Diamond Head Homes with Waterfront Frontage

Welcome to Diamond Head, a stunning neighborhood nestled on the southeastern coast of Honolulu, Hawaii. Known for its iconic volcanic tuff cone, Diamond Head is not just a geological marvel; it’s a vibrant community that offers an unparalleled lifestyle amidst breathtaking natural beauty.

This picturesque neighborhood is renowned for its stunning ocean views and luxurious homes with waterfront frontage. Imagine waking up each day to the soothing sounds of the waves and the gentle breeze wafting through your windows. Whether you’re sipping coffee on your private lanai or enjoying a sunset stroll along the shoreline, life in Diamond Head is nothing short of idyllic.

The homes here are a perfect blend of modern elegance and tropical charm, featuring spacious layouts, lush landscaping, and direct access to the pristine beaches that line the coast. With a variety of architectural styles, from contemporary masterpieces to charming beach cottages, there’s a perfect property for everyone looking to embrace the island lifestyle.

Beyond the beautiful homes, Diamond Head is rich in activities and amenities. Residents enjoy easy access to world-class hiking trails, including the famous Diamond Head State Monument, which offers panoramic views of the Pacific Ocean and the vibrant city of Honolulu. The neighborhood is also home to a variety of local shops, restaurants, and cultural attractions, ensuring that you’ll never run out of things to do.

In Diamond Head, you’re not just buying a home; you’re investing in a lifestyle filled with adventure, relaxation, and the beauty of island living. Come discover why this enchanting neighborhood is the perfect place to call home!

Newest Diamond Head Homes with Waterfront Frontage

$12,500,000

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

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

Listing courtesy of Coldwell Banker Realty.

$17,500,000

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

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

Listing courtesy of Coldwell Banker Realty.

$26,500,000

5 Beds ⋅ 8 Baths ⋅ 202603726 MLS ⋅ FS - Fee Simple Tenure

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 appraisal! This modern masterpiece, nestled in the prestigious Cove Area of Diamond Head, offers over 7,465 square feet of living space that seamlessly blends cutting-edge design with island inspiration. From the expansive living areas that capture breathtaking views to the advanced whole-house automation and security systems, this home is a true technological marvel. The chef's kitchen, featuring professional-grade appliances and a spacious butler’s pantry, is a culinary dream. Every corner reveals something extraordinary, from the exquisite interior finishes to the stunning outdoor oasis. This beachfront home represents the pinnacle of island living, now available at an exceptional price that underscores its unmatched quality and prestige. Seize the opportunity to own this extraordinary residence and make it your own private paradise.

213 Kaalawai Place, Honolulu

Listing courtesy of Coldwell Banker Realty.

$55,000,000

11 Beds ⋅ 11 Baths ⋅ 202520629 MLS ⋅ FS - Fee Simple Tenure

Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties, spanning over two acres across two adjacent parcels. Zoned R-7.5 and encompassing nearly 89,120 square feet, the estate features two residences and an open lot, offering sweeping ocean views, beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Offered as a singular acquisition under TMKs 1-3-1-039-042-0000 and 1-3-1-039-005-0000, Ho‘oluana Estate presents a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records. Last four digits of the listing TMK do not exist, these are used only for MLS entry purposes.

3735 Diamond Head Road, Honolulu

Listing courtesy of Hawaii Life.

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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.