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$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.

$26,500,000
5 Beds 8 Baths 202603726 MLS FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Realty.

$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.

$1,188,000
2 Beds 1 Baths 202603557 MLS FS - Fee Simple Tenure
Perched in Maunalani Heights, this cozy home captures the Honolulu lifestyle in its purest form—cool mauka breezes, a peaceful hillside setting, and a front-row seat to sweeping views of Diamond Head, Waikiki, Kahala, and the ocean beyond. Imagine winding down each evening as the sky melts into color and the city lights begin to sparkle below—your daily sunset routine, right at home. Inside, it’s comfortable and inviting—perfect for those who value charm, simplicity, and an incredible backdrop. Outside, the expansive backyard offers exciting room to create: garden, play space, outdoor entertaining, or future possibilities. A bonus basement area adds flexible space for storage, a workshop, or your own creative retreat. A special opportunity to own a view home in one of Honolulu’s most beloved hillside neighborhoods.

3925 Nioi Place, Honolulu

Listing courtesy of Engel & Volkers Honolulu.

$2,495,000
5 Beds 7 Baths 202602181 MLS FS - Fee Simple Tenure
Positioned on a prime rim lot in the highly sought-after Wilhelmina Rise neighborhood, this expansive residence enjoys sweeping panoramic views from the mountains, across the city and Pacific Ocean, to iconic Diamond Head. Situated on a 10,015 square foot lot, the property offers 5,162 square feet of interior living space with a flexible 5 bedroom, 6.5 bath configuration ideal for multi-generational living, guest accommodations, or future income potential. The upper level main residence features 3 bedrooms and 3.5 baths, with a spacious kitchen with handcrafted cabinetry and living areas designed to capture the views. The lower level, with a separate entrance, includes 1 bedroom, a spacious den, and2 full baths, offering excellent separation. A detached cottage adds further versatility. With its elevated setting and substantial square footage, this Wilhelmina Rise home presents a rare opportunity to reimagine a distinctive island residence. Some areas are in average condition, while others would benefit from renovation and repairs. Please do not visit the property without a confirmed appointment, and refrain from trespassing. Please watch the video for more photos!

1732-A Mikahala Way, Honolulu

Listing courtesy of Coldwell Banker Realty.

$1,075,000
1 Beds 1 Baths 202600448 MLS FS - Fee Simple Tenure Diamond Head Ambassador C BLDG.
Experience classic Diamond Head living in this rare oceanfront residence at Diamond Head Ambassador - one of Honolulu's most beloved boutique communities on this iconic Gold Coast. Positioned on the premium 5th floor, this home enjoys a superior view plane with a strong ocean presence and privacy. High ceilings unique to the 5th-floor residences enhance the openness, light, and sense of space. A signature feature of this home is the generous lanai that wraps from the entry side of the residence all the way to the oceanfront-creating seamless indoor-outdoor living and multiple vantage points to enjoy the blue water, sunsets, and natural breezes. Blue-water views frame daily life, complemented by excellent airflow and thoughtful updates that respect the building's timeless character. The functional kitchen offers good storage, the bedroom feels peaceful with an ocean connection, and the layout flows comfortably on a single level. Life here unfolds at the edge of the Pacific. Enjoy the ocean-side saltwater pool, direct ocean access, and the iconic Gold Coast lifestyle!

2957 Kalakaua Avenue Unit 518, Honolulu

Listing courtesy of Hawaii Modern Realty.

$1,599,000
1 Beds 1 Baths 202601401 MLS FS - Fee Simple Tenure Tahitienne Inc BLDG.
Seller is offering $12,000 credit to Buyer at closing. This oceanfront condo on O'ahu's Gold Coast offers an unparalleled living experience, combining modern luxury with natural beauty. The sound of the waves, the stunning ocean and sunset views make for an an incredibly peaceful and rejuvenating experience. This completely and tastefully remodeled unit boasts new cabinets and quartz countertops, luxury vinyl floors, automatic blinds, new appliances, in-unit washer and dryer, smooth ceilings (no popcorn), crown molding. Fully furnished and situated in a secure building, this condo provides direct ocean access. Enjoy the convenience of Kapiolani Park nearby, along with world-class shopping, boutiques, and fine dining just minutes away. This waterfront jewel promises a perfect blend of comfort and elegance in a prime location. Coop taxes are included in the maintenance fee.

2999 Kalakaua Avenue Unit 202, Honolulu

Listing courtesy of REMAX Hawaii.

$6,200,000
3 Beds 4 Baths 202524260 MLS FS - Fee Simple Tenure
This three-story, fairy tale of a home, is your dream come true! Divinely placed on the slopes of Diamond Head, this luxurious, custom built, real life fantasy home, overflows with 3,200 square feet of gorgeous living space; with an additional 745 square feet of purposeful, covered lanai areas. The unforgettable finishes throughout the home, will have you living like royalty with the featured high ceilings to the heavens, and thoughtful layout on every floor. You won’t be able to ignore the newly installed engineered, wood flooring, the newly installed carpet, and you’ll be magnetized by the presentation of the newly painted, interior and exterior. Custom cabinetry made from mahogany wood, teak, and koa, partners perfectly with the home’s gourmet kitchen featuring top-of-the-line appliances, and ample counter space. You may feel the need to pinch yourself because of the options you’ll have to enjoy the majestic Pacific Ocean sunsets and views from your private office, or your panoramic outdoor terrace, or from your refreshing pool or hot tub. This is an extraordinary dwelling that redefines luxury, comfort, and convenience, in Honolulu's most exquisite neighborhood.

3210 Diamond Head Road Unit 4, Honolulu

Listing courtesy of eXp Realty.

$2,325,000
2 Beds 2 Baths 202601109 MLS FS - Fee Simple Tenure Diamond Head Apts Ltd BLDG.
Located in the heart of Diamond Head’s Gold Coast, this unique 2 bed/2bath floorplan in the treasured Diamond Head Apartments Ltd., designed by renowned Hawaii architect Vladimir Ossipoff, includes both a beachside surf level lanai and a Kapiolani Park/Diamond Head view enclosed lanai! Relax on your private vista overlooking the Pacific Ocean with breathtaking sunsets as sailboats, surfers, and canoes play offshore. This 4th floor spacious unit has ideal positioning for amazing views of the surfing waves and coconut trees dancing right in front. Enjoy Kapiolani Park activities, a daily swim just out front, or walk to the Outrigger Canoe Club and Waikiki Elk’s Club. A leisurely stroll past the Aquarium takes you to famous Waikiki beaches into the heart of Waikiki entertainment with award-winning dining options. You are also minutes to Kahala and Ala Moana Shopping Malls. This 3rd generation Kama’aina residence is now offered for the first time and ready to enjoy island style, or prime for your unique interior remodel. Secured parking has outlet ready for an EV. Building amenities enhance that charming beachfront lifestyle where your new life awaits on the prestigious Gold Coast!

2969 Kalakaua Avenue Unit 401, Honolulu

Listing courtesy of Lanai Realty.

$3,900,000
202527826 MLS FS - Fee Simple Tenure
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

Listing courtesy of KleinCo, LLC.

$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.

$10,700,000
3 Beds 3 Baths 202525685 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.

$1,200,000
5 Beds 3 Baths 202524992 MLS FS - Fee Simple Tenure
Big Price Adjustment! Motivated Seller! Spacious Home perfect for large families or multi-generational living! Upstairs consist of 4 bedrooms, 1.5 baths, two living rooms, big open kitchen perfect for gourmet chefs, and downstairs there’s 1 bedroom, living room, bathroom, laundry room & 3 storage areas! Located in private lane with 21 PV Panels, Tesla Batteries, with sweeping views of Waikiki (watch the fabulous fire work displays) and Diamond Head, walking distance from Kapiolani Community College and Diamond Head Theater, minutes away from Waikiki, Kaimuki, Kahala with easy access to shopping, dining, beaches, entertainment and many private and public schools! Fantastic Location! Seller wants to downsize. This home offers the ideal blend of Island Living and Urban Accessibility.

3455A Wela Street, Honolulu

Listing courtesy of Coldwell Banker Realty.

$4,999,000
3 Beds 3 Baths 202523545 MLS FS - Fee Simple Tenure
RARE, VINTAGE, MINT, BEACHFRONT OSSIPOFF GEM! Experience timeless Hawaii luxury in this exquisite 3-bedroom, 2.5-bathroom single-level home, meticulously crafted by renowned architect Vladimir Ossipoff. Nestled on a pristine, sandy, slight beachfront bluff, this architectural gem harmoniously blends indoor and outdoor living, with breathtaking ocean views+uninterrupted tranquility. Step inside this spacious, airy open floor plan, highlighted by classic mid-century design elements and artistry. The gourmet kitchen, equipped with top-line appliances, flows into the dining+living areas, perfect for entertaining guests or enjoying family evenings. Relax+unwind in the new hot tub, watching the stars above+the cool tradewinds, or stay cool inside, with central air conditioning. The enclosed garage and subtle lighting offer convenience+security. Embrace a lifestyle of elegance and a quiet, timeless luxury this special home beholds, while just minutes to world-class dining, shopping, schools, hospitals, and the best of Honolulu, or Waimanalo, Kailua, Northshore, & West Oahu! Every detail of this dream home embodies thoughtful ambiance, privacy, and the expansive beauty of Ossipoff.

5543 Kalanianaole Highway, Honolulu

Listing courtesy of Deep Blue HI.

$6,350,000
2 Beds 2 Baths 202519492 MLS FS - Fee Simple Tenure 3003 Kalakaua BLDG.
Direct oceanfront! Luxuriously upgraded corner apt., with 2 bedms, walk in closet, 2 baths, large media room plus a spacious home office. There are just 2 apts per floor in this highly sought-after boutique building on Honolulu’s Gold Coast. Interior design and renovation by Philpotts Interiors. Custom built-ins and quality finishes throughout. Ocean and sunset views from large lanai & living areas. Diamond Head views from bedrooms. Each apt. has its own semi-private elevator foyer. Two assigned covered parking in gated garage, and 14 guest parking spaces. Pet friendly building. Onsite Resident Manager. Secured Entrance with video call up. Beautifully appointed lobby area. Spacious and turnkey for the most discriminating buyers!

3003 Kalakaua Avenue Unit 5B, Honolulu

Listing courtesy of Coldwell Banker Realty.

$5,999,000
2 Beds 2 Baths 202519099 MLS FS - Fee Simple Tenure 3003 Kalakaua BLDG.
Experience luxurious coastal living in this beautifully renovated oceanfront unit with breathtaking ocean views and the soothing sound of waves. Enjoy sunsets each evening and Honolulu’s city lights by night—all from home. The open layout enhances airflow, bringing the ocean breeze into every room. Each space offers an ocean or Diamond Head view. Two mountain-facing bedrooms provide peaceful Diamond Head vistas. A spacious middle den has a closet, adding flexibility. Newly installed sliding glass doors offer seamless indoor-outdoor living and quiet when closed. The kitchen features a pantry and ample storage. The spa-style bath includes a deep soaking tub with an ocean view and a separate shower. This elegant home blends comfort, thoughtful design, and a prime oceanfront location for exceptional island living.

3003 Kalakaua Avenue Unit 5A, Honolulu

Listing courtesy of Axio Properties.

$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.

$4,280,000
3 Beds 5 Baths 202428792 MLS FS - Fee Simple Tenure
Located inside of Honolulu's most prestigious, gated community, Hawaii Loa Ridge. This is a beautiful 3 bedroom 3 bathroom 2 powder room property with 4,012 sq ft of living space. Property has a large picture window providing a panoramic Ocean and Koko Head View. Beautiful land scaped front and back yard with pool deck to effortlessly enjoy the impeccable weather of Hawaii. Included are the high quality finished travertine flooring, Chef's kitchen with elegant marble countertops, wet bar, numerous edging glass windows, high ceiling , multiple European customs cabinet and automatic shade. A spacious pool deck is excellent for entertaining or looking at the unobstructed view of the ocean. Association offers 24/7 security, Tennis Court and BBQ area. Please use "AS IS" addendum. Prefer Escrow Title Guaranty at Kahala, Relly Hirokawa.

738 Kaulana Place, Honolulu

Listing courtesy of Shuko 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.