Conditions in automation!

(summer AND after 20:00:00) OR (Winter AND after 17:00:00)
  condition:
    condition: or
    conditions:
      - condition: and
        conditions:
        - condition: state
          entity_id: sensor.season
          state: 'summer'
        - condition: time
          after: '20:00:00'
      - condition: and
        conditions:
        - condition: state
          entity_id: sensor.season
          state: 'winter'
        - condition: time
          after: '17:00:00'

EDIT
Correction: The Season component’s state is in lower case text (summer), not propercase (Summer).