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$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.

$490,000
1 Beds ⋅ 1 Baths ⋅ 202600985 MLS ⋅ FS - Fee Simple Tenure ⋅ Diamond Head Plaza BLDG.
Rarely available! This charming 1-bedroom, 1-bath condo is ideally located in the vibrant and iconic Diamond Head and Waikiki neighborhood, offering the perfect blend of comfort and convenience. Just a short stroll from world-famous beaches, trendy shops, and eclectic dining options, this home provides a peaceful retreat while still being in the heart of Honolulu’s most sought-after area. With a thoughtfully layout overlooking the pool area, charming finishes, and plenty of natural light, it’s an inviting space for both relaxation and entertaining. Whether you’re enjoying the stunning local scenery or embracing the lively atmosphere nearby, this condo offers the ultimate island living experience. Don't miss your opportunity, schedule a showing today!

3061 Pualei Circle Unit 306, Honolulu

Listing courtesy of Locations LLC.

$1,099,000
5 Beds ⋅ 2 Baths ⋅ 202600101 MLS ⋅ FS - Fee Simple Tenure
BIG PRICE CHANGE~A "DO NOT MISS" CHANCE! For Solid, mid-century custom designed Home in the "Carlos Long" subdivision of Palolo! Property emanates a tropical Country-like feel while remaining close to the amenities & urban life of Kaimuki, Honolulu, Oahu. Only one (1) Owner, lovingly built a spacious layout containing total 5 Bdrms, 2 Baths, 2-Carport parking. Includes special features like a tatami-like area w/ Shoji-style sliding doors that can double as a workout, office/den? - you decide! Well-place Skylights enhance the LARGE living area showcasing solid Lumber, open Wood beams and high vaulted Ceilings. Foundation is a combination of Hollow Tile/Concrete, Wood "Post & Pier" style, and ample crawlspace. Lots of Built-In Cabinets, Shelves, and Closet spaces throughout plus in Master, a "Furo" style tub, His & Her Vanity/Sink spaces. Inside, natural lighting helps promote a constant, tranquil feeling with surrounding Lush green Views of Trees and Mountains that are so peaceful, one can often hear birds and nothing else! Easily can be customized for Home + Work from Home needs, Multi-Generational housing, with room to expand, futher develop. Showings by Appointment only. MAHALO!

2550 Ipulei Way, Honolulu

Listing courtesy of Rainbow Realty International.

$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.

$2,300,000
4 Beds ⋅ 4 Baths ⋅ 202600138 MLS ⋅ FS - Fee Simple Tenure
Brand new! Beautiful house completed in 2022. 4-bedrooms and 4-bathrooms PLUS 2 extra-large rooms (one of therooms has a big walk-in closet and plumbing ready to hook up - can be used as ensuite). Bright and breezy home!Easy to maintain. Pretty garden views from bedrooms. Flexible floorplan. Designed for one large family or multi-family/generation living with 3 separate entrances. Spacious 3 car garage with storage. Large driveway can park3+additional cars. Second-floor lanai offers incredible ocean, mountain, and valley views. Large lot of 22,510 squarefeet (and no back neighbors). Located at the end of a quiet street, situated in a wonderful neighborhood nearshopping, beaches, schools, and scenic spots like Kuliouou Beach Park, Kuliouou Neighborhood Park, and the RidgeTrail. Peaceful and convenient location, short drive to Koko Marina, world famous Sandy Beach, Hawaii Kai TowneCenter, and Costco!

466 Lani Street, Honolulu

Listing courtesy of Locations LLC.

$1,520,000
3 Beds ⋅ 2 Baths ⋅ 202528540 MLS ⋅ FS - Fee Simple Tenure
No stairs. No flood insurance required. Nearly $250K in upgrades. This single-level Aina Haina home on a flat 8,446 sq ft lot checks every box. New kitchen with quartz counters, modern cabinetry, and stainless steel appliances. Both baths fully renovated. New luxury vinyl flooring, fresh paint, and original redwood walls throughout. A private bonus studio with wet bar, full bath, and separate entrance adds flexibility for ohana living, a home office, or guest suite. Out back: mature fruit trees, new vinyl fencing, and gated side access. Two-car garage, washer and dryer included. FEMA Flood Zone X means no flood insurance requirement. Turnkey and ready.

809 Hao Street, Honolulu

Listing courtesy of Blueprint Real Estate Advisors.

$450,000
202528576 MLS ⋅ FS - Fee Simple Tenure
Build your custom home in prestigious Maunalani Heights! Incredible value for an ocean, Diamond Head and city view homesite. P-1 Preservation zoning allows construction of a single-family residence (buyer to verify plans with architect and City). A rare opportunity priced dramatically below comparable view lots. Bring your vision and create something extraordinary.

4730 Halehoola Place, Honolulu

Listing courtesy of Caron B Realty.

$6,995,000
5 Beds ⋅ 6 Baths ⋅ 202528401 MLS ⋅ FS - Fee Simple Tenure
A rare opportunity to own one of Diamond Head's most captivating oceanfront estates at a newly reduced rate; 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

Listing courtesy of Coldwell Banker Realty.

$4,800,000
5 Beds ⋅ 7 Baths ⋅ 202528272 MLS ⋅ FS - Fee Simple Tenure
Perched on the eastern facing perimeter of the prestigious Hawai’i Loa Ridge, 875 Ikena Circle brings a unique grandness to Oahu. Enjoy picturesque views of the Pacific Ocean, Hawai’i Kai Marina, Koko Head, and Portlock. A multi level layout provides the ideal recipe for entertainment and multigenerational living. The main level of the home showcases vaulted ceilings and an abundance of natural light. A spacious primary bedroom suite is situated on the main level adjacent to the living room. Make your way downstairs where you are presented with 3 suites along with an additional living room that opens to the pool deck. A detached pool house provides a personal sanctuary that can be utilized as a home office, a space for guests, or a cozy man cave. Amenities within the community include: Gated entry, 24/7 security, tennis & pickleball.

875 Ikena Circle, Honolulu

Listing courtesy of Coldwell Banker Island Prop.

$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.

$8,875,000
5 Beds ⋅ 6 Baths ⋅ 202525308 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Realty.

$4,750,000
202527707 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Real Broker.

$1,100,000
3 Beds ⋅ 2 Baths ⋅ 202527488 MLS ⋅ FS - Fee Simple Tenure
Nestled in the sought-after Kapahulu area, this well-maintained split-level home featuring 3-bedrooms and 2-bathrooms is tucked in from the main road (Wela Street) being one lot in from the corner. Partially updated since 2019 with new perimeter fencing, vinyl floors, kitchen cabinetry, slider windows (facing the street), ceiling lights/fans, plumbing fixtures and water heater. On-site parking available in a single car carport with room for a second car on the paved driveway fronting the home. Conveniently located near Diamond Head, Kapiolani Community College, and dining/retail establishments in the surrounding Kaimuki and Kahala neighborhoods. Current improvements do not match tax records; Buyer to verify and conduct own due diligence. A rare opportunity to also consider the adjacent property for sale now at 3451 Wela Street (MLS# 202527487).

3451 Wela Street Unit A, Honolulu

Listing courtesy of Estates Royal Limited.

$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.

$1,000,000
2 Beds ⋅ 1 Baths ⋅ 202525423 MLS ⋅ FS - Fee Simple Tenure ⋅ Kainalu BLDG.
Come and experience breathtaking ocean views from this rare beachfront 2 bedroom, located directly on a sandy beach at the base of Diamond Head. Situated on the private, tranquil end of Oahu’s prestigious Gold Coast, Kainalu is one of the most desirable boutique buildings in the area. This spacious Co-op unit welcomes your personal touches and offers an open layout with generous living and dining areas. Enjoy the soothing sound of waves and cool tradewinds drifting through your windows, creating the ultimate island retreat. Step outside to your own private sandy beach—swim, surf at Tonggs, or unwind in the oceanfront lounge area. The unit includes a covered parking stall and in-unit washer and dryer for your convenience. The secure building features easy walk-up or elevator access and a peaceful, quiet environment. Located just minutes from Waikiki, Kapiolani Park, Diamond Head Lookout, and the Outrigger Canoe Club, Kainalu offers the perfect balance of serenity and island lifestyle. Live the Gold Coast lifestyle — where every day feels like a vacation.

2801 Coconut Avenue Unit 3E, Honolulu

Listing courtesy of Executives Properties, Inc..

$15,000,000
202524575 MLS ⋅ FS - Fee Simple Tenure
Kahala Avenue ocean front property. Opportunity to design/build your luxury residence. All Permits, Certifications, Assessments, Plans & Surveys have expired. Removal of Condominium Registration & Map, Chapter 5148, Declaration of CPR, Bylaws on 2/19/25. As-Is. Buyer to do own due diligence.

4607 Kahala Avenue, Honolulu

Listing courtesy of Chaney Brooks Residential LLC.

$1,175,000
4 Beds ⋅ 2 Baths ⋅ 202524204 MLS ⋅ FS - Fee Simple Tenure
This 4 bedroom exudes the peaceful and serene energy of the beloved Palolo valley! The main suite is a standout with its impressive walk-in closet and luxurious Jacuzzi, complemented by a shower for added convenience. Enjoy the elegance of traditional hardwood floors alongside plush carpeting throughout the home. Energy efficient windows and just a few minutes walk from the park! A beautiful ulu tree graces the property, providing shade and the opportunity to capture priceless moments to play ukulele and sing songs. The refreshing trade-winds flow swiftly through the valley and embraces this home, it truly is a perfect blend of comfort and style.

1541 Palolo Avenue Unit A, Honolulu

Listing courtesy of LUVA Real Estate.

$1,999,999
202523925 MLS ⋅ FS - Fee Simple Tenure
A RARE canvas for a custom vision with gorgeous views and a stunning natural backdrop! This extraordinary 3.3 acre, residentially zoned parcel presents an unparalleled opportunity for those seeking privacy, scale, and possibility in one of Oahu's most coveted neighborhoods! This land is currently structured as a four unit CPR, and is being sold as a package with TMKs: 0001–0004 combined. Whether envisioned as a private estate retreat, multi-generational compound , the opportunity for multiple homes through the existing CPR , or legacy property to hold for future generations, this extraordinary parcel is a rare offering not to be missed. Buyer to conduct their own due diligence with the City and County of Honolulu / Department of Planning and Permitting (DPP) for building options. Also listed as Vacant Land MLS 202523921. Do not enter without an appointment. All parties must sign liability waiver prior to access.

5404 Poola Street, Honolulu

Listing courtesy of Engel & Volkers Honolulu.

$1,999,999
202523921 MLS ⋅ FS - Fee Simple Tenure
A RARE canvas for a custom vision with gorgeous views and a stunning natural backdrop! This extraordinary 3.3 acre residentially zoned parcel presents an unparalleled opportunity for those seeking privacy, scale, and possibility in one of Oahu's most coveted neighborhoods! This land is currently structured as a four unit CPR, and is being sold as a package with TMKs: 0001–0004 combined. Whether envisioned as a private estate retreat, multi-generational compound , the opportunity for multiple homes through the existing CPR, or legacy property to hold for future generations, this extraordinary parcel is a rare offering not to be missed. Do not walk the property without appointment and signed waiver. Buyer to conduct their own due diligence with the City and County of Honolulu on desired build out.

5404 Poola Street, Honolulu

Listing courtesy of Engel & Volkers Honolulu.

$530,000
2 Beds ⋅ 2 Baths ⋅ 202524022 MLS ⋅ FS - Fee Simple Tenure ⋅ 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

Listing courtesy of FAMILY Hawaii 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.

$1,850,000
3 Beds ⋅ 2 Baths ⋅ 202523436 MLS ⋅ FS - Fee Simple Tenure
Two properties to be sold together. 1944 10th Ave Apt A, TMK: 3-4-001-041 (Lot - 8,136 sf) with 1-DWELLING, 1944 10th Ave, TMK: 3-4-001-126 (Lot - 4,988 sf), with 1-DWELLING, The two lots total approximately 13,124 sf on R-5 zoning. All improvements to be sold in "As Is" condition. Listing Agent to be On Site for all showings. Please do not disturb tenants. Adjoining 1935 9th Avenue, TMK; 3-4-001-009 (Lot - 15,644 sf) recently sold.

1944 10th Avenue Unit A, Honolulu

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

$1,850,000
3 Beds ⋅ 2 Baths ⋅ 202523428 MLS ⋅ FS - Fee Simple Tenure
Two properties to be sold together. 1944 10th Ave, TMK: 3-4-001-126 (Lot - 4,988 sf), with 1-DWELLING 1944 10th Ave Apt A, TMK: 3-4-001-041 (Lot - 8,136 sf) with 1-DWELLING. The two lots total approximately 13,124 sf on R-5 zoning. All improvements to be sold in "As Is" condition. Listing Agent to be On Site for all showings. Please do not disturb tenants. Adjoining 1935 9th Avenue, TMK; 3-4-001-009 (Lot - 15,644 sf) recently sold.

1944 10th Avenue, Honolulu

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

$985,000
202521657 MLS ⋅ FS - Fee Simple Tenure
Rarely available 3.98-acre parcel on La'i road in Palolo, minutes from the freeway, Kahala Mall, beaches, restaurants, schools, and more. Featuring panoramic ocean and mountain views, this special property provides the opportunity to build your dream home (Zoned P-1 with an allowable 5,000 square foot home). This parcel offers the convenience of town living while affording privacy and the quiet of the country. Located on a private lane in the back of Palolo Valley

2755 Lai Road, Honolulu

Listing courtesy of Compass.

$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.

$12,000,000
6 Beds ⋅ 4 Baths ⋅ 202520628 MLS ⋅ FS - Fee Simple Tenure
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

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.

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.