As filed with the Securities and Exchange Commission on May 3, 2004
                                                           File No. 333-
--------------------------------------------------------------------------------
                                  UNITED STATES
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549
                                ----------------

                                    FORM S-3
             REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933
                                ----------------

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

            FLORIDA                                      65-0248866
----------------------------------          ------------------------------------
(State or other jurisdiction of             (I.R.S. Employer Identification No.)
 incorporation or organization)

           4161 N.W. 5TH STREET, PLANTATION, FL 33317, (954) 581-9993
           ----------------------------------------------------------
    (Address, including zip code, and telephone number, including area code,
                  of registrant's principal executive offices)

                                ----------------

                              RICHARD A. WIDDICOMBE
                             CHIEF EXECUTIVE OFFICER
                          21ST CENTURY HOLDING COMPANY
                              4161 N.W. 5TH STREET
                              PLANTATION, FL 33317
                                 (954) 581-9993
            (Name, address, including zip code, and telephone number,
                   including area code, of agent for service)

                                   Copies to:

                            A. JEFFRY ROBINSON, P.A.
                                BROAD AND CASSEL
                          201 SOUTH BISCAYNE BOULEVARD
                            MIAMI CENTER, SUITE 3000
                              MIAMI, FLORIDA 33131
                            TELEPHONE: (305) 373-9400
                           TELECOPIER: (305) 373-9443

                                ----------------

        Approximate date of commencement of proposed sale to the public:
   As soon as practicable after this Registration Statement becomes effective.

If the only securities being registered on this form are being offered pursuant
to dividend or interest reinvestment plans, please check the following box. [ ]

If any of the securities being registered on this form are to be offered on a
delayed or continuous basis pursuant to Rule 415 under the Securities Act of
1933, other than securities offered only in connection with dividend or interest
reinvestment plans, check the following box. [X]

If this form is filed to register additional securities for an offering pursuant
to Rule 462(b) under the Securities Act, please check the following box and list
the Securities Act registration statement number of the earlier effective
registration statement for the same offering. [ ]

If this form is a post-effective amendment filed pursuant to Rule 462(c) under
the Securities Act, check the following box and list the Securities Act
registration statement number of the earlier effective registration statement
for the same offering. [ ]

If delivery of the prospectus is expected to be made pursuant to Rule 434,
please check the following box. [ ]




                         CALCULATION OF REGISTRATION FEE
--------------------------------------------------------------------------------------------------------------------
                                                                                 PROPOSED MAXIMUM
TITLE OF EACH CLASS                    AMOUNT TO BE       PROPOSED MAXIMUM     (AGGREGATE OFFERING      AMOUNT OF
OF SECURITIES TO BE REGISTERED        REGISTERED (1)   OFFERING PRICE PER UNIT        PRICE         REGISTRATION FEE
--------------------------------------------------------------------------------------------------------------------
                                                                                        
Common Stock, $.01 par value          35,819 shares          $20.25                $725,335              $91.90
--------------------------------------------------------------------------------------------------------------------


(1) Estimated solely for the purpose of calculating the registration fee in
    accordance with Rule 457 under the Securities Act.

THE REGISTRANT HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE OR DATES
AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT SHALL FILE
A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION STATEMENT
SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTION 8(A) OF THE
SECURITIES ACT OF 1933 OR UNTIL THIS REGISTRATION STATEMENT SHALL BECOME
EFFECTIVE ON SUCH DATE AS THE SECURITIES AND EXCHANGE COMMISSION, ACTING
PURSUANT TO SAID SECTION 8(A), MAY DETERMINE.




THE INFORMATION IN THIS PROSPECTUS IS NOT COMPLETE AND MAY BE CHANGED. WE MAY
NOT SELL THESE SECURITIES UNTIL THE REGISTRATION STATEMENT FILED WITH THE
SECURITIES AND EXCHANGE COMMISSION IS EFFECTIVE. THIS PROSPECTUS IS NOT AN OFFER
TO SELL THE SECURITIES AND IT IS NOT SOLICITING AN OFFER TO BUY THESE SECURITIES
IN ANY STATE IN WHICH THE OFFER OR SALE IS NOT PERMITTED.

                       SUBJECT TO COMPLETION, May 3, 2004

                                   PROSPECTUS

                          35,819 SHARES OF COMMON STOCK

                          21ST CENTURY HOLDING COMPANY

         This prospectus covers 35,819 shares of our common stock issued by us
as payment of principal and interest due on our 6% Senior Subordinated Notes due
July 31, 2006. We will not receive any proceeds from the sale of the common
stock. We will pay our out-of-pocket expenses, legal and accounting fees, and
the other expenses of registering these shares for resale.

         The shareholders named in this prospectus may offer and sell these
shares at any time using a variety of different methods. The actual number of
shares sold and the prices at which the shares are sold will depend upon the
market prices at the time of those sales; therefore, we have not included in
this prospectus information about the price to the public of the shares or the
proceeds to the selling shareholders.

         Our common stock is traded on the Nasdaq National Market under the
symbol "TCHC." On April 30, 2004, the last reported sale price of the common
stock on the Nasdaq National Market was $20.44 per share.

         The shares of common stock offered hereby involve a high degree of risk
and should be considered only by such persons capable of bearing the economic
risk of such investment. You should carefully consider the "Risks of Investing
in Our Shares" section beginning on page 3 of this prospectus.

         NEITHER THE SEC NOR ANY STATE SECURITIES COMMISSION HAS APPROVED OR
DISAPPROVED OF THESE SECURITIES OR PASSED UPON THE ADEQUACY OR ACCURACY OF THIS
PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENSE.

                 The date of this prospectus is May ____, 2004.



                                TABLE OF CONTENTS
                                -----------------


                                                                                                                 PAGE
                                                                                                                 ----
                                                                                                                
PROSPECTUS SUMMARY..................................................................................................1

RISKS OF INVESTING IN OUR SHARES....................................................................................3

         Our revenues and operating performance may fluctuate with business cycles in the
                  property and casualty insurance industry..........................................................3

         If we are unable to continue our growth because our capital must be used to pay
                  greater than anticipated claims, our financial results may suffer.................................3

         The maximum credit commitment under our revolving loan was reduced by our lender and
                  could be subject to further review and reduction, which would adversely
                  affect our available working capital..............................................................3

          We may not obtain the necessary regulatory approvals to expand the types of insurance
                  products we offer or the states in which we operate...............................................4

         If our ratings are downgraded or withdrawn, we may be unable to write or renew
                  desirable insurance policies or obtain adequate reinsurance, which would
                  limit or halt our growth and harm our business....................................................4

         Although we follow the industry practice of reinsuring a portion of our risks, our
                  costs of obtaining reinsurance have increased and we may not be able to
                  successfully alleviate risk through reinsurance arrangements......................................4

         Our investment portfolio may suffer reduced returns or losses, which would
                  significantly reduce our earnings.................................................................5

         Our loss reserves may be inadequate to cover our actual liability for losses, causing
                  our results of operations to be adversely affected................................................5

         Legislation may be enacted that would limit our ability to increase our premiums or
                  cancel, reduce or non-renew our existing policies, which could reduce our
                  revenues or increase our claims losses............................................................6

         We are subject to significant government regulation, which can limit our growth and
                  increase our expenses, thereby reducing our earnings..............................................6

         We rely on agents, most of whom are independent agents or franchisees, to write our
                  insurance policies, and if we are not able to attract and retain independent
                  agents and franchisees, our revenues would be negatively affected.................................6

         Our primary insurance product, nonstandard automobile insurance, historically has a
                  higher frequency of claims than standard automobile insurance, thereby
                  increasing our potential for loss exposure beyond what we would be likely to
                  experience if we offered only standard automobile insurance.......................................7

         Florida's personal injury protection insurance statute contains provisions that favor
                  claimants, causing us to experience a higher frequency of claims than might
                  otherwise be the case if we operated only outside of Florida......................................7

         Our business strategy is to avoid competition in our automobile insurance products
                  based on price to the extent possible. This strategy, however, may result in
                  the loss of business in the short term............................................................7

         With operations concentrated in Florida, we could be adversely affected by
                  unpredictable catastrophic events such as hurricanes and tropical storms..........................8

         Our president and chief executive officer are key to the strategic direction of our
                  company. If we were to lose the services of either of them, our business
                  could be harmed...................................................................................8

         The trading of our warrants may negatively affect the trading prices of our common
                  stock if investors purchase and exercise the warrants to facilitate other
                  trading strategies, such as short selling.........................................................8

         Our largest shareholders control approximately 29% of the voting power of our
                  outstanding common stock, which could discourage potential acquirors and
                  prevent changes in management.....................................................................9

         We have authorized but unissued preferred stock, which could affect rights of holders
                  of common stock...................................................................................9

         Our articles of incorporation and bylaws and Florida law may discourage takeover
                  attempts and may result in entrenchment of management.............................................9

         As a holding company, we depend on the earnings of our subsidiaries and their ability
                  to pay dividends to the holding company as the primary source of our income......................10

NOTE REGARDING FORWARD-LOOKING STATEMENTS..........................................................................10


                                       i


                                TABLE OF CONTENTS
                                -----------------
                                   (continued)


                                                                                                                 PAGE
                                                                                                                 ----
                                                                                                                
USE OF PROCEEDS....................................................................................................11

SELLING SHAREHOLDERS...............................................................................................11

HOW THE SHARES MAY BE DISTRIBUTED..................................................................................12

LEGAL MATTERS......................................................................................................13

EXPERTS............................................................................................................13

WHERE YOU CAN FIND MORE INFORMATION................................................................................13

INCORPORATION OF CERTAIN INFORMATION BY REFERENCE..................................................................14

INDEMNIFICATION OF DIRECTORS AND OFFICERS..........................................................................15


                              ABOUT THIS PROSPECTUS

         You should rely only on the information contained in this prospectus.
No dealer, salesperson or other person is authorized to give any information
that is not contained in this prospectus. This prospectus is not an offer to
sell nor is it seeking an offer to buy these shares in any jurisdiction where
the offer or sale is not permitted. The information contained in this prospectus
is correct only as of the date of this prospectus, regardless of the time of the
delivery of this prospectus or any sale of these shares.

                                       ii


                               PROSPECTUS SUMMARY

         This is only a summary and does not contain all of the information that
may be important to you. You should read the more detailed information contained
in this prospectus and all other information, including the financial
information and statements with notes, as discussed in the "Where You Can Find
More Information" section of this prospectus.

OVERVIEW
--------

         We are a vertically integrated insurance holding company, which,
through our subsidiaries, controls substantially all aspects of the insurance
underwriting, distribution and claims process. We underwrite personal automobile
insurance, general liability insurance, flood insurance, homeowners' insurance,
and mobile home property and casualty insurance in the State of Florida through
our wholly owned subsidiaries, Federated National Insurance Company and American
Vehicle Insurance Company. American Vehicle underwrites general liability
insurance in Louisiana as an admitted carrier and in Georgia as a foreign
insurer. Federated National underwrites homeowners insurance in Louisiana as an
admitted carrier. During the year ended December 31, 2003, 67%, 23%, 7% and 2%
of the policies we underwrote were for personal automobile insurance,
homeowners' insurance, general liability insurance and mobile home property and
casualty insurance, respectively. We internally process claims made by our own
and third-party insureds through our wholly owned claims adjusting company,
Superior Adjusting, Inc. We also offer premium financing to our own insureds
through our wholly owned subsidiary, Federated Premium Finance, Inc.

         We market and distribute our own and third-party insurers' products and
our other services primarily in Central and South Florida, through a network of
23 agencies owned by Federated Agency Group, Inc., a wholly owned subsidiary, 44
franchised agencies, and approximately 125 independent agents. Through our
wholly owned subsidiary, FedUSA, Inc., we franchise agencies under the FedUSA
name. As of December 31, 2003, franchises were granted for 44 FedUSA agencies,
of which 38 were operating. We intend to focus our future expansion efforts for
our agency network on franchised agencies.

         Assurance Managing General Agents, Inc., a wholly owned subsidiary,
acts as Federated National's and American Vehicle's exclusive managing general
agent. Assurance MGA currently provides all underwriting policy administration,
marketing, accounting and financial services to Federated National, American
Vehicle and our agencies, and participates in the negotiation of reinsurance
contracts.

         We offer electronic tax filing services through Express Tax Service,
Inc., an 80%-owned subsidiary, as well as franchise opportunities for these
services. As of December 31, 2003, there were 231 franchises granted in 18
states. Revenue is generated through franchise sales, collection of royalties on
tax preparation fees, incentives from business partners as well as fees from the
preparation of income tax returns and income tax refund anticipation loans. In
addition, Express Tax offers tax preparation services through more than 500
licensees nationwide, acting as sales representatives.

                                       1


         We believe that we can be distinguished from our competitors because we
generate revenue from substantially all aspects of the insurance underwriting,
distribution and claims process. We provide quality service to both our agents
and insureds by utilizing an integrated computer system, which links our
insurance and service entities. Our computer and software systems allow for
automated premium quotation, policy issuance, billing, payment and claims
processing and enables us to continuously monitor substantially all aspects of
our business. Using these systems, our agents can access a customer's driving
record, quote a premium, offer premium financing and, if requested, generate a
policy on-site. We believe that these systems have facilitated our ability to
market and underwrite insurance products on a cost-efficient basis, allow our
owned and franchised agencies to be a "one stop" shop for insurance, tax
preparation and other services, and will enhance our ability to expand in
Florida and to other states.

         Our primary products are nonstandard and standard personal automobile
insurance. Of the total auto premiums we received in 2003, 97.2% were from
nonstandard insurance policies and 2.8% were from standard insurance policies.
The former is principally provided to insureds who are unable to obtain
preferred or standard insurance coverage because of their payment history,
driving record, age, vehicle type or other factors, including market conditions
for preferred or standard risks. The latter is principally provided to insureds
who present an average risk profile in terms of payment history, driving record,
vehicle and other factors. We believe that industry-wide underwriting standards
for standard insurance coverage have become more restrictive, thereby requiring
more drivers to seek coverage in the nonstandard automobile insurance market. We
believe that these factors have contributed to an increase in the size of the
nonstandard personal automobile insurance market.

         We currently underwrite and sell insurance in Florida, Louisiana and
Georgia; however, we intend to expand to other selected states and we have
applied to obtain licenses to underwrite and sell personal automobile insurance
and general liability insurance in Alabama. We will select additional states for
expansion based on a number of criteria, including the size of the personal
automobile insurance market, statewide loss results, competition and the
regulatory climate. Our ability to expand into other states will be subject to
receiving prior regulatory approval of each state. Certain states impose
operating requirements upon licensee applicants, which may impose burdens on our
ability to obtain a license to conduct insurance business in those other states.
There can be no assurance that we will be able to obtain the required licenses,
and the failure to do so would limit our ability to expand geographically.

         Our executive offices are located at 4161 N.W. 5th Street, Plantation,
Florida and our telephone number is (954) 581-9993.

                                       2

                        RISKS OF INVESTING IN OUR SHARES

         You should carefully consider the following risks, in addition to the
other information presented in this prospectus or incorporated by reference into
this prospectus, before making an investment decision. If any of these risks or
uncertainties actually occur, our business, results of operations, financial
condition, or prospects could be substantially harmed, which would adversely
affect your investment.

RISKS RELATED TO OUR BUSINESS
-----------------------------

OUR REVENUES AND OPERATING PERFORMANCE MAY FLUCTUATE WITH BUSINESS CYCLES IN THE
PROPERTY AND CASUALTY INSURANCE INDUSTRY.

         Historically, the financial performance of the property and casualty
insurance industry has tended to fluctuate in cyclical patterns characterized by
periods of significant competition in pricing and underwriting terms and
conditions, which is known as a "soft" insurance market, followed by periods of
lessened competition and increasing premium rates, which is known as a "hard"
insurance market. Although an individual insurance company's financial
performance is dependent on its own specific business characteristics, the
profitability of most property and casualty insurance companies tends to follow
this cyclical market pattern, with profitability generally increasing in hard
markets and decreasing in soft markets. At present, we are experiencing a "hard"
market in our automobile and property sectors. We cannot predict, however, how
long these market conditions will persist. If we were to experience a "soft"
market, increased price competition would likely cause us to have to reduce our
premiums in order to maintain our market share, which would result in a decrease
in our revenues.

IF WE ARE UNABLE TO CONTINUE OUR GROWTH BECAUSE OUR CAPITAL MUST BE USED TO PAY
GREATER THAN ANTICIPATED CLAIMS, OUR FINANCIAL RESULTS MAY SUFFER.

         We have grown rapidly over the last few years. Our future growth will
depend on our ability to expand the types of insurance products we offer and the
geographic markets in which we do business. We believe that our company is
sufficiently capitalized to operate our business as it now exists and as we
currently plan to expand it. Our existing sources of funds include our revolving
loan from Flatiron Funding Company LLC, sales of our securities such as our July
2003 private placement of $7,500,000 of our senior subordinated notes, and our
earnings from operations and investments. Unexpected catastrophic events in our
market areas could result in greater claims losses than anticipated, which could
require us to limit or halt our growth while we redeploy our capital to pay
these unanticipated claims.

THE MAXIMUM CREDIT COMMITMENT UNDER OUR REVOLVING LOAN WAS REDUCED BY OUR LENDER
AND COULD BE SUBJECT TO FURTHER REVIEW AND REDUCTION, WHICH WOULD ADVERSELY
AFFECT OUR AVAILABLE WORKING CAPITAL.

         In September 2002, the maximum credit commitment under our revolving
loan agreement was reduced to $4.0 million from $7.0 million due to the A.M.
Best ratings of third-party insurance carriers for which we were financing
policies at that time. Simultaneously, we ceased financing policies from
third-party insurance carriers altogether. In 2003, we began again to finance


                                       3


policies from third-party insurers, but limited to policies generated from a
small number of independent agents whose customer base and operational history
meet our strict criteria for creditworthiness. We have also changed other
aspects of our business so that the higher credit commitment is currently
unnecessary. Our lender, however, could determine to further reduce our
available credit. If that occurs and we are not able to obtain working capital
from other sources, then we would have to restrict our growth and, possibly, our
operations.

WE MAY NOT OBTAIN THE NECESSARY REGULATORY APPROVALS TO EXPAND THE TYPES OF
INSURANCE PRODUCTS WE OFFER OR THE STATES IN WHICH WE OPERATE.

         We currently have applications pending in Alabama to underwrite and
sell personal automobile and general liability insurance. The insurance
regulators in this state may request additional information, add conditions to
the license that we find unacceptable, or deny our application. This would delay
or prevent us from operating in that state. If we want to operate in any
additional states, we must file similar applications for licenses, which we may
not be successful in obtaining.

IF OUR RATINGS ARE DOWNGRADED OR WITHDRAWN, WE MAY BE UNABLE TO WRITE OR RENEW
DESIRABLE INSURANCE POLICIES OR OBTAIN ADEQUATE REINSURANCE, WHICH WOULD LIMIT
OR HALT OUR GROWTH AND HARM OUR BUSINESS.

         Third-party rating agencies assess and rate the ability of insurers to
pay their claims. These financial strength ratings are used by the insurance
industry to assess the financial strength and quality of insurers. These ratings
are based on criteria established by the rating agencies and reflect evaluations
of each insurer's profitability, debt and cash levels, customer base, adequacy
and soundness of reinsurance, quality and estimated market value of assets,
adequacy of reserves, and management. Ratings are based upon factors of concern
to agents, reinsurers and policyholders and are not directed toward the
protection of investors, such as purchasers of our common stock.

         In 2003, A.M. Best Company assigned Federated National a B rating
("Fair," which is the seventh of 14 rating categories) and American Vehicle a B+
rating ("Very Good," which is the sixth of 14 rating categories). Federated
National and American Vehicle are rated "A" ("Unsurpassed," which is first of
six ratings) by Demotech, Inc. If our financial condition deteriorates, we may
not maintain our ratings. A downgrade or withdrawal of our ratings could
severely limit or prevent us from writing or renewing desirable insurance
policies or from obtaining adequate reinsurance.

ALTHOUGH WE FOLLOW THE INDUSTRY PRACTICE OF REINSURING A PORTION OF OUR RISKS,
OUR COSTS OF OBTAINING REINSURANCE HAVE INCREASED AND WE MAY NOT BE ABLE TO
SUCCESSFULLY ALLEVIATE RISK THROUGH REINSURANCE ARRANGEMENTS.

         We follow the insurance industry practice of reinsuring a portion of
our risks and paying for that protection based upon premiums received on all
policies subject to this reinsurance. Our business depends on our ability to
transfer or "cede" significant amounts of risk insured by us. Reinsurance makes
the assuming reinsurer liable to the extent of the risk ceded. Both Federated
National and American Vehicle currently cede approximately 40% of their premiums
from automobile insurance policies to Transatlantic Reinsurance Company.
Federated National also obtains reinsurance for its property insurance policies
on the private market in Bermuda and London and through the Florida Hurricane
Catastrophe Fund. The Florida Hurricane Catastrophe Fund reinsures Federated


                                       4


National for liabilities resulting from a storm causing damage totaling $5.5
million to $42.3 million in the aggregate, which we believe constitutes an event
expected to occur no more often than once in a period of 100 years.

         Because we currently obtain a material portion of our reinsurance from
one reinsurer, we are also subject to credit risk with respect to that
reinsurer, as the ceding of risk does not relieve us of liability to our
insureds regarding the portion of the risk that has been reinsured, if the
reinsurer fails to pay for any reason. The insolvency of our primary reinsurer
or any of our other current or future reinsurers, or their inability otherwise
to pay claims, would increase the claims that we must pay, thereby significantly
harming our results of operations. In addition, prevailing market conditions
have limited the availability and increased the cost of reinsurance, which has
increased our costs and reduced our profitability.

OUR INVESTMENT PORTFOLIO MAY SUFFER REDUCED RETURNS OR LOSSES, WHICH WOULD
SIGNIFICANTLY REDUCE OUR EARNINGS.

         As do other insurance companies, we depend on income from our
investment portfolio for a substantial portion of our earnings. A significant
decline in investment yields in our investment portfolio caused by fluctuations
in interest rates or volatility in the stock market, or a default by issuers of
securities that we own, could adversely affect the value of our investment
portfolio and the returns that we earn on our portfolio, thereby substantially
harming our financial condition and results of operations. During the time that
normally elapses between the receipt of insurance premiums and any payment of
insurance claims, we invest the funds received, together with our other
available capital, primarily in fixed-maturity investments and equity
securities, in order to generate investment income. In 2003, net investment
income totaled $1.6 million, or 19 % of our total net income of $8.4 million.

         We experienced net realized investment losses of $1,369,961 for 2002
and $2,911,658 for 2001. The net realized losses experienced in 2001 were
primarily a function of the widely publicized declines in the industrial common
stock valuations. As a result of the declines in the equity markets in 2001, we
acquired securities in the more conservative and highly rated industrial bond
markets in late 2001 and the first half of 2002. During 2002, we incurred a
$2,000,000 decline in value of our investment in WorldCom, Inc. bonds. This
write down is reflected in the $1,369,961 loss incurred in 2002. We have been
experiencing a declining interest rate environment during the past three years.
The effect on our bond portfolio of this declining interest rate environment has
been to decrease our yields to maturity and the interest income generated
accordingly.

OUR LOSS RESERVES MAY BE INADEQUATE TO COVER OUR ACTUAL LIABILITY FOR LOSSES,
CAUSING OUR RESULTS OF OPERATIONS TO BE ADVERSELY AFFECTED.

         We maintain reserves to cover our estimated ultimate liabilities for
loss and loss adjustment expenses. These reserves are estimates based on
historical data and statistical projections of what we believe the settlement
and administration of claims will cost based on facts and circumstances then
known to us. Actual losses and loss adjustment expenses, however, may vary
significantly from our estimates. For example, after we compared our reserve
levels to our actual claims for the prior years, we increased our liability for
loss and loss adjustment expenses by $1,234,047 for 2003, $90,874 for 2002, and
$2,568,476 for 2001. These increases reflected primarily our loss experience
under our personal automobile policies. Because of the uncertainties that
surround estimated loss reserves, we cannot be certain that our reserves will be


                                       5


adequate to cover our actual losses. If our reserves for unpaid losses and loss
adjustment expenses are less than actual losses and loss adjustment expenses, we
will be required to increase our reserves with a corresponding reduction in our
net income in the period in which the deficiency is identified. Future loss
experience substantially in excess of our reserves for unpaid losses and loss
adjustment expenses could substantially harm our results of operations and
financial condition.

LEGISLATION MAY BE ENACTED THAT WOULD LIMIT OUR ABILITY TO INCREASE OUR PREMIUMS
OR CANCEL, REDUCE OR NON-RENEW OUR EXISTING POLICIES, WHICH COULD REDUCE OUR
REVENUES OR INCREASE OUR CLAIMS LOSSES.

         Legislation has been proposed from time to time in Florida, which is
where our operations are now primarily located, that would limit our ability to
increase our premiums or that would restrict our ability to cancel, reduce or
non-renew existing policies. If one or more of these proposals are enacted in
Florida, or in any other state in which we conduct significant business
operations, our results of operations could be materially adversely affected if
we are not able to increase our premiums to offset higher expenses or if we are
not able to cancel, reduce or non-renew existing policies where our claims
experience has been unacceptably high.

WE ARE SUBJECT TO SIGNIFICANT GOVERNMENT REGULATION, WHICH CAN LIMIT OUR GROWTH
AND INCREASE OUR EXPENSES, THEREBY REDUCING OUR EARNINGS.

         We are subject to laws and regulations in Florida, our state of
domicile, and Georgia, and will be subject to the laws of any other state in
which we conduct business in the future. These laws and regulations cover all
aspects of our business and are generally designed to protect the interests of
insurance policyholders. For example, these laws and regulations relate to
licensing requirements, authorized lines of business, capital surplus
requirements, allowable rates and forms, investment parameters, underwriting
limitations, restrictions on transactions with affiliates, dividend limitations,
changes in control, market conduct, and limitations on premium financing service
charges. The cost to monitor and comply with these laws and regulations adds
significantly to our cost of doing business. Further, if we do not comply with
the laws and regulations applicable to us, we may be subject to sanctions or
monetary penalties by the applicable insurance regulator.

WE RELY ON AGENTS, MOST OF WHOM ARE INDEPENDENT AGENTS OR FRANCHISEES, TO WRITE
OUR INSURANCE POLICIES, AND IF WE ARE NOT ABLE TO ATTRACT AND RETAIN INDEPENDENT
AGENTS AND FRANCHISEES, OUR REVENUES WOULD BE NEGATIVELY AFFECTED.

         We currently market and distribute Federated National's, American
Vehicle's and third-party insurers' products and our other services through a
network of 23 agencies that we own, 44 agencies that we franchise to others, and
approximately 125 independent agents. Approximately 51% of our insurance
products are sold through agents employed by us and franchised agents and
approximately 49% of our products are sold through independent agents. Many of
our competitors also rely on independent agents. As a result, we must compete
with other insurers for independent agents' business and with other franchisors
of insurance agencies for franchisees. Our competitors may offer a greater
variety of insurance products, lower premiums for insurance coverage, or higher
commissions to their agents. If our products, pricing and commissions do not
remain competitive, we may find it more difficult to attract business from


                                       6


independent agents and to attract franchisees for our agencies to sell our
products. A material reduction in the amount of our products that independent
agents sell would negatively affect our revenues.

OUR PRIMARY INSURANCE PRODUCT, NONSTANDARD AUTOMOBILE INSURANCE, HISTORICALLY
HAS A HIGHER FREQUENCY OF CLAIMS THAN STANDARD AUTOMOBILE INSURANCE, THEREBY
INCREASING OUR POTENTIAL FOR LOSS EXPOSURE BEYOND WHAT WE WOULD BE LIKELY TO
EXPERIENCE IF WE OFFERED ONLY STANDARD AUTOMOBILE INSURANCE.

         Nonstandard automobile insurance, which is our primary product, is
provided to insureds who are unable to obtain preferred or standard insurance
coverage because of their payment histories, driving records, age, vehicle
types, or prior claims histories. This type of automobile insurance historically
has a higher frequency of claims than does preferred or standard automobile
insurance policies, although the average dollar amount of the claims is usually
smaller under nonstandard insurance policies. As a result, we are exposed to the
possibility of increased loss exposure and higher claims experience than would
be the case if we offered only standard automobile insurance.

FLORIDA'S PERSONAL INJURY PROTECTION INSURANCE STATUTE CONTAINS PROVISIONS THAT
FAVOR CLAIMANTS, CAUSING US TO EXPERIENCE A HIGHER FREQUENCY OF CLAIMS THAN
MIGHT OTHERWISE BE THE CASE IF WE OPERATED ONLY OUTSIDE OF FLORIDA.

         Florida's personal injury protection insurance statute limits an
insurer's ability to deny benefits for medical treatment that is unrelated to
the accident, that is unnecessary, or that is fraudulent. In addition, the
statute allows claimants to obtain awards for attorney's fees. Although this
statute has been amended several times in recent years, primarily to address
concerns over fraud, the Florida legislature has been only marginally successful
in implementing effective mechanisms that allow insurers to combat fraud and
other abuses. We believe that this statute contributes to a higher frequency of
claims under nonstandard automobile insurance policies in Florida, as compared
to claims under standard automobile insurance policies in Florida and
nonstandard and standard automobile insurance polices in other states. Although
we believe that we have successfully offset these higher costs with premium
increases, because of competition, we may not be able to do so with as much
success in the future.

OUR BUSINESS STRATEGY IS TO AVOID COMPETITION IN OUR AUTOMOBILE INSURANCE
PRODUCTS BASED ON PRICE TO THE EXTENT POSSIBLE. THIS STRATEGY, HOWEVER, MAY
RESULT IN THE LOSS OF BUSINESS IN THE SHORT TERM.

         Although our pricing of our automobile insurance products is inevitably
influenced to some degree by that of our competitors, we believe that it is
generally not in our best interest to compete solely on price, choosing instead
to compete on the basis of underwriting criteria, our distribution network, and
our superior service to our agents and insureds. With respect to automobile
insurance in Florida, we compete with more than 100 companies, which underwrite
personal automobile insurance. Comparable companies which compete with us in the
personal automobile insurance market include U.S. Security Insurance Company,
United Automobile Insurance Company, Direct General Insurance Company and
Security National Insurance Company, as well as major insurers such as


                                       7


Progressive Casualty Insurance Company. Comparable companies which compete with
us in the homeowners' market include Florida Family Insurance Company, Florida
Select Insurance Company, Atlantic Preferred Insurance Company and Vanguard
Insurance Company. Comparable companies which compete with us in the general
liability insurance market include Century Surety Insurance Company, Atlantic
Casualty Insurance Company, Colony Insurance Company and Burlington/First
Financial Insurance Companies. Competition could have a material adverse effect
on our business, results of operations and financial condition. If we do not
meet the prices offered by our competitors, we may lose business in the short
term, which could also result in reduced revenues.

WITH OPERATIONS CONCENTRATED IN FLORIDA, WE COULD BE ADVERSELY AFFECTED BY
UNPREDICTABLE CATASTROPHIC EVENTS SUCH AS HURRICANES AND TROPICAL STORMS.

         We write insurance policies that cover automobile owners, homeowners
and business owners for losses that result from catastrophes. Catastrophic
losses can be caused by hurricanes, tropical storms, tornadoes, wind, hail,
fires, riots and explosions, and their incidence and severity are inherently
unpredictable. The extent of losses from a catastrophe is a function of two
factors: the total amount of the insurance company's exposure in the area
affected by the event and the severity of the event. Our policyholders are
currently concentrated in South and Central Florida, which is especially subject
to adverse weather conditions such as hurricanes and tropical storms. Although
we have not experienced significant claims as a result of a recent hurricane or
other weather events, the occurrence of a catastrophe in South Florida could
substantially harm us by causing claims to exceed our anticipated reserve for
losses.

OUR PRESIDENT AND CHIEF EXECUTIVE OFFICER ARE KEY TO THE STRATEGIC DIRECTION OF
OUR COMPANY. IF WE WERE TO LOSE THE SERVICES OF EITHER OF THEM, OUR BUSINESS
COULD BE HARMED.

         We depend, and will continue to depend, on the services of one of our
founders and principal shareholders, Edward J. Lawson, who is also our president
and chairman of the board, as well as Richard Widdicombe, who is our chief
executive officer. We have entered into an employment agreement with each of
them and we maintain $3 million and $1 million in keyman life insurance on the
lives of Mr. Lawson and Mr. Widdicombe, respectively. Nevertheless, because of
Mr. Lawson's and Mr. Widdicombe's role and involvement in developing and
implementing our current business strategy, the loss of either of their services
could substantially harm our business.

RISKS RELATED TO AN INVESTMENT IN OUR SHARES

THE TRADING OF OUR WARRANTS MAY NEGATIVELY AFFECT THE TRADING PRICES OF OUR
COMMON STOCK IF INVESTORS PURCHASE AND EXERCISE THE WARRANTS TO FACILITATE OTHER
TRADING STRATEGIES, SUCH AS SHORT SELLING.

         The 816,000 warrants we issued in our July 2003 private offering are
currently approved for trading on the Nasdaq National Market under the symbol of
"TCHCW." Each of the warrants entitles the holder to purchase one-half of one
share of our common stock at an exercise price per share of $19.1153. Investors
may purchase and exercise warrants to facilitate trading strategies such as
short selling, which involves the sale of securities not yet owned by the
seller. In a short sale, the seller must either purchase or borrow the security
in order to complete the sale. If shares of our common stock received upon the
exercise of warrants are used to complete short sales, this may have the effect
of reducing the trading price of our common stock.

                                       8


OUR LARGEST SHAREHOLDERS CONTROL APPROXIMATELY 29% OF THE VOTING POWER OF OUR
OUTSTANDING COMMON STOCK, WHICH COULD DISCOURAGE POTENTIAL ACQUIRORS AND PREVENT
CHANGES IN MANAGEMENT.

         Edward J. Lawson and Michele V. Lawson beneficially own approximately
29% of our outstanding common stock. As our largest shareholders, and our only
shareholders owning more than 10% of our common stock, the Lawsons have
significant influence over the outcome of any shareholder vote. This voting
power may discourage takeover attempts, changes in our officers and directors or
other changes in our corporate governance that other shareholders may desire.

WE HAVE AUTHORIZED BUT UNISSUED PREFERRED STOCK, WHICH COULD AFFECT RIGHTS OF
HOLDERS OF COMMON STOCK.

         Our articles of incorporation authorize the issuance of preferred stock
with designations, rights and preferences determined from time to time by our
board of directors. Accordingly, our board of directors is empowered, without
shareholder approval, to issue preferred stock with dividends, liquidation,
conversion, voting or other rights that could adversely affect the voting power
or other rights of the holders of common stock. In addition, the preferred stock
could be issued as a method of discouraging a takeover attempt. Although we do
not intend to issue any preferred stock at this time, we may do so in the
future.

OUR ARTICLES OF INCORPORATION AND BYLAWS AND FLORIDA LAW MAY DISCOURAGE TAKEOVER
ATTEMPTS AND MAY RESULT IN ENTRENCHMENT OF MANAGEMENT.

         Our articles of incorporation and bylaws contain provisions that may
discourage takeover attempts and may result in entrenchment of management.

         o        Our board of directors is elected in classes, with only two or
                  three of the directors elected each year. As a result,
                  shareholders would not be able to change the membership of the
                  board in its entirety in any one year. Shareholders would also
                  be unable to bring about, through the election of a new board
                  of directors, changes in our officers.

         o        Our articles of incorporation prohibit shareholders from
                  acting by written consent, meaning that shareholders will be
                  required to conduct a meeting in order to vote on any
                  proposals or take any action.

         o        Our bylaws require at least 60 days' notice if a shareholder
                  desires to submit a proposal for a shareholder vote or to
                  nominate a person for election to our board of directors.

         In addition, Florida has enacted legislation that may deter or
frustrate takeovers of Florida corporations, such as our company.

         o        The Florida Control Share Act provides that shares acquired in
                  a "control share acquisition" will not have voting rights
                  unless the voting rights are approved by a majority of the
                  corporation's disinterested shareholders. A "control share


                                       9


                  acquisition" is an acquisition, in whatever form, of voting
                  power in any of the following ranges: (a) at least 20% but
                  less than 33-1/3% of all voting power, (b) at least 33-1/3%
                  but less than a majority of all voting power; or (c) a
                  majority or more of all voting power.

         o        The Florida Affiliated Transactions Act requires supermajority
                  approval by disinterested shareholders of certain specified
                  transactions between a public corporation and holders of more
                  than 10% of the outstanding voting shares of the corporation
                  (or their affiliates).

AS A HOLDING COMPANY, WE DEPEND ON THE EARNINGS OF OUR SUBSIDIARIES AND THEIR
ABILITY TO PAY DIVIDENDS TO THE HOLDING COMPANY AS THE PRIMARY SOURCE OF OUR
INCOME.

         We are an insurance holding company whose primary assets are the stock
of our subsidiaries. Our operations, and our ability to service our debt, are
limited by the earnings of our subsidiaries and their payment of their earnings
to us in the form of management fees, dividends, loans, advances or the
reimbursement of expenses. These payments can be made only when our subsidiaries
have adequate earnings. In addition, these payments made to us by our insurance
subsidiaries are restricted by Florida law governing the insurance industry.
Generally, Florida law limits the dividends payable by insurance companies under
complicated formulas based on the subsidiary's available capital and earnings.
Under these formulas, Federated National would be able to pay approximately
$200,000 in dividends in 2004 and American Vehicle would be able to pay
approximately $70,000 in dividends in 2004. Florida law does authorize the
Florida Office of Insurance Regulation to approve dividends that exceed the
formula amounts.

         No dividends were declared or paid by our subsidiaries in 2003, 2002 or
2001. Whether our subsidiaries will be able to pay dividends in 2004 depends on
the results of their operations and their expected needs for capital. If our
subsidiaries continue to achieve net income at current levels and conditions in
the insurance markets remain relatively consistent, then we currently anticipate
that our subsidiaries should begin to pay dividends to the parent company in
2004.

         Historically, the operations and financing obligations of 21st Century
as the parent company have required approximately $1.3 million per year. We
anticipate that some of our obligations will be met through future dividends
from our subsidiaries and the remainder from our existing sources of capital,
such as our revolving loan. The most likely reason why we would not be able to
meet our obligations is if a catastrophic event expected to occur no more often
than once in every 100 years were actually to occur and simultaneously, our
reinsurance arrangements were to fail. If we need additional sources of capital,
we currently expect that we would offer our securities to investors or obtain
financing secured by our assets.

                    NOTE REGARDING FORWARD-LOOKING STATEMENTS

         Statements in this prospectus or in documents incorporated by reference
that are not historical fact are forward-looking statements. Forward-looking
statements are subject to certain risks and uncertainties that could cause
actual events and results to differ materially from those discussed herein.
Without limiting the generality of the foregoing, words such as "may," "will,"
"expect," "believe," "anticipate," "intend," "could," "would," "estimate," or
"continue" or the negative other variations thereof or comparable terminology
are intended to identify forward-looking statements. The risks and uncertainties


                                       10


include, but are not limited to, the risks and uncertainties described in this
prospectus or from time to time in our filings with the SEC.

                                 USE OF PROCEEDS

         We will not receive any proceeds from the resale of the common stock by
the selling shareholders.

                              SELLING SHAREHOLDERS

         The following table shows certain information as of the date of this
prospectus regarding the number of shares of common stock owned by the selling
shareholders and that are included for sale in this prospectus. The table
assumes that all shares offered for sale in the prospectus are sold.

         No selling shareholder has been within the last three years, or is
currently, affiliated with us.


                                                  OWNERSHIP OF                                 OWNERSHIP OF
                                                  COMMON STOCK                                 COMMON STOCK
                                                 BEFORE OFFERING        NUMBER OFFERED       AFTER OFFERING
                                                ------------------        BY SELLING        ------------------
            SELLING SHAREHOLDER                 NUMBER     PERCENT       SHAREHOLDER        NUMBER     PERCENT
            -------------------                 ------     -------      --------------      ------     -------
                                                                                         
Coastal Convertibles LTD                        50,538      1.34%           3,582              46,956   1.25%
Omicron Master Trust                            33,692        *             2,388              31,304     *
OTAPE Investments LLC                           16,846        *             1,194              15,652     *
Newport Alternative Income Fund                  6,737        *               477               6,260     *
Pandora Select Partners, LP                     67,384      1.78%           4,776              62,608   1.67%
SilverCreek II Limited                          18,868        *             1,337              17,531     *
SilverCreek Limited Partnership                 41,418      1.10%           2,961              38,457   1.03%
Whitebox Convertible
  Arbitrage Partners, LP                       134,768      3.57%           9,552             125,216   3.34%
Whitebox Hedged High
  Yield Partners, LP                           134,768      3.57%           9,552             125,216   3.34%


----------
* Less than 1%.

         The selling shareholders listed above have provided us with additional
information regarding the individuals or entities that exercise control over the
selling shareholder. The proceeds of any sale of shares pursuant to this
prospectus will be for the benefit of the individuals that control the selling
entity. The following is a list of the selling shareholders and the entities
that may exercise the right to vote or dispose of the shares owned by each
selling shareholder:

    o    Coastal Convertibles LTD is managed by Tradewinds.

    o    Omicron Master Trust is managed by Omicron.

    o    OTAPE Investments, LLC is managed by OTA.

    o    Each of Newport Alternative Income Fund, SilverCreek II Limited and
         SilverCreek Limited Partnership is managed by SilverCreek.

    o    Each of Whitebox Convertible Arbitrage Partners, LP and Whitebox Hedged
         High Yield Partners, LP is managed by Whitebox Advisors, LLC.

    o    Pandora Select Partners, LP is managed by Pandora Select Advisors, LLC.

                                       11

                        HOW THE SHARES MAY BE DISTRIBUTED

         The selling shareholders may sell shares of common stock in various
ways and at various prices. Some of the methods by which the selling
shareholders may sell shares include:

         o        ordinary brokerage transactions and transactions in which the
                  broker solicits purchasers or makes arrangements for other
                  brokers to participate in soliciting purchasers;

         o        privately negotiated transactions;

         o        block trades in which the broker or dealer will attempt to
                  sell the shares as agent but may position and resell a portion
                  of the block as principal to facilitate the transaction;

         o        purchases by a broker or dealer as principal and resale by
                  that broker or dealer for the selling shareholder's account
                  under this prospectus on the Nasdaq National Market at prices
                  and on terms then-prevailing in the market;

         o        sales under Rule 144, if available, rather than using this
                  prospectus;

         o        a combination of any of these methods of sale; and

         o        any other legally permitted method.


         The applicable sales price may be affected by the type of transaction.

         The selling shareholders may also pledge shares as collateral for
margin loans under their customer agreements with their brokers. If there is a
default by a selling shareholder, the broker may offer and sell the pledged
shares. When selling shares, the selling shareholders intend to comply with the
prospectus delivery requirements under the Securities Act, by delivering a
prospectus to each purchaser. We may file any supplements, amendments or other
necessary documents in compliance with the Securities Act that may be required
in the event a selling shareholder defaults under any customer agreement with
brokers.

         Brokers and dealers may receive commissions or discounts from the
selling shareholders or, in the event the broker-dealer acts as agent for the
purchaser of the shares, from that purchaser, in amounts to be negotiated. These
commissions are not expected to exceed those customary in the types of
transactions involved.

         We cannot estimate at the present time the amount of commissions or
discounts, if any, that will be paid by the selling shareholders in connection
with the sales of the shares.

         The selling shareholders and any broker-dealers or agents that
participate with a selling shareholder in sales of the shares may be deemed to
be "underwriters" within the meaning of the Securities Act in connection with
such sales. In that event, any commissions received by the broker-dealers or
agents and any profit on the resale of the shares purchased by them may be
deemed to be underwriting commissions or discounts under the Securities Act.

                                       12


         Under the securities laws of certain states, the shares may be sold in
those states only through registered or licensed broker-dealers. In addition,
the shares may not be sold unless the shares have been registered or qualified
for sale in the relevant state or unless the shares qualify for an exemption
from registration or qualification.

         We have agreed to pay all of our out-of-pocket expenses and our
professional fees and expenses incident to the registration of the shares.

         The selling shareholders and other persons participating in the
distribution of the shares offered under this prospectus are subject to the
applicable requirements of Regulation M promulgated under the Exchange Act in
connection with sales of the shares.

                                  LEGAL MATTERS

         Broad and Cassel, a partnership including professional associations,
Miami, Florida, is giving an opinion regarding the validity of the offered
shares of common stock.

                                     EXPERTS

         The financial statements of 21st Century Holding Company for the years
ended December 31, 2003 and December 31, 2002, incorporated by reference in this
prospectus, have been audited by De Meo, Young, McGrath, independent certified
public accountants, to the extent and for the periods set forth in their report
incorporated herein by reference, and are incorporated herein in reliance upon
such reports given upon the authority of said firm as experts in auditing and
accounting.

         The financial statements of 21st Century Holding Company for the year
ended December 31, 2001, incorporated by reference in this prospectus, have been
audited by McKean, Paul, Chrycy, Fletcher & Co., independent certified public
accountants, to the extent and for the periods set forth in their report
incorporated herein by reference, and are incorporated herein in reliance upon
such reports given upon the authority of said firm as experts in auditing and
accounting.

                       WHERE YOU CAN FIND MORE INFORMATION

         We have filed a registration statement on Form S-3 with the SEC in
connection with this offering. This prospectus does not contain all of the
information set forth in the registration statement, as permitted by the rules
and regulations of the SEC. This prospectus may include references to material
contracts or other material documents of ours; any summaries of these material
contracts or documents are complete and are either included in this prospectus
or incorporated by reference into this prospectus. You may refer to the exhibits
that are part of the registration statement for a copy of the contract or
document.

         We also file annual, quarterly and current reports and other
information with the SEC. You may read and copy any report or document we file,
and the registration statement, including the exhibits, may be inspected at the
SEC's public reference room located at 450 Fifth Street, N.W., Washington, D.C.
20549. Please call the SEC at 1-800-SEC-0330 for further information on the


                                       13


public reference rooms. Our SEC filings are also available to the public from
the SEC's website at http://www.sec.gov.

         Quotations for the prices of our common stock appear on the Nasdaq
National Market, and reports, proxy statements and other information about us
can also be inspected at the offices of the National Association of Securities
Dealers, Inc., 1735 K Street, N.W., Washington, D.C. 20006.

                INCORPORATION OF CERTAIN INFORMATION BY REFERENCE

         The following documents are incorporated by reference into this
prospectus:

         o        Our Annual Report on Form 10-K for the year ended December 31,
                  2003, filed with the SEC on April 2, 2004,

         o        Our proxy statement for our 2004 Annual Meeting of
                  Shareholders filed with the SEC on April 27, 2003, and

         o        The description of our common stock contained in our
                  registration statement on Form 8-A filed with the SEC on
                  October 28, 1998, as this description may be updated in any
                  amendment to the Form 8-A.

         In addition, all documents filed by us pursuant to Sections 13(a),
13(c), 14 or 15(d) of the Securities Exchange Act of 1934, other than
information furnished pursuant to Items 9 or 12 of Form 8-K, after the date of
this prospectus and prior to the filing of a post-effective amendment that
indicates that all securities registered hereby have been sold or that
deregisters all securities then remaining unsold, shall be deemed to be
incorporated by reference into this prospectus and to be a part hereof from the
date of filing of such documents with the SEC. Any statement contained in a
document incorporated by reference herein shall be deemed to be modified or
superseded for purposes of this prospectus to the extent that a statement
contained herein, or in a subsequently filed document incorporated by reference
herein, modifies or supersedes that statement. Any statement so modified or
superseded shall not be deemed, except as so modified or superseded, to
constitute part of this prospectus.

         You may obtain a copy of these filings, excluding all exhibits unless
we have specifically incorporated by reference an exhibit in this prospectus or
in a document incorporated by reference herein, at no cost, by writing or
telephoning:

                           21st Century Holding Company
                           4161 N.W. 5th Street
                           Plantation, Florida 33317
                           Attention: Gordon Jennings, Chief Financial Officer
                           Telephone: (954) 581-9993

         Our file number under the Securities Exchange Act of 1934 is 0-2500111.

                                       14


                    INDEMNIFICATION OF DIRECTORS AND OFFICERS

         We have authority under Section 607.0850 of the Florida Business
Corporation Act to indemnify our directors and officers to the extent provided
for in that law. Our articles of incorporation provide that we may insure, shall
indemnify and shall advance expenses on behalf of our officers and directors to
the fullest extent not prohibited by law. We also are a party to indemnification
agreements with each of our directors and officers.

         The SEC is of the opinion that indemnification of directors, officers
and controlling persons for liabilities arising under the Securities Act is
against public policy and is, therefore, unenforceable.

                                       15

                                     PART II

                       INFORMATION REQUIRED IN PROSPECTUS

ITEM 14.  OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION.

         The Registrant estimates that its expenses in connection with this
registration statement will be as follows:

           SEC registration fee...........................$    91.90
           Accounting fees and expenses................... 10,000.00
           Legal fees and expenses........................  5,000.00
           Miscellaneous..................................  4,908.10
                                                          ----------

                      Total...............................$20,000.00
                                                          ==========

ITEM 15. INDEMNIFICATION OF DIRECTORS AND OFFICERS.

         The Registrant has authority under Section 607.0850 of the Florida
Business Corporation Act to indemnify its directors and officers to the extent
provided for in such law. The Registrant's Amended and Restated Articles of
Incorporation provide that the Registrant may insure, shall indemnify and shall
advance expenses on behalf of its officers and directors to the fullest extent
not prohibited by law. The Registrant is also a party to indemnification
agreements with each of its directors and officers.

ITEM 16.  EXHIBITS.

           4.1        Specimen of Common Stock Certificate(1)
           4.2        Revised Representative's Warrant Agreement including form
                      of Representative's Warrant(1)
           4.3        Amendment dated October 1, 2003 to Warrant Agreement(2)
           4.4        Form of 6% Senior Subordinated Note due July 31, 2006(3)
           4.5        Form of Redeemable Warrant dated July 31, 2003(3)
           4.6        Unit Purchase Agreement dated July 31, 2003 between the
                      Company and the Purchasers of the 6% Senior Subordinated
                      Notes(4)
           4.7        Amendment to Unit Purchase Agreement and Registration
                      Rights Agreement dated October 15, 2003 between the
                      Company and the Purchasers of the 6% Senior Subordinated
                      Notes(5)
           5.1        Opinion of Broad and Cassel(6)
           23.1       Consent of Broad and Cassel (included in its opinion
                      filed as Exhibit 5.1)(6)
           23.2       Consent of McKean, Paul, Chrycy, Fletcher & Co.(6)
           23.3       Consent of De Meo, Young, McGrath(6)
           24.1       Power of Attorney (7)

----------
(1)      Previously filed as an exhibit of the same number to the Registrant's
         Registration Statement on Form SB-2 (File No. 333-63623) and
         incorporated herein by reference.

                                      II-1


(2)      Previously filed as an exhibit of the same number to the Registrant's
         Registration Statement on Form S-3 (File No. 333-105221) and
         incorporated herein by reference.

(3)      Previously filed as Exhibits 4.1 and 4.2, respectively, to the
         Quarterly Report on Form 10-Q for the quarter ended June 30, 2003 and
         incorporated herein by reference.

(4)      Previously filed as Exhibit 4.5 to the Registrant's Registration
         Statement on Form S-3 (333-109313) and incorporated herein by
         reference.

(5)      Previously filed as Exhibit 4.7 to Amendment No. 1 to the Registrant's
         Registration Statement on Form S-3 (333-108739) and incorporated herein
         by reference.

(6)      Filed herewith.

(7)      Included on page II-4 of this registration statement.

ITEM 17.  UNDERTAKINGS.

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:

             (a) To include any prospectus required by section 10(a)(3) of the
Securities Act of 1933, as amended;

             (b) To reflect in the prospectus any facts or events arising after
the effective date of the 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 the registration
statement; and

             (c) To include any material information with respect to the plan of
distribution not previously disclosed in the registration statement or any
material change to such information in the registration statement.

         (2) That, for the purpose of determining any liability under the
Securities Act of 1933, 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.

         (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.

                                      II-2


         The undersigned Registrant hereby undertakes that, for purposes of
determining any liability under the Securities Act of 1933, each filing of the
Registrant's annual report pursuant to Section 13(a) or Section 15(d) of the
Securities Exchange Act of 1934 (and, where applicable, each filing of an
employee benefit plan's annual report pursuant to Section 15(d) of the
Securities Exchange Act of 1934) 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.

         Insofar as indemnification for liabilities arising under the Securities
Act of 1933 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 SEC such indemnification
is against public policy as expressed in the Securities Act of 1933 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 Securities Act of 1933 and will be governed by the
final adjudication of such issue.

                                      II-3


                                   SIGNATURES

         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-3 and has duly caused this Registration
Statement to be signed on its behalf by the undersigned, thereunto duly
authorized, in the City of Plantation, State of Florida on this 30th day of
April, 2004.

                                21ST CENTURY HOLDING COMPANY


                                By: /s/ Edward J. Lawson
                                -----------------------------------
                                Edward J. Lawson,
                                Chairman of the Board and President



                                POWER OF ATTORNEY

         Each person whose signature appears below constitutes and appoints
Edward J. Lawson and Richard A. Widdicombe, or any one of them, as his or her
true and lawful attorneys-in-fact and agents with full power of substitution and
resubstitution for him or her and in his or her name, place and stead in any and
all capacities to execute in the name of each such person who is then an officer
or director of the Registrant any and all amendments (including post-effective
amendments) to this Registration Statement, and any registration statement
relating to the offering hereunder pursuant to Rule 462 under the Securities Act
of 1933 and to file the same with all exhibits thereto and other documents in
connection therewith with the Securities and Exchange Commission, granting unto
said attorneys-in-fact and agents and each of them full power and authority to
do and perform each and every act and thing required or necessary to be done in
and about the premises as fully as he or she might or could do in person, hereby
ratifying and confirming all that said attorneys-in-fact and agents, or any of
them, or their or his substitute or substitutes, may lawfully do or cause to be
done by virtue thereof.

         Pursuant to the requirements of the Securities Act of 1933, this
registration statement has been signed by the following persons in the
capacities and on the date indicated.

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

/s/ Edward J. Lawson        Chairman of the Board of Directors    April 30, 2004
--------------------------  and President
Edward J. Lawson


/s/ Richard A. Widdicombe   Chief Executive Officer and Director  April 30, 2004
--------------------------   (Principal Executive Officer)
Richard A. Widdicombe

                                      II-4




       SIGNATURES                        TITLE                         DATE
       ----------                        -----                         ----
/s/ James G. Jennings, III  Chief Financial Officer (Principal    April 30, 2004
--------------------------  Financial and Accounting Officer)
James G. Jennings, III


/s/ Carl Dorf               Director                              April 30, 2004
--------------------------
Carl Dorf


                            Director                              April   , 2004
--------------------------
Charles B. Hart, Jr.


                            Director                              April   , 2004
--------------------------
Peter J. Prygelski


                            Director                              April   , 2004
--------------------------
Bruce Simberg


/s/ Richard W. Wilcox, Jr.  Director                              April 30, 2004
--------------------------
Richard W. Wilcox, Jr.



                                      II-5





                                  EXHIBIT INDEX


EXHIBIT    DESCRIPTION
-------    -----------

5.1        Opinion of Broad and Cassel

23.1       Consent of Broad and Cassel (included in its opinion filed as
           Exhibit 5.1)

23.2       Consent of McKean, Paul, Chrycy, Fletcher & Co.

23.3       Consent of De Meo, Young, McGrath