Gabe Winkler

Gabe Winkler

Sales Person

Gabe grew up in Kailua-­Kona and watched the town grow from a sleepy fishing town with stop light into the growing community it is today. He graduated from Konawaena High School in Kealekekua and then graduated from college in Washington State. After their first child was born in 2004, Gabe and his wife moved back to Hawaii to be close to family and raise their growing family in Hawaii.
Gabe’s main focus is to listen to clients and help them achieve their goals. Gabe understands the unique possibilities and challenges that come with transitioning in and out of island life and is ready to help you. He enjoys working with clients and with his vast knowledge of real estate gives valuable advice whether you are considering buying or listing property.
Gabe Winkler R(S) has worked in real estate for over fifteen years. Gabe started in real estate as an appraiser, valuing various residential and commercial properties in Hawaii. Since becoming a Real Estate Agent in 2013, Gabe has been able to utilize his knowledge of real estate to assist both buyers and sellers. He is also an active member of the Hawaii Association of REALTORS® and the National Association of REALTORS®.
As a long-time resident of Hawaii, he is very knowledgeable about the many unique communities around the Big Island. He enjoys working with first-time home buyers as well as astute investors working on a 1031 exchange with a tight deadline. Gabe stays informed with the current market trends regarding along with financing options, as they all relate to the real estate market. Gabe’s top priority is putting the needs of the customers first and providing excellent service with aloha.

​In his spare time, Gabe enjoys surfing the various surf spots on the Kona coast. Another pastime he enjoys is ultimate frisbee and is active with the local frisbee community in weekly pick­up games in Kona. He is a licensed private pilot and regularly flies around the islands for inter-­island business and family trips. He enjoys playing music and leads a worship team at a local church.

Easy transaction, closed in 45 days, service after the sale, nice guy, from Kailua-Kona, honest, kind, trustworthy, quick to respond to emails, quick to respond to phone calls.

— Michael A.


Gabe was instrumental in getting my house sold. Not being local to the house he handled all aspects of preparing the home, staging, and orchestrating contractors to take care of repairs negotiated in the sale.

— Ben H.


Gabe was a huge gift to our Kona home search! He listened closely, searched diligently, and negotiated wisely. He has my highest recommendation for anyone looking to purchase a home or property in the Kailua Kona area.

— Frank T.

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Work With Gabe

His background in the appraisal business has been beneficial in helping clients understand the lending side of the business and negotiating the best price. He has a passion for helping people in real estate.