Stessa is a Rental property financial management by Stessa (a Roofstock company). This profile pulls together Stessa's ratings across the major review sites, its company and funding details, leadership, features, pricing, and the latest news, with every external source cited at the bottom.
About Stessa (a Roofstock company)
Stessa is a financial tracking and management platform designed for residential real estate investors and landlords. Founded in 2016 in San Francisco and acquired by Roofstock in 2022, Stessa provides a free core product that lets landlords track rental income, expenses, and property performance with automatic transaction categorization from linked bank accounts. The platform generates tax-ready financial reports and Schedule E worksheets, making it popular with landlords who manage 1-50 properties without a bookkeeper. Stessa Pro (paid tier) adds features like rent collection, tenant screening, and lease tracking. Stessa's free tier is among the most capable in the property management category and drives most of its user acquisition.
| Category | Rental property financial management |
| Company | Stessa (a Roofstock company) |
| Founded | 2016 |
| Headquarters | San Francisco, California, US |
| Industry | Financial Technology · Real Estate |
| Team size | ~50-100 |
| Ownership | Subsidiary of Roofstock (acquired 2022) |
| Founder / CEO | Jonah Schwartz and Edward Zimble |
| Specialties | Rental property accounting, income/expense tracking, tax reporting, real estate portfolio management |
| Website | stessa.com |
Find Stessa on: Crunchbase · LinkedIn · G2 · Capterra
Stessa ratings across the web
Aggregated from the major review platforms. Each links to the source.
Rating breakdown
Per-category scores from G2 and Capterra, ~500 reviews, 2025-2026.
Who uses Stessa
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What people say about Stessa
Our synthesis across ~500 G2 and Capterra reviews, 2025-2026. No fabricated quotes, this is the consistent pattern across reviews and third-party analyses.
Most praised
- Best free rental property accounting tool available
- Automatic transaction categorization saves significant bookkeeping time
- Tax-ready reports (Schedule E) are well-implemented
- Clean interface that non-accounting landlords can navigate
Most cited complaints
- Free tier lacks rent collection and tenant management
- Not suitable for professional PMCs managing third-party properties
- Support can be slow for non-premium users
- Limited integration ecosystem
What we found testing it
What's great
- Free core accounting with automated bank feeds, expense categorization, and Schedule E-ready tax reports for the whole portfolio
- Built by real estate investors specifically for buy-and-hold rental portfolios, not adapted from generic accounting software
- Backed by Roofstock, adds a data pipeline into rental market benchmarks that pure accounting tools do not offer
Watch-outs
- G2 review base is thin at 12 reviews, the smallest sample in this list, so treat the rating as directional rather than definitive
- No trust accounting or owner-of-record separation, this is single-owner portfolio accounting, not third-party property management
- No tenant portal or lease management, purely an accounting and reporting layer that pairs with a separate PM tool if you need one
Stessa funding & ownership
| Round | Amount | Date | Lead investor |
|---|---|---|---|
| Series A | ~$10M | 2019 | Undisclosed |
| Acquisition by Roofstock | Undisclosed | 2022 | Roofstock |
Stable as a Roofstock subsidiary. Stessa's free tier is a strong user acquisition engine for the Roofstock ecosystem. The financial tools are well-executed for the target (DIY landlords 1-50 units).
Stessa features & integrations
Feature availability
| Feature | Status |
|---|---|
| Free tier | yes unlimited properties |
| Owner 1099 | No |
| Rent roll | • basic |
| Tenant portal | No |
| Trust accounting | ✗ single-owner only |
Security & compliance
| Standard | Availability |
|---|---|
| GDPR | Yes |
| HIPAA | N/A |
| SOC 2 Type II | Yes |
| SSO / SAML | No (Google login) |
Integrations: Bank account sync (Plaid), Mortgage accounts, Roofstock marketplace, QuickBooks (limited export), and Tax software exports.
Stessa leadership
Stessa pricing
| Plan | Price | Best for |
|---|---|---|
| Free | $0/mo | Landlords who want expense tracking and tax reports only |
| Pro | $20/mo or $12/mo (annual) | Landlords who also want rent collection and screening |
The catch: Stessa's core product is genuinely free with no unit limits. Stessa Pro adds rent collection, tenant screening, and premium support for $20/month or $12/month (billed annually). For most individual landlords, the free tier covers the core use case.
Stessa alternatives & where it appears
Featured in our guides
Stessa product changelog
What Stessa has actually shipped, summarized from its own release notes and dated. Not auto-generated, updated as part of our freshness checks.
- October 1, 2025
- February 1, 2025
Latest Stessa news
Auto-pulled from Google News, refreshed on each deploy. Headlines link to the source.
- Stessa-ResiClub Real Estate Investor Survey Q4 2025 results, as told by 9 charts - ResiClubTue, 18 Nov 2025
- Stessa, a Roofstock Company, Launches Best Rate Guaranteed DSCR Loan Quotes Through New Partnership with LendingOne - Business WireTue, 06 Jan 2026
- Stessa Review: Free Accounting Software For Landlords - The College InvestorWed, 03 Dec 2025
- JLL launches commercial partnership and strategic investment in SFR proptech leader Roofstock - JLLTue, 02 Mar 2021
- One of the world's biggest real-estate firms is betting that single-family rentals will continue to boom - Business InsiderWed, 10 Mar 2021
- The housing market is being transformed by lifestyle delays—here’s how - ResiClubSat, 24 May 2025
Stessa FAQs
Does Stessa replace a bookkeeper for rental properties?
For simple portfolios (1-20 single-family rentals), Stessa can significantly reduce bookkeeping work. For complex portfolios with multiple LLCs or commercial properties, a bookkeeper is still recommended.
Does Stessa handle multiple LLCs or entities?
Stessa supports multiple properties and can track different entities. Full multi-entity LLC accounting with entity-level reporting requires the Pro plan.
Is Stessa useful for short-term rentals (Airbnb/VRBO)?
Stessa works for STR financial tracking and can sync with STR platform payouts, but lacks STR-specific features like dynamic pricing. Most STR operators use it alongside dedicated STR tools.
Sources
Every external figure on this page traces to a public source, last collected on the dates shown.
- Stessa website — Product and pricing overview (accessed 2026-09-02)
- G2 Stessa reviews — User reviews (accessed 2026-09-02)