Maui Real Estate Search

Homes for Sale

$1,325,000
1 Beds ⋅ 2 Baths ⋅ 409869 MLS ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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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Kaanapali Hillside from Above

Kaanapali Hillside – Elevated Residential Living Above Kaanapali

Perched above the legendary Kaanapali Resort corridor and offering sweeping views of the Pacific Ocean, Maui’s neighboring islands, and seasonal whales breaching offshore, Kaanapali Hillside is one of West Maui’s most coveted residential communities. Quiet, established, and elevated, this neighborhood blends serene island living with convenient access to world-class beaches, golf, shopping, dining, and resort recreation below.

Unlike resort-zoned properties, Kaanapali Hillside is primarily a residential enclave composed of custom single-family homes, many designed to capture the incredible vistas afforded by its hillside elevation. With mature landscaping, varied architectural styles, and a quiet neighborhood feel, it appeals to full-time residents, second homeowners, and families seeking privacy without sacrificing access to everything West Maui has to offer.

This page breaks down what makes Kaanapali Hillside unique, from its characteristics and home features to lifestyle advantages and market considerations.

About the Neighborhood

  • Developed primarily in the 1980s and 1990s, with continuous renovation and modernization
  • Quiet, established residential community without a gated entry
  • Roads follow the hillside contours, offering many cul-de-sacs and quiet streets
  • Underground utilities contribute to unobstructed views and a tidy streetscape
  • Moderate homeowner association or community association structures in some sections (primarily for roadway and drainage maintenance)

 

Kaanapali Hillside’s elevation generally ranges between approximately 300 and 800 feet above sea level, giving many homes panoramic, unobstructed views of the Pacific Ocean, neighboring islands such as Molokaʻi and Lānaʻi, and dramatic West Maui sunsets.

 

Home Types & Architectural Styles

Properties in Kaanapali Hillside vary widely in design, size, and age, but several common characteristics define the neighborhood:

  • Single-Family Homes: The overwhelming majority of residences are detached houses, ranging from classic island ranch styles to fully updated contemporary estates.
  • Lot Sizes: Typically range from ~8,000 sq ft to 15,000+ sq ft; select parcels may exceed these sizes depending on view orientation and location.
  • Floor Plans: Floor plans vary with many homes featuring open-concept living areas oriented to capture ocean views and indoor-outdoor living.
  • Architectural Styles: Include island contemporary, Mediterranean-influenced designs, modern remodels, and custom architectural expressions that blend with the hillside terrain.
  • Outdoor Living: Covered lanais, outdoor dining spaces, private gardens, plunge pools, and spa areas are common features.

Many homes on the hillside are designed to maximize cooling trade winds and natural light, often featuring vaulted ceilings, large windows, and expansive lanais that frame the ocean and sunset panoramas.

Popular Features & Amenities in Individual Homes

  • Spacious ocean-view lanais and deck spaces
  • Private plunge pools, infinity edges, or large spa area
  • Large primary suites with ocean vistas
  • Chef-style kitchens with premium appliances
  • Ample garage and driveway parking
  • Energy-efficient upgrades such as solar power and impact-rated windows
  • Indoor-outdoor flow that leverages West Maui’s tropical climate

Unlike resort condominiums, homes in Kaanapali Hillside are typically unfurnished or semi-furnished, giving buyers the flexibility to personalize finishes and layouts.

Community & Location Highlights

Living in Kaanapali Hillside offers the perfect balance of seclusion and proximity. Residents enjoy a peaceful, residential street environment while remaining just moments from world-class amenities.

Nearby highlights include:

  • Minutes to North and South Kaanapali Beaches
  • Dining, shopping, and cultural attractions at Whalers Village
  • Championship golf at the Royal and Kai courses
  • Snorkeling, paddleboarding, and seasonal whale watching offshore
  • Easy access to commuter routes leading to Lahaina town
  • Approximately 45-minute drive to Kahului Airport for mainland and inter-island flights

Kaanapali Hillside residents enjoy both the everyday conveniences of town living and the serenity of a neighborhood that feels distinctly removed from the resort bustle below.

Lifestyle & Investment Considerations

  • Primary Residences & Long-Term Homes: Kaanapali Hillside is ideal for those seeking full-time island living with access to excellent schools, community services, and neighborhood cohesion.
  • Second Homes: The neighborhood’s tranquility and ocean views make it a favorite for second-home buyers who want a retreat near beaches, yet elevated above the coastal corridor.
  • Vacation Rental Rules: Unlike hotel-zoned properties, most homes in Kaanapali Hillside do not allow short-term vacation rentals. Buyers should confirm allowable rental use with county zoning and neighborhood guidelines before purchasing.
  • HOA & Maintenance: Some sections may have small homeowner associations for roadway and drainage maintenance but generally have lower fee structures than resort condominiums or gated enclaves.

Market Perspective

Homes in Kaanapali Hillside command strong demand due to:

  • View Orientation: Ocean and sunset views consistently drive premium pricing
  • Neighborhood Character: Established and quiet residential streets attract long-term buyers
  • Lifestyle Value: Quick access to beaches and resort activities without hotel zoning restrictions
  • Lot Depth: Larger lots provide opportunities for extensive outdoor living and private amenity spaces

Limited inventory results in competitive pricing and absorption—properties with expansive views, thoughtful renovations, and high-quality finishes often see strong buyer interest.

Stay Informed on Kaanapali Hillside Real Estate

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