Diamond Head Real Estate

Diamond Head Real Estate

Welcome to Diamond Head, a stunning gem nestled on the southeastern coast of Oahu, Hawaii. Renowned for its iconic volcanic crater, Diamond Head is not just a breathtaking natural wonder but also a vibrant community that offers a unique blend of outdoor adventure, rich history, and a relaxed island lifestyle.

As you explore this picturesque region, you’ll find yourself surrounded by lush landscapes, pristine beaches, and panoramic views that stretch across the sparkling Pacific Ocean. The Diamond Head State Monument is a must-visit, where a moderate hike leads you to the summit, rewarding you with breathtaking vistas of Honolulu and the coastline. The trail is a favorite among both locals and tourists, making it a perfect spot for morning exercise or a leisurely afternoon stroll.

The neighborhood is also steeped in history. Originally named Lē‘ahi by the ancient Hawaiians, this area has significant cultural importance, with remnants of its military past visible in the historic bunkers and lookouts that dot the landscape. The charming residential streets are lined with an array of architectural styles, from quaint beach cottages to luxurious oceanfront estates.

Dining and shopping options abound, with local eateries serving up fresh poke, shave ice, and other Hawaiian delicacies. Whether you’re surfing at the famous Waikiki Beach or enjoying a sunset picnic at Kapiolani Park, Diamond Head offers an unparalleled lifestyle that captures the essence of island living.

With its breathtaking scenery, rich culture, and welcoming community, Diamond Head is not just a place to live; it’s a place to thrive. Experience the magic of this enchanting neighborhood and discover your dream home in paradise!

Newest Listings in Diamond Head

$1,625,000
3 Beds ⋅ 3 Baths ⋅ 202614187 MLS ⋅ FS - Fee Simple Tenure
Commanding panoramic, unobstructed city and ocean views protected by the Board of Water Supply property below. Extensively remodeled over the years (1997, 2015, and 2019). At the heart of the home is a beautifully renovated island kitchen that opens seamlessly to the house-wide deck and main living areas where panoramic vistas are the backdrop for everyday living and memorable gatherings. Desirable floor plan features a primary suite on the main living level w/private office & TV/den/reading room and separate entry to side yard. Lower level includes two bedrooms, spacious living area, wet bar, separate entry - ideal for extended family, guests, multigenerational or assisted living. Rare parking includes a two-car carport, driveway parking for two additional vehicles, plus coveted street parking. Just minutes from UH, freeway access, shopping, dining, and beaches. Experience the perfect blend of breathtaking views, versatile living, and exceptional convenience.

1516 Alencastre Street, Honolulu

Listing courtesy of Coldwell Banker Realty.

$775,000
3 Beds ⋅ 1 Baths ⋅ 202614249 MLS ⋅ FS - Fee Simple Tenure

1739 9th Avenue Unit A, Honolulu

Listing courtesy of Dream Home Realty Hawaii LLC.

$1,399,000
6 Beds ⋅ 4 Baths ⋅ 202614301 MLS ⋅ FS - Fee Simple Tenure
Location, location... come see this recently updated, move in ready, Kahala residence. This spacious 6-bedroom, 4-bath residence offers the ideal setup for multi-generational living, extended family, or flexible living arrangements. Offered fully furnished, this turnkey property includes 8 flat-screen TVs, 6 fully furnished rooms and furnished family rooms, making it ready for immediate enjoyment as a rental or residence. The home has been tastefully updated throughout with durable luxury vinyl plank (LVP) flooring, modern finishes, and a recently refreshed stucco exterior that provides excellent curb appeal. Stay comfortable year-round with air conditioning in the bedrooms and two mini-split AC systems serving the main living areas. Conveniently located just blocks from Kahala Mall, Diamond Head, Waikiki, major medical centers, shopping, dining, beaches, and entertainment. Enjoy quick access to downtown Honolulu and easy freeway connections for commuting across Oahu. PRICED TO SELL, WON'T LAST LONG!!

4576 Kalanianaole Highway, Honolulu

Listing courtesy of OahuRE.com.

$1,295,000
6 Beds ⋅ 2 Baths ⋅ 202611484 MLS ⋅ FS - Fee Simple Tenure
Bring your vision to this versatile two-level property featuring 6 bedrooms and 2 baths, with 3 bedrooms and 1 bath on each level. Offering flexible living options, including the potential for a studio with bath, this home is ideal for multi-generational living or investment possibilities. With some TLC, the property offers exceptional potential in a quiet, established neighborhood near Palolo Elementary School. Easy to see with 24-hour notice.

1842 Mahana Street, Honolulu

Listing courtesy of Artie Wilson & Associates.

$1,400,000
3 Beds ⋅ 2 Baths ⋅ 202614156 MLS ⋅ FS - Fee Simple Tenure
Discover the potential of this well-maintained single-level home with a few interior steps to an extended living room on a desirable corner lot of nearly 7,800 sq. ft. in Upper Aina Haina Valley. Surrounded by cool trade winds and lush mountain views, this home boasts front and side yards with fully fenced/walled perimeters offering generous space for outdoor living, gardening, entertaining, or play, and is ideal for your furry friends to roam. The flexible floor plan provides an excellent opportunity to update and personalize the home to your style. Additional features include newer exterior paint, updated electrical, a covered carport with a dedicated laundry storage area, and abundant street parking. Enjoy the peaceful valley setting with convenient access to Aina Haina Shopping Center, restaurants, schools, nearby beaches, Aina Haina Community Park, and scenic hiking trails. With its established neighborhood and easy access to Kahala, Hawaii Kai, and downtown Honolulu, this is a rare opportunity to own in one of East Honolulu's most desirable communities.

860 Hind Iuka Drive, Honolulu

Listing courtesy of Engel & Volkers Honolulu.

$1,388,000
3 Beds ⋅ 2 Baths ⋅ 202614098 MLS ⋅ FS - Fee Simple Tenure
Located in the coveted Waikiki Elementary School district, this single level home offers 3-bedroom, 2-bathroom with ample parking upfront. This home provides the Hawaiian lifestyle we are all looking for. Located only 1 house away from Paki Park, minutes away from Waikiki, Waikiki Beach, Diamond Head Crater, Kapiolani Park, Honolulu Zoo and Ala Moana, the best of Oahu is your backyard! It is in livable fixer upper condition with great bone and super floor plan. This home is ready for you to move in immediately while updating slowly. With love and care and yes, some money, the effort will be rewarded. The outdoor space is mostly concrete all around for easy maintenance. Come see this charming home before it's gone. *A few photos are virtually staged(enhanced).

3012 Lakimau Street, Honolulu

Listing courtesy of REMAX Hawaii.

$2,800,000
5 Beds ⋅ 3 Baths ⋅ 202613575 MLS ⋅ FS - Fee Simple Tenure
First open house 7/26/2026 from 1:30 - 5:00. Exceptional views, exceptional house!! Rare opportunity to make this coveted combination your home! Sweeping ocean views include views of Waialae Golf Course and Diamond Head. Living room, dining area, primary bedroom, covered lanais all perfectly situated to savor the views. Main upper level contains 3 bedrooms, 2 baths, laundry/pantry area. Bonus: no stairs to navigate from from carport to main living area, upper level has Mitsubishi ceiling a/c for living/dining area & kitchen. Upper level bedrooms have split a/c and ceiling fans. Lower level contains family room, office 'niche', guest bedroom, exercise room (5th bedroom), bath (also accessible to pool). Ocean views from family room & exercise room. Separate workshop adjacent, but not connected to family room. Pool level is easily accessible from family room, exercise room and bath. Pool area also has stunning views. Bonus: Lanai overhang provides a comfortable, shaded area for lounging around the pool while being protected from the sun. Bonus: House has PV system and solar water heater. House has been well cared for but is being sold in "as is" condition.

1474 Kamole Street, Honolulu

Listing courtesy of Hawaii Modern Realty.

$1,298,000
3 Beds ⋅ 3 Baths ⋅ 202612198 MLS ⋅ FS - Fee Simple Tenure
Cooled by gentle mountain breezes & blessed with sweeping coastline views stretching toward Diamond Head, this exceptional 3-unit property offers the kind of island lifestyle people dream about. Upstairs, a spacious covered lanai becomes the heart of the home, a place to greet the morning with a cup of coffee as the sun rises over the Pacific, to gather with friends for leisurely meals, or unwind in the evening while watching mesmerizing sunsets paint the sky in shades of gold & pink. The well-appointed kit flows effortlessly to the outdoor living space, making entertaining and dining al fresco both easy & enjoyable. Whether preparing a casual breakfast or hosting a sunset dinner, everything is designed to embrace the HI indoor-outdoor way of life. The upstairs residence features 2 comfortable bedrooms & 1 bathroom, creating a peaceful retreat where the sights, sounds & breezes of the islands are never far away. The downstairs 1 bedroom unit has a generous sized living area leading out to the covered lanai. Easy walking distance to Waialae Avenue with numerous restaurants & boutique shops. Small studio also included in the offering.

4137 Sierra Drive, Honolulu

Listing courtesy of Coldwell Banker Realty.

$1,080,000
3 Beds ⋅ 1 Baths ⋅ 202613586 MLS ⋅ FS - Fee Simple Tenure
Location, Lifestyle & Opportunity! Classic island charm meets endless possibilities. Nestled in the highly desirable Kapahulu neighborhood, just minutes from Waikiki, Diamond Head, Kapiolani Park, zoo, Waikiki Shell, beautiful beaches, local dining, shopping, and entertainment. Filled with timeless character, this home offers the opportunity to update and personalize while preserving its classic island appeal. Where you're looking for a place to call home or an investment in one of Honolulu's most sought -after neighborhoods, you'll appreciate the convenience of the vibrant island lifestyle that makes Kapahulu so special. Discover the Charm, Embrace the possibilities and make this property your own. Actual Bedroom count does not match tax records.

3042 Makini Street, Honolulu

Listing courtesy of Ron Corp..

$2,395,000
5 Beds ⋅ 2 Baths ⋅ 202610744 MLS ⋅ FS - Fee Simple Tenure
Discover a rare Kaimuki find — two separate homes on one expansive 10,000 sq ft lot, zoned R-5. This is the multi-generational or income-producing property you've been waiting for! The front home offers 3 bedrooms, 1 bath, while the second home features 2 bedrooms, 1 bath — perfect for extended family living, house hacking, or growing your investment portfolio with two rentable units. Set on one of the largest lots in the neighborhood, there's plenty of room to spread out, garden, park multiple vehicles, or explore future potential (buyer to verify). Enjoy the classic Kaimuki lifestyle — walkable to Waialae Avenue's boutique shops, coffee spots, and local eateries, with easy access to Schools, Kapiolani Community College, Diamond Head, and Kahala Mall. Opportunities like this — two homes, one large lot, prime Kaimuki location — don't come around often. Whether you're planning for family, hedging your investment, or seeking rental income potential, this property checks every box.

820 10th Avenue, Honolulu

Listing courtesy of REMAX Hawaii.

$5,050,000
4 Beds ⋅ 3 Baths ⋅ 202614040 MLS ⋅ FS - Fee Simple Tenure
Nestled on the prestigious Diamond Head neighborhood, offers a large 15,000 sqft lot overlooking Kahala with ocean views. Bring your architect and contractor to design your home. Conveniently located near Kapiolani Park, Diamond Head, Kahala Mall, beaches, and Waikiki, making it an exceptional place to enjoy both tranquility and island living at its best.

633 Hakaka Place, Honolulu

Listing courtesy of Hawaii Resource Realty.

$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.

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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.