About
About
Meet CHELSEA
Chelsea Dimin has spent over 20 years living and working on Maui, building a practice for clients who expect more than a good deal: discretion, foresight, and a strategy that extends well beyond a single sale. She advises buyers and sellers through the lens of legacy, lifestyle, and long-term wealth, treating each property as one piece of a larger portfolio.
In 2024, Chelsea ranked the #1 Compass Hawaii Agent by Sales Volume and #13 Statewide Across All Brokerages, per The Wall Street Journal and RealTrends. In 2023 she became the first female Realtor on Maui to list and sell a property over $30M, the island’s highest sale that year.
Chelsea works across Maui’s most sought-after communities, including Makena, Wailea, Kapalua, Paia, Haiku, Kaanapali, Kihei, Kula, and Lahaina, specializing in luxury estates, oceanfront homes, vacation properties, and investment opportunities. Clients can expect sharp negotiation, strategic marketing, and market insight built on nearly two decades of watching this island’s real estate move.
ROOTED IN WELLNESS, COMMUNITY, AND ISLAND LIVING
Before real estate, Chelsea built her career in digital media and advertising sales in Los Angeles, working with global brands including Apple, Universal Pictures, and Nissan. That world moved fast and demanded precision: reading an audience, positioning a message, executing under pressure. Those are the exact skills she now applies to every listing and every negotiation, and they are a large part of why her approach to marketing property looks different from the traditional real estate playbook.
When Chelsea moved to Maui, she didn’t set that discipline aside. She built a life around it instead. For more than 15 years she has taught Pilates, barre, and yoga, work that demands the same patience and precision as her professional career, just applied to the body instead of a brand. She also farms her own property in Haiku, tending a lychee orchard alongside avocado and citrus trees, a pursuit that runs on a timeline measured in seasons, not quarters. Farming has taught her that real value is built slowly and protected carefully, a principle she carries directly into how she guides clients through a purchase or sale.
Surfing at sunrise, a trail run before the heat sets in, an afternoon hike to a waterfall most visitors never find: this isn’t a lifestyle Chelsea markets alongside her real estate business, it’s the same one. Twenty years on this island have taught her which beach breaks work at low tide, which trails wash out after heavy rain, and which neighborhoods actually feel like home once the tourists leave. That’s the Maui she shares with her clients, because she isn’t selling a listing. She’s introducing you to a life she already lives.
ONE OF MAUI’S TOP LUXURY REAL ESTATE ADVISORS STRATEGY, LIFESTYLE & LUXURY REAL ESTATE EXPERTISE
Chelsea Dimin is one of Maui’s top-performing Realtors and a trusted luxury real estate advisor known for her record-breaking results, strategic marketing expertise, and deep connection to the island lifestyle. Ranked the #1 Compass Hawaii agent in sales volume in 2024, Chelsea combines high-level business experience with a grounded approach centered around wellness, community, and long-term wealth building through real estate.
SUCCESS STORIES
"We were looking to relocate to Maui and buy an ocean-view property with acreage. We successfully closed on a beautiful property within 2 months thanks to Chelsea’s expert negotiating skills and in-depth knowledge of the Maui market. She is truly one of the best realtors on Maui and has taken care of everyone that we referred to her. We are definitely happy clients."
Gabriella Lajoya
"I've known Chelsea for over 10 years, and I can say without hesitation that she's one of the best in the business. She's smart, honest, and incredibly knowledgeable about the Maui real estate market; the kind of expertise that only comes from years of genuine dedication to her clients and community.Beyond her expertise, Chelsea's energy and ambition set her apart. She's always staying ahead of the curve, embracing the latest technology to better serve her clients. If you're looking for a realtor who combines deep local knowledge with genuine drive and integrity, Chelsea is exactly who you want in your corner."
Ken Grodberg
"Chelsea has managed and rented our home in Kihei Maui for five years! She has done an exemplary job of keeping us posted for needed maintenance and been extremely helpful in finding excellent renters. We could not have this home without her help. She is always attentive and prompt in letting us know what needs done. We would highly recommend her for any real estate Or management needs you might have."
Becky Slayton
"Chelsea Dimin was wonderful in helping us find a residence in South Kihei on Maui. She stuck with us through several years of searching and found the perfect property for us. Chelsea’s knowledge and experience was invaluable in the purchase of our investment properties in South Kihei Maui. Her expertise in property management made our investment properties stress free. I would highly recommend Chelsea Dimin to anyone looking for a residence, investment property and property management on Maui, Hawaii. Thank you Chelsea !"
Bruce Zauft
"Chelsea has been such a pleasure to work with! She helped me find the perfect home for my grandmother. So perfect, we didn’t even look at any other places! She nailed it in the first go. The house checked off all the boxes I had asked for, I couldn’t believe it. It was exactly what we as a family were looking for, for my grandmother. The plantation style house is centrally located in Wailuku in a cozy tucked away neighborhood, yet still 5 minutes from the hospital. Best of all, my grandmother is so happy with the place! Chelsea is always available and quick to respond to any of our needs and questions which I really appreciate. Thanks again Chelsea for all your help!"
Becky Dosh
"Chelsea sold our beach house in Paia, and I still don’t know how she made it feel that easy. We were not local. This was our second home, so we were handling the whole sale from thousands of miles away, and she took care of every single detail like it was her own place. She went above and beyond in every way. I’m so grateful we had her in our corner in every regard. I cannot recommend her enough."
Angie Wisdom
"Let me preface this post by saying that I do not offer reviews of people or places except for the exceptional, and this is one of those.Chelsea Dimin has been our realtor for two purchases on Maui. The first was an investment property in the Kihei area, and the second was for our private residence in the Kula 200 area.Between the two, we investigated many properties. Chelsea had researched each and was thoroughly informed, so she was able to attend to any questions we had.Chelsea's expertise spans knowledge of Maui County rules, regulations, and requirements whether for investment, rental, residential, or agriculture property.The contracts that Chelsea drew up were concise and precise, and she handled any negotiations smoothly and smartly...to our advantage.Having worked with many realtors in a half dozen states throughout the years, I can say that Chelsea is the very best."
Jill Scott
"Chelsea found us the perfect spot in Haiku! With our hopes & dreams of finding acreage with 2 Homes, she literally made our dreams come true. As a new resident of Maui, Chelsea made the process seamless & fun! Her knowledge and expertise in the entire journey from recommending contractors, inspectors, mortgage assistance and banking truly made the entire experience painless and efficient. I would highly recommend Chelsea to anyone and everyone in search of real estate in Maui! She is a true professional and an expert in her field!"
Ary Schalick
"Very highly educated, very awesome Realtor® skills that took my treehouse of horror and turned it into a gem. I was a first-time buyer and a seller and she guided me every step of the way. Thank you so much."
Matthew M.
"Chelsea assisted us in selling our condo in October of 2021. Overall, Chelsea made our process painless and super easy. She guided us along every step of the way and was always in communication with us. Chelsea got us the best deal for our condo and we couldn’t have been happier with our selection in trusting her to sell our “first” home."
Alyssa M.
"If you are buying a property you absolutely need Chelsea by your side. She was fantastic from the beginning to the end of the process. Exceptional knowledge of the local market and clever negotiating skills set her apart. Buying property is stressful and Chelsea remained calm and very responsive throughout the process. Her advice was invaluable. Thank you, Chelsea."
Jai D.
"Chelsea Dimin provided exceptional service from the online and in-person house hunt to the final walk-through. She valued my time and ensured that we saw only properties of interest. She meticulously recorded details from each meeting with me and with the inspectors. I appreciated her timely responses and anticipation of my questions for the next steps. Her guidance and expertise proved invaluable. I could not have asked for a better experience."
Tom W.CHELSEA IN THE PRESS
CHELSEA’S NETWORK
Chelsea is part of an exceptional circle of industry-leading networks and influential communities that represent the highest level of collaboration, leadership, and luxury real estate expertise. These affiliations allow her to cultivate powerful relationships, stay connected to premier markets, and provide her clients with elevated opportunities and unmatched reach.
Chelsea Dimin gives clients access to exclusive Maui listings, including off-market and pre-market opportunities across the island’s top communities. With strong local connections and deep market insight, she helps you identify the right properties and navigate every step with confidence—from search to closing.
Whether acquiring a luxury oceanfront estate, securing a legacy property, or selling a high-value Maui home, Chelsea Dimin provides a highly strategic, advisory-driven approach tailored to each client’s goals. With deep market insight, strong negotiation expertise, and a long-term perspective on wealth building, she helps clients make confident decisions in Maui’s most competitive luxury and investment markets—delivering discretion, clarity, and results at every stage of the process.
