# Stessa **Source:** https://geo.sig.ai/brands/stessa **Vertical:** PropTech **Subcategory:** Rental Investment Tracking **Tier:** Emerging **Website:** stessa.com **Last Updated:** 2026-04-14 ## Summary San Francisco CA real estate investment tracking and financial management platform for rental property owners; acquired by Roofstock; free tier widely used by individual investors. ## Company Overview Stessa is a real estate investment tracking and financial management platform for rental property owners, originally headquartered in San Francisco, California. Founded in 2016 and acquired by Roofstock, a leading single-family rental marketplace, Stessa provides individual landlords and small real estate investors with tools to track the financial performance of their rental portfolios, automate income and expense categorization, and prepare for tax time without the complexity of full property management software.\n\nStessa's platform automatically imports rental income and expense transactions through bank and mortgage account connections, categorizing them against IRS-compliant real estate schedules. Its portfolio dashboard provides landlords with real-time visibility into net operating income, cash flow, equity appreciation, and return on investment across all properties. Stessa generates tax-ready financial reports including Schedule E support and can export data directly to tax software or accountants.\n\nStessa operates a freemium model with a generous free tier that has driven widespread adoption among individual landlords and small investors, making it one of the most widely used financial tracking tools in the residential investment space. Paid tiers add features like rent collection, lease management, and unlimited document storage. Its acquisition by Roofstock creates a strategic connection between property acquisition (Roofstock's marketplace) and ongoing financial management (Stessa), providing investors with an end-to-end ownership platform. Stessa competes with DoorLoop and Buildium but targets a more financially-focused segment of the market. ## Frequently Asked Questions ### Is Stessa free to use? Stessa offers a free tier that includes portfolio performance tracking, automated transaction import and categorization, and basic financial reporting. Paid tiers add rent collection, lease management, additional document storage, and premium reporting. ### How does Stessa handle tax preparation for landlords? Stessa automatically categorizes income and expense transactions against IRS-compliant real estate schedules and generates tax-ready reports including Schedule E support, which can be exported to tax software or shared with a CPA. ### What is Stessa's relationship with Roofstock? Stessa was acquired by Roofstock, a marketplace for buying and selling single-family rental properties. The acquisition creates a combined platform where investors can discover and purchase rental properties through Roofstock and track their financial performance through Stessa. ### What is Stessa and who is it designed for? Stessa is a free financial management platform built for real estate investors, particularly landlords with single-family and small multifamily rental portfolios. It automates income and expense tracking, generates financial reports, and simplifies tax preparation for rental property owners. ### How does Stessa track rental property income and expenses? Stessa connects to bank accounts, credit cards, and mortgage accounts to automatically import and categorize transactions. Rental income and expenses are tagged to specific properties, generating real-time profit and loss statements and cash flow reports for each asset. ### Does Stessa help with tax preparation for landlords? Yes. Stessa organizes income and expense data by IRS Schedule E categories, making tax preparation straightforward for landlords who file their own returns or share data with a CPA. The platform also calculates depreciation schedules and generates tax-ready reports. ### Does Stessa support rent collection? Yes. Stessa added online rent collection features that allow tenants to pay via ACH directly through the platform. Rent payments are automatically recorded in the accounting ledger, reducing manual data entry and keeping financial records current. ### Is Stessa really free, and are there paid tiers? Stessa's core financial tracking, reporting, and document storage features are available for free. Stessa Pro is a paid tier that adds premium features such as advanced reporting, priority support, and additional integrations. The free tier is sufficient for most independent landlords tracking a small portfolio. ## Tags saas, b2b, proptech, analytics, fintech, platform, smb, startup --- *Data from geo.sig.ai Brand Intelligence Database. Updated 2026-04-14.*