Time for Boomers to Play It Safe: Our 5 Safest Monthly Pay Dividend Stocks

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By Lee Jackson Updated Published
Time for Boomers to Play It Safe: Our 5 Safest Monthly Pay Dividend Stocks

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While many Baby Boomers have enjoyed a long bull market over the past 35 years, there is a point when income becomes more critical than stock appreciation. The reason is simple: those who leave their careers to enjoy a well-deserved retirement lose the benefits of a regular salary and their jobs, such as 401(k) matching and company-paid healthcare. In addition, many Baby Boomers use their retirement years to travel and enjoy the rewards they have worked hard to achieve throughout their lives. Choosing investments wisely is imperative, and at 24/7 Wall St., we continually seek the best ideas for Baby Boomers and retirees. With sticky inflation and prolonged interest rate pauses continuing through mid-2026, building a highly dependable monthly income stream provides an alternative to chasing concentrated growth index momentum.

A monthly check from your stock portfolio makes sense for most people with bills and expenses due every 30 days, especially in a world where prices are consistently rising. Items like mortgage payments, rent, utilities, cell phone and internet bills, trash collection, and even grocery bills are always due each month. A steady stream of monthly passive income can be a huge help in meeting those obligations. With macroeconomic pressures keeping daily cost-of-living metrics elevated, optimizing consistent income structures allows retirees to safely offset ongoing expenses with cash arrivals that match their monthly liabilities.

We screened our 24/7 Wall Street research database for quality companies rated Buy at major Wall Street firms that paid monthly dividends. Five seem like great ideas for Baby Boomer passive income-oriented investors seeking upside appreciation. Plus, by choosing among the safest prices in the monthly dividend arena, investors can sleep a little easier at night.

Why do we cover monthly dividend stocks?

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Since 1926, dividends have accounted for approximately 32% of the S&P 500’s total return, while capital appreciation has accounted for 68%. Therefore, sustainable dividend income and the potential for capital appreciation are essential to total return expectations. A study by Hartford Funds, in collaboration with Ned Davis Research, found that dividend stocks delivered an annualized return of 9.18% over the 50 years from 1973 to 2023. Over the same timeline, this was more than double the annualized return for non-payers (3.95%).

Agree Realty

Agree Realty (NYSE: ADC | ADC Price Prediction) is an $ 8+ billion industry leader in the acquisition and development of properties net-leased to retailers. This mid-cap stock offers a reliable dividend yield hovering in the 4.02% to 4.25% range alongside strong upside potential. Agree Realty is a publicly traded real estate investment trust (REIT) that acquires and develops properties net-leased to industry-leading, omnichannel retail tenants.

The company’s assets are held by, and all of its operations are conducted directly or indirectly through, the operating partnership of which the company is the sole general partner.

Agree Realty owns over 2,370 single-tenant retail properties leased to investment-grade retailers, including Walmart, Dollar General, and Home Depot. It has a strong dividend safety profile and an investment-grade balance sheet. Importantly, its diversified portfolio, with no tenant accounting for more than 8% of rent, and its focus on e-commerce-resistant sectors like grocery and home improvement, ensure resilience. Plus, for investors concerned with investment safety, its BBB+ credit rating and strong dividend coverage support its reliability.

Its portfolio comprises over 2,370 properties in 50 states, totaling approximately 48.8 million square feet of gross leasable area (GLA). The company’s portfolio has properties located in:

  • Texas
  • Ohio
  • Florida
  • Michigan
  • Illinois
  • North Carolina
  • New Jersey
  • Pennsylvania
  • California
  • New York
  • Georgia
  • Virginia
  • Connecticut
  • Wisconsin

Agree Realty tenants include these companies and more:

  • Walmart
  • Dollar General
  • Tractor Supply
  • Best Buy
  • Dollar Tree
  • TJX Companies
  • O’Reilly Auto Parts
  • CVS
  • Kroger
  • Lowe’s
  • Hobby Lobby
  • Burlington
  • Sherwin-Williams
  • Sunbelt Rentals
  • Wawa
  • Home Depot
  • TBC Corporation
  • Gerber Collision

Wells Fargo has an Overweight rating with an $83 target price.

Healthpeak Properties

This leading company invests in real estate in the healthcare industry, including senior housing, life sciences, and medical offices. Healthpeak Properties (NYSE: DOC) is a fully integrated REIT with a solid 6.97% dividend. The stock is recommended by Morningstar’s chief U.S. market strategist, who rates it a five-star stock trading at a discount to fair value with a very dependable yield.

The company acquires, develops, owns, leases, and manages healthcare real estate across the United States. It owns, operates, and develops real estate focused on healthcare discovery and delivery.

Healthpeak Properties segments include:

  • Lab
  • Outpatient medical
  • Continuing care retirement community (CCRC)

The Outpatient medical segment owns, operates, and develops outpatient medical facilities, hospitals, and laboratory facilities.

The lab segment properties contain laboratory and office space and are leased primarily to:

  • Biotechnology
  • Medical device and pharmaceutical companies
  • Scientific research institutions
  • Government agencies
  • Organizations involved in the life science industry

Its CCRC segment comprises a retirement community offering independent living, assisted living, memory care, and skilled nursing units, providing a continuum of care within an integrated campus.

Evercore ISI has an Outperform rating with a $19 target price.

Main Street Capital

Main Street Capital (NASDAQ: MAIN) has helped over 200 private companies grow or transition by providing flexible private equity and debt capital solutions. This stock is a favorite across Wall Street and comes with a baseline monthly dividend yield of 5.8%, which reaches closer to 7.6% on a trailing basis when accounting for regular supplemental payouts like the recent $0.30 per share distribution. Main Street Capital is a private equity firm that provides equity capital to lower-middle market companies. Unlike most of its peers, it has a strong record of supporting its regular monthly dividend through multiple cycles, including periods when many business development companies (BDCs) were forced to reset payouts. It holds much less debt than regulators allow, earning a BBB- investment-grade credit rating, and is one of the few monthly dividend stocks to earn a “Safe” Dividend Safety Score.

The firm also provides debt capital to middle-market companies for:

  • Acquisitions
  • Management buyouts
  • Growth financings
  • Recapitalizations
  • Refinancing

The firm seeks to partner with entrepreneurs, business owners, and management teams and generally provides “one-stop” financing options within its lower-middle-market portfolio.

Main Street Capital typically invests in lower-middle-market companies with annual revenues between $10 million and $150 million. The firm’s middle-market debt investments are in businesses generally larger than its lower middle-market portfolio companies. It also creates majority and minority equity.

Royal Bank of Canada has an Outperform rating and a $66 target price.

PennantPark Floating Rate

This BDC invests in middle-market companies in the United States. Often overlooked by Wall Street, PennantPark Floating Rate Capital Ltd. (NYSE: PFLT) offers a substantial 14.60% monthly dividend yield. It seeks to invest in floating-rate loans through private, thinly traded, or small-cap public middle-market companies. It should be noted that floating-rate loans provide some protection in higher-rate environments. The company ranks among the top monthly dividend stocks by expected total return.

It primarily invests in the United States, with limited exposure to non-U.S. companies. The fund typically invests between $2 million and $20 million.

The fund also invests in:

  • Equity securities
  • Preferred stock
  • Common stock
  • Warrants or options received in connection with debt investments or through direct investments

It primarily invests between $10 million and $50 million in senior secured loans and mezzanine debt. It seeks to invest in companies not rated by national rating agencies. The fund invests 30% in non-qualifying assets, such as:

  • Investments in public companies whose securities are not thinly traded or do not have a market capitalization of less than $250 million
  • Securities of middle-market companies located outside of the United States
  • High-yield bonds
  • Distressed debt
  • Private Equity
  • Securities of public companies that are not thinly traded
  • Investment companies as defined in the 1940 Act

Under normal conditions, the fund expects at least 80% of its net assets plus any borrowings for investment purposes to be invested in floating-rate loans and investments with similar economic characteristics, including cash equivalents invested in money market funds. It expects to represent 65% of its portfolio through senior secured loans.

Keefe, Bruyette & Woods has an Outperform rating with a $10 price target.

Balancing Fixed vs. Floating Yields for Inflation Protection

Not all monthly dividends are structured the same way, and a resilient retirement portfolio often requires a combination of defensive fixed assets and responsive credit instruments. Traditional equity structures like net-lease real estate investment trusts offer highly predictable, contractual rent profiles that serve as defensive anchors. Conversely, business development companies that hold floating-rate loans capture higher yields when macroeconomic interest benchmarks stay elevated. Combining these two models allows income-focused investors to hedge purchasing power against a prolonged rate pause while maintaining fixed capital safety.

Realty Income

This REIT invests in free-standing, single-tenant commercial properties. Realty Income (NYSE: O) is an ideal stock for growth and income investors seeking a safer contrarian idea for the rest of 2026, with a baseline monthly yield at 5.09%. It is considered the gold standard of monthly dividend stocks. Realty Income has been paying dividends since 1969 and has built a reputation as one of the more durable income stocks across market cycles.

The company acquires and manages freestanding commercial properties that generate rental income under long-term net-lease agreements with its commercial clients. It is engaged in a single business activity: leasing property to clients, generally on a net basis. This business activity spans various geographic boundaries and encompasses a range of property types and clients across multiple industries.

The company owns or holds interests in approximately 15,621 properties in all 50 states and:

  • The United Kingdom
  • France
  • Germany
  • Ireland
  • Italy
  • Portugal
  • Spain

With clients doing business in 89 industries, its property types include retail, industrial, gaming, and other types, such as agriculture and office. Its primary industry concentrations include:

  • Grocery stores
  • Convenience stores
  • Dollar stores
  • Drug stores
  • Home improvement stores
  • Restaurants
  • Quick service

Deutsche Bank has a Buy rating with a $69 target price.


Editor’s Note: This article has been revised to update baseline dividend yields and supplemental payout figures for Agree Realty, Main Street Capital, and Realty Income to reflect current financial reporting. The introductory market analysis and macroeconomic commentary have been altered to transition focus away from historical geopolitical events toward ongoing trends in inflation, index asset concentration, and prolonged elevated interest rates. Additionally, a new analytical section detailing the strategic application of blending fixed net-lease real estate assets with floating-rate private credit structures has been introduced to the core content.

 

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About the Author Lee Jackson →

Lee Jackson has covered Wall Street analysts' equity and debt research and equity strategy daily for 24/7 Wall St. since 2012. His broad and diverse career, which included a stint as the creative services director at the NBC affiliate in Austin, Texas, gives him unique insight into the financial industry and world.

Lee Jackson's journey in the financial industry spans over 30 years, with nearly two decades as an institutional equity salesperson at Bear Stearns, Lehman Brothers, and Morgan Stanley. His career was marked by his presence on the sell side during pivotal Wall Street events, from the dot.com rise and bubble to the Long Term Capital Management debacle, 9/11, and the Great Recession of 2008. This is a testament to his resilience and adaptability in the face of market volatility.

Lee Jackson’s practical financial industry experience, acquired from a career at some of the biggest banks and brokerage firms, is complemented by a lifetime of writing on various platforms. This unique combination allows him to shed light on the intricacies and workings of Wall Street in a way that only someone with deep insider experience and knowledge can. Moreover, his extensive network across Wall Street continues to provide direct access for him and 24/7 Wall St., a privilege few firms enjoy.

Since 2012, Jackson’s work for 24/7 Wall St. has been featured in Barron’s, Yahoo Finance, MarketWatch, Business Insider, TradingView, Real Money, The Street, Seeking Alpha, Benzinga, and other media outlets. He attended the prestigious Cranbrook Schools in Bloomfield Hills, Michigan, and has a degree in broadcasting from the Specs Howard School of Media Arts.

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