Imagine waking up to the sound of crashing waves or gazing at endless ocean horizons from your own slice of paradise. Across Hawaii’s most coveted locations, from Wailea to Oahu’s North Shore, four extraordinary properties await, priced between $2.45M and $5.25M. Each offers a seamless blend of luxury, modern design, and nature’s splendor—think beachfront access, resort-style amenities, and sweeping views. Whether it’s a serene villa or a custom-built retreat, these homes embody the tropical lifestyle, inviting you to surf, hike, or simply soak in the island’s timeless beauty.
24 Ho’olei Circle | $5,250,000


Katy Foxwell

Katy Foxwell
Positioned along the serene waterfront of Wailea, this luxury resort villa at Ho’olei offers an unparalleled connection to the beauty of Maui. Just steps from Grand Wailea and Wailea Beach, the split-level townhome, unit T-1, spans an impressive 3,076 square feet of refreshed indoor space, complemented by a generous 700-square-foot covered lanai. As the largest Hibiscus floor plan in a coveted end-unit location, it maximizes privacy and biophilic design. Residents enjoy access to a lush tropical pool with a dramatic 19-foot waterfall, a swim-in grotto, whirlpool spas, and a children’s pool with a sandy beach entry. Additional amenities include BBQ areas, a poolside kitchen and pavilion, a state-of-the-art fitness facility, saunas, and locker rooms. Surrounded by world-class resorts, dining, beaches, golf, tennis, and shopping, this beautifully appointed, furnished villa embodies the essence of island living.
- Price:
- $5,250,000
- Size:
- 3,076 sq ft
- Contact:
- Katy Foxwell, Keller Williams Realty Maui-Ka, 808.385.0882
59535 Ke Iki Rd A | $4,700,000


Gina M Overton

Gina M Overton
Positioned along the iconic 7-mile miracle of Oahu’s North Shore, this custom-built waterfront residence on Ke Iki Beach offers an unparalleled beachfront lifestyle. With the expansive white sands just steps away, the reverse floor plan thoughtfully places the living, kitchen, and dining areas on the second floor, maximizing ocean vistas and inviting trade winds through a spacious covered lanai. An office adds versatility to the space. On the first floor, three bedrooms await, including an en-suite with a separate entrance, complemented by two additional bathrooms and a cozy den with direct beach access. Modern touches like tinted windows, split AC units, and 20 photovoltaic panels enhance comfort and efficiency. Outside, landscaped grounds feature lush lawns, fragrant flowers, fruit trees, and swaying palms, while seasonal surfing, snorkeling, and whale watching unfold at your doorstep. Proximity to Haleiwa Town and Waimea Falls Park adds convenience to this serene coastal retreat.
- Price:
- $4,700,000
- Size:
- 2,145 sq ft
- Contact:
- Gina M Overton, Compass, 808.226.1729
Stunning Views | $3,995,000


David Quandt

David Quandt
Rising above the lush landscapes of Kapalua, this stunning single-level home in Pineapple Hill offers breathtaking ocean, sunset, and neighbor island views. Fully remodeled in 2020, the residence showcases elegant bamboo flooring, sleek tile bathrooms, and a modern kitchen with a new island, refaced cabinets, and premium Thermador appliances. Dual wine refrigerators and a KitchenAid refrigerator add a touch of luxury. Expansive 8-foot sliding glass doors in the living, dining, and primary suite seamlessly frame vistas of Lanai and Molokai, blending indoor and outdoor living. The primary suite indulges with two walk-in closets and a spa-inspired bath featuring a new standing tub. Outside, a resurfaced pool and freshly painted exterior (2024) enhance the appeal, while an owned photovoltaic system ensures efficiency. Tucked in a private cul-de-sac within gated Pineapple Hill, it’s just moments from hiking trails, fine dining, and world-class golf courses.
- Price:
- $3,995,000
- Size:
- 2,794 sq ft
- Contact:
- David Quandt, Coldwell Banker Island Prop-KP, 808.457.0604
Tropical Sanctuary In Upper Pupukea | $2,450,000


Listing agents: John R. Vasta & Erica Lehmkuhl

Listing agents: John R. Vasta & Erica Lehmkuhl
Set against the tranquil shores of upper Pupukea, this waterfront estate offers a private tropical haven on over an acre of lush land. Surrounded by banana and puakenikeni trees, the property evokes a personal Eden, complete with a palm-lined driveway that ensures serenity. The main residence upstairs features three bedrooms and two bathrooms, with vaulted ceilings, a working fireplace, and expansive lanais that frame breathtaking ocean views. Each bedroom opens to its own lanai, inviting cool breezes and scenic vistas. A separate one-bedroom, one-bathroom unit downstairs, with a wet bar, fireplace, and private entrance, suits multigenerational living or guests. Outside, a deep tile swimming pool and hot tub overlook vibrant foliage, while a spacious yard beckons gatherings. A three-car garage and ample parking accommodate boats, jet skis, and more, embracing a life of adventure and relaxation.
- Price:
- $2,450,000
- Size:
- 2,532 sq ft
- Contact:
- John R. Vasta & Erica Lehmkuhl, Seaside Realty LLC, 808.940.2790 , 808.723.0953














