Kapalua Luxury Living

Pineapple Hill

With exquisite views, elegantly constructed homes, and everything needed to experience heaven on earth, the coveted homes of Pineapple Hill Estates are now for sale on the market. Designed to amplify Maui’s natural beauty and to ensure graceful and easy living, the houses on Pineapple Hill are the second phase of a secure gated community established in 1989.


With a strong and steadily increasing market value, the best time to invest in paradise is right now. Situated on the slopes of the West Maui mountains, Pineapple Hill has access to the raw beauty of some of Hawaii’s best hiking trails. From the mountains to the coast, experiences of pristine natural scenery are readily available. Enjoy the white sand and world-class surfing of the tropical beaches or the breathtaking views from the mountains – truly what is for sale at Pineapple Hill is not just a home but heaven on earth.

Real Estate Statistics

Average Price $4.1M
Lowest Price $1.9M
Highest Price $5.7M
Total Listings 6
Avg. Days On Market 187
Avg. Price/SQFT $1.3K

Property Types (active listings)

Pineapple Hill Homes For Sale

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$5,700,000

Pineapple Hill

104 Woodrose Pl, Kapalua

4 Beds 3.5 Baths 3,315 SqFt Residential MLS® # 403822

Days on Market: 252

New

$5,395,000

Pineapple Hill Estates

116 Pulelehua St 1, Kapalua

4 Beds 4.5 Baths 4,081 SqFt Residential MLS® # 406659

Days on Market: 7

$3,995,000

Pineapple Hill

406 Monarch Pl, Kapalua

3 Beds 3 Baths 2,794 SqFt Residential MLS® # 406739

Days on Market: 12

$3,900,000

Pineapple Hill

212 Crestview Rd, Kapalua

3 Beds 3.5 Baths 3,674 SqFt Residential MLS® # 406358

Days on Market: 106

Buying Real Estate on Maui

Buying Real Estate on Maui

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$3,800,000

↓ $450,000

Pineapple Hill

324 Cook Pine Dr, Kapalua

3 Beds 3.5 Baths 3,670 SqFt Residential MLS® # 405060

Days on Market: 182

$1,895,000

Kapalua

230 Crestview Rd 15, Kapalua

0 Beds 0 Baths 0 SqFt Land MLS® # 401010

Days on Market: 564

Recent Sales in Pineapple Hill

Sold
Closed: 07/31/2024

$6,875,000

Pineapple Hill Estates

229 Crestview Rd, Kapalua

4 Beds 4 Baths 4,598 SqFt Residential MLS® # 400764 Date Sold: July 31, 2024
Sold
Closed: 09/15/2023

$6,450,000

Pineapple Hill

330 Cook Pine Dr, Kapalua

4 Beds 4.5 Baths 4,723 SqFt Residential MLS® # 398466 Date Sold: September 15, 2023
Sold
Closed: 05/20/2025
222 Crestview Rd, Kapalua

$6,205,000

Pineapple Hill Estates

222 Crestview Rd, Kapalua

4 Beds 4.5 Baths 4,265 SqFt Residential MLS® # 405657 Date Sold: May 20, 2025
Sold
Closed: 07/28/2023

$6,150,000

Pineapple Hill

310 Cook Pine Dr, Kapalua

3 Beds 3.5 Baths 3,748 SqFt Residential MLS® # 398983 Date Sold: July 28, 2023
Buying Real Estate on Maui

Buying Real Estate on Maui

Read Evan's complete guide to buying a home or condo on Maui.

Read the Guide
Sold
Closed: 01/06/2023

$5,775,000

Pineapple Hill Estates

222 Crestview Rd, Kapalua

4 Beds 4.5 Baths 4,265 SqFt Residential MLS® # 396647 Date Sold: January 6, 2023
Sold
Closed: 03/07/2025

$5,750,000

Pineapple Hill at Kapalua

306 Cook Pine Dr 73, Kapalua

4 Beds 4.5 Baths 4,150 SqFt Residential MLS® # 401098 Date Sold: March 7, 2025
Sold
Closed: 06/10/2024

$5,513,000

Pineapple Hill

110 Woodrose Pl Lot 94, Kapalua

3 Beds 3.5 Baths 3,038 SqFt Residential MLS® # 401002 Date Sold: June 10, 2024
Sold
Closed: 06/14/2024

$4,750,000

Pineapple Hill

238 Crestview Rd, Kapalua

4 Beds 4.5 Baths 4,121 SqFt Residential MLS® # 400594 Date Sold: June 14, 2024
Sold
Closed: 06/27/2023

$4,400,000

Pineapple Hill

708 Fairway Dr, Kapalua

3 Beds 3.5 Baths 3,238 SqFt Residential MLS® # 398877 Date Sold: June 27, 2023
Sold
Closed: 05/12/2023

$4,300,000

Pineapple Hill Estates

116 Pulelehua St 1, Kapalua

4 Beds 4.5 Baths 4,081 SqFt Residential MLS® # 396881 Date Sold: May 12, 2023
Sold
Closed: 01/05/2023

$4,150,000

Pineapple Hill

708 Fairway Dr, Kapalua

3 Beds 3.5 Baths 3,400 SqFt Residential MLS® # 397252 Date Sold: January 5, 2023
Sold
Closed: 09/06/2023

$4,000,000

Pineapple Hill Phase II

105 Pulelehua St, Kapalua

3 Beds 3.5 Baths 3,851 SqFt Residential MLS® # 397856 Date Sold: September 6, 2023

Be Amazed By Kapalua and Pineapple Hill

No matter the time of day, the views afforded to Pineapple Hill Estates are absolutely dazzling. In the morning, you can bask in the glow of the sunrise while gazing out onto Lanai and Molokai. During the afternoon, you can enjoy the fact that Pineapple Hill is overlooking the world-famous Kapalua Bay Golf Course, one of the best golf courses on Maui, for expansive, unobstructed views. And, saving the best for last, the evening sky is lit up by gorgeous sunsets like fiery paintings each and every day. You will not be able to put a price tag on the fantastic vistas at Pineapple Hill.

As members of the Kapalua Resort, all homeowners are benefitted from the fantastic amenities provided. Perfect for leisure and exercise, the Olympic-sized swimming pool is available for use.

Residents are blessed with the privilege of discounted rates for the two renowned golf courses as well as the excellent tennis courts of which there are ten – both, of course, perfect for practicing your swing. Additionally, not only are you given access to the fabulous features of the pavilion and community, but you are also within walking distance of world-class dining and boutique shopping.

Pineapple Hill Neighborhood Map

Pinneapple Hill Kapalua Map

Construction and History of Pineapple Hill Estates

In the early 1990s, Pineapple Hill Kapalua was recognized as a tropical paradise characterized by raw beauty due to its elevated location. The development of luxury homes began, with an original plan of 99 exclusive homesites for residential use. As of 2001, the 31 residential homesites of Pineapple Hill Estates were annexed into Pineapple Hill in order to enhance the privileges of the community.

Initially, for the development, homesites were a quarter of an acre, with each homeowner given six modern and architecturally crafted floorplans to choose from. Subsequently, however, investors could customize their floorplan if two or more lots were purchased together.

Boasting plots of half an acre, plots at Pineapple Hill Estates grant the freedom to customize floorplans for new homes although only top rows of sites are permitted to have a second story. This has made Pineapple Hill Estates an even more attractive investment in an already striking location.

The Kapalua Real Estate Market | Reflecting Value Money Can't Buy

With its beaches, mountains, and the elegant lifestyle it offers, there is understandably strong value in the luxury neighborhoods of West Maui. While, understandably, recent world events have caused changing market trends. Considering the value retention of property on the land-scarce island of Maui, property in Kapalua has always been a good buy.

Kapalua, which is the greater area surrounding Pineapple Hill, is a wonderful part of the island of Maui with a median house price sitting slightly over $6 million, whereas Pineapple Hill Estates reflect the increased value its location offers at a median house price of $6 million.

Neighboring Napili has a lesser median of just over $1,800,000 but lacks the bountiful advantages Pineapple Hill offers. With its location, quality, and luxurious homes and views, properties for sale in Pineapple Hill boast priceless and as such are expected to maintain strong market value.

The Intersection of Heaven and Earth | Estates in Pineapple Hill

Undeniably, homes at Pineapple Hill and Pineapple Hill Estates are architecturally crafted to bring the absolute best of stylish living to homeowners. Since the location is heaven on earth, the homes bring that same philosophy in design. As mentioned above, homes built in Pineapple Hill Estates have exquisite features, and homes built on the top row often enjoy the privilege of a second story to truly capture the magnificent views.

Pineapple Hill is a residential area and as such the houses are generous and spacious. Most of the homes are held as a fee simple title and are ideal for purchase as a home away from home or for idealized Hawaii living. 

Pineapple Hill Homes for Sale | Beauty in Home and Nature 

West Maui gives its residents an idyllic lifestyle with its pure and unadulterated beaches with world-class surfing, gorgeous ocean vistas, and tropical natural settings but the homes in Pineapple Hill truly offer the best of the best.  Homes here are placed in a dreamlike location where you can experience boutique shopping and exquisite dining one day and then swim in clear blue waters followed by a round of golf at the Bay Course.

Imagine waking up by enjoying a leisurely swim in the resort’s remarkable pool and then being astounded by the natural beauty during a rigorous morning hike. Afterward, you can relax in the afternoon through some games of tennis, or, if you prefer, enjoy the golf courses. At the end of the day, the best of world cuisine is available to you as you bask in a glorious sunset.

Without a doubt, there is so much on offer to you in buying a home on Pineapple Hill you will not want to pass on any opportunity to invest here. For any inquiries please do not hesitate to contact Evan Harlow and view our fabulous properties in Pineapple Hill for sale for yourself.

Get In Touch With Evan!

Evan Harlow Maui

Evan Harlow ranks among the best real estate agents on Maui annually and is in the top 1% of Coldwell Banker agents worldwide in production. Evan has the expertise, experience, and work ethic to help you achieve your real estate buying and selling goals. We promise exceptional service and support from the beginning of the process through closing and beyond. See what Evan's clients are saying on Google.

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