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$3,650,000
8 Beds ⋅ 6 Baths ⋅ 202612081 MLS ⋅ FS - Fee Simple Tenure
Nestled in the prestigious hillside community of Maunalani Heights, this exceptional residence offers an ideal blend of contemporary luxury, expansive living spaces, and breathtaking views of Diamond Head and the Pacific Ocean. Situated on a generous sized lot, the home provides over 5,500 square feet of interior living space designed for both grand entertaining and comfortable island living. The kitchen is a chef's delight, equipped with Sub-Zero and Wolf appliances. The thoughtfully designed floor plan features multiple living areas, spacious bedrooms, and a flexible lower-level suite with a separate entrance, ideal for extended family, or guests. Just moments from Kaimuki's vibrant dining scene, Waikiki’s renowned beaches, Downtown Honolulu’s business district, and some of Oahu’s most highly regarded schools, the property provides the perfect balance of scenic beauty and everyday convenience.

4556 Sierra Drive, Honolulu

Listing courtesy of Coldwell Banker Island Prop.

$1,968,000
3 Beds ⋅ 2 Baths ⋅ 202611859 MLS ⋅ FS - Fee Simple Tenure
Perched on the slopes of Maunalani Heights, this beautifully maintained midcentury home offers breathtaking wraparound views of Diamond Head, coastline, & Pacific Ocean. Large windows & built-in seating w/storage frame the scenery, filling the home w natural light & capturing serene treetop views. Open living spaces flow seamlessly from the kitchen to the dining & main living areas, enhanced by wood beam details, original oak floors & a charming breakfast nook. Thoughtfully cared for over the years & with only two owners, the home blends classic character w modern upgrades including newer appliances, split A/C throughout, Carrera marble countertops in both bathrooms, 200-amp service, EV charger readiness (2–240V outlets), 37 owned PV panels & new roof in 2017. Owners have thoughtfully completed additional improvements & enhancements, ensuring the property is presented at its very best for its next owner.The flexible layout includes a spacious lower-level primary suite or in-law setup w/its own living area, plus a dedicated laundry room. Enjoy a quaint enclosed courtyard entry, lush tropical landscaping & multiple outdoor spaces w/beautiful trees in a quiet & serene neighborhood.

4765 Matsonia Drive, Honolulu

Listing courtesy of Caron B Realty.

$1,598,000
5 Beds ⋅ 3 Baths ⋅ 202611410 MLS ⋅ FS - Fee Simple Tenure
“CINDERELLA CREST” Does the glass slipper fit? This double-lot property, located in Kahala Heights, offers an exceptional 10,885-square-foot lot with a park-like feel, incredible ambiance, and sweeping views of the sparkling Pacific Ocean, Shoreline, Mountain, and Valley, plus breathtaking Moonrises by night! Enjoy a farm-to-table lifestyle with your own fruit trees. The main level showcases forever views; and includes a primary bedroom with an ensuite bath, a grand living room, a kitchen, a dining area, a home office, and a half bath. Downstairs, you will discover the entertaining area, complete with an oversized wet bar and a large gathering space, perfect for sharing great times with loved ones. Additionally, downstairs, there are four bedrooms with sensational vistas and a bathroom. While the home needs some updates, this is a rare opportunity to .... CREATE YOUR OWN HAPPILY EVER AFTER Just like Cinderella!!

1603 D Paula Drive, Honolulu

Listing courtesy of Coldwell Banker Realty.

$4,950,000
5 Beds ⋅ 5 Baths ⋅ 202606798 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Compass.

$3,388,000
4 Beds ⋅ 3 Baths ⋅ 202610816 MLS ⋅ FS - Fee Simple Tenure
Exceptional custom-designed residence thoughtfully designed to capture unobstructed views of the Pacific Ocean, coastline, and iconic Diamond Head. A foyer with soaring ceilings and a tranquil koi pond creates an unforgettable arrival. The living room showcases three walls of stunning views, soaring ceilings, a wet bar, and direct access to an expansive lanai for effortless indoor-outdoor living. The formal dining room and lanai are adjacent to a grassy area, with a permit for a pool, and stunning ocean vistas. The spacious kitchen boasts a center island, custom cabinetry, walk-in pantry, and casual dining area, while the adjoining family room opens to two lanais, including a large patio for entertainment. The main level includes a bedroom and full bath, ideal for guests or a home office. Upstairs, the primary suite offers a private ocean-view lanai, spa-inspired bath with soaking tub, and walk-in shower. There are two additional bedrooms, a full bath, a laundry room, and a permit to add two additional bedrooms. Stay cool with 7 split AC systems, and reduced electricity fees with $100,000 of new PV solar panels and energy storage batteries. An amazing home with great feng shui!

626 Kahiau Loop, Honolulu

Listing courtesy of Coldwell Banker Realty.

$13,800,000
5 Beds ⋅ 7 Baths ⋅ 202611456 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Compass.

$1,998,000
202611507 MLS ⋅ FS - Fee Simple Tenure
MASSIVE PRICE REDUCTION - PRICED TO SELL! The only BEACH FRONT VACANT LAND, in EAST HONOLULU, OAHU with more than 65 linear feet of sandy beach fronting famous surfing spots Toes and Secrets currently available UNDER $15,000,000. Paiko Beach consists of only 22 residences that are beach front. Priced $1,224,500 BELOW TAX ASSESSED VALUE! Endless water activities are made possible by the barrier reef creating a calm and protected sandy beach front. Seller has obtained APPROVED SHORELINE CERTIFICATION (see listing supplements) 21 feet forward (towards the ocean) of the property line. With all setbacks considered, this property still has a buildable footprint area of more than 4,290 square feet for a single level home! More if you build a second story. Seller has attached and completed the K2 Standard Survey, Shoreline Certification Survey and Topo Map. No Easements or Encroachments. Also listed in MLS under Land Listing MLS #202611508

240 Paiko Drive, Honolulu

Listing courtesy of Coldwell Banker Realty.

$2,500,000
5 Beds ⋅ 5 Baths ⋅ 202611077 MLS ⋅ FS - Fee Simple Tenure
Embrace the paradise lifestyle with this 3-story Kuliouou home nestled just across the street from Paiko Drive, where there's beach access. With over 3,000 square feet of lavish living area and bonus loft space, complete with 5 bedrooms, 5 bathrooms, and private lanais, this ocean view haven is all about luxury and comfort. The flexible floorplan caters to versatile living needs, set up as a separate 3 bed, 1 bedroom, and a studio. Enjoy the added bonus of easy maintenance with luxury vinyl plank flooring. This property provides numerous practical amenities including multiple washer-dryers, entrances, and a solar water heater. Take advantage of the pleasant cross breezes from the tradewinds on cooler days or the newly installed Mitsubishi split system AC units for warmer days. With ample covered parking, this property offers great value for east Honolulu. Seize this opportunity to secure your dream retreat near (yet elevated above) the ocean now!

5864 Kalanianaole Highway Unit B, Honolulu

Listing courtesy of Harcourts Island Real Estate.

$5,560,000
4 Beds ⋅ 4 Baths ⋅ 202604939 MLS ⋅ FS - Fee Simple Tenure
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. Urban living rivaling the great international cities, in the most beautiful place on earth with an idyllic climate, a walkable neighborhood and the ocean just steps away. Within a gorgeous mile walk through Kapiolani Park you’ll find yourself amongst the flagship showrooms of the greatest luxury brands, the finest hotels and the most discerning chefs’ restaurants. Within a one minute walk, and without crossing a street, you are lying on the warm coral sands of Makalei beach. After a swim or surf, you return to your two story 4 bedroom home, walled and gated. Serene and secure. Cool and shaded with vistas of coconut palms, towering Diamond Head and the blue pacific ocean to the horizon. Your surroundings provide visual drama, the sound of the ocean, a sky filled with stars and even a hint of the Milky Way to the southeast, and always, the sweet aroma of plumeria. Your home provides sanctuary. Your secure tropical urban paradise surrounded by the air and the water in one of the most desirable neighborhoods on O'ahu.

3063 Diamond Head Road, Honolulu

Listing courtesy of Compass.

$1,150,000
3 Beds ⋅ 3 Baths ⋅ 202608537 MLS ⋅ FS - Fee Simple Tenure
GREAT NEW PRICE! Elevate your lifestyle in this exceptional Palolo hillside retreat, where million dollar views become an everyday luxury. This beautifully maintained 3-bedroom, 2.5-bath home is perched high above the neighborhood, with sweeping panoramic views of the valley, ocean, and city skyline—offering privacy, peace, security, and a rare sense of retreat. Designed to embrace its stunning setting, the home features an open floor plan with vaulted open beam ceilings, abundant natural light, and a seamless indoor-outdoor flow. Expansive lanais provide the perfect space for sunrise coffee, evening gatherings, or enjoying Waikiki fireworks from home. Thoughtful upgrades, an efficient floorpan and spacious living areas make this home as functional as it is inviting. A standout feature is the substantial covered flex space beneath the home, offering many possibilities... home gym, art studio, wood shop, storage and more! Ideally located, this home offers easy access to beaches, dining, shopping, and entertainment, while providing the serenity of island living. Palolo Valley is that under-the-radar neighborhood stealing the hearts of savvy buyers.

2047 10th Avenue Unit C, Honolulu

Listing courtesy of Keller Williams Honolulu.

$7,895,000
3 Beds ⋅ 4 Baths ⋅ 202609948 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Realty.

$1,495,000
3 Beds ⋅ 2 Baths ⋅ 202609978 MLS ⋅ FS - Fee Simple Tenure
TWO HOMES. ONE LOT. $6,300/MONTH IN RENTAL INCOME. A rare turnkey income property in one of Honolulu's most sought-after neighborhoods. Set on a quiet, private street minutes from Kahala Mall, KCC, Diamond Head, Waikiki, Dog Parks, and Kaimuki! Just minutes away from amazing boutique restaurants and shops: what makes living in Kaimuki so special! If you enjoy Farmers Markets, this home is just minutes away from the weekly KCC market, so you can enjoy fresh produce, food, and all the fun that it brings. This home offers two fully detached, separately metered homes on a 5,000 sf lot, fully updated in 2023 and PRICED UNDER TAX ASSESSED VALUE! Both units are renovated, move-in ready, and in strong rental demand, over $75,000 in annual gross income with tenants already in place. About as plug-and-play as Honolulu investing gets. For owner-occupants: live in one home and let the other offset your mortgage. A true house-hack in a neighborhood people choose to stay in. Investor, house-hacker, or multi-gen buyer, this home checks every box. Schedule your private showing today. **driveway is owned by 3622a Maunalei Ave, subject property has easement to use driveway**

3622 Maunalei Avenue, Honolulu

Listing courtesy of Real Broker.

$1,725,000
4 Beds ⋅ 4 Baths ⋅ 202606994 MLS ⋅ FS - Fee Simple Tenure
Nestled in the sought-after hillside community of St. Louis Heights, this fully renovated, turn-key home offers the perfect blend of modern design and flexible multi-generational living. Spanning two distinct living areas plus a wet bar, the layout is as functional as it is impressive. The home features two luxurious primary suites, two additional bedrooms, and two full bathrooms — all thoughtfully updated with contemporary finishes throughout. A one-car garage plus driveway parking adds everyday convenience. Step outside onto two expansive lanais and take in sweeping city views that make every evening unforgettable. Whether you’re entertaining or simply unwinding, this home delivers an exceptional Hawaii lifestyle. Move-in ready. Nothing to do but enjoy.

2234 St Louis Drive, Honolulu

Listing courtesy of Real Broker.

$6,900,000
7 Beds ⋅ 8 Baths ⋅ 202601735 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Keller Williams Honolulu.

$2,688,000
4 Beds ⋅ 3 Baths ⋅ 202605052 MLS ⋅ FS - Fee Simple Tenure
Major Price Reduction/Owner Says Sell in Waialae Iki V, a gated community with access to Wiliwilinui Ridge hiking trail (views over Waimanalo). Move in ready custom designed 4-bedroom, 3-bathrooms, Family Room, lots of built-ins, office/den, 12 panel PV-owned system, bedroom and bath on the first floor, lots of niches, vaulted wood panel ceilings. Fully walled property with metal driveway gate. Waialae Iki V community association include access to the community center, meeting/party rooms, tennis courts, park area, community activities.

2138 Laukahi Street, Honolulu

Listing courtesy of Takasaki R. E. Services, Inc..

$5,500,000
5 Beds ⋅ 6 Baths ⋅ 202604792 MLS ⋅ FS - Fee Simple Tenure
Hawaii Loa Ridge is one of Oahu’s most prestigious residential enclaves. Privately positioned within the secluded gated community of The Pointe, this remarkable estate captures commanding ocean vistas and sweeping panoramas stretching toward Koko Head Crater. Designed by architect Mark Lively, the five-bedroom, five-and-a-half-bath Mediterranean masterpiece reflects timeless architectural elegance and exceptional craftsmanship throughout. The main level unfolds with a gracious formal dining room, an expansive family room, and a sumptuous primary suite retreat. A grand living room opens seamlessly to the resort-style pool terrace, where shimmering ocean views create an unforgettable backdrop. Upstairs, an additional en-suite bedroom, a secondary lounge, and two adjoining bedrooms provide both comfort and flexibility. A private maid’s quarters is discreetly integrated for added convenience. An extraordinary offering in one of Honolulu’s most coveted neighborhoods, this residence epitomizes elevated island living — where scale, privacy, and breathtaking horizons converge in effortless sophistication. Property to be conveyed "As Is".

525 Moaniala Street, Honolulu

Listing courtesy of ECentury Homes Hawaii LLC.

$3,000,000
4 Beds ⋅ 4 Baths ⋅ 202604599 MLS ⋅ FS - Fee Simple Tenure
View! View! View! This spectacular view home in lower Hawaii Loa Ridge features large 12,631 square foot rim lot with 4,132 square foot home and big swimming pool. Walk into open floor plan with living, dining, kitchen on main level looking out to beautiful views plus one bedroom and full bath on the main level. Primary bedroom upstairs opening out to lanai with ocean and Koko Head views. Two additional bedrooms and family room on lower level. Nice views from every level. Convenient with plenty of driveway parking space. House requires some TLC - ideal for a buyer to live in the house and restore. It's all about the view! Priced below appraisal of $3,381,700 - A Great Value! Property tax is assessed as a non primary residence.

483 Maono Loop, Honolulu

Listing courtesy of Coldwell Banker Realty.

$3,900,000
23 Beds ⋅ 16 Baths ⋅ 202603761 MLS ⋅ FS - Fee Simple Tenure
$975,000 per house! TRY COOPERATIVE ownership-buy w/friends . Each owner gets their own house + rent income from 2 other rentals! DIAMOND HEAD COTTAGES terrific Property Invest-quality property/4 legal full size 2 story individual homes! Flexibility, privacy, comfort & easy living. Views of Kapiolani Park/Waikiki. Loc base Diamond Head 3-6 min.to beach, Kahala Mall; Kaimuki "Foodie" neighborhood; Culinary Inst; Farmer's Market; Kapiolani Park; Zoo; Beach; freeway & bus access etc. Loc boasts the BEST weather on Oahu-sunny blue skies & cooling trade winds. Prime high demand living area. Hayden has City improved sidewalks & underground utilities. EX rental rates & cash flow.3 Homes w/6 bedrooms 2.5+ baths & 4th home has 5 bedrooms 2.5+ baths. Front #1 Liv Area 1,992; Unit "A" (2nd from St) Liv Area 1,792; Unit "B" (3rd from St) Liv Area 1,664;& Unit "C"(end of lane )Liv Area 1,792. A great BUY! Income & Exp. figures short as of Dec 2025 due to vacancy in "B"; now rented for $5,000. "C" now rented $4,850/$5,000.Updated Income & Exp. figures will be provided when available. DREAM property for COOPERATIVE OWNERHSHIP-EACH HOUSE LESS THAN $1M- NOT A CPR. Get Creative! See MLS# 202527826

3331 Hayden Street Unit FRONT,A,B,C, Honolulu

Listing courtesy of KleinCo, LLC.

$1,564,999
3 Beds ⋅ 3 Baths ⋅ 202601634 MLS ⋅ FS - Fee Simple Tenure
STUNNING Diamond Head, ocean, coastline, and city views set the stage for this tastefully renovated and meticulously maintained 3-bedroom, 2.5-bath residence in the highly sought-after St. Louis Heights neighborhood. Over $400,000 invested over the past 12 years in thoughtful improvements and ongoing maintenance, showcasing true pride of ownership. A permitted addition completed in 2017 enhanced the home with: A spacious front deck designed to capture the breathtaking views; An accessory wet bar ideal for entertaining; and An additional full bathroom—adding both functionality and value. The terraced backyard is a peaceful retreat featuring apple banana, papaya, dragon fruit, lime, along with other plantings, perfect for gardening or relaxing outdoors. This is a home that truly must be seen in person to appreciate the quality, care, and attention to detail throughout. Conveniently located with easy access to the freeway, iconic Kaimuki Town, Waikiki, beaches, dining, and shopping. 2025 Permitted 200 amp electrical upgrade completed. Click the Virtual Tour tab to experience the spectacular sunset video with drone footage.

1952 Bertram Street, Honolulu

Listing courtesy of Island Life Homes.

$6,888,000
6 Beds ⋅ 7 Baths ⋅ 202603331 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Marcus Realty.

$37,500,000
5 Beds ⋅ 9 Baths ⋅ 202528159 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Compass.

$10,700,000
3 Beds ⋅ 3 Baths ⋅ 202525708 MLS ⋅ FS - Fee Simple Tenure ⋅ Kuu Makana@ Diamond Hd BLDG.
This turnkey luxury residence is a rare offering, now enhanced with further upgrades. Encompassing more than 4,000 sf of seamless indoor-outdoor living, the home sits at the foot of Diamond Head in the exclusive 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, and 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, and 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

Listing courtesy of Caron B Realty.

$43,000,000
5 Beds ⋅ 7 Baths ⋅ 202520630 MLS ⋅ FS - Fee Simple Tenure
Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties. Zoned R-7.5 and encompassing nearly 80,000 square feet, the estate features an expansive residences and several open lots, offering sweeping ocean views, private/deeded beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Neighboring property located at 3735 Diamond Head Road A, is also available for sale, presenting a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records.

3735- Diamond Head Road, Honolulu

Listing courtesy of Hawaii Life.

$55,000,000
11 Beds ⋅ 11 Baths ⋅ 202520629 MLS ⋅ FS - Fee Simple Tenure
Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties, spanning over two acres across two adjacent parcels. Zoned R-7.5 and encompassing nearly 89,120 square feet, the estate features two residences and an open lot, offering sweeping ocean views, beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Offered as a singular acquisition under TMKs 1-3-1-039-042-0000 and 1-3-1-039-005-0000, Ho‘oluana Estate presents a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records. Last four digits of the listing TMK do not exist, these are used only for MLS entry purposes.

3735 Diamond Head Road, Honolulu

Listing courtesy of Hawaii Life.

$8,000,000
5 Beds ⋅ 6 Baths ⋅ 202507863 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Realty.

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.