Nestled across some of Hawaii’s most coveted landscapes, from the serene shores of Makena to the lush heights of Hualalai, these five exceptional homes redefine desirable living. Priced between $1,950,000 and $4,500,000, each property offers a unique blend of privacy, panoramic ocean views, and sophisticated design. Whether it’s a sprawling luxury estate or a bright, open single-level retreat, these residences capture the essence of island elegance, promising an unparalleled lifestyle amid tropical beauty and tranquil surroundings.
5 Acre Gentlemans Farm With ResortLike Home | $4,500,000


Sharly Ward & Kelly Shaw

Sharly Ward & Kelly Shaw
Set against the stunning waterfront of Wehilani, this rural estate captures breathtaking ocean vistas while offering unparalleled privacy. Spanning 2,959 square feet, the single-level home, built in 2002 and thoughtfully remodeled in 2023, boasts a bright, open layout. Elegant mango wood cabinetry, quartz countertops, slate floors, and wood pocket doors seamlessly connect to a sprawling 1,200-square-foot covered lanai. Outside, a saltwater pool and hot tub invite relaxation, while terraced grounds feature 340 coffee trees and a vibrant orchard with mango, lychee, avocado, and more. A detached garage with a carport, storage, and art studio sparks creative inspiration. Sustainability shines with 28 owned solar panels, net metering, and solar pool heating. With an approved site for a future farm dwelling, this rare Kona retreat harmonizes luxury and eco-conscious living amid tropical splendor.
Size: 5.00 acres
- Price:
- $4,500,000
- Contact:
- Sharly Ward & Kelly Shaw, Compass, 808.938.9533 , 808.960.4636
734695 Pilialoha Road | $4,488,000


Karen Ferrara

Karen Ferrara
Set against the breathtaking backdrop of panoramic ocean views, this 7,068-square-foot luxury estate on Hualalai offers an unparalleled blend of privacy and tropical elegance. Spanning 3 lush acres, the 5-bedroom, 6-bath retreat showcases exquisite craftsmanship with 12-to-19-foot beam-trussed ceilings, a double-sided fireplace, and mahogany pocketing doors that reveal an expansive lanai. The gourmet kitchen impresses with rare Van Gogh countertops and premium appliances, while the primary suite indulges with a spa-style bath and outdoor shower. Beyond the main living spaces, a private downstairs area features a Dolby sound theater and yoga space, complemented by a detached guest cottage. Surrounded by a fruitful orchard of mango, avocado, and citrus, the flat land invites outdoor events or future expansion. Just 7 minutes from Pine Trees Beach, this Big Island haven in the Holualoa school district redefines waterfront serenity.
- Price:
- $4,488,000
- Size:
- 7,068 sq ft
- Contact:
- Karen Ferrara, Ferrara & Co., 808.883.0094
Paradise Found An Exceptional Opportunity To Live Polo | $4,050,000


Phylleen P. Jackson

Phylleen P. Jackson
Set against the serene backdrop of Maui’s stunning coastline, Polo Beach Club 408 offers an unparalleled waterfront lifestyle. This exquisite hotel-zoned vacation rental redefines elegance with a meticulously remodeled interior. The open gourmet kitchen boasts a granite island with bar seating, top-tier appliances, and custom cabinetry sourced from the mainland. Travertine flooring flows throughout, accented by thoughtfully selected area rugs and runners, while handpicked furnishings and artwork create a seamless blend of sophistication and comfort. The reconfigured primary bedroom and bath serve as a luxurious, private retreat, and the guest bedroom features custom-built cabinets with a dedicated desk space. Step onto the spacious lanai, perfect for living and dining, where breathtaking ocean views and direct beach access remind you why Maui captivates the soul. This residence embodies coastal refinement at its finest.
- Price:
- $4,050,000
- Size:
- 1,186 sq ft
- Contact:
- Phylleen P. Jackson, Coldwell Banker, 808.385.1336
721154 Hoopai Rd | $2,400,000


Randy Ripley

Randy Ripley
Set against the serene backdrop of a waterfront haven, this enchanting custom home resides within the exclusive gated community of Makalei Estates. Spanning three fully fenced and cross-fenced acres, the property ensures privacy and security, with an electric gate guarding the entrance. A striking lava paver driveway guides you to an elegant porte-cochère, adorned with bespoke lighting that sets a warm, inviting tone. Step through the custom handmade doors, imported from Turkey, into a grand entryway where sweeping ocean views unfold through an open floor plan. Every detail of this home reflects thoughtful craftsmanship, offering a seamless blend of luxury and nature. Ideal for those seeking tranquility, this estate provides ample space for outdoor pursuits or simply soaking in the calming waterfront vistas, creating a lifestyle of unparalleled peace and sophistication in a truly magical setting.
- Price:
- $2,400,000
- Size:
- 2,384 sq ft
- Contact:
- Randy Ripley, Compass, 808.209.6244
78118 Holuakai St | $1,950,000


Kristina Vaughn-Hazard

Kristina Vaughn-Hazard
Situated within the prestigious gated community of Holua Kai at Keauhou, this exceptional residence offers an idyllic lifestyle right on the edge of Keauhou Bay. The home seamlessly blends indoor and outdoor living, with pocket doors opening to a spacious lanai where gentle breezes and scenic views become part of daily life. Inside, resort-inspired tray-style ceilings and elegant stone flooring create an atmosphere of sophistication and comfort. Thoughtful upgrades enhance the property’s appeal, including a whole-house water conditioning system, high-efficiency air conditioning, and a fully owned photovoltaic system for sustainable living. Perfectly designed for relaxation or entertaining, this home captures the essence of island living in a secure, exclusive setting. Whether enjoying quiet mornings or hosting gatherings, residents benefit from a serene environment that prioritizes both luxury and convenience in one of Hawaii’s most coveted locations.
- Price:
- $1,950,000
- Size:
- 1,888 sq ft
- Contact:
- Kristina Vaughn-Hazard, Compass, 808.895.1364











