Diamond Head Homes under $2 million

Diamond Head Homes under $2 million

Welcome to Diamond Head, a stunning coastal gem nestled on the island of Oahu, Hawaii. Renowned for its breathtaking landscapes and iconic volcanic crater, this vibrant neighborhood offers a unique blend of natural beauty and urban convenience. With its proximity to the sparkling beaches of Waikiki and the lush greenery of Kapiolani Park, Diamond Head is a paradise for outdoor enthusiasts and beach lovers alike.

As you explore this charming community, you'll discover a variety of homes that embody the spirit of island living. The real estate market in Diamond Head features an array of properties priced under $2 million, making it an attractive option for both first-time buyers and seasoned investors. From cozy single-family homes to modern condos with ocean views, there’s something for everyone in this picturesque locale.

Living in Diamond Head means embracing an active lifestyle. Residents enjoy easy access to hiking trails that lead to the summit of the iconic Diamond Head Crater, where panoramic views of the Pacific Ocean and Honolulu await. The area is also dotted with quaint cafes, boutique shops, and local eateries, providing a delightful blend of convenience and charm.

Whether you’re seeking a serene retreat or a vibrant community, Diamond Head offers the perfect backdrop for your next home. With its stunning scenery and diverse real estate options, it's no wonder that this neighborhood is highly sought after. Discover your dream home in Diamond Head today, and experience the beauty of Hawaiian living at its finest!

Newest Diamond Head Homes under $2 million

3021 Herman Street, Honolulu
$995,000
4 Beds ⋅ 2 Baths ⋅ 202619410 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM
Rare opportunity in St. Louis Heights! Situated on an expansive 9,149 sq ft R-5 zoned lot, 3021 Herman Street offers incredible potential for investors, builders, and buyers looking to create something of their own in the heart of Honolulu. With its generous lot size, desirable zoning, and convenient in-town location, the true value of this property lies in the land and its future possibilities. The existing 4-bedroom, 2-bathroom home offers 1,408 sq ft of interior living space with two separate living areas, a lower level with its own entrance, a covered lanai, and a carport. Surrounded by lush tropical landscaping and mature mango trees, the property provides a peaceful setting with plenty of room to reimagine. Conveniently located just minutes from Kaimuki's popular restaurants, UH Manoa, shopping, and all that town has to offer. Whether you're looking to build your dream home or your next investment, properties with this much land in such a desirable location are hard to come by. Bring your contractor and your vision! Sellers are currently in the process of removing the existing life estate. The property will be conveyed free and clear of the existing life estate at closing.

3021 Herman Street, Honolulu
728 Hanole Place, Honolulu
$1,800,000
6 Beds ⋅ 3 Baths ⋅ 202619185 MLS ⋅ FS - Fee Simple Tenure ⋅ 3 DOM
Nestled on a peaceful private lane in Kaimuki, this charming vintage single-family home offers a rare combination of privacy, timeless character, sweeping views, and an exceptional location. Preserving its 1920s nostalgia with high ceilings and classic beadboard, the residence effortlessly blends historic appeal with relaxed island living. The living room and kitchen flow seamlessly to the lanai and yard, creating an inviting indoor-outdoor space perfect for entertaining or enjoying the cool trade winds. Perched above Ocean View Drive, the property captures panoramic views of Diamond Head, Koko Head, the Koolau Mountains, the ocean, Waikiki and Honolulu city lights, and spectacular sunrises and sunsets. Tucked away from the street yet minutes from Kapiolani Community College, Diamond Head, Kahala Mall, beaches, surfing, shopping, dining, Hawaii Film Studios, and Waikiki, this one-of-a-kind residence captures the essence of old-Hawaii charm and is ready for your final touches!

728 Hanole Place, Honolulu
3824 Leahi Avenue Unit 101, Honolulu
$379,000
1 Baths ⋅ 202619322 MLS ⋅ FS - Fee Simple Tenure ⋅ 4 DOM ⋅ Diamond Head Surf BLDG.
Rarely available ground-floor end unit at Diamond Head Surf, ideally situated in one of Honolulu's most desirable neighborhoods. This charming studio has been refreshed with new mango-wood LVP flooring, ceiling fan, and kitchen window, creating a bright, inviting space with a relaxed island feel. Enjoy the cross-breezes and abundant natural light, with lush tropical landscaping just outside your door. This boutique, mid-century building offers an on-site swimming pool, BBQ area, bike racks, and community laundry facilities, all in an exceptional location a quick walk to Kapiolani Park, Honolulu Zoo, Waikiki Shell, and some of Oahu’s most beautiful beaches. Whether you're looking for a convenient island retreat or a place to call home, this is a wonderful opportunity to enjoy the Diamond Head lifestyle.

3824 Leahi Avenue Unit 101, Honolulu
3015 Kalakaua Avenue Unit 902, Honolulu
$1,595,000
1 Beds ⋅ 2 Baths ⋅ 202618550 MLS ⋅ FS - Fee Simple Tenure ⋅ 5 DOM ⋅ Oceanside Manor BLDG.
Enjoy beautiful ocean and Diamond Head views along with comfortable trade winds from this 1 bedroom, 1.5 bath unit which features a large walk-in closet (formerly the 2nd bedroom). Oceanside Manor has only 2 units per floor, with one assigned parking, pet-friendly, storage unit, secured surfboard rack and private beach access. Live a lifestyle like no other on the Gold Coast of Oahu where you are just minutes away from Kapiolani Park, Waikiki Shell, entertainment, shopping, dining, a variety of ocean sports and the best of Waikiki and Diamond Head has to offer.

3015 Kalakaua Avenue Unit 902, Honolulu
4188 Keanu Street Unit 4, Honolulu
$685,000
2 Beds ⋅ 2 Baths ⋅ 202619163 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM ⋅ Tropic Gardens 1 BLDG.
Renovated top to bottom in 2023, this 2-bedroom, 2-bath split-level townhome in the Tropic Gardens offers 1,032 sf of interior living space in the renowned Waialae-Kahala neighborhood. The expanded open concept kitchen centers on a large island with seating, so no dining table is needed, & pairs stone & butcher block countertops with stainless steel appliances. Vinyl plank flooring & a blend of modern & farmhouse finishes run throughout. Downstairs holds the kitchen, living room & a full bath; upstairs, both bedrooms & a second full bath. A loft attic adds ample storage. Split ACs & ceiling fans. One assigned open parking stall. Tropic Gardens offers a swimming pool, grassy spaces throughout & a great resident manager. The well-funded project is midway through a master beautification program: one-third already has new landscaping, new roofs & fresh paint, & this unit is in the second phase. The work is fully funded by reserves with no assessment to owners. Across the street from Kahala Mall & within a half block of shops, restaurants, grocery stores & urgent care, near bus lines & freeway access. Zoned for Wilson Elementary, Kaimuki Middle & Kalani High. Open this Sun 10/18, 2-5pm

4188 Keanu Street Unit 4, Honolulu
1426 Laamia Street, Honolulu
$1,895,000
3 Beds ⋅ 2 Baths ⋅ 202619176 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM
Beautiful Views from this Two Story 3 Bedroom 2 Bath Single Family Home on Lower Waialae Iki. Raised Ceilings in Living/Family Room. Large Open Decks to enjoy the enchanting Sunsets! Two Car Enclosed Garage with High Ceilings for Extra Storage Area! Newer Roof (2021). Kidney Shape Swimming Pool in Private Backyard! Convenient Access to Freeways going both East and/or West! Home needs updating.

1426 Laamia Street, Honolulu
1952 Bertram Street, Honolulu
$1,565,000
3 Beds ⋅ 3 Baths ⋅ 202619233 MLS ⋅ FS - Fee Simple Tenure ⋅ 6 DOM
Sunday Open House 10/18/26 2-5p. STUNNING Diamond Head, ocean, coastline, and city views set the stage for this tastefully renovated and meticulously maintained 3-bedroom, 2.5-bath residence in the highly sought-after St. Louis Heights neighborhood. Over $400,000 invested over the past 12 years in thoughtful improvements and ongoing maintenance, showcasing true pride of ownership. A permitted addition completed in 2017 enhanced the home with: A spacious front deck designed to capture the breathtaking views; An accessory wet bar ideal for entertaining; and An additional full bathroom—adding both functionality and value. The terraced backyard is a peaceful retreat featuring apple banana, papaya, dragon fruit, lime, along with other plantings, perfect for gardening or relaxing outdoors. This is a home that truly must be seen in person to appreciate the quality, care, and attention to detail throughout. Conveniently located with easy access to the freeway, iconic Kaimuki Town, Waikiki, beaches, dining, and shopping. 2025 Permitted 200 amp electrical upgrade completed. Click the Virtual Tour tab to experience the spectacular sunset video with drone footage.

1952 Bertram Street, Honolulu
1123B 2nd Avenue, Honolulu
$749,000
2 Beds ⋅ 1 Baths ⋅ 202619218 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM
Charming Kaimuki cottage in the Heart of Honolulu minutes to Ala Moana, Waikiki, and Kahala shops and restaurants. This 2-bedroom 1-bath remodeled residence is move in ready. Features new hardwood cabinets & quartz counter tops, new appliances, new luxury vinyl flooring, new tub & surrounds, new toilet & vanity and new fixtures throughout. Comes with a dedicated parking stall and additional street parking. An ideal alternative to condo living with no maintenance fees. Close to the University of Hawaii at Manoa, Punahou, Iolani and down the street from Chaminade University and St. Louis School. Experience the best of Kaimuki with an affordable single family home.

1123B 2nd Avenue, Honolulu
4036 Koko Drive, Honolulu
$1,850,000
3 Beds ⋅ 2 Baths ⋅ 202617419 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM
Breathtaking ocean and coastline views take center stage in this fully remodeled residence, ideally situated in the highly sought after Wilhelmina Rise neighborhood. This spacious, open concept floor plan is thoughtfully designed for modern living and features a large kitchen island, elegant quartz countertops, and stainless-steel appliances. Additional highlights include a leased photovoltaic system for enhanced energy efficiency, multiple split AC units, and a convenient ground floor primary suite that features an expansive layout complete with a private en-suite bathroom and an exceptionally spacious walk-in closet. A versatile storage room offers the perfect space for a home workshop, hobby area, or additional storage space. This exceptional home offers the perfect blend of comfort, convenience, and island living - Making it an ideal sanctuary for those seeking a premium lifestyle in one of Honolulu's most desirable neighborhoods. With its seamless indoor-outdoor flow and meticulous attention to detail, this property stands as a premier opportunity in the current market. 1st Open House - Sunday: October 18, 2026 from 2-5 p.m.

4036 Koko Drive, Honolulu
5340 Opihi Street, Honolulu
$1,699,000
6 Beds ⋅ 5 Baths ⋅ 202613779 MLS ⋅ FS - Fee Simple Tenure ⋅ 7 DOM
LOCATION, SPACE & OPPORTUNITY! An incredible opportunity on highly sought-after Opihi Street in the heart of Aina Haina. Situated on an expansive 10,235 sq. ft. lot, this spacious home offers an incredible amount of living area and flexible options for extended or multi-generational living, or explore the potential for an ADU. Even more special—the backyard opens directly to a small, hidden neighborhood park, creating a wonderful extension of your outdoor space. Just blocks from the ocean and Aina Haina Shopping Center, with restaurants, schools and everyday conveniences nearby. The seller began renovations with plans to transform the property, but plans changed before completion. Now it’s your opportunity to bring your contractor and your vision, finish it your way and unlock the tremendous potential of this property. Large lot, incredible space and a phenomenal location—an opportunity like this on Opihi Street doesn’t come along often! No Public Open House. Shown by Appointment Only.

5340 Opihi Street, Honolulu
2937 Kalakaua Avenue Unit 28, Honolulu
$975,000
1 Beds ⋅ 1 Baths ⋅ 202618916 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM ⋅ Castle Surf Apts BLDG.
NEW LISTING!! Rarely available on Honolulu’s iconic Gold Coast, this beautifully updated 1-bedroom, 1-bath residence at Castle Surf offers the opportunity to own in one of Oahu’s most coveted coastal settings. With 1 covered parking stall, the unit features fresh interior paint, an open floor plan, stainless steel appliances, and a covered lanai for enjoying the tropical surroundings. Exceptionally clean and move-in ready, this residence offers private direct access to the Pacific Ocean and an incredible coastal lifestyle. Ideally located just moments from Kapiolani Park, Kaimana Beach, and world-famous Waikiki Beach, with an array of restaurants, shopping, entertainment, and outdoor activities nearby. A wonderful opportunity to own a well-kept residence in one of Honolulu’s most sought-after coastal neighborhoods.

2937 Kalakaua Avenue Unit 28, Honolulu
4958 Kilauea Avenue Unit 57, Honolulu
$625,000
2 Beds ⋅ 2 Baths ⋅ 202619028 MLS ⋅ FS - Fee Simple Tenure ⋅ 10 DOM ⋅ Waialae Gardens BLDG.
An updated cute townhome ... very clean, freshly painted, newer floors, new bathroom shower , kitchen renovated a few years ago, some new appliances ... being sold furnished ...Nestled in prime Kahala location ... close to freeway entrance. Enjoy convenience with just a short walk to shopping, dining, schools... Don't miss this opportunity... Vacant and easy to see.

4958 Kilauea Avenue Unit 57, Honolulu
Start Your Search

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.

How much is your home worth?

Get instant property value now!