Pineapple Hill

Comprised of approximately 97 single family detached homes and home sites, this is a private gated community with lot sizes of approximately one quarter acre. Views from above the Bay Golf Course and towards the neighboring islands of Molokai and Lanai enhance this prestigious location. Amenities include Manager's home, Clubhouse and pool, and two tennis courts.


Active Pineapple Hill Residential Listings

Photo of Listing #387278

314 Cook Pine Dr

$7,900,000
  • 5 Beds
  • 5.50 Baths
  • 7,229 SqFt
Magnificent 5 bedroom, 5 1/2 bath home with the finest craftsmanship and materials in this very distinctive home behind the gates at Pineapple Hill at Kapalua. Sprawled across 2 lots and meticulously maintained, the former home of one of music's all ...
Residential
Photo of Listing #389654

330 Cook Pine Dr 85/86

$5,995,000
  • 4 Beds
  • 4.50 Baths
  • 4,723 SqFt
A rare opportunity awaits with the offering of this elegant property- Within the Kapalua resort and the gated, prestigious neighborhood of Pineapple Hill you will find one of the finest properties situated on two contiguous lots of approximately one ...
Residential
Photo of Listing #387279

1212 Summer Rd

$5,900,000 In Escrow
  • 8 Beds
  • 8.50 Baths
  • 8,174 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 Kapal...
Residential
Photo of Listing #390126

1202 Summer Rd

$3,750,000 In Escrow
  • 3 Beds
  • 3.00 Baths
  • 3,586 SqFt
One of Pineapple Hill's best locations, this stunning home is situated overlooking the Kapalua Bay Course with sweeping views of the ocean and the island of Molokai. The main living area is on the ground floor, with three-bedroom suites, a den, din...
Residential
Photo of Listing #385476

112 Pulelehua St

$3,450,000
  • 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 inviti...
Residential
Photo of Listing #388871

508 Pacific Dr

$2,850,000 In Escrow
  • 4 Beds
  • 4.50 Baths
  • 4,105 SqFt
EXTRAORDINARY. MAUI. DEDICATED TO THE EXTRAORDINARY, THE EXCEPTIONAL, AND THE UNIQUE. This quality-built home exudes pride of ownership and attention to detail not seen in many homes. 508 Pacific boasts great views and is reminiscent of a formal lo...
Residential
    

Active Pineapple Hill Land Listings

Photo of Listing #388990

114 Pulelehua St

$1,180,000
  • Beds
  • Baths
  • 20,909 SqFt
Enjoy panoramic ocean and island views from this home site nestled along the Bay Course in the gated Pineapple Hill Estates neighborhood of Kapalua. As one of the last remaining vacant lots in Pineapple Hill and Pineapple Hill Estates, this is a spec...
Vacant Land
Photo of Listing #385002

308 Cook Pine Dr

$985,000
  • Beds
  • Baths
  • 10,019 SqFt
Enjoy sunset views, whales jumping during season and vistas of Molokai and Lanai. Pineapple Hill has a very nice recreation setup with 2 tennis courts and large swimming pool along with a pavilion for parties, weddings and receptions etc. This is on...
Vacant Land
Photo of Listing #380930

322 Cook Pine Dr 81

$899,000
  • Beds
  • Baths
  • 9,888 SqFt
Sale includes a set of "almost" complete home plans with an estimate to build of $1.9M from Crescent Home Builders. This is one of the last few remaining vacant Pineapple Hill Lots with the perfect orientation to enjoy the spectacular Kapalua ocean v...
Vacant Land
Photo of Listing #388568

1010 Sunset Pl

$879,000
  • Beds
  • Baths
  • 11,326 SqFt
Very 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 ...
Vacant Land
    

Listings provided courtesy of the REALTORS® Association of Maui.

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