Pineapple Hill Real Estate

Welcome to Pineapple Hill, a hidden gem nestled in the heart of Lahaina, Maui. This enchanting neighborhood is a true paradise for those seeking a blend of tranquility and vibrant island life. With its lush landscapes and stunning ocean views, Pineapple Hill offers a serene escape while being just minutes away from the bustling town of Lahaina.

Pineapple Hill is renowned for its luxurious properties, featuring spacious homes that boast contemporary designs infused with traditional Hawaiian elements. Many residences come equipped with private pools and expansive outdoor living spaces, perfect for entertaining or simply soaking in the breathtaking sunsets. The community is characterized by its well-manicured lawns and friendly neighbors, creating a warm and inviting atmosphere.

Nature enthusiasts will appreciate the nearby hiking trails and pristine beaches that showcase Maui's natural beauty. Whether it’s a morning stroll along the shoreline or an adventurous hike through lush greenery, Pineapple Hill provides ample opportunities to enjoy the great outdoors. Additionally, the neighborhood is conveniently located near renowned golf courses, making it a golfer's paradise.

The vibrant town of Lahaina is just a stone's throw away, offering a rich tapestry of cultural experiences, dining, and shopping. From fresh seafood restaurants to unique boutiques, there’s something for everyone.

In Pineapple Hill, you're not just buying a home; you're investing in a lifestyle filled with adventure, relaxation, and community spirit. Come discover the magic of this extraordinary neighborhood and experience the charm of island living at its finest!

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.