Maui Real Estate Search

Jude Augustine Featured Properties

$6,950,000
4 Beds ⋅ 6 Baths ⋅ 408558 MLS ⋅ Fee Simple Tenure
This exclusive opportunity is uniquely situated on a lot like no other, overlooking the 11th green of the Wailea Blue Course and positioned near the Four Seasons and Hotel Wailea. Set within a premier gated community, the home enjoys exceptional space and privacy, bordered on three sides by open areas, the golf course, and two greenway lots with a down-sloping parcel that opens first-floor views to island vistas. The light-filled interior draws you toward a very private resort-style pool and spa, protected from excess sun and wind. Indoor and outdoor staircases lead to the upper level, where a stunning 360-degree panoramic view unfolds across Lana?i, the West Maui Mountains, open fairways, Haleakala, Kaho'olawe, and Molokini. Seamless indoor-outdoor living connects both levels of the home, with every room opening to its own lanai, terrace, patio, or lawn, including common areas and guest baths. The property also offers flexibility to expand by approximately 500 square feet on each level. The formal living room features a wood-burning fireplace, white painted tongue-and-groove vaulted ceilings, and French doors opening to a covered island-view porch. The kitchen and family room flow to a 35-foot lanai ideal for daily living, sunset views, seasonal whale watching, and twice-yearly resort fireworks. A Haleakala-facing terrace offers peaceful daytime views and nighttime stargazing, while a wet bar off the pool deck supports relaxed outdoor entertaining. Four en-suite bedrooms provide private retreats with outdoor access, including a primary suite with a five-fixture bath and exceptional views. A southern orchard leads to an outdoor laundry entry, and the two-car garage includes ample storage. This is a home that is difficult to leave, wrapping you in the warmth of every aloha memory.

3977 Wailea Ekolu Pl, Kihei

Listing courtesy of Hawaii Life (W).

$6,900,000
2 Beds ⋅ 1 Baths ⋅ 409482 MLS ⋅ Fee Simple Tenure
4025 Lower Honoapiilani is an exquisite and rare 1-acre oceanfront gated estate, located in one of the world's most desirable locations, between Kaanapali and Kapalua, on the Island of Maui. This one-of-a-kind property offers dramatic sunsets year-round and seasonal whale watching. Situated west facing, the panoramic views of the outer islands Molokai and Lanai create a backdrop like no other. A rare opportunity to own one of the few prime oceanfront sites available. The property is surrounded by blue rock walls and well-maintained mature landscaping offering privacy and tranquility. The bright and opened property features an updated and charming 2-bedroom cottage with additional flex rooms. The mid-level lawn offers a leveled homesite for a main residence. Terraced lawns, and seaside trails take you to the lower grass lawn and ocean access. It's A-1 apartment zoning may offer other potential development options.

4025 Lower Honoapiilani Rd, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$6,800,000
4 Beds ⋅ 3 Baths ⋅ 407207 MLS ⋅ Fee Simple Tenure
A rare opportunity to own a gated multi-structural coastal estate with beach access just steps away. Set at the end of a quiet cul-de-sac, this versatile property offers 4 bedrooms and 2.5 baths, featuring warm wood floors, open floor plan, a detached 3-car garage with office and bonus rooms above, and separate yoga studio. Enjoy a spa/hot tub under the stars, harvest from your own citrus orchard, and entertain guests in a setting that blends comfort and island charm. Perfect for extended family, rental income, or a private retreat. Live the laid-back North Shore lifestyle with surf, sand, and sunshine outside your door, just minutes to Paia and world-class beaches.

1050 Kapukaulua Pl, Paia

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

$6,750,000
5 Beds ⋅ 6 Baths ⋅ 409921 MLS ⋅ Fee Simple Tenure
Sunlight and ocean breezes flow through 21 feet of bi-folding floor-to-ceiling glass doors, complemented by soaring 14-foot ceilings that blur the boundaries between home and horizon. Step into this South Maui beachfront estate, where elegant stone columns welcome you to a true masterpiece. The open-concept spaces unfold effortlessly, anchored by a chef's kitchen featuring custom white oak cabinetry with an interior finish that adds warmth and depth, quartzite countertops, tumbled Belgian limestone tile accents, hand-scraped French oak flooring, professional-grade appliances, and a generous breakfast bar— the perfect hub for shared meals, laughter, and connection. A floating staircase leads upstairs to the bedrooms, where the primary suite awaits as a serene sanctuary for the soul. It includes a spa-inspired soaking tub, dual vanities, a spacious walk-in closet, and a private ocean-view lanai ideal for morning reflections. Each additional guest suite has been thoughtfully designed to soothe the senses, with layouts and features that prioritize comfort, including ensuite bathrooms for ultimate privacy. Outside, your personal coastal retreat beckons. Lounge poolside in the saltwater pool, host gatherings under a canopy of stars, or savor a cocktail as the sky blazes with sunset hues. A detached guesthouse with a full bathroom and a two-car garage offer flexible additional space, while integrated smart home technology blends modern convenience into this tranquil, soul-nourishing haven. The adjacent lot is also for sale by the same seller. (MLS #409920, 892 S Kihei Rd) and can be purchased together.

860 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$6,499,000
3 Beds ⋅ 3 Baths ⋅ 407426 MLS ⋅ Fee Simple Tenure
Set in one of Kula’s premier Upcountry locations, this nearly 4,000 sq ft single-level residence showcases modern design, seamless flow, and commanding views of Lanai, Kahoolawe, and Molokini. Clean architectural lines, high ceilings, and expansive glass walls create a sense of openness while framing the panoramic ocean views. The thoughtfully designed floor plan centers around a spacious great room that connects the living, dining, and kitchen areas to an expansive lanai, ideal for effortless indoor-outdoor living and enjoying evening sunsets. The kitchen is a contemporary showpiece with custom cabinetry, stone countertops, and top-tier appliances, designed for both form and function. The spacious primary suite, located at one end of the home, features walk-in closets, dual sinks, and a private office entrance. Two guest suites are thoughtfully placed on the opposite side of the living space, ensuring privacy and maintaining the same standard of quality as the rest of the home with upper loft areas for additional space. The home includes three bedrooms and three bathrooms, along with a 1,100 sq ft garage that includes an office and storage, and a 600 sq ft auxiliary building suitable for a studio or other creative space. This contemporary home was designed with intention where every room connects to the land, light, and views that define Kula living.

7850 Kula Hwy, Kula

Listing courtesy of Hawaii Life (W).

$6,300,000
4 Beds ⋅ 5 Baths ⋅ 409968 MLS ⋅ Fee Simple Tenure
Set on over 2 acres in Launiupoko, one of West Maui's most prestigious hillside communities, this stunning single-story estate offers 4 bedrooms, 4.5 bathrooms, and 3,675 square feet of refined Hawaiian contemporary living. Perched on a breathtaking West Maui hillside in prestigious Launiupoko, this luxury residence boasts some of the most dramatic sunset and outer island views on the island, a resort-style pool and spa, and the kind of indoor-outdoor flow that makes every day feel like a vacation.  Arriving through a grand hardwood entry door framed by lush tropical landscaping, the foyer sets a tone of relaxed sophistication, with clean lines, Imperial plaster walls, and wide-plank Pasha Wood Lite tile underfoot. The great room opens dramatically, with walls of glass pocket doors that retract fully to merge the interior living space with the covered lanai beyond. Ocean views pour in from every angle. The seamless indoor-outdoor flow is not an afterthought here; it is the central design ethos. The gourmet kitchen is a showpiece in its own right. Custom cabinetry pairs with granite countertops and a generous center island with bar seating. A stainless range with statement hood anchors the space, while pendant lighting and a picture window framing the Pacific and the silhouette of Lanai on the horizon make this a kitchen where cooking becomes an event. The open dining area flows naturally off the kitchen, ideal for entertaining at any scale. The primary suite is a sanctuary. Sliding glass doors open directly onto the pool deck, and ocean views greet you from bed each morning. Rich oak millwork, ceiling fans, and thoughtful finishes are found throughout all four bedrooms. Step outside and the property reveals its full ambition. A resort-style lap pool stretches across the rear of the home, glowing blue against the warm Maui sky at dusk. An elevated spa sits alongside, with travertine decking, manicured tropical lawn, and swaying palms completing the scene. The private pool cabana adds a layer of luxury rarely found at this price point, offering a full bath and outdoor shower for seamless poolside living.  A built-in outdoor kitchen and covered lanai dining area make alfresco entertaining effortless, with front-row sunset views over the ocean and the outer islands of Lanai and Molokai as the backdrop. Owned photovoltaic solar, solar water heating, central air, and a 3-car garage round out an estate that performs as beautifully as it looks. This is Launiupoko living at its absolute finest! This listing is a Residential CPR.

948 Kai Hele Ku St Unit Unit A, Lahaina

Listing courtesy of Welcome Hawaii Properties.

$5,999,000
3 Beds ⋅ 2 Baths ⋅ 404090 MLS ⋅ Fee Simple Tenure
Exclusive and rarely available beachfront property on Kihei Maui’s south shore. With breathtaking panoramic views from the south shore of Kihei Maui. Gaze out at dramatic island views of Lanai, Kahoolawe, West Maui and Molokini with your favorite cup of joe or cocktail. This is an incredibly rare opportunity to create your own private sanctuary on this oversized lot of 15,785 square feet perched atop on Halama Street. The shoreline has a peaceful fine soft white sandy beach that is sheltered by off-shore reefs which create a calm lagoon-like safe area to play and swim in the warm shallow water. Close to restaurants, coffee shops, Public Library, outdoor skating rink, tennis courts, baseball field, shops, a multi-use oceanfront and World class golf courses. Don’t miss this rare opportunity to build your dream home on Maui!

1756 Halama St, Kihei

Listing courtesy of Five Star Realty Inc..

$5,950,000
5 Beds ⋅ 4 Baths ⋅ 408014 MLS ⋅ Fee Simple Tenure
A rare South Maui estate — 2.118 acres in the exclusive gated community of Kaimanu Estates. This private retreat feels like living in Hana and Old Hawai‘i, surrounded by hundreds of native and fruiting trees including avocado, citrus, banana, lilikoi, guava and many more. With 4,718 sq. ft. in the main residence and a detached studio ohana, the property offers unmatched privacy and opportunity rarely found in South Maui. Just minutes away are Wailea’s world-class golf courses, resorts, fine dining, boutique shopping, and some of the best beaches in the world. Here you’ll find the perfect balance of tropical seclusion and resort-side convenience.

135 Kaimanu Pl, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$5,850,000
3 Beds ⋅ 3 Baths ⋅ 409059 MLS ⋅ Fee Simple Tenure
This unique Napili oceanfront residence is nestled on a coastal bluff in the center of the bay. It is protected from the risk of erosion. Views are unobstructed of the Pacific and the neighbor islands of Lanai and Molokai, as well as year round sunset views. The exceptional floor plan set over multi levels includes the living area overlooking the saltwater infinity edge pool, three bedrooms, three baths, an outdoor shower, and two-car garage. This special location offers front row seats to watch the surf at Little Makaha, whale watching in season, and turtles all year long. It is also accessible to private tide pools and the surf at Little Makaha. Additionally, the home is equipped with a Tesla battery and 68-panel photovoltaic system, which is grandfathered into the Net Energy Metering Program. The Net Metering agreement is transferable. Beaches, grocery stores, and restaurants are only a few minutes away. Napili is home to Maui Preparatory Academy and a short distance to Kaanapali and Kapalua Resorts.

5171 Lower Honoapiilani Rd, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$5,500,000
2 Beds ⋅ 2 Baths ⋅ 407170 MLS ⋅ Fee Simple Tenure
Outside the box, Inside the box... the choice is yours. Welcome to the QK Haiku, homegrown Maui modernism at its best. Located oceanfront in a diverse and welcoming north shore agricultural neighborhood, the QK offers concise modern living - everything you need, and nothing you don't. Designed in collaboration with Maui Architectural Group, the project combines state of the art energy and water self sufficiency with a minimalist architectural form that gets out of the way of the bold and energetic oceanfront setting. The two rectangular forms use transparency to minimize their boundaries to the natural world, while cleverly concealing water catchment, solar electricity harvesting and battery storage. The 2 bedroom house with its living green roof is tucked into the earth, and the art gallery-like farm office floats above the property tucking itself into the sky. Seclusion can be enjoyed here without loneliness as Hoolawa road has a great community and even its own cafe and gathering space. The land offers the possibility of building another main residence. Entertaining... Contemplation... Growing Food... What will you do when you move in?

454 Hoolawa Rd, Haiku

Listing courtesy of Hawaii Life (W).

$5,500,000
4 Beds ⋅ 3 Baths ⋅ 406427 MLS ⋅ Fee Simple Tenure
Oceanfront home and cottage in a highly desirable private and quiet Kuau neighborhood on Maui’s renowned North Shore. This unique offering is ideally situated in the perfect location, just minutes away from sandy beaches, Kuau Store, Mama’s Fish House, and a quick drive to the lively town of Paia - known for its boutique shopping, local dining options, and vibrant plantation style charm. The main residence is a 4-bedroom, 3-bath home that captures the relaxed island lifestyle with its thoughtfully remodeled interior and breezy, beach-inspired exterior. The first floor features an open-concept layout with wall-to-wall sliding doors providing captivating ocean views as a backdrop with complimentary high ceilings. The expansive sliding doors open up to a wrap-around lanai just off the kitchen and dining area, seamlessly blending indoor and outdoor living while showcasing stunning ocean views and refreshing trade winds. The first floor hosts a guest bedroom, and a full guest bathroom. Upstairs, you will find the primary suite with ensuite, two additional bedrooms, and a second living area with panoramic views spanning from Kahakuloa and Molokai, to Kuau Bay with Ho’okipa just around the corner. Outdoor enthusiasts will appreciate the proximity to world-class water and wind sports such as surfing, kite surfing, wind surfing, diving, paddling, and shelling all just steps away. Adding to the appeal is a charming detached 3-bedroom, 2-bath cottage with classic plantation-style architecture, ready for your personal touch and available to generate potential rental income. This property offering is your opportunity to own in one of Maui’s most coveted locations, where the rhythm of the ocean meets you at the comfort of your home.

116 Kuau Beach Pl, Paia

Listing courtesy of Hawaii Life (W).

$5,495,000
4 Beds ⋅ 4 Baths ⋅ 406329 MLS ⋅ Fee Simple Tenure
Self Sustaining Tropical Estate and Cacao Farm - Potential for Seller Financing - Nestled between two river streams on Maui’s serene east end, this extraordinary 14.9-acre tropical estate and working farm offers a rare chance to embrace an off-the-grid lifestyle in true paradise. Designed for self-sustainability at its finest, this unique gentleman’s and ladies’ farm features a deep water well providing pristine drinking water, a powerful state-of-the-art solar energy system, modern septic systems, and acres of mature, fruit-bearing cacao trees. The land is also rich with juicy tropical fruits and vibrant flowering plants. Currently home to approximately 600 cacao trees, the property has the potential to expand up to 11,500 trees. Additionally, an adjacent 180 acres may be available, supporting up to 180,000 more trees. As global cacao production declines and chocolate prices soar, Hawaii is emerging as a prime location for cacao cultivation—making this a timely and strategic investment. Located just 600 feet from the ocean, the estate is exceptionally private and peaceful, with lush botanical surroundings, sweeping ocean views, and three separate access points. Bordered by streams and wrapped in natural beauty, this tropical sanctuary offers unparalleled tranquility, sustainability, and the luxury of living in harmony with nature.

1600 Lower Nahiku Rd, Hana

Listing courtesy of Coldwell Banker Island Prop(S).

$5,200,000
3 Beds ⋅ 4 Baths ⋅ 409685 MLS ⋅ Fee Simple Tenure
Poised within a prestigious oceanfront community, but positioned without the front row real estate price premium, 10 Hui Road E is a fully updated, multi-level estate that combines dramatic ocean views with a protected location. Just steps back from the shoreline, the property captures elevated Pacific views and year-round sunsets. The residence has undergone a comprehensive renovation featuring high-end fixtures and finishes throughout. The main level centers on an open-concept kitchen equipped with custom cabinetry, countertops, and premium integrated appliances. Stone flooring runs through the living spaces, where large glass sliders open to a spacious covered lanai, a flat green lawn, and newly cleared landscape corridors designed to maximize the ocean view. Truly an indoor-outdoor lifestyle dream. The 3,175-square-foot floor plan provides excellent separation of space. The main floor hosts two private guest en-suites. The entire second level is dedicated to the primary suite, which includes a gracious ocean view deck, a custom walk-in closet, and a stone-finished bathroom with a soaking tub and dual vanities. The home is situated just south of the luxury Kapalua Resort, providing quick access to world-class golf courses, fine dining, shopping, tennis, and pickleball. It is offered exquisitely furnished, ready to move right in to your Maui Beach Home.

10 Hui Rd E Rd, Lahaina

Listing courtesy of Coldwell Banker Island Prop(S).

$5,200,000
5 Beds ⋅ 5 Baths ⋅ 407666 MLS ⋅ Fee Simple Tenure
Nestled on 3.02 acres in the gated Puunoa community, 257 Hokiokio Place overlooks Lahaina from its gently sloping hillside setting, offering sweeping ocean and sunset views from nearly every room. Built in 2024 and now nearing completion by its owner-builder, this single-level estate blends modern design with comfortable, open-concept living. Spanning over 3,500 square feet, the home features 5 bedrooms and 4.5 baths, providing generous space for family and guests. The thoughtful floor plan captures both indoor and outdoor living, perfectly positioned to take advantage of Maui’s year-round sunshine and trade winds. While the finishing touches and landscaping are still in progress, the groundwork for a remarkable estate has been laid. Many fruit trees have already been planted, and grading is underway for future horse stables, an ideal setup for equestrian enthusiasts seeking proximity to nearby riding trails. An infinity-edge pool has been fully designed and permitted, allowing the next owner to complete this final element to their own taste. Easy bypass access ensures convenient travel around Maui and quick connection to the rebirth of historic Lahaina town below. This is an exceptional opportunity to own a newly built residence in one of West Maui’s most sought-after locations, offering expansive space, unmatched views, and a chance to put your own finishing touches on a true Lahaina legacy property. This is a residential CPR. The 3.02 acre property is lot "A". The six acre lot "C", makai of lot "A", may also be available for purchase.

257 Hokiokio Pl Unit A, Lahaina

Listing courtesy of eXp Realty.

$5,199,000
4 Beds ⋅ 5 Baths ⋅ 406460 MLS ⋅ Fee Simple Tenure
Contemporary aesthetics define this gorgeous new home in Ka'anapali's Lanikeha community. This elegant new 4-bedroom, 5-bathroom home boasts 3,691 sq. ft. of living space, 956 sq. ft of covered lanai space, a 104 sq. ft. covered entry, and 1,298 sq. ft. of double-garage space: that's two separate, two-car garages - a rare and highly desirable feature for added flexibility and storage! The finishes in this new construction are luxury-class, featuring elegant tile and stone throughout, custom wood cabinetry, refined bathroom fixtures, and best-in-class kitchen appliances. From the entry, the home draws you into the Great Room and out to stunning ocean and outer-island views, which are protected by the community’s CCR roof-height restrictions. The Great Room and kitchen open onto the covered lanai; this functional and beautiful space lends itself to classic indoor-outdoor Hawaiian resort-style living. Outside, the lanai provides ample shaded space for dining, with an infinity-edge pool and jetted spa just beyond. The design allows bathers and those relaxing outside to take in the stunning ocean views from every angle. A built-in barbecue area complements the lanai amenities, making it ideal for entertaining and everyday living. The home features two wings that flank the Great Room, each housing bedrooms and amenities. On the left side is the Primary Suite wing, complete with an ocean-facing, private, covered lanai and a spacious bathroom; a second guest room is also located in the Primary wing. The right wing is home to two additional guest rooms; an ocean-facing bedroom also boasts a private covered lanai. The lucky owners of this new home will enjoy stunning views of the outer islands of Lanai and Molokai, as well as arguably the best sunsets on Maui year-round. During the winter, you will be treated to the magical sight of Hawaii's famous humpbacks breaching in the blue Pacific. While you will enjoy living inside a gated community, you are also just minutes from some of Maui's best beaches, restaurants, and shopping in the Ka'anapali Beach resort area. Be the first to live in this Maui dream designer property that's been three years in the making!

44 Loli'i Pl, Lahaina

Listing courtesy of Welcome Hawaii Properties.

$5,195,000
3 Beds ⋅ 4 Baths ⋅ 408268 MLS ⋅ Fee Simple Tenure
Set against the dramatic backdrop of the Pacific, 1008 Sunset Place offers a rare opportunity to own a refined island residence in the heart of Kapalua. Perfectly positioned to capture glowing sunsets, gentle trade winds, and sweeping ocean views, this Kapalua home is thoughtfully designed for seamless indoor–outdoor living. Open, light-filled interiors flow effortlessly to expansive lanais, creating ideal spaces for entertaining, dining al fresco, or simply unwinding while enjoying seasonal whale watching during the winter months. Thoughtful architectural lines, quality finishes, and casually elegant furnishings contribute to a timeless island aesthetic. The well-appointed kitchen features premium Sub-Zero and Dacor appliances, enhancing both form and function. Located within the gated community of Pineapple Hill, one of Kapalua Resort’s most sought-after residential enclaves, residents enjoy access to a community swimming pool, tennis and pickleball courts, and on-site resident management. Pineapple Hill offers close proximity to Kapalua’s world-class amenities, including championship golf courses, award-winning beaches, scenic coastal trails, tennis facilities, and fine dining—while maintaining a sense of privacy and tranquility. This is West Maui living at its finest, defined by ocean views, spectacular sunsets, and the enduring appeal of the Kapalua lifestyle.

1008 Sunset Pl, Lahaina

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

$5,165,000
4 Beds ⋅ 4 Baths ⋅ 407481 MLS ⋅ Fee Simple Tenure
Upon entering this magnificent 3,315 sq. ft. home you will be mesmerized by its spectacular panoramic due west views of the Pacific Ocean between Lana'i and Moloka'i offering colorful year-round sunsets. A remodeled masterpiece featuring vaulted cedar ceilings, Italian marble and eucalyptus wood floors, quartz countertops and sapele cabinets, just to name a few of the recent refinements of this tastefully furnished home. This most popular floorplan offers all 4 bedrooms, 3 1/2 bathrooms, living room, kitchen, outdoor living are and pool on the main level. The added bonus of an upstairs loft offers many use options, currently set up as an office/sitting area to enjoy the ocean views from the high dormer windows. A beautiful infinity edge pool with Baja steps and spa was just completed, with the entire house and pool equipment are supported by 52 solar panels and 2 Tesla batteries. This home is perched on a quiet cul-de-sac at the crest of Pineapple Hill, a highly desirable gated subdivision which offers residents a very large community/lap pool, tennis & pickleball courts, a pavilion / entertainment area, catering kitchen and barbecues. Pineapple Hill itself is located inside the 1,650-acre resort area of Kapalua's famed 23,000-acre plantation. Kapalua offers more than 100 miles of hiking trails, duck pond, bike trails, tennis center, two world famous golf courses, two five-star hotels plus five-star Montage Spa and numerous fine dining restaurants, all accessible via complimentary resort-wide shuttles. 104 Woodrose Place is a must-see home in impeccable condition, it looks and shows as if it were built yesterday.

104 Woodrose Pl, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$5,000,000
4 Beds ⋅ 4 Baths ⋅ 409679 MLS ⋅ Fee Simple Tenure
Welcome to the Resort in Maui Meadows — an extraordinary private estate where jaw-dropping panoramic ocean views, unforgettable sunsets, and elevated island living converge in one of South Maui’s most coveted neighborhoods. Perfectly positioned above the coastline, this exceptional residence captures sweeping vistas stretching across the Pacific Ocean to the neighboring islands, creating a breathtaking backdrop from nearly every room. By day, enjoy sparkling turquoise waters and endless horizon views; by evening, experience Maui’s legendary sunsets illuminating the sky in spectacular color. Designed to live like a private luxury resort, the property is an entertainer’s dream. Expansive indoor-outdoor living spaces flow seamlessly onto oversized lanais and gathering areas curated for unforgettable sunset dinners, cocktail parties, celebrations, and relaxed evenings beneath the stars. The open-concept design invites effortless hosting while maximizing the stunning ocean vistas and cooling island trade winds throughout the home. The chef’s kitchen anchors the residence with premium appliances, generous prep and serving areas, and elegant finishes designed for both intimate dining and large-scale entertaining. Spacious guest accommodations provide comfort and privacy for family and friends, while the primary suite offers a tranquil retreat with spa-inspired luxury and mesmerizing ocean views. Surrounded by lush tropical landscaping and an atmosphere of complete serenity, the Resort in Maui Meadows delivers a rare sense of escape while remaining just moments from Wailea’s world-class beaches, golf courses, fine dining, and luxury resorts. This is more than a home — it is a destination, a retreat, and a lifestyle defined by breathtaking beauty, privacy, and unforgettable entertaining in the heart of South Maui.

557 Kupulau Dr, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

$4,999,999
2 Beds ⋅ 3 Baths ⋅ 409543 MLS ⋅ Fee Simple Tenure
Discreetly positioned off Kula Highway, the approach reveals very little. A winding drive. A narrowing road. Then, through the trees, a freshly painted 1933 guest cottage quietly appears, a subtle introduction to what lies ahead. A whisper of what came before. Keep driving. The landscape begins to unfold. And then you arrive. A refined modern architectural private retreat. Exposed beams. Oak floors. Walls of Andersen windows drawing the landscape inward from every direction. Once cattle ranch land, these twenty-two rolling acres of open pasture and mature eucalyptus and jacaranda have evolved into one of Maui’s most distinctive private estates. Deer move effortlessly through the golden afternoon light. Birdsong replaces background noise. The silence here feels restorative, the kind that settles into you. The former owner named it Pheasant Ridge for good reason. Originally built in 2001 and thoughtfully reimagined in 2019, the main home was designed for a deeply intentional way of living. The open-concept kitchen, dining, and living spaces flow together in one expansive, light-filled room anchored by a fireplace and framed entirely by the land beyond. The primary suite faces Haleakala. The guest suite offers its own en-suite bath and soaking tub worthy of a primary retreat. This is not beach Maui. The air is cooler. The light lingers longer. Life moves at its own pace. Evenings call for the warmth of a fireplace, and there will be evenings worthy of it. A Pilates studio occupies the garage. A separate she - shed is settled into the surrounding landscape. AG zoning and open pasture invite horses, livestock, or simply the freedom of open land returning to its natural purpose.

8515 Kula Hwy, Kula

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

$4,999,000
2 Beds ⋅ 1 Baths ⋅ 408461 MLS ⋅ Fee Simple Tenure
Also listed as Commercial-For sale - MLS# 408462. Best Mixed Use, Turnkey business/residential complex, Landmark & Iconic Maui, HI property. $26K/mo. existing & diversified residential & commercial rental income with 5,000sf commercial space and 1800sf residential space currently leased with 100% occupancy. Multiple very profitable business opportunities grossing over $1.2mil/yr. Additional rental and business income being added. This property is way less than free!! Subdividable and CPRable. Exceptional, 360 deg views in perfect weather, very affluent Lower Kula area of $2-15mil homes. This growing area needs more business development with a huge upside potential in the near future. Destined to be a possible $40mil project-mixed use condos, medical plaza, hotel/restaurant, or Kula Town Center. Purchase now at a high cap rate and realize your future income ambitions with this unique offering in Paradise. Almost an acre, all utilities, 2 water meters, level and all useable. Over $150K in repairs/upgrades recently. Owner or SBA financing with best terms available. 1031 Exchange, Sale Leaseback, or Lease Option possible. More info/pics at Loopnet.com and Bizbuysell.com. Do Not Disturb businesses/tenants. Shown by appt only. Beware!! Vicious guard dog on site 24/7. You will not find a better, more lucrative deal Anywhere!

3135 Lower Kula Rd, Kula

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

$4,995,000
3 Beds ⋅ 2 Baths ⋅ 410634 MLS ⋅ Fee Simple Tenure
OCEANFRONT LIVING, NORTH SHORE STYLE. Some oceanfront homes give you a view. This one makes the ocean part of everyday life. Set beside Tavares Bay, just minutes east of Paia, 465 & 467 Hana Hwy combine an oceanfront main residence, private guest cottage and additional approx. 6,000 SF adjacent parcel into one exceptional North Shore retreat. From the moment you enter, the Pacific draws you through the home, filling the living and dining spaces with blue water, horizon and light. The Pacific is the backdrop, the surf is the soundtrack, and the home creates an effortless connection between indoor and outdoor living. Treasured as the owner’s retreat for over twenty years, the light-filled, furnished, single-level main residence offers 2,072 sq. ft. with 3 bedrooms and 2 baths. Imagine waking to the sea and ending the day to the gentle lull of the waves. Vaulted natural wood ceilings, crisp white enameled beams and travertine floors create a warm, natural palette throughout the home, complemented by granite counters, soft-close cabinetry, stainless-steel appliances and central A/C. Renovated in approximately 2005 and updated in 2018, expansive windows keep the ocean ever present throughout the home. The ocean-facing primary suite opens to a private outdoor seating area. Its spacious en-suite bath features a walk-in closet, floor-to-ceiling stone-tiled open shower, private outdoor shower and soaking tub. Outside, the grounds have been artfully nurtured over time. Mature tropical landscaping, including ginger, heliconia, plumeria and abundant foliage, creates privacy and the feeling of an established Hawaiian garden. Panoramic Pacific, West Maui Mountain, Molokai and Sunset Color views surround the property. Here, the ocean becomes part of the rhythm of the day. Look toward Tavares Bay to see what the swell is bringing, head down to the beach, or simply stay home and watch the ocean change throughout the day. A separate guest cottage, thoughtfully divided into two independent studio accommodations, adds another dimension to the property. Studio One features a wet bar and full bathroom, while Studio Two includes a full kitchen and full bathroom. The cottage creates inviting possibilities for guests or extended family while maintaining comfortable separation from the main residence. Together, the two parcels total 19,079 sq. ft., nearly half an acre adjacent to Tavares Bay. The included adjacent vacant parcel has its own water meter and expands the possibilities of the property, offering additional space to shape it around your own vision for the future. Two parcels. A private guest cottage. Nearly half an acre beside Tavares Bay. Thoughtfully established tropical grounds. And at the heart of it all, a home where the Pacific is part of how you live.

465 & 467 Hana Hwy, Paia

Listing courtesy of Maui Real Estate Advisors LLC.

$4,995,000
5 Beds ⋅ 4 Baths ⋅ 409257 MLS ⋅ Fee Simple Tenure
Welcome to perfection in Upcountry Kula. Imagine a private retreat spanning 2.367 acres, surrounded by the abundant natural beauty of the land, combined with pristine bi-coastal ocean views reaching to Moloka’i and Lana’i. A legacy estate of this caliber defines tranquil upcountry living at its best, creating a home to celebrate life’s landmarks. Resting at 2,200 feet on Haleakala’s western slope, this unique residence enjoys the best of the mild upcountry climate. Kula residents appreciate year-round Springtime with gentle Pacific breezes and consistently comfortable temperatures. Panoramic views of the Pacific greet you throughout the home’s interiors. Oversized picture windows in the living room and primary suite frame these reach-out-and-touch unequaled vistas, changing throughout the day as the light does. The main residence’s light-filled, lofty spaces seamlessly meld together with 5 bedrooms and 3.5 baths, spanning 3,644 square feet. The home's custom Mediterranean architecture and local craftsmanship embrace simplicity, which defines the unique upcountry lifestyle. In addition to those ocean views, there are forty native fruit trees (avocado, mango, citrus, mangosteen, star apple, lychee, peach, nectarine, star fruit), honoring the land and the year-round outdoor living experience. A separate suite with a private entrance is the perfect flex space for a creative studio, work-from-home office, full-size gym with infrared sauna, second kitchen, full bathroom, private deck, and yard. The main residence has brand-new Wolf appliances, including an induction range, refrigerator, and dishwasher. Custom new white oak hardwood flooring throughout is the canvas for your personal design statement. Discover the custom yurt with 20ft ceilings, including ocean and unequaled Haleakala’s views. Walking trails wind throughout the property's landscape, with ocean views at every turn, and are a natural amenity to this perfect retreat. The redesigned pool and spa are the home’s centerpiece, boasting a 40-foot saltwater pool with solar heating. Imagine experiencing the best of Kula from sunrise to sunset, 365 days a year. Visit this Upcountry Kula home, and you will discover it is exactly where you are meant to be.

1260 Naalae Rd, Kula

Listing courtesy of Compass-W.

$4,995,000
4 Beds ⋅ 5 Baths ⋅ 404626 MLS ⋅ Fee Simple Tenure
Elevated design meets serene island living in this architectural triumph within the esteemed double-gated Lanikeha community in the Ka'anapali Golf Estates. This 4-bedroom, 5-bathroom residence spans 3,710 square feet of interior space, offering a harmonious blend of contemporary luxury and timeless Hawaiian elegance. From the moment you enter, you'll be captivated by the expansive, light-filled layout. High ceilings and wide-plank white oak flooring create a seamless flow throughout the home. The gourmet kitchen boasts a Miele refrigerator, a Wolf range, dual dishwashers, and a thoughtfully designed pass-through window connecting to the outdoor kitchen and BBQ—a feature crafted for effortless entertaining. Nearly 1,000 square feet of covered lanai beckons you to savor meals and tranquil moments while soaking in panoramic ocean and outer-island views. Just beyond, the stunning in-ground pool boasts a Baja shelf and an oversized hot tub—a true retreat designed for relaxation and indulgence. Practicality meets luxury with features such as a three-car garage, two-zone central air conditioning, and Hana Hou Builders' signature attention to detail. Each element of the home has been meticulously curated to enhance your elegant living experience, including the landscaped grounds that complement the home's modern aesthetic. You are within 5 minutes of Kaanapali Beach and Whalers Village shops. You are also a stone's throw away from the Ka'anapali Golf Courses, while the PGA Plantation Course in Kapalua is just a 15-minute drive. Lanikeha owners also enjoy access to a fabulous community clubhouse with a fitness center, billiards, and a beautiful infinity-edge pool. This move-in ready, new luxury residence exemplifies elegant contemporary island design. Its flawless design, functionality, and perfect location make it an extraordinary opportunity to open the door to the ultimate Ka'anapali resort-style living.

837 Anapuni Loop, Lahaina

Listing courtesy of Welcome Hawaii Properties.

$4,975,000
4 Beds ⋅ 5 Baths ⋅ 409156 MLS ⋅ Fee Simple Tenure
Located within the prestigious gated enclave of Pineapple Hill in the world-renowned Kapalua resort, 620 Silversword Drive represents a rare offering in one of Maui’s most exclusive communities. This impeccably maintained 4-bedroom, 4.5-bath residence has been substantially remodeled and is in flawless, move-in-ready condition, including a new roof with photovoltaic and Tesla battery. Perfectly positioned to capture unobstructed panoramic vistas, the home showcases breathtaking sunset views that stretch across the Pacific, widely considered among the finest in Kapalua. The seamless indoor-outdoor living experience is designed to embrace Maui’s natural beauty, with large backyard ideal for entertaining or quiet relaxation. Residents enjoy privileged access to Kapalua’s top-notch amenities, including championship golf course, full-service spa, tennis and pickleball facilities, and a collection of exceptional dining experiences. Pineapple Hill is known for its privacy, elegance, and elevated lifestyle, making it one of Maui’s most sought-after luxury communities. This is a rare opportunity to own a turnkey home in a premier location, where refined island living meets unmatched views and world-class resort amenities

620 Silversword Dr Unit 26, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

$4,950,000
3 Beds ⋅ 3 Baths ⋅ 410375 MLS ⋅ Fee Simple Tenure
Perched within the prestigious double-gated enclave of Lanikeha in the Ka‘anapali Golf Estates, this exceptional fully furnished single-level residence was thoughtfully designed to showcase one of West Maui’s most captivating panoramas. Framed by breathtaking views of the Pacific Ocean, the neighboring islands of Lana'i and Moloka'i, and spectacular sunsets throughout the year, the home offers an effortless blend of timeless craftsmanship, modern technology, and the relaxed elegance that defines luxury island living. From the moment you enter, soaring vaulted Tigerwood ceilings, exquisite Sapele wood trim, and impressive 8-foot solid Mahogany doors create an immediate sense of warmth, scale, and refinement. Every finish has been carefully selected, resulting in a residence that feels both sophisticated and inviting. An integrated whole-home audio system provides the perfect soundtrack whether enjoying a quiet evening or entertaining family and friends. Designed for those who appreciate both beauty and functionality, the gourmet kitchen features premium Bosch appliances, a Liebherr refrigerator and freezer, and an open-concept layout that keeps the spectacular ocean views front and center. Whether preparing a casual breakfast or hosting sunset dinners, the surrounding scenery becomes part of every experience. The primary suite serves as a private sanctuary, offering a spa-inspired bath complete with both indoor and outdoor showers. The outdoor shower is a true work of art, highlighted by an extraordinary solid granite slab that transforms a daily routine into a uniquely luxurious experience. Modern convenience is seamlessly integrated throughout the home with Legrand smart lighting and fan controls, voice-activated motorized lanai screens, multi-zone air conditioning, and advanced home automation. Sustainability is equally impressive, with 33 owned photovoltaic solar panels paired with three Tesla Powerwalls, providing exceptional energy efficiency and peace of mind without sacrificing comfort. Beyond the residence itself, Lani?keha offers one of Maui’s most desirable lifestyles. Situated behind two private gated entrances within a golf cart-friendly community, owners enjoy the convenience of leaving the car behind for many of life’s daily pleasures. A short golf cart ride leads to world-renowned Ka‘anapali Beach, Whalers Village, championship golf, oceanfront dining, upscale shopping, tennis and pickleball facilities, luxury resorts, and countless recreational activities. West-facing and perfectly positioned between the islands of Lana'i and Moloka'i, the home captures mesmerizing sunsets nearly every evening, while seasonal whale watching becomes part of everyday life during the winter months. Combined with West Maui’s remarkably temperate climate—widely regarded as one of the finest anywhere in the world—this extraordinary property offers an unparalleled opportunity to experience the very best of island living.

24 Lolii Pl, Lahaina

Listing courtesy of Berkshire Hathaway Maui Prop-L.

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