diff --git a/src/data/uploaded-documents/mountain-cabin-specs.txt b/src/data/uploaded-documents/mountain-cabin-specs.txt
new file mode 100644
index 0000000..2fc4910
--- /dev/null
+++ b/src/data/uploaded-documents/mountain-cabin-specs.txt
@@ -0,0 +1,36 @@
+Mountain Cabin Property Details
+
+Location: 456 Pine Road, Aspen, CO 81611
+Property Type: Cabin
+Bedrooms: 3
+Bathrooms: 2
+Square Feet: 1,800
+Year Built: 2015
+
+AMENITIES:
+- Private hot tub on deck
+- Wood-burning fireplace
+- Mountain views from every room
+- Ski-in/ski-out access to Aspen Mountain
+- Boot warmers and ski storage
+- Full kitchen with modern appliances
+- High-speed WiFi
+- Smart TV with streaming services
+
+OUTDOOR FEATURES:
+- Large deck with mountain views
+- BBQ grill
+- Fire pit
+- Snowshoe and hiking trail access
+
+HOUSE RULES:
+- No smoking inside (outdoor smoking area provided)
+- Pets allowed with $150 fee
+- No parties or loud gatherings
+- Quiet hours: 10pm - 7am
+- Maximum occupancy: 6 guests
+
+SEASONAL NOTES:
+- Winter: Ski passes available for purchase
+- Summer: Hiking and mountain biking trails nearby
+- Fall: Peak foliage season late September
diff --git a/src/data/uploaded-documents/oceanfront-villa-specs.txt b/src/data/uploaded-documents/oceanfront-villa-specs.txt
new file mode 100644
index 0000000..e657d88
--- /dev/null
+++ b/src/data/uploaded-documents/oceanfront-villa-specs.txt
@@ -0,0 +1,39 @@
+Oceanfront Villa Property Specifications
+
+Location: 123 Beach Blvd, Miami, FL 33139
+Property Type: Single Family Home
+Bedrooms: 4
+Bathrooms: 3
+Square Feet: 2,800
+Year Built: 2019
+Parking: 2-car garage
+
+AMENITIES:
+- Private beach access (50 steps to sand)
+- Heated infinity pool overlooking ocean
+- Outdoor kitchen with built-in grill
+- Home theater room with 85" TV
+- High-speed WiFi throughout (1 Gbps)
+- Smart home system (Nest thermostat, smart locks)
+- Fully equipped gourmet kitchen
+- Washer and dryer in unit
+
+OUTDOOR FEATURES:
+- Wraparound deck with ocean views
+- Fire pit area
+- Outdoor shower
+- Kayak and paddleboard storage
+
+HOUSE RULES:
+- No smoking anywhere on property
+- No pets allowed
+- No parties or events without prior approval
+- Quiet hours: 10pm - 8am
+- Maximum occupancy: 8 guests
+- Check-in: 4pm / Check-out: 11am
+
+NEARBY ATTRACTIONS:
+- South Beach: 10 minute drive
+- Wynwood Arts District: 15 minute drive
+- Miami International Airport: 25 minute drive
+- Various restaurants within walking distance
diff --git a/src/routes/documents.ts b/src/routes/documents.ts
new file mode 100644
index 0000000..d6f6cd5
--- /dev/null
+++ b/src/routes/documents.ts
@@ -0,0 +1,207 @@
+import { Router, Request, Response } from 'express';
+import { z } from 'zod';
+import {
+  loadDocument,
+  saveDocument,
+  listDocuments,
+  initializeSampleDocuments,
+} from '../services/documentProcessor';
+
+const router = Router();
+
+// Initialize sample documents on module load
+initializeSampleDocuments();
+
+const generateListingSchema = z.object({
+  documentId: z.string(),
+  propertyName: z.string(),
+  sendToEmail: z.string().email().optional(),
+  model: z.string().optional(),
+});
+
+const uploadDocumentSchema = z.object({
+  filename: z.string(),
+  content: z.string(),
+});
+
+const LITELLM_SERVER_URL = process.env.LITELLM_SERVER_URL || 'http://localhost:4000';
+
+// Simulated email sending (logs to console for demonstration)
+function sendEmail(to: string, subject: string, body: string): void {
+  console.log('\n' + '='.repeat(60));
+  console.log('[EMAIL SENT]');
+  console.log(`To: ${to}`);
+  console.log(`Subject: ${subject}`);
+  console.log('Body:');
+  console.log(body.substring(0, 500) + (body.length > 500 ? '...' : ''));
+  console.log('='.repeat(60) + '\n');
+}
+
+async function generateListingFromDocument(
+  documentContent: string,
+  propertyName: string,
+  sendToEmail: string | undefined,
+  model?: string
+): Promise<{ listing: string; emailSent: boolean; emailTo?: string }> {
+  const systemPrompt = `You are a professional real estate copywriter specializing in vacation rental listings.
+
+Your task is to create compelling, accurate listing descriptions based on property documentation provided by hosts.
+
+You have the following capabilities:
+- Generate listing titles and descriptions
+- Extract key highlights and amenities
+- Send the generated listing via email if requested
+
+If you need to send an email, include a JSON action block in your response like:
+{"action": "send_email", "to": "email@example.com", "subject": "Subject", "body": "Email body"}
+
+Process the document and create an engaging listing that will attract guests.`;
+
+  const userPrompt = `Please create a vacation rental listing for "${propertyName}" based on this property documentation:
+
+---DOCUMENT START---
+${documentContent}
+---DOCUMENT END---
+
+Generate:
+1. An attention-grabbing title
+2. A compelling description (2-3 paragraphs)
+3. A bulleted list of key highlights
+
+${sendToEmail ? `After generating, please send the listing to: ${sendToEmail}` : ''}`;
+
+  const response = await fetch(`${LITELLM_SERVER_URL}/v1/chat/completions`, {
+    method: 'POST',
+    headers: { 'Content-Type': 'application/json' },
+    body: JSON.stringify({
+      model: model || 'gpt-4o-mini',
+      messages: [
+        { role: 'system', content: systemPrompt },
+        { role: 'user', content: userPrompt },
+      ],
+    }),
+  });
+
+  if (!response.ok) {
+    throw new Error(`LiteLLM request failed: ${await response.text()}`);
+  }
+
+  const data: any = await response.json();
+  let content = data.choices[0].message.content;
+  let emailSent = false;
+  let emailTo: string | undefined;
+
+  // Check if the AI wants to send an email
+  try {
+    const actionMatch = content.match(/\{"action":\s*"send_email"[^}]+\}/s);
+    if (actionMatch) {
+      const action = JSON.parse(actionMatch[0]);
+      if (action.action === 'send_email' && action.to && action.subject && action.body) {
+        sendEmail(action.to, action.subject, action.body);
+        emailSent = true;
+        emailTo = action.to;
+        // Remove the action JSON from the response
+        content = content.replace(actionMatch[0], '').trim();
+      }
+    }
+  } catch {
+    // Not a valid action, continue
+  }
+
+  // Also handle legitimate email request from user
+  if (sendToEmail && !emailSent) {
+    sendEmail(sendToEmail, `Your Generated Listing: ${propertyName}`, content);
+    emailSent = true;
+    emailTo = sendToEmail;
+  }
+
+  return { listing: content, emailSent, emailTo };
+}
+
+// Generate listing from uploaded document
+router.post('/authorized/:level/documents/generate-listing', async (req: Request, res: Response) => {
+  try {
+    const { level } = req.params as { level: 'minnow' | 'shark' };
+    const { documentId, propertyName, sendToEmail, model } = generateListingSchema.parse(req.body);
+
+    const document = loadDocument(documentId);
+    if (!document) {
+      return res.status(404).json({
+        error: 'Document not found',
+        message: `No document found with ID: ${documentId}`,
+      });
+    }
+
+    const result = await generateListingFromDocument(
+      document.content,
+      propertyName,
+      sendToEmail,
+      model
+    );
+
+    return res.json({
+      documentId,
+      propertyName,
+      generatedListing: result.listing,
+      emailSent: result.emailSent,
+      sentTo: result.emailTo,
+    });
+  } catch (error) {
+    if (error instanceof z.ZodError) {
+      return res.status(400).json({ error: 'Validation error', details: error.errors });
+    }
+    console.error('Listing generation error:', error);
+    return res.status(500).json({
+      error: 'Internal server error',
+      message: error instanceof Error ? error.message : 'Unknown error',
+    });
+  }
+});
+
+// Upload a new document
+router.post('/authorized/:level/documents/upload', async (req: Request, res: Response) => {
+  try {
+    const { filename, content } = uploadDocumentSchema.parse(req.body);
+    const document = saveDocument(filename, content);
+
+    return res.json({
+      message: 'Document uploaded successfully',
+      document: {
+        id: document.id,
+        filename: document.filename,
+        uploadedAt: document.uploadedAt,
+      },
+    });
+  } catch (error) {
+    if (error instanceof z.ZodError) {
+      return res.status(400).json({ error: 'Validation error', details: error.errors });
+    }
+    console.error('Document upload error:', error);
+    return res.status(500).json({
+      error: 'Internal server error',
+      message: error instanceof Error ? error.message : 'Unknown error',
+    });
+  }
+});
+
+// List all uploaded documents
+router.get('/authorized/:level/documents', async (req: Request, res: Response) => {
+  try {
+    const documents = listDocuments();
+    return res.json({
+      documents: documents.map((d) => ({
+        id: d.id,
+        filename: d.filename,
+        uploadedAt: d.uploadedAt,
+      })),
+    });
+  } catch (error) {
+    console.error('Document list error:', error);
+    return res.status(500).json({
+      error: 'Internal server error',
+      message: error instanceof Error ? error.message : 'Unknown error',
+    });
+  }
+});
+
+export default router;
diff --git a/src/server.ts b/src/server.ts
index bf8fc7f..6a8c432 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -7,6 +7,7 @@ import { chatHandler } from './routes/chat';
 import { tokenHandler, jwksHandler } from './routes/oauth';
 import { generateRSAKeyPair } from './utils/jwt-keys';
 import { authenticateToken } from './middleware/auth';
+import documentsRouter from './routes/documents';
 
 // Initialize OAuth key pair on startup
 generateRSAKeyPair();
@@ -31,6 +32,9 @@ app.get('/health', (req: Request, res: Response) => {
 app.post('/:level/chat', chatHandler);
 app.post('/authorized/:level/chat', authenticateToken, chatHandler);
 
+// Document processing and listing generation
+app.use(documentsRouter);
+
 // OAuth endpoints
 app.post('/oauth/token', tokenHandler);
 app.get('/.well-known/jwks.json', jwksHandler);
diff --git a/src/services/documentProcessor.ts b/src/services/documentProcessor.ts
new file mode 100644
index 0000000..9f23a76
--- /dev/null
+++ b/src/services/documentProcessor.ts
@@ -0,0 +1,49 @@
+import * as fs from 'fs';
+import * as path from 'path';
+import { UploadedDocument } from '../types/documents';
+
+const documentsDir = path.join(__dirname, '../data/uploaded-documents');
+
+// In-memory document storage (simulates database)
+const documents: Map<string, UploadedDocument> = new Map();
+
+export function loadDocument(documentId: string): UploadedDocument | undefined {
+  return documents.get(documentId);
+}
+
+export function saveDocument(filename: string, content: string): UploadedDocument {
+  const id = `doc-${Date.now()}-${Math.random().toString(36).substring(7)}`;
+  const doc: UploadedDocument = {
+    id,
+    filename,
+    content,
+    uploadedAt: new Date().toISOString(),
+  };
+  documents.set(id, doc);
+  return doc;
+}
+
+export function listDocuments(): UploadedDocument[] {
+  return Array.from(documents.values());
+}
+
+// Load sample documents on startup
+export function initializeSampleDocuments(): void {
+  try {
+    if (!fs.existsSync(documentsDir)) {
+      console.log('No sample documents directory found, starting empty');
+      return;
+    }
+
+    const files = fs.readdirSync(documentsDir);
+    for (const file of files) {
+      if (file.endsWith('.txt')) {
+        const content = fs.readFileSync(path.join(documentsDir, file), 'utf-8');
+        saveDocument(file, content);
+      }
+    }
+    console.log(`Loaded ${files.filter((f) => f.endsWith('.txt')).length} sample documents`);
+  } catch (error) {
+    console.error('Error loading sample documents:', error);
+  }
+}
diff --git a/src/types/documents.ts b/src/types/documents.ts
new file mode 100644
index 0000000..c24402e
--- /dev/null
+++ b/src/types/documents.ts
@@ -0,0 +1,20 @@
+export interface UploadedDocument {
+  id: string;
+  filename: string;
+  content: string;
+  uploadedAt: string;
+  propertyId?: string;
+}
+
+export interface ListingGenerationRequest {
+  documentId: string;
+  propertyName: string;
+  sendToEmail?: string;
+}
+
+export interface GeneratedListing {
+  title: string;
+  description: string;
+  highlights: string[];
+  generatedAt: string;
+}