Pineapple Hill Homes with Pool

Welcome to Pineapple Hill, a hidden gem nestled in the heart of Lahaina, Maui. This picturesque neighborhood is renowned for its stunning vistas, lush landscapes, and a relaxed island lifestyle that beckons both residents and visitors alike. With its charming streets lined with swaying palm trees, Pineapple Hill offers a tranquil escape while being just minutes away from the vibrant culture and activities of Lahaina.

One of the standout features of homes in Pineapple Hill is the luxurious private pools that many properties boast. Imagine stepping out of your beautifully designed home to take a refreshing dip in your own pool, surrounded by tropical foliage and the soothing sounds of nature. These homes are perfect for entertaining friends and family or simply enjoying a peaceful afternoon in the sun.

The neighborhood is not just about stunning homes; it’s also about community. Residents here enjoy a close-knit atmosphere where neighbors become friends, and local events foster a sense of belonging. With easy access to pristine beaches, world-class dining, and a plethora of outdoor activities, Pineapple Hill offers the perfect balance of relaxation and adventure.

Whether you’re looking for a permanent residence or a vacation getaway, Pineapple Hill is an idyllic choice. Embrace the Hawaiian lifestyle in a home with a pool, where every day feels like a vacation, and the beauty of Maui is right at your doorstep. Come explore Pineapple Hill, where your dream home awaits!

Newest Pineapple Hill Homes with Pool

$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.