Pineapple Hill Homes for Sale

Welcome to Pineapple Hill, a hidden gem nestled in the heart of Lahaina, Maui. This enchanting neighborhood offers a unique blend of tropical charm and modern luxury, making it an ideal location for those seeking a serene island lifestyle. Pineapple Hill is renowned for its stunning ocean views, lush landscapes, and a welcoming community atmosphere that invites you to unwind and embrace the beauty of Hawaiian living.

As you stroll through the winding streets of Pineapple Hill, you'll be captivated by the meticulously designed homes that reflect the island's natural beauty. These properties often feature spacious layouts, exquisite finishes, and private outdoor spaces perfect for soaking in the sun or hosting gatherings with family and friends. Many homes boast panoramic views of the Pacific Ocean, providing a breathtaking backdrop that changes with the setting sun.

In addition to its picturesque scenery, Pineapple Hill is conveniently located near some of Maui’s best attractions. Enjoy easy access to pristine beaches, world-class dining, and vibrant shopping options in nearby Lahaina. The area also offers a range of outdoor activities, from hiking scenic trails to snorkeling in crystal-clear waters, ensuring that adventure is never far away.

For those interested in making Pineapple Hill their home, there are a variety of homes for sale that cater to diverse tastes and budgets. Whether you’re searching for a cozy retreat or a luxurious estate, Pineapple Hill promises a lifestyle filled with beauty, tranquility, and the warmth of island living. Discover your slice of paradise today!

Newest Pineapple Hill Homes for Sale

$5,195,000

3 Beds ⋅ 4 Baths ⋅ 408268 MLS ⋅ Fee Simple Tenure

Set against the dramatic backdrop of the Pacific, 1008 Sunset Place offers a rare opportunity to own a refined island residence in the heart of Kapalua. Perfectly positioned to capture glowing sunsets, gentle trade winds, and sweeping ocean views, this Kapalua home is thoughtfully designed for seamless indoor–outdoor living. Open, light-filled interiors flow effortlessly to expansive lanais, creating ideal spaces for entertaining, dining al fresco, or simply unwinding while enjoying seasonal whale watching during the winter months. Thoughtful architectural lines, quality finishes, and casually elegant furnishings contribute to a timeless island aesthetic. The well-appointed kitchen features premium Sub-Zero and Dacor appliances, enhancing both form and function. Located within the gated community of Pineapple Hill, one of Kapalua Resort’s most sought-after residential enclaves, residents enjoy access to a community swimming pool, tennis and pickleball courts, and on-site resident management. Pineapple Hill offers close proximity to Kapalua’s world-class amenities, including championship golf courses, award-winning beaches, scenic coastal trails, tennis facilities, and fine dining—while maintaining a sense of privacy and tranquility. This is West Maui living at its finest, defined by ocean views, spectacular sunsets, and the enduring appeal of the Kapalua lifestyle.

1008 Sunset Pl, Lahaina

Listing courtesy of Island Sotheby's International Realty(L).

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.