Lifestyle and Rural Sales

After decades of success in real estate leadership, Chris Flanagan has returned to what he loves most selling. With nearly 40 years of experience and an unmatched knowledge of the Selwyn market, Chris is back doing what he’s passionate about: helping clients achieve outstanding results through strategic advice and tailored solutions.

Having sold everything from lifestyle blocks to large-scale dairy farms across Selwyn and Canterbury, Chris is one of the most respected names in the region. He began his career at just 21 years old with Matson & Allan, later purchasing the business in 2000 and leading it for over two decades. In 2022, Chris successfully oversaw the company’s merger with Bayleys and now serves as a founding director of Bayleys Selwyn.

Now, with a highly professional sales team managing the day-to-day operations of the business, Chris is free to focus entirely on his clients. His hands-on approach, paired with decades of insight and local expertise, means sellers benefit from advice that’s not only practical but proven to get results.

Chris’s approach is simple: listen, understand, and deliver. His deep-rooted connection to the land, genuine communication style, and commitment to doing right by his clients make him a natural and trusted choice whether you’re a first-time lifestyle buyer, a long-time landowner, or looking to navigate succession planning.

Known for his integrity, good humour, and no-nonsense attitude, Chris is both a skilled negotiator and a calming presence throughout the sales process. He understands that selling property is more than a transaction it’s a big life moment and he’s here to make it successful, stress-free, and even enjoyable.

If you’re thinking of selling and want someone with unrivalled local knowledge, practical solutions, and a true passion for the job—Chris Flanagan is your man.

Chris Flanagan  - Trusted, experienced, and back doing what he does best.