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$1,900,000
3 Beds ⋅ 3 Baths ⋅ 410160 MLS ⋅ Fee Simple Tenure
Located in the highly desirable neighborhood of Maui Meadows, 3248 Akala Drive offers a spacious and well maintained property situated on a beautifully landscaped ½-acre lot. The thoughtfully updated main residence features a wraparound deck with ocean views, a PV system, and a tile roof. The main home offers a flexible floor plan with the primary suite, additional bedroom, full bathroom, kitchen, and living area located upstairs. The kitchen is beautifully appointed with granite countertops, wood cabinetry, tile finishes, and stainless steel appliances. The lower level includes an additional bedroom, full bathroom, and family room, providing added space for guests, family, or a home office. Also located on the lower level is a one-bedroom, one-bath ohana with a private entrance and lanai, offering excellent versatility for guests, extended family, or rental potential. A detached one-bedroom, one-bath cottage at the front of the property features its own private and spacious covered outdoor living area. With a single-car garage and ample additional parking, this property provides the space and flexibility. Whether you are looking for multi-generational living, rental opportunities, or your own private island retreat, this property offers privacy, comfort, and the Maui lifestyle you've been waiting for.

3248 Akala Dr, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$3,060,000
3 Beds ⋅ 3 Baths ⋅ 410168 MLS ⋅ Fee Simple Tenure
Nestled in the sought-after community of Maui Meadows, this exceptional property offers breathtaking views, flexible living spaces, and resort style amenities. The main residence features 3 bedrooms and 2.5 baths. The ground level offers an open concept great room with living, kitchen, and dining areas and broad ocean views. Expansive bi-fold doors open to a spacious covered lanai. A generously sized bedroom with en-suite bath offers the option for a primary suite on the main level. An additional bedroom currently serves as an office. The upper level primary suite opens to a private lanai with serene Haleakala and ocean views. Crowning the home is a rooftop deck that offers 300 degree views from the North Shore to Lanai to Haleakala summit. Offer your guests the pool house suite. It is the ultimate in privacy, with a guest room and a full bath, plus an outdoor kitchen. There's even a large screen for enjoying movies or sports on our warm Maui nights. Relax beside the tropical pool or join a game of cornhole or bocce ball on the adjacent lawn. A detached 1 bedroom, 1 bath cottage offers additional living space or an option for rental income. Orange, mango, avocado, lime, lemon, and lilikoi are there for your enjoyment! Completed in 2022, this exceptional residence is the newest home currently available on the market in Maui Meadows. Don't miss this one! It's a gem!

3220 Waileia Pl, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$4,500,000
5 Beds ⋅ 4 Baths ⋅ 409863 MLS ⋅ Fee Simple Tenure
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.

3264 Keha Dr, Kihei

Listing courtesy of eXp Realty.

$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.

$1,999,000
2 Beds ⋅ 2 Baths ⋅ 409663 MLS ⋅ Fee Simple Tenure
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.

3161 Mapu Pl, Kihei

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

$2,500,000
4 Beds ⋅ 4 Baths ⋅ 409511 MLS ⋅ Fee Simple Tenure
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.

3275 Kehala Dr Unit 3275 A Kehala Dr, Kihei

Listing courtesy of AOK Properties LLC.

$2,499,000
3 Beds ⋅ 3 Baths ⋅ 409471 MLS ⋅ Fee Simple Tenure
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't 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

3450 Malina Pl, Kihei

Listing courtesy of Wailea Point Realty, Inc..

$2,500,000
4 Beds ⋅ 4 Baths ⋅ 409304 MLS ⋅ Fee Simple Tenure
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.

487 Hoala Dr, Kihei

Listing courtesy of Hawaii Life (W).

$1,999,000
3 Beds ⋅ 2 Baths ⋅ 409237 MLS ⋅ Fee Simple Tenure
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.

505 Hoohalahala St, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$6,999,000
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).