14 Most Expensive Houses in Hawaii (Current Prices)

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Hawaii is known as “paradise” for a reason: it is a beautiful place to live. But this does not come without a price tag. The state of Hawaii has many natural resources, but it also has some of the highest costs of living among all states in America. The reason why there are so many expensive houses in Hawaii is that it is a beautiful place to live. There are natural wonders all around, such as the beach and the ocean.

The weather is very nice in Hawaii, and there are many different activities to do outside of work or school. The people who live in Hawaii also have high standards for their homes because it’s important for them to live in a place where they feel comfortable and safe. Perhaps you are planning to move to the islands and want to know some information about houses here. That is why this list of expensive houses in Hawaii will surely guide you.

14. 4557 Makena Rd, Kihei, HI 96753

Price: $22,500,000
Year Built: 2007
Lot Area: 3.14 Acres
No. of Bedrooms: 5
Type: Single Family Residence

4557 Makena Rd, Kihei, HI 96753photo source: realtor.com

Opens a unique opportunity is the traditional Keahou at Makena estate property. Only 7 parcels totaling 3 acres each make up Keahou. The Boutiques at Wailea, which offers five-star dining and luxury shops, and three championship golf courses are all within walking distance of this guarded ocean sunset view villa.

With coffered ceilings, a recently finished home theater extension, and a wide estate that maximizes vistas on a single level, a lavish yet comfortable existence is made possible. Owners can sit by the resort-style pool or take a short stroll to Palauea Bay’s white sand beach across the street.

Did You Know?

The pool and spa are magnificent spaces where one may unwind while taking in the picture-perfect ocean vistas beyond.


13. 4679B Kahala Ave, Honolulu, HI

Price: $23,000,000
Year Built: 1998
Lot Area: 1.75 Acres
No. of Bedrooms: 6
Type: Single Family, Detach Single Family, Multiple Dwellings

4679B Kahala Ave, Honolulu, HIphoto source: realtor.com

Vladimir Ossipoff, a well-known Hawaii architect, created the single-story Hawaiian Modern home at 4679B house on Kahala Avenue in Honolulu. You are welcomed into this tropical refuge by a curving driveway tucked away in lush greenery. Natural lighting and ventilation are well used, and indoor-to-outdoor transitions are seamless thanks to organic architecture that works with nature.

Step outside to the beachfront backyard or pool from the lounge room, which showcases the expansive ocean vista and opens to lanais on all sides. 1bd Cottage and 5bd/5ba Main House. 2016 saw about $1 million spent on maintenance, a new roof, paintwork, air conditioning, and electrical work.

Did You Know?

The biggest beachfront property available for sale in Hawaii is this one.


12. 20 Kai Ala Dr, Lahaina, HI

Price: $24,500,000
Year Built: 2000
Lot Area: 0.98 Acres
No. of Bedrooms: 8
Type: Single Family Residence

20 Kai Ala Dr, Lahaina, HIphoto source: realtor.com

20 Kai Ala Dr, Lahaina is one of only six beachfront properties available in Kaanapali, making it a unique offer. This elegant property, which has over 11,000 square feet of living space, has eight suite-style bedrooms, a cinema room, formal and casual dining areas, a leisure room, a gym, and an exterior kitchenette.

The property now has a light, airy vibe thanks to the homeowners’ recent updates to the bathrooms and the kitchen. Exquisite two-story pocketing glass doors that open to the beautifully planted lawns are located in the living room on both the mauka and makai sides.

Did You Know?

Majestic coastal gardens that offer privacy but also enable access to one of Maui’s most well-known beaches complement the pool and pavilion.


11. 5156 Weke Road Hanalei, Kauai

Price: $29,750,000
Year Built: 2013
Lot Area: 1.11 Acres
No. of Bedrooms: 5
Type: Single Family Residence

5156 Weke Road Hanalei, Kauai photo source: realtor.com

This expansive oceanfront residence has unmatched perspectives of the crescent arch of the Bay, breaking surf, splendid waterfall-clad mountains, and the setting sun. It is located in one of the most sought-after areas on Hanalei Bay on a large 1.1-acre lot. The house character of the property is palpable in every way. It is secure, private, and has a gated entrance.

With expansive views of the ocean from every angle, the large room seamlessly connects the inside and the outside. Surfers of all ages and abilities can enjoy the sea life because it is close to the beach and has a safe sandbar near the coast.

Did You Know?

A spacious selected lanai with a hardwood dining table as its focal point is the perfect setting for small dinner parties with views of the beach and the sea beyond.


10. 4508 Makena Road Kihei, Maui

Price: $29,980,000
Year Built: 2018
Lot Area: 0.44 Acres
No. of Bedrooms: 4
Type: Single Family Residential

4508 Makena Road Kihei, Maui photo source: realtor.com

One of the most unique properties ever offered for sale is located at 4508 Makena Road. In addition to providing a peaceful retreat on one of Hawaii’s most unspoiled beaches, the newly built, nicely decorated property is just a short stroll from some of the island of Maui’s most opulent villas.

The indoor living space smoothly transitions to the large covered lanais so that you can enjoy the Hawaiian way of life to the fullest. The house was constructed with the best expertise possible utilizing premium materials that were hand-selected from all around the world.

The magical location is filled with the spirit of aloha because it was once the hub of an old Hawaiian town and a beach where the threatened species Honu’ea lay their eggs (Hawksbill Turtle).

Did You Know?

With its 20-foot cathedral ceilings, white limestone floors and museum grout, raw piled coral on sections of the walls, and open living area, the beautifully designed Great Room exudes warmth and hospitality.


9. 145 Kailuana Loop Kailua, Oahu

Price: $30,000,000
Year Built: 2001
Lot Area: 1.37 Acres
No. of Bedrooms: 9
Type: Single Family, 2 Bedroom Cottage, Detach Single Family

145 Kailuana Loop Kailua, Oahuphoto source: tracyallenhawaii.com

Exceptional Kailua Beachfront Estate consists of 2 properties with a combined area of around 60,000 square feet and 255 linear feet of beach frontage. Two magnificent homes by renowned architect James McPeak include staff quarters, sizable tropical grounds, a resort-style pool and spa with waterfalls, a sauna, a gym, a tennis court, and more.

This island compound is genuinely unmatched with more than 15,000 lush living spaces.

This almost 1.5-acre parcel of land, which formerly belonged to the Rothschild family, has 250 feet of white sand beach. There are two major houses that together have more than 17,000 square feet of living area, 10 bedrooms, and 11 bathrooms. There includes a lagoon pool, a golf course, a steam room, entertainment spaces, and other high-end resort facilities.

Did You Know?

The house, which was constructed in 2001, is known by the Hawaiian name Kai Moena, which means “House of the Resting Sea.”


8. 4505 Kahala Avenue Honolulu, Oahu

Price: $30,000,000
Year Built: 1988
Lot Area: 1.30 Acres
No. of Bedrooms: 5
Type: Single Family Residence

4505 Kahala Avenue Honolulu, Oahuphoto source: oahure.com

With 5 bedrooms and 8 baths, 4505 Kahala Ave is a 9,896 square-foot home on a 1.3-acre lot. Currently, off the market, this house last sold for $29,000,000. That was on February 7, 2006. Redfin statistics for Honolulu lead to a $19,625,621 valuation for the property.

Did You Know?

On February 8, 2006, this single-family residence was last sold for $29,000,000.


7. 4200 Anini Vista Drive #D Kilauea, Kauai

Price: $31,000,000
Year Built: 2003
Lot Area: 6.87 Acres
No. of Bedrooms: 6
Type: Single Family Residence

4200 Anini Vista Drive #D Kilauea, Kauaiphoto source: redfin.com

The point at Anini Vista is a nearly 7-acre refuge with a massive compound of living spaces that is perched on a bluff above Kauai’s North Shore. In addition to the cellar, video theater, workplace, pools, and spa, there are two guest bungalows. The house is not only close to dining, shopping, and many types of entertainment, but it also has stunning views and everyday sunsets over Hanalei.

The house includes five bedrooms, three bathrooms, a decorative fireplace, and hardwood floor covering. In addition to the stunning ocean view, the bay, coastline, mountain, ocean horizon, sunset, sunrise, and waterfalls can all be seen from the house.

Did You Know?

This single-family home was last sold for $31,500,000 on March 1, 2022.


6. 4423 Kahala Avenue Honolulu, Oahu

Price: $34,000,000
Year Built: 2008
Lot Area: 0.36 Acres
No. of Bedrooms: 4
Type: Single Family, Detach Single Family

4423 Kahala Avenue Honolulu, Oahuphoto source: coldwellbankerhomes.com

This stunning home, Kahala Avenue Honolulu, Oahu which was featured in the Hawaii-Five-O series, showcases the contemporary elegance of alluring Kahala and was expertly created to display the exquisite craftsmanship of Pyramid Premier Properties, an award-winning designer and developer from Honolulu. Living and dining rooms are smoothly connected by high ceilings and an open floor design.

The seamless transition between indoor and outside spaces is made possible by glass walls that blend into the nooks and crannies of the walls. A warmed infinity pool with a 40-foot tiled wall and water flowing into a lap pool is located on the second floor of a guest house. Multiple meeting areas are among the lavishly decorated rooms in both the main building and the guest home. a sizable, airy kitchen.

Did You Know?

This wonderful small tropical retreat is move-in ready and is close to Diamond Head and Waikiki’s well-known beaches.


5. 72-393 Kaupulehu Dr Kailua-Kona, HI 96740

Price: $35,000,000
Year Built: 2008
Lot Area: 1.90 Acres
No. of Bedrooms: 7
Type: Single Family Residence

72-393 Kaupulehu Dr Kailua-Kona, HI 96740 photo source: mansionglobal.com

With sweeping views of the entire villa, the surrounding landscape, and the beach, the largest custom estate, Kaupulehu Dr. Kailua-Kona is situated at the peak of Hualalai Resort. It provides unimpeded vistas and seasonal sunsets without rooftops in the way.

Eight full bathrooms, two half baths, two full kitchens, a theater, and a fitness center with a massage room, locker room, sauna, and steam room are all features of this home. There are also seven bedrooms.

 Did You Know?

Providing views of three holes of the Jack Nicklaus Championship Golf Course at the Resort and two holes of the member-only Tom Weiskopf Ke’olu Championship Golf Course that extend all the way to the Pacific Ocean.


4. 1118 Ala Moana Boulevard #3600 Honolulu, Oahu

Price: $36,000,000
Year Built: 2016
Lot Area: 0.1029 Acre
No. of Bedrooms: 4
Type: Condo

1118 Ala Moana Boulevard #3600 Honolulu, Oahuphoto source: robertperryhawaii.com

In terms of luxurious living in Honolulu, The Villas at Waiea are at the top. A three-tiered, exceptional experience is offered by Villa 9. This four-bedroom, 4.5-bath home features a modern, open floor plan with a double-height atrium, elegant finishes, and sizable, multi-level lanais.

There are two roomy storage facilities, a breathtaking sky lanai with views of the ocean and port, and a private pathway that can be accessed straight from the parking spaces. Additionally, the owner will have complete access to Waiea’s exceptional resort-style amenities, which include a concierge and an infinity edge lap pool.

Did You Know?

In addition to 5 guest suites, an infinity edge pool, a gym, a sauna, Barbeque pavilions, a screening room, a sunset lounge, a dining area, and many other amenities, the building offers world-class concierge service.


3. 2818 Kamookoa Rd Lot 1, Kilauea, HI

Price: $40,500,000
Year Built: 2001
Lot Area: 237.79 Acres
No. of Bedrooms: 6
Type: Single Family Residence

2818 Kamookoa Rd Lot 1, Kilauea, HI photo source: zillow.com

On Kauai’s North Shore, Wai Kala Ranch offers a sizable amount of land. In total, the three contiguous properties that make up this offering have more than 237 acres of stunning terrain and moving water.

With breathtaking views of the mountains from all across the area, Wai Kala Ranch is situated at the base of Mount Namahana. The property is divided into various waterways, cascades, swimming holes, two freshly renovated homes, several equestrian-related buildings, and countless further career advancements.

Both the 3,509 square foot, four bedroom, three and a half bathtub home on this 137.69-acre property as well as the 1,080 square foot, two bedroom, one bathroom home received substantial renovations in 2019 and were both finished.

Did You Know?

International golfing and water activities may be discovered in the surrounding villages of Princeville and Hanalei, while the eating and shopping options of charming Kilauea resort are just minutes away to the east from Wai Kala Ranch.


2. 9 Bay Drive Lahaina, Maui

Price: $41, 900,000
Year Built: 1996
Lot Area: 9.96 Acres
No. of Bedrooms: 7
Type: Single Family Residence

9 Bay Drive Lahaina, Mauiphoto source: realtor.com

Luxury residences and amazing views may be found at Hawea Point. On Hawea Point, amid the renowned Kapalua Resort, is the estate’s 9.9 acres bearing its name. A reserve area covering more than two acres on the property guarantees that the breathtaking ocean and outlying island vistas will never be disturbed.

The 9 Bay Drive Lahaina, Maui house, which occupies the entire plot of land, was meticulously designed down to the last detail to provide unmatched luxury while keeping a low profile to blend in with the surrounding scenery. Hawea Point includes a large living area and guest wing complex surrounding a central courtyard and peristyle with a fountain in the middle.

Did You Know?

The “guest yard” of the house has an orchard with banana, orange, and avocado trees.


1. 72-2747 Uluweuweu Akau Pl, Kailua Kona, HI

Price: $45,000,000
Year Built: 2015
Lot Area: 1.37 Acres
No. of Bedrooms: 6
Type: Single Family Residence

72-2747 Uluweuweu Akau Pl, Kailua Kona, HIphoto source: zillow.com

The 72-2747 Uluweuweu Akau Pl, Kailua Kona house is considered the most expensive house in Hawaii which costs $45,000,000.

This almost 1.5-acre Big Island seaside paradise lot offers the chance to join the Kukio Golf and Beach Club. There is more than enough room to sprawl out throughout the vast, grassy lawns that lead to a dazzling beach thanks to the home’s six bedrooms, over seven bathrooms, and nearly 9,000 square feet of space.The 72-2747 Uluweuweu Akau Pl, Kailua Kona house was sold in December 2020.

Property owners are welcome to join the Kukio Golf & Beach Club, a private club with first-rate amenities located on the seaside. This club has two clubhouses with private dining, a sports complex, an ocean pursuits center, an expansive indoor and outdoor spa, and an 18-hole Championship Golf Course built by Tom Fazio in addition to a 10-hole Short Course. with 24-hour manned security and gatehouse entrance.

Did You Know?

This mansion was once up for contingent sale, despite its enormous price.

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