Diamond Head Homes with Leasehold Land tenure

Diamond Head Homes with Leasehold Land tenure

Welcome to Diamond Head, one of Honolulu's most iconic and sought-after neighborhoods, nestled on the southeastern coast of Oahu. Known for its stunning volcanic crater and breathtaking ocean views, Diamond Head combines natural beauty with a vibrant local culture, making it an ideal destination for those seeking a unique Hawaiian lifestyle.

This enchanting area is characterized by its lush landscapes, pristine beaches, and a strong sense of community. Residents enjoy a plethora of outdoor activities, from hiking the famous Diamond Head State Monument to surfing at the nearby beaches. The local dining scene is equally impressive, featuring a variety of restaurants that serve everything from traditional Hawaiian cuisine to international fare.

When it comes to real estate, Diamond Head offers a diverse range of properties, including charming homes on leasehold land. Leasehold land tenure is an attractive option for many buyers, as it often provides access to prime locations at a lower entry price. With leasehold properties, homeowners purchase the home while leasing the land from the landowner, typically for a long-term period. This arrangement can be ideal for those who wish to enjoy the beauty and lifestyle of Diamond Head without the higher costs associated with freehold properties.

Whether you are looking for a cozy bungalow or a luxurious oceanfront condo, Diamond Head has something for everyone. Immerse yourself in the vibrant culture, stunning scenery, and welcoming community of this remarkable neighborhood. Discover your dream home in Diamond Head, where paradise meets everyday living!

Newest Diamond Head Homes with Leasehold Land tenure

$150,000
2 Beds ⋅ 2 Baths ⋅ 202614285 MLS ⋅ LH - Leasehold Tenure ⋅ Kahala Beach BLDG.
This spacious, garden-view gem in prestigious Kahala is beautifully renovated and move-in ready! Featuring 2 bedrooms, 2 baths, 1 covered parking stall, an open floor plan, and an enclosed lanai, this home is just steps from a sandy beach, Kahala Mall, and the iconic Kahala Hotel. Enjoy direct beach access with a protective offshore reef, offering calm waters for swimming, snorkeling, diving, and paddleboarding. Experience the best of island living. Lease expires July 15, 2027.

4999 Kahala Avenue Unit 422, Honolulu

Listing courtesy of REMAX Hawaii.

$495,000
3 Beds ⋅ 3 Baths ⋅ 202614329 MLS ⋅ LH - Leasehold Tenure ⋅ Kahala Beach BLDG.
Experience luxury BEACHFRONT living in prestigious KAHALA! This stunning 3b/3b residence offers direct beach access w/a protective offshore reef, creating calm waters ideal for swimming, snorkeling, diving & paddleboarding. Enjoy unobstructed OCEAN & KOKO HEAD views from the spacious enclosed lanai. Highlights incl: HARDWOOD floors, soaring ceilings, custom cabinetry, central A/C, Sub-Zero & Bosch appliances, wine refrigerator, built-in bookshelves & speakers, Toto toilets, dual water heaters & Water Guard sensors. Rare opportunity to own this beachfront paradise! Lease expires July 15, 2027.

4999 Kahala Avenue Unit 472, Honolulu

Listing courtesy of REMAX Hawaii.

$80,000
2 Beds ⋅ 2 Baths ⋅ 202607653 MLS ⋅ LH - Leasehold Tenure ⋅ Kahala Beach BLDG.
Lease rent paid through September 2026! Perched on the 2nd floor with stunning views of Kahala Beach and the Pacific Ocean, this move-in-ready corner-end condo has been thoughtfully maintained and features upgrades such as updated kitchen and bathrooms, vinyl plank flooring, stainless steel appliances, quartz counters, upgraded cabinets, tiled lanai, plantation shutters and central AC. The covered lanai, framed by floor-to-ceiling glass doors, invite in gentle trade winds and sweeping views of the beach and ocean—an ideal setting for outdoor dining under the stars and moonlight. Bright and inviting, the unit reflects true pride of ownership. This is a leasehold property with a lease expiration date of July 15, 2027, and no option to purchase the fee. Property currently unfurnished; photos taken when previously occupied.

4999 Kahala Avenue Unit 252, Honolulu

Listing courtesy of Five Star Realty, Inc..

$900,000
2 Beds ⋅ 2 Baths ⋅ 202600206 MLS ⋅ LH - Leasehold Tenure ⋅ Sans Souci Inc BLDG.
Experience classic Gold Coast living at Sans Souci. This wonderfully maintained high-floor residence enjoys a view plane that clears the Kaimana Beach Hotel, opening to ocean, palms, and cool tradewinds. The flexible layout lives like a spacious 1-bedroom, with an additional area perfect for guests, office, or a sleeping alcove. A smart opportunity for those who appreciate value - Why tie up millions of dollars in paying for a Fee Simple $3,000,000+ condo when you can buy this $900,000 Leasehold condo that offers a much more affordable way to enjoy the same lifestyle - even with lease rent and maintenance fees (inclusive of taxes, insurance and utilities). Ask us for the breakdown! Plus, the potential to generate income that helps offset monthly fees while still enjoying this unmatched lifestyle location. Currently rented with a 30-day minimum stay requirement. Beloved oceanfront building steps to Kaimana Beach, Outrigger, Kapiolani Park, and Waikiki dining. A special offering combining location flexibility, and oceanfront living.

2877 Kalakaua Avenue Unit 1107, Honolulu

Listing courtesy of Hawaii Modern Realty.

$275,000
3 Beds ⋅ 2 Baths ⋅ 202601168 MLS ⋅ LH - Leasehold Tenure ⋅ Kahala Beach BLDG.
Kahala luxury living in this highly upgraded, single-level ground floor residence with over 2,000sf. This renovated 3 bedroom, 2 bath home is located in sought after oceanfront Kahala Beach condominium just steps from The Kahala Hotel & Resort and Waialae Country Club. Spacious interiors and mountain views. Features include hardwood flooring, a large galley kitchen with granite countertops and custom cabinetry, and elegant baths with backlit onyx countertops, travertine flooring, Toto toilets and premium fixtures. Wine enthusiasts will love the 6 integrated wine vaults with 400-500 bottle capacity. Additional highlights include custom built-in Chinese elm panels for storage, custom window coverings, and Baldwin hardware, reflecting thoughtful design and exceptional craftsmanship. A beautiful sandy beach fronts the building; amenities include a heated pool, exercise room and security. This is a leasehold property. Your opportunity for an unparalleled lifestyle!

4999 Kahala Avenue Unit 101, Honolulu

Listing courtesy of Coldwell Banker Realty.

$175,000
1 Baths ⋅ 202518765 MLS ⋅ LH - Leasehold Tenure ⋅ Diamond Head Bch Hotel BLDG.
OCEAN FRONT ~ GOLD COAST Diamond Head Beach Hotel & Residence is the only building on the Gold Coast that offers legal vacation rentals. Great rental income potential and enjoy the condo amenities at your leisure. Currently owner-managed on vacation rental platforms with the option to use the on-site Hotel Management with front desk operations. Enjoy the beautiful ocean front tropical landscaped grassy lawn. Direct access to the ocean for swimming and sporting. Sans Souci is near-by for beach activities with life-guard. Kapiolani park offers community tennis/pickle ball courts and events. Elk's and Outrigger Canoe Club are next-door along with the Waikiki Aquarium and fine dining. Diamond Head is close enough to enjoy all of Waikiki yet is more of a serene neighborhood embraced with the spirit of Aloha. Plenty of street parking free/metered is available and also gated garage parking (fee). Security guard on-site nightly, FOB gated access, security cameras and fire sprinklers. Showings by appointment subject to bookings. This is a Lease-Hold property, contact Listing Agent for more information. ~Mahalo

2947 Kalakaua Avenue Unit 302, Honolulu

Listing courtesy of Hawaii Americana Realty.

$300,000
202505404 MLS ⋅ LH - Leasehold Tenure
Well-established and beloved authentic Japanese restaurant, proudly serving the community since 2000. Situated in the heart of the popular Kaimuki neighborhood, this local favorite has built a strong reputation, attracting a dedicated base of loyal customers. Turn-key, ready for seamless ownership transition. Sale is subject to landlord approval. Lease is NNN, with the listed rent reflecting base rent only.

3565 Waialae Avenue Unit 108, Honolulu

Listing courtesy of Coldwell Banker Comm 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.