Stessa tracks your books. Keystead closes them.
Stessa is solid free bookkeeping — we mean that. But when you're tired of typing lease terms, matching deposits by hand, and re-categorizing the same expenses every month, Keystead is the step up: AI lease parsing, auto-matched rent, and bank rules that do the work.
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Keystead vs Stessa, honestly
| Feature | Keystead | Stessa |
|---|---|---|
| Price | $29/mo up to 10 units, $79/mo up to 50. 14-day free trial, no card. | Free Essentials plan. Manage $12/mo and Pro $28/mo (billed annually). |
| AI lease parsing | Drop a PDF — tenants, rent, deposits, dates, and clauses extracted with confidence scores and citations back to the document. | Lease documents are stored, but terms are entered by hand. |
| Rent-to-tenant matching | Plaid bank feed auto-matches every ACH, Zelle, and wire to the right tenant by amount, name, and your rules. | Bank feeds import income, but matching deposits to specific tenants is largely manual. |
| Bank rules engine | QuickBooks-style rules: auto-categorize by payee and amount, with transfer detection between your accounts. | Automated bank feeds with category suggestions; no user-defined rules engine or transfer detection. |
| Schedule E export | Included on every plan, aligned line-by-line to the IRS form. Built by a CPA founder. | Schedule E report requires the paid Manage plan ($12/mo) or above. |
| Maintenance / work orders | Work orders with status, assignees, estimates, and actual costs — included on every plan. | Maintenance requests and tracking require the Manage plan or above. |
| Resident portal | Resident portal with email invites for rent and maintenance requests. | Tenant portal with online rent collection and autopay on all plans. |
| Landlord banking | No banking product — Keystead connects to the bank you already have via Plaid. | Built-in Cash Management accounts with APY on balances and cash back. Genuinely useful if you want banking bundled in. |
| Leasing & tenant screening | Not yet — Keystead focuses on what happens after the lease is signed. | Vacancy marketing, Zillow syndication, applications, and tenant screening on all plans. |
Stessa plan details and pricing from stessa.com/pricing, checked June 2026: Essentials free; Manage $12/mo annual ($15 monthly); Pro $28/mo annual ($35 monthly). Features change — confirm current details on each vendor's site.
Who should use Stessa — and who should use Keystead
Stessa makes sense if you have one or two rentals, you mostly need a place to see income and expenses, and free is the deciding factor. Its Essentials plan includes unlimited properties, automatic bank feeds, basic reports, and online rent collection — a lot of product for zero dollars. The leasing tools (Zillow syndication, applications, screening) and the built-in banking with interest on balances are genuine advantages Keystead doesn't offer.
Keystead makes sense when the bookkeeping itself has become the job. If you're spending evenings matching Zelle deposits to tenants, retyping lease terms into a spreadsheet, or re-categorizing the same insurance payment for the twelfth time, that's exactly the work Keystead automates. It's built for self-managing landlords with a handful to a few dozen units who want CPA-grade books without doing CPA-grade data entry.
The AI bookkeeping difference
Most landlord software, Stessa included, treats accounting as a ledger you fill in. Keystead treats it as a pipeline that fills itself. Drop a scanned lease PDF and Claude extracts every term — tenants, rent, deposit, dates, late fees, key clauses — each field with a confidence score and a citation back to the page it came from. Thirty seconds instead of thirty minutes of typing, and you review instead of transcribe.
Then connect your bank through Plaid. Incoming rent — ACH, Zelle, wire — auto-matches to the right tenant by amount, name, and rules you define. Outgoing transactions hit a QuickBooks-style rules engine: your insurance payment categorizes itself to Insurance, your water bill to Utilities, and transfers between your own accounts are detected so they never inflate your income or expenses. Stessa's bank feeds import transactions and suggest categories; Keystead's goal is that by the time you open the books, the work is already done.
Tax time, from a CPA founder
Keystead's founder is a CPA, and it shows most at tax time. Every expense category maps to a specific Schedule E line item: insurance to line 7, mortgage interest to line 12, repairs to line 14, taxes to line 16, utilities to line 17. When January comes, you export a per-property Schedule E report and hand it to your accountant — no shoebox, no "miscellaneous" bucket to untangle, no billable hours spent reconstructing your year.
Stessa offers a Schedule E report too, but it's gated to the paid Manage plan and above. In Keystead, the Schedule E export is on every plan, because tax-ready books are the point of the product, not an upsell.
What it actually costs
Stessa: the Essentials plan is free. The Manage plan is $12/month billed annually ($15 monthly) and adds the Schedule E report, maintenance tracking, and legal forms. The Pro plan is $28/month billed annually ($35 monthly) and unlocks advanced reports, budgeting, and unlimited receipt scanning. All plans support unlimited properties.
Keystead: $29/month for up to 10 units, $79/month for up to 50, custom above that. Every plan includes the AI lease parser, Plaid bank feeds with automatic rent matching, the bank-rules engine, Schedule E export, work orders, and unlimited reports. There's a 14-day free trial with no credit card required — so the honest move is to run both for a week with one property and see which one leaves you less to do.
Common questions
Is Keystead a free Stessa alternative?+
No, and we won't pretend otherwise. Stessa's Essentials plan is genuinely free and genuinely useful. Keystead starts at $29/month for up to 10 units. The trade: Keystead's AI reads your leases for you, matches incoming rent to tenants automatically, and applies QuickBooks-style bank rules so your books close themselves. If your time is worth more than a few dollars an hour, the math usually favors automation — but if free is the requirement, Stessa is a fine choice.
What does Keystead do that Stessa doesn't?+
Three big things. First, AI lease parsing: drop a scanned PDF and every term — tenants, rent, deposit, dates, late fees, key clauses — is extracted with a confidence score and a citation back to the document. Second, automatic rent matching: incoming bank transactions are matched to the right tenant by amount, name, and your custom rules. Third, a real bank-rules engine with transfer detection, so recurring expenses categorize themselves the way they do in QuickBooks.
What is Stessa better at than Keystead?+
Honestly: price (the Essentials plan is free), built-in landlord banking with interest on cash balances, and the leasing side — vacancy marketing with Zillow syndication, tenant applications, and screening. If those are your priorities, Stessa deserves a look. Keystead is built for the accounting and operations side: books, rent, taxes, and maintenance.
Can I switch from Stessa to Keystead?+
Yes. Stessa supports full data export on all plans, and Keystead's setup takes about 10 minutes: add your properties (we auto-fill details from public records), upload your lease PDFs (AI extracts the terms), and connect your bank through Plaid. Most landlords are fully migrated within an afternoon.
Does Keystead include a Schedule E report like Stessa's paid plans?+
Yes — on every plan, including during the free trial. The Schedule E export maps each expense category to its IRS line item (insurance to line 7, mortgage interest to line 12, repairs to line 14, taxes to line 16, utilities to line 17). Keystead's founder is a CPA, and the report is designed to be handed directly to your accountant.
Try the version where the books close themselves.
Upload one lease and connect one bank account. If Keystead doesn't save you an hour in the first week, stay on Stessa — no hard feelings.
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