Diamond Head Homes with City View

Diamond Head Homes with City View

Welcome to Diamond Head, a breathtaking gem nestled on the southeastern coast of Oahu, Hawaii. Known for its iconic volcanic crater and stunning coastal vistas, this vibrant neighborhood in Honolulu offers an extraordinary lifestyle that seamlessly blends natural beauty with urban convenience.

Diamond Head is not just a picturesque landmark; it’s a thriving community rich in culture and history. Residents enjoy easy access to some of the island's most beautiful beaches, lush hiking trails, and a variety of outdoor activities. The famous Diamond Head State Monument invites you to explore its scenic trails, leading you to panoramic views that will leave you in awe. Imagine waking up each day surrounded by the serene beauty of the Pacific Ocean and the majestic mountains.

The real estate market in Diamond Head is as diverse as its landscape. Homes here often boast stunning city views, allowing residents to bask in the vibrant sunsets and twinkling lights of Honolulu. Whether you’re looking for a luxurious oceanfront property or a charming bungalow nestled in the hills, Diamond Head offers a unique selection of homes that cater to every lifestyle.

Living in Diamond Head means embracing a laid-back island lifestyle while still being close to the bustling heart of Honolulu. With trendy shops, gourmet dining, and cultural attractions just a short drive away, you can enjoy the best of both worlds. Discover the magic of Diamond Head, where every day feels like a vacation and your dream home awaits amidst breathtaking views and a welcoming community.

Newest Diamond Head Homes with City View

$2,750,000
202613984 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. Includes TMKs 1-3-3-032-031-0001 and 1-3-3-032-031-0002.

3950 Sierra Drive, Honolulu

Listing courtesy of Caron B Realty.

$1,737,000
7 Beds ⋅ 3 Baths ⋅ 202614441 MLS ⋅ FS - Fee Simple Tenure
GREAT SCHOOL DISTRICTS! WAIKIKI ELEMENTARY/ KAIMUKI MIDDLE/KALANI HIGH! MULTI-DWELLING IN KAPAHULU! Front house is a 2 story-- 2/1 upper & 2/1 lower. Back house is a 3/1. It has 3 electric meters & 3 gas meters. All tenants occupied. Renovated in 2022 includes new kitchens, bathrooms, flooring and paint. Please don't walk on property or disturb tenants.

3429 Wela Street, Honolulu

Listing courtesy of Realty Prime LLC.

$1,737,000
202614436 MLS ⋅ FS - Fee Simple Tenure
GREAT SCHOOL DISTRICTS! WAIKIKI ELEMENTARY/KAIMUKI MIDDLE/KALANI HIGH!!! MULTI-DWELLING IN KAPAHULU! Front house is a 2-story--2/1 upper & 2/1 lower. Back house is a 3/1. It has 3 electric meters & 3 gas meters. All tenants occupied. Renovated in 2022 includes new kitchens, bathrooms, flooring and paint. Please don't walk on property or disturb tenants.

3429 Wela Street, Honolulu

Listing courtesy of Realty Prime LLC.

$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. Effective Year Built 1970). 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, Wine Cellar, 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.

$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.

$3,590,000
2 Beds ⋅ 2 Baths ⋅ 202613818 MLS ⋅ FS - Fee Simple Tenure ⋅ Coral Strand Ltd BLDG.
Experience refined Gold Coast living in this beautifully crafted oceanfront residence at Coral Strand Ltd. Perfectly positioned above the canopy of Kapiolani Park, this exceptional home captures breathtaking panoramic views of the Pacific Ocean, Diamond Head, the Honolulu skyline from three private lanais. Expertly remodeled by renowned contractor John Sutton, the residence showcases timeless design, exceptional craftsmanship, and premium materials throughout. European limestone flooring, exquisite marble bathrooms, hand-finished teak accents, custom walnut cabinetry, and soaring 9-foot ceilings create an elegant and sophisticated living environment. The gourmet kitchen is appointed with Miele, Bosch, and Sub-Zero appliances, while a wet bar, Lutron lighting and automated shades, Sonos sound system, dual-zone central air conditioning, and an in-unit washer and dryer provide modern comfort and convenience. Residents enjoy secure underground parking, private storage, a heated saltwater pool, and direct access to one of Oahu's most desirable coastal settings. Just moments from Kapiolani Park, Waikiki and world-famous beaches, this is island living at its finest.

2979 Kalakaua Avenue Unit 904, Honolulu

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

$1,425,000
3 Beds ⋅ 2 Baths ⋅ 202613311 MLS ⋅ FS - Fee Simple Tenure
Welcome to 1568 Halekoa Drive in desirable Waialae Nui Ridge! Ideally located in town and not too far up the hill, this well-maintained 3-bedrm, 2-bath family home has been cared for by the same owner over the years and is ready for its next chapter. Freshly painted interior and ceilings give the home a clean, bright feel while allowing the next owner to update and personalize. Enjoy tradewind breezes and peekaboo ocean and Diamond Head views from the balcony, front of the home, and select windows. Designed for everyday living, the floor plan includes a living room, rumpus room, kitchen, enclosed utility/washroom area, and large basement/flex area with stairs—ideal for storage, hobbies, home office, game room, study area, or creative space. A rare bonus for hillside living, the property offers a level yard, 2-car carport/garage with storage, generous under-house storage, and workshop area. Front yard has red and yellow hibiscus; backyard has coconut, mango, and lychee trees providing afternoon shade. Roof replaced in 2010 and recently tented with transferable warranty. Convenient to Kahala Mall, Kaimuki, schools, parks, restaurants, and freeway access. 1st OH Sunday, 7/19, 2-5pm.

1568 Halekoa Drive, Honolulu

Listing courtesy of REMAX Hawaii.

$1,350,000
6 Beds ⋅ 2 Baths ⋅ 202613125 MLS ⋅ FS - Fee Simple Tenure
Rare opportunity to secure a premier redevelopment site in the prestigious Wilhelmina Rise neighborhood. Situated on an expansive 11,017 sq. ft. lot with breathtaking panoramic views of the city skyline, ocean, mountains, sunsets, and iconic Diamond Head, this property is a true value-add opportunity for investors, builders, developers, and contractors. The existing 6-bedroom, 2-bath residence (approximately 2,532 sq. ft., built in 1962) is in very poor condition, with the structure conveying zero value and offered strictly As-Is. Bring your vision and explore the possibilities to reimagine this exceptional homesite in one of Honolulu's most established neighborhoods. Conveniently located near parks, restaurants, shopping, grocery stores, and everyday conveniences. CAUTION: Property may present safety hazards. Interior access is limited and not recommended without appropriate precautions. Do not enter or access the property without prior approval. Buyer to conduct their own due diligence. Opportunities like this are rare—contact your REALTOR® today for more information.

4326 Sierra Drive, Honolulu

Listing courtesy of ENRG Realty.

$1,488,000
14 Beds ⋅ 6 Baths ⋅ 202613187 MLS ⋅ FS - Fee Simple Tenure
The property features five separate residential units, in beautiful Palolo Valley, providing immediate income and a compelling value-add investment opportunity. Priced to reflect its current condition, including existing water intrusion and significant repair needs, this offering provides investors the opportunity to acquire a multi-unit asset at a substantial discount. With renovation and repositioning, the property offers meaningful upside through increased rental income and long-term appreciation.

2001 10th Avenue, Honolulu

Listing courtesy of CBI Residential Advisory Svcs..

$3,499,500
4 Beds ⋅ 4 Baths ⋅ 202613054 MLS ⋅ FS - Fee Simple Tenure
Rim lot. Stunning view. Refrigerator, washer and dryer, dishwasher, two split air conditioner, salt water pool, two water heaters, two ceiling fans, remote controlled window coverings, remote controlled garage door, Photovoltaic system with two back up Tesla batteries. Sold "as is"

1728 Kumakani Loop, Honolulu

Listing courtesy of Young Hawaii Homes, Inc..

$1,750,000
5 Beds ⋅ 2 Baths ⋅ 202613079 MLS ⋅ FS - Fee Simple Tenure
Discover a rare opportunity in the highly desirable St. Louis neighborhood! This versatile 5-bedroom property features a legal, permitted ADU, offering flexibility for multi-generational living, extended family, guests, or potential rental income! Enjoy the ocean and Diamond Head views from your upper lanai while sipping your morning coffee. The remodeled lower level showcases modern finishes and updated living spaces, while the home's functional layout provides room for a variety of living arrangements. Whether you're looking for additional privacy, space to work from home, or an income-producing opportunity, this property delivers. Back side of the backyard borders State land, providing an added sense of privacy with no neighboring home along that boundary. Conveniently located to UH Manoa, Waikiki, Kaimuki, shopping, dining, parks, and freeway access, you'll enjoy neighborhood charm and town convenience. Don't miss the chance to own this unique St. Louis home with endless possibilities!

1938 Bertram Street, Honolulu

Listing courtesy of Century 21 Island Homes.

$2,200,000
3 Beds ⋅ 3 Baths ⋅ 202612638 MLS ⋅ FS - Fee Simple Tenure
Perched on the highly coveted Waialae Nui Ridge, one of Honolulu's most desirable ridge communities, this beautifully renovated home offers the perfect blend of comfort, convenience, and breathtaking views. Enjoy Diamond Head, city skyline, and stunning sunset vistas from the spacious lanai, all while living just minutes from the Honolulu metro area, shopping at Kahala Mall, dining, beaches, and much more. Situated along a relatively flat street in a walkable area of the ridge, this 3-bedroom, 2.5-bath residence offers a thoughtfully designed living space featuring exposed beam ceilings, a spacious kitchen, and an open inviting layout. Recent upgrades include luxury vinyl plank flooring throughout, updated appliances, Taj Mahal quartz kitchen countertops, California Closets storage, fresh interior and exterior paint, and low-maintenance Trex decking. Energy-efficient features include an owned 10-panel photovoltaic system on Net-Metering, and a solar hot water heater. Complete with a spacious yard, two-car garage, and access to the Waialae Ridgeline community center with pool, this exceptional home truly has it all.

2544 Halekoa Drive, Honolulu

Listing courtesy of Paradise Real Estate Brokers.

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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.