Hawai‘i’s real estate market is a captivating mosaic of luxury and nature, where tropical elegance meets architectural splendor. From the verdant slopes of Maui to the sun-kissed coasts of O‘ahu, the islands host estates that offer unmatched seclusion, panoramic ocean views, and designs that harmonize with their lush surroundings.
Let’s dive into some of the most expensive homes in Hawaii, where each property is a private paradise in its own right.
5. Kihei, Maui, HI – $27,500,000
Set along the sands of Keawakapu Beach, this $27,500,000 estate offers 5,435 square feet of interior space with 4 bedrooms and 6 bathrooms, built in 1988. The gated property includes a resort-style pool with a waterfall and grotto, a separate guest Ohana, and an oversized garage, all on a beachfront parcel designed for privacy. It combines expansive ocean views with close proximity to Wailea and Makena amenities, offering both seclusion and convenience.
Where is Kihei?
Kihei is a coastal town on the southwest shore of Maui, Hawaii. It is known for its beaches, snorkeling spots, and views of nearby islands. The town lies in the rain shadow of Haleakalā, giving it a dry and sunny climate. Kihei is part of Maui County and stretches along six miles of shoreline.
Living Room
Opened wide to the lanai, the living room includes a sectional sofa, wood-framed armchairs, and natural decor accents under a pitched ceiling with exposed beams. Artwork and tropical plants decorate the walls and corners, while tile flooring connects seamlessly to the outdoor space. A dining table sits just outside beneath the covered patio.
Kitchen and Dining
Connected as one space, the kitchen and dining area combine rich wood cabinetry, a dark island with seating, and a formal dining table on a patterned rug. Pendant lights hang above both counters, while framed artwork adds color to the surrounding walls. A passthrough window opens the kitchen to exterior views and ventilation.
Bedroom
Framed by corner windows and a vaulted wood ceiling, the bedroom offers ocean views directly from a carved four-poster bed. A pair of green armchairs and a side table create a sitting area by the windows, while a TV and dresser anchor the far wall. Small vertical windows line the angled corner near a work desk tucked in the back.
Bathroom
Extended by sliding doors that open to a private balcony, the bathroom includes a freestanding tub, dual vanities, and a walk-in shower with separate entrances. A wood-paneled ceiling and marble finishes define the interior, while small windows add more natural light. Built-in shelves and towel holders are neatly arranged along the walls.
Pool Grotto
Tucked inside a cave-like structure, the pool grotto features a hidden swim-through entry that leads out to the main pool area. Waterfalls cascade at the edge of the rock formation, with lounge chairs visible just outside. Stone decking surrounds the turquoise water, blending natural textures with the tropical landscape.
Listing agents: Ryan Maclaughlin Rb-21325, Alex Cortez Rb-21828 of Island Sotheby’S Int’L Rlty(W), info provided by Coldwell Banker Realty
4. Kamuela, Big Island, HI – $28,000,000
Commanding over 2 acres along Puako Bay, this $28,000,000 estate spans 5,360 square feet with 6 bedrooms and 8 bathrooms, completed in 2019. The property includes a tennis court, sand volleyball court, heated swimming pool, and four outdoor showers, blending recreation with comfort. Sustainable features such as a solar panel system with battery storage and high-end appliances add modern efficiency to its oceanfront setting.
Where is Kamuela?
Kamuela, also known as Waimea, is a town in the South Kohala District on the Big Island of Hawaii. It is surrounded by ranch lands and is home to Parker Ranch, one of the largest cattle ranches in the U.S. The town has a cooler climate due to its elevation. Kamuela is the postal name used to avoid confusion with other Hawaiian towns named Waimea.
Living Room
Framed by a wood-slat divider and a vaulted ceiling, the living room includes a sectional sofa, patterned rug, and pendant lighting above. A game area with a pool table is visible in the back, next to floor-to-ceiling windows that let in natural light. The staircase curves along the right wall, connecting the two-level space with open sightlines.
Kitchen
Arranged around two large islands, the kitchen combines white cabinetry, a marble countertop, and wood-accented ceiling. Seating for five lines the island in front, while built-in appliances and chevron-patterned tile complete the back wall. Pendant lights hang above the workspace, providing soft illumination over the counters.
Outdoor Dining Area
Positioned under a wood-paneled ceiling, the outdoor dining area features a large table with enough seating for twelve. Ceiling fans and lantern-style lighting fixtures are mounted above, while views of the pool and ocean stretch just beyond the open wall. Retractable doors allow a full connection to the patio from the indoor space.
Bedroom
Backed by a light blue textured wall, the bedroom includes a platform bed, wood ceiling, and simple woven chair in the corner. Hanging pendant lights act as bedside fixtures, while small floating nightstands are built directly into the headboard wall. A mirror and open doorway reflect the green exterior visible through nearby windows.
Bathroom
Opened up to an oceanfront balcony, the bathroom includes double vanities, a soaking tub, and an outdoor shower with a stone accent wall. Fixtures are mounted over clean-lined wood cabinetry, while mirrors hang from the ceiling for unobstructed views. Tiled flooring connects the interior and exterior sections seamlessly.
Listing agent: Tomoko Matsumoto of Hapuna Realty, info provided by Coldwell Banker Realty
3. Kailua-Kona, Big Island, HI – $29,500,000
Situated on the Kohala Coast, this $29,500,000 estate spans 5,334 square feet and includes 3 bedrooms and 5 bathrooms, built in 2005. The home is arranged in a pod-style layout with multiple detached guest hales and features ocean views, an infinity pool, and high-end finishes throughout. Designed by Shay Zak, the property blends indoor and outdoor living with private lanais, outdoor shower gardens, and access to Kapaka Bay amenities.
Where is Kailua-Kona?
Kailua-Kona is a town on the west coast of Hawaii’s Big Island. It was once a retreat for Hawaiian royalty and is now a center for deep-sea fishing, coffee farming, and tourism. The town hosts the annual Ironman World Championship triathlon. Kailua-Kona lies in the North Kona District and faces the Pacific Ocean.
Living Room
Anchored by curved sofas and colorful accent chairs, the living room sits beneath a vaulted wood ceiling with polished dark flooring below. Art pieces and sculptural lighting line the space, while large openings connect it directly to the pool and lanai. A dining table is positioned toward the back, merging the lounge with the kitchen zone.
Kitchen and Dining
Defined by a marble island with wood stools, the kitchen includes flat-panel wood cabinets, integrated appliances, and matching marble backsplash. Dining takes place on an extended table nearby, surrounded by leather chairs under a modern light fixture. The kitchen ceiling mirrors the living room’s wood panels, maintaining visual continuity.
Bedroom
Positioned between the pool and living room, the bedroom includes a wood-framed bed, vaulted ceiling with recessed lighting, and sliding doors on both sides. A hallway to the bathroom and a writing desk complete the setup, with framed artwork displayed along clean white walls. Views of the pool and lounge chairs are visible just beyond the doorway.
Bathroom
Organized with floating wood vanities, a glass walk-in shower, and a freestanding tub, the bathroom stretches across a long open layout. One side features patterned tile and pendant lights, while the other uses a sculptural screen for visual separation. Windows and open doorways bring in natural light from the outdoor areas beyond.
Poolside Lanai
Stretching along the edge of an infinity pool, the poolside lanai features shaded seating areas under a peaked wood roof supported by timber columns. Lounge chairs are placed in shallow water while the covered areas offer cushioned seating just steps from the pool. Interior living and dining spaces connect seamlessly through wide open walls.
Listing agent: Nicole Vincent of Aloha Sotheby’S International Realty Inc., info provided by Coldwell Banker Realty
2. Makawao, Maui, HI – $38,000,000
Located in Makawao, this $38,000,000 estate covers 258 acres and includes a main 3,285 square feet home with 4 bedrooms and 3 bathrooms, built in 2020. The property features two LEED Gold certified homes and spans across 9 subdividable lots, with plans for up to 42 residences pending approval. It operates independently with its own water supply and a 1-megawatt solar microgrid, combining sustainability with large-scale development potential.
Where is Makawao?
Makawao is a town on the island of Maui in Hawaii, located on the slopes of Haleakalā. It is known for its paniolo (Hawaiian cowboy) culture and hosts the annual Makawao Rodeo. The town blends ranching traditions with a small arts community. Makawao is part of Maui County and lies inland from the coastal town of Paia.
Living Room
Oriented around a fireplace set into a black-framed wall, the living room connects to two separate patios through sliding glass doors. A curved sofa faces the fire, while dining and reading nooks fill out the space. Windows above and on each side of the room frame sunset and ocean views.
Kitchen
Centered around a large island with seating for four, the kitchen includes light wood cabinetry, open shelving, and built-in stainless appliances. Positioned beneath three pendant lights, the island faces a window that frames views of the surrounding field. Floating shelves on either side of the window display minimal ceramics and decor.
Home Office
Set up with a dark-toned desk and natural light streaming through side windows, the home office includes built-in storage with woven fronts. A walk-in closet is partially visible behind a wooden sliding door, hinting at extra space. A ceiling fan and simple furnishings create a clean, functional workspace.
Bedroom
Positioned to maximize the view, the bedroom features sliding glass doors that open to a patio facing open land and distant mountains. Multiple windows stretch across the double-height walls, bringing in light from all sides. A platform bed, reading chair, and potted plant anchor the space in neutral tones.
Bathroom
Designed with a double vanity and wooden drawers, the bathroom includes a glass-walled shower and a built-in bathtub under a set of windows. Soft light filters through upper transom windows, brightening the white tile and wood-textured finishes. Wall-mounted mirrors and slim vertical lights complete the setup.
Listing agents: Robert F. Vafaie Rb-19490, Brook Y Starr Rb-19915 of Compass-W, Mango Tree Realty LLC., info provided by Coldwell Banker Realty
1. Honolulu, O’ahu, HI – $45,000,000
In Kahala, this $45,000,000 estate stretches across 1.3 acres with 9,896 square feet of interior space, offering 6 bedrooms and 8 bathrooms. Built in 1988, the home is laid out on a single level with expansive ocean frontage and separate living areas for each guest suite. Designed for seamless indoor-outdoor living, it includes features like a 5,000 square feet lanai and a beachside pool and spa.
Where is Honolulu?
Honolulu is the capital of Hawaii, located on the island of Oʻahu in the central Pacific. It is a major hub for international business, military defense, and tourism. The city is home to Pearl Harbor, Waikiki Beach, and the University of Hawaiʻi. Honolulu also serves as the main gateway to the Hawaiian Islands.
Covered Lanai Lounge
Surrounding the covered lanai, the open-air living area overlooks the pool and ocean just beyond the edge of the terrace. Lounge groupings are arranged around low wood tables, with planters and potted palms lining the outer walls. Seating options include cushioned sofas, woven armchairs, and daybeds spaced throughout the expansive area.
Main Living Room
Framing a panoramic ocean view, the main living room opens fully to the outdoor dining terrace through large retractable glass walls. Furniture in this interior space includes sectional sofas, accent chairs, and a circular coffee table placed over a woven rug. A sculptural ceiling light hangs above, while built-in shelving displays glassware and decor along the back wall.
Family Room and Kitchen
Stretching from the indoor lounge to the chef’s kitchen, the family room creates a seamless transition between gathering and dining areas. A long island with barstools anchors the kitchen, facing a sunken living area filled with armchairs and a coffee table arrangement. Floor-to-ceiling shelving and potted plants add depth and greenery to the neutral-toned design.
Outdoor Kitchen
Tucked beneath a wood-paneled ceiling, the outdoor kitchen features a built-in stainless grill, bar sink, and a curved stone island lined with woven stools. Located along the back wall, the cabinetry provides storage and display space, flanked by tropical plants on each side. Dining and lounge seating fill out the open-air layout under natural light and greenery.
Pool Deck and Backyard
Sitting just off the lanai, the backyard pool area features a rectangular pool with a raised hot tub set into a wide wooden deck. Lounge chairs are placed at both ends of the pool, offering views of the ocean beyond the manicured lawn. Flanked by palm trees and tall hedges, the space maintains privacy without obstructing the coastal backdrop.
Listing agent: Tracy Allen of Coldwell Banker Realty
