David Highland is one of Australia’s most respected voices in real estate, with more than 30 years of industry experience and a track record of leadership, innovation, and expansion. As the Founder and CEO of Highland Group, David has transformed the company from a boutique agency of six into a powerhouse team of more than 220 professionals spanning residential and rural sales, commercial leasing and acquisitions, property management, finance, marketing, Calico Marina and marine brokerage.

Since establishing Highland in 2007, David has grown the business into a thriving independent network of seven offices across the East Coast, with a presence in key markets including Sydney’s Sutherland Shire, Double Bay, the Inner West, Southern Highlands, and the Gold Coast. Under his leadership, the group now transacts over $2.5 billion in sales annually.

David is widely recognised for his strategic foresight, expanding the Highland footprint in partnership with some of the industry’s most established names. His leadership is marked by a commitment to excellence and an ability to build high-performing teams that consistently deliver market-leading results. His entrepreneurial drive extends beyond property.

In 2023, David launched Calico Marina in Cronulla, offering world-class facilities and establishing a new lifestyle destination with the launch of Pippis by The Grounds. This was followed in 2024 by Highland Marine, a game-changing offering in the marine sales sector.

David’s distinctive approach, combining strategic growth with authenticity, resilience, and an unwavering focus on client outcomes has earned him numerous accolades. He has been consistently ranked among the top agents in the country and is a sought-after commentator and thought leader on real estate trends, market performance, leadership, and business innovation.

Awards

- REB Principal of the Year 2026

- REB Sales Office of the Year – Metropolitan Highland Cronulla 2026

- REINSW Winner Residential Salesperson of the Year Award 2022 - David Highland

- REB Top 4 Agent in Australia 2022

- REB Top 5 Agent in NSW 2022

- REB Winner Australian Excellence Award 2021

- REB Winner Boutique Independent Office of the Year - 2020 & 2021

- REB Winner Principal of the Year - Metropolitan 2019 & 2021

- REB Top 4 Agent in Australia 2021

- REB Top 7 Agent in Australia 2020

- REINSW Winner Real Estate Agency – Large 2018, 2019 & 2020

- REB Top 5 Sales Office Australia - 2019

- REB Top 6 Agent in Australia 2019

- REINSW Winner Residential Salesperson of the Year 2018

- REB Top 7 Agent in Australia 2018

- REB Top 9 Agent in Australia 2017