Diamond Head Homes with Dead End Lot Features

Welcome to Diamond Head, one of Honolulu’s most picturesque neighborhoods, where breathtaking views and a vibrant community blend seamlessly. Nestled on the southeastern coast of Oahu, Diamond Head is renowned for its iconic volcanic crater, lush landscapes, and proximity to stunning beaches. This charming area is not just a feast for the eyes; it’s a lifestyle choice that offers a unique blend of outdoor recreation, cultural experiences, and a welcoming atmosphere.

One of the standout features of homes in Diamond Head is the availability of properties with dead-end lot features. These homes provide a sense of tranquility and privacy, perfect for families or individuals seeking a peaceful retreat amidst the hustle and bustle of city life. With limited traffic and minimal disturbances, residents can enjoy serene evenings, safe play areas for children, and a strong sense of community.

In addition to the peaceful living environment, Diamond Head is a stone's throw away from some of Oahu's best attractions. Enjoy a morning hike up the Diamond Head State Monument for panoramic views of the Pacific Ocean, or spend your afternoons at the nearby beaches, soaking up the sun and surf. The neighborhood also boasts a rich cultural scene, with local eateries, art galleries, and boutique shops that reflect the vibrant spirit of Hawaii.

With its stunning natural beauty, family-friendly atmosphere, and unique home features, Diamond Head is more than just a neighborhood; it’s a lifestyle waiting to be embraced. Discover your dream home in this enchanting enclave today!

Newest Diamond Head Homes with Dead End Lot Features

$12,500,000

5 Beds ⋅ 4 Baths ⋅ 202613905 MLS ⋅ FS - Fee Simple Tenure ⋅ 22 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

$26,500,000

5 Beds ⋅ 8 Baths ⋅ 202603726 MLS ⋅ FS - Fee Simple Tenure ⋅ 181 DOM

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

$43,000,000

5 Beds ⋅ 7 Baths ⋅ 202520630 MLS ⋅ FS - Fee Simple Tenure ⋅ 313 DOM

Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties. Zoned R-7.5 and encompassing nearly 80,000 square feet, the estate features an expansive residences and several open lots, offering sweeping ocean views, private/deeded 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. Neighboring property located at 3735 Diamond Head Road A, is also available for sale, presenting a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records.

3735- Diamond Head Road, Honolulu

$12,000,000

6 Beds ⋅ 4 Baths ⋅ 202520628 MLS ⋅ FS - Fee Simple Tenure ⋅ 313 DOM

Exceptional Beachfront Luxury on Honolulu’s Iconic Diamond Head! A rare gem on one of Honolulu’s most coveted stretches of beach, this stunning beachfront estate offers an unparalleled lifestyle. Nestled on the prestigious Diamond Head coastline, this exquisite residence sits directly on a pristine white sand beach with crystal-clear waters perfect for snorkeling and a variety of ocean activities. This turnkey home is a true Kama'aina re-treat, offering a balance of comfort and coastal beauty. The property boasts a meticulously manicured lawn, lush tropical landscaping, and an elevated private yard that ensures both serenity and seclusion. Gated entryways provide ultimate privacy and security, making this an ideal retreat. This rare opportunity is exclusively available for purchase either in conjunction with the neighboring property at 3735 Diamond Head Road OR after the larger estate has sold.

3735 Diamond Head Road Unit A, 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.