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.

The community is minutes from the Kapalua clubhouse, with resorts, white-sand beaches and shopping nearby. Popular restaurants such as Sansei, Pineapple Grill and Cane & Canoe are a short drive from the community, which offers its residents the utmost luxury in a premiere destination resort.

Pineapple Hill Properties For Sale

Photo of Listing #379951

1212 Summer Rd

$6,300,000
  • 8 Beds
  • 8.50 Baths
  • 8,172 SqFt
Over 3/4 of an acre with this prestigious one of a kind 8,178 square foot home with 8 bedrooms, 8 1/2 baths, designed by Master Architect Rick Ryniak and built by Gary Dixon Construction, one of Maui's finest custom home builders. Located on the Kap...
Residential
Photo of Listing #380719

210 Crestview Rd 6

$3,750,000
  • 3 Beds
  • 4.50 Baths
  • 3,760 SqFt
Perched at the Summit of Pineapple Hill with glorious, unobstructed and private ocean view spanning the Island of Lanai, across The Molokai Channel and North to The Island of Molokai. Completed 2010! Renovated 2014-15! A contemporary oasis offering ...
Residential
Photo of Listing #381095

112 Pulelehua St

$3,495,000
  • 3 Beds
  • 2.50 Baths
  • 4,504 SqFt
Verde Pacifica graces the only golf course front lot in Pineapple Hill Estates that enjoys ocean views, views of Lanai and Molokai, sunset channel views, and Kapalua’s Cook Pine Ridge. This majestic estate offers just over 6,000 square feet of invi...
Residential
Photo of Listing #380406

506 Pacific Drive

$3,495,000
  • 5 Beds
  • 4.50 Baths
  • 4,151 SqFt
This casually elegant residence was completely remodeled in 2015 by one of Maui’s best luxury builders and architects, giving it a like new feel. It offers an inviting and warm ambience with striking ocean, neighbor island and sunset views. Elec...
Residential
Photo of Listing #380926

218 Crestview Rd 10

$3,400,000
  • 4 Beds
  • 3.00 Baths
  • 4,050 SqFt
Pineapple Hill at The Kapalua Resort. Large Corner lot with Fabulous Views. Watch the glorious sunsets over the Outer Islands of Lanai and Molokai. Enjoy a lifestyle of casual elegance at this prestigious home which was completed in 2002. Kapalua...
Residential
Photo of Listing #377885

328 Cook Pine Dr

$3,395,000
  • 4 Beds
  • 4.50 Baths
  • 3,750 SqFt
Premier residence designed by Jeffrey Long of Oahu and constructed by luxury builder, Web Development, located in Pineapple Hill Phase I. It offers phenomenal ocean, sunset and neighbor island views. Built with the highest quality materials this op...
Residential
Photo of Listing #380844

1214 Summer Rd 44

$2,950,000
  • 3 Beds
  • 3.50 Baths
  • 3,598 SqFt
Very private 3 bedroom, 3 1/2 bath home in a tropical setting behind the gates at Pineapple Hill, the Kapalua Resort's premier single family home development. A lifestyle of casual elegance awaits the fortunate buyer. Home is in immaculate conditio...
Residential
Photo of Listing #380877

614 Silversword Dr

$2,850,000
  • 4 Beds
  • 4.50 Baths
  • 3,298 SqFt
This stunning home is situated on one of Pineapple Hill's most desirable streets, Silversword Drive, which is known for its dramatic ocean views. Upon entering the home, your eye is immediately drawn to the views of the Pacific Ocean framed by the o...
Residential
Photo of Listing #381654

706 Fairway Dr

$2,820,000
  • 4 Beds
  • 4.50 Baths
  • 3,444 SqFt
Golf course fronting residence in excellent condition with 4 bedrooms and 4.5 bathrooms located along Kapalua’s Bay Course with beautiful views onto the course as well as of the ocean. Master bedroom suite and two guest suites are located on the lo...
Residential
Photo of Listing #380823

302 Cook Pine Dr 71

$2,750,000
  • 4 Beds
  • 4.50 Baths
  • 4,113 SqFt
Absolutely stunning contemporary-style estate with 4,113 square feet, 4 bedrooms, and 4 ½ baths. Well-designed open floor plan with exceptional craftsmanship and high-end amenities. This beautiful home offers a media room, office, koi pond and pho...
Residential
Photo of Listing #378478

200 Crestview Rd

$2,680,000
  • 3 Beds
  • 4.00 Baths
  • 4,118 SqFt
A meticulously built & cared for Gem of a Property that boasts vast, panoramic ocean & island views. Perched above the West Maui coastline at the highest viewpoint of Kapalua’s Pineapple Hill, this 4,100 sq ft home features impressive interior desi...
Residential
Photo of Listing #378838

708 Fairway Dr

$2,675,000
  • 3 Beds
  • 3.50 Baths
  • 3,400 SqFt
Golf course fronting residence with 3 bedrooms and 3.5 bathrooms located directly on the eleventh fairway of Kapalua’s Bay Course with beautiful views onto the course as well as of the ocean. This spacious residence is centrally air conditioned wit...
Residential
Photo of Listing #376869

114 Woodrose Pl

$2,499,000
  • 3 Beds
  • 4.00 Baths
  • 3,312 SqFt
Offered Turnkey, 114 Woodrose Place is located at the very end of a cul de sac with its own gate offering the ultimate in privacy in Kapalua’s Pineapple Hill. This 3 Bedrooms, 3-Full Baths and 2-Half Baths custom designed residence is situated on o...
Residential
Photo of Listing #378382

408 Monarch Pl

$2,298,800
  • 3 Beds
  • 3.50 Baths
  • 3,786 SqFt
Enjoy the light and airy feeling of this spacious 3 bedroom, 3 1/2 bath home within the prestigious gated community of Pineapple Hill in Kapalua. This lovely home is located at end of a cul de sac with ocean, outer Island and mountain views. A gener...
Residential
Photo of Listing #380647

516 Pacific Dr

$2,298,000
  • 3 Beds
  • 3.50 Baths
  • 3,666 SqFt
Stunning beauty of a home! Sparkling ocean views! Completely remodeled and exquisitely redone with the utmost of tropical ambiance and class. Private gate guarded community, walk to everything! Enjoy brilliant multi-hued Sunsets and intriguing islan...
Residential
Photo of Listing #382525

1200 Summer Rd

$2,100,000
  • 3 Beds
  • 3.50 Baths
  • 3,321 SqFt
Fantastic Bay Golf Course frontage location with expansive ocean, Lanai, and Molokai views! Watch the sunsets all year round! One of the largest lots in Phase 1 of Pineapple Hill with over 16,000 square feet of land! Come enjoy the casually elegan...
Residential
Photo of Listing #381081

1204 Summer Rd Pineapple Hill

$1,998,000
  • 4 Beds
  • 4.50 Baths
  • 3,704 SqFt
Front Row Pineapple Hill year round sunsets. Amazing island and sunset views overlooking beautiful Kapalua Bay Course. No rooftops from this special, private location. Gated community with resident manager. This quality built home is beautifully ...
Residential
Photo of Listing #380152

406 Monarch Pl

$1,998,000
  • 3 Beds
  • 3.00 Baths
  • 2,794 SqFt
If YOU have been craving your intimate and peaceful slice of Paradise, YOUR Time Is Now! Nestled on a cul de sac of a quiet and exclusive neighborhood within the gated community known as Pineapple Hill exists YOUR home at 406 Monarch Place. Offerin...
Residential
Photo of Listing #376347

306 Cook Pine Dr

$1,275,000
  • Beds
  • Baths
  • 10,890 SqFt
One of the few remaining lots available at Pineapple Hill Phase I . This estate site offers spectacular ocean views from a perfect elevation. It also features year round sunset views as well as views of the neighbor islands of Lanai & Molokai . Wheth...
Vacant Land
Photo of Listing #369310

1010 Sunset Pl

$1,275,000
  • Beds
  • Baths
  • 11,326 SqFt
Unique "L" shaped lot affording privacy from the street with beautiful views of the ocean, Molokai, and Lanai. Located within the privacy gates of Pineapple Hill at Kapalua, Maui's premier resort with its 2 championship golf courses, the 5 star Ritz...
Vacant Land
Photo of Listing #381724

624 Silversword Dr Lot 28

$1,250,000
  • Beds
  • Baths
  • 9,881 SqFt
Spectacular views are yours from this beautiful, level lot overlooking the Kapalua Bay Golf Course. Additional photos will be available shortly! There are only a handful of remaining home sites not built, and this location is truly one of the best i...
Vacant Land
Photo of Listing #380819

1004 Sunset Pl

$1,195,000
  • Beds
  • Baths
  • 15,769 SqFt
Located in the gated community of Pineapple Hill at Kapalua, 1004 Sunset Place is one of a few remaining land parcels available to build. Pineapple Hill was strategically designed with the very best views in mind. All the homes are terraced and buil...
Vacant Land
Photo of Listing #380930

322 Cook Pine Dr 81

$1,185,000
  • Beds
  • Baths
  • 9,888 SqFt
This is one of the last few remaining vacant Pineapple Hill Lots with the perfect orientation to enjoy the spectacular Kapalua ocean views and gorgeous sunsets setting between the outer islands of Lanai and Molokai. This ideal location was selected ...
Vacant Land
Photo of Listing #379795

114 Pulelehua St

$1,180,000
  • Beds
  • Baths
  • 20,909 SqFt
This lot is exclusively located in Pineapple Hill Estates. Boasting over 21,000 sq ft of land, enjoy year round sunsets and outer island horizon views of both Lanai and Molokai. At the perfect elevation, this lot is waiting for a premier custom Maui...
Vacant Land
New
Photo of Listing #382582

216 Crestview Rd 9

$1,095,000
  • Beds
  • Baths
  • 12,200 SqFt
Live the Kapalua dream at the top of the Hill in Pineapple Hill Phase I with spectacular sunset views, whale watching and vistas of the outer islands of Lanai and Molokai in full view. This graded, level lot is easy to build on and could come with a...
Vacant Land
Photo of Listing #382281

234 Crestview Dr 234

$595,000
  • 4 Beds
  • 4.50 Baths
  • 4,012 SqFt
Sale represents a 1/6th interest in this Pineapple Hill Home. A lifestyle of casual elegance is yours is an amazing home with four bedrooms four and one half baths and over 4,000 sq.ft. of luxury living. A total of 19,989 sq.ft. of land enhanced by...
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