One of the most appealing aspects of owning S&P/ASX 300 Index (ASX: XKO) shares is that they can provide a combination of dividends and long-term growth.
Annual dividend growth is certainly not a guarantee for investors, but the two businesses I'm going to highlight have increased their payout on an extremely consistent basis.
I like to look at dividend payments because a rising payout can suggest multiple things, including confidence in the board's outlook and an increase in the business' underlying value. I think the two ASX 300 shares below are ones to watch with that in mind.
Charter Hall Group (ASX: CHC)
Charter Hall describes itself as a leading fully integrated diversified property investment and funds management group. It manages a diverse portfolio of high-quality properties across its core sectors of office, industrial and logistics, retail, and social infrastructure.
The company has increased its annual payout every year since the GFC, meaning it has one of the most consistent records on the ASX.
Charter Hall has steadily expanded its funds under management (FUM) over the long term to reach $84.3 billion at June 2025.
In early FY26, it announced the launch of the $2.5 billion Charter Hall Convenience Retail Fund, having secured $1.8 billion in equity commitments. It also expanded its constitutional client base, securing the mandate to manage the $2.1 billion Australian direct property portfolio of the Challenger Ltd (ASX: CGF) Life division.
I think the 2025 RBA rate cuts could help increase property values and drive further demand (by investors and tenants alike) for commercial property.
The ASX 300 share is expecting to grow its operating earnings per security (EPS) by 10.6% in FY26 and deliver distribution growth of 6%. At the time of writing, that would mean a grossed-up dividend yield of more than 3%, including franking credits.
Pinnacle Investment Management Group Ltd (ASX: PNI)
Pinnacle is an important business in the investment world. It helps highly rated fund managers grow their business, enabling them to focus on investing and leaving behind-the-scenes work to others.
The ASX 300 share takes sizeable minority stakes in the fund management businesses, which have typically gone on to become impressive investments for Pinnacle.
Looking at the dividends, aside from the COVID-impacted 2020 year (when it maintained its payout), Pinnacle has increased its annual payout each year since 2018.
Pinnacle delivered an enormous dividend increase of more than 40% in FY25, and I believe the business could provide rising payouts in the coming years, particularly if asset markets continue delivering positive returns.
At the time of writing, the company's FY25 payout translates into a grossed-up dividend yield of approximately 4.5%, including franking credits.
