Kaanapali Hillside Homes with Ocean View

Welcome to Kaanapali Hillside, a hidden gem nestled in the heart of Lahaina, Maui. This enchanting neighborhood is famed for its breathtaking ocean views, making it a coveted destination for those seeking both tranquility and the vibrant spirit of island life. Perched on a hillside, Kaanapali Hillside offers residents a unique vantage point to witness the mesmerizing sunsets over the Pacific Ocean, creating a picturesque backdrop for everyday living.

The homes in Kaanapali Hillside are designed to embrace the natural beauty of their surroundings, with many properties featuring expansive windows and spacious lanais that invite the stunning ocean vistas indoors. Imagine sipping your morning coffee while gazing out at the azure waters or hosting unforgettable gatherings as the sun dips below the horizon, painting the sky in hues of orange and pink.

This neighborhood is not just about the views; it’s also a community that thrives on connection. With easy access to the world-renowned Kaanapali Beach, residents can indulge in sun-soaked days of swimming, snorkeling, and sunbathing. The nearby Whalers Village offers a delightful array of shopping and dining options, ensuring that you have everything you need right at your fingertips.

Kaanapali Hillside is more than just a place to live; it’s a lifestyle. With its serene atmosphere, stunning ocean views, and proximity to the best that Maui has to offer, this neighborhood is perfect for those looking to embrace the essence of island living. Discover your dream home in Kaanapali Hillside, where every day feels like a vacation.

Newest Kaanapali Hillside Homes with Ocean View

$1,325,000

1 Beds ⋅ 2 Baths ⋅ 409869 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Rarely available custom residence at Masters at Kaanapali Hillside. Thoughtfully reimagined beyond a traditional renovation, this architecturally distinctive 1-bedroom, 2-bath home features ocean views, dramatic vaulted ceilings, and a one-of-a-kind custom floor plan that captures the essence of contemporary island living.The expansive chef's kitchen serves as the centerpiece of the home, showcasing quartz countertops, custom cabinetry, designer lighting, integrated appliances, and a large gathering island ideal for entertaining. Warm hardwood flooring, custom floating stairs, designer finishes, and renovated bathrooms enhance the home's sophisticated coastal aesthetic.The light-filled living area opens seamlessly to a generous covered lanai with ocean views and tropical surroundings, creating an effortless indoor-outdoor lifestyle. The spacious primary suite features vaulted ceilings, abundant natural light, and a custom wardrobe system. Located within the prestigious gated Masters at Kaanapali Hillside, residents enjoy beautifully maintained grounds, resort-style amenities, privacy, and convenient access to Kaanapali's world-renowned beaches, golf courses, dining, and shopping. A truly unique opportunity to own one of the most extensively customized and architecturally distinctive residences within Masters at Kaanapali Hillside.

50 Puu Anoano St Unit 1704, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$1,799,999

3 Beds ⋅ 2 Baths ⋅ 409756 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Condo 603 at The Masters Kaanapali Hillside is a rare and private 3-bedroom, 2-bath retreat offering sweeping ocean, golf course, and year-round sunset views from one of the community’s most coveted low-density buildings, which has only four residences total. Privately positioned at the lower end of the complex, this beautifully renovated turnkey home enjoys a cooler, more tranquil setting surrounded by lush tropical landscaping. Thoughtfully redesigned with high-end finishes throughout, the residence features premium flooring, granite countertops, GE appliances, spa-inspired Kohler shower systems, designer fixtures, abundant natural light, and seamless indoor-outdoor living enhanced by an automatic exterior shade. The expansive lanai flows onto a landscaped yard, creating the feel of a private single-family home and providing an exceptional space to relax, entertain, and take in the stunning Ka‘anapali views. Residents of this prestigious gated community enjoy pools, hot tubs, tennis courts, and convenient access to world-class beaches, championship golf, dining, and shopping just minutes away. Sold Fully Furnished.

50 Puu Anoano St Unit 603, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$1,444,000

2 Beds ⋅ 2 Baths ⋅ 407945 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Masters 903 isn’t just a ground floor jewel, it’s a front row legacy. From this premium, walk-right-out location, your lanai feels like the edge of the island, with mesmerizing Pacific Ocean and outer islands views filling the horizon. Step into a true “WOW” view, the moment you walk through the door. Maui’s legendary sunsets take center stage and the 13th Fairway of the Royal Ka’anapali Golf Course unfold below. Elegant Spanish porcelain tile runs throughout, giving the home a clean, modern, coastal feel that pairs perfectly with the relaxed island lifestyle. Offered fully furnished, with most artwork included, this residence is genuinely move-in ready, just bring your suitcase and start living. The coveted ground-floor setting means effortless living: no stairs, easy indoor-outdoor flow, and the rare combination of privacy, convenience, and a stellar view. The Masters at Ka’anapali Hillside is a low-density, gated community prized for its serenity and resort-caliber amenities, including 2 heated pools, 2 spas, 4 tennis courts, and lush, manicured grounds. Within minutes, you can be at world-famous Ka’anapali Beach and Whalers Village for white-sand shores, oceanfront dining, and boutique shopping. Home is where the heart is, let yours be in the heart of Ka'anapali!

50 Puu Anoano St Unit 903, Lahaina

Listing courtesy of Maui Luxury Real Estate LLC.

$1,395,000

2 Beds ⋅ 2 Baths ⋅ 406603 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

The Masters 1005 is a beautifully renovated ground floor corner unit located in the exclusive gated community of The Masters in Ka'anapali. This 2-bedroom, 2-bathroom condo offers sweeping panoramic ocean views of Lana’i and Moloka’i and overlooks the 13th fairway of the Royal Ka'anapali Golf Course, blending luxury living with the natural beauty of Maui. The interior has been thoughtfully updated and features a spacious master suite with a walk-in closet, a full laundry room, and window AC units for year-round comfort. This unit is ready to move in (select artwork and personal items excluded). The Masters community provides a resort lifestyle with two swimming pools, hot tubs, and tennis courts, all set within lush maintained grounds. This unit includes both an assigned carport and an open parking space. Privacy and tranquility define this prestigious enclave while still being just minutes away from the world-renowned Ka’anapali Beach, Whaler’s Village, and championship golf courses. Whether you’re seeking a full-time residence, a vacation home, or an investment property, this exceptional unit embodies the very best of island living.

50 Puu Anoano St Unit 1005, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

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Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.