Yes He did.
Jesus' Teaching Elsewhere
Luke 16:19-31 19 There was a certain rich man, who was clothed in purple and fine linen; and feasted sumptuously every day. 20 And there was a certain beggar, named Lazarus, who lay at his gate, full of sores, 21 Desiring to be filled with the crumbs that fell from the rich man's table, and no one did give him; moreover the dogs came, and licked his sores. 22 And it came to pass, that the beggar died, and was carried by the angels into Abraham's bosom. And the rich man also died: and he was buried in hell. 23 And lifting up his eyes when he was in torments, he saw Abraham afar off, and Lazarus in his bosom: 24 And he cried, and said: Father Abraham, have mercy on me, and send Lazarus, that he may dip the tip of his finger in water, to cool my tongue: for I am tormented in this flame. 25 And Abraham said to him: Son, remember that thou didst receive good things in thy lifetime, and likewise Lazareth evil things, but now he is comforted; and thou art tormented. 26 And besides all this, between us and you, there is fixed a great chaos: so that they who would pass from hence to you, cannot, nor from thence come hither. 27 And he said: Then, father, I beseech thee, that thou wouldst send him to my father's house, for I have five brethren, 28 That he may testify unto them, lest they also come into this place of torments. 29 And Abraham said to him: They have Moses and the prophets; let them hear them. 30 But he said: No, father Abraham: but if one went to them from the dead, they will repent. 31 And he said to him: If they hear not Moses and the prophets, neither will they believe, if one rise again from the dead.
Clearly there is a spiritual abode where the spirits of the departed can feel and sense in whatever way they do so. Moreover, it is a place of conscious torment. Jesus also assumes that this is common knowledge, since we only know this from inference, and no ado is made about the concept, either in the passage itself, or in church history, where it is also assumed.
Paul/Author of Hebrews
Hebrews 12:22-24 But you are come to mount Zion, and to the city of the living God, the heavenly Jerusalem, and to the company of many thousands of angels, 23 And to the church of the firstborn, who are written in the heavens, and to God the judge of all, and to the spirits of the righteous made perfect, 24 And to Jesus the mediator of the new testament, and to the sprinkling of blood which speaketh better than that of Abel.
This must refer to the human souls of those yet to be resurrected at the Final Judgement, but who have gone to heaven. So the author, probably Paul via Luke, believes in Christian departed spirits, who are presumably in heaven, with the many thousands of angels, or who are at least in communion with them and dead (for no human is only a spirit, except a deceased one).
The Old Testament
In the Old Testament, we read that the soul of Samuel was summoned, presumably from said abode (presumably the same "Bosom of Abraham"), or at least what we would call "the [place] of the dead" (usually translated "the dead" as in "from the dead"):
1 Samuel 28:3-20 Now Samuel was dead, and all Israel mourned for him, and buried him in Ramatha his city. And Saul had put away all the magicians and soothsayers out of the land. 4 And the Philistines were gathered together, and came and camped in Sunam: and Saul also gathered together all Israel, and came to Gelboe. 5 And Saul saw the army of the Plilistines, and was afraid, and his heart was very much dismayed.
6 And he consulted the Lord, and he answered him not, neither by dreams, nor by priests, nor by prophets. 7 And Saul said to his servants: Seek me a woman that hath a divining spirit, and I will go to her, and inquire by her. And his servants said to him: There is a woman that hath a divining spirit at Endor. 8 Then he disguised himself: and put on other clothes, and he went, and two men with him, and they came to the woman by night, and he said to her: Divine to me by thy divining spirit, and bring me up him whom I shall tell thee. 9 And the woman said to him: Behold thou knowest all that Saul hath done, and how he hath rooted out the magicians and soothsayers from the land: why then dost thou lay a snare for my life, to cause me to be put to death? 10 And Saul swore unto her by the Lord, saying: As the Lord liveth there shall no evil happen to thee for this thing. 11 And the woman said to him: Whom shall I bring up to thee? And he said, Bring me up Samuel. 12 And when the woman saw Samuel, she cried out with a loud voice, and said to Saul: Why hast thou deceived me? for thou art Saul. 13 And the king said to her: Fear not: what hast thou seen? And the woman said to Saul: I saw gods ascending out of the earth. 14 And he said to her: What form is he of? And she said: An old man cometh up, and he is covered with a mantle. And Saul understood that it was Samuel, and he bowed himself with his face to the ground, and adored. 15 And Samuel said to Saul: Why hast thou disturbed my rest, that I should be brought up? And Saul said, I am in great distress: for the Philistines fight against me, and God is departed from me, and would not hear me, neither by the hand of prophets, nor by dreams: therefore I have called thee, that thou mayest shew me what I shall do. 16 And Samuel said: Why askest thou me, seeing the Lord has departed from thee, and is gone over to thy rival: 17 For the Lord will do to thee as he spoke by me, and he will rend thy kingdom out of thy hand, and will give it to thy neighbour David: 18 Because thou didst not obey the voice of the Lord, neither didst thou execute the wrath of his indignation upon Amalec. Therefore hath the Lord done to thee what thou sufferest this day. 19 And the Lord also will deliver Israel with thee into the hands of the Philistines: and to morrow thou and thy sons shall be with me: and the Lord will also deliver the army of Israel into the hands of the Philistines. 20 And forthwith Saul fell all along on the ground, for he was frightened with the words of Samuel, and there was no strength in him, for he had eaten no bread all that day.
So clearly this is no false apparition, and God allowed the soul of Samuel to visit Saul: inasmuch as God can do what He wills with any soul: "Behold, all souls are mine; the soul of the father as well as the soul of the son is mine" (Ezekiel 18:4). This is also proven by the fact that the truth was really revealed to the diviner by the person she saw, namely, Samuel, and that the author of Scripture clearly calls him "Samuel" — "the words of Samuel" and "Samuel said"). And yet Samuel was dead.
John the Revelator
In the book of Revelation we read:
Revelation 6:9-10 And when he had opened the fifth seal, I saw under the altar the souls of them that were slain for the word of God, and for the testimony which they held. And they cried with a loud voice, saying: How long, O Lord, holy and true, dost thou not judge and revenge our blood on them that dwell on the earth?
Acts of the Apostles
In Acts we read that the souls of the dead go to hell, and are thus, like the spirits of devils, able to be plucked from thence or otherwise make their presence known here on earth (i.e. like devils). We learn this from inference and from the tradition affirmed by the apostles but not otherwise explicit in Scripture, namely that "abandoned to sheol" must refer to a long or indefinite stay in a spiritual abode, because it is used of Jesus, and we know that He went to a spiritual abode called a "prison," presumably the same above spoken of above:
Acts 2:24-32 Whom God hath raised up, having loosed the sorrows of hell, as it was impossible that he should be holden by it. 25 For David saith concerning him: I foresaw the Lord before my face: because he is at my right hand, that I may not be moved. 26 For this my heart hath been glad, and any tongue hath rejoiced: moreover my flesh also shall rest in hope. 27 Because thou wilt not leave my soul in hell, nor suffer thy Holy One to see corruption. 28 Thou hast made known to me the ways of life: thou shalt make me full of joy with thy countenance. 29 Ye men, brethren, let me freely speak to you of the patriarch David; that he died, and was buried; and his sepulchre is with us to this present day. 30 Whereas therefore he was a prophet, and knew that God hath sworn to him with an oath, that of the fruit of his loins one should sit upon his throne. 31 Foreseeing this, he spoke of the resurrection of Christ. For neither was he left in hell, neither did his flesh see corruption. 32 This Jesus hath God raised again, whereof all we are witnesses.
As for proof that Jesus was in hell, although not "left" there (where one is has "sorrows"), but to arise three days later from there, we read in Peter's Epistle:
1 Peter 3:18-20 Because Christ also died once for our sins, the just for the unjust: that he might offer us to God, being put to death indeed in the flesh, but enlivened in the spirit, in which also coming he preached to those spirits that were in prison: which had been some time incredulous, when they waited for the patience of God in the days of Noah, when the ark was a building: wherein a few, that is, eight souls, were saved by water.
Of course "hell" here is used of the abode of the dead, and not of the 'hell of the damned' i.e. that region of hell, or that hell where, the damned endure eternal tormet in the "everlasting fire prepared for the devil and his angels" (Matthew 25:41).
Pre-Christian Jewish Texts
2 Maccabees 15:12-14 Now the vision was in this manner: Onijah who had been high priest, a good and virtuous man, modest in his looks, gentle in his manners, and graceful in his speech, and who from a child was exercised in virtues, holding up his hands, prayed for all the people of the Jews: 13 After this there appeared also another man, admirable for age, and glory, and environed with great beauty and majesty: 14 Then Onias answering, said: This is a lover of his brethren, and of the people of Israel: this is he that prayeth much for the people, and for all the holy city, Jeremiah the prophet of God.
Around 150BC, reliable or at least orthodox tradition of the Jews (2 Maccabees) spoke of deceased prophets praying for the people of God on earth, and their victory in battle against the heathen, as well as a pious yet deceased priest, Onijah. 2 Maccabees is part of the Bible according to most Christians except Protestants (and Jews, who also reject all 27 books of the New Testament), so I chose this instead of some other pre-Christian texts many of which also, presumably, mention the same kind of thing. This quite clearly appears to be a disembodied spirit conscious and active in their concern for the afairs of those on earth (as in Revelation 6:9-10; cf. Hebrews 12:23).
