10 most expensive homes for sale in Maui Meadows
In Maui Meadows the median sale price for homes on the market is about -, however, high-end properties can be listed at a much higher price point. Here are the top ten most expensive homes for sale in Maui Meadows (Maui).
Home
5
bd
4
ba
4,718
sqft
$6,999,000
5
bd 4
ba 4,718
sqft
bd 4
ba 4,718
sqft
Home for sale
135 Kaimanu Pl Kihei, Maui
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.
Home
4
bd
4
ba
3,447
sqft
$5,000,000
4
bd 4
ba 3,447
sqft
bd 4
ba 3,447
sqft
Home for sale
557 Kupulau Dr Kihei, Maui Neighborhood: Kihei
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.
Home
5
bd
4
ba
3,254
sqft
$4,500,000 ▼ $40,500,000
5
bd 4
ba 3,254
sqft
bd 4
ba 3,254
sqft
Home for sale
3264 Keha Dr Kihei, Maui Neighborhood: Maui Meadows
E Komo Mai to Your Own Private Paradise Above Wailea As you pass through the gates at 3264 Keha Drive, a lush tropical landscape unfolds before you. Spread across nearly three-quarters of an acre in the heart of Maui Meadows, this private sanctuary welcomes you home. Every detail of this incredible multi-family estate has been designed to embrace the beauty and peacefulness of island living, while delivering the comforts and amenities of a private luxury retreat. Cascading waterfalls and a tranquil koi pond greet you upon arrival, and from the very first moment, the stage is set for an immersive Maui experience. Perched high above Wailea on the sun-warmed slopes of Haleakala, this estate commands a 180-degree panoramic view that stops you in your tracks every single time. The Pacific stretches endlessly before you, with Kaho'olawe rising from the sea to the left and Lana'i to the right, two islands framing a horizon that transforms at golden hour into something that simply cannot be described, only witnessed. This is the view that Maui is famous for, and it belongs to this home. Life here is lived looking outward from every vantage point the estate offers. Mornings begin slowly, coffee in hand, the ocean laid out below you. Evenings end with the sun dropping toward the horizon as the sky ignites in brilliant color, the trade winds moving through, each sunset an original. You will never see the same one twice. The estate is rare in both scale and versatility, offering significant square footage and a multi-structure configuration that opens up genuine possibilities. The main residence, complete with two living rooms and generous proportions, is complemented by an attached private guest suite, a separate two-bedroom rental, and an additional private guest suite. For a multi-generational family, it is the perfect gathering place. For the investor, it is an income-producing property with the rental infrastructure already in place. Outside, resort-caliber living awaits. A sparkling pool anchors the outdoor space, with a sauna, steam room, full outdoor bar, and poolside television all within reach, thoughtfully designed for quiet mornings and unforgettable gatherings alike. These spaces don't just complement the Maui lifestyle; they embody it. Over 72 solar panels paired with integrated smart home technology run quietly in the background, dramatically reducing energy costs and delivering the kind of efficiency a property of this caliber deserves. A fully electric Nissan Leaf and dedicated charging station are included, making the transition to island living as seamless as it should be. This estate is offered fully furnished and completely turnkey, perfectly suited for the island family ready to settle into something exceptional, the buyer watching another winter roll in somewhere far from here, or the investor seeking a property that works as beautifully as it looks. Bring your suitcase. Everything else is already waiting. Opportunities like this are rare. The elevation, the views, the scale, the versatility, all within one of Maui's most coveted neighborhoods. This kind of property doesn't come around often, and when it does, it doesn't last. Resort Living. Island Privacy. Endless Possibilities.
Home
4
bd
4
ba
3,399
sqft
$3,200,000 ▼ $300,000
4
bd 4
ba 3,399
sqft
bd 4
ba 3,399
sqft
Home for sale
744 Lanina Pl Kihei, Maui Neighborhood: Maui Meadows
Eclectic, exotic, bursting with energy this Maui Meadows home is such a special spot on the island with its breathtaking ocean views, deep tropical setting and exquisite finishes throughout. You will be Awestruck with the incredible design and finishes throughout this entire property with the beautiful pool, ideally situated for entertaining, lavish master suite and incredible chef’s kitchen. Every detail in this beautiful Polynesian style home has been perfectly appointed with a flexible three bedroom floor plan and Detached cottage that provides a great property and amenities for your perfect Maui dream home
Home
3
bd
3
ba
3,028
sqft
$2,549,000 ▼ $146,000
3
bd 3
ba 3,028
sqft
bd 3
ba 3,028
sqft
Home for sale
3291 Waileia Pl Kihei, Maui Neighborhood: Maui Meadows
Luxury Spanish Villa in Wailea, Maui. Nestled in one of Wailea’s most sought-after neighborhoods, this meticulously upgraded contemporary Spanish villa blends timeless elegance with modern comfort. Situated on over half an acre of prime real estate and boasting over 5,000 square feet of living space under roof, this estate epitomizes luxury island living with single level living, having only the third bedroom upstairs. Recently reimagined, the home has undergone extensive renovations to seamlessly combine classic Spanish architectural elements such as 2' x 4' porcelain tiles and custom Moroccan pendant in kitchen with modern-day amenities.The iconic Spanish tile roof enhances the property’s curb appeal, while the grand entry and courtyard create a stately ambiance, welcoming you to your private sanctuary. Every detail has been thoughtfully upgraded in recent years, from high-end finishes such as European Oak wood floors, Hoppe windows and doors, Thermador appliances, to state-of-the-art systems such as Mitsubishi Air Conditioning and Luxe garage doors, ensuring a home that is both stylish and functional. The expansive outdoor living spaces include a large swimming pool, an inviting pool deck, and a covered lanai—perfect for entertaining or enjoying Maui’s year-round tropical climate. The property’s elevated position at the end of a quiet cul-de-sac provides unparalleled privacy and seclusion, free from through traffic. Inside, new air conditioning systems, premium finishes, and refined touches elevate the living experience. The oversized upper deck is a true showstopper, offering breathtaking ocean views, daily sunsets over the outer islands, and seasonal whale-watching opportunities. This estate is move-in ready and waiting to welcome its next discerning homeowner to indulge in tranquility, beauty, and exclusivity with proximity to Wailea and Makena's best beaches and resorts.
Home
4
bd
4
ba
2,804
sqft
$2,500,000
4
bd 4
ba 2,804
sqft
bd 4
ba 2,804
sqft
Exceptional 3Bed/3Bath with 1B/1.5B Detached Ohana in front, BOTH with Expansive Ocean views and wrap around decks. House has two wrap around decks with Ocean views from living areas, kitchen, and bedrooms. Vaulted ceilings with open floor plan. 1Bedroom Ohana has covered carport, large deck also with Ocean views from living area and deck. Buildings were painted and tented this year. Driveway was graded and new gravel just put in in May 2026. Fruit producing Manago tree in fenced back yard with BBQ and storage shed.
$2.5m
3124 Nahenahe Pl, Kihei
Home
3
bd
2
ba
2,834
sqft
$2,500,000
3
bd 2
ba 2,834
sqft
bd 2
ba 2,834
sqft
Home for sale
3124 Nahenahe Pl Kihei, Maui
Discover one of Maui Meadows' hidden gems at the end of a quiet, private cul-de-sac. This beautifully updated home feels like a modern treehouse, surrounded by stunning ocean, mountain, and sunset views with no wires enjoyed from multiple lanai spaces. The main level features bright, open living, a contemporary kitchen, and a gorgeous primary suite with a soaking tub overlooking the ocean. Downstairs offers a large family room, two spacious bedrooms, abundant storage, and walk-out access to the pool, hot tub, and entertaining deck. With tropical landscaping, low-maintenance materials throughout, and an adjacent lot optionally available to the buyer, this is a rare Maui Meadows retreat offering privacy, views, and flexible living in one of South Maui's most desired neighborhoods.
Home
4
bd
4
ba
3,296
sqft
$2,500,000
4
bd 4
ba 3,296
sqft
bd 4
ba 3,296
sqft
Home for sale
487 Hoala Dr Kihei, Maui Neighborhood: Maui Meadows
A true family home offering expansive living space and room to breathe. This beautifully renovated property features tasteful finishes throughout, a large wraparound deck with great ocean and mountain views, a spacious three-car carport, and a dedicated workshop. The main home includes an extended living area that's ideal for multigenerational living generous in size and conveniently located on the main level for easy access. In addition, there's a charming two-bedroom cottage with its own carport, plus a stunning resort-style pool perfectly tucked away for maximum privacy. This property is all about seclusion and comfort an exceptional Maui retreat. Not a drive-by, as it's impossible to appreciate all the features from the street. Enjoy your own backyard oasis with mature mango, papaya, and pomelo trees providing a fresh tropical harvest.
Home
3
bd
3
ba
2,055
sqft
$2,499,000
3
bd 3
ba 2,055
sqft
bd 3
ba 2,055
sqft
Home for sale
3450 Malina Pl Kihei, Maui Neighborhood: Maui Meadows
Enjoy incredible ocean views from this beautifully updated home and cottage located in the highly sought-after Maui Meadows neighborhood. Tucked away on a quiet cul-de-sac, this .59-acre property offers exceptional privacy surrounded by lush tropical landscaping, while the spacious pool and deck area create the perfect setting for relaxing or entertaining in true island style. The main residence has been recently remodeled and features high ceilings, a stunning chef's kitchen designed for both everyday living and hosting, as well as a loft that can be used as an office or private retreat. This custom pole house offers 3 bedrooms and 3 bathrooms with lanai spaces that seamlessly blend indoor and outdoor living. A separate 1-bedroom, 1-bath cottage provides excellent flexibility for guests or extended family. One of the unique highlights of this property is the unobstructed ocean views with no power lines in sight, enhancing the natural beauty of the setting. This is a truly special island home you won'tt want to miss. The location is unbeatable—peaceful and private, yet just minutes from the world-famous beaches, resorts, restaurants, shopping and golf courses. Your own tropical paradise awaits. Main residence is being sold furnished; the ?ohana is unfurnished
10
3300 Keha Dr
$2.4m ▼ $400,000
3300 Keha Dr, Kihei
Home
3
bd
3
ba
2,484
sqft
$2,400,000 ▼ $400,000
3
bd 3
ba 2,484
sqft
bd 3
ba 2,484
sqft
Home for sale
3300 Keha Dr Kihei, Maui
Amazing ocean and West Maui Mountain views from this three bedroom, three bath pole house in Maui Meadows on a flag lot. Enjoy the pool and spa together with the spectacular views.
* information deemed reliable, but not guaranteed
$2.5m
3124 Nahenahe Pl, Kihei
Home
3
bd
2
ba
2,834
sqft
$2,500,000
3
bd 2
ba 2,834
sqft
bd 2
ba 2,834
sqft
Home for sale
3124 Nahenahe Pl Kihei, Maui
Discover one of Maui Meadows' hidden gems at the end of a quiet, private cul-de-sac. This beautifully updated home feels like a modern treehouse, surrounded by stunning ocean, mountain, and sunset views with no wires enjoyed from multiple lanai spaces. The main level features bright, open living, a contemporary kitchen, and a gorgeous primary suite with a soaking tub overlooking the ocean. Downstairs offers a large family room, two spacious bedrooms, abundant storage, and walk-out access to the pool, hot tub, and entertaining deck. With tropical landscaping, low-maintenance materials throughout, and an adjacent lot optionally available to the buyer, this is a rare Maui Meadows retreat offering privacy, views, and flexible living in one of South Maui's most desired neighborhoods.
Home
5
bd
4
ba
3,254
sqft
$4,500,000 ▼ $40,500,000
5
bd 4
ba 3,254
sqft
bd 4
ba 3,254
sqft
Home for sale
3264 Keha Dr Kihei, Maui Neighborhood: Maui Meadows
E Komo Mai to Your Own Private Paradise Above Wailea As you pass through the gates at 3264 Keha Drive, a lush tropical landscape unfolds before you. Spread across nearly three-quarters of an acre in the heart of Maui Meadows, this private sanctuary welcomes you home. Every detail of this incredible multi-family estate has been designed to embrace the beauty and peacefulness of island living, while delivering the comforts and amenities of a private luxury retreat. Cascading waterfalls and a tranquil koi pond greet you upon arrival, and from the very first moment, the stage is set for an immersive Maui experience. Perched high above Wailea on the sun-warmed slopes of Haleakala, this estate commands a 180-degree panoramic view that stops you in your tracks every single time. The Pacific stretches endlessly before you, with Kaho'olawe rising from the sea to the left and Lana'i to the right, two islands framing a horizon that transforms at golden hour into something that simply cannot be described, only witnessed. This is the view that Maui is famous for, and it belongs to this home. Life here is lived looking outward from every vantage point the estate offers. Mornings begin slowly, coffee in hand, the ocean laid out below you. Evenings end with the sun dropping toward the horizon as the sky ignites in brilliant color, the trade winds moving through, each sunset an original. You will never see the same one twice. The estate is rare in both scale and versatility, offering significant square footage and a multi-structure configuration that opens up genuine possibilities. The main residence, complete with two living rooms and generous proportions, is complemented by an attached private guest suite, a separate two-bedroom rental, and an additional private guest suite. For a multi-generational family, it is the perfect gathering place. For the investor, it is an income-producing property with the rental infrastructure already in place. Outside, resort-caliber living awaits. A sparkling pool anchors the outdoor space, with a sauna, steam room, full outdoor bar, and poolside television all within reach, thoughtfully designed for quiet mornings and unforgettable gatherings alike. These spaces don't just complement the Maui lifestyle; they embody it. Over 72 solar panels paired with integrated smart home technology run quietly in the background, dramatically reducing energy costs and delivering the kind of efficiency a property of this caliber deserves. A fully electric Nissan Leaf and dedicated charging station are included, making the transition to island living as seamless as it should be. This estate is offered fully furnished and completely turnkey, perfectly suited for the island family ready to settle into something exceptional, the buyer watching another winter roll in somewhere far from here, or the investor seeking a property that works as beautifully as it looks. Bring your suitcase. Everything else is already waiting. Opportunities like this are rare. The elevation, the views, the scale, the versatility, all within one of Maui's most coveted neighborhoods. This kind of property doesn't come around often, and when it does, it doesn't last. Resort Living. Island Privacy. Endless Possibilities.
Home
4
bd
4
ba
3,447
sqft
$5,000,000
4
bd 4
ba 3,447
sqft
bd 4
ba 3,447
sqft
Home for sale
557 Kupulau Dr Kihei, Maui Neighborhood: Kihei
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.
Home
2
bd
2
ba
1,014
sqft
$2,199,000
2
bd 2
ba 1,014
sqft
bd 2
ba 1,014
sqft
Home for sale
3161 Mapu Pl Kihei, Maui Neighborhood: Maui Meadows
Welcome to your private tropical oasis in serene Maui Meadows. This remarkable and rare property spans over a 0.52-acre corner lot, offering a true resort-style experience with lush tropical landscaping that provides exceptional privacy and tranquility. This unique estate features three distinct dwellings, making it ideal for multi-generational living, rental income opportunities, or a private family compound. Situated on a corner lot, two of the dwellings are accessed through their own automatic gated entry off Mililani Place. The main residence enjoys a separate private gated entrance off Mapu Place, where the owner has enhanced the property with poured concrete and covered gazebo parking areas. The property offers abundant storage, including a standalone tool shed, additional storage space for seasonal items, and a workshop area—perfect for a DIY enthusiast. The main home features an open and airy floor plan with 2 spacious bedrooms, 2 bathrooms, and an office area. The primary suite includes a beautifully renovated outdoor shower, walk-in closet, ensuite bath, and additional storage space. High vaulted ceilings and an updated kitchen enhance the living space, which opens to a private, fenced backyard complete with a vegetable garden and irrigation system. Split A/C systems have been installed throughout for energy efficiency and customizable cooling. A large south-facing lanai overlooks the tropical grounds and pool, seamlessly extending the living space beyond the interior square footage. The charming 496 sq ft cottage is tucked among the lush gardens and offers 1 bedroom and 1 bathroom with high ceilings and a spacious lanai for indoor-outdoor living. The cottage has been tastefully updated with granite finishes, new tile, and high-end vinyl flooring throughout. Additional features include a private outdoor shower, BBQ area, its own washer and dryer, A/C, and two off-street parking spaces. The newly renovated 352 sq ft studio has been thoughtfully upgraded with marble finishes, a new tub, vanity, and flooring. The kitchen includes new cabinetry, full-size refrigerator, dishwasher, and garbage disposal. Additional highlights include high-end vinyl flooring, ample storage with a pantry and closet, a private lanai, an outdoor shower, and its own washer and dryer. Enjoy glimpses of the ocean along with stunning West Maui Mountain views. The property is also rich with mature fruit trees, including mango, tangerine, blood orange, lemon, banana, avocado, soursop, and lilikoi—perfect for those who appreciate island living and homegrown produce. This is a rare opportunity to own a versatile and private estate in one of Maui’s most desirable neighborhoods—offering the perfect blend of seclusion, flexibility, and convenience. Truly a slice of paradise. Property is being sold AS IS. Listing agent is related to the seller. Seller holds an Inactive RE License.
Home
4
bd
4
ba
2,804
sqft
$2,500,000
4
bd 4
ba 2,804
sqft
bd 4
ba 2,804
sqft
Exceptional 3Bed/3Bath with 1B/1.5B Detached Ohana in front, BOTH with Expansive Ocean views and wrap around decks. House has two wrap around decks with Ocean views from living areas, kitchen, and bedrooms. Vaulted ceilings with open floor plan. 1Bedroom Ohana has covered carport, large deck also with Ocean views from living area and deck. Buildings were painted and tented this year. Driveway was graded and new gravel just put in in May 2026. Fruit producing Manago tree in fenced back yard with BBQ and storage shed.
Home
3
bd
3
ba
2,055
sqft
$2,499,000
3
bd 3
ba 2,055
sqft
bd 3
ba 2,055
sqft
Home for sale
3450 Malina Pl Kihei, Maui Neighborhood: Maui Meadows
Enjoy incredible ocean views from this beautifully updated home and cottage located in the highly sought-after Maui Meadows neighborhood. Tucked away on a quiet cul-de-sac, this .59-acre property offers exceptional privacy surrounded by lush tropical landscaping, while the spacious pool and deck area create the perfect setting for relaxing or entertaining in true island style. The main residence has been recently remodeled and features high ceilings, a stunning chef's kitchen designed for both everyday living and hosting, as well as a loft that can be used as an office or private retreat. This custom pole house offers 3 bedrooms and 3 bathrooms with lanai spaces that seamlessly blend indoor and outdoor living. A separate 1-bedroom, 1-bath cottage provides excellent flexibility for guests or extended family. One of the unique highlights of this property is the unobstructed ocean views with no power lines in sight, enhancing the natural beauty of the setting. This is a truly special island home you won'tt want to miss. The location is unbeatable—peaceful and private, yet just minutes from the world-famous beaches, resorts, restaurants, shopping and golf courses. Your own tropical paradise awaits. Main residence is being sold furnished; the ?ohana is unfurnished
Home
4
bd
4
ba
3,296
sqft
$2,500,000
4
bd 4
ba 3,296
sqft
bd 4
ba 3,296
sqft
Home for sale
487 Hoala Dr Kihei, Maui Neighborhood: Maui Meadows
A true family home offering expansive living space and room to breathe. This beautifully renovated property features tasteful finishes throughout, a large wraparound deck with great ocean and mountain views, a spacious three-car carport, and a dedicated workshop. The main home includes an extended living area that's ideal for multigenerational living generous in size and conveniently located on the main level for easy access. In addition, there's a charming two-bedroom cottage with its own carport, plus a stunning resort-style pool perfectly tucked away for maximum privacy. This property is all about seclusion and comfort an exceptional Maui retreat. Not a drive-by, as it's impossible to appreciate all the features from the street. Enjoy your own backyard oasis with mature mango, papaya, and pomelo trees providing a fresh tropical harvest.
Home
2
bd
1
ba
704
sqft
$1,295,000 ▼ $40,000
2
bd 1
ba 704
sqft
bd 1
ba 704
sqft
Home for sale
3325 Mapu Pl Kihei, Maui Neighborhood: Maui Meadows
Tucked away at the end of a quiet cul-de-sac in highly desirable Maui Meadows, this charming island cottage offers the rare combination of privacy, usable land, and future potential just minutes from South Maui’s world-famous beaches. Set on over half an acre of lush tropical property, the 2-bedroom, 1-bath home embraces the relaxed indoor-outdoor lifestyle that makes Kihei so special. Vaulted ceilings and abundant natural light create an airy, welcoming atmosphere, while thoughtful upgrades—including a renovated kitchen and bath, split AC units, owned photovoltaic panels, and solar hot water—provide modern comfort and energy efficiency. The expansive lot offers exceptional flexibility, with ample space to build a larger main residence, expand the existing home, or explore additional possibilities. Mature landscaping and the peaceful upcountry-meets-coastal setting create a sense of seclusion, while Wailea, Keawakapu Beach, dining, shopping, and golf are all just moments away. Whether you’re searching for a private island retreat, an investment opportunity, or the foundation for your dream Maui estate, 3325 Mapu Place is a property filled with potential and unmistakable island charm.
Home
1
bd
1
ba
950
sqft
$1,299,000
1
bd 1
ba 950
sqft
bd 1
ba 950
sqft
Home for sale
3330 Kehala Dr Kihei, Maui Neighborhood: Maui Meadows
3330 Kehala Drive presents a unique opportunity in Maui Meadows with endless possibilities on one of the largest lots in the community. Spanning over a half acre, this property offers exceptional space, privacy, and flexibility in one of South Maui’s most desirable neighborhoods. Mature tropical landscaping and a serene, park-like setting create the ideal backdrop for creating your dream estate. The existing cottage is tucked away in a quiet and private location, providing comfortable living while you plan your vision. There is ample room to expand by building a main home all while capturing enchanting ocean and outer island views. The expansive grounds offer plenty of space for a pool, outdoor entertaining areas, gardens, or just about anything else you could imagine, allowing you to design a true Maui lifestyle compound. Whether you’re a first time home buyer looking to get into Maui Meadows or a general contractor seeking your next project, the upside and flexibility here are undeniable. Close proximity to the Wailea resort offers multiple amenities nearby. This is a special opportunity to create, customize, and unlock long term value in one of South Maui’s most sought after communities.
Home
3
bd
2
ba
1,585
sqft
$1,999,000
3
bd 2
ba 1,585
sqft
bd 2
ba 1,585
sqft
Privately positioned in Maui Meadows, 505 Ho'ohalahala offers exceptional space, flexibility, and privacy. Located just minutes away from resort amenities and resort beaches, this home delivers the Wailea location without the Wailea price tag. This fully fenced and gated estate provides a true sense of privacy with expansive, all usable grounds. Mature landscaping surrounds the property, reflecting the seller’s pride of ownership and years of thoughtful care. Situated on one of the larger lots in Maui Meadows, this property has been owned and cared for by the seller for decades. Ample parking accommodates multiple vehicles and there's an abundance of storage space for equipment. Perfect for a general contractor or those needing space to operate and thrive. Large pool with spacious adjacent shade cabana creates the ideal super private setting for outdoor entertaining or relaxing. The detached ohana is well separated from the main residence, offering excellent flexibility for guests or extended ohana. Well designed for multi generational living with space and tons of separation. Built in equity opportunity with lots of room to add value. Property is on a septic system eliminating future headaches. Opportunities like this don’t come around often in Maui Meadows.
$2.2m ▼ $150,000
614 Kupulau Pl unit 614 Kupulau Drive, Kihei
Home
4
bd
3
ba
2,215
sqft
$2,200,000 ▼ $150,000
4
bd 3
ba 2,215
sqft
bd 3
ba 2,215
sqft
Home for sale
614 Kupulau Pl unit 614 Kupulau Drive Kihei, Maui
Up to 3 units total. 3 Bed 2 Bath Main Dwelling + Attached Studio Ohana + 1 Bed 1 Bath Unattached Cottage Ohana with lanais on both buildings. Maui Meadows is renowned for its awe-inspiring ocean views. Prominently situated with a single level on the hillside, you'll discover within this contemporary elegant home, a spacious living-room kitchen area that seamlessly extends to the highlight of the property, an expansive covered lanai with breathtaking views of the ocean and outer islands. Watch the boats race to Molokini in the morning, or view the whales breach while grilling dinner with family and friends. This remarkable half acre property just underwent a complete transformation. Beautifully reimagined and thoughtfully finished, the Main Dwelling provides a large chef’s kitchen with high open beam ceilings, new floors, Quartz countertops, and stainless steel farmhouse sink, perfect for gatherings. From the living-room hallway, you will pass 2 Bedrooms and 1 Bath on your way to the Primary Suite, with large en-suite bath, which provides a perfect space for modern luxury living, complete with a 4 zone mini split AC system for your comfort. For added convenience, this contemporary residence is divided into three distinct living spaces. The Attached Studio Ohana is connected to the main dwelling through a solar service and storage closet, which can be used flexibly as a fourth bedroom with en-suite bath, or as a convenient grandmother's quarter's for rental income. Additionally, the Detached 1-bedroom, 1-bathroom Cottage Ohana with a covered lanai can provide steady rental income to help with island expenses or serve as extra living area for family, with ample locked indoor storage underneath. With 3 freshly updated units, this modern half acre is a great candidate for a future CPR subdivision, a process in which the detached cottage ohana and main dwelling could be sold separately, while a third unit could be possibly designated and another permitted detached ohana dwelling built. With such a large property, the possibilities stack up quickly. Come experience the luxury of island living in this contemporary versatile residence, nestled high in one of South Maui’s most desirable neighborhoods. All this just minutes from the beach, Wailea’s world-class restaurants, golf courses, and everything that South Maui has to provide. Contact your favorite Realtor today to schedule a showing! Digital staging used in some of MLS photos.
Home
4
bd
4
ba
3,399
sqft
$3,200,000 ▼ $300,000
4
bd 4
ba 3,399
sqft
bd 4
ba 3,399
sqft
Home for sale
744 Lanina Pl Kihei, Maui Neighborhood: Maui Meadows
Eclectic, exotic, bursting with energy this Maui Meadows home is such a special spot on the island with its breathtaking ocean views, deep tropical setting and exquisite finishes throughout. You will be Awestruck with the incredible design and finishes throughout this entire property with the beautiful pool, ideally situated for entertaining, lavish master suite and incredible chef’s kitchen. Every detail in this beautiful Polynesian style home has been perfectly appointed with a flexible three bedroom floor plan and Detached cottage that provides a great property and amenities for your perfect Maui dream home
Home
5
bd
4
ba
4,718
sqft
$6,999,000
5
bd 4
ba 4,718
sqft
bd 4
ba 4,718
sqft
Home for sale
135 Kaimanu Pl Kihei, Maui
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.
Home
2
bd
2
ba
1,469
sqft
$2,150,000
2
bd 2
ba 1,469
sqft
bd 2
ba 1,469
sqft
Property is also listed as Residential Condo MLS #407842 Located in one of South Maui’s most desirable neighborhoods, this beautifully maintained and thoughtfully designed plantation-style home seamlessly blends modern finishes with luxury and beach comfort. As you pass through the large front door you are greeted by a dramatic entrance with large foyer ceilings and an abundance of natural light. The downstairs area boasts one bedroom one bath with a private entrance. For added convenience, the lower level includes a kitchenette den area, with a wet bar and bunk beds, perfect for guests with small children. The area could also easily be converted to a third bedroom. Additionally, the ground floor provides an extra large two-car garage with plenty of storage for all your beach activities! The upstairs area includes a large chef’s kitchen with high ceilings, Italian tile floors, Quartz countertops and island, LG appliances, including a five-burner gas stove & stainless steel farmhouse sink, perfect for gatherings. Each zone of the house is equipped with its own Mitsubishi mini split-system air conditioner. From the living-room, the luxurious primary suite, with en-suite bath, and walk in closet provide a perfect space for modern luxury living, leading to the highlight of the upper level, a 30 foot viewing deck with breathtaking views of the ocean and neighbor islands. Maui Meadows is renowned for offering nightly serene sunset breezes under inviting pink and orange diffused skies. Though renovations are common, new construction in the neighborhood is extremely rare, and this house, constructed in 2017, was designed with one thing in mind, year-round sunset views. Watch the boats race to Molokini in the morning, or view the whales breach while grilling dinner for friends and family. This expansive property is a Residential CPR and includes 10,934 square feet while offering the potential to build an additional pool and spa hot tub, complete blueprints included. All this just minutes from the beach, Wailea’s world-class restaurants, golf courses, and everything that South Maui has to provide. Offered fully furnished, this beautifully landscaped, move-in-ready modern getaway is easy to view. Contact your favorite Realtor today to schedule a showing!
Home
3
bd
3
ba
3,028
sqft
$2,549,000 ▼ $146,000
3
bd 3
ba 3,028
sqft
bd 3
ba 3,028
sqft
Home for sale
3291 Waileia Pl Kihei, Maui Neighborhood: Maui Meadows
Luxury Spanish Villa in Wailea, Maui. Nestled in one of Wailea’s most sought-after neighborhoods, this meticulously upgraded contemporary Spanish villa blends timeless elegance with modern comfort. Situated on over half an acre of prime real estate and boasting over 5,000 square feet of living space under roof, this estate epitomizes luxury island living with single level living, having only the third bedroom upstairs. Recently reimagined, the home has undergone extensive renovations to seamlessly combine classic Spanish architectural elements such as 2' x 4' porcelain tiles and custom Moroccan pendant in kitchen with modern-day amenities.The iconic Spanish tile roof enhances the property’s curb appeal, while the grand entry and courtyard create a stately ambiance, welcoming you to your private sanctuary. Every detail has been thoughtfully upgraded in recent years, from high-end finishes such as European Oak wood floors, Hoppe windows and doors, Thermador appliances, to state-of-the-art systems such as Mitsubishi Air Conditioning and Luxe garage doors, ensuring a home that is both stylish and functional. The expansive outdoor living spaces include a large swimming pool, an inviting pool deck, and a covered lanai—perfect for entertaining or enjoying Maui’s year-round tropical climate. The property’s elevated position at the end of a quiet cul-de-sac provides unparalleled privacy and seclusion, free from through traffic. Inside, new air conditioning systems, premium finishes, and refined touches elevate the living experience. The oversized upper deck is a true showstopper, offering breathtaking ocean views, daily sunsets over the outer islands, and seasonal whale-watching opportunities. This estate is move-in ready and waiting to welcome its next discerning homeowner to indulge in tranquility, beauty, and exclusivity with proximity to Wailea and Makena's best beaches and resorts.
$2.4m ▼ $400,000
3300 Keha Dr, Kihei
Home
3
bd
3
ba
2,484
sqft
$2,400,000 ▼ $400,000
3
bd 3
ba 2,484
sqft
bd 3
ba 2,484
sqft
Home for sale
3300 Keha Dr Kihei, Maui
Amazing ocean and West Maui Mountain views from this three bedroom, three bath pole house in Maui Meadows on a flag lot. Enjoy the pool and spa together with the spectacular views.
$1.2m ▼ $196,000
769 Kumulani Dr, Kihei
Land
0.500
acres
$1,199,000 ▼ $196,000
0.500
acres
acres
Land for sale
769 Kumulani Dr Kihei, Maui
Prime 1/2 acre lot at the top of Maui Meadows. Located on the makai (ocean) side of Kumulani Dr. Ocean and Mountain views. Price is firm.