Oakwood review
A free web-based toolkit for landlords who want core rental workflows centralized.
Reviewed by iTechGuides Editors · Editorial team · Updated Oct 2026
Oakwood is cloud-based property management software for self-managing landlords handling 2–200 rental units. It brings online rent collection, tenant portals, lease management, maintenance tracking, vendor coordination, document storage, financial reporting and e-signatures into a central web dashboard. Tenants can pay rent, submit maintenance requests and communicate through the portal, while landlords can replace spreadsheets, texts and disconnected administrative tasks with one system. It is best suited to small landlords who want free automation for core property operations.
The published plans show a broad progression from essential workflows to more automation. Free includes rent collection and a tenant portal, lease management, centralized maintenance logging and document storage, with a stated 15-unit limit. Starter adds tenant messaging, basic financial reporting, maintenance request tracking and AI lease extraction. Growth costs $24.99 per month when billed monthly and adds the Smart Action Center, document auto-categorization, unlimited AI lease extraction, vendor management, e-signatures and late-rent reminders. Autopilot adds auto-dispatch vendors, AI rent pricing and market insights, SMS, automated lease renewal, public listings and advanced automation; it is marked as coming soon. A 30-day free trial is available without a card.
Oakwood’s strongest fit is for landlords who need rent collection, tenant communication, maintenance coordination and lease administration in one browser-based product. Its tenant portal and vendor features extend beyond basic payment collection, while AI lease extraction and document organization target repetitive administrative work. The main tradeoff is scope: the product is web-only, and the free plan is designed around 15 units. Landlords seeking mobile access or a broader operational setup may prefer an alternative. Those who want a straightforward web system for centralizing rental workflows should find Oakwood the more natural choice.
Oakwood pros and cons
- Where it wins
- Free plan includes rent collection, portals, leases, maintenance and documents
- AI lease extraction and tenant communication reduce administrative work
- Vendor coordination, reporting and e-signatures support broader workflows
- Where it doesn't
- Web-only access does not provide a mobile app experience
- The free plan is limited to 15 units
- Autopilot is coming soon and currently uses a waitlist
Oakwood fact sheet, pricing and score →
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