As filed with the Securities and Exchange Commission on August 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)

      3661 WEST OAKLAND PARK BLVD, SUITE 300, LAUDERDALE LAKES, FL 33311,
                                 (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
                    3661 WEST OAKLAND PARK BLVD., SUITE 300
                           LAUDERDALE LAKES, FL 33311
                                 (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 (2)         PRICE        REGISTRATION FEE
--------------------------------------------------------------------------------------------------------------------

--------------------------------------------------------------------------------------------------------------------
                                                                                           
Common Stock, $.01 par value     33,310 shares            $22.275                  $741,980.25         $94.01
--------------------------------------------------------------------------------------------------------------------


(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, AUGUST 3, 2004

                                   PROSPECTUS

                         33,310 SHARES OF COMMON STOCK

                          21ST CENTURY HOLDING COMPANY

      This prospectus covers 33,310 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 July 30, 2004, the last reported sale price of the common stock on
the Nasdaq National Market was $22.55 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 August ____, 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.................................................4

      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.............................................................4

      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...............................4

       We may not obtain the necessary regulatory approvals to
            expand the types of insurance products we offer or
            the states in which we operate.....................................5

      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...........................................................5

      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.......................................................5

      Our investment portfolio may suffer reduced returns or
            losses, which would significantly reduce our
            earnings...........................................................6

      Our loss reserves may be inadequate to cover our actual
            liability for losses, causing our results of
            operations to be adversely affected................................6

      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.........................7

      We are subject to significant government regulation,
            which can limit our growth and increase our
            expenses, thereby reducing our earnings............................7

      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.......................................7

      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.................................8

      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.................................................8

      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..........................8

      With operations concentrated in Florida, we could be
            adversely affected by unpredictable catastrophic
            events such as hurricanes and tropical storms......................9

      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....................................................9

      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....................9

      Our largest shareholders control approximately 28% of the
            voting power of our outstanding common stock, which
            could discourage potential acquirors and prevent
            changes in management.............................................10

      We have authorized but unissued preferred stock, which
            could affect rights of holders of common stock....................10

      Our articles of incorporation and bylaws and Florida law
            may discourage takeover attempts and may result in
            entrenchment of management........................................10

      As a holding company, we depend on the earnings of our
            subsidiaries and their ability to pay management
            fees and dividends to the holding company as the
            primary source of our income......................................11

NOTE REGARDING FORWARD-LOOKING STATEMENTS.....................................11


USE OF PROCEEDS...............................................................12

                                       i


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

SELLING SHAREHOLDERS..........................................................12

HOW THE SHARES MAY BE DISTRIBUTED.............................................13

LEGAL MATTERS.................................................................14

EXPERTS.......................................................................14

WHERE YOU CAN FIND MORE INFORMATION...........................................14

INCORPORATION OF CERTAIN INFORMATION BY REFERENCE.............................15

INDEMNIFICATION OF DIRECTORS AND OFFICERS.....................................16



                             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.

RECENT DEVELOPMENTS

      On June 14, 2004, we announced that our Board of Directors approved a
three-for-two stock split in the form of a stock dividend to be distributed on
or about September 7, 2004. The stock dividend will be paid to shareholders of
record at the close of business on August 23, 2004. Shareholders will receive
three shares of common stock for every two shares of our common stock held on
the record date. We currently have approximately 3,785,554 shares of common
stock issued and outstanding.

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 Florida, Louisiana and
Georgia through our wholly owned subsidiaries, Federated National Insurance
Company and American Vehicle Insurance Company. American Vehicle was approved in
August 2003 to be a foreign insurer in the State of Georgia on an excess and
surplus lines basis. Additionally, during March 2004, American Vehicle was
admitted as a foreign insurer in the State of Louisiana to write homeowners' and
general liability insurance.

      During the three months ended March 31, 2004, 46.5%, 36.6%, 2.5% and 14.4%
of the policies we underwrote were for personal automobile insurance,
homeowners' property and casualty insurance, mobile home property and casualty
insurance, and commercial general liability, respectively. During the year ended
December 31, 2003, 67.5%, 23.0%, 2.4% and 7.1% of the policies we underwrote
were for personal automobile insurance, homeowners' property and casualty
insurance, mobile home property and casualty insurance and commercial general
liability, 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 and third-party
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
24 agencies owned by Federated Agency Group, Inc., a wholly owned subsidiary, 47
franchised agencies, approximately 750 independent agents and a select number of
general agents. Through our wholly owned subsidiary, FedUSA, Inc., we franchise
agencies under the FedUSA name. As of March 31, 2004, franchises were granted
for 47 FedUSA agencies, of which 38 were operating and 9 are pending. We intend
to focus our future expansion efforts for our agency network on franchised
agencies.

                                       1


      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. Assurance MGA generates revenue through policy fee income and other
administrative fees from the marketing of companies' products through the
Company's distribution network. Assurance MGA plans to establish relationships
with additional carriers and add additional insurance products in the future.

      We offer electronic tax filing services through Express Tax Service, Inc.,
an 80%-owned subsidiary, as well as franchise opportunities for these services
through EXPRESSTAX. As of March 31, 2004, there were 232 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 approximately
500 licensees nationwide, acting as sales representatives.

      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 the first quarter of 2004,
96.9% were from nonstandard insurance policies and 3.1% were from standard
insurance policies, and 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 and Texas. 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

                                       2


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 3661 West Oakland Park Boulevard,
Suite 300, Lauderdale Lakes, Florida and our telephone number is (954) 581-9993.

                                       3


                        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 beginning to
experience a soft market in our automobile sector while a hard market persists
in our property sector. We cannot predict, however, how long these market
conditions will persist. In the current soft automobile market, increased price
competition may cause us to have to reduce our premiums in order to maintain our
market share, which would result in a decrease in our automobile 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 policies from
third-party insurers, but limited to policies generated from a small number of

                                       4


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. The revolving
loan agreement expires in September 2004 and we intend to negotiate a similar
agreement to replace the expiring agreement.

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 and Texas to underwrite
and sell general liability insurance. The insurance regulators in these states
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. Prior to 2004,
both Federated National and American Vehicle ceded varying amounts their
premiums from automobile insurance policies to Transatlantic Reinsurance
Company. For 2004, neither company has elected to cede any automobile premiums.

                                       5


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
National for liabilities resulting from a storm causing damage totaling $10
million to $156 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. 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. 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 recent years, we have experienced the effects of both fluctuations
in interest rates and volatility in the stock market. During the first quarter
2004, net investment income totaled $0.5 million or 18% of our total net income
of $2.9 million. 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.

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

                                       6


loss and loss adjustment expenses by $1,234,047 in 2003, $90,874 in 2002, and
$2,568,476 in 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
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,
Georgia and Louisiana, 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 24 agencies that we own, 47 agencies that we franchise to others, and
approximately 750 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

                                       7


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
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

                                       8


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 key man 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 currently
trade 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.

                                       9


OUR LARGEST SHAREHOLDERS CONTROL APPROXIMATELY 28% 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 28%
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

                                       10


            disinterested shareholders. A "control share 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 MANAGEMENT FEES AND 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, then we
anticipate that our subsidiaries could 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 and
management fees 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

                                       11


are intended to identify forward-looking statements. The risks and uncertainties
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(1)   NUMBER OFFERED    AFTER OFFERING(1)
                                     -------------------    BY SELLING    ---------------------
         SELLING SHAREHOLDER           NUMBER   PERCENT    SHAREHOLDER      NUMBER    PERCENT
------------------------------------ ------------------- ---------------- ---------  ----------
                                                                                 
Coastal Convertibles LTD               46,369    1.17%       3,331          43,038     1.08%
Omicron Master Trust                   47,128    1.19%       2,221          44,907     1.13%
OTAPE Investments LLC                  10,043     *          1,110           8,933      *
Newport Alternative Income Fund         3,060     *            444           2,616      *
Pandora Select Partners, LP            58,531    1.47%       4,441          54,090     1.36%
SilverCreek II Limited                  8,567     *          1,243           7,324      *
SilverCreek Limited Partnership        18,972     *          2,754          16,218      *
Whitebox Convertible
 Arbitrage Partners, LP               116,313    2.88%       8,883         107,430     2.66%
Whitebox Hedged High
 Yield Partners, LP                   121,036    3.00%       8,883         112,153     2.78%

-------------------
 *    Less than 1%.
(1)   Includes shares underlying warrants held by the selling shareholders (each
      of which is exercisable for 1/2 share of common stock) as follows:
      Coastal Convertibles LTD, 31,735 shares; Omicron Master Trust, 26,157
      shares; OTAPE Investments LLC, 6,539 shares; Newport Alternative Income
      Fund, 2,615 shares; Pandora Select Partners, LP, 49,314 shares;
      SilverCreek II Limited, 7,324 shares; SilverCreek Limited Partnership,
      16,217 shares; Whitebox Convertible Arbitrage Partners, LP, 97,878
      shares; and Whitebox Hedged High Yield Partners, LP, 98,628 shares.


      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  Capital,  L.P., a Delaware  limited  partnership  ("Omicron
            Capital"),  serves as investment  manager to Omicron Master Trust, a
            trust formed under the laws of Bermuda ("Omicron"); Omicron Capital,
            Inc., a Delaware corporation  ("OCI"),  serves as general partner of
            Omicron  Capital;   and  Winchester  Global  Trust  Company  Limited
            ("Winchester")  serves as the trustee of Omicron.  By reason of such
            relationships,  Omicron  Capital  and OCI  may be  deemed  to  share
            dispositive  power  over the  shares of our  common  stock  owned by
            Omicron,   and   Winchester  may  be  deemed  to  share  voting  and
            dispositive  power  over the  shares of our  common  stock  owned by
            Omicron.  Omicron Capital,  OCI and Winchester  disclaim  beneficial
            ownership of such shares of our common  stock.  Omicron  Capital has
            delegated  authority  from the  board  of  directors  of  Winchester
            regarding the  portfolio  management  decisions  with respect to the
            shares of common  stock owned by Omicron  and, as of April 21, 2003,
            Mr. Olivier H. Morali and Mr. Bruce T.  Bernstein,  officers of OCI,
            have  delegated  authority  from  the  board  of  directors  of  OCI
            regarding the portfolio management decisions of Omicron Capital with
            respect to the shares of common stock owned by Omicron. By reason of
            such delegated authority, Messrs. Morali and Bernstein may be deemed
            to share dispositive power over the shares of our common stock owned
            by  Omicron.   Messrs.  Morali  and  Bernstein  disclaim  beneficial
            ownership  of such  shares of our common  stock and  neither of such
            persons has any legal right to maintain such delegated authority. No
            other  person has sole or shared  voting or  dispositive  power with
            respect to the shares of our common stock being  offered by Omicron,
            as those terms are used for purposes under  Regulation  13D-G of the
            Securities Exchange Act of 1934, as amended.  Omicron and Winchester
            are  not  "affiliates"  of one  another,  as that  term is used  for
            purposes  of the  Securities  Exchange  Act of 1934 or of any  other
            person named in this prospectus as a selling shareholder.  No person
            or "group" (as that term is used in Section 13(d) of the  Securities
            Exchange Act of 1934 or the SEC's Regulation 13D-G) controls Omicron
            and Winchester.

      o     OTAPE Investments, LLC is managed by OTA. Ira M. Leventhal, a U.S.
            citizen, may be deemed to have dispositive power with regard to the
            shares beneficially owned by OTAPE Investments, LLC. Mr. Leventhal
            disclaims beneficial ownership of those shares.

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

                                       12


      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.

                       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.

                                       13


      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.

                                       14


Please call the SEC at 1-800-SEC-0330 for further information on the 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 Quarterly Report on Form 10-Q for the quarter ended March 31,
            2004, filed with the SEC on May 17, 2004,

      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, 2004, 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
                  3661 West Oakland Park Boulevard, Suite 300
                  Lauderdale Lakes, Florida 33311
                  Attention: Gordon Jennings, Chief Financial Officer
                  Telephone: (954) 581-9993

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

                                       15


                   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.

                                       16


                                    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............................. $      94.01
        Accounting fees and expenses.....................     5,000.00
        Legal fees and expenses..........................     5,000.00
        Miscellaneous....................................     4,905.99
                                                          ------------

               Total..................................... $  15,000.00
                                                          ============

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
July, 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         July 30, 2004
------------------------------   Directors and President
Edward J. Lawson

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

                                      II-4


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

/s/ James Gordon Jennings, III   Chief Financial Officer          July 30, 2004
------------------------------   (Principal Financial and
James Gordon Jennings, III       Accounting Officer)

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

/s/ Charles B. Hart, Jr.         Director                         July 30, 2004
------------------------------
Charles B. Hart, Jr.

/s/ Peter J. Prygelski           Director                         July 30, 2004
------------------------------
Peter J. Prygelski

/s/ Bruce Simberg                Director                         July 30, 2004
------------------------------
Bruce Simberg

/s/ Richard W. Wilcox, Jr.       Director                         July 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