October’s Income Picks: 2 Stocks Yielding Over 4% That Have Raised Payouts for 25 Years

Income investors usually face a trade-off. Companies with the longest dividend-growth records tend to trade at premium prices that reduce their yields, while the highest yields often come from businesses that freeze or cut payouts the moment credit tightens. Finding a meaningful current yield and a multi-decade raise run in the same ticker is rarer than most portfolios suggest.

Federal Realty (NYSE:FRT) stands at the extreme end of that list with 59 consecutive years of annual dividend increases, the longest record in the REIT sector, and it still yields above 4%. Pair it with Realty Income (NYSE:O), the monthly payer that has accumulated raises for decades, and you get two NYSE-listed landlords that clear both bars at once.

Realty Income: A Monthly Payer Near Its 52-Week Low

A High-Yield Monthly Check With a Verified Raise Streak

Realty Income yields 6.05% with shares trading around $53.63 on Oct. 1, firmly in high-yield territory. The forward annualized dividend stands at $3.258 per share, paid in 12 monthly installments. The latest declaration lifted the monthly payout to 27.15 cents from 27.1 cents, which the company called as its 136th common stock monthly dividend increase.

The run holds up under examination. Through the second quarter, Realty Income had delivered 115 consecutive quarterly dividend increases, and as of the first quarter it had declared 670 consecutive monthly dividends. The payment record shows steady steps higher, from $0.2255 per month in early 2019 to 25.65 cents in early 2024 and today’s 27.15 cents. That translates into a retiree’s paycheck that arrives every month and grows in small, reliable increases.

Dividend Safety Check: Coverage, Cash Flow and Balance Sheet

Coverage is the first test, and Realty Income passes it well. Second-quarter adjusted funds from operations (AFFO, the REIT industry’s measure of recurring cash earnings) came in at $1.09 per share, up 3.8% year over year. Management raised full-year AFFO guidance to $4.44 to $4.45 per share, which puts the payout at roughly 73% of AFFO. That cushion lets the company retain cash for acquisitions while still raising the monthly check.

Free cash flow confirms the picture. The stock trades at 13.3 times free cash flow, a 7.52% free cash flow yield that exceeds the dividend yield. Occupancy held at 98.8%, so rent is flowing in from nearly the entire portfolio.

The company carries an ‘A’ Long-Term Issuer Default Rating with a Stable Outlook from Fitch. Net debt to annualized pro forma adjusted EBITDAre stood at 5.4x, debt-to-equity is 0.83 and the revolving credit facility was expanded to $5.5 billion. An A-rated borrower with that much liquidity can fund growth through volatile credit markets without putting the dividend on the table.

Bull Case for Income Investors

Realty Income is the scale leader in net-lease real estate, and it is using that scale to move beyond its retail roots. Industrial properties made up for 65% of new second-quarter income. Management raised its 2026 investment volume target to $10 billion at a 7.3% initial cash yield, built a credit investment platform with $5.2B in commitments, and formed a $6B hyperscale data center joint venture. It also announced a euro-denominated joint venture to expand its private capital platform. Second-quarter revenue rose 9.7% to $1.55B.

The recent decline has lifted the yield. Shares are down 6.42% year to date, including a loss of 12.6% over the past month and now sit near the 52-week low of $53.28, well below the 52-week high of $66.25. The average analyst price target is $67.26. When a well-covered monthly dividend meets a falling share price, the yield on each dollar invested rises.

One Risk to Track

Tenant credit is the soft spot. Non-investment-grade clients represent 65.7% of annualized base rent. Second-quarter GAAP EPS of $0.37 came in below expectations of $0.42, missing expectations by 12.47% because of impairments and credit loss provisions. AFFO coverage absorbed the hit, but a recession that pushes more weak tenants into default would slow the pace of future raises.

Federal Realty: The REIT Sector’s Longest Raise Streak

A Dividend King Yielding Above 4%

Federal Realty is a Dividend King that yields 4.29% based on its prior indicated annual rate of $4.52, with shares around $105.99 on Oct. 1. That figure downplays the forward picture. The board raised the quarterly dividend 3% to $1.16 per share from $1.13, lifting the forward annualized dividend to $4.64. The first check at the new rate is payable Oct. 15 to holders of record on October 1.

That increase extends the run to 59 consecutive years of annual dividend increases, the longest in the REIT sector and enough to make Federal Realty a verified Dividend King. The payment history backs it up: the quarterly dividend stood at 44 cents in 1999 and stepped higher every year since, moving through 66 cents in 2010, $1.05 in 2019 and $1.10 in 2025. That record survived the financial crisis and the pandemic without a pause.

Dividend Safety Check: Coverage, Cash Flow, and Balance Sheet

Federal Realty raised its 2026 Core FFO (funds from operations excluding one-time items) guidance to $7.48 to $7.56 per diluted share, representing 5.9% to 7.1% growth. That puts the payout at roughly 62% of Core FFO, the stronger coverage of the two names here. Second-quarter Core FFO grew 6.8% to $1.88 per share, so cash earnings are growing faster than the 3% raise.

Operating cash flow is backed by a healthier portfolio. The leased rate reached 96.1%, up 70 bps year over year, and second-quarter revenue climbed to $335.7 million from $311.5 million. Management guides comparable property operating income growth of 3.25% to 3.75%. On liquidity, Federal Realty expanded its revolving credit facility from $1.25 billion to $1.4 billion, with an accordion feature up to $2 billion.

Bull Case for Income Investors

Federal Realty owns coastal and urban mixed-use destinations. Properties such as Santana Row, Pike & Rose, Assembly Row, and CocoWalk serve higher-income consumers who keep spending when budgets tighten elsewhere. Tenants are paying up for that space. The company signed 124 comparable retail leases covering 819,273 sq ft at 15% cash rent spreads, and trailing 12-month leasing volume hit a record 2,796,064 sq ft. A deep residential-over-retail redevelopment pipeline adds another layer of future rent growth.

The stock trades at 22 times trailing earnings. Shares are up 7.03% year to date but slipped 9.43% over the past month. Analysts carry five Strong Buy ratings and nine Buy ratings against six Hold ratings, with an average price target of $132. If rent spreads hold near current levels, Core FFO growth should keep funding raises at or above the latest 3% pace.

One Risk to Track

Borrowing costs are climbing. Second-quarter interest expense rose to $50 million from $44.6 million a year earlier, and the near-term refinancing environment remains challenging. If rates stay elevated as older debt rolls over, higher interest costs would absorb part of the Core FFO growth that funds future raises.

Two Landlords, One Income Standard

Realty Income and Federal Realty reach the same destination from different directions. Realty Income brings the bigger yield. It also offers a monthly paycheck and AFFO coverage near 73%, while Federal Realty brings the REIT sector’s longest raise run at 59 years and a payout of roughly 62% of Core FFO. Both yield above 4%, both have raised their dividends for more than 25 years, and both just raised again, and for income portfolios built on checks that keep getting bigger, this pair sets the benchmark.

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