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

$1,199,000
1 Beds 1 Baths 410496 MLS ACTIVE Status Honua Kai - Hoku Lani BLDG.
Experience luxury living at the stunning Honua Kai Resort in Ka'anapali. This beautifully furnished 1-bedroom, 1-bathroom residence also offers a comfortable pull-out sofa, allowing up to four guests to sleep comfortably. Additionally, it boasts new Life Proof flooring, Bosch washer and dryer, dishwasher, refrigerator, lanai furniture and new AC system. With breathtaking mountain views and a serene island setting, it is perfect for relaxing, entertaining, or enjoying your Hawaiian escape. Honua Kai delivers an exceptional resort lifestyle with an impressive array of amenities, including a state-of-the-art fitness center, three sparkling pools, five hot tubs, and the tranquil Ho'ola Spa. Dedicated concierge and valet services provide effortless convenience, while direct beach access puts the beauty of Ka'anapali right outside your door. Enjoy unforgettable evenings grilling at the resort's BBQ areas or dining at Duke's Beach House, conveniently located on property and renowned for its spectacular sunset views. With hotel zoning, this property offers an opportunity for both investment and personal enjoyment. Whether you're looking for a Maui retreat, a vacation rental investment, or the opportunity to own a piece of one of Hawaii's most sought-after resort destinations, this Honua Kai residence is an opportunity for you to embrace the island lifestyle.

130 Kai Malina Pkwy Unit SR732, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$1,295,000
2 Beds 2 Baths 410488 MLS ACTIVE Status Kihei Beach BLDG.
Experience the very best of oceanfront South Maui living at Kihei Beach #101, a beautifully renovated, hotel-zoned, ground-floor condominium situated directly on the golden sands of Sugar Beach. Thoughtfully remodeled in 2019, this spacious end-unit, two-bedroom, two-bath residence offers an exceptional blend of luxury, comfort, and investment potential with seamless indoor-outdoor living just steps from the Pacific Ocean. The open-concept floor plan features central air conditioning, in-unit laundry, luxury finishes, and a spacious chef's kitchen with an oversized island designed for entertaining family and friends. Expansive glass doors fill the home with natural light and open to a private covered lanai with direct access to the heated swimming pool, oceanfront lawn, barbecue area, and miles of sandy beachfront beyond. The desirable ground-floor location allows you to walk directly from your lanai to the beach, creating the ultimate Maui indoor-outdoor lifestyle. Offered fully furnished and turnkey, subject to seller exclusions, the residence has an established vacation rental history and is located within one of South Maui's desirable hotel-zoned oceanfront communities, making it ideal as a personal beachfront retreat, luxury second home, or continued income-producing vacation rental. Kihei Beach Resort is a boutique oceanfront property fronting spectacular Sugar Beach, where nearly six miles of uninterrupted shoreline invite morning walks, paddleboarding, kayaking, swimming, seasonal whale watching, and unforgettable sunsets. Its convenient South Maui location provides easy access to Wailea's championship golf courses, world-class resorts, Makena's beaches, Maalaea Harbor, shopping, dining, and Kahului Airport. Whether you're seeking a legacy family beach home, a luxury island escape, or an established vacation rental investment, Kihei Beach #101 offers a rare opportunity to own an irreplaceable piece of Maui's coastline where exceptional beachfront living, proven rental performance, and long-term ownership value come together.

36 S Kihei Rd Unit 101, Kihei

Listing courtesy of Compass-W.

$1,557,000
2 Beds 2 Baths 410487 MLS ACTIVE Status Wailea Palms BLDG.
Welcome to Wailea Palms 2703, FULLY FURNISHED and move-in ready, spectacular and renovated ground-floor 2 Bedroom, 2 Bath residence in one of Wailea's most sought after gated communities. Offering zero stairs from the parking area to the unit. 2703 combines effortless convenience with refined island living. Thoughtfully designed floor plan flows seamlessly through Fleetwood sliding glass doors to a large covered wrap around lanai with ocean views and lush tropical landscaping, perfect for indoor-outdoor living and entertaining. Recent upgrades include fully remodeled bathrooms (2025), travertine flooring, brand new fans and appliances throughout, custom cherry wood cabinetry, and handcrafted built-ins by Olivery Woodworking - including a custom breakfast nook, dining table, bathroom cabinetry, and custom glass and wood doors. A built-in Murphy bed in the second bedroom adds flexibility, allowing the space to function as either a guest suite or home office. Every detail has been designer curated, including designer furnishings, décor, accessories and kitchenware. Truly turn-key. Wailea Palms amenities include a spectacular OCEAN VIEW pool and spa, fitness center, BBQs, and beautifully landscaped grounds. Just moments from Wailea's world-class beaches, golf courses, luxury resorts, fine dining, The Shops at Wailea and the scenic Wailea Beach Path, this exceptional residence offers the privacy, quality, and lifestyle that make Wailea one of Maui's premier destinations. Call to schedule a showing!

3150 Wailea Alanui Dr Unit 2703, Kihei

Listing courtesy of Keller Williams Realty Maui-Ka.

$20,500,000
3 Beds 4 Baths 410482 MLS ACTIVE Status
Welcome to the quintessential Maui oceanfront estate, ideally situated on Keawakapu Beach—widely regarded as one of Maui’s most beautiful stretches of sand. This timeless Hawaiian residence embraces its unrivaled setting with approximately 2,500 square feet of covered outdoor living space, perfectly suited for beachfront lounging and entertaining. Designed with architectural integrity and island sensibility, the home features traditional Dickey rooflines topped with black glazed tiles imported from Japan. A electronic gate opens into a private, walled compound that includes the main residence, a detached two-bedroom guest cottage (Ohana), a two-car garage with workshop, and a beautifully landscaped courtyard with a pool and spa. The single level main home offers soaring 16 foot ceilings in the great room with a working fireplace serving as the centerpiece, complemented by an open-concept kitchen and expansive glass walls that frame breathtaking ocean views while preserving privacy. The main residence includes three bedrooms and four bathrooms, all designed with ease of access and comfort in mind. The detached two-bedroom, one-bath Ohana is finished to the same high standard, ideal for visiting family or guests. Set on 0.8 acres, the estate flows seamlessly from lush lawn to the beach, where a protective lava rock point cradles the property and collects soft white sand along this dramatic, crescent-shaped shoreline—one of the largest and most coveted on the island. A rare opportunity to own a true legacy property on Maui’s finest beachfront. **Disclosure** Some pictures have been Virtually Re-Staged and noted.

3146 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$26,000,000
3 Beds 5 Baths 410474 MLS ACTIVE Status
What can money buy that time can't? Six years of thoughtful planning, design, construction, and mature landscaping, ready today. Spanning 4.35 acres across two adjoining parcels, including a rare buildable two-acre lot, 215 & 217 Plantation Club Dr. is a wellness retreat for those who value privacy, health, and the freedom to disconnect. Perched 325 feet above sea level in a lush West Maui microclimate and sited according to Chinese feng shui principles, the estate captures panoramic views of Moloka'i, Lana'i, and the Au'au Channel, where humpback whales winter and calve. Across the road is Honolua Bay, Maui's iconic surf break, with the Plantation Golf Course 200 yards away. Recovery is built into the architecture. The primary suite features a 15-foot rain shower and soaking tub, while the pool house includes a Pilates studio and aromatherapy steam shower. Outside, a heated 22-by-60-foot saltwater pool, spa, and cold plunge create a daily ritual of restoration. This isn't a house with amenities. It's a private wellness compound with bedrooms attached. More than 90 fruit trees across 16-plus varieties are irrigated by a private cistern, complemented by an outdoor kitchen with a wood-fired pizza oven. A detached five-car garage with high-lift doors accommodates 10 vehicles. Fully furnished in Plantation Estates near Kapalua Resort, beaches, golf, and dining. Offered below replacement cost - an opportunity that can't be recreated today.

215 Plantation Club Dr, Lahaina

Listing courtesy of Compass-W.

$2,700,000
3 Beds 5 Baths 410469 MLS ACTIVE Status
This phenomenal slice of paradise was appraised for $2,700,000.00 (Listed price), in July 2026. It consists of 5.05 Splendid acres on an AG Zoned parcel, in the heart of Haiku. Emerald green pastures dotted with various fruit trees, flowers, and room for horses, sheep, goats, chickens, etc. This Legacy property is as close to heaven on earth, as can be. The owner/ builder imagined everything with a purpose, and it shows in the quality upgrades throughout the Main home and property. Lychee, coconut, mango, mountain apples, and avocado trees are a few of the trees that frame the acreage, and make for wonderful eating. The Lychee were planted so that they would stagger bloom every other year. The flowers are a variety of Hibiscus, Gardenias, and several other fragrant, and tropical treasures!! The farm also features a small barn, and extra tool shed. Construction includes vaulted ceilings, a large covered exterior living area, featuring a kitchen, great space to watch sports, and large windows taking in the verdant lawns, in addition, another fabulous wrap around lanais, with yet another barbeque covered lanais. This owner built main home, boasts everything you need to run a farm/ranch, and then some. The 4064 sq. ft., Main home is a large single- story home, constructed on post and piers. The home is on a slight hillside, permitting for a large under- home work shop, providing both power, and water, as well as an extra half bath, for the workers. Main home features multi-generation living. It boasts 2 large kitchens, 3 En Suite Bedrooms, an extra full, and half bath, a media room, library, a large den, formal full bar, and separate office. All the bedrooms are equipped with TV access. Included are several large aquariums, which will remain in the main home. The sellers have installed an electric gate for access to the main home. There is a separate entrance to the cottages. There are also two fully permitted 1000 square foot, 3 bed 2 bath - cottages. One of the cottages features a 2-car garage. These cottages are tenant occupied, and are now rented on a month- to- month basis. The main home, and one of the cottages are equipped with Photo voltaic panels. The property is on one water, and electric meter. Qualified buyers may arrange to view the property, keeping in mind, that a 48 hour -notice is required to view the Ohanas. The property is being sold AS IS. The current Owner/Trustee was not on site when the property was built. The Trustee who built it, passed away in 2016, so Seller’s Disclosure will be limited.

1525 Kaupakalua Rd, Haiku

Listing courtesy of Coldwell Banker Island Prop-KP.

$7,800,000
3 Beds 4 Baths 410468 MLS ACTIVE Status
Brand New Construction | Luxurious Estate Living at The Ridge, Wailea Welcome to a sprawling, brand-new estate at The Ridge in Wailea, where every detail has been curated for elevated island living. Terraced landscaping and hand-set rock walls guide you toward the hilltop entrance, offering a dramatic first glimpse of the infinity pool as you arrive. Step through the substantial solid walnut wood pivot door, flanked by bilateral side windows that flood the entry with natural light. Inside, the open-concept kitchen, dining, and living areas flow seamlessly past disappearing Fleetwood doors to a spacious lanai anchored by an infinity pool and spa. Beyond, sweeping views stretch across West Maui, Lanai, Kahoolawe, and Molokini. The lanai wraps to the south into an entertainer's dream — a full bar and BBQ area complete with a hidden large-screen TV — while a pool bath with full sauna delivers a true resort-at-home experience. The chef's kitchen is outfitted with a premium Thermador appliance suite, shaker and flat-front cabinetry, and granite countertops, plus a built-in white wine cooler and a sleek, temperature-controlled red wine storage room. Rounding out the first floor: a two-car garage, a large laundry room, a modern half bath, and a primary suite with direct lanai access, smart shower, smart toilet, double vanity, and a private outdoor soaking tub. Ascend the dramatic floating staircase, set off by a sleek modern chandelier and stone accent walls, to discover a hidden office and an open den with lanai access leading to an outdoor gathering area centered on an elegant fire pit — all framed by more sweeping ocean views. Two additional bedrooms complete the second floor: a guest suite with ensuite bath and lanai access, and a second primary suite featuring lanai access, a walk-in closet, an oversized smart shower, and a top-filling soaking tub. Home is offered fully furnished and situated on the highest elevated lot in Wailea. Quality and luxury abound — your perfect Wailea oasis awaits.

22 Halapa Pl, Kihei

Listing courtesy of Hawaii Life (W).

$2,500,000
410448 MLS ACTIVE Status
Located on the mild Southern side of Hana, 176 acres, just 4 miles from Hana Village, & close to white sand Hamoa Beach and Waioka(‘Venus’) Pool... Consistent annual rainfall delivered by gentle trade winds and conveniently distributed throughout the year... Pasturage along Hana Highway with large & spaced mature shade tree canopies spread above accessible forest-floor foliage.... Pukuilua Stream(intermittent) threads through the center of the Land, originating high in the forest reserve of Waihoi Valley. A place of traditional agriculture, followed by sugar cultivation, and most recently cattle ranching...With diverse possibilities including residential use, mixed-use agriculture, livestock pasturage, tropical flower cultivation, fruit tree orchards, organic farming, forestry, hunting, and permaculture...Along with the potential for restoring native habitats and supporting conservation efforts, and more...A personal place of refuge with sustainable, self-sufficient land use. Average annual rainfall is reliable for water catchment. In the Hana region, water wells are a proven, reliable source of abundant groundwater. Convenient access, with 4 gates opening to Hana Highway which meanders along the Hana Coast close to the shoreline. Electrical, phone, and internet lines run alongside the highway in front of the property. Importantly, the land title of the entire 176 acres is officially registered with the Land Court of Hawaii, providing gold standard-like title security and a reliable store of value.

Hana Hwy, Hana

Listing courtesy of Hugh Starr & Co LLC.

$13,300,000
5 Beds 3 Baths 410440 MLS ACTIVE Status
33 Hana Highway | An Iconic Legacy Estate on Maui's North Shore There are properties that come to market, and there are properties that define a coastline. Welcome to 33 Hana Highway, an extraordinary beachfront estate in the heart of Paia, offering an exceptionally rare 145 linear feet of pristine white sand beach frontage along one of Maui's most celebrated shorelines. Offered at its July 2026 appraised valued of $13,300,000, this is more than a home—it is an irreplaceable legacy estate where the true luxury lies in the land, the shoreline, and the privilege of ownership. With an unparalleled connection to the Pacific, the residence embraces the timeless character of Maui's North Shore. Thoughtfully designed to complement its spectacular setting, the home captures the relaxed elegance that has long defined Paia—a place where sophistication is measured not by excess, but by authenticity, privacy, and an effortless indoor-outdoor lifestyle. Expansive lanais, light-filled living spaces, and panoramic ocean vistas invite year-round entertaining, quiet reflection, and unforgettable gatherings with family and friends. Beyond the residence, the grounds unfold into a remarkable oceanfront sanctuary framed by mature tropical landscaping, generous lawn areas, and direct access to an expansive stretch of soft white sand. With 145 feet of linear beachfront, the property commands a presence that is increasingly impossible to replicate. This remarkable shoreline offers an extraordinary sense of space, privacy, and permanence rarely found in Hawaii's oceanfront market. Located just moments from the vibrant charm of Paia Town, owners enjoy effortless access to award-winning restaurants, artisan boutiques, renowned galleries, world-class surfing, and the relaxed rhythm that has made Maui's North Shore one of the world's most desirable coastal destinations. Here, every day begins with sunrise over the Pacific and ends with the sound of waves meeting the shore. Properties of this significance are seldom offered. As available beachfront continues to diminish, estates with substantial sandy frontage have become true generational holdings—assets that are acquired with intention and passed forward with pride. Whether preserved in its timeless island character or thoughtfully reimagined into a world-class coastal residence, the intrinsic value will always remain rooted in what can never be recreated: the land, the location, and the extraordinary shoreline. Property Highlights • Recently appraised at $13,300,000 • Approximately 145 linear feet of pristine white sand beach frontage • Exceptional oceanfront estate in the heart of Paia • Expansive Pacific Ocean and coastline views • Authentic island architecture designed for seamless indoor-outdoor living • Mature tropical landscaping and spacious beachfront grounds • Direct access to one of Maui's most desirable sandy beaches • Minutes from Paia's acclaimed restaurants, boutiques, galleries, and North Shore lifestyle • A truly rare legacy estate with enduring generational value Some homes are built. Others become part of Hawaii's history. 33 Hana Highway is one of the few addresses where legacy begins at the shoreline. LLC Member holds an ownership interest in the property. Member is an inactive Realtor in the State of Hawaii.

33 Hana Hwy, Paia

Listing courtesy of The Agency Maui.

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