EXHIBIT 5

              [LETTERHEAD OF HOUSLEY KANTARIAN & BRONSTEIN, P.C.]



                               December 23, 1996



Board of Directors
Cumberland Mountain Bancshares, Inc.
1431 Cumberland Avenue
Middlesboro, Kentucky  40961

     RE:  Registration Statement on Form SB-2

Ladies and Gentlemen:

     You have requested our opinion as special counsel to Cumberland Mountain
Bancshares, Inc. (the "Corporation") in connection with the Registration
Statement on Form SB-2 to be filed with the Securities and Exchange Commission
under the Securities Act of 1933, as amended (the "Registration Statement").
The Registration Statement relates to shares of common stock of the Corporation
(the "Common Stock") to be issued in connection with the conversion of
Cumberland Mountain Bancshares, M.H.C. from mutual form to an interim stock
savings bank, its subsequent merger with and into Middlesboro Federal Bank,
Federal Savings Bank (the "Bank") with the Bank as the surviving entity and the
subsequent reorganization of the Bank as a wholly owned subsidiary of the
Corporation (collectively the "Conversion and Reorganization").

     In rendering this opinion, we understand that the Common Stock will be
offered and sold in the manner described in the Prospectus which is a part of
the Registration Statement.  We have examined such records and documents and
made such examination as we have deemed relevant in connection with this
opinion.

     Based upon the foregoing, it is our opinion that the shares of Common Stock
will, when issued and sold as contemplated by the Registration Statement, be
legally issued, fully paid and nonassessable.

     We hereby consent to the filing of this opinion as an exhibit to the
Registration Statement and to the reference to us in the Prospectus under the
heading "Legal Matters."

                                   HOUSLEY KANTARIAN & BRONSTEIN, P.C.



                                   By: /s/ James C. Stewart
                                       --------------------------------------
                                       James C. Stewart