As filed with the Securities and Exchange Commission on July 1, 1999
Registration No. 333-____________

SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549

FORM S-8

REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933

ENTERBANK HOLDINGS, INC.
(Exact name of registrant as specified in its charter)

            DELAWARE                                 43-1706259
            --------                                 ----------
(State or other jurisdiction of                   (I.R.S. Employer
 incorporation or organization)                 Identification No.)

150 NORTH MERAMEC
CLAYTON, MISSOURI 63105
(314) 725-5500
(Address, Including Zip Code and Telephone Number,
of Principal Executive Offices)

OPTIONS GRANTED UNDER THE AGREEMENT BETWEEN ENTERBANK HOLDINGS, INC.,

ENTERPRISE BANK, AND MONETA GROUP INVESTMENT ADVISORS, INC.

ENTERBANK HOLDINGS, INC. NON-QUALIFIED INCENTIVE STOCK OPTION PLAN

ENTERBANK HOLDINGS, INC. FOURTH INCENTIVE STOCK OPTION PLAN

                          (Full title of the plans)
                                                       Copy To:
          FRED H. ELLER                           DAVID W. BRASWELL
     ENTERBANK HOLDINGS, INC.                   ARMSTRONG TEASDALE LLP
        150 NORTH MERAMEC                ONE METROPOLITAN SQUARE; SUITE 2600
     CLAYTON, MISSOURI  63105              ST. LOUIS, MISSOURI  63102-2740
          (314) 725-5500                            (314) 621-5070
          --------------                            --------------
(Name, Address, and Telephone Number,

Including Area Code, of Agent For Service)





                                            CALCULATION OF REGISTRATION FEE
-----------------------------------------------------------------------------------------------------------------------------------
                                                                              Proposed             Proposed maximum    Amount of
  Title of securities to be registered                Amount of shares        maximum offering     aggregate offering  registration
                                                      to be registered<F1>    price per share<F2>  price<F2>           fee
-----------------------------------------------------------------------------------------------------------------------------------
  Common Stock, par value $.01 per share               30,600 shares <F3>     $31.00               $1,024,860          $  284.91
  Common Stock, par value $.01 per share              166,940 shares <F4>     $42.00               $7,011,480          $1,949.19
  Common Stock, par value $.01 per share               23,000 shares <F5>     $30.00               $690,000            $  191.82
  Common Stock, par value $.01 per share                5,000 shares <F6>     $31.00               $155,000            $   43.09
  Common Stock, par value $.01 per share                7,000 shares <F7>     $42.00               $294,000            $   81.73
  Common Stock, par value $.01 per share              200,000 shares <F8>     $42.00               $8,400,000          $2,335.20
                                                      --------------                               ----------          ---------
                                  TOTAL:              435,000 shares                               $17,575,340         $4,885.94
-----------------------------------------------------------------------------------------------------------------------------------

<F1>  Plus such additional indeterminate number of shares as may be issuable
      pursuant to the anti-dilution provisions of the Plans.

<F2>  Estimated solely for the purpose of determining the amount of the
      registration fee in accordance with Rule 457(c) and 457(h) and based on
      the maximum price at which the options may be exercised as determined by
      the Board of Directors of the Registrant.

<F3>  Represents 33,060 shares issued at $31.00 per share to designated
      individuals pursuant to the agreement between Enterbank Holdings, Inc.,
      Enterprise Bank, and Moneta Group Investment Advisors, Inc., hereafter
      referred to as the "Moneta Agreement", through which Moneta Group is able
      to earn options for referring business to Enterbank Holdings, Inc. or
      subsidiaries thereof.

<F4>  Represents 166,940 shares issuable upon the exercise of stock options
      issued to designated individuals pursuant to the agreement between
      Enterbank Holdings, Inc., Enterprise Bank, and Moneta Group Investment
      Advisors, Inc., hereafter referred to as the "Moneta Agreement", through
      which Moneta Group is able to earn options for referring business to
      Enterbank Holdings, Inc. or subsidiaries thereof.  A price of $42.00 per
      share was used as this is the last known trade to the Company as of the
      filing date of this document.

<F5>  Represents 23,000 shares issued at $30.00 per share pursuant to the
      Enterbank Holdings, Inc. Non-qualified Incentive Stock Option Plan for
      the benefit of the employees of Enterprise Financial Advisors, the
      financial planning and trust divisions of Enterprise Bank.

<F6>  Represents 5,000 shares issued at $31.00 per share pursuant to the
      Enterbank Holdings, Inc. Non-qualified Incentive Stock Option Plan for
      the benefit of the employees of Enterprise Financial Advisors, the
      financial planning and trust divisions of Enterprise Bank.

<F7>  Represents 7,000 shares issuable upon the exercise of stock options
      issued pursuant to the Enterbank Holdings, Inc. Non-qualified Incentive
      Stock Option Plan for the benefit of the employees of Enterprise
      Financial Advisors, the financial planning and trust divisions of
      Enterprise Bank. A price of $42.00 per share was used as this is the
      last known trade to the Company as of the filing date of this document.

<F8>  Represents 200,000 shares issuable upon the exercise of stock options
      issued pursuant to the Enterbank Holdings, Inc. Fourth Incentive Stock
      Option Plan. A price of $42.00 per share was used as this is the last
      known trade to the Company as of the filing date of this document.


INTRODUCTION

This Registration Statement on Form S-8 is filed by Enterbank Holdings, Inc., a Delaware corporation (the "Registrant"), relating to shares of its common stock, par value $.01 per share ("Common Stock"), issuable pursuant to
(1) the agreement between Enterbank Holdings, Inc., Enterprise Bank, and Moneta Group Investment Advisors, Inc., hereafter referred to as the "Moneta Agreement", through which designated employees of Moneta Group are able to earn options for referring business to Enterbank Holdings, Inc. or subsidiaries thereof, (2) the Enterbank Holdings, Inc. Non-Qualified Incentive Stock Option Plan for the benefit of the employees of Enterprise Financial Advisors, the financial planning and trust division of Enterprise Bank, and (3) the Enterbank Holdings, Inc. Fourth Incentive Stock Option Plan.

PART I

INFORMATION REQUIRED IN THE SECTION 10(A) PROSPECTUS

ITEM 1. PLAN INFORMATION.

Information required by Item 1 of Part I of Form S-8 to be contained in the Section 10(a) prospectus is omitted from this Registration Statement in accordance with Rule 428 under the Securities Act of 1933, as amended ("1933 Act"), and the Note to Part I of Form S-8.

ITEM 2. REGISTRATION INFORMATION AND EMPLOYEE PLAN ANNUAL INFORMATION.

Information required by Item 2 of Part I of Form S-8 to be contained in the Section 10(a) prospectus is omitted from this Registration Statement in accordance with Rule 428 under the 1933 Act and the Note to Part I of Form S-8.

I-1

PART II

INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3. INCORPORATION OF DOCUMENTS BY REFERENCE.

The following documents, which previously have been filed by the Registrant with the Securities and Exchange Commission ("Commission"), are incorporated herein by reference and made a part hereof:

(a) The Registrant's Annual Report on Form 10-K for the fiscal year ended December 31, 1998 filed pursuant to
Section 13(a) of the Securities Exchange Act of 1934, as amended ("Exchange Act");

(b) All other reports filed by the Registrant pursuant to
Section 13(a) or 15(d) of the Exchange Act since the end of the fiscal year covered by the Form 10-K;

All documents subsequently filed by the Registrant pursuant to Sections 13(a), 13(c), 14 or 15(d) of the Exchange Act, prior to the filing of a post-effective amendment which indicates that all securities offered hereunder have been sold or which deregisters all securities offered hereunder then remaining unsold, shall be deemed to be incorporated herein by reference and to be a part hereof from the date of filing such documents. Any statement contained herein or in a document all or a portion of which is incorporated or deemed to be incorporated by reference herein shall be deemed to be modified or superseded for purposes of this Registration Statement to the extent that a statement contained herein or in any other subsequently filed document which also is or is deemed to be incorporated by reference herein modifies or supersedes such statement. Any such statement so modified or superseded shall not be deemed, except as so modified or amended, to constitute a part of this Registration Statement.

ITEM 4. DESCRIPTION OF SECURITIES.

The authorized capital stock of the Registrant consists of 3,500,000 shares of common stock, par value $.01 per share ("Common Stock"), of which approximately 2,380,212 shares were outstanding as of July 1, 1999.

Holders of shares of Common Stock are entitled to receive dividends as may from time to time be declared by the Board of Directors of the Registrant out of funds legally available therefore. Holders of Common Stock are entitled to one vote per share on all matters on which the holders of Common Stock are entitled to vote and may cumulate their votes in any election of directors. Holders of Common Stock have no preemptive, conversion, redemption or sinking fund rights. In the event of a liquidation, dissolution or winding up of the Registrant, holders of Common Stock are entitled to share ratably in the assets of the Registrant, if any, remaining after payment of all debts and liabilities of the Registrant. The shares of Common Stock offered by

II-1


the Registrant hereby will be fully paid and non-assessable when issued. There is no established public trading market for the Common Stock.

ITEM 5. INTERESTS OF NAMED EXPERTS AND COUNSEL.

None.

ITEM 6. INDEMNIFICATION OF DIRECTORS AND OFFICERS

The Registrant's By-Laws provide that each person who was or is made a party to, or is involved in, any action, suit, or proceeding by reason of the fact that such person is or was a director or officer of the Registrant will be indemnified and held harmless by the Registrant to the full extent authorized by the Delaware General Corporation Law.

Section 145 of the Delaware General Corporation Law provides as follows:

"INDEMNIFICATION OF OFFICERS, DIRECTORS, EMPLOYEES AND AGENTS;
INSURANCE

"(a) A corporation may indemnify any person who was or is a party or is threatened to be made a party to any threatened, pending or completed action, suit or proceeding, whether civil, criminal, administrative or investigative (other than an action by or in the right of the corporation) by reason of the fact that such person is or was a director, officer, employee or agent of the corporation, or is or was serving at the request of the corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, against expenses (including attorneys' fees), judgments, fines and amounts paid in settlement actually and reasonably incurred by such person in connection with such action, suit or proceeding if such person acted in good faith and in a manner such person reasonably believed to be in or not opposed to the best interests of the corporation, and, with respect to any criminal action or proceeding, had no reasonable cause to believe such person's conduct was unlawful. The termination of any action, suit or proceeding by judgment, order, settlement, conviction, or upon a plea of nolo contendere or its equivalent, shall not, of itself, create a presumption that the person did not act in good faith and in a manner which such person reasonably believed to be in or not opposed to the best interests of the corporation, and with respect to any criminal action or proceeding, had reasonable cause to believe that such person's conduct was unlawful.

"(b) A corporation may indemnify any person who was or is party or is threatened to be made a party to any threatened, pending or completed action or suit by or in the right of the corporation to procure a judgment in its favor by reason of the fact that such person is or was a director, officer, employee or agent of the corporation, or is or was serving at the request of the corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise against expenses (including attorneys' fees) actually and reasonably incurred by such person in connection with the defense or settlement of such action or suit if such person acted in good faith and in a manner such person reasonably believed to be in or not opposed to the best interests of the corporation and except that no indemnification shall be

II-2


made in respect of any claim, issue or matter as to which such person shall have been adjudged to be liable to the corporation unless and only to the extent that the Court of Chancery or the court in which such action or suit was brought shall determine upon application that, despite the adjudication of liability but in view of all the circumstances of the case, such person is fairly and reasonably entitled to indemnity for such expenses which the Court of Chancery or such other court shall deem proper.

"(c) To the extent that a present or former director or officer of a corporation has been successful on the merits or otherwise in defense of any action, suit or proceeding referred to in subsections (a) and
(b) of this section, or in defense of any claim, issue or matter therein, such person shall be indemnified against expenses (including attorneys' fees) actually and reasonably incurred by such person in connection therewith.

"(d) Any indemnification under subsections (a) and (b) of this section (unless ordered by a court) shall be made by the corporation only as authorized in the specific case upon a determination that indemnification of the present or former director, officer, employee or agent is proper in the circumstances because such person has met the applicable standard of conduct set forth in subsections (a) and (b). Such determination shall be made, with respect to a person who is a director or officer at the time of such determination, (1) by a majority vote of the directors who are not parties to such action, suit or proceeding, even though less than a quorum, or (2) by a committee of such directors designated by majority vote of such directors, even though less than a quorum, or (3) if there are no such directors, or if such directors so direct, by independent legal counsel in a written opinion, or (4) by the stockholders.

"(e) Expenses (including attorneys' fees) incurred by an officer or director in defending any civil, criminal, administrative, or investigative action, suit or proceeding may be paid by the corporation in advance of the final disposition of such action, suit or proceeding upon receipt of an undertaking by or on behalf of such director or officer to repay such amount if it shall ultimately be determined that such person is not entitled to be indemnified by the corporation as authorized in this section. Such expenses (including attorneys' fees) incurred by former directors and officers or other employees and agents may be so paid upon such terms and conditions, if any, as the corporation deems appropriate.

"(f) The indemnification and advancement of expenses provided by, or granted pursuant to, the other subsections of this section shall not be deemed exclusive of any other rights to which those seeking indemnification or advancement of expenses may be entitled under any by law, agreement, vote of stockholders or disinterested directors or otherwise, both as to action in such person's official capacity and as to action in another capacity while holding such office.

"(g) A corporation shall have power to purchase and maintain insurance on behalf of any person who is or was a director, officer, employee or agent of the corporation, or is or was serving at the request of the corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise against any liability asserted against such person and incurred by such person in any such capacity, or arising out of

II-3


such person's status as such, whether or not the corporation would have the power to indemnify such person against such liability under this section.

"(h) For purposes of this section, references to "the corporation" shall include, in addition to the resulting corporation, any constituent corporation (including any constituent of a constituent) absorbed in a consolidation or merger which, if its separate existence had continued, would have had power and authority to indemnify its directors, officers, and employees or agents, so that any person who is or was a director, officer, employee or agent of such constituent corporation, or is or was serving at the request of such constituent corporation as a director, officer, employee or agent of another corporation, partnership, joint venture, trust or other enterprise, shall stand in the same position under this section with respect to the resulting or surviving corporation as such person would have with respect to such constituent corporation if its separate existence had continued.

"(i) For purposes of this section, references to "other enterprises" shall include employee benefit plans; references to "fines" shall include any excise taxes assessed on a person with respect to an employee benefit plan; and references to "serving at the request of the corporation" shall include any service as a director, officer, employee or agent of the corporation which imposes duties on, or involves services by, such director, officer, employee, or agent with respect to an employee benefit plan, its participants or beneficiaries; and a person who acted in good faith and in a manner such person reasonably believed to be in the interest of the participants and beneficiaries of an employee benefit plan shall be deemed to have acted in a manner "not opposed to the best interests of the corporation" as referred to in this section.

"(j) The indemnification and advancement of expenses provided by, or granted pursuant to, this section shall, unless otherwise provided when authorized or ratified, continue as to a person who has ceased to be a director, officer, employee or agent and shall inure to the benefit of the heirs, executors and administrators of a person.

"(k) The Court of Chancery is hereby vested with exclusive jurisdiction to hear and determine all actions for advancement of expenses or indemnification brought under this section or under any bylaw, agreement, vote of stockholders or disinterested directors, or otherwise the Court of Chancery may summarily determine a corporation's obligation to advance expenses (including attorneys' fees)."

Pursuant to the Registrant's Certificate of Incorporation, no director of the Registrant shall be personally liable to the Registrant or its stockholders for monetary damages for any breach of fiduciary duty as a director. The Certificate of Incorporation further provides, however, that a director shall be liable to the extent provided by applicable law (i) for any breach

II-4


of the director's duty of loyalty to the Registrant or its stockholders; (ii) for acts or omissions not in good faith or which involve intentional misconduct or a knowing violation of law; (iii) pursuant to Section 174 of the Delaware General Corporation Law; or (iv) for any transaction from which such director derived an improper personal benefit. No amendment or repeal of this provision in the Certificate of Incorporation may adversely affect any right or protection of any director of the Registrant existing at the time of such amendment or repeal for or with respect to any acts or omissions of such director occurring prior to such amendment or repeal.

The Registrant may purchase and maintain, and currently does so maintain, insurance on behalf of its officers and directors against liability asserted against any of them and incurred by them in such capacity, or arising out of their status as such.

ITEM 7. EXEMPTION FROM REGISTRATION CLAIMED.

Not applicable.

ITEM 8. EXHIBITS.

Exhibit No.                         Description
-----------                         -----------
4                                   Certificate of Incorporation of Enterbank Holdings, Inc. incorporated
                                    herein by reference from Exhibit 3.1 to the Form S-1 dated December 19,
                                    1996 (File No. 333-14737).

4.1                                 Bylaws of Enterbank Holdings, Inc. incorporated herein by reference from
                                    Exhibit 3.2 to the Form S-1 dated December 19, 1996 (File No. 333-14737).

            <F*>4.2                             Amendment to the Certificate of Incorporation as approved by the
                                    shareholders of the Company on April 28, 1999.  The Company subsequently
                                    notified the Delaware Secretary of State of the Amendment.

            <F*>5                               Opinion of Armstrong Teasdale LLP as to the legality of the securities
                                    being registered.

10.1                                Agreement between Enterbank Holdings, Inc., Enterprise Bank, and Moneta
                                    Group Investment Advisors, Inc. incorporated herein by reference from
                                    Exhibit 10 to the Form 10-Q for the period ended September 30, 1997
                                    (File No. 000-24131).

10.2                                Enterbank Holdings, Inc. Non-Qualified Plan for the benefit of the
                                    employees of Enterprise Financial Advisors

                        II-5

                                    incorporated herein by reference to the 1998 Proxy Statement on Form 14-A
                                    (File No. 000-24131).

            <F*>10.3                            Enterbank Holdings, Inc. Fourth Incentive Stock Option Plan

            <F*>23.1                            Consent of Armstrong Teasdale, LLP (included in Exhibit 5 hereto).

            <F*>24                              Power of Attorney (reference is made to page II-8 hereof).

            <F*>Filed herewith.

ITEM 9. UNDERTAKINGS.

(a) The undersigned Registrant hereby undertakes:

1. To file, during any period in which offers or sales are being made, a post-effective amendment to this registration statement:

(i) to include any prospectus required by Section 10(a)(3) of the Securities Act of 1933, as amended (the "1933 Act");

(ii) to reflect in the prospectus any facts or event arising after the effective date of this registration statement (or the most recent post- effective amendment thereof) which, individually or in the aggregate, represent a fundamental change in the information set forth in this registration statement; and

(iii) to include any material information with respect to the plan of distribution not previously disclosed in this registration statement or any material change to such information in this registration statement; provided, however, that paragraphs (a)(1)(i) and (a)(1)(ii) of this section do not apply if this registration statement is on Form S-3, Form S-8 or Form F-3, and the information required to be included in a post-effective amendment by those paragraphs is contained in periodic reports filed with or furnished to the Commission pursuant to Section 13 or Section 15(d) of the Exchange Act that are incorporated by reference in this registration statement.

2. That, for the purpose of determining any liability under the 1933 Act, each such post-effective amendment shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

II-6


3. To remove from registration by means of a post-effective amendment any of the securities being registered which remain unsold at the termination of the offering.

(b) The undersigned Registrant hereby undertakes that, for purposes of determining any liability under the 1933 Act, each filing of the Registrant's annual report pursuant to Section 13(a) or Section 15(d) of the Exchange Act (and, where applicable, each filing of an employee benefit plan's annual report pursuant to Section 15(d) of the Exchange Act) that is incorporated by reference in the registration statement shall be deemed to be a new registration statement relating to the securities offered therein, and the offering of such securities at that time shall be deemed to be the initial bona fide offering thereof.

(c) Insofar as indemnification for liabilities arising under the 1933 Act may be permitted to directors, officers and controlling persons of the Registrant pursuant to the foregoing provisions, or otherwise, the Registrant has been advised that in the opinion of the Commission such indemnification is against public policy as expressed in the 1933 Act and is, therefore, unenforceable. In the event that a claim for indemnification against such liabilities (other than the payment by the Registrant of expenses incurred or paid by a director, officer or controlling person of the Registrant in the successful defense of any action, suit or proceeding) is asserted by such director, officer or controlling person in connection with the securities being registered, the Registrant will, unless in the opinion of its counsel the matter has been settled by controlling precedent, submit to a court of appropriate jurisdiction the question whether such indemnification by it is against public policy as expressed in the 1933 Act and will be governed by the final adjudication of such issue.

II-7


EXHIBIT 4.2

AMENDMENT TO THE ARTICLES OF INCORPORATION
FOR ENTERBANK HOLDINGS, INC.

BE IT RESOLVED, that the CERTIFICATE OF INCORPORATION of Enterbank Holdings, Inc. is hereby amended so that ARTICLE FOUR thereof shall read in its entirety as follows:

"ARTICLE FOUR

The aggregate number of shares which the corporation shall have authority to issue shall be three million, five hundred thousand (3,500,000) shares of common stock, par value $.01 each.

The distinguishing preferences, qualifications, limitations, restrictions and special or relative rights in respect to the common stock as follows:

In all elections of Directors of the Corporation, each common shareholder shall have the right to cast as many votes as shall equal (x) the number of shares held by him or her, and multiplied by (y) the number of Directors to be elected, and he or she may cast all such votes for a single Director or may distribute them among the number of directors to be elected, or any two (2) or more of them, as such shareholder may deem fit."


EXHIBIT 5

7/1/99

Enterbank Holdings, Inc.
150 North Meramec
St. Louis, Missouri 63105

RE: REGISTRATION ON FORM S-8 OF 435,000 SHARES OF COMMON STOCK

Ladies and Gentlemen:

In connection with the registration with the Securities and Exchange Commission of 435,000 shares of common stock, $0.01 par value per share (the "Securities"), of Enterbank Holdings, Inc. (the "Company"), you have requested that we furnish you with our opinion as to the legality of the issuance of the Securities in connection with 200,000 of such Securities to be issued pursuant to the Company's agreement with Enterprise Bank and Moneta Group, Inc. dated October 31, 1997 (the "Agreement"), 35,000 of such Securities to be issued pursuant to the Company's Non-Qualified Incentive Stock Option Plan (the "Non-Qualified Plan") and 200,000 of such Securities to be issued pursuant to the Company's Fourth Incentive Stock Option Plan (the "Incentive Plan").

As counsel to the Company, we have participated in the preparation of the Registration Statement on Form S-8 under the Securities Act of 1933, as amended (the "Registration Statement") with respect to the Securities. We have examined and are familiar with the Company's Certificate of Incorporation, Bylaws, records of corporate proceedings, the Registration Statement, the Agreement, the Non-Qualified Plan, the Incentive Plan and such other documents and records as we have deemed necessary for purposes of this opinion.

Based on the foregoing, we are of the opinion that the Securities have been duly and validly authorized and will, when issued as contemplated in the Agreement, the Non-Qualified Plan and the Incentive Plan, as applicable, be legally issued, fully paid and non-assessable.

We consent to the use of this opinion as an exhibit to the Registration Statement.

Sincerely,

                                                /s/ ARMSTRONG TEASDALE LLP
                                                -------------------------------
                                                ARMSTRONG TEASDALE LLP

July 1, 1999


OPTION GRANT AGREEMENT

ENTERBANK HOLDINGS, INC. (the "Company"), a Delaware chartered bank holding company, and --------------------("Employee") make and enter into this Option Grant Agreement (the "Agreement") effective as of -------------------.

WHEREAS, Optionee is a valuable and trusted employee of the Company, and the Company considers it desirable and in its best interests that Employee be given an inducement to acquire a proprietary interest in the Company to provide an added incentive to advance the interests of the Company to provide an added incentive to advance the interests of the Company; and

WHEREAS, the board of directors of the Company (the "Board") has adopted a fourth incentive stock option plan (the "Plan") on April 28, 1999 and the stockholders approved the Plan on April 28, 1999; and

WHEREAS, pursuant to the provisions of the Plan, the Board has decided to grant Employee an option to purchase shares of the Company's $.01 par value, voting common stock (the "Common Stock").

NOW, THEREFORE, in consideration of the forgoing recitals and the following promises, the Employee and the Company agree as follows:

1.

Pursuant to this Agreement, the Company grants to Employee the right, privilege, and option to purchase --------- shares of its Common Stock at the purchase price of ------- per share (the "Option").

2.

The Employee may exercise the Option at any time, and from time to time, in whole or in part, until the termination of the Option as provided in Section 4 of the Agreement, subject to the following:

(a) [20%] of the shares of Common Stock which may be purchased pursuant to this Option may be purchased on or after -------------- (one year from grant date);

(b) [20%] of the shares of Common Stock which may be purchased pursuant to this Option may be purchased on or after -------------- (two years from grant date);

(c) [20%] of the shares of Common Stock which may be purchased pursuant to this Option may be purchased on or after -------------- (three years from grant date);


(d) [20%] of the shares of Common Stock which may be purchased pursuant to this Option may be purchased on or after -------------- (four years from grant date);

(e) [20%] of the shares of Common Stock which may be purchased pursuant to this Option may be purchased on or after -------------- (five years from grant date);

In the event of termination of employment for any reason other than death, the shares of Common Stock which may be purchased pursuant to an Option shall be limited to the number of shares which are fully vested and available for purchase as of the date and time of termination of employment. In the event of the death of an Optionee, all shares of Common Stock, which may be purchased pursuant to an Option held by the Optionee, shall be deemed fully vested and available for purchase.

In the event of a "Change of Control" of the Company, as defined in the Plan, all shares of Common Stock which may be purchased pursuant to an Option shall be deemed fully vested and available for purchase.

The aggregate fair market value (determined at the time the option is granted) of the Stock with respect to which ISOs are exercisable for the first time by an individual during any calendar year (under this Plan or any other ISO plan of Company) may exceed $100,000.00. The options representing such excess aggregate fair market value shall not be Incentive ISOs pursuant to the Internal Revenue Code Section 422 (d). Provided, however, that such non-qualified options shall be subject to all other previsions of the plan. With respect to such non-qualified options, the Company shall denote on the stock certificates issued upon exercise of such options that such certificates were issued as a result of non-qualifed options. If an Optionee receives options under this agreement, a part of which will be qualified under Section 422 of the Code and part of which are not qualified, such Optionee shall notify the Company whether qualified or non-qualified options are being exercised. Absent such notification, the Company shall treat such exercise as an exercise of qualified options to the extent available.

3.

3.1 The Option shall be exercised by written notice from Employee to Company, directed to the attention of the Board.

3.2 Contemporaneous with the delivery to Employee of the appropriate evidence of the shares of Common Stock being issued to Employee (which shall occur as soon as practicable following receipt of notice of exercise by Company), Employee shall deliver to Company cash or a cashier's check payable to the order of the Company in payment of the option price for the number of shares specified and paid for, and Employee and Company shall execute the Stock Restriction Agreement described hereinafter.

2

3.3 If at any time the Board shall determine in its discretion, that the listing, registration, or qualification of the shares covered by this Option upon any securities exchange or under any state or federal law, or that the consent or approval of any governmental regulatory body, is necessary or desirable as a condition of, or in connection with, the issue or purchase of shares hereunder, no shares shall be issued pursuant to this Option unless and until such listing registration, qualification, consent, or approval shall have been effected or obtained free of any conditions not acceptable to the Board.

4.

4.1 To the extent not previously exercised, the Option shall terminate upon the first to occur of the following:

(a) If Employee's employment is terminated for any reason, then the date three months after the date of such termination; or

(b) --------------- (ten years from grant date).

4.2 The transfer of Employee from the employ of the Company to a Subsidiary or vice versa, or from one Subsidiary to another shall not be considered an interruption or termination of employment for purposes of this Agreement.

5.

In the event that additional shares of Common Stock are issued pursuant to a stock split or a stock dividend, the number of shares of Common Stock, subject to Option shall be increased proportionally and the price per share shall be decreased proportionally with no change in the total purchase price of the shares subject to Option. In the event that the shares of Common Stock from time to time issued and outstanding are reduced by a combination of shares, the number of shares of Common Stock subject to Option shall be reduced proportionally and the price per share shall be increased proportionally with no change in the total price of the shares subject to Option. No fractional shares shall be issued, and any fractional shares resulting from the computations pursuant hereto shall be eliminated from the Option. No adjustment shall be made for dividends (other than stock dividends) or the issuance to stockholders of rights to subscribe for additional Common Stock or other securities.

6.

This Option is non-transferable and is exercisable only by Employee or the Employee's personal representative. Employee shall have no rights as a stockholder with respect to the optioned shares of Common Stock until payment of the option price of shares for which the Option has been exercised, execution of the Stock Restriction Agreement

3

described hereinafter, and delivery to Employee of the appropriate evidence of the shares as herein provided.

7.

Subject to the provisions of Section 6 of this Agreement, this Agreement shall be binding upon and inure to the benefit of the Company and the Employee and their respective successors, assigns, heirs, executors, administrators and personal representatives.

8.

This Agreement is not a contract of employment of any kind whatsoever between Employee and any present of future employer of Employee.

9.

The certificate representing the Option shall be marked with the following legend endorsement:

"The alienation and transfer of this option certificate and the option to acquire stock of Enterbank Holdings, Inc. represented hereby is subject to an Option Grant Agreement between Enterbank Holdings, Inc. and the registered holder hereof, a copy of which is in the possession of the Secretary of Enterbank Holdings, Inc."

10.

Any notice required hereunder shall be in writing, and shall be given by mailing the notice by certified mail, postage prepaid, return receipt requested, addressed to the party to whom given, at the address of such party stated below, or at such other address as such party may previously have designated by notice hereunder. Notices shall be deemed given as of the date mailed.

11.

This Agreement constitutes the entire contract and understanding between the Employee and the Company with respect to the Option.

12.

As used herein, "Subsidiary" means any corporation which would constitute a subsidiary corporation of Company as defined in Subsection 425(f) of the Internal Revenue Code of 1986, as amended, if, in applying such definition, the term "Company" is substituted for "employer corporation" wherever it appears.

4

13.

This Agreement may not be modified or amended except by an instrument in writing executed by the Employee and the Company.

14.

This Agreement is being entered into in and shall be construed in accordance with the laws of the State of Missouri.

15.

This Agreement may be executed in several counterparts, each of which shall be deemed an original.

IN WITNESS WHEREOF, the Employee and the Company have executed this Agreement as of the date first above written.

Employee:


Employee Name

Employee Address

Company:

ENTERBANK HOLDINGS, INC.

By:---------------------------------
President

150 North Meramec
Clayton, Missouri 63105

5

ENTERBANK HOLDINGS, INC.
FOURTH INCENTIVE STOCK OPTION PLAN

1.

This Fourth Incentive Stock Option Plan for ENTERBANK HOLDINGS, INC. is intended to advance the interests of the Organization by providing Key Employees who have substantial responsibility for the direction and management of the Company and its Subsidiaries with additional incentive to promote the success of the Organization's business, and by encouraging the Key Employees to remain in the employ of the Organization. The above aims will be accomplished through the granting of certain stock options. It is intended that options issued under the Plan qualify as ISOs, and the provisions of the Plan shall be interpreted in accordance with this intention. Provided, however, that such intention shall not be construed to negate any options granted under the plan that are not treated as incentive stock options by virtue of the Internal Revenue Code 422 (d).

2.

The items defined below shall have the following meanings throughout the Plan:

2.1 "Bank" means ENTERPRISE BANK, a Missouri financial institution.

2.2 "Board" means the Board of Directors of Company.

2.3 "Code" means the Internal Revenue Code of 1986, as amended.

2.4 "Company" means ENTERBANK HOLDINGS, INC., a Delaware corporation.

2.5 "ISOs" means stock options which qualify as incentive stock options under Section 422 of the Code. Such term shall also include those options that would be considered incentive stock options but for Internal Revenue Code Section 422 (d).

2.6 "Key Employees" means officers, directors, executives and supervisory personnel, as well as other employees of the Company or the Subsidiaries, who have substantial responsibility for the direction and management of the Organization.

2.7 "Organization" means the Company, the Bank and the Subsidiaries.

2.8 "Optionee" means the person to whom an option is granted.

2.9 "Plan" means the Fourth Incentive Stock Option Plan as defined by the provisions hereof.

6

2.10 "Stock" means the voting common stock of Company.

2.11 "Subsidiaries" means any subsidiary bank or corporation owned or controlled by the Company, the Bank, or one of the Subsidiaries.

2.12 "Ten Percent Shareholder" means any individual who at the time an option is granted owns directly or indirectly stock possessing more than 10% of the total combined voting power of all classes of stock of the Company, taking into account the provisions of Section 424 (d) of the Code.

2.13 "Change of Control" means: (i) a merger or consolidation of the Company with or into any other entity, unless after such event at least a majority of the voting power of the surviving or resulting entity is beneficially owned by persons who beneficially own a majority of the voting power of the Company immediately prior to such event or (ii) a sale of all or substantially all the assets of the Company (except to a Subsidiary of the Company), or (iii) the dissolution of the Company, or (iv) a change in the identity of a majority of the members of the Company's Board of Directors within any twelve-month period, which change or changes are not recommended by the incumbent directors determined immediately prior to any such change or changes, or (iv) any tender or exchange offer or other transaction in which the holders of the Company's common stock become entitled to receive or may elect to receive either cash or securities of an entity other than the Company, but not a stock split or reverse stock split of, or stock dividend on, the Company's common stock as a class, or (v) any change or changes in the beneficial ownership of the securities of the Company within any one-year period, including any such change or changes effected in whole or in part by the redemption of outstanding securities or the issuance of new securities, as a result of which any "person," as such term is used in Sections 3(a)(9), 13(d) and 14(d) of the Securities and Exchange Act of 1934, as amended (the "Exchange Act") (other than the Company, any trustees or other fiduciary holding securities under any employee benefit plan of the Company, or any company beneficially owned by the stockholders of th Company in substantially the same proportions as their ownership of stock of the Company), becomes the beneficial owner of securities of the Company representing 50% or more of the combined voting power of the Company's then outstanding securities. For purposes of this paragraph, beneficial ownership shall be as defined in Rule 13d-3 under the Exchange Act.

3.

The Board shall administer the Plan. Subject to the provisions of the Plan, the Board shall have authority, in its sole and absolute discretion;
(a) to determine the employees of the Organization (from among the class of employees eligible under Section 4 to receive options under the Plan) to whom options shall be granted; (b) to determine the time or times at which options shall be granted; (c) to determine the option price of the shares subject to each option, which price shall not be less than the minimum specified in Section 6.1; (d) to determine (subject to Section 6.2) the duration

7

of the exercise period for each option subject to the vesting limitations of the Plan; (e) to determine the form of options granted hereunder; (f) to determine the exact provisions of any ISO issued hereunder so long as such provisions are not inconsistent with Section 422 of the Code; and (g) to interpret the Plan and to prescribe, amend, and rescind rules and regulations relating to it. For purposes of acting with respect to the Plan, a majority of the members of the Board shall constitute a quorum and the acts of a majority of the members present at any meeting at which a quorum is present, or acts approved in writing by a majority of the members of the Board shall be deemed the acts of the Board.

4.

4.1 Options shall be granted only to Key Employees.

4.2 The aggregate fair market value (determined at the time the option is granted) of the Stock with respect to which ISOs are exercisable for the first time by an individual during any calendar year (under this Plan or any other ISO plan of Company) may exceed $100,000.00. The options representing such excess aggregate fair market value shall not be Incentive ISOs pursuant to the Internal Revenue Code Section 422 (d). Provided, however, that such non-qualified options shall be subject to all other previsions of the plan. With respect to such non-qualified options, the Company shall denote on the stock certificates issued upon exercise of such options that such certificates were issued as a result of non-qualifed options. If an Optionee receives options under this agreement, a part of which will be qualified under Section 422 of the Code and part of which are not qualified, such Optionee shall notify the Company whether qualified or non-qualified options are being exercised. Absent such notification, the Company shall treat such exercise as an exercise of qualified options to the extent available.

4.3 Options granted under the Plan may be exercised in whole or in part throughout the duration of the exercise period for each option set by the Board subject to the following vesting requirements:

(a) Twenty percent of the shares of Common Stock which may be purchased pursuant to an Option, shall be available for purchase on or after one (1) year from the date of grant;

(b) Twenty percent of the shares of Common Stock which may be purchased pursuant to an Option, shall be available for purchase on or after two (2) years from the date of grant;

(c) Twenty percent of the shares of Common Stock which may be purchased pursuant to an Option, shall be available for purchase on or after three (3) years from the date of grant;

8

(d) Twenty percent of the shares of Common Stock which may be purchase pursuant to an Option, shall be available for purchase on or after four (4) years from the date of grant; and

(e) Twenty percent of the shares of Common Stock, which may be purchased pursuant to an Option, shall be available for purchase on or after five (5) years from the date of grant.

In the event of termination of employment for any reason other than death, the shares of Common Stock which may be purchased pursuant to an Option shall be limited to number of shares which are fully vested and available for purchase under this Section 4.3 as of the dated and time of termination of employment. In the event of the death of an Optionee, all shares of Common Stock, which may be purchased pursuant to an Option held by the Optionee, shall be deemed fully vested and available for purchase, subject to the limitation set forth in Section 4.2 of the Plan.

4.4 In the event of a "Change of Control" of the Company, as defined in Section 4.13 of the Plan, all shares of common Stock which may be purchased pursuant to an Option shall be deemed fully vested and available for purchase, subject to the limitation set forth in Section 4.2 of the Plan.

5.

5.1 The maximum number of shares of Stock which may be issued pursuant to ISOs granted hereunder (subject to adjustment as provided in Section 5.3 hereof) shall be 200,000 shares and, to the extent allowed by law, said number of shares will be granted at any time and from time to time under the Plan (subject to the provisions of Section10). These shares may be in whole or in part, as the Board shall from time to time determine, authorized but unissued shares or unauthorized shares which may be authorized pursuant to powers of attorney granted by shareholders of the company. Any shares subject to an option under the Plan, which option for any reason expires or is terminated unexercised as to such shares, may again be subjected to an option under the Plan.

5.2 In the event that additional shares of Stock are issued pursuant to a stock split or a stock dividend, the number of shares of Stock then covered by each outstanding option granted hereunder shall be increased proportionally and the per share price of such shares shall be decreased proportionally with no change in the total purchase price of the shares then so covered. The number of shares of Stock reserved for the purpose of the Plan shall also be increased proportionally. In the event that the shares of Stock of the Company from time to time issued and outstanding are reduced by a combination of shares, the number of shares of Stock then covered by each outstanding option granted hereunder shall be reduced proportionally and the per share price shall be increased proportionally with no change in the total price of the shares then so covered. The number of shares of Stock reserved for the purposes of the Plan shall also be reduced proportionally. No fractional shares shall be issued, and any

9

fractional shares resulting from the computations pursuant to this Section 5.2 shall be eliminated from the respective option. No adjustment shall be made for dividends (other than stock dividends) or the issuance to stockholders of rights to subscribe for additional common stock or other securities.

6.

6.1 The option price for each share of Stock covered by an ISO shall be an amount not less than 100% (or, in the case of an ISO granted to a Ten Percent Shareholder, not less than 110%) of the fair market value of the Stock on the date the option is granted.

6.2 All ISOs issued under the Plan shall be for such period as the Board shall determine, but for not more than ten (10) years (or, if the Optionee is a Ten Percent Shareholder, five (5) years) from the date of grant thereof.

6.3 The period of the ISO, once it is granted, may be reduced only as provided for in Section 7 in connection with the termination of employment of the Optionee.

6.4 Except as provided in Section 7 hereof, no ISO may be exercised unless the Optionee is at the time of such exercise in the employ of the Organization and shall have been continuously so employed since the grant of the option.

6.5 Each option granted under the Plan shall be nontransferable and shall be exercisable only by the Optionee to whom the option is granted. No option granted under the Plan or any of the rights and privileges thereby conferred shall be transferred, assigned, pledged, or hypothecated in any way (whether by operation of law or otherwise), and no such option, right, or privilege shall be subject to execution, attachment, or similar process. Upon any attempt to so transfer, assign, pledge, hypothecate, or otherwise dispose of the option or of any right or privilege conferred thereby, contrary to the provisions hereof, or upon the levy of any attachment or similar process upon such option, right or privilege, the option such rights and privileges shall immediately become null and void.

7.

7.1 In the event of an Optionee's termination of employment for any reason, such Optionee or the Optionee's guardian or personal representative may exercise any Options theretofore granted, which have vested and are not then expired, within three (3) months after such termination of employment; provided, however, in the case of termination of employment due to permanent disability, the three month period of exercise shall be extended to one year.

10

7.2 The transfer of a Key Employee from the Company and any Subsidiary to the company or any Subsidiary shall not be considered an interruption or termination of employment for purposes of this Agreement.

8.

8.1 The exercise of any ISO shall also be contingent upon receipt by the Company of cash or cashier's check to its order, in an amount equal to the full option price of the shares being purchased.

8.2 No Optionee or his or her legal representative, heir, or legatee, as the case may be, will be, or will be deemed to be, a holder of any share subject to an option unless and until appropriate documents evidencing such shares are issued under the provisions of the Plan. Adjustment shall be made, however, for dividends for which the record date is after the date the option is exercised but prior to the date such evidence of such shares is issued.

8.3 Each option shall be subject to the condition that if at any time the Board shall determine, in its discretion, that the listing, registration, or qualification of the shares covered thereby upon any securities exchange or under any state or federal law or that the consent or approval of any governmental regulatory body is necessary or desirable as a condition of, or in connection with, the issue or purchase of shares under such option, such option, such shares will not be issued unless and until such listing, registration, qualification, consent, or approval shall have been effected or obtained free of any conditions not acceptable to the Board.

8.4 Neither the Plan nor any option agreement covering options issued under the Plan is to be construed as a contract of employment of any kind whatsoever between a Key Employee and any present or future employer of Key Employee.

8.5 Exercise of an option shall result in a decrease in the number of shares of Stock, which thereafter may be available under the Plan by the number of shares as to which the option is exercised.

9.

No option shall be granted pursuant to the Plan after ten (10) years from the date the Plan is adopted by the Board, or the date the Plan is approved by the majority of the outstanding shares of each class of Company stock, whichever is earlier.

11

10.

The Board may at any time terminate the plan, and at any time and from time to time modify and amend the Plan in any respect; provided, however, that no such amendment shall: (a) increase (except in accordance with Section 5.2) the maximum number of shares for which options may be granted under the Plan either in the aggregate or to any individual Optionee; or (b) reduce (except in accordance with Section 5.2) the minimum option prices which may be established under the Plan; or (c) extend the maximum periods provided for in Sections 6.2 and 10, respectively, during which options may be exercised or granted; or (d) change the provisions relating to the determination of employees to whom options shall be granted and the number of shares to be covered by such options; or (e) change the provisions relating to adjustments to be made upon changes in capitalization. The termination or any modification or amendment of the Plan shall not, without the consent of an Optionee, affect his or her rights under an option theretofore granted to such Optionee.

11.

The Plan shall not affect the provisions of any nonqualified stock options granted to any employee of the Organization under any other plan relating to non-qualified stock options; nor shall it affect any of the rights of any employee or the Organization to whom such a non-qualified stock option was granted.

12.

This Plan shall become effective on the later of the date of its adoption by the Board or its approval by the vote of the holders of a majority of the outstanding shares of each class of the Company's stock. This Plan shall not become effective unless such shareholder approval shall be obtained within twelve (12) months before or after the adoption of the Plan by the Board.

12

SIGNATURES - EXHIBIT 24

THE REGISTRANT. Pursuant to the requirements of the Securities Act of 1933, the Registrant certifies that it has reasonable grounds to believe that it meets all of the requirements for filing on Form S-8 and has duly caused this Registration Statement to be signed on its behalf by the undersigned, thereunto duly authorized, in the City of Clayton, State of Missouri, on May 19, 1999.

ENTERBANK HOLDINGS, INC.                  ENTERBANK HOLDINGS, INC.

    /s/ James C. Wagner                       /s/ Fred H. Eller
By: --------------------------------      By: --------------------------------
       James C. Wagner                           Fred H. Eller
       Chief Financial Officer                   Chief Executive Officer

POWER OF ATTORNEY

We, the undersigned officers and directors of Enterbank Holdings, Inc., hereby severally constitute and appoint Fred H. Eller and James C. Wagner and each of them, our true and lawful attorneys-in-fact and agents, with full power of substitution and resubstitution, for each of us in our name, place, and stead, in any and all capacities, to sign Enterbank Holdings, Inc.'s Registration Statement on Form S-8, and any other Registration Statement relating to the same offering, and any and all amendments thereto (including post-effective amendments), and to file the same, with all exhibits thereto, and other documents in connection therewith, with the Securities and Exchange Commission, and hereby grant to such attorneys-in-fact and agents, and each of them, full power and authority to do and perform each and every act and thing requisite and necessary to be done, as fully to all intents and purposes as each of us might or could do in person, hereby ratifying and confirming all that said attorneys-in-fact and agents or any of them or his or their substitute or substitutes may lawfully do or cause to be done by virtue hereof.

Pursuant to the requirements of the Securities Act of 1933, this Registration Statement has been signed by the following persons in the capacities indicated and on the dates indicated.

SIGNATURES                                TITLE                                           DATE
----------                                -----                                           ----

/s/ Fred H. Eller
--------------------------                President, Chief Executive Officer              May 19, 1999
Fred H. Eller                             and Director


/s/ Ronald E. Henges
--------------------------                Chairman of the Board                           May 19, 1999
Ronald E. Henges                          of Directors


                                    II-8

SIGNATURES                                TITLE                                           DATE
----------                                -----                                           ----

/s/ Kevin C. Eichner
--------------------------
Kevin C. Eichner


/s/ Randall D. Humphreys
--------------------------                Director                                        May 19, 1999
Randall D. Humphreys


/s/ Paul R. Cahn
--------------------------                Director                                        May 19, 1999
Paul R. Cahn


/s/ William B. Moskoff
--------------------------                Director                                        May 19, 1999
William B. Moskoff


/s/ Birch M. Mullins
--------------------------                Director                                        May 19, 1999
Birch M. Mullins


/s/ Robert E. Saur
--------------------------                Director                                        May 19, 1999
Robert E. Saur


/s/ Paul L. Vogel
--------------------------                Director                                        May 19, 1999
Paul L. Vogel


/s/ James A. Williams
--------------------------                Director                                        May 19, 1999
James A. Williams


/s/ Henry D. Warshaw
--------------------------                Director                                        May 19, 1999
Henry D. Warshaw


/s/ James L. Wilhite
--------------------------                Director                                        May 19, 1999
James L. Wilhite


/s/ Ted C. Wetterau
--------------------------                Director                                        May 19, 1999
Ted C. Wetterau

II-9