Oahumilitaryrealestate.com
  • Home
  • Advanced Search
  • VA Loan Resources
  • PCS Resources
  • About Us
  • Blog
  • Contact Us
Login
(808) 554-9667

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Search Diamond Head 5 Bedroom Homes

TO
Advanced Search

Address Search

Newest Diamond Head, HI 5 Bedroom Homes For Sale

1474 Kamole Street, Honolulu image
1474 Kamole Street, Honolulu $2,800,000

First open house 7/26/2026 from 1:30 - 5:00. Exceptional views, exceptional house!! Rare opportunity to make this coveted combination your home! Sweeping ocean views incl...

  • 5 Beds
  • 3 Baths
  • 202613575 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 5 DOM
820 10th Avenue, Honolulu image
820 10th Avenue, Honolulu $2,395,000

Discover a rare Kaimuki find — two separate homes on one expansive 10,000 sq ft lot, zoned R-5. This is the multi-generational or income-producing property you've been wa...

  • 5 Beds
  • 2 Baths
  • 202610744 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 4 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
  • 7 DOM
653 Ulumaika Street, Honolulu image
653 Ulumaika Street, Honolulu $2,990,000

Discover a rare opportunity to design, remodel, and renovate to your liking in coveted Kahala! Situated on a generous 10,855-square-foot flat lot, this spacious 5-bedroom...

  • 5 Beds
  • 4 Baths
  • 202610898 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 7 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
  • 11 DOM
1938 Bertram Street, Honolulu image
1938 Bertram Street, Honolulu $1,750,000

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
  • 20 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
  • 24 DOM
1492 Halekoa Drive, Honolulu image
1492 Halekoa Drive, Honolulu $1,825,000

Most homes trade elevation for the view—climb higher, live farther from everything. This Halekoa Drive home rewrites that story: nearly 180 degrees of open ocean and Diam...

  • 5 Beds
  • 3 Baths
  • 202611287 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 23 DOM
1766 St Louis Drive, Honolulu image
1766 St Louis Drive, Honolulu $1,725,000 ▼

PRICE IMPROVEMENT! Where else in St. Louis Heights will you find potential for three separate living areas, two separate driveways, and an ocean view? Multigenerational l...

  • 5 Beds
  • 5 Baths
  • 202612360 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 24 DOM
1717 Palaau Street, Honolulu image
1717 Palaau Street, Honolulu $2,950,000

Stunning Ocean and Diamond Head views highlight this residence located halfway up the prestigious and highly sought after Waialae Iki ridge. Offering 5bedrooms, 5 baths p...

  • 5 Beds
  • 5 Baths
  • 202612377 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 25 DOM
1717 Iwi Way, Honolulu image
1717 Iwi Way, Honolulu $2,999,000

Breathtaking Diamond Head, ocean views and soaring high ceilings greet you entering this luxury residence. The spacious and light filled five bedroom, four bath island r...

  • 5 Beds
  • 4 Baths
  • 202611449 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 35 DOM
917 Iiwi Street, Honolulu image
917 Iiwi Street, Honolulu $5,795,000

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
  • 35 DOM
1603 D Paula Drive, Honolulu image
1603 D Paula Drive, Honolulu $1,598,000 ▼

“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, i...

  • 5 Beds
  • 3 Baths
  • 202611410 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 38 DOM
559 Moaniala Street, Honolulu image
559 Moaniala Street, Honolulu $3,400,000

Welcome to 559 Moaniala Street, located in the prestigious gated community of The Pointe within Hawaii Loa Ridge for double the security gates and maximum protection. Thi...

  • 5 Beds
  • 5 Baths
  • 202611789 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 38 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
  • 39 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 Status
  • FS - Fee Simple Tenure
  • 39 DOM
6015 Kalanianaole Highway, Honolulu image
6015 Kalanianaole Highway, Honolulu $13,800,000

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
  • 41 DOM
950 Kealaolu Avenue, Honolulu image
950 Kealaolu Avenue, Honolulu $6,200,000

Luxury Kahala Living at Its Finest! This stunning custom residence blends timeless elegance with modern island comfort in one of Honolulu’s most prestigious neighborhoods...

  • 5 Beds
  • 6 Baths
  • 202611466 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 42 DOM
852 Kainoa Place, Honolulu image
852 Kainoa Place, Honolulu $3,340,000 ▼

Thoughtfully reimagined and beautifully appointed, the 2026 open-concept estate blends Hawaiian-inspired finishes with refined contemporary luxury, creating the ambiance ...

  • 5 Beds
  • 4 Baths
  • 202611527 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 44 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
  • 6 Baths
  • 202611278 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 48 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
  • 49 DOM
4561 Aukai Avenue, Honolulu image
4561 Aukai Avenue, Honolulu $10,500,000

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
  • 52 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
  • 52 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
  • 53 DOM
2505 Saul Place, Honolulu image
2505 Saul Place, Honolulu $2,650,000 ▼

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
  • 62 DOM
2505 Peter Street, Honolulu image
2505 Peter Street, Honolulu $1,050,000 ▼

Excellent location high atop St. Louis Heights with spectacular City, Diamond Head and Ocean views! Located near schools, shopping centers, beaches, parks, hiking, minute...

  • 5 Beds
  • 2 Baths
  • 202610171 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 63 DOM
907 Ahuwale Street, Honolulu image
907 Ahuwale Street, Honolulu $1,800,000

Perched above Aina Haina with sweeping valley, mountain, and ocean views, this remodeled 5-bedroom, 3-bath residence offers a surprising sense of space, light, and privac...

  • 5 Beds
  • 3 Baths
  • 202610065 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 66 DOM
218 Kaalawai Place, Honolulu image
218 Kaalawai Place, Honolulu $17,500,000

This magnificent Diamond Head “Cove Area” beachfront masterpiece harmoniously fuses traditional Hawaiian architectural elements with an open modern lifestyle floorplan. L...

  • 5 Beds
  • 7 Baths
  • 202609193 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 80 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
  • 98 DOM
4504 Kahala Avenue, Honolulu image
4504 Kahala Avenue, Honolulu $6,998,000

This home is an exceptional buy for the Kahala market. Priced below replacement cost for this INCREDIBLE & RARE to see craftsmanship! Completed in 1993 & built from quali...

  • 5 Beds
  • 8 Baths
  • 202607760 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 98 DOM
4347 Pahoa Avenue, Honolulu image
4347 Pahoa Avenue, Honolulu $3,780,000 ▼

House of Bird of Paradise - a wonderful oasis in prestigious Kahala. Grand scale interior of over 6,000sq ft, 5 spacious bedrooms and the possibility to make 6th bedroom ...

  • 5 Beds
  • 5 Baths
  • 202606734 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 116 DOM
928 9th Avenue Unit C, Honolulu image
928 9th Avenue Unit C, Honolulu $1,598,000

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
  • 117 DOM
928 9th Avenue Unit B, Honolulu image
928 9th Avenue Unit B, Honolulu $1,580,000 ▼

Location, location, location! Welcome home! This beautifully designed home located in highly desirable Kaimuki, quiet located with city view. Convenient to school, shops....

  • 5 Beds
  • 3 Baths
  • 202605213 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 140 DOM
1834 St Louis Drive, Honolulu image
1834 St Louis Drive, Honolulu $1,400,000

The Giving House - A truly rare offering on highly desired St. Louis Drive in Honolulu. Commanding sweeping ocean views from its prized east-west orientation, this except...

  • 5 Beds
  • 4 Baths
  • 202605116 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 143 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
  • 148 DOM
213 Kaalawai Place, Honolulu image
213 Kaalawai Place, Honolulu $26,500,000

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
  • 166 DOM
1732-A Mikahala Way, Honolulu image
1732-A Mikahala Way, Honolulu $2,495,000

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...

  • 5 Beds
  • 7 Baths
  • 202602181 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 175 DOM
2550 Ipulei Way, Honolulu image
2550 Ipulei Way, Honolulu $1,099,000 ▼

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...

  • 5 Beds
  • 2 Baths
  • 202600101 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 201 DOM
4240 Kaikoo Place, Honolulu image
4240 Kaikoo Place, Honolulu $6,995,000 ▲

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 mas...

  • 5 Beds
  • 6 Baths
  • 202528401 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 211 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
  • 217 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
  • 220 DOM
4366 Royal Place, Honolulu image
4366 Royal Place, Honolulu $8,875,000

RARE OCEAN ADJACENT ESTATE ON ROYAL PLACE. Between Royal Place and Kahala Avenue lies an extraordinary estate offering privacy, space & refined coastal living just moment...

  • 5 Beds
  • 6 Baths
  • 202525308 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 224 DOM
3455A Wela Street, Honolulu image
3455A Wela Street, Honolulu $1,200,000 ▼

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...

  • 5 Beds
  • 3 Baths
  • 202524992 MLS
  • ACTIVE UNDER CONTRACT Status
  • FS - Fee Simple Tenure
  • 252 DOM
3735- Diamond Head Road, Honolulu image
3735- Diamond Head Road, Honolulu $43,000,000

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,...

  • 5 Beds
  • 7 Baths
  • 202520630 MLS
  • ACTIVE Status
  • FS - Fee Simple Tenure
  • 298 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
  • 488 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.

Looking to buy a 5 Bedroom Homes For Sale in Diamond Head in Diamond Head, HI?

Browse current 5 Bedroom Homes For Sale in Diamond Head. Can't find a home that fits your needs? Try our Advanced Oahu MLS search. You can easily filter properties by location, price, amenities, and more to find exactly what you're looking for.

Your VA Loan Benefits

Use your VA Loan Benefits

Search All Oahu Real Estate

Use our full MLS search to access all Oahu listings

Your Oahu Home Value

Our expert Oahu Realtors know your home's value like no one else

Like or Share

Popular Areas

  • Diamond Head
  • North Shore
  • Central Oahu
  • Leeward Coast
  • Windward Coast
  • Ewa Beach
  • Kapolei
  • Mililani
  • Kakaako
  • Kailua
  • Kaneohe
  • Haleiwa
  • Waianae
  • Aiea Heights
  • Pearl City
  • Aiea
  • Salt Lake
  • Newtown
  • Wahiawa
  • Waipahu

Search By Price

  • $100,000 - $200,000
  • $200,000 - $300,000
  • $300,000 - $400,000
  • $400,000 - $500,000
  • $500,000 - $600,000
  • $600,000 - $700,000
  • $700,000 - $800,000
  • $800,000 - $900,000
  • $900,000 - $1,000,000
  • Over $1,000,000

Search By Home Type

  • 1 Story
  • 2 Story
  • 3 Story
  • 3 Bedroom
  • 4 Bedroom
  • 5 Bedroom
  • 6 Bedroom
  • Acreage
  • Beachfront Homes
  • Condos
  • Golf Course Homes
  • Homes With Land
  • Homes With Pool
  • Lakefront Homes
  • Luxury Homes
  • Mountain View Homes
  • Multi-Family Homes
  • New Homes
  • Oceanfront Homes
  • Oceanview Homes
  • Single-Family
  • Townhouse
  • Waterfront Homes
  • Home
  • Selling
  • Buying
  • VA Home Loans
  • About Us
  • Contact Us
Create an Account

Create an Account 🏡

All access to the newest listings to hit the market, 100% free. We are always here to help in case you have questions!

  • See local listings faster than any real estate website
  • Access to a local agent that will help answer any of your questions
  • Get help buying and selling with us
  • And of course, our home search service is always 100% free!

Hello, 👋

Welcome back. We have new listings for you. Remember like always, we are always here to help. Happy house hunting!

My Favorites My Saved SearchesMessage my agent
Buy

Buy

Create a bullet proof buying plan by working with the best agents in the area. From planning, pre-approvals, tours, to getting your keys.

Sell

Sell

Get your home sold for the most money, in the least amount of time. It is never too early to devise a gameplan.

Create an Account

Home Estimate

See what your property is currently worth within seconds. Just enter your address.

compass logo
Sitemap
  • Home
  • About us
  • VA Loan Resources
  • PCS Resources
  • Home Search
  • Let's Connect
Contact

Get to Know Me

(808) 554-9667

Address

4211 Waialae Ave. Suite H-8

Honolulu, HI 96816

Kahala Mall



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.

REALTOR, ABR, e-Pro, MRP, CRS

Website designed and developed by Vanity Geeks.
  • l
  • l
  • l
  • l

© Copyright 2022 | Privacy Policy

  • Map Search
  • Advanced Search
IDX Real Estate Websites by
, an FNF RE Tech Company • Accessibility • Terms • Privacy