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$3,900,000
202527826 MLS FS - Fee Simple Tenure 251 DOM
Each House for less than $1.0M! TRY COOPERATIVE ownership-buy w/friend. Each owner has their own house + rent income from other 2 houses! DIAMOND HEAD COTTAGES terrific Rental Invest-quality property4 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)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#202603761.

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

$37,500,000
5 Beds 9 Baths 202528159 MLS FS - Fee Simple Tenure 267 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

$8,875,000
5 Beds 6 Baths 202525308 MLS FS - Fee Simple Tenure 271 DOM
RARE OCEAN ADJACENT ESTATE ON ROYAL PLACE. Between Royal Place and Kahala Avenue lies an extraordinary estate offering privacy, space & refined coastal living just moments from the ocean. Set on a generous 14,809 sq ft parcel, this remarkable residence features 5 generously sized bedrooms & 5.5 baths, highlighted by a dramatic primary suite with open air lanai, dual walk-in closets & spa-inspired bath. Expansive interiors showcase multiple lounge & living areas designed for entertaining, all overlooking stunning landscaped grounds. A versatile studio apartment w/full bath & kitchenette sits above the 4-car garage, connected through a spacious gym complete w/ climbing wall. Outdoors, an array of inviting spaces includes a sizable poolside covered lanai with dedicated dining & entertaining areas, a free-form swimming pool w/ adjacent spa & cold plunge, dramatic water features & lush tropical landscaping filled w/ flowering trees & stately palms. Blending artistry & discretion, this home captures the essence of modern luxury & timeless sophistication. Conveniently located near multiple beaches, golfing, The Kahala Hotel & premier shopping and dining. Truly a very special property.

4366 Royal Place, Honolulu

$4,750,000
202527707 MLS FS - Fee Simple Tenure 278 DOM
A rare opportunity to create a legacy estate in one of Honolulu’s most prestigious neighborhoods. Set on an expansive 20,021-square-foot parcel along coveted Kahala Avenue, this exceptional homesite offers nearly half an acre of level land—providing the scale and flexibility to design a truly remarkable private residence. Envision resort-style outdoor living, lush tropical gardens, expansive entertaining spaces, and a one-of-a-kind island home tailored to your vision. Ideally positioned moments from the beach, Waialae Beach Park, Waialae Country Club, The Kahala Hotel & Resort, and Kahala Mall, this premier address combines privacy, prestige, and convenience. Estate-sized parcels in Kahala’s coveted beachside enclave are exceptionally rare.

4744 Kahala Avenue, Honolulu

$530,000
2 Beds 2 Baths 202524022 MLS FS - Fee Simple Tenure 326 DOM Regency Park BLDG.
Rarely-available upper floor unit in beautiful Regency Park Condominium.This spacious 2bed 2bath unit has 2 large lanais with sweeping views of the city and coastline.The well-designed floor plan offers a large living room and laundry room, while the primary bedroom has a walk-in closet and ensuite bathroom.Regency Park is located in a tranquil community with a soothing babbling brook beneath the 2 lanais.The property is well-maintained and provides excellent amenities, such as 24hour security,swimming pool,BBQ,tennis courts,a private 2acre park. Just minutes from the vibrant Kaimuki area, enjoy hip cafes, restaurants, boutique shops, and the convenience of being right next to a grocery store, pharmacy, and hardware store. Plus, you're a short walk to the University of Hawaii, Manoa. Kapiolani Community College is also a stone’s throw away, while freeway access and public transport are at your doorstep.Regency Park is a cozy, quiet, and private community whose lofty entryways make you think of a cathedral.A true gem and rare combination of aesthetics and convenience.This unique living space is frequently sought after but rarely available, especially on the exquisite upper floors.

3138 Waialae Avenue Unit 916, Honolulu

$43,000,000
5 Beds 7 Baths 202520630 MLS FS - Fee Simple Tenure 345 DOM
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

$12,000,000
6 Beds 4 Baths 202520628 MLS FS - Fee Simple Tenure 345 DOM
Exceptional Beachfront Luxury on Honolulu’s Iconic Diamond Head! A rare gem on one of Honolulu’s most coveted stretches of beach, this stunning beachfront estate offers an unparalleled lifestyle. Nestled on the prestigious Diamond Head coastline, this exquisite residence sits directly on a pristine white sand beach with crystal-clear waters perfect for snorkeling and a variety of ocean activities. This turnkey home is a true Kama'aina re-treat, offering a balance of comfort and coastal beauty. The property boasts a meticulously manicured lawn, lush tropical landscaping, and an elevated private yard that ensures both serenity and seclusion. Gated entryways provide ultimate privacy and security, making this an ideal retreat. This rare opportunity is exclusively available for purchase either in conjunction with the neighboring property at 3735 Diamond Head Road OR after the larger estate has sold.

3735 Diamond Head Road Unit A, Honolulu

$55,000,000
11 Beds 11 Baths 202520629 MLS FS - Fee Simple Tenure 345 DOM
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

$8,000,000
5 Beds 6 Baths 202507863 MLS FS - Fee Simple Tenure 535 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

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.