This grand estate on Maui, once owned by the late record producer and A&M Records co-founder Jerry Moss, was clearly crafted for entertaining. The expansive property, situated on a breathtaking stretch of coastline, was initially acquired by Moss in 1995 for $2.5 million. Over the years, he expanded his holdings to include a total of 1.4 acres, purchasing additional parcels in 2000 and later. At that time, Old Makena Road was known for its rustic dirt roads and secluded beaches, but today the area features numerous mansions and beachfront properties.
Now on the market for $39 million, this estate is the most expensive active listing in Hawaii. It boasts 148 feet of beach frontage along Po’olenalena Beach and comprises four homes, built by Moss and his family. These homes include a total of seven bedrooms and seven bathrooms within 6,352 square feet of living space. Despite the high value, the residences are relatively modest in size, each offering a cozy atmosphere and a blend of indoor and outdoor living.
Moss and his wife, Tina, married in 2019, updated the homes with smooth stucco and weather-resistant ipe wood, replacing the original wood siding. Inside, you’ll find teak accents and local materials, including a stone fireplace in the main residence. The decor reflects classic island style with wooden paddles, tiki heads, surfboards, and ukuleles adorning the walls.
The main residence features an open layout with vaulted wood-beamed ceilings, a chef’s kitchen with high-end appliances, and a spacious dining area. A few steps down lead to a cozy living room with panoramic windows offering framed views of the beach and Pacific Ocean. Sliding glass doors open to a covered lanai with a fire pit. The primary bedroom, located upstairs, connects to a covered terrace.
The property also includes an outdoor kitchen with a barbecue, a dining table, and a manicured lawn with tropical foliage and palm trees. The lawn, which features sun loungers and a hammock, offers idyllic views of the beach. Each home is surrounded by lush landscaping for added privacy, with vibrant flowers and native plants lining the pathways.
Additional amenities include a large swimming pool with ocean views, an outdoor lava rock shower with a mosaic wall, and tiki torches for nighttime illumination. Moss and his family, who relocated to Hawaii full-time during the COVID pandemic, have decided to sell and make new memories elsewhere. The property is co-listed by Nancy Callahan of Coldwell Banker Island Properties and Paul Stukin of Deep Blue HI.
Jerry Moss, who co-founded A&M Records with Herb Alpert, managed an impressive roster of artists including Liza Minnelli, Sting, Janet Jackson, and Carole King. Following his passing last year, his family also listed a Bel-Air mansion for $53 million. This home, built in 1937, features five bedrooms and thirteen bathrooms.
