A $100 monthly deposit may not sound like a big deal, but receiving that amount without paying tax on it could make a meaningful difference over time. It could cover your utility bill, support your grocery budget, or be reinvested to build an even larger income stream.
A Tax-Free Savings Account (TFSA) makes this possible because eligible dividends and capital gains earned inside it are generally sheltered from tax. But the real task is finding dependable investments that pay consistent dividends every month.
In this article, I’ll highlight two monthly income stocks that could help TFSA investors work toward earning $100 in tax-free cash each month.
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H&R REIT stock
The first monthly income option that could help turn a TFSA into a steady cash source is H&R Real Estate Investment Trust (TSX:HR.UN).
H&R owns residential, industrial, office, and retail properties across Canada and the United States. Its stock currently trades at $11.20 per unit with a market cap of about $3 billion. It pays monthly distributions and offers a 5.4% annualized dividend yield. Its units have climbed about 9% so far in 2026.
Over the last few quarters, H&R has also made meaningful progress in strengthening its balance sheet. During the first quarter of 2026, it completed about $1.5 billion in retail and office asset sales. The net proceeds were mainly used to repay debt.
As a result, the real estate investment trust’s (REIT) debt to total assets fell to 31.7% from 38.4% at the end of 2025. Similarly, its proportionate debt to adjusted EBITDA (earnings before interest, taxes, depreciation, and amortization) fell to 7 times from 9.3 times.
Although H&R’s first-quarter funds from operations (FFO) declined to $76.3 million due partly to asset sales, its adjusted FFO payout ratio still remained manageable at 64.1%. The company also expects lower financing costs after its debt repayments.
At the same time, the REIT is simplifying its portfolio around residential and industrial properties. These moves could support more efficient operations, making H&R an attractive monthly income stock for TFSA investors right now.
Sienna Senior Living stock
For investors who want a monthly tax-free income backed by growing demand for senior housing, Sienna Senior Living (TSX:SIA) could be another appealing choice.
Sienna operates retirement residences and long-term care communities in Canada. After rallying by 26% over the last 12 months, SIA stock currently trades at $22.87 per share with a market cap of $2.5 billion. It offers a 4.1% annualized dividend yield at the current price.
Despite interest rate and macroeconomic uncertainties, Sienna’s first-quarter results showed strong operating momentum. Its revenue on a proportionate basis rose 17.3% year-over-year (YoY) to $286.3 million with the help of acquisitions, higher retirement occupancy, rental rate increases, and stronger care revenue.
As a result, its adjusted FFO jumped 45.1% YoY to $35.1 million, while the payout ratio improved to 68.5% from 86%. Adding to the optimism, the company’s retirement same-property occupancy reached 94.7%, helping its same-property net operating income rise 7.9% YoY.
Meanwhile, Sienna is also expanding its platform. In June, the company completed the $41 million acquisition of Rockland Manor, adding a retirement residence that was about 98% occupied. It also announced plans for a new 256-bed long-term care redevelopment in Mississauga with an estimated cost of $125 million, adding to its long-term growth pipeline.
Supported by rising demand for senior housing, improving occupancy, strategic acquisitions, and ongoing redevelopment projects, Sienna offers a solid mix of dependable monthly income and long-term growth potential.
| COMPANY | RECENT PRICE | NUMBER OF SHARES | INVESTMENT | DIVIDEND PER SHARE | MONTHLY PAYOUT | DIVIDEND FREQUENCY |
| H&R REIT | $11.20 | 1,134 | $12,700 | $0.05 | $56.7 | Monthly |
| Sienna Senior Living | $22.87 | 555 | $12,700 | $0.078 | $43.3 | Monthly |
| TOTAL | $25,400 | $100.01 | ||||
| Prices as of July 22, 2026 |
The math to generate $100 a month in TFSA income
The math is simpler than it may seem. To earn $100 each month, you need $1,200 in annual dividend income. A portfolio split evenly between H&R REIT and Sienna would offer an average yield of about 4.8% based on their current yields.
That means an investment of roughly $25,400 could generate close to $1,200 per year. Reinvesting those monthly payments could also help you reach a higher income target.
