit 1

    7 Rice St, Brookline, MA 02445
  32. 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
  33. 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
  34. 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
  35. 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
  36. 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
  37. 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
  38. 2 BEDS, 2 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

    323 Boylston St Unit 3

    323 Boylston St, Brookline, MA 02445
  39. 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
  40. 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

    77 Pond Ave Unit #902

    77 Pond Ave, Brookline, MA 02445
  41. 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

    98 Cypress St Unit 2

    98 Cypress St, Brookline, MA 02445
  42. 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

    77 Walnut St, Brookline, MA 02445
Showing 42 of 83 results, Page 1 of 2

Brookline at a Glance

Average Rent

N/A
(All bedrooms and property types)
0

School Rating

out of 10 Rating
Learn more about
Schools in Brookline
73

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Brookline
86

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Brookline

High Street Hill Neighborhood in Brookline, MA

So you're looking for the perfect two-bedroom condo 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 condos that will fit your lifestyle and budget. The larger layout and versatile living spaces in two-bedroom rentals provide ample room for individuals, couples, or even small families in High Street Hill.

With the shared cost of rent, two-bedroom condos offer great value for the space you get. A two-bedroom rental has practical benefits even if you're not searching with roommates. 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 in-unit laundry. Choose any of these 83 two-bedroom condos for rent to view floor plans, see photos, and get more information on amenities and availability.

Top Budget-Friendly Neighborhoods in Brookline

(For 1 bedroom apartments)

Getting Around Brookline

Transportation

92

Walker’s Paradise

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
86

Very Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
73

Excellent Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Scoreⓘ

Education

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

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