Status: Active

Price changed from $1,750,000

Region: Metro

Neighborhood: Tantalus

List Date: 03-28-2026

Address: 4142 Round Top Drive

Land: 17,251

Year Built: 1975

Listing courtesy of Compass

Description: MOTIVATED SELLER. Bring any reasonable offer!! Nestled in lush Tantalus, above the Honolulu cityscape, this 3BD/3BA retreat offers privacy, nature, & modern comfort on a 0.40-acre lot surrounded by tropical greenery. Built in 1975,updated in 1987, it features soaring ceilings, rich redwood walls, & warm wood tones throughout. Its flexible layout includes an open kitchen & 3 living rooms, 1 on each level, making this property ideal for multi-family living. Sunlight pours through large windows, showcasing stunning views, while 31 PV panels with battery backup provide energy efficiency. Sip your morning coffee on one of 3 wrap-around covered lanais, enjoy your fenced garden patio, or play on your flat, terraced yard space—rare for the area—supported by beautiful, newly-engineered rock retaining walls. The detached 2-car garage adds convenience, & the forested setting enhances the serene ambiance of this home. Explore the terrain on your own lot or venture out. You're minutes from Pu'u 'Ualaka'a State Park & hiking trails, yet still close to downtown and schools. This home perfectly balances seclusion & accessibility. A true sanctuary to embrace Hawaii’s beauty & island living!

Status: Active

Region: Metro

Neighborhood: Tantalus

List Date: 06-29-2026

Address: 3330 Tantalus Drive

Land: 606,921

Year Built: 1908

Listing courtesy of Compass

Description: A rare opportunity to acquire an incredible Honolulu estate. Built in 1908 by Alfred Castle, this remarkable 13+ acre Tantalus property has been held by just four distinguished families, Castle, McCandless-Marks, Dillingham lineages, and the estate of Juan Hamilton—renowned artist and protégé of Georgia O’Keeffe. A stately drive welcomes you with eucalyptus trees where expansive lawns evoke the elegance of a bygone era and invite grand outdoor gatherings. Panoramic views from Diamond Head to Haleiwa showcase striking sunsets over the Pacific. Fragrant puakenikeni, jasmine and white ginger bloom amid a landscape of moss rock walls, brick pathways, and wooded trails. The buildings are rich with historic details and distinctive architectural finishes. A 60,000-gallon water catchment system underscores the estate’s blend of heritage and stewardship. More than a residence, this is a landmark property awaiting its next chapter—a chance to reimagine one of Honolulu’s great estates. For those drawn to the intersection of history, nature and place, this extraordinary offering represents far more than real estate. It is a legacy to inherit, shape, and preserve for generations to come.