Diamond Head Homes with Oceanfront Frontage

Welcome to Diamond Head, a breathtaking gem nestled on the southeastern coast of Oahu, Hawaii. This iconic landmark is not just a stunning volcanic crater; it’s a vibrant community that offers a unique blend of natural beauty, rich history, and modern conveniences. With its proximity to Honolulu, Diamond Head provides residents with easy access to urban amenities while maintaining the tranquil allure of island living.

One of the most sought-after features of homes in Diamond Head is their oceanfront frontage. Imagine waking up every morning to the soothing sounds of waves crashing against the shore and enjoying panoramic views of the sparkling Pacific Ocean right from your window. The oceanfront properties here are more than just homes; they’re an invitation to a lifestyle filled with outdoor adventures, from surfing and snorkeling to hiking the famous Diamond Head Trail, which offers breathtaking vistas of the coastline.

Living in Diamond Head means being part of a close-knit community that cherishes its natural surroundings. The area is dotted with lush parks, pristine beaches, and scenic walking paths, perfect for morning strolls or sunset picnics. As a resident, you’ll also have the chance to experience the rich cultural tapestry of Honolulu, with its array of dining, shopping, and entertainment options just a short drive away.

Whether you’re looking for a peaceful retreat or an active lifestyle, Diamond Head’s oceanfront homes provide the perfect backdrop for your Hawaiian dream. Embrace the beauty, the community, and the unparalleled ocean views that make this region truly special. Welcome home to Diamond Head!

Newest Diamond Head Homes with Oceanfront 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

$50,000

2 Beds ⋅ 2 Baths ⋅ 202615775 MLS ⋅ LH - Leasehold Tenure ⋅ 3 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 ⋅ 17 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 ⋅ 17 DOM

Affectionately, known as 'Hotel Aloha,' a masterpiece of opulence, grace, and 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 saltwater pool, spa, & the vast Pacific Ocean—perfect for watching the surf & magenta sunsets. For added convenience, a gracious bedroom with an easy-access walk-in shower is located on the main level. The home showcases exquisite craftsmanship, featuring imported marble flooring and a matching fireplace. The gourmet kitchen includes gas cooking, while the media room offers a surround sound system. Exterior highlights include a newly painted automatic gated entry, lushly landscaped grounds & ample parking w/a two-car garage, a tiled driveway for 4 vehicles and space for a boat. Located off a private, crescent-shaped road shared by only three homes, this property offers unmatched security and privacy. Additional features: dual washer/dryer sets, central AC and direct beach access. Heated saltwater pool.

5599 Kalanianaole Highway, Honolulu

$150,000

2 Beds ⋅ 2 Baths ⋅ 202614285 MLS ⋅ LH - Leasehold Tenure ⋅ 24 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 ⋅ 24 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 ⋅ 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

$3,590,000

2 Beds ⋅ 2 Baths ⋅ 202613818 MLS ⋅ FS - Fee Simple Tenure ⋅ 34 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 ⋅ 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

$445,000

1 Baths ⋅ 202612484 MLS ⋅ FS - Fee Simple Tenure ⋅ 50 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

$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

$4,950,000

5 Beds ⋅ 5 Baths ⋅ 202606798 MLS ⋅ FS - Fee Simple Tenure ⋅ 63 DOM

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 setting work together. Thoughtfully remodeled with a contemporary design sensibility, every detail has been considered and every space elevated. The open plan kitchen anchors the main living area with a large island, upgraded appliances, and a flow that makes it as comfortable for quiet mornings as it is for entertaining. Generous lanai space leads to the lawn and the ocean beyond. Morning coffee with the sunrise over the Pacific, afternoon barbecues on the lawn with the water right in front of you. The second-floor primary suite is designed to maximize the setting. Ocean and mountain views from the primary bedroom, ocean views from the bath, and a dedicated space that works equally well as a home office or art studio, all facing the water. Five bedrooms, four full baths, and a half bath across 3,300 square feet of living on 8,674 square feet of fee simple land. The first floor includes a full bedroom suite. A pool provides a private retreat in back. Two-car garage. Photovoltaic owned. Direct ocean access.

5811 Kalanianaole Highway, 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.