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  1. Building Photo - 8 Curtis St
    1 BED, 1 BATH
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000
         - 12 Month Lease

    8 Curtis St Unit 6

    8 Curtis St, Boston, MA 02128
    Apply
  2. Building Photo - 1030 Bennington St
    1 BED, 1 BATH
    $2,095
    Total Monthly Price Total Monthly Price New
    Base Rent$2,095
    Required Monthly FeesNone
    Total Monthly Price$2,095
         - 12 Month Lease

    1030 Bennington St Unit 15

    1030 Bennington St, Boston, MA 02128
    Apply
  3. 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
         - 12 Month Lease

    44 Ashley St Unit 4-bed2bath

    44 Ashley St, Boston, MA 02128
    Apply
  4. 1 BED, 1 BATH
    $1,800
    Total Monthly Price Total Monthly Price New
    Base Rent$1,800
    Required Monthly FeesNone
    Total Monthly Price$1,800
         - 12 Month Lease

    129 Bradstreet Ave Unit 3

    129 Bradstreet Ave, Revere, MA 02151
    Apply
  5. 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
         - 12 Month Lease

    97 Addison St Unit 204

    97 Addison St, Boston, MA 02128
    Apply
  6. 1 BED, 1 BATH
    $2,500+
    2 BEDS, 1 BATH
    $3,200+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500 - $3,200
    Required Monthly FeesNone
    Total Monthly Price$2,500 - $3,200
         - 12 Month Lease

    5 Fremont St

    5 Fremont St, Winthrop, MA 02152
  7. 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
         - 12 Month Lease

    12 Sewall Ave Unit 3

    12 Sewall Ave, Winthrop, MA 02152
  8. 2 BEDS, 1 BATH
    $2,650
    Total Monthly Price Total Monthly Price New
    Base Rent$2,650
    Required Monthly FeesNone
    Total Monthly Price$2,650
         - 12 Month Lease

    288 Pleasant St Unit 1

    288 Pleasant St, Winthrop, MA 02152
  9. 4 BEDS, 2 BATHS
    $3,400
    Total Monthly Price Total Monthly Price New
    Base Rent$3,400
    Required Monthly FeesNone
    Total Monthly Price$3,400
         - 12 Month Lease

    183 Cottage Park Rd Unit 3

    183 Cottage Park Rd, Winthrop, MA 02152
  10. STUDIO, 1 BATH
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650
         - 12 Month Lease

    85 Winthrop Shore Dr

    85 Winthrop Shore Dr, Winthrop, MA 02152
  11. Discounts
    Discounts
    STUDIO, 1 BATH
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850
         - 12 Month Lease

    95 Bowdoin St Unit 3

    95 Bowdoin St, Winthrop, MA 02152
  12. 2 BEDS, 1 BATH
    $2,600
    Total Monthly Price Total Monthly Price New
    Base Rent$2,600
    Required Monthly FeesNone
    Total Monthly Price$2,600
         - 12 Month Lease

    439 Winthrop St Unit 1

    439 Winthrop St, Winthrop, MA 02152
  13. 2 BEDS, 1 BATH
    $2,600
    Total Monthly Price Total Monthly Price New
    Base Rent$2,600
    Required Monthly FeesNone
    Total Monthly Price$2,600
         - 12 Month Lease

    439 Winthrop St Unit 1

    439 Winthrop St, Winthrop, MA 02152
  14. 3 BEDS, 3 BATHS
    $4,995
    Total Monthly Price Total Monthly Price New
    Base Rent$4,995
    Required Monthly FeesNone
    Total Monthly Price$4,995
         - 12 Month Lease

    176 Winthrop Shore Dr Unit 1

    176 Winthrop Shore Dr, Winthrop, MA 02152
  15. 2 BEDS, 1 BATH
    $2,200
    Total Monthly Price Total Monthly Price New
    Base Rent$2,200
    Required Monthly FeesNone
    Total Monthly Price$2,200
         - 12 Month Lease

    40 Dolphin Ave Unit #2

    40 Dolphin Ave, Winthrop, MA 02152
  16. 2 BEDS, 1 BATH
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500
         - 12 Month Lease

    233 Pleasant St Unit Apt 2

    233 Pleasant St, Winthrop, MA 02152
  17. 4 BEDS, 2 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

    40 Cottage Park Rd Unit 1

    40 Cottage Park Rd, Winthrop, MA 02152
  18. 1 BED, 1 BATH
    $2,550
    Total Monthly Price Total Monthly Price New
    Base Rent$2,550
    Required Monthly FeesNone
    Total Monthly Price$2,550
         - 12 Month Lease

    15 Walley St Unit 206

    15 Walley St, Boston, MA 02128
  19. 4 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

    90 Gladstone St Unit 1

    90 Gladstone St, Boston, MA 02128
  20. 1 BED, 1 BATH
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100
         - 12 Month Lease

    789 Saratoga St Unit #3

    789 Saratoga St, Boston, MA 02128
  21. 4 BEDS, 1 BATH
    $3,800
    Total Monthly Price Total Monthly Price New
    Base Rent$3,800
    Required Monthly FeesNone
    Total Monthly Price$3,800
         - 12 Month Lease

    1 Orient Ave Unit 3C

    1 Orient Ave, Boston, MA 02128
  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

    1030 Bennington St Unit 5

    1030 Bennington St, Boston, MA 02128
  23. 2 BEDS, 1 BATH
    $2,550
    Total Monthly Price Total Monthly Price New
    Base Rent$2,550
    Required Monthly FeesNone
    Total Monthly Price$2,550
         - 12 Month Lease

    117 Addison St Unit #1

    117 Addison St, Boston, MA 02128
  24. 2 BEDS, 1 BATH
    $2,600
    Total Monthly Price Total Monthly Price New
    Base Rent$2,600
    Required Monthly FeesNone
    Total Monthly Price$2,600
         - 12 Month Lease

    1021 Winthrop Ave Unit #2

    1021 Winthrop Ave, Revere, MA 02151
  25. 2 BEDS, 2 BATHS
    $2,850
    Total Monthly Price Total Monthly Price New
    Base Rent$2,850
    Required Monthly FeesNone
    Total Monthly Price$2,850
         - 12 Month Lease

    661 Bennington St Unit #3

    661 Bennington St, Boston, MA 02128
  26. 2 BEDS, 1.5 BATHS
    $2,850
    Total Monthly Price Total Monthly Price New
    Base Rent$2,850
    Required Monthly FeesNone
    Total Monthly Price$2,850
         - 12 Month Lease

    77 Byron St Unit 2

    77 Byron St, Boston, MA 02128
  27. 1 BED, 1 BATH
    $2,400
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400
    Required Monthly FeesNone
    Total Monthly Price$2,400
         - 12 Month Lease

    25 Pratt St Unit 1

    25 Pratt St, Boston, MA 02134
  28. 2 BEDS, 1 BATH
    $2,750
    Total Monthly Price Total Monthly Price New
    Base Rent$2,750
    Required Monthly FeesNone
    Total Monthly Price$2,750
         - 12 Month Lease

    92 Winthrop Shore Dr Unit 2

    92 Winthrop Shore Dr, Winthrop, MA 02152
  29. 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

    184 Gladstone St Unit 1

    184 Gladstone St, Boston, MA 02128
  30. 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

    115 Moore St Unit 1

    115 Moore St, Boston, MA 02128
  31. 1 BED, 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

    93 Cowper St Unit 3

    93 Cowper St, Boston, MA 02128
  32. 3 BEDS, 1 BATH
    $3,400
    Total Monthly Price Total Monthly Price New
    Base Rent$3,400
    Required Monthly FeesNone
    Total Monthly Price$3,400
         - 12 Month Lease

    215 Leyden St Unit 1

    215 Leyden St, Boston, MA 02128
  33. 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

    1030 Bennington St Unit 5

    1030 Bennington St, Boston, MA 02128
  34. 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

    663 Bennington St Unit 2

    663 Bennington St, Boston, MA 02128
  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

    678 Bennington St Unit 1

    678 Bennington St, Boston, MA 02128
  36. 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
         - 12 Month Lease

    823 Saratoga St Unit 2

    823 Saratoga St, Boston, MA 02128
  37. 2 BEDS, 1 BATH
    $2,650
    Total Monthly Price Total Monthly Price New
    Base Rent$2,650
    Required Monthly FeesNone
    Total Monthly Price$2,650
         - 12 Month Lease

    108 Byron St Unit A

    108 Byron St, Boston, MA 02128
  38. 3 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

    723 Bennington St Unit #1

    723 Bennington St, Boston, MA 02128
  39. 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

    1030 Bennington St Unit 5

    1030 Bennington St, Boston, MA 02128
  40. 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

    661 Bennington St Unit 2

    661 Bennington St, Boston, MA 02128
  41. 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

    1030 Bennington St Unit 5

    1030 Bennington St, Boston, MA 02128
  42. 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
         - 12 Month Lease

    44 Ashley St

    44 Ashley St, Boston, MA 02128
Showing 42 of 172 results, Page 2 of 5

Winthrop at a Glance

Average Rent

$2,291
(All bedrooms and property types)
Learn more about
Average Rent in Winthrop
7

School Rating

out of 10 Rating
Learn more about
Schools in Winthrop
1

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Winthrop
44

Somewhat Bikeable

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

Renting in Winthrop

Average Rental Rates and Apartment Sizes

Average Rent in Nearby Cities

(For 1 bedroom apartments)

Getting Around Winthrop

Transportation

76

Very Walkable

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.
44

Somewhat 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.
1

Minimal 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

GreatSchools Rating
Winthrop Sr High School

Public High School

Public
Grades 9-12
594 Students
GreatSchools Rating
Winthrop Middle School

Public Middle School

Public
Grades 6-8
425 Students
GreatSchools Rating
Arthur T. Cummings Elementary School

Public Elementary School

Public
Grades 3-5
431 Students

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

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