<PAGE>




                                              Registration No. _______________

                       Securities and Exchange Commission
                             Washington, D.C. 20549

                                    FORM S-8

             REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933

                           THE DEWOLFE COMPANIES, INC.
                       (EXACT NAME OF ISSUER AS SPECIFIED
                                 IN ITS CHARTER)

        MASSACHUSETTS                                 04-2895334
(STATE OR OTHER JURISDICTION OF           (I.R.S. EMPLOYER IDENTIFICATION NO.)
INCORPORATION OR ORGANIZATION)

                80 Hayden Avenue, Lexington, Massachusetts 02421
                    (ADDRESS OF PRINCIPAL EXECUTIVE OFFICES)

                           THE DEWOLFE COMPANIES, INC.
                             1998 STOCK OPTION PLAN
                            (FULL TITLE OF THE PLAN)

                               Richard B. DeWolfe
                           The DeWolfe Companies, Inc.
                                80 Hayden Avenue
                         Lexington, Massachusetts 02421
                                 (781) 863-5858

                                   COPIES TO:
                          Patrick J. Kinney, Jr., Esq.
                       Lynch, Brewer, Hoffman & Sands, LLP
                               101 Federal Street
                           Boston, Massachusetts 02110
                                 (617) 951-0800
          (NAME, ADDRESS AND TELEPHONE NUMBER OF AGENT FOR SERVICE)

         Approximate date of Commencement of Sale pursuant to the plan: Upon
issuance and exercise of options.


<PAGE>

<TABLE>
<CAPTION>

                              CALCULATION OF REGISTRATION FEE

      Title of                      Proposed         Proposed
     securities     Amount           maximum         maximum           Amount of
       to be        to be        offering price   aggregate offer-     registra-
    registered    registered(1)     per share(2)    ing price           tion fee
  --------------  -------------  ---------------  ----------------    ------------
  <S>             <C>            <C>              <C>                 <C>
  Common Stock,
    $.01 par
      value          409,700          $6.50          $2,663,050        $703.05
</TABLE>

(1)      The registration statement also includes an indeterminable number of
         additional shares that may become issuable as a result of terminated,
         expired or surrendered options or pursuant to the antidilution
         provisions of the Plan.

(2)      Computed on the basis of the closing sales price of securities of the
         same class, as reported on the American Stock Exchange on
         December 17, 1999.

                                       2
<PAGE>


                                     PART II

               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

Item 3.  INCORPORATION OF DOCUMENTS BY REFERENCE.

         Certain important information is set forth in certain reports or
statements filed by The DeWolfe Companies, Inc. (the "Company") with the
Securities and Exchange Commission. The reports or documents listed below are
incorporated herein by reference:

                  (a) The DeWolfe Companies, Inc.'s (the "Company") latest
Annual Report on Form 10-K for the fiscal year ended December 31, 1998 (which
incorporates by reference certain portions of the Company's Proxy Statement for
the Company's 1999 Annual Meeting of Stockholders held on May 11, 1999);

                  (b)  The Company's latest Quarterly Report on Form 10-Q for
the fiscal quarter ended March 31, 1999;

                  (c)  The Company's latest Quarterly Report on Form 10-Q for
the fiscal quarter ended June 30, 1999;

                  (d) The Company's latest Quarterly Report on Form 10-Q for the
fiscal quarter ended September 30, 1999;

                  (e) All other reports filed by the Company pursuant to Section
13 or 15(d) of the Securities Exchange Act of 1934 for periods since September
30, 1999; and

                  (f) The information set forth under "Description of
Registrant's Securities to be Registered" in the Company's Registration
Statement on Form 8-A filed on April 15, 1995 (File No. 1-11278) which
incorporates by reference the description of the Company's securities contained
in the Company's Registration Statement on Form S-18 (File No. 33-48113-B).

         All documents filed by the Company pursuant to Sections 13(a), 13(c),
14 and 15(d) of the Securities Exchange Act of 1934, prior to the filing of a
post-effective amendment which indicates that all securities offered have been
sold or which deregisters all securities then remaining unsold, shall be deemed
to be incorporated by reference and to be a part hereof from the date of filing
such reports and documents.



                                       3
<PAGE>


Item 4.  DESCRIPTION OF SECURITIES.

                  Not applicable.

Item 5.  EXPERTS

                  The consolidated financial statements of The DeWolfe
Companies, Inc. appearing in The DeWolfe Companies, Inc. Annual Report (Form
10-K) for the year ended December 31, 1998, have been audited by Ernst & Young
LLP, independent auditors, as set forth in their report thereon included therein
and incorporated herein by reference. Such consolidated financial statements are
incorporated herein by reference in reliance upon such report given on the
authority of such firm as experts in accounting and auditing.

Item 6.  INDEMNIFICATION OF DIRECTORS AND OFFICERS

                  Section 67 of the Massachusetts Business Corporation Law and
Section 9 of the By-Laws of the Company provide for indemnification of directors
and officers under certain circumstances. In addition, Article 6 of the
Company's Restated Articles of Organization provides for the limitation of
liability of directors under certain circumstances.


Item 7.  EXEMPTION FROM REGISTRATION CLAIMED.

                  Not Applicable.


Item 8.  EXHIBITS.

                  The Exhibit Index immediately preceding the exhibits is
incorporated herein by reference.


Item 9.  UNDERTAKINGS.

         A.       The Company hereby undertakes:

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

                  (i)  To include any prospectus required by Section 10(a)(3)
                  of the Securities Act of 1933;


                                       4
<PAGE>



                  (ii) To reflect in the prospectus any facts or events arising
                  after the effective date of the registration statement which,
                  individually or in the aggregate, represent a fundamental
                  change in the information set forth in the registration
                  statement;

                  (iii) 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; PROVIDED, HOWEVER,
                  that paragraphs (A)(1)(i) and (A)(1)(ii) do not apply if the
                  information required to be in a post-effective amendment by
                  those paragraphs is contained in periodic reports filed by the
                  Company pursuant to Section 13 or Section 15(d) of the
                  Securities Exchange Act of 1934 that are incorporated by
                  reference 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 Plan.

         B. The Company hereby undertakes that, for purposes of determining any
liability under the Securities Act of 1933, each filing of the Company'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.

         C. Insofar as indemnification for liabilities under the Securities Act
of 1933 may be permitted to directors, officers, and controlling persons of the
Company pursuant to the foregoing provisions or otherwise, the Company has been
advised that in the opinion of the Securities and Exchange Commission 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



                                     5
<PAGE>



against such liabilities (other than the payment by the Company of expenses
incurred or paid by a director, officer or controlling person of the Company
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 Company 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.











                                      6
<PAGE>



                                   SIGNATURES

         Pursuant to the requirements of the Securities Act of 1933, the
Company certifies that it has reasonable grounds to believe that it meets all
of the requirements for filing on Form S-8 and has duly caused this
Registration Statement to be signed on its behalf by the undersigned,
thereunto duly authorized in City of Lexington, Massachusetts, on this 21st
day of December, 1999.

                                       THE DEWOLFE COMPANIES, INC.



                                       By  /s/ Richard B. DeWolfe
                                           -----------------------------------
                                           Richard B. DeWolfe, President
                                           (Principal Executive Officer)



                                       By  /s/ James A. Marcotte
                                          ------------------------------------
                                           James A. Marcotte
                                           Senior Vice President
                                           (Principal Financial Officer)




                                      7
<PAGE>


                                POWER OF ATTORNEY

         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 dates indicated. By so signing, each of the undersigned
in his capacity as a director or officer, or both, as the case may be, does
hereby appoint Richard B. DeWolfe, Edward S. Brewer, Jr. and Patrick J.
Kinney, Jr., or any one of them acting singly, his lawful attorney to execute
in his name, place and stead, any and all amendments to said Registration
Statement and all instruments necessary or incidental in connection
therewith, and to file the same with the Securities and Exchange Commission.
Said attorney shall have the full powers and authority to do and perform in
the name and on behalf of each of the undersigned, in any and all capacities,
every act whatsoever requisite or necessary to be done in the premises as
fully, and to all intents and purposes, as each of the undersigned might do
in person, hereby ratifying, and approving the acts of such attorney.

                                         Title                     Date
                                        -------                   ------

/s/ Richard B. DeWolfe          Chairman of the Board,      December 21, 1999
--------------------------        President, Chief
    Richard B. DeWolfe            Executive Officer,
                                  and Treasurer

/s/ James A. Marcotte           Senior Vice President       December 21, 1999
-------------------------         and Chief Financial
    James A. Marcotte             Officer

/s/ A. Clinton Allen            Director                    December 21, 1999
-------------------------
    A. Clinton Allen


/s/ R. Robert Popeo             Director                    December 21, 1999
-------------------------
    R. Robert Popeo


/s/ Paul R. Del Rossi           Director                    December 21, 1999
-------------------------
    Paul R. Del Rossi



                                       8
<PAGE>


                                  EXHIBIT INDEX
<TABLE>
<CAPTION>

Exhibit                                                               Sequentially
Number                       Description                              Numbered Page
-------                     ------------                              -------------
<S>      <C>                                                          <C>
4.1      Restated Articles of Organization of the Company
         [incorporated herein by reference to the Company's
         Registration Statement on Form S-18 (File No.
         33-48113-B)]                                                      N/A

4.2      Amendment to the Certificate of Incorporation
         [incorporated by reference to the Company's Proxy
         Statement for its 1995 Annual Meeting of Stockholders]            N/A

4.3      By-laws of the Company [incorporated by reference
         to the Company's Quarterly Report on Form 10-Q for
         the quarter ended June 30, 1999 (File No. 1-11278)]               N/A

4.4      Specimen Stock Certificate [incorporated by reference
         to the Company's Registration Statement on
         Form S-18 (File No. 33-48113-B)]                                  N/A

4.5      The Company's 1998 Stock Option Plan, as amended
         [incorporated by reference to the Company's Proxy
         Statement for its 1999 Annual Meeting of Stockholders]            N/A

5        Opinion of Lynch, Brewer, Hoffman & Sands, LLP                    10

23.1     Consent of Lynch, Brewer, Hoffman & Sands, LLP                    N/A
         (included in Exhibit 5)

23.2     Consent of Ernst & Young LLP                                      11

24       Power of Attorney                                                 8

99       Copy of Section 67 of the Massachusetts Business
         Corporation Law with respect to indemnification of
         officers and directors [incorporated by reference to the
         Company's Registration Statement on Form S-18
         (File No. 33-48113-B)]                                            N/A
</TABLE>



                                       9
[{"type": "S-8", "sequence": "1", "description": "FORM S-8", "secsgml_size_bytes": 15551}]
{"company-data": {"conformed-name": "DEWOLFE COMPANIES INC", "cik": "0000888138", "assigned-sic": "6531", "irs-number": "042895334", "state-of-incorporation": "MA", "fiscal-year-end": "1231"}, "filing-values": {"form-type": "S-8", "act": "33", "file-number": "333-93513", "film-number": "99779769"}, "business-address": {"street1": "80 HAYDEN AVE", "city": "LEXINGTON", "state": "MA", "zip": "02173", "phone": "6178635858"}, "mail-address": {"street1": "30 HAYDEN AVE", "city": "LEXINGTON", "state": "MA", "zip": "02173"}}
Registration No. _______________

                       Securities and Exchange Commission
                             Washington, D.C. 20549

                                    FORM S-8

             REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933

                           THE DEWOLFE COMPANIES, INC.
                       (EXACT NAME OF ISSUER AS SPECIFIED
                                 IN ITS CHARTER)

        MASSACHUSETTS                                 04-2895334
(STATE OR OTHER JURISDICTION OF           (I.R.S. EMPLOYER IDENTIFICATION NO.)
INCORPORATION OR ORGANIZATION)

                80 Hayden Avenue, Lexington, Massachusetts 02421
                    (ADDRESS OF PRINCIPAL EXECUTIVE OFFICES)

                           THE DEWOLFE COMPANIES, INC.
                             1998 STOCK OPTION PLAN
                            (FULL TITLE OF THE PLAN)

                               Richard B. DeWolfe
                           The DeWolfe Companies, Inc.
                                80 Hayden Avenue
                         Lexington, Massachusetts 02421
                                 (781) 863-5858

                                   COPIES TO:
                          Patrick J. Kinney, Jr., Esq.
                       Lynch, Brewer, Hoffman & Sands, LLP
                               101 Federal Street
                           Boston, Massachusetts 02110
                                 (617) 951-0800
          (NAME, ADDRESS AND TELEPHONE NUMBER OF AGENT FOR SERVICE)

         Approximate date of Commencement of Sale pursuant to the plan: Upon
issuance and exercise of options.
CALCULATION OF REGISTRATION FEE

      Title of                      Proposed         Proposed
     securities     Amount           maximum         maximum           Amount of
       to be        to be        offering price   aggregate offer-     registra-
    registered    registered(1)     per share(2)    ing price           tion fee
  --------------  -------------  ---------------  ----------------    ------------
Common Stock,
    $.01 par
      value          409,700          $6.50          $2,663,050        $703.05
(1)      The registration statement also includes an indeterminable number of
         additional shares that may become issuable as a result of terminated,
         expired or surrendered options or pursuant to the antidilution
         provisions of the Plan.

(2)      Computed on the basis of the closing sales price of securities of the
         same class, as reported on the American Stock Exchange on
         December 17, 1999.

                                       2
PART II

               INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

Item 3.  INCORPORATION OF DOCUMENTS BY REFERENCE.

         Certain important information is set forth in certain reports or
statements filed by The DeWolfe Companies, Inc. (the "Company") with the
Securities and Exchange Commission. The reports or documents listed below are
incorporated herein by reference:

                  (a) The DeWolfe Companies, Inc.'s (the "Company") latest
Annual Report on Form 10-K for the fiscal year ended December 31, 1998 (which
incorporates by reference certain portions of the Company's Proxy Statement for
the Company's 1999 Annual Meeting of Stockholders held on May 11, 1999);

                  (b)  The Company's latest Quarterly Report on Form 10-Q for
the fiscal quarter ended March 31, 1999;

                  (c)  The Company's latest Quarterly Report on Form 10-Q for
the fiscal quarter ended June 30, 1999;

                  (d) The Company's latest Quarterly Report on Form 10-Q for the
fiscal quarter ended September 30, 1999;

                  (e) All other reports filed by the Company pursuant to Section
13 or 15(d) of the Securities Exchange Act of 1934 for periods since September
30, 1999; and

                  (f) The information set forth under "Description of
Registrant's Securities to be Registered" in the Company's Registration
Statement on Form 8-A filed on April 15, 1995 (File No. 1-11278) which
incorporates by reference the description of the Company's securities contained
in the Company's Registration Statement on Form S-18 (File No. 33-48113-B).

         All documents filed by the Company pursuant to Sections 13(a), 13(c),
14 and 15(d) of the Securities Exchange Act of 1934, prior to the filing of a
post-effective amendment which indicates that all securities offered have been
sold or which deregisters all securities then remaining unsold, shall be deemed
to be incorporated by reference and to be a part hereof from the date of filing
such reports and documents.

                                       3
Item 4.  DESCRIPTION OF SECURITIES.

                  Not applicable.

Item 5.  EXPERTS

                  The consolidated financial statements of The DeWolfe
Companies, Inc. appearing in The DeWolfe Companies, Inc. Annual Report (Form
10-K) for the year ended December 31, 1998, have been audited by Ernst & Young
LLP, independent auditors, as set forth in their report thereon included therein
and incorporated herein by reference. Such consolidated financial statements are
incorporated herein by reference in reliance upon such report given on the
authority of such firm as experts in accounting and auditing.

Item 6.  INDEMNIFICATION OF DIRECTORS AND OFFICERS

                  Section 67 of the Massachusetts Business Corporation Law and
Section 9 of the By-Laws of the Company provide for indemnification of directors
and officers under certain circumstances. In addition, Article 6 of the
Company's Restated Articles of Organization provides for the limitation of
liability of directors under certain circumstances.

Item 7.  EXEMPTION FROM REGISTRATION CLAIMED.

                  Not Applicable.

Item 8.  EXHIBITS.

                  The Exhibit Index immediately preceding the exhibits is
incorporated herein by reference.

Item 9.  UNDERTAKINGS.

         A.       The Company hereby undertakes:

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

                  (i)  To include any prospectus required by Section 10(a)(3)
                  of the Securities Act of 1933;

                                       4
(ii) To reflect in the prospectus any facts or events arising
                  after the effective date of the registration statement which,
                  individually or in the aggregate, represent a fundamental
                  change in the information set forth in the registration
                  statement;

                  (iii) 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; PROVIDED, HOWEVER,
                  that paragraphs (A)(1)(i) and (A)(1)(ii) do not apply if the
                  information required to be in a post-effective amendment by
                  those paragraphs is contained in periodic reports filed by the
                  Company pursuant to Section 13 or Section 15(d) of the
                  Securities Exchange Act of 1934 that are incorporated by
                  reference 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 Plan.

         B. The Company hereby undertakes that, for purposes of determining any
liability under the Securities Act of 1933, each filing of the Company'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.

         C. Insofar as indemnification for liabilities under the Securities Act
of 1933 may be permitted to directors, officers, and controlling persons of the
Company pursuant to the foregoing provisions or otherwise, the Company has been
advised that in the opinion of the Securities and Exchange Commission 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

                                     5
against such liabilities (other than the payment by the Company of expenses
incurred or paid by a director, officer or controlling person of the Company
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 Company 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.

                                      6
SIGNATURES

         Pursuant to the requirements of the Securities Act of 1933, the
Company certifies that it has reasonable grounds to believe that it meets all
of the requirements for filing on Form S-8 and has duly caused this
Registration Statement to be signed on its behalf by the undersigned,
thereunto duly authorized in City of Lexington, Massachusetts, on this 21st
day of December, 1999.

                                       THE DEWOLFE COMPANIES, INC.

                                       By  /s/ Richard B. DeWolfe
                                           -----------------------------------
                                           Richard B. DeWolfe, President
                                           (Principal Executive Officer)

                                       By  /s/ James A. Marcotte
                                          ------------------------------------
                                           James A. Marcotte
                                           Senior Vice President
                                           (Principal Financial Officer)

                                      7
POWER OF ATTORNEY

         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 dates indicated. By so signing, each of the undersigned
in his capacity as a director or officer, or both, as the case may be, does
hereby appoint Richard B. DeWolfe, Edward S. Brewer, Jr. and Patrick J.
Kinney, Jr., or any one of them acting singly, his lawful attorney to execute
in his name, place and stead, any and all amendments to said Registration
Statement and all instruments necessary or incidental in connection
therewith, and to file the same with the Securities and Exchange Commission.
Said attorney shall have the full powers and authority to do and perform in
the name and on behalf of each of the undersigned, in any and all capacities,
every act whatsoever requisite or necessary to be done in the premises as
fully, and to all intents and purposes, as each of the undersigned might do
in person, hereby ratifying, and approving the acts of such attorney.

                                         Title                     Date
                                        -------                   ------

/s/ Richard B. DeWolfe          Chairman of the Board,      December 21, 1999
--------------------------        President, Chief
    Richard B. DeWolfe            Executive Officer,
                                  and Treasurer

/s/ James A. Marcotte           Senior Vice President       December 21, 1999
-------------------------         and Chief Financial
    James A. Marcotte             Officer

/s/ A. Clinton Allen            Director                    December 21, 1999
-------------------------
    A. Clinton Allen

/s/ R. Robert Popeo             Director                    December 21, 1999
-------------------------
    R. Robert Popeo

/s/ Paul R. Del Rossi           Director                    December 21, 1999
-------------------------
    Paul R. Del Rossi

                                       8
EXHIBIT INDEX
Exhibit                                                               Sequentially
Number                       Description                              Numbered Page
-------                     ------------                              -------------
4.1      Restated Articles of Organization of the Company
         [incorporated herein by reference to the Company's
         Registration Statement on Form S-18 (File No.
         33-48113-B)]                                                      N/A

4.2      Amendment to the Certificate of Incorporation
         [incorporated by reference to the Company's Proxy
         Statement for its 1995 Annual Meeting of Stockholders]            N/A

4.3      By-laws of the Company [incorporated by reference
         to the Company's Quarterly Report on Form 10-Q for
         the quarter ended June 30, 1999 (File No. 1-11278)]               N/A

4.4      Specimen Stock Certificate [incorporated by reference
         to the Company's Registration Statement on
         Form S-18 (File No. 33-48113-B)]                                  N/A

4.5      The Company's 1998 Stock Option Plan, as amended
         [incorporated by reference to the Company's Proxy
         Statement for its 1999 Annual Meeting of Stockholders]            N/A

5        Opinion of Lynch, Brewer, Hoffman & Sands, LLP                    10

23.1     Consent of Lynch, Brewer, Hoffman & Sands, LLP                    N/A
         (included in Exhibit 5)

23.2     Consent of Ernst & Young LLP                                      11

24       Power of Attorney                                                 8

99       Copy of Section 67 of the Massachusetts Business
         Corporation Law with respect to indemnification of
         officers and directors [incorporated by reference to the
         Company's Registration Statement on Form S-18
         (File No. 33-48113-B)]                                            N/A
9