select distinct Value when using left join and order by on two tables

You can use aggregate functions in ORDER BY:

SELECT shops.id AS shopid -- No need to use MAX(...) here
FROM shops 
LEFT JOIN expiration ON shops.id=expiration.shopid
GROUP BY shopid
ORDER BY
  MAX(shops.grade) DESC,
  MIN(expiration.startdate) ASC,
  MAX(expiration.enddate) DESC,
  shops.id