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4324 Kaikoo Place, Honolulu
$37,500,000
5 Beds ⋅ 9 Baths ⋅ 202528159 MLS ⋅ FS - Fee Simple Tenure ⋅ 315 DOM
The Hemmeter Estate is a rare, oceanfront estate located at the end of Kaikoo Place on Black Point. Featuring an extraordinary 339.45 linear feet of ocean frontage, this property offers one of the most expansive coastal settings in Hawaii, with exceptional frontage in the heart of Kaikoo. Blending Hawaiian natural elements with European Renaissance–inspired design, the residence showcases exceptional craftsmanship throughout. Set on 35,870 sq ft of land, the estate offers approximately 21,266 sq ft of interior living, complemented by extensive covered and open lanais ideal for entertaining. Highlights include cast-bronze entry doors, coffered Venetian-inspired ceilings, Italian perlato marble staircases and flooring, carved and finished on-site, a two-story oceanfront living room, and refined Art Deco bronze detailing. Amenities include a private theater, library, entertaining lounge, and grotto pool. The expansive primary suite spans nearly 5,000 sq ft and features dual dressing rooms, a fitness area, and sweeping coastline views. The Hemmeter Estate is an irreplaceable oceanfront estate distinguished by scale, privacy, and architectural significance.

4324 Kaikoo Place, Honolulu
213 Kaalawai Place, Honolulu
$30,000,000
5 Beds ⋅ 8 Baths ⋅ 202603726 MLS ⋅ FS - Fee Simple Tenure ⋅ 261 DOM
Experience unmatched sophistication in this one-of-a-kind, award-winning home by Nicholson Companies, now available at an exceptional value—priced below the 2024 appraisal! This modern masterpiece, nestled in the prestigious Cove Area of Diamond Head, offers over 7,465 square feet of living space that seamlessly blends cutting-edge design with island inspiration. From the expansive living areas that capture breathtaking views to the advanced whole-house automation and security systems, this home is a true technological marvel. The chef's kitchen, featuring professional-grade appliances and a spacious butler’s pantry, is a culinary dream. Every corner reveals something extraordinary, from the exquisite interior finishes to the stunning outdoor oasis. This beachfront home represents the pinnacle of island living, now available at an exceptional price that underscores its unmatched quality and prestige. Seize the opportunity to own this extraordinary residence and make it your own private paradise.

213 Kaalawai Place, Honolulu
51 Kepola Place, Honolulu
$22,000,000
6 Beds ⋅ 10 Baths ⋅ 202606611 MLS ⋅ FS - Fee Simple Tenure ⋅ 206 DOM
When a residence transcends architecture, it becomes a work of art. Set across 1.81 acres in the misted beauty of Nuuanu, LIHIWAI is one of Hawaii’s most iconic historic estates, a rare convergence of land, design, and legacy in a truly cinematic setting. Originally built between 1927 and 1929 for Territorial Governor George R. Carter and designed by Bertram Grosvenor Goodhue, the home has been completely restored and is offered following a meticulous renovation by Welch & Weeks, a museum-quality restoration for modern living. Gracious volumes, natural light, and a refined material palette, including ohia hardwood, old-growth redwood, plaster, bronze windows, and limestone, create spaces that feel both expansive yet intimate. The four-bedroom, seven-bathroom main residence is complemented by two guest homes. The grounds unfold as a private sanctuary with a natural auwai, flowing stream, dramatic waterfall, and heated saltwater pool and spa. Set within Nuuanu Valley, this is a composition of historic pedigree, quiet luxury, and natural beauty. A legacy estate, now coming to market.

51 Kepola Place, Honolulu
176 Hanapepe Loop, Honolulu
$16,500,000
6 Beds ⋅ 8 Baths ⋅ 202611158 MLS ⋅ FS - Fee Simple Tenure ⋅ 113 DOM
Sophisticated, Modern, Unlimited Ocean Views...Designed to relish in the beauty of magnificent indoor spaces coupled w/ a seamless integration to expansive outdoor living this stunning ultra-luxury residence designed by renowned HI Architect Jim McPeak offers uninterrupted Diamond HD, ocean & coastline views, and the best direct sunset vistas on the island. Situated on Oahu’s Southeastern shoreline overlooking Maunalua Bay this breathtaking 6-BD, 7.5-BA residence offers exceptional appointments & a true private luxury resort experience. The Great Rm welcomes you w/its awe-inspiring panoramic landscapes, soaring custom wood inlaid ceilings, pocketing walls of glass & assortment of natural stone textures. The chef’s kitchen w/prof appliances provides a wonderful connection to both the dining alcove & lounge areas. The Primary Suite w/ secluded sitting nook, seaside lanai and dream spa like bath is stunning, Each BD suite provides a sensory experience & soothing sounds of the ocean waves. This modern-day masterpiece is complete w/ a gated, dual access driveway providing ample onsite parking + garage parking for 3-cars. For those in search of a stunning island villa, welcome home.

176 Hanapepe Loop, Honolulu
360 Puuikena Drive, Honolulu
$15,950,000
5 Beds ⋅ 7 Baths ⋅ 202615041 MLS ⋅ FS - Fee Simple Tenure ⋅ 84 DOM
Set on one of Hawaii Loa Ridge's most coveted lots, this five bedroom, six and one half bath residence delivers uninterrupted views of Diamond Head, the Pacific Ocean, and Honolulu's coastline from nearly every room, with complete privacy from neighbors and the street. Award-winning architect Jeff Long paired steel-and-concrete construction with interiors built by artisans whose past work spans ultra-luxury yachts and the ateliers of Chanel, Cartier, and Hermes. Book-matched travertine and marble carry through the home, alongside Spinneybeck and Holly Hunt Italian leather walls and Molteni closet systems. A pneumatic glass elevator connects the levels, and a private theater and wine cellar round out the entertaining spaces. The Pininfarina-designed kitchen centers on a Taj Mahal quartzite island, Snaidero cabinetry, dual Sub-Zero refrigerators, and Gaggenau appliances. Outside, a saltwater infinity pool and spa sit within a landscaped lanai framed by the same sweeping views. German-engineered shutters, a full security system, and 24-hour gated access make this a genuine lock-and-go estate.

360 Puuikena Drive, Honolulu
Honolulu
$14,500,000
5 Beds ⋅ 6 Baths ⋅ 202615821 MLS ⋅ FS - Fee Simple Tenure ⋅ 73 DOM
Exceptional Portlock Estate. This oasis is along one of Oahu's most prestigious beaches. Iconic Diamond Head & Sunset Views. Rare Adjacent Vacant Lot. The property features a gated entry, leading to a fabulous private retreat. Inside, you'll find a spacious, flowing floor plan that extends to a beautifully tropical landscaped yard. The home includes a spacious primary bath and a large covered entry. The expansive yard is complete with a pool, waterfall, gas BBQ, and a pavilion, perfect for entertaining. This offering includes 2 separate parcels. A 14,491 sq ft lot with a 2 story 5 bedroom, 5.5 bath home (TMK 1-3-9-3-8) and an adjacent 13,500 sq ft vacant lot (TMK 1-3-9-3-11). To be sold "As Is".

Honolulu
255 & 257 Portlock Road, Honolulu
$14,250,000
6 Beds ⋅ 8 Baths ⋅ 202604666 MLS ⋅ FS - Fee Simple Tenure ⋅ 245 DOM
Spectacular beachfront estate ..two separate parcels seamlessly combined.Stroll through immaculately landscaped grounds with soothing waterfalls throughout and a separate guest studio.Fully walled for privacy.Step into this architectural masterpiece designed by well known architect Jeff Long with grand foyer directly looking out to breathtaking beach, ocean, and Diamond Head Views!! Three primary suite-sized bedrooms..one suite on the main level...all enjoying Diamond Head and ocean views. Two other primary suites on the upper level with "Romeo and Juliet" balconies looking down to the foyer.Open floor plan with soaring ceilings ... finished with the finest materials..hardwood floors,wood trim in bedroom ceilings,etched glass touches,floor to ceiling sliding glass doors..close to island themed restaurants by the marina, shopping, Hanauma Bay, Sandy Beach..Your own Private Hawaiian Paradise..Simply STUNNING!! Both TMK's are being sold together for a total purchase price of $14,250,000. This spectacular dream retreat is also a Celebrity Home ... having been featured in multiple episodes of Hawaii Five-O. Your chance to own a piece of Hollywood and paradise all in one !!

255 & 257 Portlock Road, Honolulu
6015 Kalanianaole Highway, Honolulu
$13,275,000
5 Beds ⋅ 7 Baths ⋅ 202611456 MLS ⋅ FS - Fee Simple Tenure ⋅ 136 DOM
The Paiko Retreat stands as a true Architectural Masterpiece after a comprehensive restoration. Sitting on over an acre of mature landscaping, Kanewai Spring, waterfalls, and koi ponds, there’s no place quite like this home. A unique estate designed by John Hara in 1983, Hara brings an intentional, open-air feeling to this home like he built at the Honolulu Museum of Art, UH West Oahu, and Punahou School. Spanning 9,295 square feet, the interior is vast, yet warm and deliberate. A dedicated primary wing and private sitting room tucked away from the main entertaining areas, plus four guest bedrooms, each with its own ensuite bath and connected by a custom glass elevator. A media room, family room, and private offices provide space for everyone. The transition to the sweeping lanais is seamless. The grounds carry the calm of a private Japanese resort, with gardens and water features weaving through the property. You have direct frontage on Kanewai Spring feeding into Historic Paiko Lagoon. Because it’s a state wildlife sanctuary, the view is strictly nature—quiet and serene. Evenings here are best spent on the lanai watching shorebirds wade through the shallow waters.

6015 Kalanianaole Highway, Honolulu
3735 C Diamond Head Road, Honolulu
$12,500,000
5 Beds ⋅ 4 Baths ⋅ 202613905 MLS ⋅ FS - Fee Simple Tenure ⋅ 102 DOM
TIMELESS DIAMOND HEAD BEACHFRONT LIVING. Tucked away at the end of a private drive on highly coveted Diamond Head Beach, this classic 5-BD, 4-BA beachfront residence presents a rare opportunity to own in one of Oahu's most iconic oceanfront enclaves. Situated on a 15,398 sq ft parcel, the home enjoys spectacular unobstructed ocean views, rolling surf, swaying coconut palms & the soothing sounds of the Pacific from an exceptionally private setting. A welcoming courtyard w/ tropical landscaping & signature plumeria tree leads to light-filled interiors w/ vaulted ceilings & an open floor plan showcasing the sparkling azure waters of the Pacific. Expansive living & dining areas flow seamlessly to the oceanfront lanai, grassy seaside lawn, and steps to the water's edge. The kitchen features granite countertops, abundant cabinetry, dine-in seating & a breakfast nook. The oceanfront primary suite enjoys breathtaking views & spa like bath. Four additional bedrooms offer flexibility for family/guests or office. Conveniently located near Kapiolani Park, Diamond HD hiking trails, golf, Farmers Market, Waikiki, restaurants & shopping. A truly rare opportunity to own on Diamond Head Beach.

3735 C Diamond Head Road, Honolulu
4561 Aukai Avenue, Honolulu
$9,850,000
5 Beds ⋅ 7 Baths ⋅ 202608794 MLS ⋅ FS - Fee Simple Tenure ⋅ 147 DOM
Introducing a rare new luxury construction in the heart of Kahala, where no detail has been overlooked. This stunning estate features a primary residence and guest cottage/gym, both crafted with the finest materials, including custom cedar ceilings, copper gutters, high-quality composite roofing, and lava rock accents throughout. Designed for the discerning buyer, the property boasts a resort-style pool, whirlpool, koi pond, custom cedar gazebo, and expansive lava tile patios and walkways. Inside, you will find a marble primary bath tub, custom wood ceilings, lava tile feature walls, acoustic wall paneling, vanities, and interior tiling of the highest caliber. A true one-of-a-kind opportunity to own a brand new, thoughtfully designed luxury home.

4561 Aukai Avenue, Honolulu
3165 Diamond Head Road Unit 4, Honolulu
$9,500,000
3 Beds ⋅ 3 Baths ⋅ 202525708 MLS ⋅ FS - Fee Simple Tenure ⋅ 346 DOM ⋅ Kuu Makana@ Diamond Hd BLDG.
NEW PRICE!! This turnkey luxury residence is a rare offering, now enhanced w further upgrades. Encompassing more than 4,000 sf of seamless indoor-outdoor living, the home sits at the foot of Diamond Head in the oceanfront enclave of Kuu Makana at Diamond Head. Within this private, gated community, the 3-bed + den/3-bath property exemplifies island elegance & refined sophistication. Rich, handcrafted woodwork flows throughout, elevating its timeless aesthetic. The gourmet kitchen is equipped for the discerning chef, showcasing Sub-Zero & Wolf appliances, custom Koa cabinetry & premium countertops. Generous living spaces incl a fireplace, creating a warm & tranquil setting. Expansive bedrooms offer peaceful retreats w/custom shelving, stunning Koa doors & the convenience of an elevator. Every detail reflects exceptional craftsmanship and thoughtful design. Sustainable feats incl 34 PV panels, 3 TESLA Powerwalls and EV charger. Also features a large 2-car enclosed garage. With unparalleled ocean views, a premier location & impeccably curated interiors, this home stands alone. This is a rare chance to own a piece of paradise in one of Hawaii’s most coveted coastal communities.

3165 Diamond Head Road Unit 4, Honolulu
431/433 Portlock Road, Honolulu
$9,000,000
5 Beds ⋅ 4 Baths ⋅ 202616314 MLS ⋅ FS - Fee Simple Tenure ⋅ 66 DOM
Rare opportunity to own a true Portlock oceanfront estate spanning two separate lots totaling approximately 33,276 sq. ft., from the street to the ocean. The existing residence at 433 Portlock Rd offers direct oceanfront living with a swimming pool, covered lanai, generous yard, recently installed split ACs in every room, and ample off-street parking for 10+ vehicles. Enjoy sweeping ocean, Diamond Head, sunset, and Maunalua Bay views from this exceptional setting. Included is an adjacent 15,000+ sq. ft. vacant lot at 431 Portlock Rd, offering the potential to create a private family compound, build a custom residence, or preserve additional open space and privacy. A unique opportunity to own a substantial double-lot estate in one of East Honolulu’s most desirable oceanfront neighborhoods. TMKs: 1-3-9-016-009 and 1-3-9-016-012.

431/433 Portlock Road, Honolulu
4758 Kahala Avenue, Honolulu
$8,580,000
5 Beds ⋅ 8 Baths ⋅ 202612088 MLS ⋅ FS - Fee Simple Tenure ⋅ 119 DOM
New construction on .41 acres along Kahala Avenue, this 7,741 sq ft residence was designed around light, water and the art of entertaining. Walls of glass rise to soaring ceilings, and three living areas open to one another and to the outdoors in a single continuous flow. At the heart of the home, an interior garden and koi pond bring a stillness felt in every room. Five en-suite bedrooms offer privacy for family and guests. and an attached ADU/guest residence extends the home for visitors or multigenerational living. Studio Becker cabinetry, Miele and Bosch appliances, Italian porcelain tile, and hardwood floors throughout. Minutes from the beach and the Kahala Hotel, where some of Honolulu's best dining is right around the corner.

4758 Kahala Avenue, Honolulu
4125 Black Point Road, Honolulu
$8,000,000
5 Beds ⋅ 6 Baths ⋅ 202507863 MLS ⋅ FS - Fee Simple Tenure ⋅ 583 DOM
It's all about the view...Rare 360-degree panorama that captures breathtaking vistas in every direction. One-of-a-kind retreat designed to immerse you in nature's beauty from glorious Koko Head sunrises to dramatic sunsets over Diamond Head... and mesmerizing wave breaks along the coastline stretch. Improved in 2018, Built in 2008,w/Geoffrey Lewis, Architect. Thoughtful formal, informal and quiet spaces including ground floor suite w/wet bar& separate zoned AC. Heated spa & infinity pool - a masterful design w/its edge seamlessly blending into the horizon as if it flows directly into the ocean below. Easy access to incredible surf breaks and stunning Association's saltwater pool carved in the lava cliff that defines Black Point's charm. Gated and secured community for privacy. This site carries a legacy of ingenuity and distinction, once home to George Hemmeter, renowned inventor whose visionary spirit is echoed in its unique character and reflects the extraordinary essence of his contributions. Once-in-a-lifetime opportunity to own a piece of a prestigious storied history and experience the luxury and serenity that only this exceptional residence can offer.

4125 Black Point Road, Honolulu
365 Portlock Road, Honolulu
$7,950,000
4 Beds ⋅ 4 Baths ⋅ 202604645 MLS ⋅ FS - Fee Simple Tenure ⋅ 198 DOM
Welcome to an oceanfront jewel on Portlock Road. This meticulously maintained, single-level residence presents four bedrooms and four bathrooms across more than 3,800 square feet of thoughtfully designed living space, where comfort and elegance blend seamlessly with the beauty of the Pacific. From the moment you open the front door, your gaze is drawn straight through the home to sweeping ocean views, with Diamond Head framed perfectly against radiant sunset skies beyond. The privately positioned primary suite serves as a tranquil retreat, capturing expansive ocean vistas and gentle trade winds. Designed for effortless entertaining, the well-appointed kitchen features marble countertops, two stoves, and two refrigerators-ideal for gatherings both intimate and grand. The spacious great room flows seamlessly to a covered lanai, extending to the pool and exquisitely landscaped grounds. Private, quiet, and serene, this exceptional residence is a true oasis-an inviting sanctuary to relax and savor refined oceanfront living.

365 Portlock Road, Honolulu
4157 Black Point Road, Honolulu
$7,895,000
3 Beds ⋅ 4 Baths ⋅ 202609948 MLS ⋅ FS - Fee Simple Tenure ⋅ 157 DOM
TIMELESS BLACK POINT OCEANFRONT LIVING WITH SPELLBINDING SUNRISES. Beautifully reimagined oceanfront residence in the seaside community of Black Point offers 3 BD + den/4th BD option, 4 BA and over 4,000 sq ft of interior living on a sprawling 23,214 sq ft parcel. Thoughtfully designed w/a linear floor plan paralleling the coastline, every room captures breathtaking oceanfront vistas overlooking rolling waves, the palm lined shores of Kahala Beach & iconic Koko Head beyond. Expansive open living spaces feature vaulted shiplap ceilings, exposed natural wood trusses, walls of glass & a dramatic lava rock fireplace w/koa wood mantel. The sunken oceanfront lounge area is ideal for relaxing while taking in the soothing sounds of the sea & mesmerizing coastline views. The spacious primary suite enjoys extraordinary ocean views & spa inspired bath w/walk in shower overlooking the Pacific. Seaside lanais, tropical gardens, palms & outdoor spaces create wonderful entertaining areas. Black Point residents enjoy private access to the community’s ocean fed saltwater pool. Exceptional privacy, dramatic views & timeless island living in one of Honolulu’s most treasured oceanfront neighborhoods.

4157 Black Point Road, Honolulu
509 Moaniala Street, Honolulu
$7,800,000
7 Beds ⋅ 10 Baths ⋅ 202617765 MLS ⋅ FS - Fee Simple Tenure ⋅ 42 DOM
Designed by renowned local architect Fritz Johnson, this iconic estate is a masterful expression of architecture, craftsmanship, and island living. Custom interiors and furnishings curated through distinguished Italian design bring a sophisticated yet inviting character to the home. Perched within the prestigious gated community of Hawaii Loa Ridge at The Pointe, the “Pink Pineapple Palace in the Sky” commands panoramic views stretching from Diamond Head across the Pacific and along Oahu’s eastern coastline. Encompassing more than 10,000 square feet of interior living, the estate offers seven bedrooms, a garden room, and 9.5 baths. Imported Italian stone, soaring interiors, and expansive living spaces open seamlessly to the surrounding landscape. An infinity-edge pool overlooks the coastline, while a private wine cellar and multiple lanais provide exceptional spaces for entertaining or simply taking in the beauty of island sunsets. A truly rare offering, this remarkable residence combines scale, elegance, architectural distinction, and breathtaking natural beauty in one of Honolulu’s most coveted gated communities.

509 Moaniala Street, Honolulu
935 Koloa Street, Honolulu
$6,950,000
7 Beds ⋅ 7 Baths ⋅ 202619636 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM
Modern Luxury Meets Island Living in Kahala. Discover the epitome of luxury island living in this stunning, newly built two-story residence in the prestigious Kahala neighborhood. Thoughtfully designed with sophisticated architecture, elevated finishes, and seamless indoor-outdoor living, this exceptional home offers the perfect balance of contemporary elegance and the relaxed spirit of Hawaii. Designed for both grand entertaining and everyday comfort, the home features multiple outdoor entertainment spaces that invite you to enjoy the island lifestyle year-round. Take a refreshing dip in the private pool, host unforgettable gatherings under the Hawaiian sky, or unwind in your own secluded retreat with cabana. With generous living spaces spanning two levels, every detail is designed to deliver comfort, style, and effortless functionality. Set in one of Oahu’s most sought-after residential communities, this exceptional new build presents a rare opportunity to experience modern luxury in the heart of Kahala.

935 Koloa Street, Honolulu
3849 Poka Street, Honolulu
$6,900,000
7 Beds ⋅ 8 Baths ⋅ 202601735 MLS ⋅ FS - Fee Simple Tenure ⋅ 216 DOM
PRICE REDUCED! MOTIVATED SELLER. This luxury home was taken nearly to the studs and rebuilt a few years ago, and it shows. Unobstructed ocean views are framed by 30-foot windows and ceilings spanning the entire front of the house, opening to oversized decks. A rooftop deck adds sweeping views of the coastline, Diamond Head, and the ocean. Quiet, private setting two blocks from Diamond Head Road and a short distance to the beach. Seven bedrooms and six full baths plus two half baths. Includes a separate studio with its own private entrance — one bedroom, one bath, full kitchenette — ideal for multigenerational living, guests, or rental income. Owned 27-panel photovoltaic system keeps energy costs low. Seller financing may be available.

3849 Poka Street, Honolulu
469 A Portlock Road, Honolulu
$6,900,000
3 Beds ⋅ 4 Baths ⋅ 202528103 MLS ⋅ FS - Fee Simple Tenure ⋅ 296 DOM
Rarely will you find a home that evokes quintessential Hawaii living at its finest. This SINGLE LEVEL oceanfront home is located on a LARGE 15,000+lot on prestigious Portlock Rd. It has everything: a beautifully designed Ossipoff home, off-shore breezes, & rare double WIDTH private lane entrance. The local property Owner is the founder of the surf company, Local Motion. He says the area PORTLOCK has the BEST WEATHER IN THE WORLD, the location has direct West exposure w-off-shore breezes, slower living away from the hustle-bustle. Raised in Kailua, the seller has also lived in different areas of Hawaii & chose this area. ONLY a few homes on Portlock Rd. have private land in front, this is one of them. This home sits on the ocean but has NO SAND that attracts people, no music, trash or hanging around. Hawaii Kai has everything needed: 5 surfing areas in front (beginners-advanced), ranked schools, public golf, recreation pools & shopping conveniences. Private & separate entry for Guest room for family or care giving. Hawaii living at its finest; unpretentious, you deserve to live the dream. Rob is a Hawaiian Local & raised in Hawaii all his life & will provide his BIO if asked.

469 A Portlock Road, Honolulu
3647 Diamond Head Road, Honolulu
$6,888,000
6 Beds ⋅ 7 Baths ⋅ 202603331 MLS ⋅ FS - Fee Simple Tenure ⋅ 267 DOM
BREATHTAKING OCEAN VIEWS take center stage from the moment you step through the front doors of this elevated Spanish-style retreat at the base of world-renowned Diamond Head. Perched above neighboring homes, the property offers rare privacy, open sightlines, and the feeling of a private villa. Inside, graceful arched doorways, soaring ceilings, rich ohia wood floors, and beautiful carpentry reflect the home's timeless character. The layout features multiple living areas, a commercial-style kitchen with stainless steel counters, and three ocean-view bedroom suites with vintage bathrooms, and cedar-lined closets- offering a wonderful opportunity to update and personalize while honoring the home's original charm. Originally built by the Magoon family as a gathering space, the lower level includes two one-bedroom units and a studio, each with separate entrances and access to a shared laundry area. These spaces open to a lush, enclosed garden with fruiting trees and greenery, adding flexibility, income potential, a serene outdoor setting in one of Honolulu's most iconic locations.

3647 Diamond Head Road, Honolulu
235 Portlock Road, Honolulu
$6,500,000
7 Beds ⋅ 6 Baths ⋅ 202528543 MLS ⋅ FS - Fee Simple Tenure ⋅ 300 DOM
Tucked behind a gate in prestigious Portlock, this extensively remodeled home offers rare privacy and peace, just a two-minute walk from the beach. Thirty-foot sliding glass doors span the full width of the house and open to a large covered lanai and backyard with a 50-foot saltwater pool and spa. Mature palms along the property line keep the yard secluded. Step through the front door into expansive living spaces with soaring ceilings. The layout includes seven bedrooms, with two large primary suites that each have a private lanai and a luxurious marble bath. A spacious first-floor bedroom-studio with a private entrance, sauna, and kitchenette adds flexibility for guests, a home office, or separate living space. It all sits on a 13,000+ sq ft lot with ¼ shared ownership in a beach access walkway. Costco and two large Hawaii Kai shopping centers, with plenty of restaurants and shops, are a four-minute drive away. Close to the beach, close to everything, in one of the island's most established coastal neighborhoods. Owner financing available.

235 Portlock Road, Honolulu
3330 Tantalus Drive, Honolulu
$6,300,000
3 Beds ⋅ 2 Baths ⋅ 202605681 MLS ⋅ FS - Fee Simple Tenure ⋅ 123 DOM
A rare opportunity to acquire an incredible Honolulu estate. Built in 1908 by Alfred Castle, this remarkable 13+ acre Tantalus property has been held by just four distinguished families, Castle, McCandless-Marks, Dillingham lineages, and the estate of Juan Hamilton—renowned artist and protégé of Georgia O’Keeffe. A stately drive welcomes you with eucalyptus trees where expansive lawns evoke the elegance of a bygone era and invite grand outdoor gatherings. Panoramic views from Diamond Head to Haleiwa showcase striking sunsets over the Pacific. Fragrant puakenikeni, jasmine and white ginger bloom amid a landscape of moss rock walls, brick pathways, and wooded trails. The buildings are rich with historic details and distinctive architectural finishes. A 60,000-gallon water catchment system underscores the estate’s blend of heritage and stewardship. More than a residence, this is a landmark property awaiting its next chapter—a chance to reimagine one of Honolulu’s great estates. For those drawn to the intersection of history, nature and place, this extraordinary offering represents far more than real estate. It is a legacy to inherit, shape, and preserve for generations to come.

3330 Tantalus Drive, Honolulu
3210 Diamond Head Road Unit 4, Honolulu
$6,295,000
4 Beds ⋅ 4 Baths ⋅ 202619936 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM ⋅ Leahi Estates BLDG.
Welcome to one of Diamond Head's most unique and architecturally distinctive homes. Designed by award-winning architect Norman Lacayo and perfectly positioned on the ocean-facing slopes of Diamond Head, this incredible residence offers breathtaking ocean views, spectacular sunsets, and exceptional privacy. Featuring over 3,200 square feet of interior living space, expansive covered lanais, soaring ceilings, and beautiful custom woodwork, the home was designed to take full advantage of its remarkable surroundings. The thoughtfully designed multi-level layout seamlessly connects indoor and outdoor living, while the private pool area, surrounded by lush tropical landscaping and a beautiful waterfall, feels like a magical retreat of its own. Check the surf right from your home, walk over to Leahi Park for morning yoga, or simply relax and enjoy the incredible surroundings. Just minutes from Waikiki, Kapiolani Park, and some of Oahu's most iconic beaches, this is a truly one-of-a-kind property. MLS and tax records may vary. Buyers to do their own due dilligence.

3210 Diamond Head Road Unit 4, Honolulu
671 Kahiau Loop, Honolulu
$5,999,999
5 Beds ⋅ 5 Baths ⋅ 202616928 MLS ⋅ FS - Fee Simple Tenure ⋅ 57 DOM
We invite you to discover a home built for legacy—where family stories flourish and generations thrive. Perched within gated Hawaii Loa Ridge on a double rim lot, this Mediterranean-inspired estate commands sweeping, unobstructed views of the ocean, Diamond Head, and the coastline. Sunsets here are nothing short of breathtaking. This 5-bedroom, 4.5-bath residence showcases premium materials imported from Greece and Germany, offering timeless elegance and understated sophistication. Soaring ceilings and abundant windows bathe every room in natural light, with views from nearly every major space.The primary suite is a private retreat, featuring a 400 sq ft lanai, jacuzzi tub, and walk-in closets. The gourmet kitchen, with German cabinetry, opens to a breakfast nook overlooking the sparkling pool and spa. Outside, the pool deck is ideal for entertaining, while the manicured tropical backyard includes an 880 sq ft sport court. Parking for 3+ cars and 24-hour security complete the offering.We would be honored to host your private showing. May this residence become the heart of your family's enduring legacy—warmth, prosperity, and grace, for generations to come. All offers are welcome!

671 Kahiau Loop, Honolulu
4240 Kaikoo Place, Honolulu
$5,995,000
5 Beds ⋅ 6 Baths ⋅ 202618082 MLS ⋅ FS - Fee Simple Tenure ⋅ 32 DOM
SHORT SALE…. A rare opportunity to own one of Diamond Head's most captivating oceanfront estates at amazing price; truly the best value Diamond Head. This Balinese-inspired masterpiece blends timeless island elegance with modern sophistication. Designed to embrace Hawaii's indoor-outdoor lifestyle, the residence opens seamlessly to panoramic ocean vistas and the rhythmic sound of the waves. This five-bedroom sanctuary showcases bespoke finishes, natural textures, and an architectural flow that evokes both serenity and grandeur. The primary suite offers breathtaking ocean views and a spa-like en-suite retreat, while a private guest apartment-complete with its own entrance-provides stunning views of Diamond Head and total privacy for family or guests. Outdoors, a private tropical oasis awaits. Surrounded by lush landscaping, the grounds feature a resort-style pool, elevated spa, fire pit, and tranquil koi pond, creating an atmosphere of peaceful indulgence. Gated and secure, yet minutes from Waikiki Beach and Diamond Head State Monument, this rare offering perfectly balances luxury, seclusion and convenience. it is the premier value in Diamond Head's pristine oceanfront enclave.

4240 Kaikoo Place, Honolulu
28 Moloaa Street, Honolulu
$5,850,000
5 Beds ⋅ 6 Baths ⋅ 202611061 MLS ⋅ FS - Fee Simple Tenure ⋅ 146 DOM
This remarkable Estate on 21,832 sq ft lot. 4,577 sq ft of living space all on one level, including swimming pool. This 5 bedroom 5.5 bath has sweeping panoramic views of Diamond Head, Ocean, Mountains and the seasonal Whales, December thru March. Architectural elegance and exceptional craftsmanship throughout. Property to be conveyed "as is".

28 Moloaa Street, Honolulu
2999 Makalei Place, Honolulu
$5,690,000
4 Beds ⋅ 6 Baths ⋅ 202604465 MLS ⋅ FS - Fee Simple Tenure ⋅ 210 DOM
“House of Blue Heaven” — an extraordinary Diamond Head estate where architectural heritage meets timeless luxury. Originally designed in 1931 by renowned Hawaii architect Hart Wood, a pioneer of Hawaiian Regional architecture, this distinguished residence reflects his signature fusion of tropical indoor-outdoor living with Japanese and Asian-inspired design. Thoughtfully remodeled by celebrated architect Jeff Long in 1995, the home preserves its historic character while offering refined modern living. This 4-bedroom, 5.5-bath residence encompasses nearly 5,900 sq. ft. of interior living space on an 11,752 sq. ft. lot, with beautiful ocean and sunset views. Soaring ceilings enhance the home’s grand scale and invite abundant natural light throughout. Expansive lanais, a heated pool and spa, and sophisticated indoor-outdoor spaces create an exceptional setting for entertaining and relaxing. Separate guest quarters with private entrance provide flexibility and privacy. Just moments from Kapiolani Park, the Gold Coast, world-famous beaches, and Waikiki’s renowned dining and shopping, this is a remarkable expression of Hawaii architectural history and elevated island living.

2999 Makalei Place, Honolulu
3063 Diamond Head Road, Honolulu
$5,560,000
4 Beds ⋅ 4 Baths ⋅ 202604939 MLS ⋅ FS - Fee Simple Tenure ⋅ 150 DOM
This is not just a rare landmark home standing proudly between the slopes of Diamond head and the turquoise warm waters of Honolulu’s Gold Coast. It is a lifestyle. Completely remodeled in 2000, this home is the only home available in this highly sought after walkable Diamond Head neighborhood. Walk to the sandy beach at Makalei Beach Park, less than one block away, as well as the Gold Coast, Kapiolani Park and Waikiki. This 4 bedroom 4 bathroom 3631 sq. ft. home with pool, rooftop deck with ocean views home is walled, gated, serene and secure. The surroundings provide visual drama with a cool and shaded fully landscaped garden and pool surrounding the home all set between the slopes of Diamond Head and the Pacific Ocean. This property is a sanctuary. A secure tropical urban paradise surrounded by the air and the water in one of the most desirable and rarely available locations on O'ahu. The layout, size and design of this large and well conceived home in one of the best locations is truly special.

3063 Diamond Head Road, Honolulu
3473 Paty Drive Unit 243A, Honolulu
$5,500,000
5 Beds ⋅ 6 Baths ⋅ 202615998 MLS ⋅ FS - Fee Simple Tenure ⋅ 66 DOM
A rare sanctuary nestled above the lush foliage of Manoa Valley, this extraordinary furnished estate offers an unparalleled sense of privacy, serenity, and connection to nature. Set on approximately 9.48 acres of beautiful hillside land, this exceptional retreat feels worlds away while remaining conveniently close to Honolulu. The 6,411-square-foot residence features 5 bedrooms, 4 full and 2 half baths, soaring ceilings, expansive windows, refined finishes, and seamless indoor-outdoor living. A 2021 update added a sleek glass elevator. Breathtaking valley, ocean, city, and sunset views unfold throughout the home. Outside, a heated, ionized infinity pool and separate spa create a private resort-like setting, complemented by a built-in grill and multiple outdoor spaces for entertaining or quiet reflection. An owned 39-panel solar PV system and separate solar hot water enhance the home's energy efficiency. More than a residence, this is a true private haven where luxury, nature, privacy, and tranquility converge in one of Honolulu's most coveted valleys.

3473 Paty Drive Unit 243A, Honolulu

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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