The Masters Real Estate Search

The Masters Properties for Sale

The Masters at Kaanapali Hillside is a picturesque, gated community that sprawls across 42 acres in Lahaina. Established in 1991, The Masters holds some of Kaanapali’s most notable and desirable real estate, as the community does not permit vacation rentals, and residents must own and occupy. Along with that unique form of privacy, The Masters also features amenities like two swimming pools, four tennis courts, and a location just minutes from Kaanapali Beach.

The Master real estate at Kaanapali presents homebuyers with a curated selection of properties from which to choose, encompassing the top of Kaanapali Royals Golf Course. The community is comprised of under 200 luxury condos that showcase maple, granite, and bamboo details. The Masters golf condos in Kaanapali are discoverable with between one and three contemporary layouts and unquantifiable commodities like tranquility and privacy. If you are interested in purchasing one of The Masters condos for sale in Kaanapali, please contact us today.

Our website features the best The Masters real estate search for homes, condo, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest The Masters Properties for Sale

$1,325,000
2 Beds 2 Baths 408131 MLS ACTIVE Status Kaanapali Royal BLDG.
Situated within the gated Ka'anapali Royal community on the Royal Ka'anapali Golf Course and just across from Whalers Village, this well-maintained residence offers an exceptional blend of privacy, convenience, and true resort living. Residents enjoy the unique Ka'anapali golf-cart lifestyle, providing easy connectivity throughout the resort to beaches, dining, shopping, and recreational amenities. Unit F-202 is a generously sized two-bedroom, two-bath condominium featuring approximately 1,534 square feet of interior living space along with a substantial 495-square-foot covered lanai. Located on the preferred middle level with a northwest orientation, the home overlooks the community pool and beautifully landscaped tropical grounds while benefiting from natural light and cooling tradewinds. The interior reflects pride of ownership and thoughtful updates throughout. The kitchen is appointed with granite countertops, stainless steel appliances, and a French-door refrigerator, complemented by porcelain tile flooring in the entry, kitchen, and dining areas. The living room and bedrooms feature newer carpeting, creating a comfortable and inviting atmosphere. Both bathrooms include Corian countertops, Kohler water-efficient high-seat toilets, and clean, timeless finishes. The open living and dining layout extends seamlessly to the oversized covered lanai—an ideal space for outdoor dining, entertaining, or relaxing while enjoying peaceful garden and pool views. Ka'anapali Royal offers residents a resort-style pool and spa, BBQ and gathering areas, covered decks, and meticulously maintained grounds—all moments from world-famous Ka'anapali Beach, championship golf, and the full array of resort amenities. The property has a proven track record as a vacation rental and continues to perform well, offering flexibility for full-time living, part-time use, or income generation. Offered furnished with select exclusions.

2560 Kekaa Dr Unit F202, Lahaina

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$3,250,000
3 Beds 4 Baths 408112 MLS ACTIVE Status
It’s time for you to own your escape to this four-acre rural-zoned property on Maui's North Shore. Wake to the sound of the warm trade winds gently swaying the trees. Stroll in your expansive yard picking fresh fruit to complement your morning smoothie. Sit with your favorite book in your treehouse perched over a lush forest, dappled with sunshine. Catch a rainbow and end your day soaking in your outdoor bath, watching the sun set. Your idyllic Maui escape is ready: 965 Hog Back Road. At the end of a country road, tucked behind a majestic Royal Poinciana tree, sits a true North Shore treasure. Originally designed by renowned Maui architect Harry Rice and now reborn as a mid-century modern retreat, the home is elegantly enveloped by more than four acres of lush, private gardens. Light-filled living spaces open to expansive lanais and a spa-like outdoor bath featuring a 72” concrete soaking tub and custom shower. The gourmet kitchen boasts a 48” Hestan gas range, paneled Hestan refrigerator, European-style cabinetry, and a dedicated pantry/prep area. The 3,100 sq. ft. home features 3 spacious bedrooms, each with a luxurious ensuite bath, plus a separate upgraded cottage ideal for guests. A custom eucalyptus spiral staircase and handcrafted details throughout accentuate the classic Maui roots. This property features language in its bylaws stating that the property can be further CPR'd unilaterally; this can be a large benefit, especially since it is zoned rural half-acre. Mature fruit trees, peaceful walking paths, and a treehouse overlooking the forested gulch create a private, retreat-like setting. All the home's amenities and features, accompanied with North Shore conveniences, make this a truly unique architectural treasure. This is an A unit of a CPR.

965 Hog Back Rd, Haiku

Listing courtesy of Hawaii Life (W).

$4,495,000
2 Beds 2 Baths 408086 MLS ACTIVE Status Wailea Point I Ii Iii BLDG.
Wailea Point Beach Condo 2904 is designed for comfort and relaxation. Wailea Point! South Maui's most elegant, luxurious, and private community. This premier oceanfront enclave's luxury and casual sophistication marries the divine setting with dramatic ocean views. Enjoy the premier Maui lifestyle in this private, spacious, fully furnished 2-bedroom, 2-bath residence in beautiful Wailea Point. High ceilings, huge picture windows, and beautiful finishes create the perfect setting for comfortable living and memorable entertaining that flows from spacious interiors to oceanview lanais. The spacious living room features large windows that let in plenty of natural light and offer panoramic views of the beach and ocean. Brand new window installation just completed, featuring a beautiful mitered glass bay window with custom automatic roll-down shades. The extraordinary, panoramic views look from the surf and sand of Polo Beach, across the ocean to the islands of Lanai, Kahoolawe, & Molokini, down the coast to Makena, and up to the summit of Haleakala. The kitchen features exceptionally fine Koa cabinets and high-quality appliances, including an oven, microwave, refrigerator/freezer, dishwasher, and ample cabinet space. The covered lanai is the perfect spot to savor a cup of coffee in the morning, enjoy the sunrise, or barbecue in the evening while taking in the expansive ocean views, sunsets, whales, dolphins, and seabirds. Wailea Point is a low-density 26-acre oceanfront property with impeccably landscaped common areas and top-quality amenities. 24-hour security, three swimming pools, a lap pool, two spas, BBQ pavilions, a fully equipped fitness center, lighted tennis, paddle tennis, and pickleball courts. Wailea Point is conveniently located between Wailea Beach and Polo Beach.

4000 Wailea Alanui Dr Unit 2904, Kihei

Listing courtesy of Coldwell Banker Island Prop(P).

$24,500,000
5 Beds 6 Baths 408059 MLS ACTIVE Status
Experience the pinnacle of oceanfront luxury in this stunning, 5 bedroom, 5 bath, plus 2 half bath, 7,244 sq. ft. home estate. This over a half-acre property is located within the ideal stretch of Keawakapu Beach, offering unparalleled access to Maui’s most coveted shoreline. This architectural triumph blends contemporary elegance and convenience with the island’s natural beauty, creating a private sanctuary of sophistication and rare serenity. This estate features 5 spacious en-suite bedrooms, multiple areas for relaxed socializing, and a seamless indoor-outdoor flow that embraces the home’s stunning pool courtyard and oceanfront experience. Every room gifts an extraordinary vantage point of paradise – between sweeping ocean views in three master suites or tranquil poolside perspectives from the guest suites. At the heart of the home, the expansive pool and courtyard form a striking focal point, linking the media room, main entry, and living areas in perfect harmony. A private poolside retreat ensures both security and discretion, ideal for intimate gatherings or large-scale entertaining. Landscaped gardens with numerous palm trees and second-level sundecks off the guest suites provide elevated spaces to soak in a front seat view of unforgettable sunsets. A spacious oceanfront lawn offers ultra-privacy, featuring a fire pit that creates an inviting ambiance, shielded from public view and accessible only through a discreet, gated beach entrance. Whether you seek a primary residence, a lavish vacation home, or an island retreat, this estate is designed for those who desire premium beachfront living with an ultimate feel of privacy. A rare opportunity to own the most memorable oceanfront lifestyle in Maui.

3254 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$3,550,000
2 Beds 3 Baths 408042 MLS ACTIVE Status Kapalua Ironwoods BLDG.
Beautifully remodeled in 2022, this single-level ocean-view residence at the Ironwoods captures the effortless luxury and serenity of Kapalua living. Custom sliding pocket doors open to an expansive lanai with sweeping views of Honolua Bay and the lush fairways of the Kapalua Bay Course. A dramatic wall of ocean-facing windows pulls the coastline into your living space, filling the home with golden light and that unmistakable Kapalua magic. Inside, the residence blends warmth with refined sophistication—pristine white oiled oak flooring, custom Schüller cabinetry, Monte Cristo granite countertops, state-of-the-art Bosch appliances, intuitive smart-home integrations, and thoughtfully curated lighting throughout. Newly installed energy-efficient Pella windows enhance the bright, airy ambiance that flows through the home. The primary suite serves as a private retreat, complete with a spacious bath suite and a luxurious granite steam shower. One of the rare Ironwoods offerings, this residence features a fully private, single-level entry with direct access from the enclosed garage—an exceptional advantage for those who value ease, accessibility, and complete privacy. Nestled within the exclusive gated community of the Ironwoods, residents enjoy resort-style amenities including a fitness center, tennis courts, and a solar-heated pool and spa—set across 9.2 acres of meticulously manicured grounds. A nearby walking gate provides effortless access to the Kapalua Coastal Trail, world-class beaches, and the breathtaking shoreline that defines this extraordinary region. Offered fully furnished, this residence is a serene, turn-key ocean-view haven in one of Maui’s most coveted enclaves.

62 Ironwood Ln Unit 62, Lahaina

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

$9,900,000
3 Beds 4 Baths 408037 MLS ACTIVE Status
BEING WELL. For those that crave a holistic environment that nourishes the mind, body, and soul, in a tropical, private Hawaiian environment, the estate at 223 Plantation Club Drive is the home for YOU. Extremely private & serene, this extraordinary 2.18-acre sanctuary consists of mature luscious tropical landscaping with over 40 fruit plantings while being steps away from the 15th & 17th holes of the Kapalua Plantation Golf Course. The WELLNESS amenities include an ALL-IN PLUNGE® (cold water immersion), sauna, resort-sized pool & spa (complete with slides, pirate-themed smoke & lighting features), fire-pit, Koi-pond, vegetable-planter boxes, steam shower, workout facility and billiard table. This sprawling, single-level estate consists of 3 bedrooms, 3 bathrooms, and 1 1/2 half-bath spread across 5,366 living square feet. The residence showcases impeccable craftsmanship, state-of-the-art upgrades, and refined details throughout. Inside, discover 64 feet of motorized pocket doors that disappear into the walls, seamlessly blending the interior with over 2,000 square feet of covered lanai. The open floor plan features soaring 12-foot ceilings, two elegant living spaces, a dining area, a private office, a wine cellar, and two fireplaces. The gourmet kitchen boasts double islands, a new 48” Wolf range, and a Wolf grill at the outdoor bar, ensuring effortless entertaining. Two additional guest suites, all with 10-foot ceilings, provide ample accommodation for family & visitors. Outdoors, the estate’s transformation is nothing short of spectacular. The completely renovated pool features a grotto, two water slides, a 7-foot waterfall with a jumping rock, and an adjoining spa, creating a resort-like atmosphere. Hundreds of strategically placed landscape lights illuminate the lush grounds, koi pond, and tropical gardens, turning the property into a breathtaking paradise after sunset. The fully automated Savant system enhances the experience, providing control over nearly every aspect of the home, from lighting and sound to the 10 tiki torches and more. Additional features include a sprinklered orchard with over 40 fruit trees (bananas, avocado, mangos, lemons, limes, oranges, grapefruits, mountain apples, starfruit, papayas & more), an inviting outdoor shower, a spacious three-car garage with a home gym, and ample storage. The Plantation Estates of Kapalua is one of the most prestigious & exclusive golf-course gated communities in the Hawaiian Islands. This agricultural-zoned community consists of 53 Plantation Estates & 50 Honolua Ridge (phase 1 & 2) parcels. The community is home to the PGA’s annual Sentry Tournament of Champions Invitational and the Plantation Restaurant. Owners have easy access to the Kapalua Resort amenities including world-renowned D.T. Fleming Beach, Honolua Bay, whale watching, swimming, golf, hiking, Kapalua Tennis Garden / Pickleball, Kapalua Zipline, The Montage massage/spa & the incredible shopping & fine-dining experiences. The quintessential luxury retreat, the estate at 223 Plantation Club Drive inspires you to attain a level of relaxation that YOU desire and deserve. YOUR Time Is Now.

223 Plantation Club Dr Unit 14, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$8,395,000
5 Beds 4 Baths 408032 MLS ACTIVE Status
Also listed in Vacant Land Classification MLS #408615. This listing is a Residential CPR. Set across 3.219 acres in a quiet stretch of Makila Ranches, Launiupoko, this estate will bring together clean architecture, generous outdoor living, and a cohesive layout that feels open yet defined. With 5 bedrooms, 4 bathrooms, and 4,590 square feet of living area, the home offers a thoughtful balance between shared gathering spaces and private bedroom retreats. A covered entry leads into the Great Room, where wide openings frame the elegant reflecting pools, spa, and infinity-edge pool set directly along the central sightline of the home and positioned to take in the stunning ocean views. This sculptural outdoor centerpiece is complemented by 1,646 square feet of covered lanai spaces that stretch across the rear of the residence, creating a fluid style of living that suits the temperate Hawaiian climate. The Great Room spans approximately 34 feet in length and 51 feet in width, creating a wide, airy central living area. These dimensions give the room an impressive presence at the heart of the home, allowing for generous seating arrangements and a natural connection to the outdoor living spaces. The kitchen blends clean lines with a layout designed for easy gathering. A generous island offers ample workspace for cooking or casual conversations. Appliances include a 48-inch range, a matching 48-inch refrigerator/freezer, dedicated wine storage, and a walk-in pantry tucked neatly off to the side. The design keeps the central living areas light and open while feeling both polished and practical, creating an inviting centerpiece that brings everyone together. The five-bedroom layout is arranged in distinct wings for a sense of privacy throughout. Each of the home’s five bedrooms is designed as a quiet retreat, arranged across separate wings. The primary bedrooms feature walk-in closets, private bathrooms, and private lanai spaces with outdoor showers. The garage offers 945 square feet of covered parking for up to three cars and ample storage space. Set against the green backdrop of the West Maui Mountains and the expansive ocean and outer-island view, Makila Ranches 6A pairs modern simplicity with expansive single-level living, giving the property an easy, graceful presence that fits beautifully into the landscape.

391 Haniu St Unit Lot 6A, Lahaina

Listing courtesy of Welcome Hawaii Properties.

$285,000
2 Beds 2 Baths 408012 MLS ACTIVE Status Ke Nani Kai BLDG.
Experience the beauty of Moloka! This west end from this wonderfully updated 2-bedroom, 2-bathroom Ke Nani Kai condo featuring sweeping, unobstructed ocean views! Every inch of this unit has been thoughtfully remodeled with attention to detail, creating a warm and inviting Hawaiian-inspired retreat. Enjoy a spacious private lanai overlooking the coastline with panoramic views all the way to O?ahu—the perfect place to watch winter whales, vibrant sunsets, and the ever-changing colors of the Pacific. Inside, the remodeled kitchen showcases a cohesive tropical ambiance with beautiful tiled countertops, stainless steel appliances, a stylish tiled backsplash, and a convenient breakfast bar. The condo features tile flooring in kitchen and bathrooms and wood flooring throughout the rest for easy maintenance and a cool, clean aesthetic. Both bathrooms have been fully renovated with matching finishes, continuing the home’s thoughtful Hawaiian design theme. Most Hawaiian-style furnishings will remain with the condo, offering a turnkey option for buyers. Additional upgrades include an on-demand hot water heater and a solo washer/dryer unit, adding to the convenience of full-time or vacation living. Just outside your door are miles of scenic walking and running trails leading to three of Molokai’s most iconic beaches: Kepuhi Beach, Papohaku Beach, and Make Horse. Ke Nani Kai provides outstanding amenities, including a private resort-style pool, in-ground hot tub, gated tennis and pickleball courts, a BBQ pavilion, an owner’s garden, and beautiful landscaped grounds. Whether you’re looking for a peaceful island home, a vacation escape, or a ready-to-go rental, Ke Nani Kai 242 is a stunning opportunity offering upgrades, comfort, and spectacular ocean views in one of Molokai’s most picturesque settings.

50 Kepuhi Pl Unit 242, Maunaloa

Listing courtesy of Molokai Vacation Properties.

$930,000
3 Beds 2 Baths 407980 MLS ACTIVE Status
Discover a modern and versatile home in the heart of Wailuku, completely reimagined in 2025 and designed to accommodate a variety of living arrangements. Whether you’re seeking a multi-generational setup, a home with rental potential, or simply extra room to live comfortably, this property offers exceptional adaptability. The residence can function as a spacious 5-bedroom, 3-bath home or be configured into two distinct living spaces. The main side offers a bright and inviting 3-bedroom, 2-bath layout, while the adjoining 2-bedroom, 1-bath area—complete with its own entrance and private yard space—serves perfectly as extended family quarters, guest accommodations, or an income-producing rental. The flexibility here is truly unmatched. Step inside to a fully refreshed interior featuring new laminate wood flooring, sleek white cabinetry with soft-close finishes, stone countertops, updated tile work, and contemporary fixtures throughout. A brand-new roof adds long-term peace of mind, and the home comes fully furnished—making your move effortless and immediate. Located just minutes from Wailuku’s shops, restaurants, schools, and essential services, this property places you close to everything while still offering the comfort of a residential island neighborhood. With nearly every feature renewed, 1590 Ono Street provides a rare opportunity to enjoy modern living in a highly convenient Central Maui setting. Move-in ready, furnished, and thoughtfully redesigned—this is a home you won’t want to miss.

1590 Ono St, Wailuku

Listing courtesy of Berkshire Hathaway Maui Prop-L.

$895,000
3 Beds 2 Baths 407981 MLS ACTIVE Status
Experience the charm and comfort of this freshly reimagined 3-bedroom, 2-bath residence with an additional office/den, offering a flexible layout ideal for modern living. Thoughtfully redesigned, the home blends contemporary updates with warm, inviting spaces—perfect for those seeking move-in-ready convenience in a central Maui location. Step inside to find a bright and welcoming lower level featuring two bedrooms, a full bathroom, a cozy family room, and a versatile den that can serve as a home office, playroom, fitness space, or guest area. The upstairs level is dedicated to the primary suite and the main living spaces, creating an elevated setting with easy flow between the kitchen, living room, and outdoor deck. From the lanai, take in sweeping vistas of Haleakala and the West Maui Mountains—an inspiring backdrop for morning coffee, evening relaxation, or weekend gatherings. The views and natural light lend an airy, uplifting feel to the upper level. Located in a highly convenient Central Maui neighborhood, this home places you just moments from schools, shopping, dining, medical facilities, and the airport. Whether commuting or enjoying day-to-day living, the accessibility is hard to beat. With no association fees, plentiful parking, and a smart layout that accommodates a variety of lifestyles, 180 Hoomoku Street is an excellent opportunity for buyers seeking comfort, functionality, and value in one of Maui’s most practical and well-situated communities.

180 Hoomoku St, Kahului

Listing courtesy of Berkshire Hathaway Maui Prop-L.

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