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Search Diamond Head 5 Bedroom Homes

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Newest Diamond Head, HI 5 Bedroom Homes For Sale

4619 Moho Street, Honolulu image
4619 Moho Street, Honolulu $4,950,000

DESIGNED FOR THE WAY WE LIVE IN HAWAI‘I. This beautifully appointed 5 bedroom home in the heart of Kahala offers a spacious floor plan, light-filled interiors, contempora...

  • 5 Beds
  • 4 Baths
  • 202619416 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 7 DOM
132 Kuliouou Road, Honolulu image
132 Kuliouou Road, Honolulu $1,775,000

A rare opportunity awaits with this elegant 5-bedroom, 4-bath Paiko Lagoon residence offering 2,789 sq ft of interior living space plus a versatile ohana unit. Both the m...

  • 5 Beds
  • 4 Baths
  • 202619094 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 17 DOM
3468 Keanu Street, Honolulu image
3468 Keanu Street, Honolulu $2,150,000

From the moment you arrive, you’ll sense what sets this exceptional home apart. Designed and built as a 100% custom residence offering approx 4100 sq ft of living space, ...

  • 5 Beds
  • 4 Baths
  • 202614948 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 24 DOM
1063 Luawai Street, Honolulu image
1063 Luawai Street, Honolulu $1,970,000 ▼

Location, Location, Location - Please Do not miss your opportunity at a RARELY available single-family home located on a desirable street on Luawai street. Single famil...

  • 5 Beds
  • 5 Baths
  • 202615943 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 25 DOM
3128 Hayden Street, Honolulu image
3128 Hayden Street, Honolulu $1,680,000 ▼

A well cared for Kamaaina home, on a quiet street. 1st time on the market. Multi-family dwelling home. The front dwelling 3bdrm 2 bath & 2 other rooms cna be for study/o...

  • 5 Beds
  • 5 Baths
  • 202618308 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 26 DOM
5926 Kalanianaole Highway, Honolulu image
5926 Kalanianaole Highway, Honolulu $2,249,000

Experience elevated East Oahu living from this distinctive Kuliou?ou hillside retreat, showcasing sweeping ocean, coastline, and mountain views! Set on an expansive 18,59...

  • 5 Beds
  • 3 Baths
  • 202618419 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 27 DOM
4240 Kaikoo Place, Honolulu image
4240 Kaikoo Place, Honolulu $5,995,000 ▼

SHORT SALE…. A rare opportunity to own one of Diamond Head's most captivating oceanfront estates at amazing price; truly the best value Diamond Head. This Balinese-inspir...

  • 5 Beds
  • 6 Baths
  • 202618082 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 28 DOM
1449 St Louis Drive, Honolulu image
1449 St Louis Drive, Honolulu $1,680,000

An Artist’s Flair overlooking the City brings this little gem into the SPOTLIGHT. Romantic terraced gardens and inviting outdoor spaces overlook the city to the ocean, cr...

  • 5 Beds
  • 4 Baths
  • 202618318 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 28 DOM
1898-A Iwi Way, Honolulu image
1898-A Iwi Way, Honolulu $1,625,000 ▼

Maunalani Heights - Multi-generational Opportunity: 5 Bed/3 Bath with ocean & Diamond Head views! Main house offers 3 bedrooms and 2 bathrooms on a single level; 2 bed, 1...

  • 5 Beds
  • 3 Baths
  • 202617021 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 42 DOM
671 Kahiau Loop, Honolulu image
671 Kahiau Loop, Honolulu $5,999,999

We invite you to discover a home built for legacy—where family stories flourish and generations thrive. Perched within gated Hawaii Loa Ridge on a double rim lot, this M...

  • 5 Beds
  • 5 Baths
  • 202616928 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 53 DOM
2356 Aha Maka Way, Honolulu image
2356 Aha Maka Way, Honolulu $2,895,000

Perched on a coveted rim lot within the prestigious Waialae Ridgeline Estates Association, this impeccably maintained three-story custom residence captures breathtaking p...

  • 5 Beds
  • 7 Baths
  • 202616940 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 52 DOM
932 10th Avenue, Honolulu image
932 10th Avenue, Honolulu $1,100,000

Conveniently located in the desirable Kaimuki area, this quiet 5-bedroom, 2-bath single-family home features fragrant pikake bushes and bird-of-paradise landscaping in th...

  • 5 Beds
  • 2 Baths
  • 202616802 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 54 DOM
4854 Analii Street, Honolulu image
4854 Analii Street, Honolulu $2,698,000

A rare opportunity to own a newer, custom-designed home on Analii Street in lower Waialae Iki, just minutes from Waialae Iki Neighborhood Park. The upper level features 4...

  • 5 Beds
  • 5 Baths
  • 202613840 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 56 DOM
3765 Lurline Drive, Honolulu image
3765 Lurline Drive, Honolulu $3,150,000

Sweeping views of Diamond Head and the Pacific Ocean provide a quintessential Honolulu setting for this hillside retreat, tucked away behind a discreet gated entry. The p...

  • 5 Beds
  • 4 Baths
  • 202612821 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 56 DOM
1060 Koloa Street, Honolulu image
1060 Koloa Street, Honolulu $3,150,000

RARE OPPORTUNITY ON KOLOA STREET IN KAHALA. Priced below tax assessed value, this is your chance to acquire a substantial estate on one of Kahala's most beloved streets. ...

  • 5 Beds
  • 5 Baths
  • 202615601 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 63 DOM
1633 10th Avenue Unit Apt B, Honolulu image
1633 10th Avenue Unit Apt B, Honolulu $1,649,000 ▼

*SELLER CREDIT OFFERED* Built in 2016 and upgraded in 2026, this 5-bedroom, 3-bath home offers a flexible two-story layout, a spacious fenced grassy yard and parking for ...

  • 5 Beds
  • 3 Baths
  • 202615465 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 76 DOM
2077 10th Avenue, Honolulu image
2077 10th Avenue, Honolulu $1,295,000

“Two Homes, One Property”: The original owner of these two beautiful, classic homes in Palolo valley is ready for the next generation of owners, investors, or developers ...

  • 5 Beds
  • 3 Baths
  • 202614648 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 77 DOM
204 B Hao Street, Honolulu image
204 B Hao Street, Honolulu $2,788,000

A Rare Opportunity - Offered for resale for the very first time, this exceptional artistic Hawaiian estate is nestled at the end of the coveted Hao Street cul-de-sac. Set...

  • 5 Beds
  • 5 Baths
  • 202615222 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 77 DOM
360 Puuikena Drive, Honolulu image
360 Puuikena Drive, Honolulu $15,950,000

Set on one of Hawaii Loa Ridge's most coveted lots, this five bedroom, six and one half bath residence delivers uninterrupted views of Diamond Head, the Pacific Ocean, an...

  • 5 Beds
  • 7 Baths
  • 202615041 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 80 DOM
5599 Kalanianaole Highway, Honolulu image
5599 Kalanianaole Highway, Honolulu $7,000,000

Affectionately, known as 'Hotel Aloha,' a masterpiece of opulence, grace & authentic Hawaiian design. This elegant 2-story private residence features 5 spacious en-suite ...

  • 5 Beds
  • 7 Baths
  • 202614361 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 84 DOM
3735 C Diamond Head Road, Honolulu image
3735 C Diamond Head Road, Honolulu $12,500,000

TIMELESS DIAMOND HEAD BEACHFRONT LIVING. Tucked away at the end of a private drive on highly coveted Diamond Head Beach, this classic 5-BD, 4-BA beachfront residence pres...

  • 5 Beds
  • 4 Baths
  • 202613905 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 98 DOM
167 Maono Place, Honolulu image
167 Maono Place, Honolulu $3,280,000

Spacious 5 bedroom 4 bath home on Maono Place, a quiet interior street, within prestigious Hawaii Loa Ridge. This home features a covered lanai with beautiful sweeping o...

  • 5 Beds
  • 4 Baths
  • 202613577 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 102 DOM
1938 Bertram Street, Honolulu image
1938 Bertram Street, Honolulu $1,650,000 ▼

Discover a rare opportunity in the highly desirable St. Louis neighborhood! This versatile 5-bedroom property features a legal, permitted ADU, offering flexibility for mu...

  • 5 Beds
  • 2 Baths
  • 202613079 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 111 DOM
4758 Kahala Avenue, Honolulu image
4758 Kahala Avenue, Honolulu $8,580,000

New construction on .41 acres along Kahala Avenue, this 7,741 sq ft residence was designed around light, water and the art of entertaining. Walls of glass rise to soaring...

  • 5 Beds
  • 8 Baths
  • 202612088 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 115 DOM
917 Iiwi Street, Honolulu image
917 Iiwi Street, Honolulu $5,495,000 ▼

Privately gated and offered fully furnished, this exceptional Mediterranean-inspired estate evokes the ambiance of a private resort. Crowned by a striking turquoise tile ...

  • 5 Beds
  • 6 Baths
  • 202612065 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 126 DOM
5811 Kalanianaole Highway, Honolulu image
5811 Kalanianaole Highway, Honolulu $4,950,000

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 se...

  • 5 Beds
  • 5 Baths
  • 202606798 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 130 DOM
1484 Halekoa Drive, Honolulu image
1484 Halekoa Drive, Honolulu $1,225,000

MANY POSSIBILITIES AND WONDERFUL VIEWS IN CONVENIENT WAIALAE NUI RIDGE! Three separate living areas, each with its own entrance, not connected by interior stairs. The mai...

  • 5 Beds
  • 4 Baths
  • 202611545 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 130 DOM
6015 Kalanianaole Highway, Honolulu image
6015 Kalanianaole Highway, Honolulu $13,275,000 ▼

The Paiko Retreat stands as a true Architectural Masterpiece after a comprehensive restoration. Sitting on over an acre of mature landscaping, Kanewai Spring, waterfalls,...

  • 5 Beds
  • 7 Baths
  • 202611456 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 132 DOM
5436 Poola Street, Honolulu image
5436 Poola Street, Honolulu $2,895,000

Nestled on a beautiful mountain range in one of Oahu’s most sought-after locations is this tastefully renovated Waialae Iki home. The property boasts a flexible layout wh...

  • 5 Beds
  • 5 Baths
  • 202611278 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 139 DOM
5864 Kalanianaole Highway Unit B, Honolulu image
5864 Kalanianaole Highway Unit B, Honolulu $2,500,000

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...

  • 5 Beds
  • 5 Baths
  • 202611077 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 140 DOM
4561 Aukai Avenue, Honolulu image
4561 Aukai Avenue, Honolulu $9,850,000 ▼

Introducing a rare new luxury construction in the heart of Kahala, where no detail has been overlooked. This stunning estate features a primary residence and guest cottag...

  • 5 Beds
  • 7 Baths
  • 202608794 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 143 DOM
1030 16th Avenue, Honolulu image
1030 16th Avenue, Honolulu $1,748,880

Rare opportunity to own three separate homes on one lot! Live in one and rent out the others for added income potential. Situated on a 7,500 sq. ft. lot and zoned R-5, th...

  • 5 Beds
  • 3 Baths
  • 202610098 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 143 DOM
399 Puuikena Drive, Honolulu image
399 Puuikena Drive, Honolulu $5,090,000

Open House Cancelled 7/26/26 Nestled in the prestigious Hawaii Loa Ridge, this exceptional residence at 399 Puuikena offers breathtaking 180-degree panoramic views s...

  • 5 Beds
  • 4 Baths
  • 202610282 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 144 DOM
2505 Saul Place, Honolulu image
2505 Saul Place, Honolulu $2,570,000 ▼

BRAND NEW HOME – RARE OPPORTUNITY in Highly Desirable St. Louis Heights! Enjoy breathtaking panoramic views of Diamond Head, the ocean, and the city skyline—this is trul...

  • 5 Beds
  • 4 Baths
  • 202609866 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 153 DOM
523 Kiholo Street, Honolulu image
523 Kiholo Street, Honolulu $1,350,000

Attention investors and buyers looking for a great opportunity: this five-bedroom, two-and-a-half-bath home in Aina Haina offers incredible potential. The property includ...

  • 5 Beds
  • 3 Baths
  • 202607891 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 189 DOM
928 9th Avenue Unit C, Honolulu image
928 9th Avenue Unit C, Honolulu $1,563,000 ▼

Welcome to this beautiful designed home located in highly desirable Kaimuki with city and sunset view, very convenient to school, shops and eatery places. This 5/3 home h...

  • 5 Beds
  • 3 Baths
  • 202606577 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 208 DOM
525 Moaniala Street, Honolulu image
525 Moaniala Street, Honolulu $5,500,000

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 ca...

  • 5 Beds
  • 6 Baths
  • 202604792 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 239 DOM
213 Kaalawai Place, Honolulu image
213 Kaalawai Place, Honolulu $30,000,000 ▲

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 appraisa...

  • 5 Beds
  • 8 Baths
  • 202603726 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 257 DOM
1732-A Mikahala Way, Honolulu image
1732-A Mikahala Way, Honolulu $2,200,000 ▼

A New Opportunity at a New Price! Positioned on a prime rim lot in the highly sought-after Wilhelmina Rise neighborhood, this expansive residence has sweeping panoramic v...

  • 5 Beds
  • 7 Baths
  • 202602181 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 266 DOM
875 Ikena Circle, Honolulu image
875 Ikena Circle, Honolulu $4,800,000

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 O...

  • 5 Beds
  • 7 Baths
  • 202528272 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 308 DOM
4324 Kaikoo Place, Honolulu image
4324 Kaikoo Place, Honolulu $37,500,000

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 ...

  • 5 Beds
  • 9 Baths
  • 202528159 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 311 DOM
4125 Black Point Road, Honolulu image
4125 Black Point Road, Honolulu $8,000,000 ▼

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 ...

  • 5 Beds
  • 6 Baths
  • 202507863 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 579 DOM

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

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Elizabeth La Riva is a real estate team affiliated with Compass. Compass is a licensed real estate broker with a principal office in Oahu, Hawaii, and abides by all applicable equal housing opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to accuracy of any description. All measurements and square footages are approximate. This is not intended to solicit property already listed. Nothing herein shall be construed as legal, accounting or other professional advice outside the realm of real estate brokerage.

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