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Oakwood
What Oakwood is
Oakwood is web-based property management software for self-managing landlords handling 2–200 units. It combines online rent collection, tenant communication, maintenance requests, lease management, and a tenant portal. Rent features include payment links, automated reminders, and payment tracking; every online rent payment carries a $2.99 transaction fee across all plans. Tenants can submit maintenance requests with photos, while vendors can self-schedule, upload completion photos, and update job status. Oakwood AI extracts tenant details, rent, lease dates, deposits, and fees from uploaded lease PDFs. The Free plan covers 2 units at no cost. Starter covers up to 15 units for $12.99 a month, billed monthly, and includes three AI lease extractions monthly. Growth covers up to 50 units for $24.99 a month, billed monthly; Autopilot covers up to 200 units for $129 a month, billed monthly. Oakwood is available in every U.S. state and offers a 30-day free trial without a credit card. Its only listed platform is the web.
Who it suits
Oakwood is aimed at self-managing landlords with 2–200 units in the United States. It suits owners who want web-based rent, maintenance, tenant, and lease workflows.
What it does well
- Free plan for 2 units
- Online rent links and automated reminders
- AI extracts key lease details
- Tenant maintenance requests with photos
- 30-day trial without a credit card
What to know first
- $2.99 fee on every online rent payment
- Web is the only listed platform
- Free plan covers only 2 units
- Autopilot is listed as coming soon
Plans
| Plan | Billed and limits | Price |
|---|---|---|
| Starter | $12.99/mo · Up to 15 units · Tenant messaging · Basic financial reporting · Maintenance request tracking · AI lease extraction (3/month) | $12.99 a month |
| Growth | $24.99/month · Up to 50 units · Smart Action Center · Document auto-categorization · Unlimited AI lease extraction · Vendor management · E-signatures · Late rent reminders | $24.99 a month |
| Autopilot | $129/month · Up to 200 units · Auto-dispatch vendors · AI rent pricing and market insights · Automated lease renewal · Public listings and advanced automation · Coming soon | $129 a month |
| Free | $0/month · Up to 2 units · Rent collection and tenant portal · Lease management · Centralized maintenance logging · Document storage | On request |
As oakwoodpms.com lists them, read 11 Oct 2026. The maker's own page has the final word.
Verdict
Oakwood brings rent, maintenance, tenant communication, and lease tools into one web service for self-managing landlords. Compare unit limits, payment fees, and plan availability against your portfolio before selecting a tier.
Facts from Oakwood's own pages
- Coverage
- Oakwood says it is available in every U.S. state. · oakwoodpms.com, 11 Oct 2026
- Free plan
- Yes · oakwoodpms.com, 22 Sept 2026
- Included units
- 15 · oakwoodpms.com, 22 Sept 2026
- Intended users
- The product is built for self-managing landlords with 2–200 units. · oakwoodpms.com, 11 Oct 2026
- Lease extraction
- Oakwood AI extracts tenant details, rent, lease dates, deposits, and fees from uploaded lease PDFs. · oakwoodpms.com, 11 Oct 2026
- Lease management
- Yes · oakwoodpms.com, 22 Sept 2026
- Maintenance
- Tenants can submit maintenance requests with photos, and vendors can self-schedule, upload completion photos, and update job status. · oakwoodpms.com, 11 Oct 2026
- Maintenance management
- Yes · oakwoodpms.com, 22 Sept 2026
- Mobile app coverage
- web only · oakwoodpms.com, 22 Sept 2026
- Online rent collection
- Yes · oakwoodpms.com, 22 Sept 2026
- Payment fee
- A $2.99 transaction fee applies to each online rent payment across all plans. · oakwoodpms.com, 11 Oct 2026
- Purpose
- Oakwood handles rent collection, maintenance, and tenant communication for self-managing landlords. · oakwoodpms.com, 11 Oct 2026
- Rent collection
- Oakwood offers online rent payment links, automated reminders, and payment tracking. · oakwoodpms.com, 11 Oct 2026
- Support
- The site lists [email protected] as its support contact. · oakwoodpms.com, 11 Oct 2026
- Tenant portal
- Yes · oakwoodpms.com, 22 Sept 2026
- Trial
- Oakwood advertises a 30-day free trial with no credit card required. · oakwoodpms.com, 11 Oct 2026
- Vendor directory
- Oakwood's Philadelphia vendor directory lists trades including plumbing, electrical, roofing, HVAC, and general contracting. · oakwoodpms.com, 11 Oct 2026
Where Oakwood stands on Freedom251
- Property Management Software#45 of 268