Pineapple Hill Real Estate

Welcome to Pineapple Hill, a hidden gem nestled in the heart of Lahaina, Maui. This enchanting neighborhood is a tropical paradise that beautifully blends the laid-back island lifestyle with modern amenities, making it an ideal place to call home.

Pineapple Hill is renowned for its stunning views of the Pacific Ocean and the majestic West Maui Mountains. The area is characterized by well-manicured landscapes, vibrant tropical flora, and an array of luxurious homes that reflect the essence of island living. Residents here enjoy a sense of community that is both welcoming and warm, with neighbors often gathering for sunset barbecues or leisurely strolls along the scenic paths.

One of the most charming aspects of Pineapple Hill is its proximity to Lahaina’s historic district. Just a short drive away, you can explore the rich cultural heritage of this former whaling town, filled with art galleries, boutique shops, and delightful dining options. Enjoy fresh seafood at local restaurants or immerse yourself in the vibrant nightlife that Lahaina has to offer.

For outdoor enthusiasts, Pineapple Hill is a gateway to some of Maui’s best recreational activities. From world-class surfing and snorkeling at nearby beaches to hiking the lush trails of the West Maui Mountains, adventure awaits at every turn.

Whether you’re looking for a permanent residence, a vacation home, or an investment opportunity, Pineapple Hill offers a unique lifestyle that captures the essence of Hawaiian living. Come experience the magic of this breathtaking neighborhood and discover why Pineapple Hill is the perfect place to create lasting memories.

Newest Listings in Pineapple Hill

$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.