diff --git a/modules/widgets/contact-info.php b/modules/widgets/contact-info.php
index dbcf05e13504..4be69ef06620 100644
--- a/modules/widgets/contact-info.php
+++ b/modules/widgets/contact-info.php
@@ -22,6 +22,8 @@ class Jetpack_Contact_Info_Widget extends WP_Widget {
 		 * Constructor
 		 */
 		function __construct() {
+			global $pagenow;
+
 			$widget_ops = array(
 				'classname'                   => 'widget_contact_info',
 				'description'                 => __( 'Display a map with your location, hours, and contact information.', 'jetpack' ),
@@ -37,14 +39,23 @@ function __construct() {
 
 			if ( is_customize_preview() ) {
 				add_action( 'wp_enqueue_scripts', array( $this, 'enqueue_scripts' ) );
+			} elseif ( 'widgets.php' === $pagenow ) {
+				add_action( 'admin_enqueue_scripts', array( $this, 'enqueue_scripts' ) );
 			}
+
+			add_action( 'wp_ajax_customize-contact-info-api-key', array( $this, 'ajax_check_api_key' ) );
 		}
 
 		/**
 		 * Enqueue scripts and styles.
 		 */
 		public function enqueue_scripts() {
-			wp_enqueue_style( 'contact-info-map-css', plugins_url( 'contact-info/contact-info-map.css', __FILE__ ), null, 20160623 );
+			wp_enqueue_style(
+				'contact-info-map-css',
+				plugins_url( 'contact-info/contact-info-map.css', __FILE__ ),
+				array(),
+				JETPACK__VERSION
+			);
 		}
 
 
@@ -64,8 +75,7 @@ public function defaults() {
 				'email'   => null,
 				'showmap' => 0,
 				'apikey'  => null,
-				'lat'     => null,
-				'lon'     => null,
+				'goodmap' => null,
 			);
 		}
 
@@ -100,9 +110,9 @@ function widget( $args, $instance ) {
 			if ( '' != $instance['address'] ) {
 
 				$showmap = $instance['showmap'];
+				$goodmap = isset( $instance['goodmap'] ) ? $instance['goodmap'] : $this->has_good_map( $instance );
 
-				/** This action is documented in modules/widgets/contact-info.php */
-				if ( $showmap && $this->has_good_map( $instance ) ) {
+				if ( $showmap && true === $goodmap ) {
 					/**
 					 * Set a Google Maps API Key.
 					 *
@@ -112,6 +122,11 @@ function widget( $args, $instance ) {
 					 */
 					$api_key = apply_filters( 'jetpack_google_maps_api_key', $instance['apikey'] );
 					echo $this->build_map( $instance['address'], $api_key );
+				} elseif ( $showmap && is_customize_preview() && true !== $goodmap ) {
+					printf(
+						'<span class="contact-map-api-error" style="display: block;">%s</span>',
+						esc_html( $instance['goodmap'] )
+					);
 				}
 
 				$map_link = $this->build_map_link( $instance['address'] );
@@ -166,13 +181,6 @@ function widget( $args, $instance ) {
 		 * @return array
 		 */
 		function update( $new_instance, $old_instance ) {
-			$update_lat_lon = false;
-			if (
-				! isset( $old_instance['address'] ) ||
-				$this->urlencode_address( $old_instance['address'] ) != $this->urlencode_address( $new_instance['address'] )
-			) {
-				$update_lat_lon = true;
-			}
 
 			$instance            = array();
 			$instance['title']   = wp_kses( $new_instance['title'], array() );
@@ -181,50 +189,6 @@ function update( $new_instance, $old_instance ) {
 			$instance['email']   = wp_kses( $new_instance['email'], array() );
 			$instance['hours']   = wp_kses( $new_instance['hours'], array() );
 			$instance['apikey']  = wp_kses( isset( $new_instance['apikey'] ) ? $new_instance['apikey'] : $old_instance['apikey'], array() );
-			$instance['lat']     = isset( $old_instance['lat'] ) ? floatval( $old_instance['lat'] ) : 0;
-			$instance['lon']     = isset( $old_instance['lon'] ) ? floatval( $old_instance['lon'] ) : 0;
-
-			if ( ! $instance['lat'] || ! $instance['lon'] ) {
-				$update_lat_lon = true;
-			}
-
-			if ( $instance['address'] && $update_lat_lon ) {
-
-				// Get the lat/lon of the user specified address.
-				$address = $this->urlencode_address( $instance['address'] );
-				$path    = 'https://maps.googleapis.com/maps/api/geocode/json?sensor=false&address=' . $address;
-				/** This action is documented in modules/widgets/contact-info.php */
-				$key = apply_filters( 'jetpack_google_maps_api_key', $instance['apikey'] );
-
-				if ( ! empty( $key ) ) {
-					$path = add_query_arg( 'key', $key, $path );
-				}
-				$json = wp_remote_retrieve_body( wp_remote_get( esc_url( $path, null, null ) ) );
-
-				if ( ! $json ) {
-					// The read failed :(
-					esc_html_e( 'There was a problem getting the data to display this address on a map.  Please refresh your browser and try again.', 'jetpack' );
-					die();
-				}
-
-				$json_obj = json_decode( $json );
-
-				if ( 'ZERO_RESULTS' == $json_obj->status ) {
-					// The address supplied does not have a matching lat / lon.
-					// No map is available.
-					$instance['lat'] = '0';
-					$instance['lon'] = '0';
-				} else {
-
-					$loc = $json_obj->results[0]->geometry->location;
-
-					$lat = floatval( $loc->lat );
-					$lon = floatval( $loc->lng );
-
-					$instance['lat'] = "$lat";
-					$instance['lon'] = "$lon";
-				}
-			}
 
 			if ( ! isset( $new_instance['showmap'] ) ) {
 				$instance['showmap'] = 0;
@@ -232,6 +196,8 @@ function update( $new_instance, $old_instance ) {
 				$instance['showmap'] = intval( $new_instance['showmap'] );
 			}
 
+			$instance['goodmap'] = $this->update_goodmap( $old_instance, $instance );
+
 			return $instance;
 		}
 
@@ -245,6 +211,9 @@ function update( $new_instance, $old_instance ) {
 		 */
 		function form( $instance ) {
 			$instance = wp_parse_args( $instance, $this->defaults() );
+			/** This filter is documented in modules/widgets/contact-info.php */
+			$apikey = apply_filters( 'jetpack_google_maps_api_key', $instance['apikey'] );
+
 			wp_enqueue_script(
 				'contact-info-admin',
 				Assets::get_file_url_for_environment(
@@ -255,6 +224,15 @@ function form( $instance ) {
 				20160727
 			);
 
+			if ( is_customize_preview() ) {
+				$customize_contact_info_api_key_nonce = wp_create_nonce( 'customize_contact_info_api_key' );
+				wp_localize_script(
+					'contact-info-admin',
+					'contact_info_api_key_ajax_obj',
+					array( 'nonce' => $customize_contact_info_api_key_nonce )
+				);
+			}
+
 			?>
 			<p>
 				<label for="<?php echo esc_attr( $this->get_field_id( 'title' ) ); ?>"><?php esc_html_e( 'Title:', 'jetpack' ); ?></label>
@@ -264,30 +242,33 @@ function form( $instance ) {
 			<p>
 				<label for="<?php echo esc_attr( $this->get_field_id( 'address' ) ); ?>"><?php esc_html_e( 'Address:', 'jetpack' ); ?></label>
 				<textarea class="widefat" id="<?php echo esc_attr( $this->get_field_id( 'address' ) ); ?>" name="<?php echo esc_attr( $this->get_field_name( 'address' ) ); ?>"><?php echo esc_textarea( $instance['address'] ); ?></textarea>
-				<?php
-				if ( $this->has_good_map( $instance ) ) {
-					?>
-					<input class="jp-contact-info-showmap" id="<?php echo esc_attr( $this->get_field_id( 'showmap' ) ); ?>" name="<?php echo esc_attr( $this->get_field_name( 'showmap' ) ); ?>" value="1" type="checkbox" <?php checked( $instance['showmap'], 1 ); ?> />
-					<label for="<?php echo esc_attr( $this->get_field_id( 'showmap' ) ); ?>"><?php esc_html_e( 'Show map', 'jetpack' ); ?></label>
-					<?php
-				} else {
-					?>
-					<span class="error-message"><?php _e( 'Sorry. We can not plot this address. A map will not be displayed. Is the address formatted correctly?', 'jetpack' ); ?></span>
-					<input id="<?php echo esc_attr( $this->get_field_id( 'showmap' ) ); ?>" name="<?php echo esc_attr( $this->get_field_name( 'showmap' ) ); ?>" value="<?php echo( intval( $instance['showmap'] ) ); ?>" type="hidden" />
-					<?php
-				}
-				?>
+
+				<input class="jp-contact-info-showmap" id="<?php echo esc_attr( $this->get_field_id( 'showmap' ) ); ?>" name="<?php echo esc_attr( $this->get_field_name( 'showmap' ) ); ?>" value="1" type="checkbox" <?php checked( $instance['showmap'], 1 ); ?> />
+				<label for="<?php echo esc_attr( $this->get_field_id( 'showmap' ) ); ?>"><?php esc_html_e( 'Show map', 'jetpack' ); ?></label>
 			</p>
 
-			<p class="jp-contact-info-apikey" style="<?php echo $instance['showmap'] ? '' : 'display: none;'; ?>">
+			<p class="jp-contact-info-admin-map" style="<?php echo $instance['showmap'] ? '' : 'display: none;'; ?>">
 				<label for="<?php echo esc_attr( $this->get_field_id( 'apikey' ) ); ?>">
 					<?php _e( 'Google Maps API Key', 'jetpack' ); ?>
-					<input class="widefat" id="<?php echo esc_attr( $this->get_field_id( 'apikey' ) ); ?>" name="<?php echo esc_attr( $this->get_field_name( 'apikey' ) ); ?>" type="text" value="<?php echo esc_attr( $instance['apikey'] ); ?>" />
+					<input class="widefat" id="<?php echo esc_attr( $this->get_field_id( 'apikey' ) ); ?>" name="<?php echo esc_attr( $this->get_field_name( 'apikey' ) ); ?>" type="text" value="<?php echo esc_attr( $apikey ); ?>" />
 					<br />
 					<small><?php printf( wp_kses( __( 'Google now requires an API key to use their maps on your site. <a href="%s">See our documentation</a> for instructions on acquiring a key.', 'jetpack' ), array( 'a' => array( 'href' => true ) ) ), 'https://jetpack.com/support/extra-sidebar-widgets/contact-info-widget/' ); ?></small>
 				</label>
 			</p>
 
+			<p class="jp-contact-info-admin-map jp-contact-info-embed-map" style="<?php echo $instance['showmap'] ? '' : 'display: none;'; ?>">
+				<?php
+				if ( ! is_customize_preview() && true === $instance['goodmap'] ) {
+					echo $this->build_map( $instance['address'], $apikey ); // phpcs:ignore WordPress.Security.EscapeOutput.OutputNotEscaped
+				} elseif ( true !== $instance['goodmap'] && ! empty( $instance['goodmap'] ) ) {
+					printf(
+						'<span class="notice notice-warning" style="display: block;">%s</span>',
+						esc_html( $instance['goodmap'] )
+					);
+				}
+				?>
+			</p>
+
 			<p>
 				<label for="<?php echo esc_attr( $this->get_field_id( 'phone' ) ); ?>"><?php esc_html_e( 'Phone:', 'jetpack' ); ?></label>
 				<input class="widefat" id="<?php echo esc_attr( $this->get_field_id( 'phone' ) ); ?>" name="<?php echo esc_attr( $this->get_field_name( 'phone' ) ); ?>" type="text" value="<?php echo esc_attr( $instance['phone'] ); ?>" />
@@ -321,7 +302,7 @@ function build_map_link( $address ) {
 
 
 		/**
-		 * Builds map display HTML code from the supplied latitude and longitude.
+		 * Builds map display HTML code from the supplied address.
 		 *
 		 * @param string $address Address.
 		 * @param string $api_key API Key.
@@ -379,16 +360,87 @@ function urlencode_address( $address ) {
 			return urlencode( $address );
 		}
 
+		/**
+		 * Returns the instance's updated 'goodmap' value.
+		 *
+		 * @param array $old_instance Old configuration values.
+		 * @param array $instance Current configuration values.
+		 *
+		 * @return bool|string The instance's updated 'goodmap' value. The value is true if
+		 * $instance can display a good map. If not, returns an error message.
+		 */
+		function update_goodmap( $old_instance, $instance ) {
+			/*
+			 * If we have no address or don't want to show a map,
+			 * no need to check if the map is valid.
+			 */
+			if ( empty( $instance['address'] ) || 0 === $instance['showmap'] ) {
+				return false;
+			}
+
+			/*
+			 * If there have been any changes that may impact the map in the widget
+			 * (adding an address, address changes, new API key, API key change)
+			 * then we want to check whether our map can be displayed again.
+			 */
+			if (
+				! isset( $instance['goodmap'] )
+				|| ! isset( $old_instance['address'] )
+				|| $this->urlencode_address( $old_instance['address'] ) !== $this->urlencode_address( $instance['address'] )
+				|| ! isset( $old_instance['apikey'] )
+				|| $old_instance['apikey'] !== $instance['apikey']
+			) {
+				return $this->has_good_map( $instance );
+			} else {
+				return $instance['goodmap'];
+			}
+		}
+
 		/**
 		 * Check if the instance has a valid Map location.
 		 *
 		 * @param array $instance Widget instance configuration.
 		 *
-		 * @return bool Whether or not there is a valid map.
+		 * @return bool|string Whether or not there is a valid map. If not, return an error message.
 		 */
 		function has_good_map( $instance ) {
-			// The lat and lon of an address that could not be plotted will have values of 0 and 0.
-			return ! ( '0' == $instance['lat'] && '0' == $instance['lon'] );
+			/** This filter is documented in modules/widgets/contact-info.php */
+			$api_key = apply_filters( 'jetpack_google_maps_api_key', $instance['apikey'] );
+			if ( ! empty( $api_key ) ) {
+				$path     = add_query_arg(
+					array(
+						'q'   => rawurlencode( $instance['address'] ),
+						'key' => $api_key,
+					),
+					'https://www.google.com/maps/embed/v1/place'
+				);
+				$response = wp_remote_get( esc_url_raw( $path ) );
+
+				if ( 200 === wp_remote_retrieve_response_code( $response ) ) {
+					return true;
+				} else {
+					return wp_remote_retrieve_body( $response );
+				}
+			}
+
+			return __( 'Please enter a valid Google API Key.', 'jetpack' );
+		}
+
+		/**
+		 * Check the Google Maps API key after an Ajax call from the widget's admin form in
+		 * the Customizer preview.
+		 */
+		function ajax_check_api_key() {
+			if ( isset( $_POST['apikey'] ) ) {
+				if ( check_ajax_referer( 'customize_contact_info_api_key' ) && current_user_can( 'customize' ) ) {
+					$apikey = wp_kses( $_POST['apikey'], array() );
+					$default_instance = $this->defaults();
+					$default_instance['apikey'] = $apikey;
+					wp_send_json( array( 'result' => esc_html( $this->has_good_map( $default_instance ) ) ) );
+				}
+			} else {
+				wp_die();
+			}
 		}
 
 	}
diff --git a/modules/widgets/contact-info/contact-info-admin.js b/modules/widgets/contact-info/contact-info-admin.js
index f51dccda4ac9..9d3d9d46ba6f 100644
--- a/modules/widgets/contact-info/contact-info-admin.js
+++ b/modules/widgets/contact-info/contact-info-admin.js
@@ -1,3 +1,5 @@
+/* global ajaxurl, contact_info_api_key_ajax_obj */
+
 ( function( $ ) {
 	$( document ).on( 'change', '.jp-contact-info-showmap', function() {
 		var $checkbox = $( this ),
@@ -5,7 +7,51 @@
 
 		$checkbox
 			.closest( '.widget' )
-			.find( '.jp-contact-info-apikey' )
+			.find( '.jp-contact-info-admin-map' )
 			.toggle( isChecked );
 	} );
+
+	$( document ).on( 'widget-synced', function( event, widgetContainer ) {
+		// This event fires for all widgets, so restrict this to Contact Info widgets and the API key input.
+		if (
+			! widgetContainer.is( '[id*="widget_contact_info"]' ) ||
+			! $( document.activeElement ).is( 'input[id*="apikey"]' )
+		) {
+			return;
+		}
+
+		event.preventDefault();
+
+		var $apikey_input = widgetContainer.find( 'input[id*="apikey"]' );
+
+		$.post(
+			ajaxurl,
+			{
+				_ajax_nonce: contact_info_api_key_ajax_obj.nonce,
+				action: 'customize-contact-info-api-key',
+				apikey: $apikey_input.val(),
+			},
+			function( data ) {
+				var $map_element = $apikey_input
+					.closest( '.jp-contact-info-admin-map' )
+					.parent()
+					.find( '.jp-contact-info-embed-map' );
+				var $warning_span = $map_element.find( '[class*="notice"]' );
+
+				if ( '1' !== data.result ) {
+					if ( $warning_span.length === 0 ) {
+						$map_element.append(
+							'<span class="notice notice-warning" style="display: block;">' +
+								data.result +
+								'</span>'
+						);
+					} else if ( $warning_span.text() !== data.result ) {
+						$warning_span.text( data.result );
+					}
+				} else {
+					$map_element.empty();
+				}
+			}
+		);
+	} );
 } )( window.jQuery );
diff --git a/modules/widgets/contact-info/contact-info-map.css b/modules/widgets/contact-info/contact-info-map.css
index 7aa9e698a433..b64d2caa0e9a 100644
--- a/modules/widgets/contact-info/contact-info-map.css
+++ b/modules/widgets/contact-info/contact-info-map.css
@@ -1,4 +1,13 @@
 .contact-map {
 	max-width: 100%;
 	border: 0;
+}
+
+.contact-map-api-error {
+	border-left-color: #ffb900;
+	border-left-style: solid;
+	border-left-width: 4px;
+	box-shadow: 0 1px 1px 0 rgba(0,0,0,.1);
+	margin: 5px 0 15px;
+	padding: 1px 12px;
 }
\ No newline at end of file