Diamond Head Homes with Waterfront Frontage

Welcome to Diamond Head, a breathtaking gem nestled along the southern coast of Oahu, Hawaii. Renowned for its iconic volcanic crater and stunning coastal views, this enchanting neighborhood offers a unique blend of natural beauty and vibrant community life. Just a stone's throw away from the bustling heart of Honolulu, Diamond Head is perfectly positioned for those seeking both tranquility and accessibility.

As you meander through the palm-lined streets of Diamond Head, you'll discover a variety of charming homes, many of which boast coveted waterfront frontage. Imagine waking up to the gentle sound of waves lapping against the shore, with panoramic views of the Pacific Ocean right from your window. These waterfront properties provide a rare opportunity to experience the beauty of island living at its finest, where every sunset becomes a private masterpiece.

The neighborhood is not just about picturesque homes; it also offers a rich tapestry of outdoor activities. From hiking the famous Diamond Head Crater Trail to enjoying leisurely strolls along the sandy beaches, residents are never far from adventure. The nearby Kapiolani Park invites picnics, sports, and community events, fostering a sense of camaraderie among neighbors.

With its unique blend of natural beauty, vibrant culture, and stunning waterfront properties, Diamond Head is more than just a place to live; it’s a lifestyle. Whether you’re looking to invest in a serene retreat or a lively community, Diamond Head promises an unmatched living experience in paradise. Come and discover the magic of this extraordinary neighborhood!

Newest Diamond Head Homes with Waterfront Frontage

$985,000

1 Baths ⋅ 202614438 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM ⋅ Colony Surf Ltd BLDG.

Welcome to this spacious and well maintained studio at Colony Surf. One of a handful condos situated directly on the sandy beach in Oahu's premier Gold Coast. Bright and breezy with ocean and Diamond Head views. Newly painted. No popcorn ceiling. Enjoy Michel's Restaurant located in the lobby with oceanfront dining. Walking distance to Waikiki, dining, Waikiki Aquarium, Honolulu Zoo, and Kapiolani Park. Maintenance fee includes all utilities - electricity, water, sewer, trash, gas, cable TV and Internet. Pet friendly.

2895 Kalakaua Avenue Unit 1008, Honolulu

$12,500,000

5 Beds ⋅ 4 Baths ⋅ 202613905 MLS ⋅ FS - Fee Simple Tenure ⋅ 31 DOM

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 presents a rare opportunity to own in one of Oahu's most iconic oceanfront enclaves. Situated on a 15,398 sq ft parcel, the home enjoys spectacular unobstructed ocean views, rolling surf, swaying coconut palms & the soothing sounds of the Pacific from an exceptionally private setting. A welcoming courtyard w/ tropical landscaping & signature plumeria tree leads to light-filled interiors w/ vaulted ceilings & an open floor plan showcasing the sparkling azure waters of the Pacific. Expansive living & dining areas flow seamlessly to the oceanfront lanai, grassy seaside lawn, and steps to the water's edge. The kitchen features granite countertops, abundant cabinetry, dine-in seating & a breakfast nook. The oceanfront primary suite enjoys breathtaking views & spa like bath. Four additional bedrooms offer flexibility for family/guests or office. Conveniently located near Kapiolani Park, Diamond HD hiking trails, golf, Farmers Market, Waikiki, restaurants & shopping. A truly rare opportunity to own on Diamond Head Beach.

3735 C Diamond Head Road, Honolulu

$995,000

1 Beds ⋅ 1 Baths ⋅ 202613177 MLS ⋅ FS - Fee Simple Tenure ⋅ 37 DOM ⋅ Diamond Head Ambassador C BLDG.

Live the Gold Coast dream at the iconic Diamond Head Ambassador! This desirable 1-bedroom, 1-bathroom residence places you steps away from world-class surf, pristine beaches, and the beauty of Kapiolani Park. Enjoy the building's signature mid-century design, unique Japanese-inspired footbridges, and an incredible oceanfront backyard compete with a saltwater pool, private ocean stairs and outdoor shower. An unbeatable location close to the Elks Club, Outrigger Canoe Club, and Waikiki. This co-op property is your perfect boutique oceanfront getaway.

2957 Kalakaua Avenue Unit 318, Honolulu

$1,099,000

1 Beds ⋅ 1 Baths ⋅ 202611458 MLS ⋅ FS - Fee Simple Tenure ⋅ 57 DOM ⋅ Tropic Seas Inc BLDG.

Perched on the 7th floor of the Tropic Seas Inc., this corner residence offers an elevated coastal retreat with gorgeous ocean vistas & treetop mountain views. Renovated in 2014, the unit blends modern comfort with timeless beachside elegance, featuring smooth ceilings, natural stone flooring, and floor-to-ceiling windows and sliding glass doors that invite abundant natural light and steady tradewinds from the mauka to makai exposure. A generous ocean facing lanai extends the living space outdoors—an ideal perch to watch surfers, paddlers, and sailboats glide by, along with the occasional honu or monk seal in the turquoise water below. The open layout includes a kitchen with newer cabinetry, granite countertops, stainless appliances, and thoughtful storage. The bedroom offers 2 closets, including a custom wall closet with sliding glass doors and built-in organization.Two dedicated storage spaces, including 1 on the same floor, plus surfboard and bike storage all add exceptional convenience. Residents enjoy private ocean access, a rare oceanfront BBQ and lounge area, gated entry, and an on-site manager. Enjoy Gold Coast living in one of Honolulu’s most coveted oceanfront enclaves!

2943 Kalakaua Avenue Unit 707, Honolulu

$2,175,000

2 Beds ⋅ 1 Baths ⋅ 202610368 MLS ⋅ FS - Fee Simple Tenure ⋅ 80 DOM ⋅ Tahitienne Inc BLDG.

Wake up to the sound of the surf and enjoy golden sunsets from this direct oceanfront two-bedroom residence at the iconic Tahitienne on Diamond Head’s coveted Gold Coast. Framed by swaying palms and endless blue water views, this rare retreat captures the essence of Hawaii coastal living. A spacious lanai invites morning coffee overlooking the surf, whale watching in season, and evenings spent watching the sun melt into the Pacific. Inside, hand-crafted custom woodwork brings warmth, artistry, and timeless island character to the home, creating a refined yet relaxed atmosphere. Expansive ocean views fill the living spaces, while the intimate boutique setting offers privacy and tranquility just moments from Waikiki. Ideally positioned at the base of Diamond Head, the Gold Coast lifestyle is unlike anywhere else on Oahu — surf and paddle boarding out front, ocean swims at Kaimana Beach, sunset walks through Kapiolani Park, and nearby dining and nightlife all within minutes. A rare opportunity to enjoy front-row oceanfront living in one of Honolulu’s most treasured neighborhoods.

2999 Kalakaua Avenue Unit 404, Honolulu

$5,000,000

2 Beds ⋅ 3 Baths ⋅ 202609461 MLS ⋅ FS - Fee Simple Tenure ⋅ 94 DOM ⋅ Kainalu BLDG.

Awesome direct oceanfront double unit (combined 5B & 5C) at Kainalu offering panoramic views of crystal-clear waters where fish and coral are visible from your living room. From this 5th floor, enjoy front-row seats to multiple surf breaks filled with traditional longboarders and foil surfers, along with sailboats gliding across the horizon. Open the expansive wall of windows to welcome cooling trade winds and sweeping vistas stretching from Diamond Head to Waikiki and beyond. Whether dining or relaxing, breathtaking sunsets become part of everyday living in this spacious coastal retreat. The exceptional trophy residence features 2 bedrooms (could be three), 3 bathrooms, and 73 feet of beach/ocean frontage with access to a small private beach. Located in a quiet residential area just below DH on the Goldcoast with close proximity to Waikiki, Kapiolani Park, beaches, fine dining, shops & so much more! Additional highlights include air conditioning, elegant limestone flooring, a resident manager, and two covered secured parking stalls. Experience the best of oceanfront luxury island living.

2801 Coconut Avenue Unit 5 B/C, Honolulu

$17,500,000

5 Beds ⋅ 7 Baths ⋅ 202609193 MLS ⋅ FS - Fee Simple Tenure ⋅ 104 DOM

This magnificent Diamond Head “Cove Area” beachfront masterpiece harmoniously fuses traditional Hawaiian architectural elements with an open modern lifestyle floorplan. Located on a quiet lane off Diamond Head Road, this home is truly a treasure to behold. The grand reception areas lead out to extensive wraparound lanai areas, a covered grill space, and a beachside seating area—perfect for enjoying sunsets and drinks while taking in the endless views of the Pacific Ocean. The upper level boasts a large primary ocean view bedroom, two additional en-suite bedrooms, elevator, gas generator and an unmatched office with ocean views that you’ll never want to leave. Refreshing pool, lush private landscaping, and unmatched location, style, comfort, and distinction define this Diamond Head gem.

218 Kaalawai Place, Honolulu

$849,000

1 Baths ⋅ 202608523 MLS ⋅ FS - Fee Simple Tenure ⋅ 112 DOM ⋅ Colony Surf Ltd BLDG.

Welcome to Colony Surf 206, an iconic beachfront residence nestled on the slopes of Diamond Head. This charming studio condo captures the essence of classic Hawai‘i living with sweeping ocean views, majestic Diamond Head as your backdrop, and refreshing tradewinds flowing through the open layout. Designed with timeless island style, the unit offers easy, breezy living on one of Waikiki's best sandy beaches. Enjoy morning swims, surfing, paddling, sunset strolls, and dining at the nearby Kaimana Beach Hotel or Michel’s restaurant downstairs. Easy living with a low monthly fee that includes electricity, internet, and more. Located in a coveted Gold Coast setting, Colony Surf is where vintage charm meets relaxed elegance— this residence is an ideal retreat or pied-à-terre in paradise.

2895 Kalakaua Avenue Unit 206, Honolulu

$925,000

1 Beds ⋅ 1 Baths ⋅ 202607412 MLS ⋅ FS - Fee Simple Tenure ⋅ 114 DOM ⋅ Colony Surf Ltd BLDG.

Welcome to this well-maintained 1-bedroom, 1-bath residence in the iconic Colony Surf, an oceanfront landmark at the edge of Waikiki and Diamond Head. This light and bright unit features a separate bedroom, in-unit washer/dryer, and an open layout with refreshing trade winds. While it does not have a direct ocean view, it is just steps from the beach. Enjoy morning swims, surfing, and sunset strolls, with Kapiolani Park, shopping, and dining at Michel’s and the Kaimana Beach Hotel nearby. Low monthly fee includes electricity, internet, front desk service, parking stall, and more. A rare opportunity to own in one of Honolulu’s most sought-after Gold Coast buildings.

2895 Kalakaua Avenue Unit 207, Honolulu

$999,000

2 Beds ⋅ 2 Baths ⋅ 202607527 MLS ⋅ FS - Fee Simple Tenure ⋅ 128 DOM ⋅ Kainalu BLDG.

Experience timeless oceanfront living in this rare, spacious condo at the iconic Kainalu on Honolulu’s coveted Gold Coast. Located directly on a sandy beach at the base of Diamond Head, this light-filled residence offers peekaboo ocean views, cool tradewinds, and the soothing sound of waves just outside your window. The open layout features generous living and dining areas perfect for relaxing or entertaining. The second bedroom has been opened up to create an extra-large living area. The primary suite has an ensuite bath, while a second full bathroom provides added convenience. Enjoy exclusive access to a private sandy beach, surf at Tonggs, or unwind on the oceanfront lounge area. This secure, boutique building includes a coveted covered parking stall, easy walk up or elevator access, and a peaceful, quiet environment. Just minutes from Waikiki, Kapiolani Park, and the Outrigger Canoe Club, Kainalu offers the perfect blend of serenity and island lifestyle. A rare opportunity to own a spacious beachfront retreat in one of O'ahu’s most prestigious neighborhoods. Currently lived in as a one-bedroom but this residence is a 2/2 per county records.

2801 Coconut Avenue Unit 2D, Honolulu

$4,250,000

2 Beds ⋅ 2 Baths ⋅ 202607496 MLS ⋅ FS - Fee Simple Tenure ⋅ 128 DOM ⋅ Colony Surf Ltd BLDG.

Double the Views, Double the Space, Simply Fabulous. A rare offering at Colony Surf, this double-unit residence (Units 1404 & 1405) combines comfort, flexibility and oceanfront luxury on one of Oahu’s most iconic sandy beachfront settings. Perched high with side, corner, and ocean-facing orientation, the units capture sweeping views of the Pacific, Diamond Head & Waikiki’s coastline. Trade winds and rolling surf create a breezy, beachside ambiance throughout. Spacious interiors allow use as one grand residence or separate units. Upgraded with lovely kitchens & baths, built-in oceanfront seating, and expansive windows to take in those spellbinding sunset views. Enjoy daily beach walks or paddle sessions just outside your door. Explore nearby Kapiolani Park, the Zoo, and Aquarium. Dine downstairs at Michel’s or stroll to the Hau Tree Restaurant next door or one of Waikiki’s shops and cafés. Whether for beachfront living or investment potential, this is a rare opportunity in one of Honolulu’s most treasured coastal settings. Sales include TMK (1)3-1-032-010-0112 (Apt. 1404) and TMK (1)3-1-032-010-0113 (Apt. 1405).

2895 Kalakaua Avenue Unit 1404 & #1405, Honolulu

$1,350,000

1 Beds ⋅ 1 Baths ⋅ 202607191 MLS ⋅ FS - Fee Simple Tenure ⋅ 131 DOM ⋅ Diamond Head Ambassador C BLDG.

Wake up to panoramic ocean views from Diamond Head buoy to Waikiki. Watch the surf roll in at Tonggs, Rice Bowls, and Old Mans- right from your lanai. This classic Gold Coast corner unit blends charm, privacy, and comfort. Sip your morning coffee as the sun rises and wind down with sunset skies from your living room. Enjoy direct ocean access via the iconic silver stairs, plus lockable owner storage and a full-time resident manager. Close to Kapiolani Park, Outrigger Canoe Club, Elks Club, Kaimana Beach, and all that Waikiki has to offer. Diamond Head Ambassador offers the ultimate surf lifestyle.

2957 Kalakaua Avenue Unit 418, Honolulu

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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.