Pineapple Hill Kapalua

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Set against the dramatic backdrop of the Pacific, 1008 Sunset Place offers a rare opportunity to own a refined island residence in the heart of Kapalua. Perfectly positioned to capture glowing sunsets, gentle trade winds, and sweeping ocean views, this Kapalua home is thoughtfully designed for seamless indoor–outdoor living. Open, light-filled interiors flow effortlessly to expansive lanais, creating ideal spaces for entertaining, dining al fresco, or simply unwinding while enjoying seasonal whale watching during the winter months. Thoughtful architectural lines, quality finishes, and casually elegant furnishings contribute to a timeless island aesthetic. The well-appointed kitchen features premium Sub-Zero and Dacor appliances, enhancing both form and function. Located within the gated community of Pineapple Hill, one of Kapalua Resort’s most sought-after residential enclaves, residents enjoy access to a community swimming pool, tennis and pickleball courts, and on-site resident management. Pineapple Hill offers close proximity to Kapalua’s world-class amenities, including championship golf courses, award-winning beaches, scenic coastal trails, tennis facilities, and fine dining—while maintaining a sense of privacy and tranquility. This is West Maui living at its finest, defined by ocean views, spectacular sunsets, and the enduring appeal of the Kapalua lifestyle.

Pineapple Hill 1008 Sunset Pl, Kapalua

$5,395,000 - 3 Beds, 3.50 Baths, 4,574 Sf

MLS® # 408268

Fee Simple
Island Sotheby's International Realty(L)

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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 offering colorful year-round sunsets. A remodeled masterpiece featuring vaulted cedar ceilings, Italian marble and eucalyptus wood floors, quartz countertops and sapele cabinets, just to name a few of the recent refinements of this tastefully furnished home. This most popular floorplan offers all 4 bedrooms, 3 1/2 bathrooms, living room, kitchen, outdoor living are and pool on the main level. The added bonus of an upstairs loft offers many use options, currently set up as an office/sitting area to enjoy the ocean views from the high dormer windows. A beautiful infinity edge pool with Baja steps and spa was just completed, with the entire house and pool equipment are supported by 52 solar panels and 2 Tesla batteries. This home is perched on a quiet cul-de-sac at the crest of Pineapple Hill, a highly desirable gated subdivision which offers residents a very large community/lap pool, tennis & pickleball courts, a pavilion / entertainment area, catering kitchen and barbecues. Pineapple Hill itself is located inside the 1,650-acre resort area of Kapalua's famed 23,000-acre plantation. Kapalua offers more than 100 miles of hiking trails, duck pond, bike trails, tennis center, two world famous golf courses, two five-star hotels plus five-star Montage Spa and numerous fine dining restaurants, all accessible via complimentary resort-wide shuttles. 104 Woodrose Place is a must-see home in impeccable condition, it looks and shows as if it were built yesterday.

Pineapple Hill 104 Woodrose Pl, Kapalua

$5,395,000 - 4 Beds, 3.50 Baths, 3,315 Sf

MLS® # 407481

Fee Simple
Coldwell Banker Island Prop-KP

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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 Kapalua Bay Course overlooking the Pacific Ocean, this redesigned 3-bedroom, 2.5-bathroom home offers more than 4,500 sq. ft. of interior living space and over 1,500 sq. ft. of lanais for seamless indoor–outdoor living. A grand set of double doors leads into an open-air atrium filled with tropical landscaping, an architectural centerpiece that brings natural light and Kapalua’s cooling breezes into the heart of the home. The great room follows, defined by soaring ceilings, ?Ohi?a details, and a 30-foot multi-panel sliding glass wall that pockets completely out of view. When opened, the interior blends effortlessly with the pool terrace, golf course frontage, and the ocean beyond, creating a true open-air living experience. The floor plan flows easily between the indoor and outdoor dining areas, a mirrored bar, entertainment space, and a chef’s kitchen. The kitchen has been fully renovated with custom open-louvered cabinetry, 3-inch Volcano granite, and a suite of premium appliances including SubZero refrigeration, a Wolf 48” dual-fuel range, Bosch double ovens, SubZero drawer systems, and a Dacor hood—ideal for cooking and entertaining. The primary suite is a private retreat with floor-to-ceiling sliders, a custom Kapalua stone fireplace, and a peaceful connection to the outdoors. Its spa-inspired bathroom features Volcano granite counters, a freestanding tub, black Kohler fixtures, Toto sinks, a heated towel bar, and new stone flooring. Both guest suites offer comfort and privacy with upgraded lighting, shutters, blinds, fans, and ensuite bathrooms with custom cabinetry, Volcano granite, and refined finishes. A temperature-controlled wine room sits just off the great room—perfectly positioned for entertaining. Outdoor living is at the core of this property. The heated freeform pool and spa sit along a gentle waterfall feature. Multiple lounging and dining areas capture sweeping views of the golf course, ocean, and sunsets over Moloka‘i. Tiki torches, refinished ?Ohi?a posts, new landscaping, and remote-controlled lanai screens enhance the resort-like setting. The home has been extensively improved with new LED lighting throughout, upgraded HVAC systems, a solar hot water system, new exterior paint, irrigation upgrades, new pool equipment, a refreshed driveway, and a new Raynor garage door with epoxy-coated flooring. Located within Kapalua Resort, owners enjoy access to world-class golf, beautiful beaches, coastal trails, dining, tennis, pickleball, and the resort shuttle. 112 Pulelehua Street offers an exceptional combination of design, comfort, and location in one of Maui’s most desirable communities.

Pineapple Hill 112 Pulelehua St, Kapalua

$5,300,000 - 3 Beds, 2.50 Baths, 4,504 Sf

MLS® # 407964

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Coldwell Banker Island Prop-KP

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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 Pineapple Hill Estates at Kapalua. This luxurious single-level residence spans 3,354 square feet of interior living space and is set on a large half acre lot. The property is ideally positioned at the end of a quiet cul-de-sac, nestled between two vacant lots offering exceptional privacy and the potential for further expansion. The home features three bedrooms and three bathrooms plus a bonus room adjacent to the 2 car garage, with thoughtfully designed living spaces that open seamlessly to spacious lanais. Highlights include a designer walk-in closet in the primary suite, a Jacuzzi soaking tub, state-of-the-art appliances, Ubatuba granite countertops, cherry wood cabinetry, a fireplace, ceramic Moro Italian wood like floor tiles and elegant finishes. Outdoor pleasures include a large lap pool and spa adorned with luxurious Monier tile imported from Switzerland, creating a true resort-style experience. Recent improvements include a upgraded AC and Lutron Smart home system installed in 2025. Ownership in Pineapple Hill Estates provides access to premier amenities including a private clubhouse, swimming pool, tennis courts, and pickleball courts. The surrounding Kapalua resort area is home to the world-famous Plantation golf course, scenic hiking trails, and renowned five-star resorts such as Montage Kapalua Bay and The Ritz-Carlton. A variety of acclaimed restaurants offer both local flavors and world-class dining experiences. Offered fully furnished, this exceptional home presents a rare opportunity to own a private piece of paradise—ready for your personal touch and perfectly suited for embracing the refined elegance of luxury island living.

Pineapple Hill 232 Crestview Rd, Kapalua

$5,200,000 - 3 Beds, 3.00 Baths, 3,354 Sf

MLS® # 408178

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Coldwell Banker Island Prop-KP

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Welcome to 116 Pulelehua Street in Pineapple Hill Estates, where elegance meets leisure! Nestled behind the scenic 7th tee box of the renowned Kapalua Bay Course, this stunning home is designed for both relaxation and enjoyment. With its inviting westerly views stretching down the iconic 7th fairway to Molokai, every evening is graced by breathtaking sunsets that will leave you in awe. This elegant single-story retreat features a thoughtfully designed dual-master suite floor plan that prioritizes comfort and luxury. Imagine waking up to the serene sight of expansive golf course and ocean vistas from the comfort of your own haven. This fully-furnished sanctuary boasts four ensuite bedrooms, accented by exquisite travertine floors and countertops, seamlessly blending style with functionality. As part of the community, indulge in a wealth of on-site amenities: take a refreshing dip in the large heated pool, challenge friends to a match on the tennis/pickleball courts, or simply unwind at the clubhouse. If that’s not enough, the surrounding resort amenities elevate your lifestyle even further. Imagine treating yourself to a day at the award-winning Montage spa, perfecting your swing on world-class golf courses like the Plantation Course and The Bay Course, or savoring delectable dishes at some of the island's finest restaurants—all just moments from your door. Experience the finest blend of luxury living and island lifestyle at 116 Pulelehua Street. Your paradise awaits.

Pineapple Hill Estates 116 Pulelehua St 1, Kapalua

$4,950,000 - 4 Beds, 4.50 Baths, 4,081 Sf

MLS® # 406659

Fee Simple
Keller Williams Realty Maui-L

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Pineapple Hill 212 Crestview Rd, Kapalua

$3,900,000 - 3 Beds, 3.50 Baths, 3,674 Sf

MLS® # 406358

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Island Sotheby's International Realty(L)

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230 Crestview Road is one of the few remaining undeveloped lots in Pineapple Hill Estates, Kapalua Resort's prestigious gated residential community. This estate site offers magnificent ocean and neighbor island views. Plans and approved building permits are to be included in the sale. This custom design features enclosed living space of 3,766 square feet, covered lanais of 1,145 square feet, a covered entry of 438 square feet, and garage and storage of 715 square feet, with total footprint of 6,064 square feet. Additional amenities in the Pineapple Hill development include a Resident Manager, a Pavilion with a fabulous pool, entertainment area, catering kitchen, barbecues, and tennis courts. Kapalua Resort amenities include fabulous beaches, two world class golf courses, The Bay Course and The Plantation Course, as well as tennis facilities, hiking trails, luxury hotels and spa, and fine dining.

Pineapple Hill Estates 230 Crestview Rd 15, Kapalua

$1,895,000

MLS® # 401010

Fee Simple
Coldwell Banker Island Prop-KP

Pineapple Hill is one of the most sought-after neighborhoods in Maui, with a convenient location in the heart of Kapalua near all the amenities that the resort has to offer. Parcels start at a quarter acre, ensuring privacy to all owners and their guests. Maintenance fees are $800 per month for residential properties and $50-120 for vacant parcels.

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Contact us for more information about Pineapple Hills. We are well versed in the luxury Kapalua real estate market and this subdivision's value within.

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Pineapple Hill Kapalua

Pineapple Hill Homes For Sale

Pineapple Hill 1008 Sunset Pl, Kapalua

Pineapple Hill 104 Woodrose Pl, Kapalua

Pineapple Hill 112 Pulelehua St, Kapalua

Pineapple Hill 232 Crestview Rd, Kapalua

Pineapple Hill Estates 116 Pulelehua St 1, Kapalua

Pineapple Hill 212 Crestview Rd, Kapalua

Pineapple Hill Estates 230 Crestview Rd 15, Kapalua

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Pineapple Hill Kapalua

Pineapple Hill Homes For Sale

Pineapple Hill 1008 Sunset Pl, Kapalua

Pineapple Hill 104 Woodrose Pl, Kapalua

Pineapple Hill 112 Pulelehua St, Kapalua

Pineapple Hill 232 Crestview Rd, Kapalua

Pineapple Hill Estates 116 Pulelehua St 1, Kapalua

Pineapple Hill 212 Crestview Rd, Kapalua

Pineapple Hill Estates 230 Crestview Rd 15, Kapalua

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