Hawaii’s real estate market is a vivid blend of luxury and natural beauty, where oceanfront estates coexist with volcanic landscapes and lush greenery. Properties across the islands feature sprawling layouts, resort-level amenities, and rare access to some of the worldโs most celebrated beaches.
Letโs dive into some of the most expensive homes in Hawaii, where island living meets ultimate opulence.
5. Kailua, Oahu, HI โ $25,000,000
Stretching across more than 60,000 square feet of prime oceanfront land in Kailua, this expansive estate offers 13,289 square feet of interior space with 10 bedrooms and 11 bathrooms between two separate residences. Built in 2001, it features 255 feet of beach frontage, a lagoon-style pool, jacuzzi, sauna, tennis and pickleball court, theater room, and massage treatment area. Listed for $25,000,000, the property is one of Oahuโs largest private beachfront holdings.
Where is Kailua?
Kailua is a town on the windward coast of Oสปahu, Hawaii, about 12 miles northeast of Honolulu. It is known for its long beaches, including Kailua Beach and Lanikai Beach. The town has a mix of residential neighborhoods, small businesses, and outdoor recreation spots. Kailua also served as a vacation destination for U.S. presidents during their stays in Hawaii.
Living Room
Vaulted wood ceilings and stone floors frame the large living room, anchored by two curved staircases and multiple seating areas. A mix of white couches surrounds a carved coffee table atop a patterned rug in the center. To the side, a small bar and dining nook connect the room to the rest of the open-plan layout.
Kitchen
Dark granite countertops and wood cabinetry define the spacious kitchen, centered around a multi-level island with bar seating. A built-in booth wraps around a corner by the large window, forming a separate dining space with a view of tropical foliage. Recessed lighting and coffered ceilings with wood insets complete the warm tone throughout.
Bedroom
Ocean views flood the bedroom through a massive picture window built into the far wall. A king-sized bed faces the glass, with two chairs and a side table positioned in the window alcove. Hardwood floors and a ceiling fan round out the roomโs coastal setup.
Bathroom
Soaking in the corner tub of the primary bathroom comes with an uninterrupted ocean view framed by a bank of wood-trimmed windows. The tub is surrounded by curved tile steps that match the floor and built-in vanity. Large mirrors and indoor plants enhance the natural light throughout the space.
Pool Area
Natural stone paths wind through the backyard, leading to a lagoon-style pool with waterfalls and lush greenery. Wicker loungers with striped cushions are arranged on a grassy patch facing the water. Covered patios and tropical landscaping surround the pool area, creating a private outdoor retreat.
Listing agent: Brandon E Kim of List Sotheby’S Int’L Realty, info provided by Coldwell Banker Realty
4. Lahaina, Maui, HI โ $26,900,000
Located in Kapalua and built in 2015, this single-level estate spans 11,072 square feet with 8 bedrooms and 8 bathrooms, including a 2-bedroom ohana for added privacy. Set on 4.49 acres, the property includes a pool, spa, theater room, gym, office, outdoor entertainment area, and private golf features. Priced at $26,900,000, it sits within the Plantation Estates gated community, adjacent to the Kapalua Plantation Golf Course.
Where is Lahaina?
Lahaina is a historic town located on the west coast of Maui, Hawaii. Once the capital of the Hawaiian Kingdom, it later became a center for the whaling industry in the 1800s. The town is known for its Front Street, which features shops, restaurants, and cultural landmarks. Lahaina was severely damaged by wildfires in August 2023, leading to significant loss and recovery efforts.
Living Room
Wood-paneled ceilings stretch above the open-concept living room that looks out onto an expansive deck and infinity pool. Low-slung seating surrounds multiple tables in the center, positioned for lounging and conversation. Just beyond, the outdoor area blends seamlessly with the interior through massive retractable walls.
Kitchen
Dark stone counters and cream-colored cabinetry define the central kitchen, anchored by a wide island with seating for four. Above the cooktop, a large custom range hood sits between vertical storage cabinets. Double ovens and built-in appliances complete the functional wall along the right side.
Bedroom
Wide glass doors retract to expose a primary bedroom directly connected to a private lawn with ocean views. A platform bed sits beside floating nightstands, with a mounted TV suspended from the ceiling. Across the room, a dresser and mirrors are positioned along the wall opposite the bed.
Bathroom
Twin vanities line the back wall of the primary bathroom, which includes a chandelier-lit space and floor-to-ceiling cabinetry. In the center, a large glass-enclosed shower sits across from a stone-rimmed soaking tub beneath a window. Robes hang near the tub, flanked by glass jars and towels on the ledge.
Pool Area
Curved rock formations shape a multi-level outdoor pool area built into the backyard. Water cascades from one pool into the next, wrapping around lush landscaping and ending in a deeper basin below. A long slide curves through the center, connecting the upper deck to the water below.
Listing agent: Raymond Chin of Coldwell Banker Island Properties, info provided by Coldwell Banker Realty
3. Princeville, Kauai, HI โ $30,000,000
Ahonui Gardens on Kauaโiโs North Shore includes 8 bedrooms and 11 bathrooms across 7,269 square feet, built in 2002. Listed for $30,000,000, the estate spans 50 acres over two lots, with approvals for up to 10 luxury homesites. The property features three residences, a yoga studio, stables, a photovoltaic system, and expansive gardens with mountain and distant ocean views.
Princeville
Princeville is a resort community on the north shore of Kauaสปi, Hawaii, in the Hanalei District. It was once a large sugar plantation and is named after Prince Albert, son of King Kamehameha IV. The area features golf courses, cliffside views, and proximity to Hanalei Bay. Princeville also serves as a gateway to the scenic Nฤ Pali Coast.
Lounge
Rounded arch windows bring mountain views into the sitting room, where wicker furniture and a carved wood table anchor the space. Painted wall details and a wood-plank ceiling with beams add texture above. Built-in benches and natural light make the room feel open and calm.
Dining Area
Long beams run overhead in the combined dining and living area, which connects through wide doors to the outdoors. A formal table with seating for ten is placed in front of arched windows and doors. Farther back, multiple sitting zones surround a grand piano and soft seating.
Bedroom
Wood beams extend into the ceiling of the bedroom, where a king-sized bed is centered against a white wall with matching nightstands. A stairway curves upward in the corner near a tall arched window. French doors open directly to the garden outside.
Pool Area
Brick pavers border the rectangular pool, tucked between lush plants and tall palms. A stucco wall encloses the space, and a tiled outdoor shower sits just off to the side. The two-story home rises behind the pool, featuring balconies and shaded patios.
Aerial View
Red-tiled roofs stand out in the aerial view of the estate, which stretches across a vast green landscape with groves, palms, and mountain views. Multiple structures, including the main house, guesthouse, and pool, are spaced out on the manicured property. A long driveway lined with trees leads to the entrance.
Listing agent: Matthew Beall of Hawaii Life, info provided by Coldwell Banker Realty
2. Kihei, Maui, HI โ $31,000,000
This 7,244 square feet oceanfront estate in Maui features 5 bedrooms, 5 bathrooms, and 2 half baths, built in 2018. Listed for $31,000,000, the property spans over half an acre with direct access to Keawakapu Beach and includes a private gated beach entrance, oceanfront lawn, pool courtyard, and landscaped gardens. Three master suites offer ocean views, while guest suites face the pool, blending privacy with coastal living.
Where is Kihei?
Kihei is a town on the western side of Maui, Hawaii, along the islandโs sunny southwestern coast. It is known for its beaches, snorkeling spots, and views of the nearby islands. Kihei was once part of Hawaiian royal land and later became an area for sugarcane production. Today, it has a mix of residential neighborhoods, resorts, and natural reserves like Keฤlia Pond.
Living Room
Oriented toward the ocean, the living room includes two white sofas arranged around a rustic wood coffee table on a jute rug. An open wall frames views of palm trees and blue water just past the lawn. Wood accent furniture and ceiling fans with leaf-shaped blades emphasize the coastal setting.
Kitchen
Behind the island seating, the kitchen features natural wood cabinetry, white countertops, and stainless steel appliances along one side. A marble-topped island with seating sits at the center, while pendant lights and a large window bring in ocean views. The space connects to a dining table positioned by the window.
Bedroom
On the ocean-facing side of the home, the bedroom includes a white bed frame with layered linens and natural-toned decor. A woven rug spans the wood floor, with round ottomans at the foot of the bed and a sofa in the corner. Sliding doors open directly onto the lawn with two outdoor chairs.
Bathroom
Along one side, the bathroom uses green tile in the shower and countertop to contrast against the neutral walls and floor. A freestanding tub sits near two windows, and a wide mirror reflects the dual-sink vanity. Woven drawer fronts and wood trim echo the natural palette found throughout the house.
Pool Area
Centered in the courtyard, the outdoor pool is surrounded by tall greenery and paved decking with lounge chairs and umbrella-covered tables. Doors from multiple rooms open onto this space, creating a private enclosure. Tropical plants and palm trees wrap around the perimeter.
Listing agents: David W Richardson Rb-10780, Josh Jerman Rb-19728 of Hawaii Life (W), info provided by Coldwell Banker Realty
1. Honolulu, Oahu, HI โ $55,000,000
Hoโoluana Estate in Honolulu offers 11 bedrooms and 11 bathrooms across 10,047 square feet and was built in 1967. Priced at $55,000,000, the property spans over two acresโnearly 89,120 square feetโand includes two residences and an open lot with beachfront access and ocean views. Located between Kahala and Waikiki, it sits on two adjacent parcels zoned R-7.5, offering both development potential and privacy.
Where is Honolulu?
Honolulu is the capital city of Hawaii, located on the southeastern coast of the island of Oสปahu. It serves as the state’s political, economic, and transportation center. The city includes the famous Waikฤซkฤซ Beach and is near Pearl Harbor, a key historical site. Honolulu also hosts the University of Hawaiสปi and a major international airport.
Living Room
Positioned just off the beachfront lawn, the living room uses sliding glass doors to frame the view of the ocean beyond. A white sectional sofa and cushioned chairs form a cozy seating area around a dark wood coffee table set on a sea-inspired rug. Tropical plants and neutral-toned curtains add a relaxed, breezy feel.
Kitchen
Set in a long open layout, the kitchen runs parallel to large windows and includes dual islands with seating, one featuring a wine cooler and the other a black stone counter. Light wood cabinetry and louvered windows line the wall, while pendant lights hang above the prep space. Views of the ocean extend all the way through to the dining area.
Dining Room
At the far end of the open space, the dining room includes a wooden table set for eight over a bright aqua-patterned rug that mirrors the ocean view outside. Glass doors and windows wrap around the room, opening to the beachside patio and seating area beyond. Indoor plants and a corner sectional blend with the tropical setting.
Courtyard
In the heart of the property, the courtyard is arranged with a central fountain surrounded by natural stone tile and archways leading to individual rooms. Stucco walls curve upward, creating a series of white domes under the setting sun. Tropical landscaping and torch-style wall sconces complete the open-air design.
Pool Area
Looking out over the coast, the outdoor pool area features a rectangular pool bordered by a wide deck with cushioned loungers and umbrellas. Palm trees frame the view, while a low white wall and gate provide privacy from neighboring homes. The ocean stretches in the background with surf rolling toward the shore.
Listing agent: Noel Pietsch Shaw of Hawaii Life, info provided by Coldwell Banker Realty
