UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM 8-K

                                 CURRENT REPORT

                     Pursuant to Section 13 or 15(d) of the
                         Securities Exchange Act of 1934

                        Date of Report: December 31, 2004
                        (Date of earliest event reported)

                          21ST CENTURY HOLDING COMPANY
             (Exact name of registrant as specified in its charter)

            Florida                     0-2500111               65-0248866
-------------------------------   -----------------------    -------------------
(State or other jurisdiction of   (Commission File Number)   (I.R.S. Employer 
         incorporation)                                      Identification No.)

       3661 West Oakland Park Blvd., Suite 300         
                Lauderdale Lakes, FL                       33311
      ----------------------------------------           ----------
      (Address of principal executive offices)           (Zip Code)

       Registrant's telephone number, including area code: (954) 581-9993
                                                           --------------

                                 NOT APPLICABLE
          -------------------------------------------------------------
         (Former Name or Former Address, if Changed Since Last Report)
 
Check  the  appropriate  box  below  if the  Form  8-K  filing  is  intended  to
simultaneously  satisfy the filing obligation of the registrant under any of the
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|_|   Written communications pursuant to Rule 425 under the Securities Act (17
      CFR 230.425)

|_|   Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR
      240.14a-12)

|_|   Pre-commencement communications pursuant to Rule 14d-2(b) under the
      Exchange Act (17 CFR 240.14d-2(b))

|_|   Pre-commencement communications pursuant to Rule 13e-4(c) under the
      Exchange Act (17 CFR 240.13e-4(c))



Item 1.01 Entry into a Material Definitive Agreement.

      21st  Century  Holding  Company (the  "Company")  has entered into a Stock
Purchase and Redemption  Agreement (the "Agreement")  dated January 3, 2005 with
Express Tax  Service,  Inc.  ("ETS"),  Robert J. Kluba  ("Kluba")  and Robert H.
Taylor ("Taylor,"  together with Kluba, the "Buyers").  The Company currently is
the  beneficial and record owner of 80% of the issued and  outstanding  stock of
ETS, which in turn owns 100% of the issued and outstanding  stock of Express Tax
Franchise Corporation ("ETFC").  Kluba is currently the President and a director
of ETS and ETFC, and owns the remaining 20% of the issued and outstanding  stock
of ETS.

      Pursuant  to the  Agreement,  the Company has agreed to sell to the Buyers
all of its  common  stock  in ETS for a total  purchase  price of  $660,000.  In
addition to the cash  payment of $660,000  for the shares of ETS to the Company,
the Company  shall also receive at closing a cash payment equal to $1,200,000 in
exchange for the Company's agreement not to compete with the current business of
ETS and ETFC for five years following the closing.

      In  connection  with the  Agreement,  the  Company  agreed to  extend  the
expiration dates for the 75,000  outstanding stock options previously granted to
Kluba and the 30,000  outstanding  stock options  previously  granted to Kluba's
wife, such that 80% of such stock options shall expire, if not exercised, on the
first  anniversary  date of the  closing  and the  remaining  20% of such  stock
options shall expire on the second anniversary date of the closing,  except that
none of these options shall be exercisable  for the six-month  period  following
the closing.

      In connection  with the sale of assets  described in Item 8.01 below,  the
Company also agreed to accelerate the vesting of 103,650  options held by the 50
employees  whose  employment with the Sellers  (defined  below)  terminated as a
result of the closing of the transaction.

Item 8.01 Other Events.

      As  previously  reported on the  Company's  Form 8-K filed on December 27,
2004,  the Company and its wholly owned  subsidiaries,  Federated  Agency Group,
Inc.  ("Federated"),  Fed USA, Inc. ("Fed USA"), and Assurance  Managing General
Agents,  Inc.  ("Assurance,"  and  together  with  Federated  and Fed  USA,  the
"Sellers"),  entered into an Asset  Purchase  Agreement  dated December 21, 2004
(the "Asset Purchase  Agreement") to sell certain assets related to the Sellers'
non-standard  automobile insurance agency business located in Florida to Fed USA
Retail, Inc. and Fed USA Franchising, Inc. (together, the "Buyers"). The sale of
the assets closed on December 31, 2004.

      The  Sellers  received  at closing a cash  payment of  $7,000,000  and are
entitled to receive an additional  payment of up to  $2,500,000  based on 10% of
the "Gross Net Written  Premiums" (as defined in the Asset  Purchase  Agreement)
for the 12-month period following the closing date written through the Company's
two insurance company  subsidiaries or through any insurance company  affiliated
with the Buyers  that  exceed  $15,000,000  in the  aggregate  and are less than
$40,000,000  in the  aggregate.  This  additional  payment,  if any,  is due and
payable 45 days after the end of the 12-month period following the closing.

      The Buyers assumed specified  liabilities related to the assets purchased.
The   Buyers  are   affiliates   of   Affirmative   Insurance   Holdings,   Inc.
("Affirmative"),   an  insurance  holding  company  based  in  Addison,   Texas.
Affirmative  has  guaranteed the Buyers'  obligations  to make the  post-closing
payment described above.



                                   SIGNATURES

      Pursuant to the  requirements of the Securities  Exchange Act of 1934, the
registrant  has duly  caused  this  report  to be  signed  on its  behalf by the
undersigned hereunto duly authorized.

                                    21ST CENTURY HOLDING COMPANY

Date:  January 6, 2005              By:  /s/ Richard A. Widdicombe
                                        --------------------------
                                    Name:    Richard A. Widdicombe
                                    Title:   Chief Executive Officer
                                             (Principal Executive Officer)

Date:  January 6, 2005              By:   /s/ J. Gordon Jennings III
                                        ----------------------------
                                    Name:     J. Gordon Jennings III
                                    Title:    Chief Financial Officer
                                    (Principal Accounting and Financial Officer)