Diamond Head Homes with City View

Welcome to Diamond Head, one of Honolulu’s most iconic neighborhoods, where breathtaking vistas and a vibrant lifestyle converge. Nestled on the southeastern coast of Oahu, this stunning locale is renowned for its striking volcanic crater, which offers a backdrop of natural beauty and adventure. The allure of Diamond Head extends beyond its picturesque landscapes; it boasts a rich history and a vibrant community atmosphere that captivates residents and visitors alike.

Living in Diamond Head means immersing yourself in a world of outdoor activities and cultural experiences. The area is home to pristine beaches, lush parks, and scenic hiking trails, including the famed Diamond Head State Monument, where you can trek to the summit for panoramic views of the Pacific Ocean and the Honolulu skyline. Whether you're enjoying a morning surf session or an evening stroll along the beach, the charm of this neighborhood is palpable.

One of the most enticing features of Diamond Head is the availability of homes with stunning city views. Imagine waking up each day to the sight of the sun rising over the vibrant cityscape of Honolulu, with the ocean glistening in the distance. These residences offer not just a home, but a lifestyle filled with beauty and tranquility. The architectural styles range from charming bungalows to luxurious estates, all designed to maximize those breathtaking views.

In Diamond Head, you’re not just buying a property; you’re investing in a lifestyle defined by natural beauty, rich culture, and a warm, welcoming community. Come experience the magic of Diamond Head, where your dream home awaits amidst the stunning backdrop of Hawaii’s paradise.

Newest Diamond Head Homes with City View

$2,000,000

3 Beds ⋅ 3 Baths ⋅ 202615383 MLS ⋅ FS - Fee Simple Tenure ⋅ 0 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

$2,395,000

5 Beds ⋅ 3 Baths ⋅ 202615817 MLS ⋅ FS - Fee Simple Tenure ⋅ 1 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 ⋅ 1 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 ⋅ 4 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

$1,275,000

3 Beds ⋅ 2 Baths ⋅ 202609335 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM

Vintage 1940's bungalow located in the super convenient Kapahulu area at the base of Diamond Head Crater. This charming home with many original features, that made it so cute, are intact and has been meticulously maintained throughout the years. Kitchen and bathrooms have been remodeled to todays standards... New fixtures, new appliances - including a gas range, AC's and ceiling fans in each room, new cabinetry, LVP flooring, fresh paint, lighting etc. makes this a perfect move-in ready home. Nicely landscaped exterior with full grassy areas, large mango tree for cool shade, fully fenced and gated yard, multiple tandem car parking with a laundry / storage room behind the carport are all features that make this a great property! There is a large concrete patio off the laundry room... possible extension for a future home office or additional bedroom? Definitely a classically adorable, move-in ready property on the outskirts of Waikiki!

3327 Catherine Street, Honolulu

$535,000

1 Beds ⋅ 1 Baths ⋅ 202614934 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM ⋅ Ilima Apts BLDG.

Located at desirable Pualei Circle in the Diamond Head neighborhood, Ilima Apartments offer peaceful residential living with the best of Honolulu just minutes away. Waikiki Elementary School is within walking distance. Diamond Head, Kapiolani Park, Waikiki Beach, Kaimana Beach, Queen’s Surf and the Honolulu Zoo are all conveniently nearby. Enjoy easy access to some of Honolulu’s favorite cafes, restaurants, bakeries and local eateries along Monsarrat Avenue, Kapahulu and Kaimuki. Assigned storage locker has space for surfboards and bicycles. The condo was beautifully renovated in 2020, including updated plumbing, providing modern comfort and peace of mind. With its tranquil salt water pool, quiet neighborhood setting, walkable access to school, beaches, parks, dining, and everyday conveniences, Ilima Apartments at Pualei Circle offers an exceptional opportunity to enjoy the best of island living in one of Honolulu’s most sought-after locations.

3093 Pualei Circle Unit 208, Honolulu

$1,295,000

5 Beds ⋅ 3 Baths ⋅ 202614648 MLS ⋅ FS - Fee Simple Tenure ⋅ 8 DOM

“Own an original”: The original owner of these beautiful, classic homes in Palolo valley is ready for the next generation of owners, investors, or developers to call this place home. Nestled on the mauka (mountain) side of 10th Avenue, you feel like you are in a special retreat, away from the hustle and bustle of the urban core, yet only 1 mile from Wai’alae Ave in the vibrant neighborhood community of Kaimuki - close to locally owned restaurants, retail shops and bus lines. Two separately metered (water, sewer and electrical) single family homes with an enclosed 2 car garage on 10th Ave. Main home on 10th Ave is a 3 bd / 1.5 bath with an unfinished basement for extra storage or remodel potential and covered lanai. Upper home 2 bd / 1 ba with a spacious, terraced backyard of property with even more potential to extend or build; buyer to do their own due diligence regarding permitting and capacity to build. Conveniently located across from Palolo Elementary, two blocks from Honolulu Fire Dept Station and 4 blocks away from Palolo Community Center with swimming pool, basketball courts and baseball field.

2077 10th Avenue, Honolulu

$1,825,000

5 Beds ⋅ 3 Baths ⋅ 202614839 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM

Most homes trade elevation for the view—climb higher, live farther from everything. This Halekoa Drive home rewrites that story: nearly 180 degrees of open ocean and Diamond Head from every level, perched low enough to keep daily life close. Four bedrooms sit upstairs; below, a detached rental unit with its own entrance, bath, and wet bar gives you a flexible lower level - an income offset, a guest suite, or extra room for your Ohana. Sixteen owned solar panels and solar hot water run on net metering, putting the energy math in your favor. A neighborhood park sits just a few blocks off, and the address lands in some of Honolulu's most sought-after public school districts. This house is built for the buyer who wants the unobstructed views without the climb. The home has been tastefully maintained with contemporary flooring, spacious bedrooms, and an EV equipped garage you can pull into after a long day at the beach. You can count on one hand how many homes on the hill like this come to market. Don't miss your chance to stand in this space and feel the tranquility it holds. Call your favorite realtor today for a private showing, and welcome home.

1492 Halekoa Drive, Honolulu

$1,465,000

3 Beds ⋅ 2 Baths ⋅ 202613724 MLS ⋅ FS - Fee Simple Tenure ⋅ 15 DOM

Welcome to this move-in ready Kaimuki Gem! This charming 3 bedroom 2 bath Single-Family Home with high ceilings 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

$2,750,000

202614756 MLS ⋅ FS - Fee Simple Tenure ⋅ 17 DOM

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, Honolulu

$1,450,000

3 Beds ⋅ 2 Baths ⋅ 202613796 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM

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

$560,000

2 Beds ⋅ 1 Baths ⋅ 202614519 MLS ⋅ FS - Fee Simple Tenure ⋅ 18 DOM ⋅ 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

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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.