Note: Properties with the Total Monthly Price badge include all required fees. Tap the badge for more details.
-

Bedrooms

Bathrooms

Deals & Discount Filters
All Filters

Deals & Discounts

Price Range

–

Beds & Baths

Beds

Baths

Home Type

Pet Policy

Interior & Community Amenities

Speciality Housing

Keyword Search

  1. Building Photo - 44 Ashley St
    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
  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. 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

    573 Shirley St Unit 1

    573 Shirley St, Winthrop, MA 02152
  4. 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
  5. 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

    76 Fremont St Unit 3

    76 Fremont St, Winthrop, MA 02152
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 2 BEDS, 1 BATH
    $2,895
    Total Monthly Price Total Monthly Price New
    Base Rent$2,895
    Required Monthly FeesNone
    Total Monthly Price$2,895
         - 12 Month Lease

    82 Gladstone St Unit 2

    82 Gladstone St, Boston, MA 02128
  18. 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
  19. 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
  20. 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
  21. 3 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

    630 Bennington St Unit 3

    630 Bennington St, Boston, MA 02128
  22. 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
  23. 4 BEDS, 2 BATHS
    $4,250
    Total Monthly Price Total Monthly Price New
    Base Rent$4,250
    Required Monthly FeesNone
    Total Monthly Price$4,250
         - 12 Month Lease

    25 Pratt St Unit 2

    25 Pratt St, Boston, MA 02134
  24. 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
  25. 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
  26. 3 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

    120 Gladstone St Unit #3

    120 Gladstone St, Boston, MA 02128
  27. 4 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

    31 Faywood Ave Unit 2

    31 Faywood Ave, Boston, MA 02128
  28. 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
  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

    678 Bennington St Unit 1

    678 Bennington St, Boston, MA 02128
  30. 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
  31. 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
  32. 1 BED, 1 BATH
    $2,400+
    3 BEDS, 1 BATH
    $3,600+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400 - $3,600
    Required Monthly FeesNone
    Total Monthly Price$2,400 - $3,600
         - 12 Month Lease

    25 Pratt St

    25 Pratt St, Boston, MA 02134
  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, 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

    125 Addison St Unit #1

    125 Addison St, Boston, MA 02128
  35. 2 BEDS, 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

    83 Bradstreet Ave Unit #202

    83 Bradstreet Ave, Revere, MA 02151
  36. 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
  37. 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
  38. 2 BEDS, 2 BATHS
    $3,995
    Total Monthly Price Total Monthly Price New
    Base Rent$3,995
    Required Monthly FeesNone
    Total Monthly Price$3,995
         - 12 Month Lease

    37 Horace St Unit 3

    37 Horace St, Boston, MA 02128
  39. 4 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

    31 Faywood Ave Unit 3

    31 Faywood Ave, Boston, MA 02128
  40. 3 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

    1110 Saratoga St Unit 1

    1110 Saratoga St, Boston, MA 02128
  41. 2 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

    37 Horace St Unit 3

    37 Horace St, Boston, MA 02128
  42. 1 BED, 1 BATH
    $2,150+
    3 BEDS, 1 BATH
    $3,300+
    Total Monthly Price Total Monthly Price New
    Base Rent$2,150 - $3,300
    Required Monthly FeesNone
    Total Monthly Price$2,150 - $3,300
         - 12 Month Lease

    25 Pratt St

    25 Pratt St, Boston, MA 02134
Showing 42 of 160 results, Page 2 of 4

Winthrop at a Glance

Average Rent

$2,292
(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.

tooltips

I would like to...
0 out of 400 characters
By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to... By clicking above, you agree we may pass along your info so this property or the property’s affiliates can email, call, text, or autodial you to follow up and for any purpose. You also agree to Apartmentfinder.com’s Privacy Statement and Terms of Service. Consent is not a condition for services. Message and data rates may apply. Read More Read Less

Submitting Request

Thank You

Your email has been sent.

Learn about our ratings.