Meet Kelsey Charles: The Hawaii Real Estate Agent Redefining the Industry

At age 18, alone with no family, friends, job, money, or even a place to live, Kelsey Charles bought a one-way ticket to Hawaii with nothing but a plan to attend college in the most expensive state in the union. Today, she’s a highly successful real estate businessperson and earned the Rookie of the Year award from the island’s largest real estate brokerage firm in her first year. What happened in between? This is the story of how she went from struggling to survive to Hawaii’s top-selling millennial Realtor, founding The Kelsey Charles Team with her husband, and generating $55 million in sales volume in less than three years.

Making Ends Meet

For Kelsey, life hasn’t always been easy. Originally from Janesville, Wisconsin, she fell into opioid dependence at the age of 12, but has never been shy of hard, difficult work. She graduated high school with honors, despite needing to skip school often to make money so her mom could pay rent. She began going through opioid replacement therapy to recover from her dependence, and she beat addiction after meeting her husband and starting a family. Now, she has been clean for over a decade.

She moved to Hawaii for school at the age of 18 after being awarded a scholarship at Hawaii Pacific University. There, she met her husband, got married, and dropped out of college to help raise their newborn child. During her second pregnancy, money was tight. “It was like Soviet-style poverty,” Kelsey remembers, “making bread out of flour and water – couldn’t afford yeast – for a few nights.” She then started driving Uber hoping to make at least $5 per day just so her family could eat. Additionally, she was also suffering with hyperemesis gravidarum (severe nausea and vomiting), which further complicated life.

Her husband had served in the Navy for nearly 10 years before receiving a medical retirement, so Kelsey had a front-row seat to the needs of the military community in Hawaii. That’s what drove her decision to get a real estate license after she had her second child. She knew it was a risk.

“The vast majority of people leave the real estate profession in their first few years and never really make a sustainable income, but I knew that I was just going to find a way to do it,” she explained. So, she enrolled in a pre-licensing course, going on to say, “I just gambled on myself, that hopefully I could figure it out.”

Real Estate Prowess

As Kelsey got started in the real estate world in early 2019, she did more than just “figure it out”. In fact, she thrived in her new career. The Real Broker, LLC top-seller created a Facebook page, Buying Home, Hawaii, and her own lead generation system. This helped her sell $12 million in her first year as an agent, $25 million her second, and $55 million cumulatively thus far.

“I basically helped people buy houses using their VA loan. It allows them to buy a million dollar house zero down. Military families often do not know the advantage they have in this brutal market. Many local families unfortunately never save up enough to afford their needed down payment,” she explains “and Hawaii has the lowest property taxes in the nation, which makes it a prime investment.”

Today, Ms. Charles’ ideal clients are entrepreneurs who own multiple properties and want to buy in Oahu. She aims to offer real estate with heart, spending time getting to know clients before advising them, stating,“I want to show up as your friend helping you buy a house.” This approach works.

Working with Real Broker, LLC, she is their #1 agent in Hawaii and in their top 10 of all agents nationally. Although a relatively new publicly-traded company, Real Broker, LLC operates in 40 out of 50 states plus DC and Canada and is continuing its binational expansion. An agent who is licensed in multiple states can theoretically associate their license with the brokerage without incurring redundant fees. With a $12,000 cap and 85/15% split, the brokerage offers other lucrative compensation packages for producing agents in the form of a competitive revenue share and agent equity program that exceeds more established firms.

Kelsey believes the hardships of her early life are what forged her success in the real estate business today and welcomes agents, whether newly-licensed or seasoned veterans, to set themselves and their families up for future success, despite personal challenges.

“There are so many transferable skills learned when you have to work hard and hustle. You learn to be resilient and put in the effort to be successful,” stated Charles. “I want people to know there’s hope out there, especially if they were an addict … you can still have an amazing life. You do not need to be a statistic.”

For 2022, Kelsey’s goals are to earn her broker’s license, diversify her clientele, help grow Real Broker, LLC, and help with Oahu’s severe housing shortage by learning to invest in and repair dilapidated properties while helping other investors and agents do the same.

About Kelsey Charles, CRS, MRP, CLHMS

Kelsey Charles works with veterans and second-home clients to buy and sell homes in Hawaii. Since becoming a real estate agent in 2019, she has sold over $55 million worth of lucrative real estate investments. For more please visit her website,

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