How do I split addresses with no commas, and irregular layouts in a Pandas data frame?

I have a column in a data frame like this (it includes many more address):

How can I separate these addresses into 2 columns, so that it has the number and street address in one column, and the city, state, zip in another like this:

I have tried doing this by separating everything by space from the right, but some towns include two words in their names, and thus this way does not work.

# put zip code into separate column
        clean_df[['prop_addressLine1','Owner Zip']] = clean_df['Owner Address'].str.rsplit(' ', n=1, expand=True)

        # separate street, city, and state into their own columns:
        clean_df[['Owner Street','Owner City','Owner State']] = clean_df['prop_addressLine1'].str.rsplit(' ', n=2, expand=True)

I was thinking of separating everything into separate columns by space, but there are irregular spaces, and I have not figured out how to make it work.

One option is to use the street type abbreviations (Ct/Pl/Rd) as delimiters and to extract the two parts:

df[['Address 1', 'Address 2']] = (df['Address'].str
                                  .extract('^(.*?(?:Pl|Ct|Rd)) (.*)$')
                                 )

If you want to handle more complex addresses, you'll need a parser. For example with usaddress:

import usaddress

def address_split(addr):
    address1 = []
    address2 = []
    flag = False
    for val, k in usaddress.parse(addr):
        if k == 'PlaceName':
            flag = True
        if flag:
            address2.append(val)
        else:
            address1.append(val)
    return ' '.join(address1), ' '.join(address2)


df['Address 1'], df['Address 2'] = list(zip(*map(address_split, df['Address'])))

Output:

                                Address       Address 1               Address 2
0  287 Andover Pl Robbinsville NJ 08691  287 Andover Pl   Robbinsville NJ 08691
1    1 Oxford Ct Princeton Jct NJ 08550     1 Oxford Ct  Princeton Jct NJ 08550
2  244 N Post Rd Princeton Jct NJ 08550   244 N Post Rd  Princeton Jct NJ 08550
3      3 Gates Ct West Windsor NJ 08550      3 Gates Ct   West Windsor NJ 08550

Intermediate with usaddress.parse:

# usaddress.parse('244 N Post Rd Princeton Jct NJ 08550')

[('244', 'AddressNumber'),
 ('N', 'StreetNamePreDirectional'),
 ('Post', 'StreetName'),
 ('Rd', 'StreetNamePostType'),
 ('Princeton', 'PlaceName'),
 ('Jct', 'PlaceName'),
 ('NJ', 'StateName'),
 ('08550', 'ZipCode')]