Kaanapali Hillside Homes with Fee Simple Land tenure

Welcome to Kaanapali Hillside, a stunning enclave nestled in the heart of Lahaina, Maui. This picturesque neighborhood offers a perfect blend of tropical beauty and luxurious living, making it an ideal destination for those seeking a slice of paradise.

Kaanapali Hillside is renowned for its breathtaking views of the Pacific Ocean and the majestic West Maui Mountains. As you meander through this charming community, you'll find beautifully designed homes that reflect the spirit of island living. Each residence boasts fee simple land tenure, granting homeowners full ownership of their property, which is a significant advantage in the real estate market.

The neighborhood is conveniently located near the world-famous Kaanapali Beach, where golden sands and crystal-clear waters invite you to soak up the sun and enjoy various water activities. For golf enthusiasts, the Kaanapali Golf Courses offer an exceptional golfing experience amidst stunning landscapes.

Kaanapali Hillside is not just about natural beauty; it also fosters a strong sense of community. Residents enjoy access to nearby shopping, dining, and entertainment options, ensuring that everything you need is just a short drive away. The vibrant town of Lahaina, rich in history and culture, is also just a stone's throw away, offering art galleries, local markets, and delightful restaurants.

In Kaanapali Hillside, every day feels like a vacation. Whether you’re looking for a permanent residence or a vacation home, this neighborhood promises a lifestyle filled with warmth, beauty, and endless opportunities for adventure. Embrace the Hawaiian dream and make Kaanapali Hillside your home today!

Newest Kaanapali Hillside Homes with Fee Simple Land tenure

$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.

$998,888

2 Beds ⋅ 2 Baths ⋅ 407553 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Beautiful remodeled single level 2-bedroom 2-bath unit with no interior stairs. This unit is one of the rare locations requiring only a few steps down from the parking lot to the front door. Enjoy stylish indoor-outdoor living, enhanced with 3 split air conditioning units, remodeled bathrooms and a remodeled kitchen for entertaining with 2 ovens. Located in the highly sought-after, gated community of The Masters at Kaanapali, this spacious unit offers an open floor plan with excellent natural light and cooling trade winds. Resort living with tropical breezes, swimming pools, tennis courts, pickle ball courts and incredible sunset views, offering pet friendly policies, and the ability to BBQ on your lanai. Just minutes from Whalers Village, Airport & Ka'anapali Beach, and world-class golf, this is an exceptional opportunity to own a piece of paradise at one of West Maui's most sought-after communities

50 Puu Anoano St Unit 1803, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$1,175,000

2 Beds ⋅ 2 Baths ⋅ 407217 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Enjoy stunning ocean, island, and golf course views from this beautifully situated upstairs 2-bedroom, 2-bathroom unit overlooking the 9th signature hole and 10th fairway of the Royal Kaanapali Golf Course. Located in the highly sought-after, gated community of The Masters at Kaanapali, this spacious unit offers an open floor plan with excellent natural light and cooling trade winds. It is being offered furnished. The community amenities include two swimming pools, hot tubs, four tennis courts, and beautifully landscaped grounds. Experience peaceful, resort-style living just minutes from world-class beaches, dining, shopping, and golf.

50 Puu Anoano St Unit 1904, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$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.