Introducing 222 Crestview Road, Pineapple Hill Estates, Kapalua

Introducing 222 Crestview, in Kapalua's Pineapple Hill Estates

Dramatic sunsets are a nightly occurrence--the view from 222 Crestview

222 Crestview Road is a rare offering of a home situated at the Pinnacle of Pineapple Hill Estates, the newest residential community in Pineapple Hill. 

This second phase of the development was annexed into the community in 2001, and the homesites are significantly larger at approximately a half acre.  Architectural restrictions limit the roof heights of the lots below to 25 feet, but allowed homes along the top row to be two stories, maximizing the size and the views from this location.

This beautifully designed home is centered around a sculpture garden behind a gated private entry. Thoughtful design provides privacy for each of the four-bedroom suites:  there is a ground floor primary bedroom suite complete with ocean view lanai sitting area and landscaped shower garden, as well as an upstairs primary bedroom suite with a private lanai, separate laundry, and a flex space that can be used as an office, gym or sitting room.  There are two additional bedroom suites that focus out toward the beautifully landscaped gardens.

From the moment you enter this home, across a bridge through a tropically landscaped courtyard, the views of the Pacific Ocean and the outer island of Molokai begin to unfold.  The soaring ceilings of the great room are a dramatic backdrop for a custom sculpture by Australian artist, Robert Hague, which is included with the sale.

Take a Virtual Walkthrough

The great room has a seamless indoor/outdoor flow with pocketing doors that open to the expansive lanai and infinity edge pool with a beach shelf and spa. 

The inner courtyard provides a serene setting, with floor-to-ceiling windows that will illuminate your art collection and showcases the gardens from the guest bedroom suites and the living room and filling the home with natural light. 

The kitchen is a chef’s dream, featuring appliances by Sub Zero, Bosch, and Wolf, including a Sub Zero wine storage cabinet and refrigerator drawers, as well as a proofing drawer for baking.  The kitchen opens to outdoor dining with a built-in bar. 

The gracious Primary Bedroom Suite is on the ground floor, with a sitting area and fireplace.  The en suite features a jacuzzi tub, walk-in shower, and beautifully landscaped outdoor shower garden. 

Upstairs is a second Primary Bedroom suite complete with its own laundry and a private lanai with panoramic ocean and outer island views.  

Off the second floor primary suite is a large flex space that can be used for a gym, office, or sitting room.

The South Guest Bedroom Suite is currently used as an office, though it also is equipped with a projector and screen, along with blackout shades, should you want to use it as a media room.

 The North Guest Bedroom Suite features a private outdoor shower garden.

222 Crestview features a Porte-Cochere with circular drive, as well as an attached two car garage with a separate bay for a golf cart.  There is ample storage in the garage for surfboards, bikes and tools.

Floor Plan

The Floor Plan for 222 Crestview--this is a rendering from Matterport and an illustration of the floor plan.  Interested parties should do their own due diligence.

About Pineapple Hill

Pineapple Hill is one of Kapalua's most popular residential communities.  A gated enclave developed in two sections, Pineapple Hill, and later in 2001, Pineapple Hill Estates.  The first phase of Pineapple Hill are smaller homesites (typically around a quarter of an acre), whereas the homes in Pineapple HIll Estates are on larger lots (approximately a half acre). 

Combined, there are 130 homesites, however, several owners in the first phase of Pineapple Hill built homes on double lots, and one, which sold in 2021, was built on three lots.

The Market at Pineapple Hill

At the time of this post, there are just three homes listed for sale in Pineapple Hill and Pineapple Hill Estates, with asking prices ranging from $5,295,000 to $7,900,000.  There is one pending sale at $8,450,000. 

In vacant land, there are two lots listed for sale, one in phase I at $1,100,000 for a quarter acre, and another in Pineapple Hill Estates listed at $1,895,000 for just under a half acre. 

Current Home and Land Listings

Pineapple Hill Home Sales: A 5 year historical perspective

Pineapple Hill Land Sales: A 5 year historical perspective

For more information on Pineapple Hill and other residential offerings in the Kapalua Resort, please contact Courtney M. Brown, R(S)

Pineapple Hill & Pineapple Hill Estates Homes for Sale

Nestled In The Prestigious Enclave Of Pineapple...

$3,300,000 Pending Fee Simple

• 3 Beds
• 3 Baths
• 0.2 Acres
• 2,361 ft²

Residential

712 Fairway Dr, Unit Lot 58, Kapalua, HI

MLS® #401129

Listed By: Island Sotheby's Int'l Rlty(L)
Office Contact: Cell: 808-205-5201

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's Breathtaking Natural Beauty. This Spacious Single-level Three-bedroom, Two-bath Plus ...

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This Under-construction Home Will Be The First ...

$5,995,000 Active Fee Simple

• 4 Beds
• 4½ Baths
• 0.25 Acres
• 4,150 ft²

Residential

306 Cook Pine Dr, Unit 73, Kapalua, HI

MLS® #401098

Listed By: Keller Williams Realty Maui-L
Office Contact: Cell: 808-870-7736

This Under-construction Home Will Be The First Brand-new Home For Sale In Pineapple Hill In Over 12 Years. This Spacious, 4,150sf Cutting-edge, 4-bedroom Home With Upstairs And Downstairs Primary Bedrooms Is Located On One Of The Premier Lots In Pineapple H...

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Set Within The Gated Pineapple Hill Subdivision...

$5,900,000 Active Fee Simple

• 3 Beds
• 3½ Baths
• 0.23 Acres
• 3,038 ft²

Residential

110 Woodrose Pl, Unit Lot 94, Kapalua, HI

MLS® #401002

Listed By: Island Sotheby's Int'l Rlty(L)
Office Contact: Cell: 808-298-3498

Set Within The Gated Pineapple Hill Subdivision In The Kapalua Resort, 110 Woodrose Place Features A 3,038 Square Foot 3 Bedroom, 3 And A Half Bath Home On A Lot Of 9,963 Square Feet. Attention To Detail And Quality Of Finishes Is Evident Throughout This F...

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Located At The End Of A Cul De Sac In Kapalua R...

$5,995,000 Active Fee Simple

• 3 Beds
• 3½ Baths
• 0.23 Acres
• 4,574 ft²

Residential

1008 Sunset Pl, Kapalua, HI

MLS® #400951

Listed By: Coldwell Banker Island Prop-KP
Office Contact: Cell: 808-250-1583

Located At The End Of A Cul De Sac In Kapalua Resort’s Prestigious Gated Community, Pineapple Hill, Is A Beautiful, Two-level Residence With Fabulous Ocean, Sunset And Neighboring Island Views. The Ground Level Features The Great Room, Formal Dining Area, K...

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Located In Pineapple Hill Estates, Phase Ii, Ka...

REDUCED 4%

$7,495,000 Active Fee Simple

• 4 Beds
• 4 Baths
• 0.48 Acres
• 4,598 ft²

Residential

229 Crestview Rd, Kapalua, HI

MLS® #400764

Listed By: Coldwell Banker Island Prop-KP
Office Contact: Cell: 808-250-1583

Located In Pineapple Hill Estates, Phase Ii, Kapalua Resort’s Prestigious Gated Community, This Custom-built, Single-level Residence Boasts Panoramic Ocean, Sunset, And Neighboring Island Views. With Just Under 5,000 Square Feet Of Living Space On Approxima...

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Stunning Custom Island Home Located In Kapalua'...

REDUCED 12%

$4,900,000 Active Fee Simple

• 4 Beds
• 4½ Baths
• 0.47 Acres
• 4,121 ft²

Residential

238 Crestview Rd, Kapalua, HI

MLS® #400594

Listed By: Compass
Office Contact: Cell: 808-283-3436

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 Lanai, Poo...

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