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                                                               EXHIBIT 99 (a)(5)

                       FORM OF LETTER TO BROKERS, DEALERS

                       [Chester Bancorp, Inc. Letterhead]

                                  July 10, 2001

          Re:  Offer to Purchase for Cash by Chester Bancorp, Inc. up to 250,000
               shares of its Common Stock at a Purchase price of $17.75 Per
               Share. The offer, proration period and withdrawal rights expire
               at 5:00 p.m., Central Daylight Time, on August 15, 2001, unless
               the offer is extended.

To Brokers, Dealers, Commercial Banks, Trust Companies and Other Nominees:

We are enclosing the material listed below relating to our offer to purchase up
to 250,000 shares of our Common Stock at a purchase price of $17.75, net to the
seller in cash, without interest, as specified by tendering shareholders. Our
offer is being made on the terms and subject to the conditions set forth in the
Offer to Purchase, and the related Letter of Transmittal (as amended or
supplemented from time to time).

Only Common shares validly tendered and not withdrawn, will be purchased.
However, because of the proration provisions described in the Offer to Purchase,
all Common shares tendered may not be purchased if more than 250,000 Common
shares are tendered. All shares tendered and not purchased, including shares not
purchased because of proration or the conditional tender procedures, will be
returned at Chester Bancorp's expense promptly following the expiration date.

We reserve the right, in our sole discretion, to purchase additional shares in
the offer up to 2% of the outstanding shares of Common Stock, subject to
applicable legal requirements.

As described in the Offer to Purchase, if more than 250,000 common shares have
been validly tendered and not withdrawn, we will purchase validly tendered (and
not withdrawn) common shares in the following order of priority:

          o    First, we will purchase shares from all holders of "odd lots" of
               less than 100 shares who have properly tendered all of their
               shares at the purchase price prior to the expiration date and
               completed the "Odd Lots" box in the Letter of Transmittal and, if
               applicable, in the Notice of Guaranteed Delivery;

          o    Second, we will purchase all shares conditionally tendered in
               accordance with Section 5 of the Offer to Purchase for which the
               condition was satisfied without regard to the procedure in the
               next bulleted clause, and all other shares tendered properly and
               unconditionally on a pro rata basis if necessary; and

          o    Finally, if necessary to permit us to purchase 250,000 shares,
               shares conditionally tendered (for which the condition was not
               initially satisfied) and not withdrawn prior to the expiration
               date, will be selected for purchase by random lot in accordance
               with the Offer to Purchase -- provided that, to be eligible for
               purchase by random lot, all Common shares owned by the tendering
               shareholder must have been properly tendered and the appropriate
               box must have been checked in the "Conditional Tenders" box in
               the Letter of Transmittal and, if applicable, in the Notice of
               Guaranteed Delivery.

For your information and for forwarding to your clients for whom you hold shares
registered in your name (or in the name of your nominee), we are enclosing the
following documents:

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          1.   The Offer to Purchase;

          2.   The Letter of Transmittal for your use and for the information of
               your clients (together with accompanying instructions and
               Substitute Form W-9);

          3.   A letter to Chester Bancorp, Inc.'s shareholders from the
               Chairman, President and Chief Financial Officer of Chester
               Bancorp, Inc.;

          4.   A Notice of Guaranteed Delivery to be used to accept the Offer if
               the shares and all other required documents cannot be delivered
               to the Depositary by the expiration date; and

          5.   A letter that may be sent to your clients for whose accounts you
               hold shares registered in your name or in the name of your
               nominee, with space provided for obtaining such clients'
               instructions with regard to the offer.

Your prompt action is requested. We urge you to contact your clients as promptly
as possible. The offer, proration period and withdrawal rights expire at 5:00
p.m., Central Daylight Time, on August 15, 2001, unless the offer is extended.

We will not pay any fees or commissions to any broker, dealer or other person
for soliciting tenders of shares pursuant to the Offer. We will, upon written
request, reimburse brokers, dealers, commercial banks and trust companies for
reasonable and customary handling and mailing expenses incurred by them in
forwarding materials related to the offer to their customers. We will pay all
stock transfer taxes applicable to our purchase of Shares pursuant to the offer,
except as otherwise provided in the Offer to Purchase and Instruction 6 of the
Letter of Transmittal.

Any questions or requests for assistance or additional copies of the enclosed
materials should be directed to Chester Bancorp, Inc. You may reach Chester
Bancorp, Inc. at the address on the last page of the Offer to Purchase, or by
calling 1-800-851-5371.

Thank you for your consideration.

                                        Sincerely,



                                        /s/ Michael W. Welge
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                                                    Michael W. Welge
                                        Chairman, President, and Chief Financial
                                        Officer

Nothing contained herein or in the enclosed documents shall constitute you or
any person the agent of Chester Bancorp, Inc. or the Depositary, or authorize
you or any other person to use any document or make any statement on behalf of
any of them in connection with the tender offer other than the documents
enclosed herewith and the statements contained herein.

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