Kaan Hillside Homes with Fee Simple Land tenure

Welcome to Kaan Hillside, a hidden gem nestled in the heart of Lahaina, Maui. This charming neighborhood offers a unique blend of tropical paradise and serene living, making it an ideal locale for those seeking both relaxation and adventure. With its stunning views of the Pacific Ocean and the majestic West Maui Mountains, Kaan Hillside provides a picturesque backdrop that captures the essence of island life.

The homes in Kaan Hillside are characterized by their fee simple land tenure, allowing homeowners complete ownership of their property. This means you not only invest in a beautiful home but also gain a stake in the land, giving you the freedom to personalize your space and truly make it your own. The properties here often feature spacious layouts, lush gardens, and outdoor living areas that invite you to soak in the island's natural beauty.

One of the standout features of Kaan Hillside is its proximity to pristine beaches, vibrant local shops, and delectable dining options. Just a short drive away, you can explore the historic town of Lahaina, known for its rich cultural heritage and lively atmosphere. Whether you prefer surfing the waves, indulging in fresh seafood, or simply lounging under the sun, Kaan Hillside offers a lifestyle that caters to your every desire.

With its welcoming community, breathtaking scenery, and the promise of adventure at your doorstep, Kaan Hillside is more than just a place to live—it's a way of life. Come discover your slice of paradise in this enchanting neighborhood!

Newest Kaan Hillside Homes with Fee Simple Land tenure

$879,000

1 Beds ⋅ 2 Baths ⋅ 410183 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

This one-bedroom, one-plus-bath unit is located on Kaanapali Hillside in the Masters, an exclusive gated community featuring 2 heated pools, 2 hot tubs, 4 tennis courts, and on-site security. The warm sunsets entice you to step out onto the lawn, where you can take in sweeping ocean and neighbor island views. Located minutes from beautiful white sand beaches, restaurants, shopping, entertainment, and some of Maui’s finest golf courses.

50 Puu Anoano St Unit 503, Lahaina

Listing courtesy of Real Broker.

$1,895,000

2 Beds ⋅ 2 Baths ⋅ 410033 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Welcome to your Maui paradise at The Masters in Kaanapali. This beautifully remodeled top-floor, end-unit residence offers 1,544 square feet of thoughtfully designed living space. It features vaulted ceilings and an abundance of windows that fill the home with natural light while capturing breathtaking ocean views and spectacular sunsets year round. This spacious floor plan includes two bedrooms, two bathrooms and a flex space for home office or additional guests. The primary suite enjoys ocean views and features split vanities, a luxurious rain shower, and ample closet space. Designed with entertaining in mind, the upgraded kitchen showcases elegant quartzite countertops, custom cabinetry and Bosch/Fisher & Paykel appliances. An expansive kitchen counter is ideal for dining, serving and gathering with family and friends. The open-concept living/dining seamlessly connect to the expansive lanai surrounded by lush tropical landscaping, creating an inviting island retreat. Quality upgrades are evident throughout, including tile flooring, plush carpeting, grasscloth wall coverings and plantation shutters. There are four new Daikin mini split AC’s separately zoned in bedrooms and living area to provide individualized climate control for everyone. Residence #1602 is a standout offering within The Masters. It showcases a combination of luxury, comfort, privacy and amazing ocean views. This low density gated-community provides resort style amenities including swimming pools, hot tubs and tennis courts. Conveniently located just minutes from the best Maui beaches, world-renown golf courses, dining, shopping and entertainment. Experience the best of Maui living in Kaanapali. Contact us today for more information or to schedule your private showing and make this your new Maui home.

50 Puu Anoano St Unit 1602, Lahaina

Listing courtesy of Compass.

$1,999,000

2 Beds ⋅ 3 Baths ⋅ 409731 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Perched within the prestigious Masters at Ka‘anapali, this extensively remodeled residence offers a rare combination of refined luxury, architectural volume, and breathtaking views spanning the Pacific Ocean, the outer islands of Lana‘i and Moloka‘i. Showcasing one of the largest two-bedroom floor plans in the community, this exceptional home has been thoughtfully reimagined from top to bottom with state-of-the-art technology, central air conditioning, premium custom finishes, and meticulously curated design throughout. A gracious entry sequence welcomes you through an exclusive front patio and dramatic double-door entrance, creating a true sense of arrival. Inside, soaring ceilings, skylights, expansive glass, and an open-concept layout fill the residence with natural light while seamlessly connecting indoor and outdoor living spaces. The designer kitchen is both elegant and functional, featuring high-end built-in appliances, custom cabinetry, sophisticated finishes, a built-in breakfast nook, and an integrated office space overlooking the lush West Maui Mountains. Both bedroom suites are generously sized and privately situated, each offering en suite bathrooms, walk-in closets, skylights, and dramatic vaulted ceilings. A charming powder room serves guests, while additional features include a dedicated laundry room and a flexible art studio/office space ideal for remote work or creative pursuits. To the west, two spacious covered lanais capture panoramic ocean, sunset, and outer island views. The primary suite enjoys its own private lanai, while the main living lanai is designed for entertaining with a wet bar and additional storage. Every window and door throughout the residence has been replaced with top-tier, state-of-the-art systems, enhancing both aesthetics and efficiency. Offered furnished and truly turnkey, this exceptional residence is move-in ready and includes most furnishings excluding artwork. A rare opportunity to own one of the most extensively upgraded and spacious residences within one of Ka‘anapali’s most sought-after gated communities.

50 Puu Anoano St Unit 3404, Lahaina

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$1,499,000

2 Beds ⋅ 2 Baths ⋅ 409365 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Blending island charm with contemporary design, Kaanapali Masters #901 offers a refined and effortless take on resort living. Clean lines and a soft, neutral palette create a sense of understated elegance, while large windows frame lush tropical greenery and spectacular views of the shimmering Pacific beyond. Fully renovated in 2023, this residence is being offered furnished and presents a turnkey opportunity to step into a home that feels both polished and welcoming. The kitchen and living areas are thoughtfully designed for both entertaining and everyday comfort, creating a natural, open flow throughout the home. The primary suite enjoys spectacular ocean views, while the secondary bedroom is set within a well-manicured tropical garden, providing a peaceful and secluded space for guests, a home office, or that writing room you’ve always imagined. Located in Building 9 on the front line and set back from the Kaanapali Royal Golf Course, this ground-level corner residence enjoys a private, tucked-away setting within the greater community. The Masters is renowned for its ideal location along the Kaanapali hillside on West Maui and spans nearly thirty-eight immaculately maintained acres, complete with two pool areas and tennis courts. Just moments from the beach, golf, and dining, the result is a community and a residence that feels both connected and removed - an inviting retreat with a distinctly elevated point of view.

50 Puu Anoano St Unit 901, Lahaina

Listing courtesy of Island Sotheby's International Realty(L).

$1,300,000

2 Beds ⋅ 2 Baths ⋅ 409327 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

This elegant 1728 sq.ft. 2 bed 2 bath D floorplan residence offers beautiful OCEAN, ISLAND, GOLF COURSE and SUNSET VIEWS. This upstairs unit on the south end captures tropical trade winds and the large kitchen includes Corian countertops. The unit is entered through a very private interior entry. The interior is light, bright and spacious with a large master suite. High ceilings and expansive sliders lead out to a spacious lanai. The covered lanai is perfect for dining or relaxation, offering amazing views of the islands of Lana’i and Moloka’i. It is set along the Kaanapali Golf Course's 9th fairway with expansive ocean multi-island views. The Masters is a GATED community on almost 38 acres with 2 pools and hot tubs, tennis courts and tropical landscaping. This unit is easily accessible from the main entrance, but tucked away from the traffic. It is also very convenient to access the upper and lower pools as well as the tennis courts and is only minutes to the Kaanapali beaches, hotels and shops. The Masters is a pet-friendly community. Available to show on short notice.

50 Puu Anoano St Unit 2206, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$1,995,000

2 Beds ⋅ 3 Baths ⋅ 409185 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Welcome to the Masters at Kaanapali. Amazing opportunity to own the best and most spectacular 2bdr/2.5bath upper-level unit on the top row in the highly sought-after Kaanapali Hillside neighborhood. This prime location offers sweeping multi-islands, and ocean views from both lanais, and will allow you to admire the most spectacular sunsets year round. Unit #3604 has its own private bridge leading to a large double entryway, and was renovated with exquisite taste through the years. Vaulted ceilings and cherry wood flooring add to the spacious feeling you will experience when entering this unique residence. The primary bedroom features its own private lanai allowing for more privacy. This extra large floor plan was also designed with its own private BBQ on the lanai. There are 4 mini split AC's separately zoned in both bedrooms, living area and kitchen. The low density gated-community features swimming pools, hot tubs, tennis and pickle ball courts, all surrounded by lush tropical landscaping. It is located just a few minutes from the most spectacular Maui beaches, world-renown golf courses, and restaurants.

50 Puu Anoano St Unit 3604, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$860,000

1 Beds ⋅ 1 Baths ⋅ 409133 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

This lovely ground floor level, 1 bedroom, 1 bath unit features spectacular ocean views, location, and a wonderful opportunity for the buyers who may have pets. The sellers have renovated the shower as well as tiling the lanais, and made good use of the space they have enjoyed since 2020. There is also a storage closet on the lanais, as well as a hose bit, for ease of BBQ, and enjoying the outdoor life we all get to love in Kaanapali. The Masters features wonderful, spacious floor plans, which are accented by the fantastic ocean and outer island views, as well as mature tropical landscaping. There is a nice strip of lawn in front of the unit, and a short hedge, which blocks off the road/driveway view below, and allows for fantastic, panoramic, crystal- clear ocean vistas, stretching from the Islands of Lanai, to Molokai. The Masters sits on the Royal Kaanapali Golf course, allowing for a lush blanket of greenery, which is enhanced by the fantastic landscaping of the project. Most fortunate folks that own on the ground level, do so because of the pet allowance, and ease of access, for your favorite kitties, and dogs. This majestic property features 2 phases of construction, with the first phase being completed in 1987 and the second in 1989. The buildings are concrete, with double wall treated wood, and shake roofing. The project includes 198 units in 34 buildings, spread over beautifully landscaped 37.54 acres. The Masters has 2 sets of swimming pools, in which you can actually swim laps, and wonderful heated spas, tennis courts, and a citrus grove, for your margarita, or lemonade enjoyment. This is an owner-occupied unit, so showings are easily arranged with short notice. The sellers will be moving offsite, so the unit will be ready to be occupied as soon as possible.

50 Puu Anoano St Unit 3903, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$1,550,000

2 Beds ⋅ 2 Baths ⋅ 408805 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Welcome to The Masters 2204, a rare top-floor residence in one of Ka’anapali’s most coveted communities. This beautifully updated 2 bed, 2 bath home offers 1,512 sq. ft. of living with vaulted ceilings, skylights, and fresh new furnishings throughout. With a prime location you'll enjoy sweeping ocean views framed by Moloka‘i and Lana‘i, along with unforgettable sunsets, seasonal whale watching, and star-gazing from your spacious, tiled lanai overlooking the Ka’anapali Golf Course. Recently refreshed this turnkey unit features a stunning kitchen with custom white-oak cabinetry, granite countertops, stainless steel appliances, and gorgeous inlaid maple and tigerwood flooring. The open-concept living and dining areas flow seamlessly to the lanai for true indoor/outdoor living. The primary suite includes a king bed, office nook, dual closets, and a beautiful ensuite with travertine finishes, walk-in shower, jetted tub, and custom vanities. The guest bedroom features a queen bed and an elegant custom cherry closet system, with an updated full bath nearby. Set on 38 acres of manicured grounds, The Masters offers resort-style amenities including 2 pools, 2 hot tubs, 4 tennis/pickleball courts, and easy access to Ka’anapali Beach, Black Rock, and Whalers Village. A private covered parking stall and peaceful hillside setting add to the ease and comfort of this pet-friendly community. Move-in ready, impeccably maintained, and perfectly positioned, the Masters 2204 is West Maui living at its finest.

50 Puu Anoano St Unit 2204, Lahaina

Listing courtesy of Real Broker.

$1,295,000

2 Beds ⋅ 2 Baths ⋅ 408634 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

You simply must come by and look at this fabulous ground floor unit. Prepare yourself to be happy from the moment you walk through the front door if this wonderful home. The seller recently replaced the shower in the guest bath, and spa tub in the Main bath, painted and furnished the unit completely. It is a shiny star, very turn key, and ready for you to bring your suit case, and move in. The seller specifically selected this ground floor unit, as it offers several wonderful amenities. The orientation of building 17, is towards the island of Molokai, with additional views to the island of Lanai from the side windows included this corner unit. Perfect for pet owners, this building is one of the most private, with a huge, majestic Mokey Pod Tree with a tall canopy, providing afternoon shade, for those Maui Sunsets. The Main Suite faces the ocean view, along side the living room. It has access to the wide lanais through sliding doors. It also had windows featuring the view looking across the coffee farms to the costal beaches towards Kapalua. The corner location also allows for extra windows along the kitchen, and living room, which face directly towards the white sand, and crystal clear South Kaanapali Beach. The Masters at Kaanapali is gated, and has always boasted fantastic ocean and outer island views. Enhancing the luxury of this 37 plus acres of tropical bliss, is that is it also located directly on the Royal Kaanapali Golf Course. The Masters was built in 2 phases, so you have 2 pools, including spas, tennis courts, a citrus tree area, and beautiful, mature, tropical plantings throughout. The unit is currently vacant, and easily shown to qualified buyers.

50 Puu Anoano St Unit 1707, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$950,000

1 Beds ⋅ 1 Baths ⋅ 406864 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Oceanview opportunity available in the top row of the Masters at Kaanapali. This updated, partially furnished one bedroom, one bath can be yours for below the current tax assessed value. Two spa like pools to enjoy, tennis and pickle ball courts, well-manicured grounds. Live like you are on vacation. Enjoy Kaanapali Resort: white sand beaches, great restaurants, beach activities, nightlife, Hawaiian luaus, while having your private own home to escape to when you want to enjoy peace and tranquility. Check out the matterport tour: https://my.matterport.com/show/?m=Lfdo9vyAeGp&play=1&brand=0&mls=1& Call your Realtor today as this opportunity will not last long. Artwork, bedroom furnishings, entry table, lamps and personal effects excluded from the sale.

50 Puu Anoano St Unit 3905, Lahaina

Listing courtesy of Lowson & Associates.

$925,000

2 Beds ⋅ 2 Baths ⋅ 406273 MLS ⋅ Fee Simple Tenure ⋅ Masters BLDG.

Lowest priced two bedroom unit in this exclusive resort style neighborhood. Beautiful ground floor condominium at the Masters---Kaanapali's most desired property, with breathtaking ocean views, gated entrance, and ideal location on West Maui, close to Kaanapali beach, golf course, world famous dining and shopping. Enjoy resort living with tropical breezes, swimming pool, tennis courts, pickle ball courts and incredible sunset views. Ideal location - corner end unit on ground floor level. Enjoy sunset and ocean views from main living areas and expansive lanai. An open-concept floor plan meticulously engineered to maximize natural light and capture refreshing tropical trade winds. Well-appointed living spaces providing excellent separation between the primary suite and guest accommodations. Low density property, quiet and peaceful.

50 Puu Anoano St Unit 3901, Lahaina

Listing courtesy of Maui No Ka Oi Properties.

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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.