diff --git a/lib/rules/key-spacing.js b/lib/rules/key-spacing.js
index 083a7e62898..b0491b95fe3 100644
--- a/lib/rules/key-spacing.js
+++ b/lib/rules/key-spacing.js
@@ -347,6 +347,40 @@ module.exports = {
             );
         }
 
+        /**
+         * Starting from the given node (a property.key node here) looks forward
+         * until it finds the colon punctuator and returns it.
+         * @param {ASTNode} node The node to start looking from.
+         * @returns {ASTNode} The colon punctuator.
+         */
+        function getNextColon(node) {
+            return sourceCode.getTokenAfter(node, astUtils.isColonToken);
+        }
+
+        /**
+         * Starting from the given node (a property.key node here) looks forward
+         * until it finds the last token before a colon punctuator and returns it.
+         * @param {ASTNode} node The node to start looking from.
+         * @returns {ASTNode} The last token before a colon punctuator.
+         */
+        function getLastTokenBeforeColon(node) {
+            const colonToken = getNextColon(node);
+
+            return sourceCode.getTokenBefore(colonToken);
+        }
+
+        /**
+         * Starting from the given node (a property.key node here) looks forward
+         * until it finds the first token after a colon punctuator and returns it.
+         * @param {ASTNode} node The node to start looking from.
+         * @returns {ASTNode} The first token after a colon punctuator.
+         */
+        function getFirstTokenAfterColon(node) {
+            const colonToken = getNextColon(node);
+
+            return sourceCode.getTokenAfter(colonToken);
+        }
+
         /**
          * Checks whether a property is a member of the property group it follows.
          * @param {ASTNode} lastMember The last Property known to be in the group.
@@ -355,7 +389,7 @@ module.exports = {
          */
         function continuesPropertyGroup(lastMember, candidate) {
             const groupEndLine = lastMember.loc.start.line,
-                candidateValueStartLine = (isKeyValueProperty(candidate) ? candidate.value : candidate).loc.start.line;
+                candidateValueStartLine = (isKeyValueProperty(candidate) ? getFirstTokenAfterColon(candidate.key) : candidate).loc.start.line;
 
             if (candidateValueStartLine - groupEndLine <= 1) {
                 return true;
@@ -384,28 +418,6 @@ module.exports = {
             return false;
         }
 
-        /**
-         * Starting from the given a node (a property.key node here) looks forward
-         * until it finds the last token before a colon punctuator and returns it.
-         * @param {ASTNode} node The node to start looking from.
-         * @returns {ASTNode} The last token before a colon punctuator.
-         */
-        function getLastTokenBeforeColon(node) {
-            const colonToken = sourceCode.getTokenAfter(node, astUtils.isColonToken);
-
-            return sourceCode.getTokenBefore(colonToken);
-        }
-
-        /**
-         * Starting from the given a node (a property.key node here) looks forward
-         * until it finds the colon punctuator and returns it.
-         * @param {ASTNode} node The node to start looking from.
-         * @returns {ASTNode} The colon punctuator.
-         */
-        function getNextColon(node) {
-            return sourceCode.getTokenAfter(node, astUtils.isColonToken);
-        }
-
         /**
          * Gets an object literal property's key as the identifier name or string value.
          * @param {ASTNode} property Property node whose key to retrieve.
diff --git a/tests/lib/rules/key-spacing.js b/tests/lib/rules/key-spacing.js
index bd2d5111851..9ac345d39c1 100644
--- a/tests/lib/rules/key-spacing.js
+++ b/tests/lib/rules/key-spacing.js
@@ -1055,6 +1055,35 @@ ruleTester.run("key-spacing", rule, {
             align: "value"
         }],
         parserOptions: { ecmaVersion: 6 }
+    },
+
+    // https://github.com/eslint/eslint/issues/16674
+    {
+        code: `
+        a = {
+            item       : 123,
+            longerItem : (
+              1 + 1
+            ),
+        };
+        `,
+        options: [{
+            align: {
+                beforeColon: true,
+                afterColon: true,
+                on: "colon"
+            }
+        }]
+    },
+    {
+        code: `
+        a = {
+            item: 123,
+            longerItem: // a comment - not a token
+            (1 + 1),
+        };
+        `,
+        options: [{ align: "value" }]
     }],
     invalid: [{
         code: "var a ={'key' : value };",
@@ -2580,5 +2609,31 @@ ruleTester.run("key-spacing", rule, {
             { messageId: "extraKey", data: { computed: "", key: "singleLine" }, line: 2, column: 15, type: "Identifier" },
             { messageId: "extraKey", data: { computed: "", key: "newGroup" }, line: 3, column: 13, type: "Identifier" }
         ]
+    },
+
+    // https://github.com/eslint/eslint/issues/16674
+    {
+        code:
+        `
+        c = {
+            item: 123,
+            longerItem: (
+              1 + 1
+            ),
+        };
+        `,
+        output:
+        `
+        c = {
+            item      : 123,
+            longerItem: (
+              1 + 1
+            ),
+        };
+        `,
+        options: [{ align: "colon" }],
+        errors: [
+            { messageId: "missingKey", data: { computed: "", key: "item" }, line: 3, column: 13, type: "Identifier" }
+        ]
     }]
 });