Refine Search
Map
Sort by
3264 Keha Dr, Kihei
$4,150,000
5 Beds ⋅ 5 Baths ⋅ 409863 MLS ⋅ Fee Simple Tenure
Three structures. Multiple living spaces. ¾ acre. 180-degree panoramic ocean/island views. Above Wailea in Maui Meadows, this pole-style property offers privacy, flexibility, and multiple residences. The MAIN RESIDENCE features 5 bedrooms and 4 baths / 2 half baths across 3 levels. The first level includes a kitchen and living room opening to an ocean-view lanai, primary bedroom and 2nd bedroom with Jack-and-Jill bath. The level below offers a 2nd living area, an ensuite bedroom with an adjoining bedroom currently used as a gym, powder room, office, laundry, and another lanai. The 3rd level is a 1-bedroom apartment with its own entrance, kitchen, living room, and bath. Outside, enjoy a pool, tiki bar, sauna, BBQ area, garage, and carport. The SECOND STRUCTURE is a separate 2-bedroom, 1-bath ohana with kitchen, living room, 3-car garage, and office/studio. The THIRD STRUCTURE is a 1-bedroom, 1-bath cabin. Turn-key and fully furnished, the property includes 71 solar panels, smart-home features, tropical landscaping, koi pond, waterfalls, and mango, avocado, Meyer lemon, and banana trees. The home features a Wolf range, Sub-Zero refrigerator/freezer, and Fisher & Paykel appliances. Views include Kaho'olawe and Lana'i. Rarely available combination of acreage, multiple living spaces, and resort amenities.

3264 Keha Dr, Kihei

Listing courtesy of eXp Realty.

3387 Kuaua Pl, Kihei
$3,850,000
3 Beds ⋅ 3 Baths ⋅ 408127 MLS ⋅ Fee Simple Tenure
You want it all? Well, you will find it at 3387 Kuaua. This is that home that has everything everyone wants…amazing ocean views from nearly every room, single level living, beautiful infinity edge pool, 3 large bedrooms plus an office with a beautiful Wall bed, which can be used as another bedroom. The primary suite is to die for with a huge walk-in closet, outdoor shower, and a large tub. There is also a den, and open concept great room. Spacious chef’s kitchen, Exceptional outdoor kitchen with an ice maker and gorgeous grill with a view. Large laundry room, beautiful showcase, garage with workshop and a detached two bedroom cottage completely out of the way from the main house.

3387 Kuaua Pl, Kihei

Listing courtesy of Hawaii Life (W).

440 Mikioi Pl, Kihei
$2,975,000
5 Beds ⋅ 6 Baths ⋅ 408281 MLS ⋅ Fee Simple Tenure
Located in the desirable Maui Meadows community, this exceptional South Maui estate offers quality craftsmanship, flexible living, and complete privacy in a lush tropical setting. Designed and owned by an award-winning contractor, the home reflects refined detail and superior finishes throughout. Set on a half-acre parcel with expansive ocean views, the property features a private pool oasis with cascading waterfall, surrounded by vibrant gardens and mature landscaping. The main home offers an open floor plan with seamless indoor-outdoor flow, ideal for entertaining or relaxed island living. Two detached ohana's provide options for extended family, guests, or rental income. A spacious 4-car garage and high-clearance storage garage add functionality, while photovoltaic solar and split-system A/C throughout enhance efficiency. A private and peaceful retreat that embodies Maui luxury living, just minutes away from South Maui's beaches, dining, and shops.

440 Mikioi Pl, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

634 Laniolu Pl, Kihei
$2,500,000
3 Beds ⋅ 4 Baths ⋅ 409054 MLS ⋅ Fee Simple Tenure
A treasure chest of wonder can be yours in this enchanting Maui Meadows Crown Jewel. Perched at the crest of a quiet cul-de-sac, offering unmatched privacy, this panoramic estate offers a masterclass in island living, and rarely found in South Maui. Unobstructed Ocean, Haleakala and Molokini and the outer island views. Situated on a pristinely manicured half-acre, the property is one of a select few featuring a private, professional-grade tennis court alongside an 11-foot deep custom pool adorned with a variety of sculptures. The main residence boasts three spacious en-suite bedrooms, a gourmet custom kitchen featuring rich Koa wood cabinetry and elegant Parquet flooring, and wrap-around lanais designed to capture unobstructed ocean and Haleakala views. Inside, the home features motorized skylights and vaulted ceilings which invite natural light and gentle breezes. Wander through Zen-inspired Japanese gardens complete with Koi ponds and stone bridges. Whether you are creating in the large art studio or entertaining on the expansive wrap-around deck, every corner of this half-acre property feels like a getaway. With a beautiful tile roof (2010), new 33 panel grid-tied photovoltaic system with tesla battery backup (leased), two-car garage, solar hot water, outdoor shower, ample storage, this estate blends timeless island elegance with practical design for tropical living.

634 Laniolu Pl, Kihei

Listing courtesy of Emerald Club Realty Inc.

759 Kumulani Dr, Kihei
$2,475,000
5 Beds ⋅ 4 Baths ⋅ 407966 MLS ⋅ Fee Simple Tenure
Welcome to 759 Kumulani Dr, this beautiful home sits a top of one of the highest streets in Maui Meadows. This spacious 5-bedroom, 3.5-bath residence with an attached studio offers a serene location with a variety of living scenarios. On the main level, you will find a primary en-suite bedroom plus a second bedroom, powder room, living room, view decks, kitchen, and a separate full-size laundry. Downstairs, you’ll find 2 additional primary en-suite bedrooms, a larger living-game area, plus a third bedroom. There is also a small updated kitchen and laundry area. The space is ideal for guests, extended family, or larger families seeking separate living quarters. On the south side of the property, the attached studio is currently being used as an art studio but provides flexibility for use as a creative space, home office, or private retreat. It could also be rented as it has a full bathroom. This house offers an ultra-private, oversized heated pool/spa and lounge area. This location provides the ultimate Hawaii experience, offering owners a quiet, private place to unwind with nature.

759 Kumulani Dr, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

487 Hoala Dr, Kihei
$2,300,000
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).

904 Kupulau Dr, Kihei
$2,235,000
3 Beds ⋅ 5 Baths ⋅ 404030 MLS ⋅ Fee Simple Tenure
Step into an extraordinary Modern Pole House, gracefully perched at the top of Maui Meadows, where breathtaking panoramic ocean views and vistas of the neighboring islands await you. Meticulously remodeled and completed in 2021, this architectural masterpiece seamlessly blends contemporary elegance with the unique charm of the original Frank Stiller design. This property is very private, with stunning ocean views and amazing Maui sunsets visible throughout the home. Unwind in the serene ambiance by the saline pool, perfectly positioned for both privacy and tranquility. The exterior boasts a lush, large front yard covered in golf course-quality grass, adding to the home’s impressive curb appeal and offering a perfect space for play, relaxation, or entertaining. Surrounded by a tropical landscape with mature fruit trees—including orange, mango, banana, and papaya—the property embodies the enchanting allure of a private treehouse retreat. With over 1,700 square feet of expansive wraparound lanais, automatic sprinklers, and outdoor landscape lighting, every detail enhances the beauty of this tropical oasis. Step inside to a bright, airy interior showcasing soaring open-beam ceilings, generous windows, and an effortless indoor-outdoor flow that invites cooling cross breezes. Each room is equipped with split A/C systems, ensuring your comfort in every season. The primary suite is a true sanctuary, offering double closets and a luxurious en-suite bathroom with dual sinks, two spacious showers, and two toilets. Elegant double LED-lit vanity mirrors enhance the sophistication of this exquisite retreat. Luxurious porcelain tile floors and beautifully crafted monkeypod, mango, and cypress wood counters add a refined, natural touch throughout. Downstairs, the lower level offers additional living space with a full bathroom, kitchenette, and its own washer/dryer hookup—ideal for guests or extended family. Additionally, this area includes a 4th bedroom with separate access, creating the perfect opportunity for a flexible use space that could serve as a private office, guest suite, or even a separate ohana. Embracing sustainability, the home features 34 fully owned PV solar panels and an upgraded septic system. For pet lovers, there's a fully fenced area for your furry companions to enjoy the outdoors safely. A detached garage provides a versatile workshop area with a half bath, and ample parking is available via upper and lower driveway access. Whether you’re lounging poolside or entertaining on the spacious lanais, this Maui retreat is designed to elevate your island living experience to new heights.

904 Kupulau Dr, Kihei

Listing courtesy of Keller Williams Realty Maui-Ki.

3379 Kehala Dr, Kihei
$2,200,000
2 Beds ⋅ 3 Baths ⋅ 407372 MLS ⋅ Fee Simple Tenure
UNIQUE single-level home on well-landscaped, 1/2 acre lot. Expansive front yard with nice ocean and mountain views. Private backyard with large, tiled pool. Well-planned improvements: new rock walls at front and sides, cesspool to septic conversion, upgraded A/C, upgraded electric, 52 solar panels with net metering, new roof and more. Separate 2 car garage with full bath and guest room. Additional parking in 3 stall carport. Make sure and see this home—it is fantastic as is, but if expansion is on your mind, this is an ideal opportunity! Seller is a licensed Realtor in Hawaii.

3379 Kehala Dr, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

758 Lanina Pl, Kihei
$1,875,000
3 Beds ⋅ 3 Baths ⋅ 407171 MLS ⋅ Fee Simple Tenure
Perched at the top of Maui Meadows is this well-built elegant but simple 3 bed 3 bath island style, pole home. Astounding wrap around lanai for taking in outer island, ocean and mountain views! Just as you enter the gated property, and below the main house, is a cute 1 bedroom 1 bath ohana with its own private garden setting. In between the main house and ohana, is a landing with plenty of space to create your dream garden. Great for picking mango in season and flowers all year round. Extra bonus there is 4th room off the main house lanai. Great for a little space for work or creative hobbies! This home will make you want to share your time, watch sunsets and make new memories, all while watching the whales swim by in season. This special nest is looking for new inhabitants to embrace its sense of peace and zen as you create a beautiful life within. Grab this rare opportunity to make the most of your life, happen here!

758 Lanina Pl, Kihei

Listing courtesy of The Agency Maui.

3248 Akala Dr, Kihei
$1,592,000
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. 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).

521 Kupulau Dr, Kihei
$1,550,000
3 Beds ⋅ 2 Baths ⋅ 404409 MLS ⋅ Fee Simple Tenure
Nestled in the highly sought-after Maui Meadows neighborhood, this unique pole home on Kupulau Drive offers breathtaking views as you approach the covered lanai and front entry. The open-concept living area, featuring lots of windows, redwood walls and high ceilings, offers plenty of flexibility and captures stunning ocean and mountain vistas. The wrap-around covered deck enhances the home's connection to the outdoors. The kitchen has ample work space and opens to the dining area that includes a built-in china cabinet.  An additional room provides the perfect space for an office or study. The primary bedroom, located on one side of the home, opens directly to the deck, providing both privacy and views. On the opposite side, the second and third bedrooms share a very nice bath. The lower level offers extended living space with patio and yard access, as well as a small kitchen, two bedrooms, and a bath. The garage has an adjoining workshop area. In the backyard, a gazebo offers a cozy retreat looking over the yard & enjoying views too. While the property does require updating, it features a spacious, open layout with versatile interior spaces. The structure is supported by poles, providing a great opportunity for creative customization. Set on a generous lot, there's plenty of room for two detached cottages, making this a perfect opportunity for those with vision to transform this tropical retreat into your dream property!

521 Kupulau Dr, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

500A Mikioi Pl, Kihei
$1,535,000
1 Beds ⋅ 1 Baths ⋅ 408119 MLS ⋅ Fee Simple Tenure
Discover a sanctuary of privacy, charm, and hand-crafted beauty in this lovingly built Maui Meadows haven. Set on a lush and secluded half-acre, this special property offers a main house, a separate cottage, and a “Hooch” shed—all surrounded by vibrant tropical greenery, including mature mango, banana, and papaya trees. The moment you arrive, you feel a sense of peace, space, and possibility. The main house is a warm, custom creation featuring 1 bedroom, 1 office and a bathroom, elevated by thoughtful details and a soulful, handmade aesthetic. A wraparound covered lanai invites you to unwind, dine, and take in the ocean views. A charming ladder leads to a loft, perfect for storage or creative inspiration. There’s an additional 500 square feet of covered outdoor workshop area connected to the home, great for those who love outdoor projects and gardening. Tucked away with its own privacy and character, the 2-bedroom, 1 bathroom cottage is equally as lovely, offering its own 310 sq ft wraparound lanai as well as its own private yard—a peaceful spot for guests, extended family, or rental potential. Scattered pathways, open yard space, and pockets of shade beneath fruiting trees create an environment that feels both expansive and intimate. Every corner of the property reflects care and creativity. This property is truly a gem in Maui Meadows.

500A Mikioi Pl, Kihei

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

3100 Mapu Pl, Kihei
$1,530,000
2 Beds ⋅ 2 Baths ⋅ 406342 MLS ⋅ Fee Simple Tenure
Tucked into the cooler, elevated slopes of South Kihei’s desirable Maui Meadows neighborhood, this serene property offers a rare combination of privacy, space, and flexible living. Set on a gently sloping half-acre+ lot framed by a striking lava rock wall, the lush grounds are a tropical haven filled with mature landscaping and prolific mango trees. The beautifully renovated 2-bedroom, 2-bath main residence (1,536 sq ft) underwent a comprehensive update in 2016, showcasing a thoughtful blend of island charm and modern comfort. In 2020, a spacious lanai was added, creating a seamless indoor-outdoor flow perfect for sunset dinners, entertaining, or quiet evenings under the stars. Built with quality in mind, the home features double-pane windows and cement-filled hollow tile construction for enhanced soundproofing and peaceful living. A 2-car garage adds convenience and functionality. Nestled at the back of the property, the detached 1-bedroom, 1-bath cottage (620 sq ft) offers privacy and flexibility, complete with its own separate driveway and large screened-in covered lanai—an ideal space for al fresco dining, morning coffee, or creative work. The former carport has been thoughtfully enclosed, expanding the cottage’s usable space. This Maui Meadows gem offers the perfect balance of tropical tranquility and modern ease—just minutes from Kihei’s beaches, restaurants, and shopping, yet set apart in its own private oasis.

3100 Mapu Pl, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

3414 Keha Dr Unit Unit B, Kihei
$1,475,000
2 Beds ⋅ 1 Baths ⋅ 407896 MLS ⋅ Fee Simple Tenure
Enjoy sweeping ocean, outer-island, and West Maui Mountain views from this brand-new Maui Meadows home, crafted with exceptional attention to detail and elevated design. Perfectly perched to capture the panorama, this thoughtfully planned 2-bedroom, 1-bath residence blends refined finishes with a relaxed island living experience. Expansive windows and a 3-panel sliding door frame the wide, unobstructed ocean vista—your daily backdrop of shifting blues, golden sunsets, and colorful evening skies. The generous covered lanai extends the living space outdoors, creating an ideal setting for morning coffee, evening dinners, or simply taking in the ever-changing horizon. Inside, the home offers a warm, modern aesthetic with cohesive high-end finishes throughout. Quality wide-plank oak flooring, soft-close cabinetry, Taj Mahal quartzite counters, and an efficient, well-designed kitchen highlight the main living area. Beautiful tilework, contemporary fixtures, and tall doors enhance the home’s clean lines and sense of openness. Built with long-term comfort in mind, the home features full insulation, an efficient split A/C system, and smart-home upgrades for effortless day-to-day living. The fully fenced property includes an electric entry gate, low-maintenance landscaping with irrigation, and an outdoor shower—perfect after beach days or island adventures. A spacious EV-ready garage provides excellent storage and flexibility. With its elevated views, thoughtful design, and quality craftsmanship, this new Maui Meadows residence offers a rare blend of comfort, style, and indoor–outdoor living in one of South Maui’s most desirable neighborhoods. This property is a residential CPR.

3414 Keha Dr Unit Unit B, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

3325 Mapu Pl, Kihei
$1,200,000
2 Beds ⋅ 1 Baths ⋅ 409258 MLS ⋅ Fee Simple Tenure
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.

3325 Mapu Pl, Kihei

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

3467 Malina Pl, Kihei
$750,000
409599 MLS ⋅ Fee Simple Tenure
Grandiose views within one of South Maui's most coveted neighborhoods. This spacious 25,744 sq. ft. lot in sought-after Maui Meadows offers a truly rare chance to design and build your custom island retreat from the ground up! The canvas is clean, complete with building locations, septic, and ready for your vision. Maui Meadows is renowned for its large lots, cool upcountry breezes, and stunning ocean and mountain views — and this parcel delivers on all counts. Tucked on quiet Malina Place, you're just minutes from the world-class dining, shopping, and white-sand beaches of Kihei and Wailea, including Keawakapu, Ulua, and Maluaka beaches. Whether you're envisioning a luxurious single-family estate, a multi-generational compound, or an investment property, the generous lot size gives you the space and flexibility to make it happen. Surrounded by high-quality homes in one of South Maui's premier residential communities, this is the kind of opportunity that rarely comes to market. Come build something extraordinary.

3467 Malina Pl, Kihei

Listing courtesy of Century 21 Island Homes.

3546 Akala Dr, Kihei
$750,000
407947 MLS ⋅ Fee Simple Tenure
Huge price drop! If this doesn't get you off the fence, nothing will. Don’t miss your chance to secure one of the few remaining vacant lots in Maui Meadows. This half-acre property offers the perfect canvas for your dream home, ideally situated just minutes from world-renowned resorts, white sandy beaches, world-class golf courses, premier shopping, and top-rated dining. Great building site with mountain and ocean views, providing the ultimate backdrop for island living. Whether you’re looking to build a private retreat or a luxury masterpiece, this lot delivers incredible potential in one of Maui’s most sought after communities. Opportunities like this are rare, contact your favorite Realtor today!

3546 Akala Dr, Kihei

Listing courtesy of Pono Real Estate LLC.

How much is your home worth?

Get instant property value now!