Pineapple Hill: Seamless Estate Living within the Kapalua Resort

Situated on the hillside above the pristine fairways of the Kapalua Bay Golf Course, Pineapple Hill is a gated community within the Kapalua Resort that marries exclusivity, sweeping ocean and island views, and daily access to resort-level amenities. With just a handful of custom homesites and estates, the neighborhood offers an intriguing blend of privacy and proximity—ideal for those seeking a refined West Maui lifestyle.

 At a Glance: Pineapple Hill

• Location: Kapalua Resort, West Maui — elevated hillsides overlooking the Bay Course and toward Moloka‘i and Lāna‘i. 

• Community Size: Original phase ~99 lots (~¼-acre each) plus “Pineapple Hill Estates” phase ~31 homesites (~½-acre) for greater scale and views. 

• Lot Sizes: Parcels from roughly 10,000 sq ft up to ~20,000 + sq ft, many with sizeable yard/pool space and elevated orientation. 

• Typical Home Sizes / For Sale: Listings show homes of 2,700–4,000+ sq ft, 3–4 bedrooms, with recent asking prices from ~$3.9 M to ~$5.7 M and higher. 

• Setting: Perched above the resort, affords panoramic sunsets, outer-island views (Moloka‘i, Lāna‘i) and golf-course foreground. 

• Resort Proximity: Minutes to Kapalua’s championship golf courses (Bay & Plantation), Kapalua Beach, DT Fleming Beach, the Shops at Kapalua, Montage Kapalua Bay spa, and top dining options like Merriman’s Kapalua and Cane & Canoe.

 Elevated Homes, Exceptional Views

In Pineapple Hill, the homes are situated to take full advantage of their hillside terrain. Many residences feature open-air lanais, pool decks oriented toward vivid sunsets, and generous lot spacing to preserve privacy and view corridors. The proximity to the Bay Course fairways adds a green foreground without sacrificing the ocean vista beyond. The feeling here is both resort-adjacent and distinctly residential—quiet lanes, mature landscaping, premium finishes, and large-scale homes built for comfort, entertaining, and the long view. 

 Resort-Level Lifestyle at Your Doorstep

Living in Pineapple Hill means you wake up in one of West Maui’s most privileged residential settings and step into a resort playground within minutes. Tee off at Kapalua’s Bay or Plantation Courses, launch a snorkel at Kapalua Beach, walk the coastal trail to DT Fleming Beach, or dine at restaurants like Plantation House or Sansei Kapalua. The Shops at Kapalua offer boutique shopping, while the Spa Montage and Kapalua Tennis Garden provide wellness and recreation. Yet at day’s end you return to the calm of the gate, the elevated lot, and the view that is all your own.

What Owners Love About Pineapple Hill

• Premier View Corridors
  Homes are strategically oriented to capture sunsets, outer-island vistas, and golf-course foregrounds that enhance both daily living and long-term value. 

• Generous Lot Size & Privacy
  With larger parcels and gated access, Pineapple Hill offers estate-scale living with the feeling of a private community. 

• Resort Access, Residential Quiet
  Everything Kapalua offers is near—beaches, golf, spa, dining—yet the streets of Pineapple Hill remain calm, home-oriented, and low-density.

• Established Neighborhood with Quality Finish
  The homes here reflect custom architecture, premium materials, and thoughtful indoor-outdoor integration suited to Maui’s climate. 

 For Those Exploring Pineapple Hill

If you’re seeking a top-tier West Maui home where views, location, and exclusivity converge, Pineapple Hill stands out. I can help you review available listings (including often quiet off-market properties) and evaluate which attributes matter most—view orientation, pool placement, lot size, finish level—and align those with your timeline and lifestyle.

Representing Your Property with Precision

If you already own in Pineapple Hill and are considering a move, refinement, or outright sale, representation must match the caliber of the community. With Coldwell Banker Global Luxury backing, I deliver white-glove service: high-impact photography, cinematic video, curated property narratives, and global syndication. Every detail—planning, presentation, buyer targeting—is designed to serve homes of this pedigree.

Pineapple Hill: Where Kapalua Resort Living Meets Private Estate Privacy

In Pineapple Hill you gain a little of both worlds—resort amenities and personal sanctuary. With elevated terrain, premium lot size, and low turnover, it remains one of the most coveted residential addresses in Kapalua. Whether for second-home ownership, lifelong residence, or investment, Pineapple Hill offers lifestyle, prestige, and enduring value.