Diamond Head Homes with Waterfront Frontage

Welcome to Diamond Head, an iconic gem nestled on the southeastern coast of Oahu, Hawaii. Renowned for its breathtaking views and lush landscapes, this vibrant neighborhood seamlessly blends natural beauty with a rich cultural heritage. Towering above the shoreline, the famous Diamond Head Crater serves as a stunning backdrop, offering residents and visitors alike a picturesque setting that is truly unparalleled.

Living in Diamond Head means embracing a lifestyle defined by the tranquil rhythm of island life. With pristine beaches just a stone's throw away, homeowners can indulge in sun-soaked days spent swimming, surfing, or simply lounging on the golden sands. The area is also a paradise for outdoor enthusiasts, featuring an array of hiking trails that lead to spectacular lookout points, showcasing panoramic vistas of the Pacific Ocean and the Waikiki skyline.

For those seeking homes with waterfront frontage, Diamond Head presents an enticing opportunity. Imagine waking up to the gentle sound of waves lapping against the shore, with your own slice of paradise right outside your door. These waterfront properties offer not only stunning ocean views but also direct access to the beach, allowing for spontaneous seaside adventures and evening strolls under the stars.

In addition to its natural allure, Diamond Head is conveniently located near the vibrant heart of Honolulu, where you can explore a diverse array of dining, shopping, and cultural experiences. Whether you’re a first-time buyer or looking to invest in a luxurious second home, Diamond Head’s waterfront offerings are sure to captivate your heart and elevate your lifestyle. Discover the beauty and charm of Diamond Head today, and make your dream of island living a reality!

Newest Diamond Head Homes with Waterfront Frontage

$125,000

2 Beds ⋅ 2 Baths ⋅ 202616172 MLS ⋅ LH - Leasehold Tenure ⋅ 1 DOM ⋅ Kahala Beach BLDG.

Enjoy coastal chic living in this well-appointed and cared for Kahala Beach residence located one back from the ocean. A rare offering in the preferred building (three stack), enjoy beautiful views of the Pacific Ocean from your lanai. Updated in 2021 with refreshed carpet, tasteful decor and well thought out upgrades that show pride of ownership. Two parking stalls included, both located in your building'sgarage. Property is Leasehold and no fee purchase option is available. Please consult with your Realtor to ensure You are fully aware of what Leasehold ownership entails at Kahala Beach Apartments. Monthly fees (estimated, please confirm) are: $2,565/month in Lease Rent, $1,371.31/month in Maintenance Fees and $863.43/mo nth in Property Taxes. Leasehold expires on July 15th 2027, no lease renewal or extension will occur. Owners will have the option to sign a rental lease agreement with Lessor after the leasehold expires, but with an initial contract date no longer than July 31st, 2028.

4999 Kahala Avenue Unit 250, Honolulu

$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

$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

$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 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 heated 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 & 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 vehicles and space for a boat. Located off a private, crescent-shaped road shared by only 3 homes, this property offers unmatched security and privacy. Additional features: 2 W/Ds, central AC, Steam room, direct Beach access, painted inside & out and pre-listing home inspection completed!

5599 Kalanianaole Highway, 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

$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

$1,099,000

1 Beds ⋅ 1 Baths ⋅ 202611458 MLS ⋅ FS - Fee Simple Tenure ⋅ 62 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

$13,800,000

5 Beds ⋅ 7 Baths ⋅ 202611456 MLS ⋅ FS - Fee Simple Tenure ⋅ 70 DOM

The Paiko Retreat stands as a true Architectural Masterpiece after a comprehensive restoration. Sitting on over an acre of mature landscaping, Kanewai Spring, waterfalls, and koi ponds, there’s no place quite like this home. A unique estate designed by John Hara in 1983, Hara brings an intentional, open-air feeling to this home like he built at the Honolulu Museum of Art, UH West Oahu, and Punahou School. Spanning 9,295 square feet, the interior is vast, yet warm and deliberate. A dedicated primary wing and private sitting room tucked away from the main entertaining areas, plus four guest bedrooms, each with its own ensuite bath and connected by a custom glass elevator. A media room, family room, and private offices provide space for everyone. The transition to the sweeping lanais is seamless. The grounds carry the calm of a private Japanese resort, with gardens and water features weaving through the property. You have direct frontage on Kanewai Spring feeding into Historic Paiko Lagoon. Because it’s a state wildlife sanctuary, the view is strictly nature—quiet and serene. Evenings here are best spent on the lanai watching shorebirds wade through the shallow waters.

6015 Kalanianaole Highway, Honolulu

$2,198,000

202611507 MLS ⋅ FS - Fee Simple Tenure ⋅ 74 DOM

The only BEACH FRONT VACANT LAND, in EAST HONOLULU, OAHU with more than 65 linear feet of sandy beach fronting famous surfing spots Toes and Secrets currently available UNDER $15,000,000. Paiko Beach consists of only 22 residences that are beach front. Priced $1,024,500 BELOW TAX ASSESSED VALUE! Endless water activities are made possible by the barrier reef creating a calm and protected sandy beach front. Seller has obtained APPROVED SHORELINE CERTIFICATION (see listing supplements) 21 feet forward (towards the ocean) of the property line. With all setbacks considered, this property still has a buildable footprint area of more than 4,290 square feet for a single level home! More if you build a second story. Seller has attached and completed the K2 Standard Survey, Shoreline Certification Survey and Topo Map. No Easements or Encroachments. Also listed in MLS under Land Listing MLS #202611508

240 Paiko Drive, Honolulu

$2,198,000

202611508 MLS ⋅ FS - Fee Simple Tenure ⋅ 74 DOM

240 Paiko Drive, Honolulu

$1,975,000

2 Beds ⋅ 1 Baths ⋅ 202610368 MLS ⋅ FS - Fee Simple Tenure ⋅ 85 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

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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.