0001493152-23-005589 Sample Contracts

SECURITIES PURCHASE AGREEMENT
Securities Purchase Agreement • February 21st, 2023 • Gaucho Group Holdings, Inc. • Land subdividers & developers (no cemeteries) • Delaware

This SECURITIES PURCHASE AGREEMENT (the “Agreement”), dated as of February 21, 2023, is by and among Gaucho Group Holdings Inc., a Delaware corporation with offices located at 112 NE 41st Street, Suite 106, Miami, Florida 33137 (the “Company”), and each of the investors listed on the Schedule of Buyers attached hereto (individually, a “Buyer” and collectively, the “Buyers”).

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REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • February 21st, 2023 • Gaucho Group Holdings, Inc. • Land subdividers & developers (no cemeteries)

This REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of February 21, 2023, is by and among Gaucho Group Holdings Inc., a Delaware corporation with offices located at 112 NE 41st Street, Suite 106, Miami, Florida 33137 (the “Company”), and the undersigned buyers (each, a “Buyer,” and collectively, the “Buyers”).

SECURITY AND PLEDGE AGREEMENT
Security and Pledge Agreement • February 21st, 2023 • Gaucho Group Holdings, Inc. • Land subdividers & developers (no cemeteries) • New York

WHEREAS, the Company is party to that certain Securities Purchase Agreement, dated as of February 21, 2023 (as amended, modified, supplemented, extended, renewed, restated or replaced from time to time in accordance with the terms thereof, the “Securities Purchase Agreement”), by and among the Company and each party listed as a “Buyer” on the Schedule of Buyers attached thereto (each a “Buyer” and collectively, the “Buyers”), pursuant to which the Company shall be required to sell, and the Buyers shall purchase or have the right to purchase, the “Notes” issued pursuant thereto (as such Notes may be amended, modified, supplemented, extended, renewed, restated or replaced from time to time in accordance with the terms thereof, collectively, the “Notes”) and the “Warrants” issued pursuant thereto (as such Warrants may be amended, modified, supplemented, extended, renewed, restated or replaced from time to time in accordance with the terms thereof, collectively, the “Warrants”); and

STOCKHOLDER PLEDGE AGREEMENT
Stockholder Pledge Agreement • February 21st, 2023 • Gaucho Group Holdings, Inc. • Land subdividers & developers (no cemeteries)

This STOCKHOLDER PLEDGE AGREEMENT (this “Agreement”), dated as of February 21, 2023, is made by ____________, a ___________, with a principal address at ________________________ (the “Pledgor”), Gaucho Group Holdings Inc., a Delaware corporation with offices located at 112 NE 41st Street, Suite 106, Miami, Florida 33137 (the “Company”), and the Secured Party listed on the signature page hereof (the “Secured Party”).

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