Diamond Head Homes with Oceanfront Frontage

Welcome to Diamond Head, a stunning gem nestled on the southeastern coast of Oahu, Hawaii. Known for its iconic volcanic crater and breathtaking ocean views, this enchanting neighborhood in Honolulu offers a unique blend of natural beauty and vibrant culture. With its lush landscapes, pristine beaches, and rich history, Diamond Head is not just a place to live; it’s a lifestyle that embraces the spirit of aloha.

Homes in Diamond Head boast oceanfront frontage, providing residents with unparalleled access to the sparkling waters of the Pacific Ocean. Imagine waking up to the soothing sound of waves crashing against the shore and stepping out onto your lanai to witness the sun rising over the horizon. These properties are designed for those who appreciate the finer things in life, offering luxurious amenities, spacious interiors, and outdoor spaces perfect for entertaining or simply soaking in the breathtaking views.

Beyond the stunning homes, Diamond Head is a paradise for outdoor enthusiasts. With hiking trails that lead to panoramic vistas, world-class surfing spots, and serene beaches like Kaimana Beach and Queen's Surf Beach, adventure awaits at every turn. The neighborhood is also home to a vibrant community, featuring local shops, delightful eateries, and cultural landmarks that reflect the rich heritage of Hawaii.

Whether you’re seeking a permanent residence or a vacation getaway, Diamond Head offers a rare opportunity to experience oceanfront living in one of the most picturesque settings in the world. Discover your slice of paradise in Diamond Head, where every day feels like a vacation.

Newest Diamond Head Homes with Oceanfront Frontage

$425,000

1 Baths ⋅ 202615447 MLS ⋅ LH - Leasehold Tenure ⋅ 4 DOM ⋅ Sans Souci Inc BLDG.

Living at Sans Souci is all about the lifestyle: enjoying the coveted Gold Coast. You wake up to the sound of the ocean while enjoying the swaying palm trees right outside your lanai. Beautiful sunsets and Friday night fireworks. You're only steps to Sans Souci beach, which is a buzz of activities, join in or sit on your lanai and enjoy the resort like atmosphere. Located across from Kapiolani Park and a short walk to Waikiki, Honolulu Zoo, the Aquarium and the Shell amphitheater. Also in the neighborhood is the Elks Lodge and Outrigger Canoe Club. Beachside dining at Michel's, Hau Tree Lanai or a little casual dining at the Barefoot Beach Cafe. Spend Saturday mornings at the KCC Farmers market or hike up scenic Diamond Head. Property to be sold AS-IS.

2877 Kalakaua Avenue Unit 502, Honolulu

$48,000

2 Beds ⋅ 2 Baths ⋅ 202615328 MLS ⋅ LH - Leasehold Tenure ⋅ 4 DOM ⋅ Kahala Beach BLDG.

NEW LISTING!! Experience island living in this beautifully upgraded 2 bdrm/2 bath residence in the desirable Kahala Beach oceanfront community. Tastefully renovated with modern finishes throughout, the unit features vinyl plank flooring, an updated kitchen with stainless steel appliances, and refreshed bathrooms. The spacious enclosed, covered lanai provides a comfortable extension of the living space—perfect for relaxing or enjoying the lush surroundings. The generously sized primary bedroom offers a peaceful retreat, while the unit’s private setting is enhanced by abundant greenery. A wonderful opportunity to enjoy the tranquility of Kahala Beach with the convenience of being just minutes from Kahala Mall with options of restaurants, shopping and entertainment! Don’t miss this fantastic opportunity!

4999 Kahala Avenue Unit 202, Honolulu

$985,000

1 Baths ⋅ 202614438 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 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

$50,000

2 Beds ⋅ 2 Baths ⋅ 202615775 MLS ⋅ LH - Leasehold Tenure ⋅ 8 DOM ⋅ Kahala Beach BLDG.

Enjoy the beauty and serenity of Kahala Beach from this spacious 1,555 sq ft, 2-bedroom, 2-bathroom ground-floor condominium at Kahala Beach Apartments. Ideally located on Kahala Avenue, this fully furnished residence is just steps from the beach and conveniently close to Kahala Hotel, Kahala Mall, restaurants, shopping, and easy access to Honolulu. The generous floor plan features an enclosed lanai that expands the living space and offers a peaceful garden setting. The unit is fully furnished with comfortable Hawaiian-style décor and includes a king bed in the primary bedroom, two queen beds in the second bedroom, and two sofa beds, providing ample space for family and guests. Enjoy the convenience of ground-floor living with easy access to the pool and recreation areas, plus the ability to bypass the elevator. The property also includes one covered garage parking stall and storage. A unique opportunity to own in one of Honolulu’s desirable beachfront communities. The lease term ends July 2027, but you can rent from Kamehameha schools after providing additional time to enjoy or utilize the property. Maintenance fee includes all utilities. Lease rent paid til October 2026!

4999 Kahala Avenue Unit 148, Honolulu

$5,750,000

6 Beds ⋅ 6 Baths ⋅ 202614908 MLS ⋅ FS - Fee Simple Tenure ⋅ 22 DOM

TIMELESS ISLAND LIVING ON WAILUPE BEACH WITH SEPARATE GUEST HOUSE. Set on a 25,216 sq ft beachfront parcel w/approx 90 linear ft of sandy shoreline, this charming, reimagined island beach house features a 3-bdrm, 3-bath main residence, a 3-bdrm, 2-bath guest house & detached pool house w/indoor swimming pool & full bath. Coconut palms, mature tropical landscaping, expansive lawns & outdoor gathering areas lead to the sandy shoreline. The main home features French windows, spacious open living & lounge areas w/seamless indoor/outdoor living. Wraparound decks overlook tropical gardens & ocean vistas. The kitchen features rich coastal blue-green cabinetry, abundant counter space, dine-in seating & ocean views. Three en-suite bdrms each offer a private bath w/updated vanities, while a separate seaside den serves as a home office w/lovely views. The detached guest house is situated above two separate 2-car garages w/ generous storage, laundry facilities & ample driveway parking. Enjoy surfing, paddleboarding, kayaking, swimming & beach walks just beyond your backyard. Conveniently located between Kahala & Aina Haina w/easy access to shopping, dining, banking & everyday conveniences.

4929 Kalanianaole Highway, Honolulu

$7,000,000

5 Beds ⋅ 7 Baths ⋅ 202614361 MLS ⋅ FS - Fee Simple Tenure ⋅ 22 DOM

Affectionately, known as 'Hotel Aloha,' a masterpiece of opulence, grace & authentic Hawaiian design. This elegant 2-story private residence features 5 spacious en-suite bedrooms, each offering a private luxury bathroom, generous closet space & breathtaking views. Located on a white sandy beach in East Honolulu The upstairs primary suite opens to a sprawling lanai overlooking the heated saltwater pool, spa & the vast Pacific Ocean—perfect for watching the surf & magenta sunsets. For added convenience, a gracious bedroom w/an easy-access walk-in shower is located on the main level. The home showcases exquisite craftsmanship, featuring imported marble flooring & matching fireplace. The gourmet kitchen includes gas cooking. The media room offers a surround sound system. Exterior highlights: automatic gated entry, lushly landscaped grounds & ample parking w/a two-car garage, a tiled driveway for 4 cars & space for a boat. Located off a private, crescent-shaped road shared by only 3 homes, this property offers security & privacy. Additional features: 2 W/Ds, central AC, Steam room & direct Beach access. The pre-listing home inspection completed! Sold fully furnished! Sunday Open 12-4pm

5599 Kalanianaole Highway, Honolulu

$150,000

2 Beds ⋅ 2 Baths ⋅ 202614285 MLS ⋅ LH - Leasehold Tenure ⋅ 29 DOM ⋅ Kahala Beach BLDG.

This spacious, garden-view gem in prestigious Kahala is beautifully renovated and move-in ready! Featuring 2 bedrooms, 2 baths, 1 covered parking stall, an open floor plan, and an enclosed lanai, this home is just steps from a sandy beach, Kahala Mall, and the iconic Kahala Hotel. Enjoy direct beach access with a protective offshore reef, offering calm waters for swimming, snorkeling, diving, and paddleboarding. Experience the best of island living. Lease expires July 15, 2027.

4999 Kahala Avenue Unit 422, Honolulu

$495,000

3 Beds ⋅ 3 Baths ⋅ 202614329 MLS ⋅ LH - Leasehold Tenure ⋅ 29 DOM ⋅ Kahala Beach BLDG.

Experience luxury BEACHFRONT living in prestigious KAHALA! This stunning 3b/3b residence offers direct beach access w/a protective offshore reef, creating calm waters ideal for swimming, snorkeling, diving & paddleboarding. Enjoy unobstructed OCEAN & KOKO HEAD views from the spacious enclosed lanai. Highlights incl: HARDWOOD floors, soaring ceilings, custom cabinetry, central A/C, Sub-Zero & Bosch appliances, wine refrigerator, built-in bookshelves & speakers, Toto toilets, dual water heaters & Water Guard sensors. Rare opportunity to own this beachfront paradise! Lease expires July 15, 2027.

4999 Kahala Avenue Unit 472, Honolulu

$12,500,000

5 Beds ⋅ 4 Baths ⋅ 202613905 MLS ⋅ FS - Fee Simple Tenure ⋅ 36 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

$3,590,000

2 Beds ⋅ 2 Baths ⋅ 202613818 MLS ⋅ FS - Fee Simple Tenure ⋅ 39 DOM ⋅ Coral Strand Ltd BLDG.

Experience refined Gold Coast living in this beautifully crafted oceanfront residence at Coral Strand Ltd. Perfectly positioned above the canopy of Kapiolani Park, this exceptional home captures breathtaking panoramic views of the Pacific Ocean, Diamond Head, the Honolulu skyline from three private lanais. Expertly remodeled by renowned contractor John Sutton, the residence showcases timeless design, exceptional craftsmanship, and premium materials throughout. European limestone flooring, exquisite marble bathrooms, hand-finished teak accents, custom walnut cabinetry, and soaring 9-foot ceilings create an elegant and sophisticated living environment. The gourmet kitchen is appointed with Miele, Bosch, and Sub-Zero appliances, while a wet bar, Lutron lighting and automated shades, Sonos sound system, dual-zone central air conditioning, and an in-unit washer and dryer provide modern comfort and convenience. Residents enjoy secure underground parking, private storage, a heated saltwater pool, and direct access to one of Oahu's most desirable coastal settings. Just moments from Kapiolani Park, Waikiki and world-famous beaches, this is island living at its finest.

2979 Kalakaua Avenue Unit 904, Honolulu

$995,000

1 Beds ⋅ 1 Baths ⋅ 202613177 MLS ⋅ FS - Fee Simple Tenure ⋅ 42 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

$445,000

1 Baths ⋅ 202612484 MLS ⋅ FS - Fee Simple Tenure ⋅ 55 DOM ⋅ Diamond Head Ambassador B BLDG.

Welcome to Diamond Head Ambassador, where island living meets an unbeatable location on Oahu's prestigious Gold Coast! Just minutes from world-famous Waikiki Beach, this inviting residence offers the perfect opportunity to own your own piece of paradise. Start your mornings with a cup of coffee on your private lanai while enjoying peekaboo views of the Pacific Ocean and Kapi?olani Park. Residents enjoy a beautifully renovated saltwater pool, secured storage, and convenient bike and surfboard racks—ideal for embracing Hawaii's outdoor lifestyle. Endless recreation awaits just outside your door: swimming, surfing, snorkeling, biking, jogging, & hiking the iconic Diamond Head trail. Stroll to the KCC Farmers Market, attend concerts at Kapi?olani Park, or spend the day at the Honolulu Zoo, Waikiki Aquarium, Outrigger Canoe Club, or Elks Lodge. An abundance of popular restaurants, cafés, and shopping are all within easy reach. Grab your beach chair & head to the shoreline to experience Hawaii's spectacular sunsets. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this exceptional location offers the very best of the Gold Coast lifestyle.

2957 Kalakaua Avenue Unit 211, 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.