Nancy J. Callahan, R(B)

$18,000,000 • Represented Seller

Nestled on the serene Old Makena Road in Maui, this exclusive compound presents an extraordinary opportunity for those seeking a private beachfront retreat. Enclosed within a gated entrance, the property spans approximately 1.43 acres, boasting a stunning 148 feet of beach frontage. The compound comprises four distinct houses, each offering a unique blend of comfort and elegance.

Originally hosting a charming beach house, the property has evolved over the years into a magnificent estate. The main residence is a highlight, featuring an inviting outdoor shower perfect for rinsing off after a day at the beach. The houses have undergone thoughtful renovations, transitioning from wood siding to a sophisticated combination of smooth stucco and rich ipe wood, enhancing their allure and durability.

The outdoor spaces are equally impressive. The expansive lanai is a peaceful haven, complete with a cozy fire pit and breathtaking ocean views, ideal for entertaining or simply relaxing while listening to the waves. This compound is not just a home, but a lifestyle, a private paradise that has been a backdrop for family gatherings and memorable moments. This is a rare chance to own a piece of Maui's coveted coastline, a sanctuary where luxury meets tranquility.

Represented Seller

A rare Makena oceanfront treasure...

A jewel perched on the point at Makena Place. Beautifully designed with 3 to 4 bedroom or den, 3.5 baths, and open kitchen leading to oversized lanai, all in a postcard-perfect Pacific setting. The Great Room with vaulted ceilings also leads to a gracious lanai for all the entertaining you can dream of. Featuring a large lanai on the upstairs for your guests to enjoy whale watching and spectacular sunsets. Steps away, a white sandy cove that is home to turles all year long. Simply the best!!!! Makena Place is a fee-simple residential condominium offering private living with the benefits of a secured, gated community of 10 homes. Onsite resident manager and tennis courts. Please inquire for all the amenties.

Represented Seller

Keauhou at Makena is an awe-inspiring rare residential development of only seven estates. 

Entering through your private gate to 3 acres of a secluded oasis across from the white sands of Palauea Beach is rare indeed.

A stunning welcoming as you step into the great room with soaring ceilings and the nature of elegance surrounding you with matured landscaping and unparalleled 180 degree Pacific Views.

As you explore this truly rare home of 7,000sf with 6 bedrooms, 6 baths, 2 half baths, chef’s kitchen, over-sized wine room, theatre room, all beautifully designed with separate wings allowing for privacy. Imagine your family and friends nestled in luxury as you celebrate everyday life. Enjoy your over-sized infinity pool with spacious lanais framing the home; It is a treasure!

Once in a lifetime location, walking distance to Wailea Resort, steps to Palauea Beach, listen to the ocean and watch spectacular sunsets while enjoying truly a rare estate home.

$9,750,000 • Represented Seller

This extraordinary 39-acre estate offers a rare opportunity to own a piece of Maui’s rich history. The property, originally built in 1858 as the plantation manager’s home for one of Maui’s first sugar plantations, has evolved over the years into a magnificent 10-bedroom, 10.5-bathroom residence. The estate includes a main residence, guest cottage, tennis court, pool, and multiple cottages, all meticulously renovated and maintained. From its regal beginnings to its modern incarnation, this estate whispers the story of Maui’s past.

The property is split into two parcels: the 18.96-acre main parcel features the grand 9,613 sq ft residence, a guest house, tennis court, and pool. The second 20.11-acre parcel includes three caretaker’s cottages, a workshop, and lush grounds featuring over 120 species of trees. With four water meters and a private well, this retreat offers self-sufficiency and tranquility, elevated at 400 feet above sea level with sweeping Pacific Ocean views.

Just minutes from Paia, Makawao town, and prestigious schools like Montessori and Seabury Hall, the estate provides a secluded haven that’s still close to modern conveniences. Whether enjoying ocean breezes or gathering with family and friends, this legacy property embodies kamaʻāina living at its finest, and is offered fully furnished—ready to be enjoyed for generations to come.

Represented Seller

Supremely private, yet moments away from all Wailea has to offer – drive through the gates of this impeccably designed Hawaiian estate and leave the world behind. Expansive lanais merge elegant indoor/outdoor living, and commanding views of the outer islands invite reflection and relaxation. Stylish, elegant interiors offer a stunning welcome to family and guests. Owned by one family and never before listed. With panoramic views of the Pacific and West Maui mountains, this is truly one of Makena’s most exceptional properties.

IslandLiving...balancing breezy tropical design and sophisticated elegance this custom residence is truly a showpiece offering commanding views of the outer islands, Pacific vistas and West Maui Mountains. Whether you're basking by the infinity edge over-sized pool, playing golf on your own par 3 or simply enjoying the privacy of your estate; this unique property welcome's you home. Zoning and design guidelines allow for a separate structure for caretakers of up to 1,000 sq ft.

Keauhou at Makena, an exclusive community consisting of only 7 homeowners. Located within walking distance to the Fairmont Kea Lani hotel and the white sands of famous Palau'ea Beach. A short drive or walk to the Shops at Wailea, five-star hotels, restaurants, championship golf and tennis facilities.

Represented Seller

The minute you walk through the custom Sapele Mahogany doors your heart skips a beat with the 180 degree views of the crystal blue Pacific waters, Makena's Pu'u Olai and Molokini.  With this newly built custom two-story residence you will be able to feel the ocean breeze on your face as the telescoping walls of glass vanish away to leave you standing in an indoor-outdoor wall less home. Beautiful Cumaru hardwood and Portuguese limestone flooring throughout compliment this home.  Oversized great room for entertaining that looks upon the gourmet chef's kitchen that is adorned with top of the line appliances that are sure to make any dinner party a success.  It boasts custom Sapele  cabinets, and a walk-in pantry.  Take a soak in the imported hand carved stone bathtub that you'll find as you enter the Master Bath, complete with his and hers sinks, custom Koa cabinets and a walk in closet. Or get some fresh air in one of the two outdoor private showers where you are transported to old Hawaii surrounded by lava rocks and the sweet smell of plumeria.

Enjoy the pool's shallow tanning deck while gazing at Molokini just beyond the 55' infinity edge pool, or enjoy the stars and let the jets massage you in the custom champagne edge jacuzzi. This smart house features Sonos sound system that can be adjusted for a customized listening experience in every room. Turn key home also includes full security system equipped with cameras, 4 zone personalized air-conditioning system, your very own golf cart, and many upgrades that you must see for yourself. Custom stairs meander down through the ancient hillside to historic Makena Landing, where you are guaranteed to see a turtle at the famous Turtle Town Point.

Let the sound of the waves sing you to sleep in this brilliant masterpiece. Welcome home.

$4,070,000 • Represented Seller

Seize the opportunity to own a residence that embodies perfection and readiness, conceived from the visionary mind of esteemed Architect John Mattham. This home, initially constructed in 2012, underwent a significant transformation in 2019, ensuring that every detail was meticulously updated to meet the highest standards of modern living. The inclusion of top-tier appliances, sophisticated Lutron lighting systems, and a thoughtfully designed floor plan accentuates the home's seamless blend of style and functionality. Designed for effortless single-level living, the main floor gracefully hosts 3 bedrooms and 2.5 bathrooms, setting the stage for a luxurious and convenient lifestyle.

As you explore further, the lower level unfolds into an elegantly appointed space that includes a 4th bedroom alongside a full bathroom, complemented by an area that can effortlessly serve as a family room or den. This versatile lower level is perfectly configured to accommodate guests, offering them privacy and comfort, or to serve as a dedicated entertainment zone where memories are waiting to be made. The thoughtful layout ensures that every inch of the home is utilized to its full potential, creating a welcoming environment for both residents and visitors alike.

The home's architectural brilliance is further highlighted by Fleetwood doors that lead to an expansive lanai, inviting the outside in and creating a seamless flow between indoor and outdoor living spaces. The lanai, along with a luxurious pool and spa, becomes the heart of the home, a sanctuary for relaxation and social gatherings. This space is designed not only for private enjoyment but also as a picturesque setting for hosting gatherings, where guests can revel in the stunning ocean and sunset views that frame this magnificent property. With every detail carefully considered, this home stands as a testament to exquisite design and unparalleled comfort, offering an unmatched living experience.

Represented Seller

Luxurious island living with unobstructed Pacific vistas, Pu'u Olai and Molokini while overlooking the shores of historic Makena Landing. This newly built one-level hillside residence designed by Greg Bayless seamlessly blends the lines between indoors and out with walls of glass that disappear to enhance the view from every vantage. From the private court yard entrance, complimented by exotic woods, imported stone flooring, teak columns and stone carvings throughout; this home must be viewed. Beautiful finishes and furnishings add to the top of the line quality and craftsmanship.

Represented Seller

Rare, first time ever on the market, the best position on the front row in Wailea Golf Vistas, this exceptional home captures Wailea’s most classic “wow” views. Tim Farrington designed home showcasing the outrageous, protected views of the Pacific and the outer Islands. Perched high above the 16th green & the 17th fairway of the Wailea Blue Course, the entry to this private residence features a waterfall and a pathway of “floating” travertine stepping-stones that guide you to the glass entry doors etched with ocean images of dolphins. Entertain family and friends, home features an open floor plan with window walls of sliding glass doors all pocket, allowing you to open the living and dining areas to the pool lanai creating an expansive indoor / outdoor living area. Travertine lanai surrounds pool, spa, built-in BBQ and wet bar for all your pool-side entertaining and relaxing. Well-appointed kitchen features Bosch and Sub Zero appliances. Spacious ocean view master suite leading out to the pool area, vaulted ceiling paneled in cedar, a "his & hers" master bathroom and a generous walk-in closet. Three guest suites, two with their own separate entrance and lanai. An ocean view office with custom Koa cabinetry. In addition an elevator, two laundry rooms, wine storage, outdoor shower and pool bath.

Represented Seller

1st Offering! A rare top row A building Plumeria plan doesn’t get any better at Ho’olei. Soaring WOW views of outer islands, West Maui mountains, sunsets along with visiting whales, fireworks, will be your focus as you relax and entertain to plan your Maui time... Ho’olei has it all including an elevator in this two story 3 bedroom 3.5 baths that offers oversize lanais upstairs for entertaining with chefs BBQ and downstairs for privacy and relaxing. Top of the line appliances throughout complete this thought out design. Enjoy the beautiful pool, fitness and lush landscaping that is meticulously cared for while all in walking distance to enjoy, along with access to the Grand Wailea should you chose to. The unit has never been in the rental program and being offered unfurnished. An immaculate beauty, this canvas awaits to put your signature and pride of ownership on this exceptional residence.

Represented Buyer & Seller

The grace and beauty of Hawaii are reflected in this one of a kind residence located in Golf Estates, Wailea'a premier gated community.  Spectacular views of the Pacific and outer islands can be seen from this 4,276 sq ft of gracious living space, which includes four bedrooms and four and one-half baths.  The U-shaped home, located on the 4th green of the world famous Wailea Blue Golf Course, surrounds a 20 meter pool with limestone deck"¦truly an elegant family oasis.

The design of the home creates the feel of a sanctuary whether you are in one of the three bedrooms in one wing, the private guest bedroom in the other or lounging quietly on one of three balconies.  Each bedroom has its own spacious marble-lined bathroom with custom built-in wooden consoles topped with marble sinks and counters.  The guest bedroom becomes a haven, with built-in wet bar, small refrigerator and its tranquil view of the serene inner courtyard. 

The elegant living room with a commanding view of the Pacific, lends itself to entertaining, enjoying the solitude of a good book, or watching Maui's famous humpback whales.  Views from every level of the house take in the greens of the Wailea Golf Course, the azure blue of the warm Pacific and dramatic West Maui mountains.

The spacious master bedroom boasts a grand circular lanai for early morning sun bathing or romantic evening sunsets.  A huge walk-in shower in the master bath has dual shower heads and is flanked by twin walk-in closets.

Represented Seller

Paradise has an address: 16 Malukai Lane.  A Rare First Offering at Maluhia at Wailea.  A distinctive custom residence, truly an architectural beauty, along with impeccable finishing's adds a welcoming to "Pu'u Hale" Residence #2.  Traditional Hawaiian design with indoor/outdoor living and oversized lanais featuring views of the Pacific and tropical landscaping making this home a private sanctuary. 

Two master suites with private lanais on each level, two guest bedrooms, one powder room and separate pool bath.  Living pavilion with custom floor to ceiling Mahogany and glass sliding pocket doors with integrated shades opening to expansive lanais.  Expansive chef's kitchen with top of line appliances, interior landscaped courtyard along with a den/office. 

Maluhia with only14 residences can enjoy their private Beach Club, and onsite concierge; all while offering the finest for entertaining family and friends with steps to the white sands of Mokapu Beach.  The Andaz Hotel neighbor to the south makes this resort location a 10!!  A short stroll to the Shops at Wailea, five-star hotels, restaurants, championship golf and tennis facilities.

Represented Seller

This elegant residence, is situated on over half an acre in Wailea’s premiere residential community, The Highlands. Tropical elegance and privacy abounds surrounding this 2-story beauty encompassing almost 5,000 sf of interior living. A stunning architectural design with master suite, library, media, formal dining and casual dining with chef’s kitchen all on one level. Sweeping staircase leads to 3 additional bedrooms, all with en-suite bath. Enjoy ocean views both upstairs and down. Fleetwood doors open the gourmet kitchen to expansive lanais for entertaining or to enjoy the matured tropical landscaping that truly is a piece of paradise. Enjoy your pool and spa together with cascading waterfall. Travertine floors interweave the common areas with the outside elements for true island-style living. Beautifully decorated, move in ready and impeccably maintained. Minutes from the Shops at Wailea, five-star hotels, restaurants, championship golf and tennis facilities and the white sand beaches of Wailea’s coastline.

Represented Seller

Largest Penthouse in Wailea Beach Villas; the award winning BEACHFRONT condominium complex. WBV was voted the #1 resort property in Hawaii by Conde Nast Traveller and #11 in the entire U.S. This exclusive community offers luxurious on-site amenities and is walking distance to Wailea's Five-Star hotels, premier shops, fine restaurants and world-class spas. PH 208 has been home-away-from-home for the owners; the three bedroom condo is in impeccable condition, never rented by the current owners and move-in ready. Contemporary design with top of the line finishes, granite counter tops, central air conditioning and outdoor barbecue grill. Gated entry with guard, 24/7 security, two swimming pools and beach services on Wailea Beach, including towels and cabanas. Two lounges for private events, a game room with kitchen, a state-of-the-art fitness center, fully accessorized business center and a conference room are available to owners and guests.

Represented Seller

Represented Buyer

Represented Seller

Striking interiors with flawless execution, design and finishes complete this penthouse residence. Contemporary design with top of the line finishes, granite counter tops, central air conditioning and outdoor barbeque grill. This exclusive oceanside community offers luxurious amenities and minutes from Wailea's Five-Star hotels, premier shops, fine restaurants and world-class spas. Above the white sands this exquisite penthouse offers stunning panoramic views of the tranquil Pacific Ocean and year-round sunsets. Front desk concierge services provided by Destination Resort.

Represented Seller

Represented Seller

An impeccable rare offering, furnished and brand new!  Never occupied and truly a valued gem.  Papali at Wailea consists of only 24 single family home community with amenities including a 75-foot infinity pool, spa, pavilion and fitness center with on-site property manager.  A low density gated sought after development terraced on 10.46 acres of lush landscaping providing views and privacy.  3-bedroom 3.5 bath desirable one-level floor plan accented with high ceilings, custom cabinets, premium appliances, convenient attached garage and extra storage.  Extended oversized lanai and outdoor grill making this an entertainment statement.  A must see!

Represented Seller

Experience the majestic surroundings of one of Maui’s finest treasures “Maluaka Beach” Share in a lifestyle of the finest features and amenities that these luxurious, spacious residences provide. This is an opportunity yet unseen in Makena. Four exclusive homes in a gated community located on one of the finest beaches in the world. Top of the line construction materials and custom design work will awe as you marvel at these prestigious residences. Seize the opportunity and make your dreams come true. Makena Sunset is an exclusive Oceanside residential condominium community. Enjoy the comforts of single family living with the ease of having your property maintained and meticulously cared for. Each home consists of approximately 4,200 Square feet of interior living space with 4 bedrooms 4 full bathrooms and 2 half baths. The master suite and kitchen are on the main level and the 3 guest bedrooms are located on the lower level. There is also another 1,150 Sq. ft of outdoor covered lanai space with a built in BBQ area. The list of amenities include the following: Private infinity pools and spas, electrically controlled sliding pocket doors, top of the line open floor plan kitchen with upper and lower wet bars, built in Wolf BBQ, all metal work custom designed by Padilla Designs, including: Designer private gates, Brass and copper hand rails, custom Tiki torches throughout the property, as well as artistic woven sculptured walls between each building.

Exclusive new Developer offering. Developer Makena Homes LLC is now offering fee simple, detached single-family condominium homes for sale in the “Makena Sunset” project. The project is located in Makena, Maui, Hawaii at 5415, 5417 and 5419 Makena Road (TMK No. (1) 2-1-7-66, CPR Nos. 1, 2 & 3). The project has four units total which are for residential use only.

Represented Seller

LOCATION! LOCATION! LOCATION! Luxurious One-Acre Makena Estate with privacy and convenience! NEW single level furnished residence completed in 2012 consisting of over 6000 interior square feet including six bedrooms, two of which are masters, six full baths and two 1/2 baths, media room, office, extensive covered lanais, heated pool and spa, three-car garage, lush landscaping situated in One Palau'ea Bay gated community. Spacious custom kitchen featuring granite counters, custom cabinets with Monkeypod inserts and Roasted Birch trim, dual ovens, warming drawer, Viking gas cook top, refrigerator and dishwasher. Amenities also include Stone and Oak wood floors, rich unique wood combinations of Wenge, Knotless Cedar, Roasted Birch and Monkeypod to accentuate the quality throughout including high in-laid ceilings. Only minutes walk to white sandy beach for remarkable ocean activities and to the Fairmont Kea Lani Resort for dining, shopping and all the amenities the Wailea and Makena Resorts offer.

Represented Seller

Represented Seller

A rare first offering of this stunning estate. Privacy and taste throughout complement a single level residence designed by architect Greg Bayless. Custom made bronze bamboo gates leading the way on over an acre of impeccable tropical landscaping. Upon opening your Sapele mahogany double doors, breathtaking views of the Pacific and Molokini welcome you to your hideaway, all with attention to detail throughout. Enjoy the south wing master bedroom and bath along with an outdoor shower and private garden. On the north wing, two very private ensuites with French doors leading to large lanais. All Wolf chef's kitchen awaits accented with cherry cabinets. Media room with separate office. Great room with soaring ceilings, pocket out to over size lanai's which lead to a 32x52 feet saline pool and spa. Entertaining at its best outdoor pavilion, kitchen, bar all with Viking Professional appliances. This exquisite home with Tuscan travertine throughout and meticulously maintained even to the lava rock walls that surround the entire property.

$5,400,000 • Representing Seller

Immerse yourself in the pinnacle of luxury with this 2-bedroom, 2-bathroom oceanfront residence in the heart of Wailea. This high-floor home offers a spectacular 180-degree panoramic view of the Pacific Ocean and West Maui mountains, enhanced by newly installed Koa wood flooring and a modern, elegant interior design. The prestigious community features gated entry, concrete construction, central air conditioning, underground parking, and an ocean-side pool and spa. The beautifully landscaped grounds, complete with outdoor barbecues and a herb garden, are maintained by a dedicated staff. Adding to its desirability, this property also offers the potential for short-term rental opportunities in this exclusive and sought-after location.

Represented Buyer

Represented Seller

Front row in Wailea Golf Vistas, this exquisite home of over 5,000 sf interior living captures Wailea's most classic "wow" views. Positioned high atop the 3rd green and 4th tee box, Old Blue's manicured fairways serve as foreground to an awesome showcase of resort and vast ocean views. This impeccably maintained home features an oversize master suite upstairs with views and privacy and 3 ensuite bedrooms downstairs each with private lanais. The fabulously appointed kitchen with top of the line Sub Zero, Thermador and Wolf appliances and exquisite African Mahogany cabinets with Pomele wood inserts accentuate the granite counters throughout. Generous oval counter top adds to the expansive kitchen area for guest dining and entertaining along with a formal dining area and outside bar. Automatic recessed blinds for easy enjoyment of beautiful sunsets all year round. Nine foot Fleetwood sliders open to a gracious living area for family and friends. Listen to the sounds of the two water falls as they cascade into the salt water pool and spa. Downstairs consists guest bedrooms, additional storage, wine room with Breezearie cooler with outside compressor and guest laundry room for additional convenience. There is extensive use of Indonesian coral used on the exterior of this home.

Represented Seller

Represented Buyer

Represented Seller

Represented Seller

Represented Seller

Represented Buyer & Seller

Represented Buyer & Seller

Represented Buyer & Seller

Represented Buyer & Seller

Represented Buyer

Represented Seller

This recreational dream estate is one of the most exceptionally rare properties in all of Hawaii. Spanning a lush 70-acres, this turn-key property features a stunning custom home that is no less than magnificent. Conveniently located only two minutes below historic Makawao and just above Paia, this legacy estate is situated in the quintessential Maui location and climate - not too wet, nor too dry. Stunning panoramic views of the North Shore and majestic Haleakala will leave you awe-inspired and compelled to take advantage of the impressive 4,400 sq/ft work/dream studio; the ideal space to galvanize creativity and hobby. This estate was designed with minimal maintenance in mind to allow for maximization of enjoyment, comfort, and ease. All qualified buyers must see this property!