Pineapple Hill Real Estate & Homes
Pineapple Hill Homes for Sale in Kapalua, Maui
Pineapple Hill is a residential neighborhood of custom homes on the hillside above Kapalua in West Maui, on streets such as Cook Pine Drive, Crestview Road and Pulelehua Street, with ocean and Molokai views. Homes were mostly built in the 1990s and early 2000s. Current Pineapple Hill listings appear below and update daily from the Maui MLS. Save a search to get new listings by email as soon as they come on the market.
Pineapple Hill at a Glance
| Location | Above Kapalua, West Maui (Lahaina mailing addresses) |
| Property types | Single-family homes and homesites |
| Typical homes | Two- to four-bedroom homes of about 2,300 to 4,500 square feet |
| Year built | About 1990 to 2002 |
| Recent sales | Home sales in recent years listed from about $3.6 million to $4.9 million |
| For sale now | About 5 homes, about $3.5 million to $5.2 million (October 2026) |
Buying in Pineapple Hill
Pineapple Hill offers single-family living near the Kapalua resort at a lower price than oceanfront Kapalua estates. Review the homeowners association rules, view corridors and any design review requirements, and check the age of roofs and systems on homes built in the 1990s.
More West Maui Resources
- Kapalua real estate
- Lahaina homes for sale
- West Maui neighborhoods
- Maui neighborhoods guide
- Free home valuation
Market figures are MLS list prices of sold and active listings as of October 2026 and change daily. Confirm details for any property with The Maui Property Team at (808) 217-8832.
View All Latest Pineapple Hill Homes for Sale
Positioned along the top row of Pineapple Hill in Kapalua, this furnished 3-bedroom, 3.5-bathroom residence offers expansive Pacific Ocean views and 3,674 square feet of ...
- 3 Beds
- 4 Baths
- 410414 MLS
- ACTIVE Status
- Fee Simple Tenure
Listing courtesy of Island Sotheby's International Realty(L).
Located within the prestigious gated enclave of Pineapple Hill in the world-renowned Kapalua resort, 620 Silversword Drive represents a rare offering in one of Maui’s mos...
- 4 Beds
- 5 Baths
- 409156 MLS
- ACTIVE Status
- Fee Simple Tenure
Listing courtesy of Keller Williams Realty Maui-L.
Breathtaking panoramic ocean views greet you the moment you step through the doors of 232 Crestview Road, located within the highly sought-after, gated community of Pinea...
- 3 Beds
- 3 Baths
- 408178 MLS
- ACTIVE Status
- Fee Simple Tenure
Listing courtesy of Coldwell Banker Island Prop-KP.
Welcome to 112 Pulelehua Street, an exceptional single-level residence in the gated Pineapple Hill II community of Kapalua Resort. Positioned on a half-acre on the Kapalu...
- 3 Beds
- 3 Baths
- 407964 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Coldwell Banker Island Prop-KP.
Upon entering this magnificent 3,315 sq. ft. home you will be mesmerized by its spectacular panoramic due west views of the Pacific Ocean between Lana'i and Moloka'i offe...
- 4 Beds
- 4 Baths
- 407481 MLS
- ACTIVE Status
- Fee Simple Tenure
Listing courtesy of Coldwell Banker Island Prop-KP.
Stunning ocean views! Gorgeous sunset views and neighbor Island views can be yours from this beautiful ocean view single-floor Pineapple Hill home. This home was remode...
- 3 Beds
- 3 Baths
- 406739 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Coldwell Banker Island Prop-KP.
Outstanding ocean, Lanai, Molokai, and sunsets from this single level residence at the top of Pineapple Hill at Kapalua, one of Maui's finest master planned communities. ...
- 2 Beds
- 4 Baths
- 406502 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Coldwell Banker Island Prop-KP.
This single-level, ocean view home in Pineapple Hill features an updated interior and swimming pool.
- 2 Beds
- 3 Baths
- 405656 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Island Sotheby's International Realty(L).
Welcome to Pineapple Hill, where elegance meets the effortless beauty of Maui’s world-renowned Kapalua Resort. Perched in one of Maui’s most sought-after communities, thi...
- 3 Beds
- 4 Baths
- 405060 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Island Sotheby's International Realty(L).
One of the last remaining building lots at the upscale Pineapple Hill subdivision with captivating ocean, sunsets, Lanai and Molokai views! A new home with stunning mode...
- 403360 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Coldwell Banker Island Prop-KP.
Very unique "L" shaped lot with lots of privacy from the street. Beautiful ocean, sunset, Lanai, and Molokai views. Located within the gates of Pineapple Hill at Kapalu...
- 401954 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Coldwell Banker Island Prop-KP.
Nestled in the prestigious enclave of Pineapple Hill overlooking the 5th fairway of the Kapalua Bay Golf Course, 712 Fairway Drive offers a luxurious retreat amidst Maui'...
- 3 Beds
- 3 Baths
- 401129 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Island Sotheby's International Realty(L).
This home is a completely reconstructed residence offering panoramic ocean, island, and sunset views. Impeccable quality craftsmanship throughout. The home was redesign...
- 3 Beds
- 4 Baths
- 401002 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Island Sotheby's International Realty(L).
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 sli...
- 4 Beds
- 5 Baths
- 400594 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Compass.
Built on a secluded double lot at the end of a private cul-de-sac in Kapalua Resort's Pineapple Hill gated community, is the prestigious residence known as Emerald Point....
- 6 Beds
- 7 Baths
- 400328 MLS
- CLOSED Status
- Fee Simple Tenure
Listing courtesy of Coldwell Banker Island Prop-KP.