Wailea, HI Real Estate & Homes for Sale

Looking for your dream home in Wailea, HI? Look no further than Chelsea Dimin, the area's top-rated real estate agent. With a deep understanding of the local market and a passion for helping her clients succeed, Chelsea is committed to helping you find your perfect home in this stunning Hawaiian town.

Homes for Sale in Wailea, HI

Map of Wailea 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

Wailea, Maui: The Ultimate Luxury Resort Community

Enjoy all the benefits of tropical paradise in Wailea, Maui—where dazzling beaches meet exquisite hospitality. Whether you're looking for an unforgettable getaway or a luxurious lifestyle destination, this exclusive resort community offers world-class golf courses and luxury hotels to suit every traveler's needs. Discover why so many people are drawn to its unparalleled beauty!


Location and Accessibility

Blessed with stunning weather and beautiful beaches, Wailea is situated on the sunny southern coast of Maui. An ideal destination for outdoor activities, it's only a few miles from Kihei town - close enough to explore attractions such as Haleakala National Park and the Road to Hana, yet far away enough for complete relaxation.

Outdoor Recreation

Wailea is an outdoor enthusiast's paradise. With its stunning beaches and world-class golf courses, this Hawaiian destination offers a range of possibilities for water sports lovers - from snorkeling to paddleboarding! For those seeking out breathtaking landscapes, the exquisite Wailea Beach Path provides access to some of Hawaii's most beautiful shorelines.


Dining and Shopping

Wailea is a haven for explorers seeking stylish shopping and refined cuisine. Foodies can savor the culinary delights of top-notch restaurants. At the same time, fashionistas delight in exclusive boutiques from renowned international designers at The Shops at Wailea, featuring artisan wares crafted by talented local artisans.

Community Events

Wailea has a strong sense of community, with several events that bring neighbors and visitors together throughout the year. The Wailea Film Festival is a beloved tradition, and the weekly Maui Farmers Market offers fresh produce and artisanal goods.


Wailea Luxury Real Estate

Wailea offers some of the most exclusive and upscale real estate in Hawaii, including luxurious condos, townhomes, and single-family homes. Some of the most notable properties in the area include:

  • Wailea Beach Villas: This oceanfront condo complex features luxurious 2-4 bedroom units, a private beach, and a fitness center.
  • Ho'olei at Grand Wailea: This gated community offers spacious 3-4 bedroom townhomes with private garages, high-end finishes, and a private beach club.
  • Wailea Golf Estates: This exclusive gated community features custom-built single-family homes, many with stunning ocean views and access to the Wailea Golf Club.

Located in Maui, Wailea is a prime destination for luxury seekers. Surrounded by world-renowned beaches and golf courses, this exclusive resort community provides an unbeatable combination of premier real estate options with a tight-knit sense of neighborhood spirit. With something to suit all lifestyles - from vacationers to full-time residents - Wailea has been hailed as the ultimate tropical paradise experience.

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.