Pineapple Hill

Nestled on the slopes of the West Maui mountains near Kapalua's famed Bay golf course, Pineapple Hill offers homeowners spacious lots with breathtaking ocean views. Located in a gated subdivision, homeowners have access to a pool, tennis courts and entertainment areas all while being in the midst of Hawaii's most sought-after resort community.
Fine dining, world-class golfing and some of the best Maui's most picture-perfect beaches are minutes away. Residents of the community have access to a plethora of luxury amenities at the Kapalua Resort, including spas at the Montage and Ritz, shopping at exclusive retailers, and a plethora of activities, to include hiking, snorkeling, golf, and much more.

Pineapple Hill Properties For Sale

New
Photo of Listing #399041

306 Cook Pine Dr 73

$6,150,000
  • 4 Beds
  • 4.50 Baths
  • 4,150 SqFt
This under-construction home will be the first brand-new home for sale in Pineapple Hill in over 12 years. This spacious, cutting-edge, 4-bedroom home with upstairs and downstairs primary bedrooms is located on one of the premier lots in Pineapple Hi...
Residential
Photo of Listing #398983

310 Cook Pine Dr

$6,250,000 In Escrow
  • 3 Beds
  • 3.50 Baths
  • 3,748 SqFt
This luxurious three bedroom home is located in one of Maui's most coveted destinations, Pineapple Hill, and boasts high-end finishes and exquisite upgrades throughout. As you step into this remarkable home, you'll be greeted by an open-concept layou...
Residential
Photo of Listing #398877

708 Fairway Dr

$4,500,000 In Escrow
  • 3 Beds
  • 3.50 Baths
  • 3,238 SqFt
Welcome to luxury living in Kapalua Maui's prestigious Pineapple Hill neighborhood. Located on the 5th fairway of the Kapalua Bay Course, this stunning 3 bedroom, 3.5 bathroom home boasts high ceilings, natural lighting, and breathtaking ocean views....
Residential
Photo of Listing #398665

518 Pacific Dr 60

$3,850,000
  • 4 Beds
  • 4.00 Baths
  • 3,357 SqFt
This is Pineapple Hill at its finest! This perfectly maintained 4-bedroom Pineapple Hill home is ideally located at the end of a cul-de-sac ensuring maximum privacy while enjoying magical ocean and sunset views. This fully-furnished, turn-key, two-st...
Residential
Photo of Listing #398491

238 Crestview Rd

$5,695,000
  • 4 Beds
  • 4.50 Baths
  • 4,121 SqFt
Stunning custom island home located in Kapalua's most coveted neighborhood, Pineapple Hill. This luxurious home is set up for indoor/outdoor island living with pocket sliders extending the spacious indoor living space flowing out to the expansive lan...
Residential
Photo of Listing #398466

330 Cook Pine Dr

$6,495,000
  • 4 Beds
  • 4.50 Baths
  • 4,723 SqFt
This private ocean view estate is situated on approximately a half-acre in one of Kapalua's most popular neighborhoods, Pineapple Hill. Remodeled in 2018 with a contemporary, elegant island inspired design, this home is one of the most secluded in t...
Residential
Photo of Listing #397856

105 Pulelehua St

$4,695,000
  • 3 Beds
  • 3.50 Baths
  • 3,851 SqFt
Fabulous custom Single level home in Pineapple Hill Phase II. Lots of off street parking and elegant porte cochere for your convenience. The views from the entry to the great room are magnificent. Molokai, Lanai, the Bay Course are captivating. The f...
Residential
Photo of Listing #397641

308 Cook Pine Dr

$1,800,000
  • Beds
  • Baths
  • 10,019 SqFt
One of the last remaining excellent building lots with a really great panoramic ocean view including Lana'i Island and Molokai Island. A new home with stunning, modern features has been designed by a well known local architect who can customize many...
Vacant Land
Photo of Listing #396915

234 Crestview Dr

$895,000
  • 4 Beds
  • 4.50 Baths
  • 4,012 SqFt
A 1/6 th fractional residence opportunity in beautiful Kapalua. This is a fabulous opportunity to own an exquisitely designed and furnished home within the gated community of Pineapple Hill Estates. This 4 bedroom, 4.5 bath Luxury home has over 4,000...
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Neighborhood Map

Map of Pineapple Hill Kapalua

Pineapple Hill Experts

Thinking of purchasing or selling a Pineapple Hills Home for sale? Contact us for a private consultation - our team encompasses some of the utmost experts in the Kapalua real estate market who would be happy to answer any questions.


West Maui Realtors
Island Sotheby's International Realty
Tel 808.665.1166
Fax 808.665.1155

West Maui Real Estate Leaders

Have Questions About the Real Estate Market in Kapalua, Kaanapali, Lahaina, and Napili area?

Our West Maui Real Estate experts have combined decades of experience in serving all facets of the immense West Maui real estate market and have expert-level local knowledge to best serve our clients. For a private consultation, stop by our conveniently located office at 5095 Napilihau Street, Ste 113A in the Napili Plaza, call us at 808-665-1166, or fill out the form below and one of our experts will be in touch.

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Listings provided courtesy of the REALTORS® Association of Maui.

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