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, this neighborhood is not just a feast for the eyes but a treasure trove of experiences waiting to be discovered. With its breathtaking views of the Pacific Ocean and the vibrant city of Honolulu, Diamond Head offers a perfect blend of natural beauty and urban convenience.

As a historical landmark, Diamond Head is steeped in rich cultural heritage, with its name derived from the 19th-century British sailors who mistook calcite crystals on the crater for diamonds. Today, it stands as a symbol of Hawaii's unique history and natural splendor. The area is home to the famous Diamond Head State Monument, where visitors can hike to the summit for panoramic views that are nothing short of spectacular.

Living in Diamond Head means embracing an outdoor lifestyle. With pristine beaches like Kapiolani Park and the warm sands of Waikiki just a stone’s throw away, residents enjoy a plethora of water activities, from surfing to snorkeling. The neighborhood is also dotted with charming cafes, boutique shops, and local eateries that showcase the rich flavors of Hawaiian cuisine.

For those seeking a vibrant community with a touch of paradise, Diamond Head offers an array of real estate options, from modern condos with ocean views to cozy single-family homes surrounded by lush landscapes. Experience the magic of island living in Diamond Head, where every day feels like a vacation. Discover your dream home in this enchanting paradise today!

Newest Listings in Diamond Head

$898,000

3 Beds ⋅ 2 Baths ⋅ 202616024 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

3 Bedroom, 1 bath upstair and below, similar to a studio style with 1 bathroom.Diamond Head, Waikiki and mountain views. Near busline, schools and stores, restaurant and banks. To be sold in "As Is" condition no repairs to do. No Seller Disclosure Statement to be provided. Sale of property is subject to finding replacement home for the Seller

1768 Palolo Avenue Unit H, Honolulu

$2,800,000

4 Beds ⋅ 3 Baths ⋅ 202615777 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 DOM

Perched within the gated community of Hawaii Loa Ridge, 869 Ikena Circle captures sweeping ocean, coastline, and mountain views from an elevated East Honolulu setting. Expansive windows fill the home with natural light and showcase the blue Pacific from the spacious main living areas, which extend to a covered lanai for effortless indoor-outdoor living. Renovated in 2025, the thoughtfully designed floor plan offers a bedroom and full bath on the main level, along with a versatile office/den, while upstairs you'll find two generously sized en-suite bedrooms offering privacy and separation. Step outside to your own private pool surrounded by tropical greenery—the perfect setting to relax, entertain and take in the island surroundings. Additional highlights include 86 owned photovoltaic panels, a laundry room, and a 2 car garage with more covered parking in front. Residents of Hawaii Loa Ridge enjoy 24-hour gated security along with community tennis courts, a clubhouse, playground, BBQ areas and access to the Hawaii Loa Ridge hiking trail. A rare opportunity to enjoy privacy, space, security, and panoramic views in one of East Honolulu's most sought-after gated neighborhoods!

869 Ikena Circle, Honolulu

$985,000

1 Baths ⋅ 202614438 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 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

$1,895,000

202615940 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

Located in desirable Palolo Valley, this four-plex presents an excellent investment opportunity, each offering 3 bedrooms and 2 bathrooms; for a total of 12 bedrooms and 8 bathrooms. Each unit features a private entrance, tile flooring throughout, abundant natural light, granite countertops, and stainless steel appliances. Conveniently located near public transportation, shopping, dining, and neighborhood amenities, the property offers easy access to major thoroughfares. Also inputted as SFH under MLS #202601575

1628 9th Avenue, Honolulu

$2,000,000

3 Beds ⋅ 3 Baths ⋅ 202615383 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

RARELY AVAILABLE - LOWER WAIALAE IKI NEXT TO THE PARK!! This renovated 3bed/3bath home is located in desirable Waialae Iki and features an open floorplan, panoramic ocean views, quartz counter tops, large designer kitchen, recessed lighting, custom cabinets, chandeliers, newer appliances, gas cooktop, laundry room, large jacuzzi, ample storage, split AC's, built-in shelves, Diamond Head/Ocean views, cool trade winds, mango tree, and a large rooftop space perfect for nightly sunsets & entertaining family, friends, & children! This home is located just steps from Waialae Iki Neighborhood Park, and is conveniently located near Kahala Mall, Waialae Country Club, Aina Haina Shopping Center, Kahala Beach, University of Hawaii, Chaminade, Diamond Head, Kaimuki restaurants, schools, grocery stores, parks, bus stops, beaches & more...Don’t miss this opportunity!!

4846 Analii Street, Honolulu

$2,275,000

5 Beds ⋅ 4 Baths ⋅ 202615526 MLS ⋅ FS - Fee Simple Tenure ⋅ 2 DOM

MUST SEE! This stunning Kapahulu residence offers a fresh, modern and cohesive living environment with thoughtful updates throughout - providing the peace of mind and feel of a truly renewed home. With an additional living space downstairs, this flexible two-story floor plan offers excellent versatility for multigenerational living, guests or a variety of lifestyle needs. Enjoy a newly landscaped yard, enhanced with exterior lighting and irrigation, creating a beautiful and functional outdoor space for relaxing or entertaining. Generous parking, including a covered carport and additional on-site parking. Walk to Safeway, Starbucks, dining and everyday conveniences with Waikiki, Diamond Head and beaches just minutes away. A rare opportunity to own a truly move-in-ready home in one of Honolulu's most convenient and sought after neighborhoods.

3237 Olu Street, Honolulu

$50,000

2 Beds ⋅ 2 Baths ⋅ 202615775 MLS ⋅ LH - Leasehold Tenure ⋅ 3 DOM ⋅ Kahala Beach BLDG.

Enjoy the beauty and serenity of Kahala Beach from this spacious 1,555 sq ft, 2-bedroom, 2-bathroom ground-floor condominium at Kahala Beach Apartments. Ideally located on Kahala Avenue, this fully furnished residence is just steps from the beach and conveniently close to Kahala Hotel, Kahala Mall, restaurants, shopping, and easy access to Honolulu. The generous floor plan features an enclosed lanai that expands the living space and offers a peaceful garden setting. The unit is fully furnished with comfortable Hawaiian-style décor and includes a king bed in the primary bedroom, two queen beds in the second bedroom, and two sofa beds, providing ample space for family and guests. Enjoy the convenience of ground-floor living with easy access to the pool and recreation areas, plus the ability to bypass the elevator. The property also includes one covered garage parking stall and storage. A unique opportunity to own in one of Honolulu’s desirable beachfront communities. The lease term ends July 2027, but you can rent from Kamehameha schools after providing additional time to enjoy or utilize the property. Maintenance fee includes all utilities. Lease rent paid til October 2026!

4999 Kahala Avenue Unit 148, Honolulu

$2,395,000

5 Beds ⋅ 3 Baths ⋅ 202615817 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

Built in 2022 and ideally positioned on lower Sierra Dr., this modern 5-bed, 3-bath home captures unobstructed, sweeping coastline & city views from this perimeter lot. Thoughtfully designed to take advantage of the views and natural light, the home offers a flexible floor plan well suited for everyday living, entertaining, guests, or extended family. Entry level offers large glass sliding doors opening to a large lanai off the kitchen and living areas and a bedroom with full bath. Lower level features a second open living room with the additional 4 bedrooms, 2 baths, laundry and 2 additional lanai's, plus a landscaped Living wall off the bedroom glass sliding doors. High ceilings, sprinklers, ceiling fans and privacy make this home feel like it's perched on the edge of the world. Enjoy the benefits of newer construction in one of Honolulu's most established hillside neighborhoods, just mins from Kaimuki, Waialae Ave, dining, shopping, schools, and freeway access. The property includes a 2-car carport plus 2 additional guest parking stalls—a valuable convenience in the area. Driveway is shared. Lower yard grated and perfect for chairs, firepit and sunset views.All decks repainted.

3616 Sierra Drive, Honolulu

$2,050,000

6 Beds ⋅ 3 Baths ⋅ 202615523 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM

Views, convenience and privacy! Minutes from Kahala Mall, schools, medical clinics and H-1 freeway access, this lower Waialae Nui Ridge home offers views of the sparkling Kahala coastline, Diamond Head and Waikiki skyline. Flexible SINGLE LEVEL floorplan includes 6 bedrooms, 3 bathrooms and a spacious family room. Enjoy mornings and unwind in the evenings on the covered view lanai. A variety of mature fruit trees enhance the yard with room to garden. Wonderful corner location with driveway on Uhi Place.

1688 Halekoa Drive, Honolulu

$1,448,000

3 Beds ⋅ 2 Baths ⋅ 202615153 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

A Timeless and Classic Home … Perched above Center Street in sought-after Wilhelmina, this beautifully updated vintage home blends timeless character with thoughtful modern enhancements. Originally built in 1928 and extensively renovated in 2015, the residence retains its distinctive charm while offering comfortable contemporary living. High ceilings, abundant windows, and beautiful wood flooring create a warm, inviting atmosphere filled with natural light. The flexible lower-level 3rd bedroom/studio space is a feature incorporating natural boulders into its design and offering its own wetbar and beautifully finished on-suite bath all add an elevated touch. On the main level, step outside to an expansive deck ideal for morning coffee, sunset gatherings, and entertaining which you’ll enjoy while taking in views from Palolo Valley, the city and ocean all adding to its appeal. Conveniently located near the entertainment of Kaimuki's dining, shopping and easy access to the freeway.

1439 Center Street, Honolulu

$1,400,000

3 Beds ⋅ 2 Baths ⋅ 202615578 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM ⋅ Kalani Iki Estates BLDG.

Tucked away in a cool, quiet & peaceful neighborhood, Kalani Iki Estates feels uniquely special as you arrive through the lush tree-lined community. This bright, modern 3-bedroom, 2-bath split-level home has been exceptionally maintained & thoughtfully updated. Soaring high ceilings & wrap-around floor-to-ceiling windows welcome you home to a contemporary floor plan, natural light & garden views throughout. Features & upgrades include a re-imagined kitchen with new quartz counter-tops & updated appliances, a dedicated dining space, luxury vinyl flooring, all-new windows & doors throughout, upgraded lighting, roller & zebra shades, two split A/C units & more. Three bedrooms are positioned on the upper-level for added privacy, plus a walk-in storage & walk-in laundry room. This home includes two covered parking stalls. Furnishings available for purchase to make this a turn-key package. Kalani Iki Estates includes landscaping & trash service, an on-site swimming pool, large covered entertainment space & a newly refurbished pickleball court. Minutes to Kahala, Hawaii Kai, urban Honolulu & beyond, this exceptional home in a truly special location is one you won't want to miss.

1500 Kalaniiki Street Unit 13, Honolulu

$1,475,000

3 Beds ⋅ 3 Baths ⋅ 202615490 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM

Discover island living in the heart of Kaimuki with this spacious 3-bedroom, 2.5-bathroom CPR single-family home. Located right across from Kapaolono Community Park, you'll enjoy a peaceful, private setting just moments from urban conveniences. The functional, open-concept floor plan seamlessly connects the living and dining spaces—perfect for gathering and entertaining. Highlights include generous closet space throughout, light-filled bedrooms, and a tranquil primary suite. Conveniently located minutes from kaimuki popular eateries, shops, top schools, and freeway access.

740 11th Avenue Unit B, 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.