Wailea, HI Luxury Homes For Sale

Discover the luxury homes for sale in the prestigious area of Wailea, HI with Chelsea Dimin. Our experienced agent can help you find the perfect home that meets your luxury living expectations. Start your search with us today and let us assist you in finding the luxury property that suits your needs and desires.

Luxury Homes for Sale in Wailea, HI

Map of Wailea Luxury Homes for Sale

For Sale


8,942 people live in Wailea, where the median age is 55.5 and the average individual income is $66,640.08. Data provided by the U.S. Census Bureau.



55.5 years

Median Age


Population Density


Average Individual Income

Luxury Living in Wailea

Your Guide To

Luxury Living in Wailea

Wailea, HI, situated on the sun-kissed southwestern shores of Maui, epitomizes luxury living with its opulent homes, meticulously landscaped avenues, and breathtaking oceanfront vistas. This prestigious community is celebrated for its world-class resorts, championship golf courses, and exclusive residential offerings that cater to an affluent lifestyle. Wailea's luxury homes are architecturally stunning, ranging from modern villas with expansive ocean views to secluded estates surrounded by tropical gardens. These properties provide an unmatched level of privacy and exclusivity, often featuring custom designs that seamlessly integrate indoor and outdoor living to make the most of the island's idyllic climate.

The allure of Wailea's luxury real estate is complemented by its vibrant local culture and array of high-end amenities, creating a living experience that is both indulgent and culturally enriching. Residents enjoy access to private beach clubs, spa services, gourmet dining, and designer shopping within the community, reinforcing Wailea's reputation as a top-tier destination for discerning homeowners. The combination of natural beauty, sophisticated architecture, and a laid-back yet luxurious lifestyle makes Wailea an exceptional choice for those seeking the pinnacle of tropical luxury.

Wailea Real Estate Guides & Updates

Chelsea Dimin

Chelsea Dimin

Realtor® Broker

Real Estate Agent & Realtor Serving Wailea

Chelsea Dimin stands at the pinnacle of Maui's luxury real estate, consistently ranking among the top 1% of agents in sales volume. Chelsea specializes in oceanfront property and vacation homes and has over 17 years of expertise in real estate, business development, and advertising sales.

Originally from Milwaukee, Wisconsin, Chelsea holds degrees in Journalism and Spanish from the University of Wisconsin Madison. Her career journey led her to Los Angeles in 2006, honing negotiation skills representing top brands in digital media and advertising sales. In 2010, she joined New York Magazine's digital publication, NYmag.com, as the West Coast Advertising Sales Account Executive. In 2014, Chelsea embraced Maui's allure, obtaining her real estate license and collaborating with a local developer. As a Realtor Salesperson, she played a key role in transforming vacation rental estates into profitable ventures, attracting a global clientele.

Acquiring her Broker license in 2017, Chelsea made history in January 2023, becoming the first female Realtor to list and sell a $32 million dollar home in Makena, as reported by the Wall Street Journal. Today, Chelsea guides buyers in realizing their Maui dream homes. Known for tenacity and creativity, she forges connections, assesses needs, and delivers strategic results. Chelsea's signature is creating opportunities, leveraging a global network for off-market deals and win-win negotiations.

Clients appreciate Chelsea's commitment to staying informed, providing updates on values, market trends, and recommendations. Beyond real estate, Chelsea enjoys an active lifestyle, engaging in surfing, yoga, barre classes, mountain biking, beach runs, jungle hikes, and waterfall adventures with her husband Tim and beloved pitbull, Lulu.

“My mission is to exceed your expectations so that you never hesitate to refer your friends, family or coworkers to me in the future.”

Work With Chelsea

Are you interested in buying or selling a home on Maui? Contact me to tap into my local knowledge and global connections. My mission is to exceed your expectations so that you never hesitate to refer your friends, family or coworkers to me in the future.