Your rentalportfolio,running on autopilot.
Oakwood handles rent collection, maintenance, and tenant communication automatically. Built for self-managing landlords with 2–200 units.
No credit card required · Cancel anytime
Small-portfolio landlords in the US. Massive market, completely underserved.
Lost to property managers every month. Money landlords could be keeping.
Tools built specifically for them. Until now. Oakwood changes that.
You are the entire system.
That ends here.
Maintenance chaos
Tenants submit requests with photos. Vendors self-schedule directly with them. No more endless back-and-forth texts on your phone.
Manual rent collection
Automated reminders go out on your schedule. Real-time payment tracking in one place. Late fees applied automatically per your lease rules.
Lease data entry
Upload a lease PDF and Oakwood's AI extracts every field you need. No slow retyping into spreadsheets or other tools.
Contractor coordination
Assign a vendor once; they coordinate timing and access directly with the tenant. You get notified at every step.
Four failures every self-managing landlord knows by heart
One dashboard. Every unit.
Tenant submitted photos → AI categorized to plumbing → Mike's Plumbing auto-dispatched → Time confirmed with tenant → You're notified at every step.
Four steps.
That's it.
Upload Your Lease
Oakwood AI reads your lease PDF and fills in every field automatically. Tenant name, rent, dates, deposit, and fees — extracted in seconds. No retyping.
Invite Your Tenants
Tenants get their own portal for rent payments, maintenance requests, and communication. One invite. Everything connected.
Maintenance Runs Itself
Tenants submit requests with photos. Vendors get assigned and self-schedule. Everyone is notified automatically at every step.
Rent Comes to You
Automated reminders go out before rent is due. Payments tracked in real time. You see who has paid and who has not at a glance.
Four fixes.
One platform.
Keep scrolling — each pain point, solved.
Maintenance Chaos
ends here.
Tenants submit requests with photos directly in their portal. Vendors self-schedule, upload completion photos, and update status automatically. No more back-and-forth texts.
Contractor Coordination
on autopilot.
Assign a vendor once. They pick a time, coordinate with the tenant, and mark the job complete. You get notified at every step without making a single phone call.
Automated Rent Collection
on schedule.
Send payment links directly to tenants. Track payments automatically. Get notified the moment rent is received — no chasing, no spreadsheets.
AI Lease Extraction
in seconds.
Upload your lease PDF and Oakwood reads it automatically. Tenant details, rent amount, dates, security deposit, late fees — pre-filled before you confirm. No data entry.
Oakwood
does it.
Simple pricing forindependent landlords.
Start free, automate your portfolio, upgrade when you grow.
Free
Up to 2 units
- Rent collection & tenant portal
- Lease management
- Centralized maintenance logging
- Document storage
Starter
Up to 15 units
- Everything in Free
- Tenant messaging
- Basic financial reporting
- Maintenance request tracking
- AI lease extraction (3/month)
Growth
Up to 50 units
- Everything in Starter
- Smart Action Center
- Document auto-categorization
- Unlimited AI lease extraction
- Full vendor management, e-signatures & late rent reminders
Autopilot
Up to 200 units
- Everything in Growth
- Auto-dispatch vendors
- AI rent pricing & market insights
- SMS & automated lease renewal
- Public listings & advanced automation
A $2.99 transaction fee applies to each online rent payment across all plans. Managing more than 200 units? Contact us about a Portfolio plan.
Real feedback from
real operators.
Oakwood's AI capabilities give landlords like myself the tools to maximize efficiency and save time across every rental unit. This is exactly what the industry has been missing.
The rent collection dashboard is straightforward. As a landlord I wanted a simple way to manage everything in one place. Oakwood made that happen.
The layout is simple and easy to navigate. The maintenance tab, rent tracking, and document uploads are all in one place. It works.
Your portfolio,finally onautopilot.
Stop juggling texts, spreadsheets, and contractor phone calls. Start your free trial and have your first units running on autopilot in less than 10 minutes.
No credit card required · Cancel anytime · Live in 50 states