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$4,950,000
5 Beds ⋅ 5 Baths ⋅ 202606798 MLS
Oceanfront residence on one of Oahu's most beautiful stretches of coastline. 5811 Kalanianaole Highway is a contemporary oceanfront residence where the remodel and the setting work together. Thoughtfully remodeled with a contemporary design sensibility, every detail has been considered and every space elevated. The open plan kitchen anchors the main living area with a large island, upgraded appliances, and a flow that makes it as comfortable for quiet mornings as it is for entertaining. Generous lanai space leads to the lawn and the ocean beyond. Morning coffee with the sunrise over the Pacific, afternoon barbecues on the lawn with the water right in front of you. The second-floor primary suite is designed to maximize the setting. Ocean and mountain views from the primary bedroom, ocean views from the bath, and a dedicated space that works equally well as a home office or art studio, all facing the water. Five bedrooms, four full baths, and a half bath across 3,300 square feet of living on 8,674 square feet of fee simple land. The first floor includes a full bedroom suite. A pool provides a private retreat in back. Two-car garage. Photovoltaic owned. Direct ocean access.

5811 Kalanianaole Highway, Honolulu
$4,950,000
2 Beds ⋅ 2 Baths ⋅ 729851 MLS
Steps to the sand - low priced in Hanalei. This is a fixer upper ready for you to put your personal stamp on your own piece of Hanalei. The location on the corner of Weke Road and Hee Road can't be beat. A 60 second stroll puts your feet on the sandy shore of Hanalei Bay. Experience world class surfing in the winter, gentle boogie-board combers in the summer. Need groceries, looking for dinner out? Three blocks away brings you into Hanalei town. Hanalei is the place to be. Don't miss this opportunity. Property sold AS IS, WHERE IS. All offers must include an AS IS Addendum. Sellers reserve the right to structure this sale as a 1031 Tax Deferred Exchange, at no cost to the buyer. Price is set to attract offers.

5404 Weke Rd, PRINCEVILLE
$4,950,000
3 Beds ⋅ 3 Baths ⋅ 408178 MLS
Breathtaking panoramic ocean views greet you the moment you step through the doors of 232 Crestview Road, located within the highly sought-after, gated community of Pineapple Hill Estates at Kapalua. This luxurious single-level residence spans 3,354 square feet of interior living space and is set on a large half acre lot. The property is ideally positioned at the end of a quiet cul-de-sac, nestled between two vacant lots offering exceptional privacy and the potential for further expansion. The home features three bedrooms and three bathrooms plus a bonus room adjacent to the 2 car garage, with thoughtfully designed living spaces that open seamlessly to spacious lanais. Highlights include a designer walk-in closet in the primary suite, a Jacuzzi soaking tub, state-of-the-art appliances, Ubatuba granite countertops, cherry wood cabinetry, a fireplace, ceramic Moro Italian wood like floor tiles and elegant finishes. Outdoor pleasures include a large lap pool and spa adorned with luxurious Monier tile imported from Switzerland, creating a true resort-style experience. Recent improvements include a upgraded AC and Lutron Smart home system installed in 2025. Ownership in Pineapple Hill Estates provides access to premier amenities including a private clubhouse, swimming pool, tennis courts, and pickleball courts. The surrounding Kapalua resort area is home to the world-famous Plantation golf course, scenic hiking trails, and renowned five-star resorts such as Montage Kapalua Bay and The Ritz-Carlton. A variety of acclaimed restaurants offer both local flavors and world-class dining experiences. Offered fully furnished, this exceptional home presents a rare opportunity to own a private piece of paradise—ready for your personal touch and perfectly suited for embracing the refined elegance of luxury island living.

232 Crestview Rd, Lahaina
$4,950,000
4 Beds ⋅ 2 Baths ⋅ 408089 MLS
Rare opportunity to own one or two contiguous beachfront homes on one of South Maui's favorite beaches. Consolidation of the lots located at 1606 and 1598 Halama Street would create an estate site of over 32,000 square feet. The property is being sold for land value only. The main home and ohana are currently rented to long term tenants. The structures are being sold in "As Is" Condition.

1606 Halama St, Kihei
$4,950,000
3 Beds ⋅ 3 Baths ⋅ 408090 MLS
Rare opportunity to own one or two contiguous beachfront homes on one of South Maui's favorite beaches. Consolidation of the lots located at 1598 and 1606 Halama Street would create an estate site of over 32,000 square feet. The property is being sold for land value only. The main home and ohana are currently rented to long term tenants. The structures are being sold in "As Is" Condition.

1598 Halama St, Kihei
$4,950,000
3 Beds ⋅ 3 Baths ⋅ 725861 MLS
One of the best locations in Hanalei. Set in the quiet, cul-de-sac at the end of coveted Weke Road, this well maintained, clean and simple family home at 5527 Weke Road is located just steps from the iconic crescent beach of Hanalei Bay. Across two levels, this peaceful 3 bedroom, 2 bathroom home also offers open living areas for relaxing or entertaining and sits surrounded by lush mountains and pristine waterfalls. With its proximity to Hanalei town center, as well as the beach and waves of Hanalei Bay, this is a true Hanalei lifestyle property. Known for its stunning natural beauty, laid-back atmosphere, and vibrant cultural scene, Hanalei offers a lifestyle that's hard to find anywhere else. In addition to its outdoor attractions, Hanalei is home to a thriving arts and culture community. The town has a number of galleries and boutique shops showcasing the work of local artists, as well as a weekly farmers' market throughout the year. Outdoor pursuits, including swimming, kayaking, surfing, hiking and snorkeling, are all conveniently accessible and world class golf and tennis facilities are located just ten minutes away in Princeville. This is a rare opportunity to own a home in one of the most prized locations on Kauai.

5527 Weke Rd, HANALEI
$4,925,000
3 Beds ⋅ 4 Baths ⋅ 730765 MLS ⋅ Kukui`Ula BLDG.
Tucked beneath the tree-lined drive leading to The Club at Kukuiʻula, Club Cottage 12B offers a relaxed island retreat just steps from the community’s private amenities. Owners and guests can easily stroll next door to dine, work out, enjoy spa treatments, play golf, or spend the afternoon by the pool, making everyday life effortlessly connected to the heart of The Club. Designed in the spirit of Kaua‘i’s plantation architecture, the cottage embraces indoor and outdoor living with spacious lānai, private front and back yards, and lush tropical plantings surrounding a lava rock fire pit. The home includes two primary suites with large built-in closets and spa-inspired bathrooms featuring dual sinks, pedestal tubs, and interior showers that open to outdoor lava rock garden showers. A separate one-bedroom guest cottage offers additional privacy for visiting friends and family. Inside, dark ipe flooring and black honed granite kitchen countertops complement a thoughtfully designed interior. The kitchen is equipped with GE Monogram appliances, including a refrigerator, range, and double-drawer dishwasher. Professionally designed furnishings, linens, artwork, accessories, and electronics are included, creating a fully furnished home that is ready to enjoy from the moment you arrive. Club Cottage 12B offers 2,642 square feet of total living space, including 1,983 square feet of air-conditioned interiors and 659 square feet of lānai living. Designed for LEED for Homes certification, this residence brings together comfort, craftsmanship, and the easy rhythm of life at Kukuiʻula on Kaua‘i’s sunny south shore in Poipu. Kukui`ula Ownership Amenities Include: Tom Weiskopf-designed, Private 18-hole Par-72 golf course, World-class spa, outdoor lap pool, steam rooms, and complete fitness rooms and movement studios Access to Upcountry Farm and Catch n' Release Fishing Lake Volleyball, pickleball, horseshoes, Pool Bar and Grille, and much more

2833 Ke Alaula Street Unit 12b, KOLOA
$4,925,000
7 Beds ⋅ 7 Baths ⋅ 202610108 MLS
The most extraordinary remodel transformation you’ll ever see! This stunning 7 bedroom, 6.5 bath residence spans over 6,000 square feet on a generous 14,125-square-foot lot, just a short stroll from Kailua’s iconic 3 mile sandy beach. Completely reimagined, the home feels brand new, fresh, modern, and thoughtfully designed for today’s island lifestyle. Two expansive primary suites anchor the home, each featuring spa-level amenities with private saunas, oversized walk-in showers, washer/dryer's and luxurious soaking tubs. A large rumpus room offers the perfect retreat for the little’s or additional entertaining, while the yard is surrounded by new areka palms that will give total privacy in the near future and a prized mango tree. Plenty of room for a pool too. The kitchen is a showpiece, centered around a 14-foot quartzite island, complemented by striking windows, doors, stone flooring, and two architectural staircases. A rare 2,000-square-foot rooftop deck delivers flexibility for entertaining or relaxing under the stars. Additional highlights include an au-pair suite with kitchenette, a stunning porte-cochère, and an unbeatable location close to the heart of Kailua.

125 N Kalaheo Avenue, Kailua
$4,900,000
3 Beds ⋅ 4 Baths ⋅ 723034 MLS
Club Cottage #11 within Kukuiula consists of a serene and architecturally significant 2-bedroom 2.5 bath residence and a complementing 1-bedroom 1 bath detached guest house. Located adjacent to The Club at Kukuiula, this property affords the exclusive opportunity to join the exclusive Lodge Program at Kukuiula where you and your vacationing guests may enjoy coveted access to the Club at Kukuiula and its amenities. This Club Cottage Property provides fine features Including: Conditioned Living: 2,048 SF Living Lanai: 660 SF Land Area: 13,522 SF Two Primary Suites with Large Built-in Closets Two Bathrooms with Dual Sinks, Tub and Interior & Shower Garden Showers One Bedroom – One Bath Guest Cottage Oversized covered lanai spaces Dark Ipe Flooring Black Honed Granite Kitchen Countertops GE Monogram Series & SubZero Kitchen Appliances Professionally Designed Furnishings Included Private Front and Backyards Lush Tropical Native Plantings Lava Rock Fire Pit Kukuiula Ownership Privileges and Amenities Include: Private Club Membership Tom Weiskopf-designed, Private 18-hole Par-72 golf course that was named, "Best New Private Golf Course 2011" by Golf Magazine World-class spa featuring indoor/outdoor treatment rooms, outdoor lap pool, steam rooms, and complete fitness rooms and movement studios Golf Club House Fine dining in the Kukuiula Plantation House Design Guidelines Comprehensive paths and hiking trails throughout the Community Roving 24/7 Security Services Access to Upcountry Farm and Lake Fitness and Spa Programs Volleyball, Pickleball, Tennis, Pool Bar and Grille Club Membership Initiation Fee of $150,000.00 payable at closing by Buyer

2815 Ke Alaula Street, KOLOA
$4,900,000
3 Beds ⋅ 4 Baths ⋅ 202519051 MLS
Club Cottage #11 within Kukuiula consists of a serene and architecturally significant 2-bedroom/2.5-bath residence and a complementing 1 bedroom 1 bath detached guest house. Located adjacent to The Club at Kukuiula, this property affords the exclusive opportunity to join the exclusive Lodge Program at Kukuiula where you and your vacationing guests may enjoy coveted access to the Club at Kukuiula and its amenities.This Club Cottage Property provides fine features including: 2 Primary Suites, a Separate, Detached 1-bdrm Cottage, Professionally Designed Furnishings, Private Front and Backyards, Lush Tropical Native Plantings, and Lava Rock Fire Pit. Amenities Include: Private Club Membership, Tom Weiskopf-designed, Private 18-hole Par-72 golf course, World-class spa featuring indoor/outdoor treatment rooms, outdoor lap pool, steam rooms, and complete fitness rooms and movement studios, Golf Club House, Fine dining in the Kukuiula Plantation House, Design Guidelines, Comprehensive paths and hiking trails throughout the Community, Roving 24/7 Security Services, Access to Upcountry Farm and Lake, Fitness and Spa Programs, Volleyball, Pickleball, Tennis, Pool Bar and Grille.

2815 Ke Alaula Street, Koloa
$4,895,000
3 Beds ⋅ 4 Baths ⋅ 732411 MLS
One owner. Never rented. Located within Kukuiʻula's federally designated Opportunity Zone. Buyers should consult their tax advisor regarding eligibility and potential benefits. Ideally situated on one of Kukuiʻula's most desirable streets, this single level residence offers convenient access by foot or golf cart to The Club at Kukuiʻula, the Tom Weiskopf award winning golf course, and the Shops at Kukuiʻula. Direct golf cart access connects to Kukuiʻula's landscaped greenbelt, ponds, waterfalls, and pathways throughout the community. The 3 bedroom, 3.5 bathroom home offers approximately 2,760 sqft of interior living space on a 13,553 sqft homesite, larger than many in the Kaulu neighborhood. Property Features: ° 16 foot wall of Afromosia framed pocketing glass and screened doors that tuck completely away for seamless indoor outdoor living ° Plantation inspired architecture with ensuite baths & private outdoor garden showers ° Zoned for vacation rental (VDA) ° Custom Afromosia cabinetry ° Taj Mahal quartzite countertops ° Premium appliances ° Walk in pantry with dedicated climate control ° Primary suite with cedar lined walk in closet ° Standing height semi finished attic with angled pull down ladder and handrail ° Private pool, covered pavilion, and built in BBQ ° Central AC, whole house water filtration, instant and solar hot water, and 18 owned - photovoltaic panels ° Oversized garage with third bay, plumbing and electrical roughed in for future flexibility, subject to County and Kukuiʻula approval A rare opportunity to own a meticulously maintained Kukuiʻula residence combining thoughtful island architecture, privacy, and an unmatched Kauaʻi lifestyle.

5015 Lau Nahele St, KOLOA
$4,895,000
4 Beds ⋅ 6 Baths ⋅ 409534 MLS
Located within the coveted acreage community of Wailuku Country Estates, 2150 Kamaile Street offers a rare combination of privacy, scale, and resort-style living across approximately 2.78 acres. The main residence spans approximately 3,175 square feet and is designed to capture the essence of indoor-outdoor island living. Generous living spaces flow effortlessly to the surrounding grounds, creating an inviting setting for both everyday comfort and elevated entertaining. A detached two-bedroom, two-bathroom Ohana of approximately 1,000 square feet enhances the compound feel of the property. Complete with an oversized garage, this separate residence offers privacy and versatility while remaining integrated into the overall estate design. Recent enhancements have transformed the outdoor experience into a private retreat. A newly constructed resort-style pool and spa anchor the property’s recreational amenities, complemented by an expanded pool deck ideal for gatherings. A tranquil water feature and private putting green further elevate the grounds, creating a curated setting designed for relaxation and enjoyment. The detached barn structure has been thoughtfully upgraded and finished, adding substantial flexibility to the estate. Whether utilized as a studio, gym, office, creative space, or extended entertaining area, it contributes meaningful utility and enhances the property’s overall functionality. With nearly three acres of usable land, multiple structures, and newly added resort-level amenities, 2150 Kamaile Street presents a compelling opportunity to own a private lifestyle compound in one of Central Maui’s most desirable estate communities. This is a property designed not only as a residence — but as a destination.

2150 Kamaile St, Wailuku
$4,800,000
4 Beds ⋅ 4 Baths ⋅ 732592 MLS ⋅ Nob Hill I BLDG.
Positioned at one of the highest elevations in Waimea, this exceptional property captures sweeping panoramic views of Mauna Kea, Mauna Loa, Hualālai, the Kohala coastline, the Pacific Ocean, and Waimea's rolling green pastures. Set on a generous 19,950 sq. ft. lot along one of Waimea's most desirable streets, the residence offers approximately 3,365 sq. ft. of living space, including a newly constructed detached two-car garage with a private one-bedroom, one-bath guest apartment above. Originally built in 1993, this exceptional residence has been luxuriously renovated and thoughtfully upgraded throughout by the current owner. The home seamlessly blends timeless character with refined contemporary finishes and thoughtful upgrades throughout. The flexible floor plan offers generous living spaces that can accommodate extended family, guests, a home office, gym, or income-producing opportunities. Glass-enclosed lanais on both levels frame the extraordinary mountain and ocean vistas while creating comfortable year-round indoor-outdoor living in Waimea's ideal climate. Ideally located just minutes from the heart of Waimea, the property enjoys convenient access to acclaimed private schools, restaurants, shopping, medical services, and cultural attractions. The world-renowned beaches, championship golf courses, and luxury resorts of the Kohala Coast are only a short drive away. Combining exceptional craftsmanship, remarkable views, generous living spaces, and one of Waimea's premier locations, this is a rare opportunity to own one of the area's finest luxury residences.

65-1347 Konokohau Rd, KAMUELA
$4,800,000
4 Beds ⋅ 3 Baths ⋅ 202614040 MLS
Nestled on the prestigious Diamond Head neighborhood, offers a large 15,000 sqft lot overlooking Kahala with ocean views. Bring your architect and contractor to design your home. Conveniently located near Kapiolani Park, Diamond Head, Kahala Mall, beaches, and Waikiki, making it an exceptional place to enjoy both tranquility and island living at its best.

633 Hakaka Place, Honolulu
$4,800,000
4 Beds ⋅ 5 Baths ⋅ 202604988 MLS
Welcome to paradise living at 84-1000 Maiola St in the private gated community of Mauna 'Olu in Makaha Valley on the Leeward coast of Oahu! This hillside estate boasts panoramic ocean views of Makaha Beach and the Waianae mountain range. Newly built in 2007 and renovated in 2025 including brand new travertine flooring, kitchen cabinets, granite countertops, stainless steel appliances, fresh paint, tropical landscaping, hand carved wood details, and an attached ohana dwelling with separate entrance for private hospitality or visitors. Resort like amenities include an infinity edge salt water pool with waterfall, outdoor putting green, full-size tennis court, outdoor bar, traditional imu, gas grills, fire pit, and a detached 1,800 sqft 2-story garage with elevator perfect for a workshop, studio, or extra storage. The spacious open-concept layout is perfect for entertaining or relaxing in this peaceful and private setting. Enjoy the beautiful Hawaiian sunsets from the large lanai, bring your golf clubs to Makaha Valley Country Club, or take a short stroll to the beach for a swim. Don't miss this rare opportunity to own your piece of paradise with this private Makaha estate!

84-1000 Maiola Street, Waianae
$4,800,000
5 Beds ⋅ 7 Baths ⋅ 202528272 MLS
Perched on the eastern facing perimeter of the prestigious Hawai’i Loa Ridge, 875 Ikena Circle brings a unique grandness to Oahu. Enjoy picturesque views of the Pacific Ocean, Hawai’i Kai Marina, Koko Head, and Portlock. A multi level layout provides the ideal recipe for entertainment and multigenerational living. The main level of the home showcases vaulted ceilings and an abundance of natural light. A spacious primary bedroom suite is situated on the main level adjacent to the living room. Make your way downstairs where you are presented with 3 suites along with an additional living room that opens to the pool deck. A detached pool house provides a personal sanctuary that can be utilized as a home office, a space for guests, or a cozy man cave. Amenities within the community include: Gated entry, 24/7 security, tennis & pickleball.

875 Ikena Circle, Honolulu
$4,795,000
3 Beds ⋅ 4 Baths ⋅ 408559 MLS
3943 Wailea Ekolu is one of Wailea Golf Estates' most distinctive ocean-view Residences, offering Panoramic Ocean, Outer-Island & Mountain Views, Estate-Scale Living, Timeless Architectural Character, and a Premier Golf-Frontage Setting. Encompassing approximately 4,355 square feet, this expansive residence features 3 bedrooms, an office/den, 4 full bathrooms, a spacious great room, and an additional living room that opens seamlessly to the pool and outdoor entertaining area. Designed with enduring craftsmanship, generous proportions, and a grand sense of arrival, the home showcases architectural details rarely found in today's newer luxury residences. From the moment you enter, arched mahogany-and-glass entry doors accented with African Wenge welcome you into a dramatic curved vestibule, where rounded plaster walls, rich mahogany millwork, and a grand staircase immediately reveal the craftsmanship and architectural character that define this remarkable home. Two en-suite bedrooms located on the ground floor each enjoys its own outdoor space—ideal should you want to have SINGLE FLOOR-PLAN LIVING. Upstairs, a PRIVATE SANCTUARY awaits: the approx. 1,581 sq. ft. primary bedroom suite and den offer exceptional PRIVACY and unparalleled OCEAN AND OUTER ISLAND VIEWS WITH WRAP AROUND LANAIS, along with impressive Haleakala vistas that shift beautifully with the light. The generous kitchen opens to a bright great room with SLIDING WALLS OF GLASS on two sides—inviting lovely cross-ventilation and framing views to the sparkling PACIFIC OCEAN. The formal living room offers a warm focal fireplace, natural cedar ceiling, and a recessed art niche. Expansive sliders from the great room and living room open to an OCEAN VIEW POOL AND SPA with a SPACIOUS TILED SUN DECK, made for sunset lounging and DINING AL FRESCO UNDER THE STARS. The layout is wonderfully open, yet intentionally defined, with sight lines that draw you toward the outdoors and the enchanting views beyond. This home is a LUMINOUS LIGHT-FILLED CANVAS—ready for your vision: an extraordinary opportunity to re-imagine and elevate a residence of substance, scale, & soul. Set within the prestigious gated Wailea Golf Estates, backing to the 11th fairway of the Wailea Blue Course, and moments to Wailea’s world-class beaches, dining, shopping, golf, tennis, water sports, and spas.

3943 Wailea Ekolu Pl, Kihei
$4,770,000
5 Beds ⋅ 3 Baths ⋅ 732847 MLS
Wake up and smell the Kona coffee, grown, processed and roasted right here on the estate. Kona Rainforest presents a rare opportunity to acquire one of Hawaiʻi’s largest USDA Certified Organic Kona coffee farms, spanning 78.64 acres across three contiguous parcels in the heart of the Kona Coffee Belt. This turnkey farm to cup estate includes two residences, approximately 35 acres of coffee, extensive processing infrastructure, an estate roastery, established brand, equipment, rolling stock and operating business. More than two decades of cultivation have transformed Kona Rainforest from five planted acres into the expansive coffee estate it is today, earning recognition as a Kona Classic Division winner at the Kona Coffee Cupping Competition. Property highlights include: • Approximately 35 acres of coffee at 1,600 to 2,200 feet elevation. • Coffee varieties include Kona Typica, Red Bourbon, SL34 and K7. • Tropical fruit trees including established lychee trees. • Processing infrastructure including optical sorter, fermentation tanks and climate controlled storage. • Original wet mill and drying building remain functional but are not currently in use. • Estate roastery for on site roasting and packaging. • Newly built approximately 8,000 sq ft processing facility. • Established brand, website and online retail channels. Entirely off grid, the processing facility is powered by a 39 kW photovoltaic array with Blue Ion battery storage and 48 kW Generac backup. The two residences are powered by a separate solar system. Rain catchment provides approximately 150,000 gallons of designed water storage capacity. Two ocean view residences convey, including a 3 bedroom, 2 bath main residence with attached great room and a separate 2 bedroom, 1 bath farm dwelling. The operating business, brand, website, vehicles, tractors, and various farm implements are included in the offering.

87-2854 Hawaii Belt Rd, CAPTAIN COOK
$4,750,000
4 Beds ⋅ 4 Baths ⋅ 202614529 MLS
Live in a truly custom designed and renovated home in Waialae Iki, the result of a four year project devoted to craftsmanship, function, and thoughtful design. Enter a kitchen where rich forest green cabinetry echoes the lush greenery surrounding the home, paired with premium Thermador appliances with integrated smart technology. This four bedroom, three and a half bath residence features two primary suites, high vaulted ceilings, custom bathrooms, and carefully selected finishes throughout. A whole home water purification system, thoughtfully engineered drainage, and an enlarged garage reflect the attention given to every detail. Seamless indoor-outdoor living and lush landscaping create rare privacy, while the newly plastered and retiled pool and patio complete this exceptional Waialae Iki residence.

1931 Alaweo Street, Honolulu
$4,750,000
3 Beds ⋅ 4 Baths ⋅ 409873 MLS
This 10 acre Piiholo property at 4,000' elevation borders a 41-acre State forest and has incredible ocean and mountain views. The very distinctive and extraordinary main residence, designed by renowned architect Jim Hestand of Maui Architectural Group, is an absolute work-of-art. Almost entirely constructed with old-growth redwood, the architectural inspiration was designed for the well-known concerts and poetry gatherings among the owners in the days of its grandeur...a true legacy property. The main home has recently been thoroughly and lovingly returned to its original beauty and beyond, with the remodeling and modernizing of the kitchen and bathrooms. All of the out-buildings, concrete driveway and landscaping have also been restored. Rare peace and privacy are assured within the grounds. The 2nd residence is reminiscent of a mountain cabin vibe. The 2 residences are separated by many usable acres of trees and orchards. One could certainly imagine this property being ideal for horses. In between the two homes there is an artist/musician studio with flexible use. There are 2 water meters, serving each end of the property. Additionally, there is a large garage/workshop and a useful farm structure. Pi'iholo, is known for cool days and cooler evenings with passing mists, reliable rainfall and refreshing trade winds. There are several respected public schools and excellent private schools in the region. Farmers markets, supermarkets and roadside stands assure you can keep your shopping Up Country. The range of restaurants is remarkable. And for health care, Up Country has it all.

2450 Piiholo Rd, Makawao
$4,700,000
3 Beds ⋅ 4 Baths ⋅ 409698 MLS
Escape to your own private paradise in the serene coastal town of Hana, Maui. This custom-built 3-bedroom, 3.5 bathroom home is a testament to luxury and tranquility, offering an expansive 3295 square feet of carefully crafted living space. Upon entering, you'll be greeted by soaring high ceilings that create an open and airy ambiance, inviting you to unwind in the comfort of this exquisite residence. The open floor plan seamlessly connects the living, dining, and kitchen areas, providing a seamless flow for both relaxation and entertainment. The gourmet kitchen is a culinary masterpiece, featuring top-of-the-line appliances, custom cabinetry, and a spacious island for culinary creations. The primary bedroom is a private sanctuary, offering an en-suite bathroom and showcasing panoramic ocean views that envelop the space in a sense of calm and escape. Each additional bedroom is generously sized and offers its own unique charm and comfort. The well-appointed bathrooms feature elegant finishes and luxurious amenities. Step outside to the expansive 1.1-acre oceanfront property, where you'll be greeted by unobstructed and sweeping ocean views that stretch to the horizon. The tiki bar area is the perfect setting to savor the coastal breeze, while the presence of coconut trees adds to the tropical ambiance. Keep an eye out for passing dolphins and whales, as well as the graceful presence of sea birds, all enhancing the natural beauty of this coastal retreat. A detached garage provides ample space for vehicles and storage, while the ocean view guest suite offers a private haven for visitors or additional living space. Embrace the beauty of the sunrise and the tranquil rhythm of coastal living, as you immerse yourself in the enchanting allure of Hana, Maui. This exceptional property offers a rare opportunity to experience the ultimate oceanfront lifestyle, where each day is graced by the beauty of the sea and the tranquility of coastal living. Whether you're seeking a luxurious permanent residence or a vacation retreat, this home offers a unique blend of elegance, comfort, and natural splendor. Don't miss the chance to make this oceanfront oasis your own. Contact your Realtor today to schedule a private tour and discover the endless possibilities of coastal living in this extraordinary home in Hana, Maui.

51 Kapohue Rd, Hana
$4,650,000
4 Beds ⋅ 3 Baths ⋅ 410691 MLS
Experience classic plantation style charm blended with modern island living at this stunning oceanfront residence on Halama Street. Set on a gated and private .46 acre lot, this home captures the essence of Maui with refreshing ocean breezes, sweeping multi island views, and direct oceanfront access right outside your door. The main residence is sold fully furnished and designed for effortless comfort, while the detached ohana offers flexibility for guests, extended family, or an onsite caretaker. A sparkling in ground pool surrounded by lush island landscaping creates the perfect setting for relaxation and entertaining. From sunrise to sunset, enjoy the ultimate Maui lifestyle in a home that combines timeless character with tropical tranquility. Make 1656 Halama Street your personal Maui oasis. A new asphalt shingle roof is scheduled for completion in September 2026.

1656 Halama St, Kihei
$4,650,000
4 Beds ⋅ 5 Baths ⋅ 406659 MLS
Welcome to 116 Pulelehua Street in Pineapple Hill Estates, where elegance meets leisure! Nestled behind the scenic 7th tee box of the renowned Kapalua Bay Course, this stunning home is designed for both relaxation and enjoyment. With its inviting westerly views stretching down the iconic 7th fairway to Molokai, every evening is graced by breathtaking sunsets that will leave you in awe. This elegant single-story retreat features a thoughtfully designed dual-master suite floor plan that prioritizes comfort and luxury. Imagine waking up to the serene sight of expansive golf course and ocean vistas from the comfort of your own haven. This fully-furnished sanctuary boasts four ensuite bedrooms, accented by exquisite travertine floors and countertops, seamlessly blending style with functionality. As part of the community, indulge in a wealth of on-site amenities: take a refreshing dip in the large heated pool, challenge friends to a match on the tennis/pickleball courts, or simply unwind at the clubhouse. If that’s not enough, the surrounding resort amenities elevate your lifestyle even further. Imagine treating yourself to a day at the award-winning Montage spa, perfecting your swing on world-class golf courses like the Plantation Course and The Bay Course, or savoring delectable dishes at some of the island's finest restaurants—all just moments from your door. Experience the finest blend of luxury living and island lifestyle at 116 Pulelehua Street. Your paradise awaits.

116 Pulelehua St Unit 1, Lahaina
$4,600,000
4 Beds ⋅ 6 Baths ⋅ 729575 MLS ⋅ Kalihiwai Ridge Lot 2 Cpr BLDG.
Most people who know the North Shore know the coastline. Kalihiwai Valley is something else entirely. Set across nearly 4.5 acres, this estate offers a sense of space, balance, and careful design. The primary residence sits at approximately 3,000 square feet on a single level, where clean architectural lines and vaulted ceilings create an easy, natural flow between the kitchen, living, and dining areas. Three well-separated ensuite bedrooms provide privacy, while a dedicated office, guest bath, and laundry add to the home's overall functionality. The compound took shape over sixteen years, from 1998 to 2014. Beyond the main home: a detached guest house, a sizable agricultural building, and an oversized garage, thoughtfully arranged to complement one another. Covered lanais extend the living spaces into the landscape. Gated entry, mostly fenced acreage, and lava rock detailing frame the grounds with a character that takes years to accumulate. To the north, the Nā Pali ridgeline. A waterfall cuts through the mountain face beyond the pond. Sunset arrives from the west across open valley farmland. Five bedrooms, five full baths, nearly 4,800 square feet across the full compound. Minutes to Kīlauea, Princeville, and Hanalei, with access to dining, shopping, golf, and the North Shore's most recognized destinations.

5730-A Kahiliholo Rd, KILAUEA
$4,600,000
4 Beds ⋅ 3 Baths ⋅ 202609398 MLS
This was an Exempt Listing that just went Live on August 18th, 2026. I consider the North Shore as Oahu’s “Hamptons”! Escape and relax, It’s only 35 miles away from Town. Surf out front, Walk the endless beach, Paddleboard, or ride you Cruiser on the bike path, which runs from Three Tables to Sunset Beach. This stretch of coastline is World Known as the “Seven Mile Miracle”. The Sunsets are Absolutely Amazing from the Hot Tub, beach or Lanai. Cleanse your Body and Mind. The North Shore will Change your Life! This home is a short drive to the Ritz Carlton @ Turtle Bay where you can Enjoy Fine Dining and World Class Golf as well. Haleiwa is also a short drive away. The main house has Three Bedrooms and two baths and also has a Recreation Room above the garage, which I consider to be one of the Key Selling Features, with a Murphy Bed, bathroom and Kitchen. The enclosed, two car garage is also helpful for secured surfboard storage.

59-475 Ke Waena Road, Haleiwa
$4,500,000
5 Beds ⋅ 5 Baths ⋅ 410637 MLS
Recently completed, brand New custom 5,000 sq ft home with a 3 car garage in the magnificent Kula I'o neighborhood. Perched at the top of a hill, lot 29 a 2.5 acre parcel gently slopes and enjoys morning sun, mountain, and ocean views. A large infinty edge lap pool with spa, baja ledges, and fountain bubblers overlook a picturesque sunset ocean horizon. This masterfully designed home provides a 4 bed 4 bath main residence with a versatile guest wing that could be used for ohana, gym, or a game room.

173 Huahua Pl, Kula
$4,500,000
3 Beds ⋅ 4 Baths ⋅ 732514 MLS
Club Cottage 14 is a three-bedroom residence within the private Kukuiʻula community on Kauaʻi, offering immediate access to the Club at Kukuiʻula and its full suite of resort-style amenities. As part of the Lodge Collection, both owners and their rental guests enjoy rare and highly privileged access to the private Club at Kukuiʻula—an experience typically reserved for members of this exclusive community. This includes use of a private 18-hole Tom Weiskopf-designed golf course, spa and wellness center, 10-acre organic farm, clubhouse dining, infinity-edge serenity pool, additional resort pools, activity outfitter, and year-round programming and events. The residence features a two-bedroom, two-and-a-half-bath main home and a detached one-bedroom, one-bath guest suite, providing privacy and flexibility. A rare highlight is the private heated pool, a standout within the collection. Interior finishes include Ipe hardwood flooring and an open-concept kitchen that flows into the main living areas. Designed for indoor-outdoor living, the home extends to covered lanais framed by tropical landscaping and a lava rock fire pit. With 2,104 square feet of interior space and 660 square feet of covered lanais, the property is ideal for both entertaining and relaxation. Updated photography reflecting new furnishings will be available soon. Club Cottage 14 offers a turnkey opportunity to enjoy the Kukuiʻula lifestyle immediately as a primary residence, vacation retreat, or legacy property in one of Kauaʻi’s most sought-after private communities—while also extending the rare privilege of Club access to Lodge Collection rental guests, an exceptional distinction within the resort.

2839 Ke Alaula St, KOLOA
$4,500,000
3 Beds ⋅ 2 Baths ⋅ 202614139 MLS
RARE KIHEI BEACHFRONT OPPORTUNITY – PRICED WITH EMPHASIS ON LAND VALUE. An exceptional opportunity to acquire an oversized 15,785 sq. ft. direct beachfront property along highly desirable Halama Street on Maui’s South Shore. With limited beachfront land available, the value here is in the land, location and long-term potential. Enjoy breathtaking panoramic ocean and outer-island views of Lanai, Kahoolawe, West Maui and Molokini. The property fronts a peaceful sandy beach sheltered by offshore reefs, creating calm, shallow waters ideal for swimming and paddling. An existing 3-bedroom, 2-bath residence provides the opportunity to enjoy, rent or renovate while exploring the potential for a future custom beachfront estate, subject to applicable governmental approvals. Conveniently located near restaurants, coffee shops, shopping, parks, tennis courts and golf. Acquire the land. Enjoy it today. Create your vision for tomorrow. A truly rare opportunity to secure a substantial fee-simple beachfront parcel in one of South Maui’s most desirable locations. Whether held for the future, renovated or reimagined, this is an opportunity to own an irreplaceable piece of Maui beachfront.

1756 Halama Street, Kihei
$4,500,000
2 Beds ⋅ 2 Baths ⋅ 410325 MLS
Laulea is often translated as “peace and friendship,” which feels particularly appropriate for one of Spreckelsville’s most desirable private roads. Set on just under one-third of an acre, this inviting house and cottage property captures the relaxed character of Maui’s North Shore. The two-bedroom, two-bath main home was completely rebuilt in 1996 with style, warmth, and distinctive details, including seashell relief work, bamboo accents, and ohia posts. Skylights, open-truss ceilings, and an open kitchen and living area fill the home with natural light, while two spacious covered lanais extend the living space outdoors and create inviting settings for dining, relaxing, and gathering with friends. Built in 2005, the elevated cottage has its own Balinese-inspired character, with merbau wood and travertine floors, vaulted ceilings, Venetian plaster, and thoughtful architectural touches throughout. A flexible bonus space below the cottage provides additional room for a home office, gym, studio, storage, or other uses. The lovely backyard and two outdoor showers are perfectly suited to life near the beach. Multiple beaches and surf spots are nearby, along with Maui Country Club, Kaunoa Senior Center, Pa?ia, and convenient access to OGG, Whole Foods, and Costco. Peaceful, private, and full of personality, this is a special little compound in one of the North Shore’s most sought-after neighborhoods.

450 Laulea Pl, Paia
$4,500,000
7 Beds ⋅ 5 Baths ⋅ 202611944 MLS
3 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:5 beds and 4.5 baths across three levels. The 1st level includes a kitchen & living room opening to an ocean-view lanai, primary bed & 2nd bed with Jack-and-Jill bath. The level below offers a 2nd living area, an ensuite bedroom with an adjoining bed, powder room, office, laundry, and another lanai. The 3rd level is a 1-bed apartment with kitchen, living room, and bath. Outside is a pool, tiki bar, sauna, BBQ area, garage, and carport. The 2ND STRUCTURE:2-bed, 1-bath ohana with kitchen, living room, 3-car garage, & office/studio. The 3RD STRUCTURE: 1-bed, 1-bath cabin. Turn-key & fully furnished, the property includes 71 solar panels, smart-home features, tropical landscaping, koi pond, waterfalls, and mango, avocado, Meyer lemon, & banana trees. The kitchen features a Wolf range, Sub-Zero refrigerator/freezer, & Fisher & Paykel appliances. Views include Kaho?olawe and Lana?i. Rarely available combination of acreage, multiple living spaces, & resort amenities.

3264 Keha Drive, Kihei

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