diff --git a/packages/commons/src/index.ts b/packages/commons/src/index.ts
index aed1788618..17906e6e26 100644
--- a/packages/commons/src/index.ts
+++ b/packages/commons/src/index.ts
@@ -22,6 +22,7 @@ export {
   isNullOrUndefined,
   isNumber,
   isRecord,
+  isRegExp,
   isStrictEqual,
   isString,
   isStringUndefinedNullEmpty,
diff --git a/packages/commons/src/typeUtils.ts b/packages/commons/src/typeUtils.ts
index 2dca860b84..10cc93214f 100644
--- a/packages/commons/src/typeUtils.ts
+++ b/packages/commons/src/typeUtils.ts
@@ -176,6 +176,25 @@ const isStringUndefinedNullEmpty = (value: unknown) => {
   return false;
 };
 
+/**
+ * Check if a Regular Expression
+ *
+ * @example
+ * ```typescript
+ * import { isRegExp } from '@aws-lambda-powertools/commons/typeUtils';
+ *
+ * const value = /^foo.+$/;
+ * if (isRegExp(value)) {
+ *   // value is a Regular Expression
+ * }
+ * ```
+ *
+ * @param value - The value to check
+ */
+const isRegExp = (value: unknown): value is RegExp => {
+  return value instanceof RegExp;
+};
+
 /**
  * Get the type of a value as a string.
  *
@@ -337,6 +356,7 @@ export {
   isNull,
   isNullOrUndefined,
   isStringUndefinedNullEmpty,
+  isRegExp,
   getType,
   isStrictEqual,
 };
diff --git a/packages/commons/tests/unit/typeUtils.test.ts b/packages/commons/tests/unit/typeUtils.test.ts
index 99b281be87..72a719adf6 100644
--- a/packages/commons/tests/unit/typeUtils.test.ts
+++ b/packages/commons/tests/unit/typeUtils.test.ts
@@ -6,6 +6,7 @@ import {
   isNullOrUndefined,
   isNumber,
   isRecord,
+  isRegExp,
   isStrictEqual,
   isString,
   isStringUndefinedNullEmpty,
@@ -224,6 +225,30 @@ describe('Functions: typeUtils', () => {
     });
   });
 
+  describe('Function: isRegExp', () => {
+    it('returns true when the passed value is a Regular Expression', () => {
+      // Prepare
+      const value = /^hello.+$/;
+
+      // Act
+      const result = isRegExp(value);
+
+      // Assess
+      expect(result).toBe(true);
+    });
+
+    it('returns false when the passed value is not a Regular Expression', () => {
+      // Prepare
+      const value = 123;
+
+      // Act
+      const result = isRegExp(value);
+
+      // Assess
+      expect(result).toBe(false);
+    });
+  });
+
   describe('Function: getType', () => {
     it.each([
       {
diff --git a/packages/event-handler/src/rest/RouteHandlerRegistry.ts b/packages/event-handler/src/rest/RouteHandlerRegistry.ts
index 116b95b91e..c191d08398 100644
--- a/packages/event-handler/src/rest/RouteHandlerRegistry.ts
+++ b/packages/event-handler/src/rest/RouteHandlerRegistry.ts
@@ -1,4 +1,5 @@
 import type { GenericLogger } from '@aws-lambda-powertools/commons/types';
+import { isRegExp } from '@aws-lambda-powertools/commons/typeutils';
 import type {
   DynamicRoute,
   HttpMethod,
@@ -11,11 +12,13 @@ import { ParameterValidationError } from './errors.js';
 import { Route } from './Route.js';
 import {
   compilePath,
+  getPathString,
   resolvePrefixedPath,
   validatePathPattern,
 } from './utils.js';
 
 class RouteHandlerRegistry {
+  readonly #regexRoutes: Map<string, DynamicRoute> = new Map();
   readonly #staticRoutes: Map<string, Route> = new Map();
   readonly #dynamicRoutesSet: Set<string> = new Set();
   readonly #dynamicRoutes: DynamicRoute[] = [];
@@ -44,8 +47,8 @@ class RouteHandlerRegistry {
     }
 
     // Routes with more path segments are more specific
-    const aSegments = a.path.split('/').length;
-    const bSegments = b.path.split('/').length;
+    const aSegments = getPathString(a.path).split('/').length;
+    const bSegments = getPathString(b.path).split('/').length;
 
     return bSegments - aSegments;
   }
@@ -103,6 +106,18 @@ class RouteHandlerRegistry {
 
     const compiled = compilePath(route.path);
 
+    if (isRegExp(route.path)) {
+      if (this.#regexRoutes.has(route.id)) {
+        this.#logger.warn(
+          `Handler for method: ${route.method} and path: ${route.path} already exists. The previous handler will be replaced.`
+        );
+      }
+      this.#regexRoutes.set(route.id, {
+        ...route,
+        ...compiled,
+      });
+      return;
+    }
     if (compiled.isDynamic) {
       const dynamicRoute = {
         ...route,
@@ -171,28 +186,10 @@ class RouteHandlerRegistry {
       };
     }
 
-    for (const route of this.#dynamicRoutes) {
-      if (route.method !== method) continue;
-
-      const match = route.regex.exec(path);
-      if (match?.groups) {
-        const params = match.groups;
-
-        const processedParams = this.#processParams(params);
-
-        const validation = this.#validateParams(processedParams);
-
-        if (!validation.isValid) {
-          throw new ParameterValidationError(validation.issues);
-        }
-
-        return {
-          handler: route.handler,
-          params: processedParams,
-          rawParams: params,
-          middleware: route.middleware,
-        };
-      }
+    const routes = [...this.#dynamicRoutes, ...this.#regexRoutes.values()];
+    for (const route of routes) {
+      const result = this.#processRoute(route, method, path);
+      if (result) return result;
     }
 
     return null;
@@ -215,6 +212,7 @@ class RouteHandlerRegistry {
     const routes = [
       ...routeHandlerRegistry.#staticRoutes.values(),
       ...routeHandlerRegistry.#dynamicRoutes,
+      ...routeHandlerRegistry.#regexRoutes.values(),
     ];
     for (const route of routes) {
       this.register(
@@ -227,6 +225,28 @@ class RouteHandlerRegistry {
       );
     }
   }
+
+  #processRoute(route: DynamicRoute, method: HttpMethod, path: Path) {
+    if (route.method !== method) return;
+
+    const match = route.regex.exec(getPathString(path));
+    if (!match) return;
+
+    const params = match.groups || {};
+    const processedParams = this.#processParams(params);
+    const validation = this.#validateParams(processedParams);
+
+    if (!validation.isValid) {
+      throw new ParameterValidationError(validation.issues);
+    }
+
+    return {
+      handler: route.handler,
+      params: processedParams,
+      rawParams: params,
+      middleware: route.middleware,
+    };
+  }
 }
 
 export { RouteHandlerRegistry };
diff --git a/packages/event-handler/src/rest/utils.ts b/packages/event-handler/src/rest/utils.ts
index b0943d3e4f..caf4ad82f8 100644
--- a/packages/event-handler/src/rest/utils.ts
+++ b/packages/event-handler/src/rest/utils.ts
@@ -1,5 +1,9 @@
 import { Readable, Writable } from 'node:stream';
-import { isRecord, isString } from '@aws-lambda-powertools/commons/typeutils';
+import {
+  isRecord,
+  isRegExp,
+  isString,
+} from '@aws-lambda-powertools/commons/typeutils';
 import type { APIGatewayProxyEvent } from 'aws-lambda';
 import type {
   CompiledRoute,
@@ -18,13 +22,21 @@ import {
   UNSAFE_CHARS,
 } from './constants.js';
 
+export function getPathString(path: Path): string {
+  return isString(path) ? path : path.source.replaceAll(/\\\//g, '/');
+}
+
 export function compilePath(path: Path): CompiledRoute {
   const paramNames: string[] = [];
 
-  const regexPattern = path.replace(PARAM_PATTERN, (_match, paramName) => {
-    paramNames.push(paramName);
-    return `(?<${paramName}>[${SAFE_CHARS}${UNSAFE_CHARS}\\w]+)`;
-  });
+  const pathString = getPathString(path);
+  const regexPattern = pathString.replace(
+    PARAM_PATTERN,
+    (_match, paramName) => {
+      paramNames.push(paramName);
+      return `(?<${paramName}>[${SAFE_CHARS}${UNSAFE_CHARS}\\w]+)`;
+    }
+  );
 
   const finalPattern = `^${regexPattern}$`;
 
@@ -39,9 +51,10 @@ export function compilePath(path: Path): CompiledRoute {
 export function validatePathPattern(path: Path): ValidationResult {
   const issues: string[] = [];
 
-  const matches = [...path.matchAll(PARAM_PATTERN)];
-  if (path.includes(':')) {
-    const expectedParams = path.split(':').length;
+  const pathString = getPathString(path);
+  const matches = [...pathString.matchAll(PARAM_PATTERN)];
+  if (pathString.includes(':')) {
+    const expectedParams = pathString.split(':').length;
     if (matches.length !== expectedParams - 1) {
       issues.push('Malformed parameter syntax. Use :paramName format.');
     }
@@ -227,14 +240,24 @@ export const composeMiddleware = (middleware: Middleware[]): Middleware => {
 /**
  * Resolves a prefixed path by combining the provided path and prefix.
  *
+ * The function returns a RegExp if any of the path or prefix is a RegExp.
+ * Otherwise, it returns a `/${string}` type value.
+ *
  * @param path - The path to resolve
  * @param prefix - The prefix to prepend to the path
  */
 export const resolvePrefixedPath = (path: Path, prefix?: Path): Path => {
-  if (prefix) {
-    return path === '/' ? prefix : `${prefix}${path}`;
+  if (!prefix) return path;
+  if (isRegExp(prefix)) {
+    if (isRegExp(path)) {
+      return new RegExp(`${getPathString(prefix)}/${getPathString(path)}`);
+    }
+    return new RegExp(`${getPathString(prefix)}${path}`);
+  }
+  if (isRegExp(path)) {
+    return new RegExp(`${prefix}/${getPathString(path)}`);
   }
-  return path;
+  return `${prefix}${path}`.replace(/\/$/, '') as Path;
 };
 
 export const HttpResponseStream =
diff --git a/packages/event-handler/src/types/rest.ts b/packages/event-handler/src/types/rest.ts
index ae7f9f8d5f..4fa17c36a2 100644
--- a/packages/event-handler/src/types/rest.ts
+++ b/packages/event-handler/src/types/rest.ts
@@ -75,7 +75,7 @@ type HttpMethod = keyof typeof HttpVerbs;
 
 type HttpStatusCode = (typeof HttpStatusCodes)[keyof typeof HttpStatusCodes];
 
-type Path = `/${string}`;
+type Path = `/${string}` | RegExp;
 
 type RestRouteHandlerOptions = {
   handler: RouteHandler;
diff --git a/packages/event-handler/tests/unit/rest/Router/basic-routing.test.ts b/packages/event-handler/tests/unit/rest/Router/basic-routing.test.ts
index a2de67e709..3fdd5b0954 100644
--- a/packages/event-handler/tests/unit/rest/Router/basic-routing.test.ts
+++ b/packages/event-handler/tests/unit/rest/Router/basic-routing.test.ts
@@ -190,4 +190,32 @@ describe('Class: Router - Basic Routing', () => {
       'Handler for method: GET and path: /todos already exists. The previous handler will be replaced.'
     );
   });
+
+  it.each([
+    ['/files/test', 'GET', 'serveFileOverride'],
+    ['/api/v1/test', 'GET', 'apiVersioning'],
+    ['/users/1/files/test', 'GET', 'dynamicRegex1'],
+    ['/any-route', 'GET', 'getAnyRoute'],
+    ['/no-matches', 'POST', 'catchAllUnmatched'],
+  ])('routes %s %s to %s handler', async (path, method, expectedApi) => {
+    // Prepare
+    const app = new Router();
+    app.get(/\/files\/.+/, async () => ({ api: 'serveFile' }));
+    app.get(/\/files\/.+/, async () => ({ api: 'serveFileOverride' }));
+    app.get(/\/api\/v\d+\/.*/, async () => ({ api: 'apiVersioning' }));
+    app.get(/\/users\/:userId\/files\/.+/, async (reqCtx) => ({
+      api: `dynamicRegex${reqCtx.params.userId}`,
+    }));
+    app.get(/.+/, async () => ({ api: 'getAnyRoute' }));
+    app.route(async () => ({ api: 'catchAllUnmatched' }), {
+      path: /.*/,
+      method: [HttpVerbs.GET, HttpVerbs.POST],
+    });
+
+    // Act
+    const result = await app.resolve(createTestEvent(path, method), context);
+
+    // Assess
+    expect(JSON.parse(result.body).api).toEqual(expectedApi);
+  });
 });
diff --git a/packages/event-handler/tests/unit/rest/utils.test.ts b/packages/event-handler/tests/unit/rest/utils.test.ts
index 478b7225bb..8b0fbeadad 100644
--- a/packages/event-handler/tests/unit/rest/utils.test.ts
+++ b/packages/event-handler/tests/unit/rest/utils.test.ts
@@ -581,12 +581,15 @@ describe('Path Utilities', () => {
       { path: '/test', prefix: '/prefix', expected: '/prefix/test' },
       { path: '/', prefix: '/prefix', expected: '/prefix' },
       { path: '/test', expected: '/test' },
+      { path: /.+/, prefix: '/prefix', expected: /\/prefix\/.+/ },
+      { path: '/test', prefix: /\/prefix/, expected: /\/prefix\/test/ },
+      { path: /.+/, prefix: /\/prefix/, expected: /\/prefix\/.+/ },
     ])('resolves prefixed path', ({ path, prefix, expected }) => {
       // Prepare & Act
       const resolvedPath = resolvePrefixedPath(path as Path, prefix as Path);
 
       // Assert
-      expect(resolvedPath).toBe(expected);
+      expect(resolvedPath).toEqual(expected);
     });
   });