diff --git a/cli/tests/unit_node/http_test.ts b/cli/tests/unit_node/http_test.ts
index 706c672f14..9feee02728 100644
--- a/cli/tests/unit_node/http_test.ts
+++ b/cli/tests/unit_node/http_test.ts
@@ -751,3 +751,29 @@ Deno.test(
     assertEquals(body, "hello");
   },
 );
+
+Deno.test("[node/http] server emits error if addr in use", async () => {
+  const promise = deferred<void>();
+  const promise2 = deferred<Error>();
+
+  const server = http.createServer();
+  server.listen(9001);
+
+  const server2 = http.createServer();
+  server2.on("error", (e) => {
+    promise2.resolve(e);
+  });
+  server2.listen(9001);
+
+  const err = await promise2;
+  server.close(() => promise.resolve());
+  server2.close();
+  await promise;
+  const expectedMsg = Deno.build.os === "windows"
+    ? "Only one usage of each socket address"
+    : "Address already in use";
+  assert(
+    err.message.startsWith(expectedMsg),
+    `Wrong error: ${err.message}`,
+  );
+});
diff --git a/ext/node/polyfills/http.ts b/ext/node/polyfills/http.ts
index 609a046ac8..52aac4caec 100644
--- a/ext/node/polyfills/http.ts
+++ b/ext/node/polyfills/http.ts
@@ -1610,19 +1610,25 @@ export class ServerImpl extends EventEmitter {
       return;
     }
     this.#ac = ac;
-    this.#server = serve(
-      {
-        handler: handler as Deno.ServeHandler,
-        ...this.#addr,
-        signal: ac.signal,
-        // @ts-ignore Might be any without `--unstable` flag
-        onListen: ({ port }) => {
-          this.#addr!.port = port;
-          this.emit("listening");
+    try {
+      this.#server = serve(
+        {
+          handler: handler as Deno.ServeHandler,
+          ...this.#addr,
+          signal: ac.signal,
+          // @ts-ignore Might be any without `--unstable` flag
+          onListen: ({ port }) => {
+            this.#addr!.port = port;
+            this.emit("listening");
+          },
+          ...this._additionalServeOptions?.(),
         },
-        ...this._additionalServeOptions?.(),
-      },
-    );
+      );
+    } catch (e) {
+      this.emit("error", e);
+      return;
+    }
+
     if (this.#unref) {
       this.#server.unref();
     }