Meet Wall Street's Safest Ultra-High-Yield Dividend Stocks: 2 Companies That Have Raised Their Payouts a Combined 216 Times Since 1994

With more than 5,000 publicly traded companies and over 4,600 exchange-traded funds (ETFs) to choose from on U.S. exchanges, there is no shortage of ways to make money on Wall Street. But few strategies have proven more fruitful for investors than buying and holding high-quality dividend stocks.

Companies that pay a regular dividend to investors typically share several characteristics. For instance, they're often profitable on a recurring basis, time-tested, and capable of providing investors with transparent long-term growth guidance.

However, the most important aspect of income stocks might just be their outperformance, relative to non-payers. In "The Power of Dividends: Past, Present, and Future," analysts at Hartford Funds, in collaboration with Ned Davis Research, found that dividend payers more than doubled the average annual return of non-payers over 51 years (1973-2024): 9.2% annualized vs. 4.31% annualized. Additionally, income stocks were less volatile than non-payers and the benchmark S&P 500.

Image source: Getty Images.

But this data doesn't imply that you can throw a dart at the business section of the daily newspaper and land a winner. Not all dividend stocks are created equally, which is especially true for income stocks in the ultra-high-yielding space -- those with yields four or more times greater than the yield of the S&P 500. Ultra-high-yield stocks can sometimes be more trouble than they're worth.

Yet, with proper vetting, elite ultra-high-yield dividend stocks can be found.

What follows are the two safest ultra-high-yielding stocks on Wall Street, which, combined, have raised their payouts 216 times since their respective public debuts.

Enterprise Products Partners: 5.8% yield

When it comes to safe, supercharged dividends, arguably no company has delivered for investors quite like energy titan Enterprise Products Partners (NYSE: EPD). Although Enterprise has increased its distribution for 27 consecutive years, it's raised its payout on 82 occasions since going public in late July 1998, returning $62 billion in the process. Its current yield of 5.8% is more than quadruple the average yield of 1.23% for S&P 500 companies.

Most oil and gas stocks tend to move in lockstep with the spot price of energy commodities and can be prone to wild margin/profit swings. But Enterprise Products Partners isn't "most oil and gas stocks."

As of February, it's one of America's foremost integrated energy midstream companies. It oversees more than 50,000 miles of transmission pipeline, can store over 300 million barrels of petroleum liquids, and has north of two dozen fractionators. It's the ultimate energy middleman.

Aside from this operating diversity, the true beauty of Enterprise's business is that a majority of its contracts with upstream drillers are fixed-fee. Fixed-fee contracts remove the effects of spot-price volatility and inflation from the equation, leading to highly predictable operating cash flow year after year.

Cash flow transparency is vital to Enterprise Products Partners' success, with the company spending billions on organic projects (many of which are designed to boost its exposure to natural gas liquids), and occasionally making acquisitions to expand its reach.

Another factor working in Enterprise's favor is the tight global crude oil supply in the wake of the Iran war. With crude oil prices skyrocketing, domestic producers are being incentivized to boost their output. This should lead to additional opportunities for Enterprise Products Partners to secure long-term, fixed-fee contracts.

Grocery stores play a key role in Realty Income's commercial real estate portfolio. Image source: Getty Images.

Realty Income: 5.2% yield

The other public company that can generate super-safe, high-octane dividends for patient income seekers is retail real estate investment trust (REIT), Realty Income (NYSE: O).

How safe is Realty Income's payout? For starters, it holds the registered trademark as "The Monthly Dividend Company®." Realty Income has been doling out monthly dividends since going public in 1994. More impressively, the company has raised its monthly payout (drum roll)... 134 times! When combined with Enterprise Products Partners, we're talking about 216 dividend increases between the two companies since 1994.

One reason Realty Income is such a phenomenal company is that it leases to predominantly stand-alone, brand-name businesses. We're talking about well-known grocery chains, dollar stores, convenience stores, drug stores, and automotive service shops that draw customer traffic in any economic climate. With a large percentage of its commercial real estate portfolio resistant to recessions and e-commerce pressure, rental delinquencies are rarely, if ever, an issue.

Realty Income's management team also deserves credit for its lease-vetting process. The company closed out 2025 with an occupancy rate of 98.9%, which is 450 basis points above the median occupancy rate for S&P 500 REITs since 2000.

In addition to careful vetting during the leasing process, Realty Income relies on triple-net leases to stabilize its cash flow and minimize surprises. Whereas typical rental agreements require the landlord to cover property taxes, insurance, and maintenance/repairs, triple-net leases require the tenant to bear the responsibility for all site expenses. This means no surprises for Realty Income -- just steady and predictable operating cash flow.

The final advantage for Realty Income is that it's historically inexpensive. It's currently trading at a little over 13 times forecast cash flow for 2027, marking a 15% discount to its average price-to-cash-flow multiple over the last half-decade.

Sean Williams has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Realty Income. The Motley Fool recommends Enterprise Products Partners. The Motley Fool has a disclosure policy.