Diamond Head Real Estate

Diamond Head Real Estate

Welcome to Diamond Head, one of Honolulu's most iconic and picturesque neighborhoods, nestled on the southeastern coast of Oahu, Hawaii. This stunning region is renowned for its breathtaking natural beauty, rich history, and vibrant community, making it a sought-after destination for both residents and visitors alike.

At the heart of Diamond Head lies the legendary volcanic crater, a striking geological formation that offers panoramic views of the Pacific Ocean and the bustling city of Honolulu. Hiking enthusiasts will revel in the challenge of the Diamond Head Summit Trail, which rewards trekkers with awe-inspiring vistas and a sense of accomplishment. The surrounding area is dotted with lush parks, inviting beaches, and charming local shops, creating a perfect blend of outdoor adventure and leisurely exploration.

Diamond Head's unique location provides easy access to some of Oahu's most celebrated attractions. Just a short drive away, you can immerse yourself in the vibrant culture of Waikiki, explore the historic sites of Pearl Harbor, or indulge in the island's world-class dining and shopping experiences. The neighborhood itself boasts a laid-back atmosphere, with a welcoming community spirit that embraces both locals and newcomers.

Real estate in Diamond Head offers a diverse range of options, from luxurious oceanfront condos to charming single-family homes, many of which feature stunning views and proximity to the beach. Whether you're looking for a permanent residence, a vacation home, or an investment property, Diamond Head presents an unparalleled lifestyle in one of the most desirable locations in Hawaii.

Experience the magic of Diamond Head, where the beauty of nature meets the warmth of island living. Discover your dream home in this enchanting paradise today!

Newest Listings in Diamond Head

$4,099,000
4 Beds ⋅ 4 Baths ⋅ 202614472 MLS ⋅ FS - Fee Simple Tenure
Live your best life by the Pacific Ocean in one of Oahu’s most prestigious and sought after enclave communities. Tucked away within the gates of Black Point, this hidden gem offers a rare blend of privacy, space, view, and coastal charm! Designed for effortless indoor-outdoor living, the expansive layout features 4 bedrooms, 3 full baths, and 1 half bath, with sun drenched spaces that open to a private swimming pool and sweeping patio poolside deck. This property was designed to capture refreshed year round trade winds, ocean, and sunrise views. Presenting an incredible restoration opportunity, the existing residence serves as the ultimate canvas to reimagine, rebuild, or restore a world-class coastal estate. Complete with private access to the legendary Black Point oceanfront saltwater pool naturally filled by the waves of the Pacific. This is a once in a lifetime opportunity to create a legacy property. A truly magnificent island lifestyle awaits!

4134 Black Point Road, Honolulu

Listing courtesy of List Sotheby's Int'l Realty.

$1,980,000
4 Beds ⋅ 4 Baths ⋅ 202614041 MLS ⋅ FS - Fee Simple Tenure
Rare opportunity to own 10,000 sq ft of level land in Kuliouou featuring a spacious 3-bedroom main home plus a separate 1-bedroom unit—ideal for extended family, guests, home office, or rental income. The main residence (approx. 1,742 sq ft) offers 3 bedrooms and 2 baths, while the attached 1-bedroom, 1-bath unit includes its own generous living area and has been consistently rented for $2,250/month. Enjoy indoor-outdoor living with a huge 742 sq ft covered lanai complete with built-in bar, perfect for entertaining. The home showcases high ceilings, open beam design, large windows, and abundant natural light, along with spacious bathrooms featuring skylights and a remodeled kitchen with a large island and quartz countertops. Additional features include a workshop with half bath attached to the garage. Meticulously updated in 2019 and move-in ready. Equipped with 30 PV panels and 2 Tesla Powerwalls (leased). Conveniently located near shopping, dining, beaches, and just minutes to town—offering the perfect blend of comfort and peaceful island living.

6085 Manukapu Place, Honolulu

Listing courtesy of Forward Realty.

$5,750,000
6 Beds ⋅ 6 Baths ⋅ 202614908 MLS ⋅ FS - Fee Simple Tenure
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

Listing courtesy of Coldwell Banker Realty.

$1,465,000
3 Beds ⋅ 2 Baths ⋅ 202613724 MLS ⋅ FS - Fee Simple Tenure
Welcome to this move-in ready Kaimuki Gem! This charming 3 bedroom 2 bath Single Family Home offers great cross breezes and a spacious, well-designed floor plan that lives larger than its square footage. Enjoy ocean views from the living room, along with stunning views of iconic Diamond Head. Thoughtful updates, including split AC's and new flooring throughout, create a fresh and inviting feel from the moment you step inside. The large covered lanai extends your living space, making it the perfect spot for relaxing, dining, or entertaining year-round. A standout feature is the newer full-size 1 car garage, complete with an adjacent laundry room and separate storage room, offering convenience and valuable extra space. Located in one of Honolulu's most sought-after neighborhoods, this home is just minutes from Kaimuki's popular restaurants, cafés, shopping, parks, beaches, and schools. With only two owners in its history, this is a rare opportunity to own a well-maintained home in an exceptional location. Come experience the charm, views, and lifestyle that make Kaimuki one of Oahu's most desirable neighborhoods.

623 10th Avenue, Honolulu

Listing courtesy of Corcoran Pacific Properties.

$7,000,000
5 Beds ⋅ 7 Baths ⋅ 202614361 MLS ⋅ FS - Fee Simple Tenure
Welcome to 'Hotel Aloha,' a masterpiece of opulence, grace, and authentic Hawaiian design. This elegant 2-story residence features 5 spacious en-suite bedrooms, each offering a private luxury bathroom, generous closet space & breathtaking views. 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 & migrating whales. 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 that extends throughout the residence. 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 include dual washer/dryer sets, central AC, and immediate access to a pristine white sandy beach.

5599 Kalanianaole Highway, Honolulu

Listing courtesy of Hawaii Life.

$950,000
3 Beds ⋅ 2 Baths ⋅ 202614780 MLS ⋅ FS - Fee Simple Tenure
Highly coveted location. Near bus stops, schools, UH, Waikiki, zoo, aquarium, shopping centers & other areas. Fenced for privacy. Selling "As Is"; please include As Is Addendum. House is in tear-down condition, value is in land.Appliances not part of this sale, too old.Delete J-7 (existing warranties), M-1 (no condo docs available), N-2 (not a rental).

729-A 6th Avenue Unit A, Honolulu

Listing courtesy of All Realty Company.

$1,750,000
5 Beds ⋅ 3 Baths ⋅ 202614751 MLS ⋅ FS - Fee Simple Tenure
Welcome home to this spacious 5-bedroom, 3-full-bath, two-story residence offering the flexibility today’s buyers are looking for. Featuring separate entrances to each level, this home is ideal for multigenerational living, extended family, or guests. Take in beautiful Diamond Head views from the upper level while enjoying generous living spaces filled with natural light. The versatile floor plan provides endless possibilities to customize and make the home your own. Conveniently located near schools, shopping, dining, parks, and just minutes from Honolulu’s renowned beaches and attractions, this property combines everyday convenience with island living. Whether you’re searching for a primary residence with room to grow or a home with flexible living arrangements, this property is a must-see.

3148 Catherine Street, Honolulu

Listing courtesy of eXp Realty.

$2,750,000
202614756 MLS ⋅ FS - Fee Simple Tenure
Build your legacy in the heart of Honolulu. Rarely does an opportunity like this become available. Set in Wilhelmina, this exceptional 13,246 sf vacant parcel offers breathtaking 180-degree views of Diamond Head, the Pacific Ocean, sparkling city lights, and unforgettable sunset vistas. This premier estate lot provides the perfect canvas for an exceptional custom estate. The generous lot size and favorable development potential allow for your dream lifestyle residence. The design allows for 3 -5 car garage plus, room for 6+ cars in the driveway A separate dwelling can also be built if desired. Conceptual plans and architectural renderings by local, award-winning architect Jim Schmit are available; the permitting process is underway. Buyers may obtain the plans and continue the process toward bringing this extraordinary vision to life. Enjoy a sought-after scenic island lifestyle that combines privacy, prestige, and convenience, just minutes from the vibrant dining, shopping, cafés, and beaches. This is a rare chance to secure a landmark property and build a legacy home. Being sold with TMK 1-3-3-032-031-0001.

3950 Sierra Drive Unit A, Honolulu

Listing courtesy of Caron B Realty.

$8,950,000
6 Beds ⋅ 8 Baths ⋅ 202614467 MLS ⋅ FS - Fee Simple Tenure
Available now on coveted Kahala Avenue, this recently renovated gated estate offers refined modern island living just moments from the premier access to the sandy shores of Kahala beach. Thoughtfully designed with over 7,100 sq. ft. of indoor-outdoor living, the flexible 6+ bedroom floor plan features multiple living areas, guest accommodations, three separate office areas, a detached fitness bungalow, and a seamless connection to the tropical pool and yard areas. Contemporary upgrades include natural stone flooring throughout, a custom chef’s kitchen with walnut cabinetry, Miele and Wolf appliances, formal dining with a wet bar, and luxury suite retreats on both levels. Complete with an enclosed two-car garage, generous guest parking, and gated privacy, this sophisticated Kahala residence is move-in ready and designed for exceptional island living and entertaining. Access to Kahala Beach and the ocean is conveniently located directly across the street from the property.

4714 Kahala Avenue, Honolulu

Listing courtesy of Hawaii Life.

$1,688,000
3 Beds ⋅ 2 Baths ⋅ 202614551 MLS ⋅ FS - Fee Simple Tenure
NEW LISTING!! Welcome to this charming single-family home in desirable Kaimuki! This 3 bdrms/2 baths home features a spacious open floor plan designed for comfortable everyday living and entertaining. Enjoy fresh interior and exterior paint, brand-new carpet, and a bright, inviting interior. The kitchen is equipped with stainless steel appliances and flows seamlessly into the main living areas. Downstairs semi-finished basement can be easily enclosed for additional living space. Conveniently located near beautiful beaches, parks, and Kahala Mall with an abundance of dining and shopping options. This home offers the perfect blend of comfort, flexibility, and an unbeatable location. Don't miss this fantastic opportunity to own in one of Honolulu's most sought-after neighborhoods!

923 22nd Avenue, Honolulu

Listing courtesy of REMAX Hawaii.

$1,450,000
3 Beds ⋅ 2 Baths ⋅ 202613796 MLS ⋅ FS - Fee Simple Tenure
NEW LISTING!! Discover this beautifully updated and expanded 3 bdrm/2 bath single-family home nestled in the highly sought-after Kapahulu neighborhood. This IMMACULATE residence blends modern renovations with everyday comfort. Fresh exterior paint, luxury vinyl plank flooring, and a bright, open floor plan create a warm and inviting atmosphere. The spacious living room captures beautiful city and mountain views, while the renovated kitchen features stainless steel appliances, updated cabinetry, and ample space for cooking and entertaining. Both bathrooms have been tastefully remodeled with contemporary finishes. Conveniently located near parks, beaches, shopping, dining, and everything Kapahulu has to offer, this is a rare opportunity to own a beautifully upgraded home in one of Honolulu's most desirable neighborhoods. A must-see to truly appreciate!

3331-A Herbert Street, Honolulu

Listing courtesy of REMAX Hawaii.

$560,000
2 Beds ⋅ 1 Baths ⋅ 202614519 MLS ⋅ FS - Fee Simple Tenure ⋅ Diamond Head Hillside BLDG.
Rarely available pet friendly 2-bedroom residence nestled on the coveted slopes of Diamond Head, where up to two pets are welcome. Efficiently designed for comfortable island living, this home captures cooling tradewinds and expansive views from the Honolulu skyline to the lush Ko'olau Mountains Ideally situated with proximity to Waikiki and Gold Coast neighborhoods and just moments from the vibrant cafés, restaurants, and boutiques of Monsarrat Avenue. The convenience abounds with effortless access to Waikiki Elementary, Kapiolani Park, Waikiki Beach, Kapiolani Community College, Diamond Head Theatre, and some of Oahu's best dining, recreation, and outdoor pursuits. A wonderful opportunity to own in one of Honolulu's most sought-after neighborhoods.

3151 Monsarrat Avenue Unit 502, Honolulu

Listing courtesy of Hawaii Modern 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.