diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 5fd29d8df..f40e3a80f 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -97,6 +97,17 @@ jobs:
         with:
           name: coverage-bun
           path: coverage/
+
+  bun-windows:
+    name: 'Bun - Windows'
+    runs-on: windows-latest
+    steps:
+      - uses: actions/checkout@v4
+      - uses: oven-sh/setup-bun@v1
+        with:
+          bun-version: '1.1.16'
+      - run: bun run test:bun
+
   fastly:
     name: 'Fastly Compute'
     runs-on: ubuntu-latest
@@ -204,7 +215,6 @@ jobs:
       - run: echo "$COMPARISON"
         name: display comparison
 
-
   perf-measures-type-check-on-main:
     runs-on: ubuntu-latest
     if: github.ref == 'refs/heads/main'
diff --git a/runtime-tests/bun/index.test.tsx b/runtime-tests/bun/index.test.tsx
index 6dda78aba..7b303f839 100644
--- a/runtime-tests/bun/index.test.tsx
+++ b/runtime-tests/bun/index.test.tsx
@@ -152,13 +152,13 @@ describe('Serve Static Middleware', () => {
   it('Should return 200 response - /static/helloworld', async () => {
     const res = await app.request('http://localhost/static/helloworld')
     expect(res.status).toBe(200)
-    expect(await res.text()).toBe('Hi\n')
+    expect(await res.text()).toMatch(/Hi\r?\n/)
   })
 
   it('Should return 200 response - /static/hello.world', async () => {
     const res = await app.request('http://localhost/static/hello.world')
     expect(res.status).toBe(200)
-    expect(await res.text()).toBe('Hi\n')
+    expect(await res.text()).toMatch(/Hi\r?\n/)
   })
 
   it('Should return 200 response - /static-absolute-root/plain.txt', async () => {
diff --git a/src/middleware/serve-static/index.ts b/src/middleware/serve-static/index.ts
index 0f1837f22..9e44a40aa 100644
--- a/src/middleware/serve-static/index.ts
+++ b/src/middleware/serve-static/index.ts
@@ -29,6 +29,17 @@ const ENCODINGS_ORDERED_KEYS = Object.keys(ENCODINGS) as (keyof typeof ENCODINGS
 const DEFAULT_DOCUMENT = 'index.html'
 const defaultPathResolve = (path: string) => path
 
+const isAbsolutePath = (path: string) => {
+  const isUnixAbsolutePath = path.startsWith('/')
+  const hasDriveLetter = /^[a-zA-Z]:\\/.test(path)
+  const isUncPath = /^\\\\[^\\]+\\[^\\]+/.test(path)
+  return isUnixAbsolutePath || hasDriveLetter || isUncPath
+}
+
+const windowsPathToUnixPath = (path: string) => {
+  return path.replace(/^[a-zA-Z]:/, '').replace(/\\/g, '/')
+}
+
 /**
  * This middleware is not directly used by the user. Create a wrapper specifying `getContent()` by the environment such as Deno or Bun.
  */
@@ -43,9 +54,10 @@ export const serveStatic = <E extends Env = Env>(
   let root: string
 
   if (options.root) {
-    if (options.root.startsWith('/')) {
+    if (isAbsolutePath(options.root)) {
       isAbsoluteRoot = true
-      root = new URL(`file://${options.root}`).pathname
+      root = windowsPathToUnixPath(options.root)
+      root = new URL(`file://${root}`).pathname
     } else {
       root = options.root
     }