Diamond Head Homes with Fee Simple Land tenure

Diamond Head Homes with Fee Simple Land tenure

Welcome to Diamond Head, a stunning gem nestled on the southern coast of Oahu, Hawaii. Renowned for its iconic volcanic crater and breathtaking ocean views, this vibrant neighborhood combines the charm of island living with the conveniences of urban life. Just a stone's throw away from the bustling streets of Honolulu, Diamond Head offers a serene retreat while still keeping you connected to the heart of the city.

As you explore this picturesque area, you'll discover a variety of homes that embody the essence of Hawaiian architecture, with lush tropical landscapes and inviting outdoor spaces. One of the most appealing aspects of Diamond Head real estate is the availability of Fee Simple land tenure. This means homeowners enjoy complete ownership of both the property and the land it sits on, providing a sense of stability and security that is highly sought after in Hawaii's competitive market.

Living in Diamond Head means embracing a lifestyle filled with outdoor adventures. From hiking the famous Diamond Head State Monument to enjoying sun-soaked days at nearby beaches, residents have endless opportunities to soak in the natural beauty that surrounds them. The community also boasts an array of local shops, cafes, and restaurants, ensuring you have everything you need right at your fingertips.

Whether you're looking for a cozy cottage or a luxurious oceanfront estate, Diamond Head offers a diverse selection of homes that cater to every taste and budget. Experience the magic of island living in this enchanting neighborhood, where the spirit of aloha thrives in every corner. Discover your dream home in Diamond Head today!

Newest Diamond Head Homes with Fee Simple Land tenure

$1,549,900
3 Beds ⋅ 2 Baths ⋅ 202617753 MLS ⋅ FS - Fee Simple Tenure
Welcome home to your own private island retreat! This well maintained SINGLE LEVEL home is tucked behind a gated entry, offering beautiful tropical landscaping and privacy. Enjoy easy indoor / outdoor living with your large covered lanai, spacious backyard and swimming pool - perfect for gatherings, family fun, or simply relaxing in paradise. This home has 26 photovoltaic panels to keep electricity costs down. Located in desirable Niu Valley you'll be close to East Oahu's beaches, shopping and dining.

5562 Kalanianaole Highway, Honolulu

Listing courtesy of Locations LLC.

$2,095,000
3 Beds ⋅ 3 Baths ⋅ 202616161 MLS ⋅ FS - Fee Simple Tenure
Welcome to 5943 Haleola Street in Niu Valley, one of East Honolulu’s most sought-after neighborhoods, known for its strong sense of community, convenient town location, bikeability, and easy access to shops, dining, beaches, and outdoor recreation. This spacious multi-level home begins with a two-car garage on the ground floor. The second level features two bedrooms, two bathrooms, a laundry room, and a second living area with dedicated office space. The upper level is the showpiece, with high vaulted ceilings, travertine flooring, a massive living area, and sweeping valley and ocean views. The chef’s kitchen features Sub-Zero and Bosch appliances, while the large lanai includes both open-air and enclosed areas for flexible indoor-outdoor living. The oversized primary suite features a large en suite bathroom with both a soaking tub and walk-in shower. With some of the most impressive views in Niu Valley, this is a special opportunity in one of Honolulu’s most desirable neighborhoods. FIRST OPEN HOUSE THIS SUNDAY 3-6PM.

5943 Haleola Street, Honolulu

Listing courtesy of Real Broker.

$2,299,900
7 Beds ⋅ 5 Baths ⋅ 202617522 MLS ⋅ FS - Fee Simple Tenure
Rare Kuliouou opportunity offering beautiful ocean & mountain view, generous living spaces, and exceptional flexibility for multigenerational living! This elegant, turn-key 3 story residence features a 5BD/3BA main home plus a brand-new heater-ideal for extended family or flexible living arrangements. Remodeled and expanded in 2026 the main home features a bright, spacious open-concept kitchen & living area filled with natural light and island breezes. The new kitchen showcases granite countertops, soft-close cabinetry & quality finishes. The main-level primary suite offers large closest and spa-inspired bath with a freestanding soaking tib & shower. Upstairs are 4BD/2BA with beautiful ocean & mountain views. oversized lanais create wonderful indoor-outdoor living spaces for relaxing and entertaining conveniently located near Kuliouou Trail, community parks, basketball & tennis courts, shopping dining and water activities.

597 Papahehi Place, Honolulu

Listing courtesy of Coldwell Banker Realty.

$1,600,000
3 Beds ⋅ 2 Baths ⋅ 202617568 MLS ⋅ FS - Fee Simple Tenure
High above Aina Haina valley, 835 Ahuwale St offers a fully restored home ready for its new owners! The highlight here is the newly-added expansive composite-plank lanai, largely covered and open to steady breezes and stunning ocean and mountain views. Inside, the 3-bedroom, 2-bathroom home feels modern and open. By raising the ceilings throughout the 1,200-square-foot interior, the entire space expands. Classic hardwood floors throughout the main living areas, while both bathrooms feature clean ceramic tile. The layout’s biggest shift from its original 1957 footprint is the massively expanded primary bedroom, which includes a new, ensuite bathroom. The property was recently renovated to upgrade essential infrastructure, including a new roof, and updated plumbing and electrical systems. Outside, the 8,750-square-foot lot provides a spacious backyard anchored by mature mango and plumeria trees. A single-car carport and an additional uncovered space provide parking for two. It is a deeply comfortable home defined by its elevated sight-lines, updated condition, and the beauty of a quiet evening outdoors on the lanai.

835 Ahuwale Street, Honolulu

Listing courtesy of Compass.

$3,395,000
4 Beds ⋅ 4 Baths ⋅ 202617530 MLS ⋅ FS - Fee Simple Tenure
One of the most coveted views on all of Oahu. Unobstructed panoramic ocean views stretch from Koko Head to Diamond Head. Immaculate, ultra-modern, custom-designed estate in Hawaii Loa Ridge. Stylishly renovated with designer landscaping. Soaring ceilings, walls of windows, chef's kitchen w/waterfall counters, & elegant baths. This residence features 4 beds & 4 full baths, stunning living spaces, multiple outdoor lanai areas for effortless indoor/outdoor living. A versatile 1 bd/ 1bath room with a wet bar and separate entry can serve as a second family room or guest quarters. Energy-efficient with newer owned photovoltaic & Tesla Powerwall battery. Beautiful natural light fills the open, airy & breezy floor plan. The primary suite offers a luxury bath w/soaking tub & shower, a true retreat at the end of the day. Recoated roof, 2-car garage, plus a driveway for 5 additional vehicles. A den off the entry could be converted into a bed w/full bath (main level). Hawaii Loa Ridge is Honolulu's most prestigious guard-gated community, offering pickleball courts, clubhouse, 24hr security & ridge trail with rec. area for a truly elevated & active lifestyle right in your backyard.

1179 Ikena Circle, Honolulu

Listing courtesy of Koi Realty.

$348,000
2 Beds ⋅ 2 Baths ⋅ 202617558 MLS ⋅ FS - Fee Simple Tenure ⋅ Kaimuki Jade BLDG.
Kaimuki Jade is located within walking distance to many restaurants, pubs, boutiques, and banks in Kaimuki. Unit recently upgraded: new paint, newer cabinets and counters, bathroom sinks. Coin-Op laundry on each floor. Special Assessment - $413/mo for spalling repairs. Seller offering closing credits for Special Assessment balance.

1139 9th Avenue Unit 304, Honolulu

Listing courtesy of Property Profiles, Inc..

$625,000
1 Beds ⋅ 1 Baths ⋅ 202614971 MLS ⋅ FS - Fee Simple Tenure ⋅ Diamond Head Sands BLDG.
Nestled at the base of Diamond Head this rarely available spacious unit at Diamond Head Sands is one of only eight in the entire community. Enjoy a generous 198 sq ft lanai overlooking lush gardens and a beautiful Monkeypod tree - perfect for relaxing and taking in stunning sunsets while sipping a cool beverage. The spacious bedroom offers an additional closet, while the prime Diamond Head location puts you just minutes from Waikiki's beaches, dining, shopping, Honolulu Zoo, Shell Amphitheater and KCC Farmers Market. Hike world famous Diamond Head Crater and enjoy the spectacular views. Offered AS-IS and priced below assessed value, this is a special opportunity in one of Oahu's most sought-after neighborhoods.

3721 Kanaina Avenue Unit 206, Honolulu

Listing courtesy of LUVA Real Estate.

$2,195,000
2 Beds ⋅ 2 Baths ⋅ 202617486 MLS ⋅ FS - Fee Simple Tenure ⋅ 3056 Kalakaua BLDG.
RARE GOLD COAST PENTHOUSE OPPORTUNITY! Welcome to 3056 Kalakaua, a charming boutique building with only two residences per floor. This highly desirable penthouse showcases expansive ocean and coastline views, spectacular sunsets, and sweeping vistas of Kapiolani Park and iconic Diamond Head. Refreshing breezes flow throughout the residence from the Diamond Head side, creating a truly comfortable island atmosphere. This spacious 2-bedroom, 2-bath residence features a covered lanai, in-unit laundry, a private trash chute, and a charming office nook overlooking the ocean. The pet-friendly building also offers two assigned tandem parking stalls. Just above the penthouse, the rooftop provides breathtaking 360-degree views of Honolulu. Enjoy the world-famous Gold Coast lifestyle, with swimming, surfing, dining, shopping, and the many activities of Kapiolani Park just minutes away. A truly special residence in one of Honolulu’s most coveted oceanfront neighborhoods.

3056 Kalakaua Avenue Unit PHW, Honolulu

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

$3,998,000
6 Beds ⋅ 5 Baths ⋅ 202617452 MLS ⋅ FS - Fee Simple Tenure
Nestled on a quiet, highly sought-after street in prestigious Kahala Diamond, this sophisticated home offers the perfect blend of privacy, luxury, and island living. This exceptional 5-bedroom, 3.5-bath main residence, and a separate studio with full bath, is surrounded by lush tropical landscaping and natural beauty, creating a serene oasis in one of Oahu's most desirable neighborhoods. Set against a dramatic coral hillside, the property features a one-of-a-kind cascading waterfall surrounded by colorful tropical landscaping and mature palms. The thoughtfully designed home offers spacious living areas, excellent bedroom separation, and a flexible layout ideal for family living, entertaining, or multigenerational living. Embrace Hawaii's coveted indoor-outdoor lifestyle with an inviting lanai, private pool and spa, outdoor dining and entertaining areas, and relaxing lounge spaces. Inside, elegant yet comfortable living spaces include a welcoming living room and separate family and dining areas. Enjoy luxurious island living in a beautiful and serene setting on a quiet street, just blocks from the ocean.

542 Ahina Street, Honolulu

Listing courtesy of Anthony L. Pace.

$1,699,000
5 Beds ⋅ 3 Baths ⋅ 202617021 MLS ⋅ FS - Fee Simple Tenure
Maunalani Heights - Multi-generational Opportunity: 5 Bed/3 Bath with ocean & Diamond Head views! Main house offers 3 bedrooms and 2 bathrooms on a single level; 2 bed, 1 bath unit has a separate entrance & in-unit washer/dryer, ideal for rental income and added flexibility. Relax in the hot tub, soak up island living, and enjoy a peaceful, private garden that includes buttery avocados, mango, guava, and kaffir lime. Ample parking with room for 6 cars, including a 2-stall carport. Just minutes to Kaimuki’s boutique shops & popular restaurants, easy freeway access. Close to KCC, UH Manoa & Chaminade.

1898-A Iwi Way, Honolulu

Listing courtesy of REMAX Hawaii.

$8,500,000
5 Beds ⋅ 6 Baths ⋅ 202612765 MLS ⋅ FS - Fee Simple Tenure
This Aukai Avenue residence in Kahala has been remodeled with real intention, not just updated. The floor plan holds five bedrooms, a dedicated office, and multiple gathering spaces across two levels, built for the way people actually live and host in Hawai‘i. On the main level, a formal sitting room, a spacious living room, and an open-concept kitchen with a custom bar open onto a covered lanai set up for formal dining. Two bedrooms on this level lead straight out to the backyard, where a pool, spa, level lawn, and several seating areas do the work of turning outdoor space into living space. Upstairs, three more bedrooms share a second living room, giving the floor its own separation from the rest of the house. The finishes were chosen with care: top-tier appliances, custom closets, built-in cabinetry and shelving throughout. Modern conveniences and amenities include ample storage, a Tesla charger, and a well-equipped gym with a sauna located in one of the main-level bedrooms. Kahala Beach, Waialae Country Club, and the neighborhood's shopping and dining are a short distance away. This is a well-executed renovation in one of Honolulu's most established addresses.

4612 Aukai Avenue, Honolulu

Listing courtesy of Hawaii Life.

$6,750,000
5 Beds ⋅ 4 Baths ⋅ 202617416 MLS ⋅ FS - Fee Simple Tenure
A perfect blend of luxury and casual beach vibe, this gorgeous Diamond Head property sits above the coveted Cromwell's Cove beach, with private deeded beach access just a few doors down. This is the kind of beach property that reminds you why people drop everything to live in Hawaii. The recently completed nearly $1 million remodel includes 2 newly renovated bathrooms, a new library off the main living space, and a brand-new outdoor dining and entertaining area that takes full advantage of Oahu's perfect weather. The pool, hot tub, and kiddie pool is framed by a gated entry, with a beautiful yard for a dreamy entertaining space. There are also net metered PV panels to power everything! The home has 4,096 square feet with 5 bedrooms, 4 bathrooms with an ocean view from the primary suite, which has its own private lanai and room for an office. For surfers, this is a dream location near excellent waves! Sale is subject to seller's replacement property.

245 Palaoa Place, Honolulu

Listing courtesy of eXp 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.