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59 Wailea Gateway Pl Unit 4-101, Kihei
$2,895,000
3 Beds ⋅ 2 Baths ⋅ 409559 MLS ⋅ Fee Simple Tenure ⋅ Keala O Wailea BLDG.
Welcome to modern Hawaiian luxury at Keala o Wailea Unit 4-101. This rare 3-bedroom, 2-bathroom residence offers effortless single-level living with absolutely no stairs in an exclusive, pet-friendly gated community. Premiere ground floor units in this community rarely come up for sale. Offered fully furnished and turnkey, the home features a soothing, neutral coastal aesthetic. The open-concept living area is highlighted by large retractable glass doors that create seamless indoor/outdoor living. Step onto your spacious covered lanai to soak in massive ocean views spanning Kaho'olawe, Molokini, West Maui and Lanai, all while overlooking the Wailea Blue Golf Course. The gourmet kitchen is equipped with sleek contemporary cabinetry, elegant quartz countertops, and premium Bosch appliances. Every detail is thoughtfully designed for comfort and elevated island living. Due to its location in the center of the complex, the unit is conveniently located near the amenities including a stunning ocean-view pool, spa, fitness room, and clubhouse with BBQ facilities This unit includes two parking spaces, featuring a covered carport with built-in storage, and a second space which is just steps from the front door. There is access to additional storage for your recreational equipment. You are also situated immediately adjacent to the Wailea Gateway Shops, putting exceptional dining, shopping, fitness facilities, doctor's office and a pharmacy just a short stroll from your front door. Experience the pinnacle of quiet, contemporary Wailea living in Unit 4-101, where breathtaking vistas, sophisticated design, and everyday convenience perfectly align.

59 Wailea Gateway Pl Unit 4-101, Kihei

Listing courtesy of Hawaii Life (W).

965 Hog Back Rd, Haiku
$2,895,000
3 Beds ⋅ 4 Baths ⋅ 408112 MLS ⋅ Fee Simple Tenure
It’s time for you to own your escape to this four-acre rural-zoned property on Maui's North Shore. Wake to the sound of the warm trade winds gently swaying the trees. Stroll in your expansive yard picking fresh fruit to complement your morning smoothie. Sit with your favorite book in your treehouse perched over a lush forest, dappled with sunshine. Catch a rainbow and end your day soaking in your outdoor bath, watching the sun set. Your idyllic Maui escape is ready: 965 Hog Back Road. At the end of a country road, tucked behind a majestic Royal Poinciana tree, sits a true North Shore treasure. Originally designed by renowned Maui architect Harry Rice and now reborn as a mid-century modern retreat, the home is elegantly enveloped by more than four acres of lush, private gardens. Light-filled living spaces open to expansive lanais and a spa-like outdoor bath featuring a 72” concrete soaking tub and custom shower. The gourmet kitchen boasts a 48” Hestan gas range, paneled Hestan refrigerator, European-style cabinetry, and a dedicated pantry/prep area. The 3,100 sq. ft. home features 3 spacious bedrooms, each with a luxurious ensuite bath, plus a separate upgraded cottage ideal for guests. A custom eucalyptus spiral staircase and handcrafted details throughout accentuate the classic Maui roots. **This property features language in its bylaws stating that the property can be further CPR'd unilaterally; this can be a large benefit, especially since it is zoned rural half-acre. ** Mature fruit trees, peaceful walking paths, and a treehouse overlooking the forested gulch create a private, retreat-like setting. All the home's amenities and features, accompanied with North Shore conveniences, make this a truly unique architectural treasure. This is an A unit of a CPR.

965 Hog Back Rd, Haiku

Listing courtesy of Hawaii Life (W).

210 E Ikea Moku Pl, Kihei
$2,888,000
3 Beds ⋅ 3 Baths ⋅ 411381 MLS ⋅ Fee Simple Tenure
Wonderful Wailea home with an exceptional sense of space and flow. This thoughtfully designed floor plan features two generous master suites: one opening to a beautiful ocean-view lanai, and the other offering a private office area and a large storage closet. The main level also includes a bright, airy office and a third bedroom. At the heart of the home is a renovated, open-concept kitchen that seamlessly connects to the living and dining areas, creating an inviting great-room feel. Large sliding patio doors lead directly to the pool, hot tub, and lanai, allowing the home to open wide and truly embrace indoor–outdoor living, all while offering exceptional privacy. Located in the gated community of Wailea Kialoa, this home is just minutes from world-class beaches and outstanding shopping.

210 E Ikea Moku Pl, Kihei

Listing courtesy of Hawaii Life (W).

4000 Wailea Alanui Dr Unit 3404, Kihei
$2,795,000
2 Beds ⋅ 2 Baths ⋅ 408567 MLS ⋅ Fee Simple Tenure ⋅ Wailea Point I Ii Iii BLDG.
You Deserve To Own & Experience Your Oceanfront Paradise Today! Unit 3404 is a delightful 2 bedroom, 2 bathroom upper-level, privately located, & meticulously maintained residence, within the highly-coveted, low density, lushly landscaped, & world-class tropical paradise known as Wailea Point. Upon entering the residence, you are transfixed by the lovely pastoral-framed Ocean, Molokini Crater, & Island of Kaho’olawe views. The award-winning construction & design affords vaulted 16-ft Clear Cedar ceilings, perimeter soffits with recessed art lighting, & book-matched Hawaiian Koa doors & accents throughout, which exude a feeling of warmth & elegance. The recent installation of floor-to-ceiling mitered glass bay windows in the great room brings in volumes of natural light, & creates mesmerizing views of the ocean & outer islands, breaching whales, & painterly sunsets. The open & functional design in the kitchen, with glass-on-glass corner windows, allows for scenic views while creating gourmet culinary delights. The spacious primary bedroom, with a Clear Cedar ceiling & recessed lighting, is filled with natural light & offers an en-suite private bathroom, & garden views from its dedicated lanai. The guest suite's wall of glass allows for extra light & tropical garden views. The spacious & tranquil wrap-around lanai offers lovely ocean views, alfresco dining, an upgraded built-in BBQ area, & electronic privacy sunshades. The laundry room features a full-size washer & dryer, ample storage & counter space. There is also a deeded 1 car garage with an electric car charge connection that comes with the residence. Wailea Point is prominently positioned upon 28 prime pastoral oceanfront acres in the world-class Wailea Resort area, adjacent to the Four Seasons Maui & Fairmont Kea Lani. Experience ‘The Best’ that Maui has to offer, as you drive your golf cart or meander through the property, enjoy direct access to two of Maui’s most iconic beaches & the adjacent 1.5-mile oceanfront 'Wailea Walk', & explore fine dining & shopping at The Shops at Wailea or relax in the luxury spas of Maui's finest resorts. World-class golf is conveniently nearby, & tennis & pickleball courts are located onsite. The complex offers guard-gated & 24-hour roving security. Second to none on Maui are the two on-site recreation pavilions; one is family-oriented & includes a lap pool, kids' pool, cold plunge & state of the art gym, while the other is the 'quiet' pool area. Savor the best of Maui, at Wailea Point 3404!

4000 Wailea Alanui Dr Unit 3404, Kihei

Listing courtesy of Maui Real Estate Advisors LLC.

500 Bay Dr Unit 28B2, Lahaina
$2,750,000
2 Beds ⋅ 3 Baths ⋅ 411350 MLS ⋅ Fee Simple Tenure ⋅ Kapalua Bay Villas Ii BLDG.
Front row on the Kapalua coastline, with nothing between you and the Pacific. Now offered at an improved price, this is the best value for a front-row villa at Kapalua Bay Villas. No rooftops and no neighbor’s lanai in the way, just open ocean, Molokai and the sunset. You walk in from the bridge with no stairs, and that combination is hard to find at any of the villas!  And this remodeled 2 bedroom, 3 bath townhome-style villa comes turnkey, sold furnished with newer high-end furnishings, and has a track record as a successful vacation rental. The view is what makes this unit so desirable. Molokai frames your view across the channel, and Kapalua’s rugged volcanic coastline curves along beside it. The villa sits up high above a rocky shoreline, so there’s no seawall to maintain and no erosion to worry about. More and more of West Maui’s sandy shoreline is struggling with erosion, so that’s a real advantage. You get the ocean view without the ocean problems. The living room opens wide to a private lanai, so inside and outside run together and the ocean feels like part of the room. Have your coffee out there in the morning and come back for sunset. Kapalua’s weather is about as close to perfect as Maui gets. It stays mild and breezy, and every so often a quick passing shower blows through that’s too light to bother with an umbrella. Most days, you’ll live with the doors and windows wide open and let the trade winds do the work. On the warmer afternoons, close up and switch on the central air. Areas to the south run hotter and drier, so up here you get to pick your climate. The open kitchen has granite counters, stainless appliances and plenty of cabinets. It stays connected to the living area and lanai, so whoever’s cooking still gets the view. The remodel is polished, but it’s comfortable enough to live in, sandy feet and all. Then you go upstairs. You’d think the view couldn’t get any better, and the primary bedroom proves you wrong. From up there, the ocean fills the whole frame, Molokai floats on the horizon and the coastline keeps going. You’ll wake up to it, fall asleep to it, and it doesn’t let up. Each bedroom is a suite with its own lanai and its own bathroom with a walk-in shower, and built-in storage keeps everything organized. The land is what sets Kapalua Bay Villas apart. It’s a fee simple oceanfront community of just 141 condos in 27 1-story and 2-story buildings, spread across 16.45 acres. That works out to roughly 5,000 square feet of land per unit, which makes it one of the largest deeded condo land holdings on Maui. Your pro rata share of the land is bigger than at most condo complexes on the island, and the density is low, so it feels open, quiet and green. The grounds include pools, a clubhouse, barbecues and tennis and pickleball courts. Oneloa Bay (Ironwoods Beach) and Kapalua Bay are both an easy walk away, and the Kapalua Coastal Trail runs along the shoreline through one of the prettiest stretches of West Maui. Beyond your door, the Kapalua Resort has fine dining, shopping, golf, hiking, whale watching, snorkeling, the Kapalua Tennis Garden, Kapalua Zipline, The Spa at Kapalua Bay, Honolua Bay and the world-renowned D.T. Fleming Beach.

500 Bay Dr Unit 28B2, Lahaina

Listing courtesy of Real Broker.

277 Keonekai Rd, Kihei
$2,750,000
7 Beds ⋅ 4 Baths ⋅ 410789 MLS ⋅ Fee Simple Tenure
Located on desirable Keonekai Rd, this newly renovated home comes with a brand new stainless steel roof. The main residence features 3 bedrooms and 2 bathrooms, with an attached ohana that can be opened via an internal connecting door to create a flexible 5-bedroom, 2-story layout on the ground floor — ideal for extended family or rental income. Upstairs of the ohana unit is 2 more bedrooms and a full kitchen, connecting to downstairs via interior stairs. Enjoy a spacious backyard, two-car garage, and additional storage room and laundry facilities. Conveniently located near Kihei beaches, shopping, dining, schools, and just minutes from Wailea and South Maui amenities. A great opportunity for buyers looking for space, flexibility, and a move-in-ready home or investment property in a convenient Kihei location. Bedroom/bathroom count as marketed does not match TMK records. Buyer and buyer's agent to conduct their own due diligence.

277 Keonekai Rd, Kihei

Listing courtesy of Fortress Realty Hawaii LLC.

78 Kai Malu Dr Unit 202 (14D), Kihei
$2,750,000
2 Beds ⋅ 2 Baths ⋅ 409643 MLS ⋅ Fee Simple Tenure ⋅ La'i Loa BLDG.
Experience elevated island living at La‘i Loa Wailea, Wailea’s newest luxury condominium development, in this beautiful 2-bedroom, 2-bath 1,374 sq. ft. residence offering beautiful ocean and Molokini views from the spacious lanai. Designed to embrace Maui’s coveted indoor-outdoor lifestyle, this luxury condominium blends modern elegance, comfort, and resort-style amenities within one of South Maui’s most sought-after gated communities. This lovely residence features tile flooring throughout the unit, creating a seamless and sophisticated coastal aesthetic. The expansive lanai is enhanced with privacy shades to help block the afternoon sun while providing the perfect setting to enjoy year-round sunsets, ocean views, and Molokini vistas. Airflow and comfort are thoughtfully enhanced by sleek Big Ass Fans throughout the residence, complementing the home’s relaxed yet refined island aesthetic. The open-concept design seamlessly connects the kitchen, dining, living, and lanai spaces, creating an effortless flow for entertaining or everyday indoor-outdoor living. Additional features include an EV charger, extra storage, and the convenience of two parking spaces, including a 1-car garage and 1-surface stall. La‘i Loa residents enjoy exceptional resort-style amenities including a stunning 75-foot lap pool, beautifully designed amenity center, fitness room, sauna, and steam sauna. Thoughtfully designed by award-winning Weinstein A+U Architects, the gated community offers privacy, security, and contemporary island architecture in the heart of Wailea. Located moments from Wailea’s world-renowned beaches, golf courses, luxury resorts, shopping, and dining, this is an exceptional opportunity to own in one of Maui’s premier luxury communities.

78 Kai Malu Dr Unit 202 (14D), Kihei

Listing courtesy of Polaris Pacific.

50 Kaalele Pl, Kula
$2,700,000
4 Beds ⋅ 3 Baths ⋅ 411081 MLS ⋅ Fee Simple Tenure
At the top of Kula’s sought-after Kulamanu neighborhood sits Kaalele Place: where the sunlight reflects off the manicured hedgerows, framing some of the best views on the island. As you approach the very top of the neighborhood, 50 Kaalele Place comes into view. With striking Hawaiian-style architecture, its presence will make you proud to call it home. Unobstructed five-island views from the entire main floor (including the luxurious primary suite), impeccable high-end finishes, a curb appeal rarely found in Upcountry: this is the house that asks you to compromise absolutely nothing. Long-term guests and family will appreciate the private lower level, with its own expansive living areas, 1-car garage, as well as a spacious full bath and bright guest bedroom with walls of windows. The star of the show, however, is the main level. After entering through the automatic gate clad with exotic hardwood, pull into your oversized 2-car garage, and enter your home, only to be greeted by views that will take your breath away, day or night. This level boasts tall wood-accented ceilings, a primary suite you will never want to leave, a stunning two-sided fireplace, a chef’s kitchen with a SubZero refrigerator and Wolf gas range, two additional bedrooms, an additional full bath, and a lanai framed by high-end zero-maintenance aluminum Knotwood railing and pillars. With whole-house water filtration, a top-of-the line solar + Tesla battery system that all-but eliminates your grid reliance, and the ability to live exclusively on one level if desired, this house thought of everything - so you don’t have to. No to-do lists, no compromises, no worries - 50 Kaalele Place is a home you can take the time to enjoy.

50 Kaalele Pl, Kula

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

41 Poha Pl, Pukalani
$2,700,000
4 Beds ⋅ 3 Baths ⋅ 411027 MLS ⋅ Fee Simple Tenure
1973 was the year Secretariat ran the fastest Triple Crown in history, American troops came home from Vietnam, and lines at gas stations wrapped around the block. But in Kula 200, someone poured a masonry foundation on a fresh two-acre lot and built a home meant to last. When a stretch of Upcountry agricultural land was divided into two hundred two-acre parcels, it gave rise to what is known today as Kula 200, one of the most sought-after pockets along the edge of Kula and Pukalani/Makawao. Built in 1973, with a distinctive brick and masonry exterior, generously proportioned rooms, vaulted tongue-and-groove ceilings, and a wood-burning fireplace anchoring the sunken living room. Two bedrooms are en-suite, and a library/den and an extra room off primary suite create additional flexibility. Storage is abundant throughout. The setting may be the property's greatest asset. Positioned at the end of a cul-de-sac with no through traffic, the home sits privately within two fully fenced acres with a new lawn, zoned irrigation, mature landscaping, and views stretching across the valley to the West Maui Mountains, ocean, and Haleakala. Much of the interior remains original, and that's part of the opportunity. Rather than paying for someone else's renovation choices, the next owner can approach the home as a blank canvas and create an interior specific to their own taste. An enclosed sunroom and lanai take advantage of the views and Upcountry setting, while an owned photovoltaic system adds a practical update to this 1973 home. Currently tenant-occupied through May 2027, there is time to plan thoughtfully for what comes next. Two private acres, enduring craftsmanship, expansive views, and a Kula 200 location ready for its next chapter.

41 Poha Pl, Pukalani

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

1444 W Kuiaha Rd, Haiku
$2,700,000
6 Beds ⋅ 3 Baths ⋅ 408817 MLS ⋅ Fee Simple Tenure
Also listed as Multi-Dwelling Res - MLS# 408644. 7 bedrooms and both homes benefit from brand-new roofs installed in 2026, offering added confidence and peace of mind for the next owners. Owner financing with 75% down. This property is majestic and unique. One of a kind!!! Perfect for Estate Living or farming. Zoning is commercial/AG A-1 Plan for your families future. Several opportunities. Welcome to Bamboo Valley Haiku, Maui. This Maui estate, located in a hidden tropical valley and bordered by a year round flowing stream is the ultimate in privacy and seclusion. At the heart of the estate is a custom 6 bedroom, 3 bath main residence and 1 bdrm detached cottage currently operating as Bamboo Valley Inn - loved by travelers from around the world. The main home offers exceptional privacy and exquisite design elements set upon an incredible backdrop of raw natural beauty. With no homes in sight, the property captures the essence of North Shore living- peaceful, tropical, powerful and refined. 3 cozy fireplaces complement the tropical atmosphere on cool north shore nights. The expansive covered lanai has tremendous views creating an idyllic setting for outdoor dining, entertaining and relaxing. The gated entry leads to a meandering stone driveway ensuring tranquility, security and seclusion. Tucked away approximately 100 yards from the main home, and beautifully concealed behind swaying bamboo, you will discover the charming Polynesian style pole home cottage. This home is full of architectural character containing custom lava rock features throughout, wrap around lanais and an open design creating a strong indoor-outdoor Hawaiian lifestyle. Both homes contain large windows that dissolve the boundaries between indoor and outdoor, so light pours in from every direction and the tropical forest and landscape become part of the interior decor. Without ever leaving the property you can enjoy a peaceful stroll through an exotic bamboo forest on a groomed trail which leads to the year round stream. This is more than an estate - it is a tranquil retreat where nature and comfort blend seamlessly. Spacious, quiet and surrounded by beauty, this Haiku property offers a lifestyle that is increasingly hard to find in the heart of Haiku, Maui. This property is being offered fully furnished with quality, move-in ready furnishings.

1444 W Kuiaha Rd, Haiku

Listing courtesy of Nathalie Mullinix Rlty Universal Inc.

500 Bay Dr Unit 33B3-4, Lahaina
$2,695,000
2 Beds ⋅ 3 Baths ⋅ 411315 MLS ⋅ Fee Simple Tenure ⋅ Kapalua Bay Villas I BLDG.
Enjoy the beauty of Maui living at Kapalua Bay Villa 33B3, a spacious top-floor, bridge-level townhouse-style villa in the highly desirable Kapalua Bay Villas community. Ideally situated to capture beautiful Pacific Ocean views from every room, this inviting two-bedroom residence offers a wonderful blend of privacy, comfort, and the relaxed elegance of Kapalua living. The villa features an appealing combination of island-inspired style and comfortable living spaces. The generously sized primary suite serves as a peaceful retreat, featuring a king bed and spa-inspired ensuite bathroom with a Jacuzzi tub. Thoughtfully separated from the primary suite, the spacious guest bedroom offers two queen beds, providing excellent privacy and comfortable accommodations for family and friends. The open living and dining area, well-appointed kitchen, and central air conditioning complete this desirable floor plan. The gated Kapalua Bay Villas community is surrounded by lush tropical landscaping and features three beautifully maintained swimming pools with ocean views, tennis courts, and scenic walking paths. Just moments away are the beautiful beaches of Kapalua Bay, Oneloa, and Napili, along with the spectacular Kapalua Coastal Trail. Enjoy the many amenities of Kapalua Resort, including championship golf, exceptional dining, world-class snorkeling, and some of Maui's most breathtaking coastal scenery. Whether enjoying morning coffee with a view of the Pacific, exploring nearby beaches, or taking in Maui's unforgettable sunsets, Kapalua Bay Villa 33B3 offers a wonderful opportunity to own a beautiful ocean-view condominium in one of West Maui's most sought-after resort communities.

500 Bay Dr Unit 33B3-4, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

59 Wailea Gateway Pl Unit 4-201, Kihei
$2,680,000
3 Beds ⋅ 2 Baths ⋅ 410656 MLS ⋅ Fee Simple Tenure ⋅ Keala O Wailea BLDG.
Experience front-row ocean views at Keala O Wailea #4-201, a beautifully positioned 3-bedroom, 2-bathroom residence in one of the most sought-after buildings within the complex. Set on the second level, this home delivers sweeping views across the ocean to the West Maui Mountains, neighboring islands, and iconic Molokini — a panorama that rarely comes available. Unlike most properties in Wailea, this unit offers the rare luxury of your own private BBQ on the lanai, perfect for sunset dinners with an ever-changing ocean backdrop. It also comes with a private garage plus a deeded parking stall right in front of the unit — a level of convenience hard to find at this price point. Residents of Keala O Wailea enjoy resort-style amenities, including a pool, spa, outdoor clubhouse with kitchen, and fitness center overlooking the water. The pet-friendly complex sits just steps from Wailea Gateway Center's shopping and dining, and within the renowned Wailea Resort, home to three championship golf courses, tennis, pristine beaches, and world-class hotels — all moments away. Whether a full-time residence or vacation retreat #4-201 offers an unmatched combination of location, views, and lifestyle.

59 Wailea Gateway Pl Unit 4-201, Kihei

Listing courtesy of Hawaii Life (W).

1740 Piiholo Rd, Makawao
$2,649,000
5 Beds ⋅ 4 Baths ⋅ 410159 MLS ⋅ Fee Simple Tenure
Crest the rolling hills and you’ll discover this breathtaking Upcountry Maui estate: a one-of-a-kind property with a rare combination of privacy, expansive space, and timeless charm. The property lies on 4.38 acres of vibrant, open land. It could be your own little oasis, with lush landscaping and tranquility within a short driving distance to charming Makawao Town. The main residence is custom-built with rich redwood walls on both the interior and exterior, a dramatic fireplace hearth formed from black lava rock, teak bannisters, and other handcrafted architectural details throughout. The brand-new deck stretches around the home, providing glorious views of both the mountains and the North Shore. This home was built with love, and the living experience is sure to be warm and absolutely unforgettable. Beyond the primary residence, this property boasts a separate cottage with its own private entrance. This second dwelling offers exceptional flexibility for guests, extended family, or even rental potential.

1740 Piiholo Rd, Makawao

Listing courtesy of Coldwell Banker Island Prop(S).

196 Hakui Pl, Lahaina
$2,649,000
4 Beds ⋅ 4 Baths ⋅ 409052 MLS ⋅ Fee Simple Tenure
Fabulous Maui ocean, island & resort views await YOU from YOUR home at 196 Hakui Loop! Built in 1995 and extensively renovated in 2014, this two-level home offers 4BD, 3.5BA spread across 3,240 living sq. ft., plus YOUR own private pool! Enjoy dramatic sunrise/sunset ocean views from the large-picture windows of the great room and lanais off the kitchen/great room and YOUR primary bedroom – a NEW Painting Every Day! The extensive 2014 renovation included the installation of wood-look, diagonal-placed Italian porcelain tile floors (easy to maintain) and a complete redesign of the kitchen and all bathrooms. Major recent improvements included attention to home efficiency, safety & performance: 44 photovoltaic panels / 2 Telsa batteries (2020), Starlink satellite system (2023), ramp on the exterior downstairs lanai, additional hand rails at front entrance, pool, and stairwell, and shower grab bars; a new garage door opener (2022 - complete with external touchpad opener); vinyl side fencing on west side and pool entrance provide additional privacy; installation of new water heater (2024) & water descaling system (2025). The exteriors were painted in 2018. The parcel is rich with established plantings, including dwarf tropical fruit trees including lemon, lime, finger-lime, papaya, calamansi, and avocado. In 2021 the pool was remodeled resulting in wide stairs with a Baja Bench & table with port for umbrella, new plaster and new tile. Throughout, strong luxury appliance & home improvement brands exist including Sub-Zero refrigeration systems, Samsung induction range top, 2 Bosch dishwashers, KitchenAid microwave/oven combo, Jacuzzi jet-tub, Minka Aire/Regency Ceiling Fans, Lutron wall controls, two Lennox AC systems, GE, Maytag, Domus hardware & Kohler sink/toilet systems. The home is located in a quiet, less-traveled, private area of the exclusively resort community known as the Kaanapali Hillside. Kaanapali Hillside is a residential community consisting of 158 residential homes or vacant parcels (phase 1 and 2). Community amenities include a sprawling park/swing area. Monthly homeowner association dues are an incredibly reasonable $137.15 (paid quarterly). Hillside owners are minutes away from the world famous North Kaanapali beach (aka "Airport" beach) where great swimming, snorkeling and lounging is experienced! The Hillside is centrally located to downtown Lahaina and the resort community of Kapalua, plus the West Side’s public & private schools including: Kamehameha III Elementary, Hawaii Technology Academy (HTA), Sacred Hearts, and Maui Preparatory Academy—all within a 10-minute drive. Golf-carting to restaurants, work, the park, your neighbors' homes and to Kaanapali Resort is a lifestyle that most people dream about. Sold furnished with EXCEPTION. YOUR Time Is Now.

196 Hakui Pl, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

143 Leiohu Cir, Makawao
$2,641,000
3 Beds ⋅ 3 Baths ⋅ 410991 MLS ⋅ Fee Simple Tenure
Enjoy cool upcountry breezes, bicoastal views and the convenience of nearby Makawao Town in this thoughtfully upgraded ranch style residence. Situated in a gated community on a peaceful cul-de-sac, this home showcases quality upgrades and timeless finishes throughout including; cherry wood cabinetry, soft close drawers, gas cooktop, double ovens, new dishwasher and quartz countertops blending warmth and functionality. The home includes a gas fireplace, gas tankless water heater, 15 PV panels (leased, transferable to qualified buyer) and a Tesla charger delivering modern performance with island practicality. The outdoor space is equally inviting with established grapefruit, lemon and avocado trees. A beautiful home being offered furnished (with a separate bill of sale) , bring your personal touch and make 143 Lei‘ohu Circle your Maui Dream Home.

143 Leiohu Cir, Makawao

Listing courtesy of Keller Williams Realty Maui-Ki.

4955 Makena Rd Unit C302, Kihei
$2,600,000
2 Beds ⋅ 3 Baths ⋅ 411281 MLS ⋅ Fee Simple Tenure ⋅ Na Hale O Makena BLDG.
Enjoy gorgeous ocean views and the tranquility of Makena from this exceptional Na Hale O Makena C302 residence. Thoughtfully designed for comfort and relaxed island living, this well-appointed home offers two spacious bedrooms with ensuite baths, a powder room, in-unit laundry, and a large storage closet ideal for pantry use. The open floor plan features a kitchen with granite countertops, gas cooking, and high-end stainless steel appliances. An expansive living area opens to a generous lanai, complete with an outdoor grill and cooler. It's an ideal place to relax, entertain, and take in the stunning ocean views and Maui's spectacular sunsets. Ideally situated at the end of the road, Building C enjoys a peaceful and private setting. Additional amenities include elevator access, covered carport parking, and an extra storage closet. Na Hale O Makena is a private, low-density community of just 40 residences situated on over six acres of meticulously landscaped tropical grounds with an onsite resident manager. The inviting clubhouse features a saline pool, spa, and fitness room, creating a resort-like atmosphere in the comfort of home. Just minutes from some of Maui's finest beaches, dining, shopping, and premier golf courses, this Makena retreat offers the perfect opportunity to embrace all that South Maui has to offer.

4955 Makena Rd Unit C302, Kihei

Listing courtesy of Coldwell Banker Island Prop(P).

500 Bay Dr Unit 12B1-2, Lahaina
$2,600,000
2 Beds ⋅ 3 Baths ⋅ 409427 MLS ⋅ Fee Simple Tenure ⋅ Kapalua Bay Villas Ii BLDG.
Gorgeous bridge level Kapalua Bay Villa. Roll your luggage straight in the parking area. It is one of the most sought after locations in the resort. The views from this spacious, open townhome remodeled floorplan are fabulous up to Honolua Bay. Watch the whales jump from your kitchen, living and dining room. The living room lanai is the perfect spot for morning coffee or win and cheese at sunset. This condo has been lovingly remodeled by an award winning interior designer. It was professionally remodeled in 2017-2018. This is being sold turnkey. There are no steps in the upgraded bathrooms. Gorgeous tile with glass waterfall accents, rainfall and handheld shower heads. The downstairs master has a beautiful soaking tub, a true spa bath. Open and decorative tile designs. The upstairs master suite has a beautiful master bath with washer-dryer, etched windows frosted for privacy and beautiful shades throughout for privacy. The bathroom sinks are all spun glass basins. Ample closet space. The doors are mahagony. The flooring throughout the entire condo is large format limestone. The kitchen has sapele wood slab cabinets with a lighted glassware cabinet. Countertops are taj mahal. Kitchen appliances include kitchen aid oven and microwave. Bosch stovetop and dishwasher. The light switches have been upgraded to Legrand Adorne in designer colors for a clean modern look. The sliders to the lanai and the air conditioners are recent additions to this high level home. The soaring ceilings in the "great room" add to the light and spaciousness of the living area. The stairwell is bamboo flooring. The gorgeous artwork is included with the original art and prints throughout by native and local artists. The Kapalua Resort is home to award winning restaurants, golf, and tennis/pickleball. Great resort community. World class beaches. The Bay villas have tennis courts, gated, three swimming pools.

500 Bay Dr Unit 12B1-2, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

3435 Hookipa Pl Unit B, Kihei
$2,599,000
5 Beds ⋅ 4 Baths ⋅ 410070 MLS ⋅ Fee Simple Tenure
Experience breathtaking panoramic ocean views from this stunning unit B of a 3 units CPR, newly remodeled 2-story home offering 3,064 sq ft of modern coastal living. The open floor plan, with soaring vaulted ceilings, creates a bright, spacious ambiance that's ideal for relaxing or entertaining, connecting the kitchen to the dining and living areas, which flow seamlessly to the private wrap-around lanai. With 5 bedrooms and 4 bathrooms, there's ample space for guests and a home office. The flexible layout includes the possibility of a split unit downstairs, which could be accessible via an interior staircase or a separate outside entrance, perfect for multi-generational living, guest quarters, or long-term rental potential. Don't miss your chance to own this exceptional property that combines luxury, versatility, and spectacular views! This beautiful home is perched at the top of the prestigious Maui Meadows neighborhood, just minutes from the beach, world-class restaurants, golf courses, and everything that South Maui has to offer. This is a Residential CPR.

3435 Hookipa Pl Unit B, Kihei

Listing courtesy of Equity One Real Estate Inc (M).

110 Kaanapali Shores Pl Unit 1019, Lahaina
$2,599,000
2 Beds ⋅ 2 Baths ⋅ 409874 MLS ⋅ Fee Simple Tenure ⋅ Mahana BLDG.
VIEWS VIEWS VIEWS! Rarely does one of the best beach front properties become available…until NOW! Located on the tenth floor of the Lanai building (aka South Building), Mahana 1019 is a corner-coastline, direct beachfront 2-bedroom and 2-bathroom condominium located on the world-famous white sand beaches of Kaanapali North Beach. With tropical Asian influenced décor, custom materials & premium appointments, this estate embodies the true spirit of island living! Sold furnished. The Mahana of Kaanapali is a beachfront high-riser condominium community that consists of 216 units across two 12-floor buildings. Zoned HOTEL, the property is permitted to conduct transient vacation rentals. The community includes pool, spa and BBQ amenities. YOUR Time is Now.

110 Kaanapali Shores Pl Unit 1019, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

130 Kai Malina Pkwy Unit NR609, Lahaina
$2,590,000
2 Beds ⋅ 2 Baths ⋅ 406602 MLS ⋅ Fee Simple Tenure ⋅ Honua Kai - Konea BLDG.
Honua Kai - Konea NR609 is a 2 bed / 2 bath ocean-view residence with an expansive interior courtyard. Set well above the palm trees that grace the grounds and beachside pools below, it enjoys a commanding vista of the Pacific. With the lanai's glass nano walls wide open, the indoor / outdoor living space blends to a total of 1545 sq.ft. Sunsets and whale watching abound from the comforts of home. It is beautifully appointed and offered fully furnished with top-end touches throughout, such as granite countertops and Bosch appliances. Honua Kai Resort boasts 3 spectacular pools, Dukes Restaurant, a full service spa, gym, beachside grills, hot tubs, and of course, Ka’anapali Beach with some of the best snorkeling on Maui. Konea NR609 is in one of Maui's most sought after resorts with an impressive rental history. Your piece of paradise awaits.

130 Kai Malina Pkwy Unit NR609, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

86 Poailani Pl Unit 32, Kihei
$2,575,000
4 Beds ⋅ 5 Baths ⋅ 411148 MLS ⋅ Fee Simple Tenure ⋅ Kanani Wailea BLDG.
Also listed as single family home MLS#411149. Experience effortless Wailea living in this beautifully appointed 4-bedroom, 4.5-bath single-level ocean-view residence in Kanani Wailea. Offering 2,175 sq. ft. of thoughtfully designed living space, the home enjoys beautiful ocean views and spectacular Maui sunsets. The well-appointed kitchen features a Sub-Zero refrigerator and wine cooler, along with Wolf cooktop, oven, and microwave. Sold fully furnished and move-in ready, each bedroom features its own en-suite bath. Recent updates include new flooring throughout and a beautifully remodeled primary bath. A secure private courtyard welcomes you and provides separate access to the 3-bedroom, 3.5-bath main residence and the attached guest suite, offering added privacy and a comfortable retreat for family and friends. Ideally located near Wailea's world-class beaches, championship golf, luxury resorts, shopping, and dining, this exceptional residence offers a wonderful combination of ocean views, privacy, and relaxed Maui luxury.

86 Poailani Pl Unit 32, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

86 Poailani Pl Unit Unit 32, Kihei
$2,575,000
4 Beds ⋅ 5 Baths ⋅ 411149 MLS ⋅ Fee Simple Tenure
Also listed as condominium MLS# 411148. Experience effortless Wailea living in this beautifully appointed 4-bedroom. 4,5-bath single-level ocean-view residence in Kanani Wailea. Offering 2,175 sq. ft. of thoughtfully designed living space, the home enjoys beautiful ocean views and spectacular Maui sunsets. The well-appointed kitchen features a Sub-Zero refrigerator and wine cooler, along with Wolf cooktop, oven, and microwave. Sold fully furnished and move-in ready, each bedroom features its own en-suite bath. Recent updates include new flooring throughout and a beautifully remodeled primary bath. A secure private courtyard welcomes you and provides separate access to the 3-bedroom, 3.5-bath main residence and the attached guest suite, offering added privacy and a comfortable retreat for family and friends. Enjoy the convenience of a lock and leave condominium in a single family home. Ideally located near Wailea's world-class beaches, championship golf, luxury resorts, shopping, and dining, this exceptional residence offers a wonderful combination of ocean views, privacy, and relaxed Maui luxury. This is a Residential Condo.

86 Poailani Pl Unit Unit 32, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

100 Poailani Pl Unit 29, Kihei
$2,550,000
4 Beds ⋅ 4 Baths ⋅ 409490 MLS ⋅ Fee Simple Tenure
Also listed as Condo MLS# 409467. In the best location in Kanani Wailea, adjacent to expansive open space and unobstructed ocean views, this exceptional single-level residence offers the community’s most desirable floor plan. Located in an exclusive gated enclave of just 38 detached residential condominiums, this beautifully appointed 4-bedroom, 4-bath home blends luxury, privacy, and effortless island living. The 2,129 sq. ft. interior features an open-concept design filled with natural light and quality finishes like Hunter Douglas interior blinds and remote exterior blinds. The recently remodeled kitchen features top-of-the-line appliances like Wolf and Sub-Zero. Modern upgrades include the latest Wi-Fi system, a multi-zone Sonos sound system throughout, and a security system for added convenience and peace of mind. Two true primary suites offer spacious walk-in closets and large double-vanity baths, each remodeled with Toto Washlets. A third bedroom is located in the main living area with a full bath just across the hall, while the fourth bedroom and bath are privately situated off the courtyard—ideal for guests or extended family. Offered fully furnished and turn-key, the home includes a complete inventory of housewares and essentials, making it ready for immediate enjoyment or effortless second-home ownership. Lovely ocean views with dreamy sunsets from your large, private lanai, and the ease of lock-and-leave ownership make this home especially appealing. Association-maintained landscaping enhances the carefree lifestyle. Kanani Wailea amenities include a heated infinity-edge pool, spa, fitness room, and cabana with full kitchen. Just minutes from Wailea’s world-class beaches, golf, dining, and shopping, this is a rare opportunity to own in one of South Maui’s most coveted communities.

100 Poailani Pl Unit 29, Kihei

Listing courtesy of McEntire Realty.

100 Poailani Pl Unit 29, Kihei
$2,550,000
4 Beds ⋅ 4 Baths ⋅ 409467 MLS ⋅ Fee Simple Tenure ⋅ Kanani Wailea BLDG.
Also listed as Residential MLS# 409490. In the best location in Kanani Wailea, adjacent to expansive open space and unobstructed ocean views, this exceptional single-level residence offers the community’s most desirable floor plan. Located in an exclusive gated enclave of just 38 detached residential condominiums, this beautifully appointed 4-bedroom, 4-bath home blends luxury, privacy, and effortless island living. The 2,129 sq. ft. interior features an open-concept design filled with natural light and quality finishes like Hunter Douglas interior blinds and remote exterior blinds. The recently remodeled kitchen features top-of-the-line appliances like Wolf and Sub-Zero. Modern upgrades include the latest Wi-Fi system, a multi-zone Sonos sound system throughout, and a security system for added convenience and peace of mind. Two true primary suites offer spacious walk-in closets and large double-vanity baths, each remodeled with Toto Washlets. A third bedroom is located in the main living area with a full bath just across the hall, while the fourth bedroom and bath are privately situated off the courtyard—ideal for guests or extended family. Offered fully furnished and turn-key, the home includes a complete inventory of housewares and essentials, making it ready for immediate enjoyment or effortless second-home ownership. Lovely ocean views with dreamy sunsets from your large, private lanai, and the ease of lock-and-leave ownership make this home especially appealing. Association-maintained landscaping enhances the carefree lifestyle. Kanani Wailea amenities include a heated infinity-edge pool, spa, fitness room, and cabana with full kitchen. Just minutes from Wailea’s world-class beaches, golf, dining, and shopping, this is a rare opportunity to own in one of South Maui’s most coveted communities.

100 Poailani Pl Unit 29, Kihei

Listing courtesy of McEntire Realty.

100 Ridge Rd Unit 1723 24, Lahaina
$2,550,000
3 Beds ⋅ 3 Baths ⋅ 408836 MLS ⋅ Fee Simple Tenure ⋅ Kapalua Ridge BLDG.
Perched at the top of The Ridge at Kapalua, this 3-bedroom unit offers the ultimate combination of stunning ocean views, luxurious space, and modern decor. Remodeled in 2016/2017, this unit has been primarily used as a second home, but it is also a highly sought-after short-term rental unit, due to limited comparable inventory. This unit feels more like a home than a condo. Its features include a large living room, a kitchen with a separate dining area, 2 full ensuites with large bathrooms and closets, a flexible room that may be used as a third bedroom or an office, a full-size guest bathroom and additional enclosed lanai spaces. The Ridge at Kapalua is a low-density resort, featuring 2 pools with cabanas, lounging and dining areas. The property is meticulously maintained by the onsite manager. Kapalua Resort offers easy access to four of the most well-known beaches in Hawaii and world class restaurants and spas. Tennis courts, pickleball courts, cardio hiking, as well as leisurely strolling routes are available for those that want to stay active on land.

100 Ridge Rd Unit 1723 24, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

130 Kai Malina Pkwy Unit SR836, Lahaina
$2,545,000
2 Beds ⋅ 2 Baths ⋅ 410793 MLS ⋅ Fee Simple Tenure ⋅ Honua Kai - Hoku Lani BLDG.
Back On Market! Experience the perfect blend of luxury, comfort, and investment potential at Hokulani 836, a premier 2-bedroom, 2-bath, 1,240 sq. ft. corner unit in the renowned Honua Kai Resort in Maui, Hawaii. Perched on the 8th floor, this condo features an oversized lanai offering breathtaking ocean views—stretching from the Island of Moloka'i to the majestic West Maui Mountains. The lanai is the perfect spot to savor Maui’s spectacular sunsets, watch whales, or enjoy a quiet morning coffee before starting your island adventures. Hokulani 836 blends island living with modern elegance. The primary bedroom features a king bed and ensuite bathroom with a full-size shower, tub, and dual sinks. The second bedroom is versatile, offering either a king bed or two twins, and also includes a bathroom with the same luxurious features. Upgraded ceramic tile floors throughout elevate the space, while high-end furnishings, including a memory foam sleeper sofa, provide comfort for up to six guests. A fully equipped kitchen with granite countertops and full-size appliances, in-suite laundry, and an owners’ closet make this unit as functional as it is beautiful. You’ll enjoy the convenience of self-controlled air conditioning, ensuring your comfort no matter the season. The bi-fold doors seamlessly connect the living space to the oversized lanai, creating a true indoor-outdoor experience that captures Maui’s natural charm. This unit is turnkey and rental-ready, with a proven track record of strong short-term rental income. Its prime location, luxurious features, and world-class amenities make it highly appealing to vacationers, ensuring consistent demand and revenue. Ownership at Honua Kai Resort grants access to seven swimming pools, a waterslide, a 24-hour fitness center, and on-site conveniences like Duke’s Restaurant and Whalers General Store. The beachfront boardwalk offers serene oceanfront strolls, rounding out a resort experience with everything you need for relaxation and adventure. Whether you’re seeking a profitable investment property or a personal Maui retreat, Hokulani 836 offers the best of both worlds. This is your chance to own a home away from home that also serves as a money-making asset when you’re away. Claim your piece of paradise—Hokulani 836 is waiting for you.

130 Kai Malina Pkwy Unit SR836, Lahaina

Listing courtesy of Maui Westside Properties.

2040 Kauhikoa Rd, Haiku
$2,500,000
5 Beds ⋅ 4 Baths ⋅ 411312 MLS ⋅ Fee Simple Tenure
For more information, see the duplicate listing at Multi Dwelling listing MLS #411313. Country living at its finest on 2 acres in Upcountry Maui, with sweeping views across green pastures and Giggle Hill and beyond to the ocean and Kahului Bay. The main home features high ceilings, wraparound windows, skylights, and a lovely deck where you can take in the tranquil views. Two additional homes, each with its own character and charm, also offer lovely views and have new roofs and new septic systems. Most of the kitchens on the property have been renovated. The houses and garage are currently set up as follows: Main House: a 3bed/2bath, 2/1 and 0/1. Garage: 2/1. Unit A (middle house): 3/1 and 2/1. Unit B (lower house): 3/2 and 1/1. A total of 8 units of which 7 bring in $12,500 a month in rental income. The grounds are a gardener's delight: about 10 avocado trees, several banana patches, lemon and lime trees, and abundant hibiscus and boganvilla, with tenants currently growing vegetables and herbs. Cooling trade winds in summer and plentiful rainfall keep the land lush. There's no irrigation system, and the water bill runs about $160 a month. An easy 6 minutes to Makawao or Haiku and just 10 minutes to Hookipa. Move into the main house and have the tenants and income already in place. Most tenants are on a Month toMonth lease. Or the property offers flexibility for a family compound or multigenerational living. Showings:  Two units are shown at the first showing; all units at a second showing with 48 hours' notice. Buyers to do their due diligence as regards property permits and use. Contact your favorite REALTOR®.

2040 Kauhikoa Rd, Haiku

Listing courtesy of Keller Williams Realty Maui-Ka.

3275 Kehala Dr Unit 3275 Kehala Drive, Kihei
$2,500,000
5 Beds ⋅ 5 Baths ⋅ 410912 MLS ⋅ Fee Simple Tenure
Nestled in the highly coveted Maui Meadows neighborhood, 3275 Kehala Drive delivers breathtaking, panoramic ocean views from every single lanai. The main residence boasts a light, airy open-concept floor plan, anchored by a recently remodeled gourmet kitchen. Chefs will love the premium stainless steel gas stove, high-end appliances (including a dedicated ice machine), and striking Labradorite countertops imported directly from Madagascar. The flexible four-bedroom layout features an upstairs primary suite, a private downstairs mother-in-law suite, two additional versatile bedrooms, and a laundry room. Outside, the low-maintenance backyard serves as an island oasis, including a barbecue, storage shed, and a mature, fruit-bearing mango tree. Offering excellent rental income potential, the property includes a detached 1-bedroom, 1-bathroom Ohana unit. Enjoy ultimate peace of mind with a home that has been freshly painted and tented (2026).

3275 Kehala Dr Unit 3275 Kehala Drive, Kihei

Listing courtesy of Berkshire Hathaway Maui Prop-L.

321 Puumakani Pl, Kahului
$2,500,000
9 Beds ⋅ 7 Baths ⋅ 410778 MLS ⋅ Fee Simple Tenure
Rare Kahului opportunity offering 4,570 sq. ft. of versatile living space with 9 bedrooms and 6.5 bathrooms! Perfect for multigenerational living or hosting extended guests, this expansive two-story residence features TWO PRIMARY SUITES—one on the main level for convenient single-level living and one upstairs for added privacy. The property also presents potential rental and income-producing opportunities, including the possibility for care home or assisted-living use. The heart of the home boasts soaring ceilings, elegant travertine flooring, and a spacious chef's kitchen with quartz countertops. Stay comfortable year-round with brand-new split A/C systems in living/dining areas and most bedrooms. Outdoor living shines with a covered downstairs lanai and a huge upstairs deck. Includes accessible roll-in showers and flexible layout options. Exceptional space, comfort, and potential in central Kahului! Easy to show.

321 Puumakani Pl, Kahului

Listing courtesy of Realty 1st Inc.

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