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61-104 Iliohu Way, Haleiwa
$5,995,000
4 Beds ⋅ 3 Baths ⋅ 202606359 MLS ⋅ FS - Fee Simple Tenure
An exceptionally rare offering on Oahu’s North Shore, this legal NUC-permitted vacation rental is one of the last few fully permitted vacation rentals in the entire zip code. With annual income exceeding $500,000, it represents a compelling blend of established performance, long-term rarity, and an elegantly configured coastal property designed to support multiple private guest experiences. In a market defined by strict limitations and enduring demand, this is a true legacy-caliber STR asset.

61-104 Iliohu Way, Haleiwa

Listing courtesy of Outlive Homes LLC.

68-1002 Hoe Uli Way, KAMUELA
$5,950,000
6 Beds ⋅ 6 Baths ⋅ 734377 MLS ⋅ ['Fee Simple'] Tenure
A modern tropical residence set within the Mauna Lani resort community, designed for unhurried resort living on Hawaii Island. A rare opportunity to own a six-bedroom, six-bath residence with verified short-term vacation rental eligibility, offering exceptional flexibility and income potential. Approximately 3,401 square feet of living space on a generous 17,174-square-foot lot. Walnut custom cabinetry, natural quartzite countertops, and wood-beam ceiling details. New designer furnishings! Hawaii's indoor-outdoor lifestyle, featuring private bedroom wings surrounding a tropical courtyard, with expansive glass doors connecting the great room, dining area, and kitchen to the spacious poolside lanai. A private swimming pool and spa, outdoor kitchen, natural stone accents, and lush tropical landscaping. Energy-saving solar photovoltaic panels, battery storage, and a car charger. Nohea residents enjoy their own beautifully landscaped, on-site private amenity center featuring a free-form swimming pool, heated spa, fitness hale, gathering clubhouse with full kitchen, and two poolside BBQ pavilions. The renowned Mauna Lani Resort offers an extraordinary collection of amenities, including access to the Mauna Lani Private Beach Club with white sand, calm waters ideal for snorkeling and paddleboarding, beachfront lounging, and oceanfront dining at Napua Restaurant. Enjoy two championship golf courses, scenic coastal trails, historic Hawaiian fishponds, The Shops at Mauna Lani, and exceptional dining and spa experiences at the Mauna Lani Auberge and Fairmont Orchid resorts. An outstanding opportunity to own a brand-new luxury residence in one of the Kohala Coast's most desirable resort communities with views of the Mauna Lani golf course. Estimated completion: December 2026, subject to construction schedule. Artist's renderings illustrate the proposed design; finishes and landscaping are subject to change. Ideal vacation rental setup.

68-1002 Hoe Uli Way, KAMUELA

Listing courtesy of Better Homes and Gardens Real Estate Island Lifestyle.

44-375 Kaneohe Bay Drive, Kaneohe
$5,950,000
3 Beds ⋅ 2 Baths ⋅ 202606682 MLS ⋅ FS - Fee Simple Tenure
A rare opportunity to create a legacy waterfront estate on one of Kaneohe Bay’s most exceptional parcels. Stretching just shy of a full acre from Kaneohe Bay Drive to the ocean, this property offers a gentle, park-like slope framed by breathtaking views of the Ko’olau Mountains and iconic Coconut Island, with no view of the Marine Corps Base to interrupt the natural beauty. A winding driveway leads through a canopy of mature trees, creating a private and enchanting arrival experience. The expansive grounds provide a canvas for a world-class custom residence, resort-style pool, guest accommodations, and outdoor entertaining spaces designed to capture Hawaii’s indoor-outdoor lifestyle. An existing home provides rental income or a place to reside while planning and permitting your dream estate. Just moments away, the Kaneohe Bay Yacht Club offers a vibrant waterfront lifestyle with sailing, tennis, pickleball, live music, family events, and the renowned Thursday evening regattas that can be enjoyed from the property itself. Equally appealing, the world-famous Kailua Beach is only a short drive away. Properties of this size, setting, and potential rarely become available.

44-375 Kaneohe Bay Drive, Kaneohe

Listing courtesy of eXp Realty.

135 Kaimanu Pl, Kihei
$5,950,000
5 Beds ⋅ 4 Baths ⋅ 408014 MLS ⋅ Fee Simple Tenure
A rare South Maui estate — 2.118 acres in the exclusive gated community of Kaimanu Estates. This private retreat feels like living in Hana and Old Hawai‘i, surrounded by hundreds of native and fruiting trees including avocado, citrus, banana, lilikoi, guava and many more. With 4,718 sq. ft. in the main residence and a detached studio ohana, the property offers unmatched privacy and opportunity rarely found in South Maui. Just minutes away are Wailea’s world-class golf courses, resorts, fine dining, boutique shopping, and some of the best beaches in the world. Here you’ll find the perfect balance of tropical seclusion and resort-side convenience.

135 Kaimanu Pl, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

69-1634 Puako Beach Dr, KAMUELA
$5,900,000
3 Beds ⋅ 3 Baths ⋅ 721218 MLS ⋅ ['Fee Simple'] Tenure ⋅ Puako Sands Elua BLDG.
Nestled at the coveted north end of Puako Beach, this rare oceanfront offering enjoys unobstructed views across the largest state beach reserve in the area—guaranteeing natural beauty, privacy, and year-round serenity. With direct beach access, you’ll enjoy front-row seats to the humpback whale migration in winter and spectacular sunsets all year long. This classic Hawaiian-style residence has 9 foot vaulted ceilings and approximately 4000 square feet of indoor-outdoor living areas. This home features expansive covered lanais on both sides, perfect for entertaining or relaxing under the shade of mature trees, including a fruiting Hayden mango. Lush tropical landscaping and a rock wall with a gated driveway provide exceptional privacy. A rare opportunity to own a custom built Puako oceanfront home with a sprawling lawn, shade trees and a pathway leading you right to the sandy beach. Spectacular panoramic views of Puako, Waialea, Kawaihae, the Kohala Mountains, Maui, and the Pacific Ocean. Key Features: 2 Bedrooms+ Loft bedroom | 2 Bathrooms -office - main house 1 Bedroom | 1 Bath Legal Ohana unit for guests or rental income Resort zoning (V-1.25) allows for permitted Short-Term Vacation Rental (STVR) Split air conditioning throughout Two-car garage plus utility shed Built in 2001; well-maintained Included with a full price offer is a 2020 Jeep LP Gladiator with 21k miles! This is a rare opportunity to own an oceanfront estate in one of Hawaii Island’s most charming beach communities, with tide pools, sea turtles, and world-class snorkeling just steps away. Whether you seek a primary residence, a luxury vacation home, or an income-generating rental, this Puako gem checks every box. Offered furnished and move-in ready

69-1634 Puako Beach Dr, KAMUELA

Listing courtesy of Leilani Properties LLC.

44-519 Kaneohe Bay Drive, Kaneohe
$5,888,888
6 Beds ⋅ 6 Baths ⋅ 202611993 MLS ⋅ FS - Fee Simple Tenure
This truly exceptional waterfront estate on Kaneohe Bay offers rare wide oceanfront frontage, deep-water channel, and a private boat dock with direct access to the bay, sandbar, and open ocean. Sweeping panoramic views of Kaneohe Bay and the Koolau Mountains define this remarkable property. Just moments from Kaneohe Yacht Club, it delivers an unmatched boating lifestyle and a rare opportunity for multigenerational living or a private family compound on a 62,315 sq. ft. (nearly 1.5-acre) R-10 zoned parcel. The estate includes two dwellings. The main residence is a 3-bedroom, 3-bath home with vaulted ceilings, hardwood floors, and renovation potential PLUS an attached 1-bedroom, 1-bath unit offering its own entry, open floor plan, vinyl plank flooring, and covered lanai. A separate 2-bedroom, 2-bath guest residence features soaring vaulted ceilings and a wraparound deck, ideal for entertaining and relaxing. With expansive grounds, ample parking, and exceptional boating access suitable for larger vessels, this is a rare waterfront offering for those seeking space, privacy, and ocean recreation in one of Oahu’s most coveted settings.

44-519 Kaneohe Bay Drive, Kaneohe

Listing courtesy of REMAX Hawaii.

28 Moloaa Street, Honolulu
$5,850,000
5 Beds ⋅ 6 Baths ⋅ 202611061 MLS ⋅ FS - Fee Simple Tenure
This remarkable Estate on 21,832 sq ft lot. 4,577 sq ft of living space all on one level, including swimming pool. This 5 bedroom 5.5 bath has sweeping panoramic views of Diamond Head, Ocean, Mountains and the seasonal Whales, December thru March. Architectural elegance and exceptional craftsmanship throughout. Property to be conveyed "as is".

28 Moloaa Street, Honolulu

Listing courtesy of Tomoko Realty.

5171 Lower Honoapiilani Rd, Lahaina
$5,850,000
3 Beds ⋅ 3 Baths ⋅ 409059 MLS ⋅ Fee Simple Tenure
This unique Napili oceanfront residence is nestled on a coastal bluff in the center of the bay. It is protected from the risk of erosion. Views are unobstructed of the Pacific and the neighbor islands of Lanai and Molokai, as well as year round sunset views. The exceptional floor plan set over multi levels includes the living area overlooking the saltwater infinity edge pool, three bedrooms, three baths, an outdoor shower, and two-car garage. This special location offers front row seats to watch the surf at Little Makaha, whale watching in season, and turtles all year long. It is also accessible to private tide pools and the surf at Little Makaha. Additionally, the home is equipped with a Tesla battery and 68-panel photovoltaic system, which is grandfathered into the Net Energy Metering Program. The Net Metering agreement is transferable. Beaches, grocery stores, and restaurants are only a few minutes away. Napili is home to Maui Preparatory Academy and a short distance to Kaanapali and Kapalua Resorts.

5171 Lower Honoapiilani Rd, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

73-4425 Lemi Pl Unit 32, KAILUA KONA
$5,800,000
4 Beds ⋅ 5 Baths ⋅ 729380 MLS ⋅ ['Fee Simple'] Tenure ⋅ Hale Alani BLDG.
Hale ʻAlani 32 is a 4-bedroom, 4.5-bathroom home with 4,122 total sq. ft. positioned to welcome warm sunrise views over Hualālai and Mauna Loa Mountain on those clear Kona mornings. Designed for seamless indoor-outdoor living, the home features mahogany sliding pocket doors that open to approximately 544 sq. ft. of covered lanai space with outdoor dining, BBQ, pool & spa. The gourmet kitchen is equipped with premium Wolf & Sub-Zero appliances, bar seating, and an under-counter wine fridge, perfect for both everyday living and entertaining. The great room showcases vaulted ceilings and abundant natural light, enhancing the home’s open and inviting atmosphere. The primary suite offers a private retreat with an outdoor shower garden, creating a tranquil, spa-like experience. Offered fully furnished by Restoration Hardware, the home is move-in ready and thoughtfully designed to balance comfort, beauty, and the relaxed rythmn of island life.

73-4425 Lemi Pl Unit 32, KAILUA KONA

Listing courtesy of Kohanaiki Realty LLC.

47-478 Ahuimanu Road Unit A, Kaneohe
$5,775,000
3 Beds ⋅ 5 Baths ⋅ 202615587 MLS ⋅ FS - Fee Simple Tenure
This property has six homes. Each home has minimum lot size of 5,600 sq. ft. and up to 10,080 sq. ft. of land each with individual carports and hookups for full size washer and dryer. One house has 4 bedrooms, 2 baths; Two houses have 4 bedrooms, 2.5 baths; and Three houses have 3 bedrooms, 1 bath. All 6 homes are very private and are 6 single family dwellings. Driveway is shared by the 6 homes. Each home is a CPR and may be sold separately. Properties are in good condition and are currently rented.

47-478 Ahuimanu Road Unit A, Kaneohe

Listing courtesy of JW REALTY.

72-4085 Alahee Pl, KAILUA KONA
$5,750,000
6 Beds ⋅ 7 Baths ⋅ 734545 MLS ⋅ ['Fee Simple'] Tenure
Set on three expansive acres along the slopes of Hualālai Mountain, this exceptional Makalei Estates property offers a rare combination of privacy, sweeping panoramic ocean views, and refined Hawaiian living. A gated entrance opens to a beautifully landscaped driveway, creating a grand arrival to this remarkable estate surrounded by manicured tropical grounds and natural beauty. Thoughtfully designed for elegant living and gracious entertaining, the main residence features formal living and dining rooms, a wine cellar, and a welcoming family room with a fireplace. The chef’s kitchen is exceptionally appointed with a Wolf gas range, Sub-Zero refrigerator, a walk-in pantry, plus a casual dining nook. The primary suite offers a private retreat with its own fireplace, plus two walk-in closets and a luxurious ensuite bath featuring a spa tub, walk-in shower, and direct access to an outdoor shower. Two guest bedrooms, each with an ensuite bath, offer comfort and privacy. A recreation room with a pool table provides another inviting space to relax and gather. Accommodations extend beyond the main residence, offering exceptional flexibility for family and guests. A private studio guest suite with full bath is located above the garage. Separate from the main house, a two-bedroom ohana features its own living area, kitchen, and full bath.. The roomy three-car garage also includes a dedicated workshop. Designed for memorable gatherings, the expansive lanai offers multiple inviting spaces for relaxation and entertaining, including a fire-pit seating area, a separate fireplace lounge, and two dining areas accommodating ten and twelve guests. A well-appointed wet bar with a beverage refrigerator and dishwasher completes this impressive outdoor entertaining setting. The lap pool complements your daily exercise regimen. Energy-conscious features include an owned 35-panel PV system and solar panels to heat the pool. Video:https://player.vimeo.com/video/1237080207

72-4085 Alahee Pl, KAILUA KONA

Listing courtesy of Kona Pacific Realty.

2999 Makalei Place, Honolulu
$5,690,000
4 Beds ⋅ 6 Baths ⋅ 202604465 MLS ⋅ FS - Fee Simple Tenure
“House of Blue Heaven” — an extraordinary Diamond Head estate where architectural heritage meets timeless luxury. Originally designed in 1931 by renowned Hawaii architect Hart Wood, a pioneer of Hawaiian Regional architecture, this distinguished residence reflects his signature fusion of tropical indoor-outdoor living with Japanese and Asian-inspired design. Thoughtfully remodeled by celebrated architect Jeff Long in 1995, the home preserves its historic character while offering refined modern living. This 4-bedroom, 5.5-bath residence encompasses nearly 5,900 sq. ft. of interior living space on an 11,752 sq. ft. lot, with beautiful ocean and sunset views. Soaring ceilings enhance the home’s grand scale and invite abundant natural light throughout. Expansive lanais, a heated pool and spa, and sophisticated indoor-outdoor spaces create an exceptional setting for entertaining and relaxing. Separate guest quarters with private entrance provide flexibility and privacy. Just moments from Kapiolani Park, the Gold Coast, world-famous beaches, and Waikiki’s renowned dining and shopping, this is a remarkable expression of Hawaii architectural history and elevated island living.

2999 Makalei Place, Honolulu

Listing courtesy of REMAX Hawaii.

7465-C Koolau Road, KILAUEA
$5,600,000
4 Beds ⋅ 4 Baths ⋅ 715966 MLS ⋅ ['Fee Simple'] Tenure ⋅ Lani Na Kai BLDG.
Designed by Santo Giorgio and built in 2017, this stunning home is a masterpiece of Hawaii’s contemporary plantation-style architecture. Situated on nearly 3 acres and bordering 500 acres of ranch land, the property offers panoramic views of the iconic Waipake mountain range. Relax in your brand-new custom salt water pool with complete privacy and gorgeous views! Spanning 2,192 sqft of interior space with over 1,200 additional sqft of covered outdoor lanais, the 4-bedroom, 4-bathroom home is a harmonious blend of modern design and Hawaiian living. Triangular glass gable windows flood every room with natural light during the day and offer breathtaking stargazing at night. Each room opens to teak-covered lanais, effortlessly blending indoor and outdoor spaces around a lushly landscaped central courtyard and pool. Designed with comfort and views in mind, the great room, outdoor spaces, and ensuite primary bedrooms capture sweeping vistas and stunning sunrises. The ensuite bathrooms, featuring outdoor showers and a soaking tub, are designed for privacy and relaxation, embracing the island lifestyle. Each room is climate controlled with a newly installed split system AC. Sold mostly furnished with high end finishes and decor. The thoughtfully landscaped grounds include vibrant tropical plants, a manicured lawn, and a fruit orchard with citrus, bananas, and avocado trees that provide year-round enjoyment. Additional property features include a carport with storage and a potting area, an agricultural shed, and a beautifully hand-carved Balinese teak bale. Property is completely fenced, including a sprawling horse pasture, making this the perfect equestrian sanctuary. Conveniently located off a quiet country road, the home is within walking distance to Larsen's beach and a short drive to several stunning beaches, farmers’ markets, shopping, and dining. With everything this home offers, you’ll find it hard to leave this idyllic Hawaiian sanctuary.

7465-C Koolau Road, KILAUEA

Listing courtesy of COMPASS.

3063 Diamond Head Road, Honolulu
$5,560,000
4 Beds ⋅ 4 Baths ⋅ 202604939 MLS ⋅ FS - Fee Simple Tenure
This is not just a rare landmark home standing proudly between the slopes of Diamond head and the turquoise warm waters of Honolulu’s Gold Coast. It is a lifestyle. Completely remodeled in 2000, this home is the only home available in this highly sought after walkable Diamond Head neighborhood. Walk to the sandy beach at Makalei Beach Park, less than one block away, as well as the Gold Coast, Kapiolani Park and Waikiki. This 4 bedroom 4 bathroom 3631 sq. ft. home with pool, rooftop deck with ocean views home is walled, gated, serene and secure. The surroundings provide visual drama with a cool and shaded fully landscaped garden and pool surrounding the home all set between the slopes of Diamond Head and the Pacific Ocean. This property is a sanctuary. A secure tropical urban paradise surrounded by the air and the water in one of the most desirable and rarely available locations on O'ahu. The layout, size and design of this large and well conceived home in one of the best locations is truly special.

3063 Diamond Head Road, Honolulu

Listing courtesy of Compass.

59-659 Ponoholo Trail, KAMUELA
$5,500,000
4 Beds ⋅ 4 Baths ⋅ 734250 MLS ⋅ ['Fee Simple'] Tenure
Nestled within the private, gated enclave of Kohala Ranch on the Big Island of Hawaii, this home is a true sanctuary in paradise. Set on a sprawling acre in the desirable Heathers II section, this exquisite 4-bedroom, 3.5-bathroom residence promises unmatched panoramic views of the Kohala Coastline, as well as the majestic sights of Mauna Kea and distant Maui. Imagine retreating to the spacious great room or unwinding on the expansive covered lanai, where an infinity pool and spa create a serene oasis perfect for savoring the island's dramatic sunsets all year long. The harmonious blend of indoor and outdoor living is accentuated by breathtaking ocean vistas visible from the great room, master suite, kitchen, and two additional bedrooms. The master suite is a haven of relaxation, complete with a walk-in closet, dual sinks, an inviting walk-in shower, an al fresco shower, and a separate, luxurious bathtub. Modernity touches every corner of this home, with sleek Italian cabinetry and sophisticated tile work spanning its entirety. The property's custom landscaping is as thoughtful as the home's design, set amidst a backdrop of easy access to hiking trails, pristine beaches, and championship golf courses. All the while, you're just moments from the cultural hub of Waimea, with its horseback riding, opulent resorts, and fine dining options.

59-659 Ponoholo Trail, KAMUELA

Listing courtesy of Family Hawaii Realty.

3473 Paty Drive Unit 243A, Honolulu
$5,500,000
5 Beds ⋅ 6 Baths ⋅ 202615998 MLS ⋅ FS - Fee Simple Tenure
A rare sanctuary nestled above the lush foliage of Manoa Valley, this extraordinary furnished estate offers an unparalleled sense of privacy, serenity, and connection to nature. Set on approximately 9.48 acres of beautiful hillside land, this exceptional retreat feels worlds away while remaining conveniently close to Honolulu. The 6,411-square-foot residence features 5 bedrooms, 4 full and 2 half baths, soaring ceilings, expansive windows, refined finishes, and seamless indoor-outdoor living. A 2021 update added a sleek glass elevator. Breathtaking valley, ocean, city, and sunset views unfold throughout the home. Outside, a heated, ionized infinity pool and separate spa create a private resort-like setting, complemented by a built-in grill and multiple outdoor spaces for entertaining or quiet reflection. An owned 39-panel solar PV system and separate solar hot water enhance the home's energy efficiency. More than a residence, this is a true private haven where luxury, nature, privacy, and tranquility converge in one of Honolulu's most coveted valleys.

3473 Paty Drive Unit 243A, Honolulu

Listing courtesy of Coldwell Banker Realty.

1100 Kaimoku Place, Honolulu
$5,500,000
4 Beds ⋅ 5 Baths ⋅ 202615121 MLS ⋅ FS - Fee Simple Tenure
Directly fronting the 7th hole fairway of Waialae G/C (home of the PGA Sony Open), this classic country-style Honolulu home offers a timeless island retreat on generous lot. Exterior and interior repainting and some touch-ups completed in August 2026! The 4-bedroom, 4.5-bathroom floor plan provides exceptional comfort and charm. The entire second floor is dedicated to a massive primary suite complete with a classic bath that captures a golf course and serene peekaboo ocean view. The ground level features three additional bedrooms, perfect for hosting family and guests in a warm, character-rich home. The Seller requests closing date to be after January 4, 2027.

1100 Kaimoku Place, Honolulu

Listing courtesy of Seven Signatures International.

525 Moaniala Street, Honolulu
$5,500,000
5 Beds ⋅ 6 Baths ⋅ 202604792 MLS ⋅ FS - Fee Simple Tenure
Hawaii Loa Ridge is one of Oahu’s most prestigious residential enclaves. Privately positioned within the secluded gated community of The Pointe, this remarkable estate captures commanding ocean vistas and sweeping panoramas stretching toward Koko Head Crater. Designed by architect Mark Lively, the five-bedroom, five-and-a-half-bath Mediterranean masterpiece reflects timeless architectural elegance and exceptional craftsmanship throughout. The main level unfolds with a gracious formal dining room, an expansive family room, and a sumptuous primary suite retreat. A grand living room opens seamlessly to the resort-style pool terrace, where shimmering ocean views create an unforgettable backdrop. Upstairs, an additional en-suite bedroom, a secondary lounge, and two adjoining bedrooms provide both comfort and flexibility. A private maid’s quarters is discreetly integrated for added convenience. An extraordinary offering in one of Honolulu’s most coveted neighborhoods, this residence epitomizes elevated island living — where scale, privacy, and breathtaking horizons converge in effortless sophistication. Property to be conveyed "As Is".

525 Moaniala Street, Honolulu

Listing courtesy of ECentury Homes Hawaii LLC.

4700 Kapuna Rd, PRINCEVILLE
$5,500,000
5 Beds ⋅ 5 Baths ⋅ 727543 MLS ⋅ ['Fee Simple'] Tenure ⋅ Waipake Heights BLDG.
Surrounded by tropical landscapes and expansive views, this private 3.55 acre estate in Kilauea on Kauai's North Shore offers a rare combination of seclusion, flexibility, and distinctive amenities. Designed to support a variety of lifestyles, the property combines luxury living with space for creative pursuits, equestrian activities, and agricultural use. The residence features 5 bedrooms and 4.5 bathrooms, with a layout that accommodates multi generational living, extended guest stays, remote work, and entertaining. The primary suite captures sweeping ocean views and includes a spacious en suite bath with a Jacuzzi tub. High wood beam ceilings add warmth and character throughout the main living areas, while the chef's kitchen serves as a central gathering space. Unique features elevate the property beyond a traditional luxury home. An architectural library with a striking octagonal beam ceiling provides a distinctive setting for reading, study, or work. A dedicated art studio offers space for creative endeavors, while a media room, storm shelter, and dedicated laundry wing contribute additional functionality. Multiple lanais, including a screened lanai, create seamless indoor and outdoor living. Outdoor amenities are equally impressive. A heart shaped pool with a waterfall feature is framed by custom lava rock walls, creating a memorable setting for entertaining or quiet relaxation. Beyond the residence, the estate includes a horse pasture, agricultural improvements, and a separate agricultural building, offering flexibility for a range of agricultural and equestrian interests. Located in Kilauea, the property enjoys convenient access to North Shore beaches, surf destinations, the Historic Kong Lung Center, Ahuimanu Shopping Center, local dining, Princeville Airport, and the Princeville Resort area with the acclaimed Makai Golf Course. Combining privacy, ocean views, 3.55 acres of usable land, and distinctive estate amenities.

4700 Kapuna Rd, PRINCEVILLE

Listing courtesy of Aloha Sotheby's Intl Realty - Kaua'i.

454 Hoolawa Rd, Haiku
$5,500,000
2 Beds ⋅ 2 Baths ⋅ 407170 MLS ⋅ Fee Simple Tenure
Outside the box, Inside the box... the choice is yours. Welcome to the QK Haiku, homegrown Maui modernism at its best. Located oceanfront in a diverse and welcoming north shore agricultural neighborhood, the QK offers concise modern living - everything you need, and nothing you don't. Designed in collaboration with Maui Architectural Group, the project combines state of the art energy and water self sufficiency with a minimalist architectural form that gets out of the way of the bold and energetic oceanfront setting. The two rectangular forms use transparency to minimize their boundaries to the natural world, while cleverly concealing water catchment, solar electricity harvesting and battery storage. The 2 bedroom house with its living green roof is tucked into the earth, and the art gallery-like farm office floats above the property tucking itself into the sky. Seclusion can be enjoyed here without loneliness as Hoolawa road has a great community and even its own cafe and gathering space. The land offers the possibility of building another main residence. Entertaining... Contemplation... Growing Food... What will you do when you move in?

454 Hoolawa Rd, Haiku

Listing courtesy of Hawaii Life (W).

81-6513 Laupai Way, KEALAKEKUA
$5,499,000
3 Beds ⋅ 4 Baths ⋅ 734953 MLS ⋅ ['Fee Simple'] Tenure
Visit this brand-new contemporary residence that captures the essence of refined island living within Hokuli’a, one of Hawaii Island’s most exclusive private equity golf communities. A beautiful entry opens to sweeping ocean views and the light breezes of the local trade winds. Wide-plank white oak floors lead through the great room into a chef’s kitchen finished with bespoke white oak cabinetry and a custom coffee bar. Rich marble and quartzite surfaces, expansive glass doors, and carefully considered details create a seamless connection between interior elegance and the outdoors. The private primary wing is a true retreat, offering expansive ocean views and a spa-inspired ensuite featuring a secluded outdoor rock-wall shower. A separate guest wing provides privacy and comfort with two ensuite bedrooms and its own laundry facilities. Outside, the estate becomes a private resort. Generous lanai spaces, custom pool with bench seating, a gas fire pit, and a full outdoor kitchen invite al fresco dining and relaxed entertaining beneath the Kona sky. Set on 1.1 acres along a quiet, gated cul-de-sac, the grounds are thoughtfully landscaped with native grasses, fruit trees, traditional rock walls, atmospheric lighting, and tiki torches. A two-car garage with dedicated golf-cart parking completes the offering. As a member of Hokuli’a, you gain access to a world-class private club experience: a Jack Nicklaus Signature golf course, a full-service clubhouse with open pavilion dining, a lap pool, fitness center, spa, courts, and extensive hiking trails across the community’s shoreline park. This is more than a residence — it is a rare opportunity to own a newly completed, design-forward home within one of Hawaii’s most private and prestigious golf communities, where ocean views, championship golf, and uncrowded acreage define everyday life. A Club Membership valued at $150,000 is included in the purchase price.

81-6513 Laupai Way, KEALAKEKUA

Listing courtesy of Aloha Sotheby's Intl Realty - Hawai'i.

1036 Mokulua Drive, Kailua
$5,498,000
4 Beds ⋅ 4 Baths ⋅ 202614113 MLS ⋅ FS - Fee Simple Tenure
Special Lanikai beachside retreat just steps away from sparkling turquoise waters, with iconic Mokulua Island views just beyond the white sandy beach. This plantation-style home exudes charm, warmth, character, and offers resort-like living--swim, snorkel, sail, kayak, or paddle board, right out your door. An architect-designed gate welcomes you into lush landscaping with mango, banana trees, tropical plants, and flowers. The inviting living room w/impressive wood-vaulted ceilings and slate flooring opens through French doors to a a large covered lanai, ideal for family gatherings and entertaining. Gourmet kitchen features Thermador gas stove/convection oven, full-sized Miele freezer & refrigerator, walk-in pantry, wine refrigerator and bar area. The spacious primary suite upstairs showcases Australian eucalyptus hardwood floors, vaulted ceilings, built-in desk, wet bar, walk-in closet, wraparound lanais, and rooftop deck with Ko'olau mountain, Lanikai Pillbox, and ocean views. Enjoy early morning swims, backyard fire pit, hot/cold outdoor shower, two-car garage, & guest parking. A heavenly Lanikai property where indoor/outdoor living is a daily treat just steps from sand and sea.

1036 Mokulua Drive, Kailua

Listing courtesy of Hawaii Life.

5033 Lau Nahele St, KOLOA
$5,495,000
4 Beds ⋅ 4 Baths ⋅ 732005 MLS ⋅ ['Fee Simple'] Tenure ⋅ Kukuiula BLDG.
Discover a rare opportunity to own two custom cottages on a single fee simple homesite in the Kaulu neighborhood of Kukuiʻula on Kauaʻi. Designed with timeless Hawaiian Plantation inspired architecture, this exceptional property reflects the character and craftsmanship that define one of Kukuiʻula’s highly sought-after neighborhoods. Ideally located between The Club at Kukuiʻula and The Shops at Kukuiʻula, Kaulu is known for mature tropical landscaping, garden pathways, tranquil water features, and convenient access to golf, wellness, dining, and shopping. The property features two separate single-level residences, each offering two bedrooms, two bathrooms, and approximately 1,640 square feet of living space, for a total of four bedrooms, four bathrooms, and approximately 3,280 square feet. The dual cottage design offers exceptional flexibility for hosting guests, multigenerational living and vacationing, or creating a private retreat while maintaining privacy. Both homes showcase quality craftsmanship, featuring hardwood flooring, custom sapele cabinetry, spacious kitchen islands, Thermador, Wolf, and Sub-Zero appliances, vaulted and tray ceilings, and generous screened covered lanais that create a seamless connection to outdoor living. The primary suites feature soaking tubs, walk-in showers, outdoor rainforest stone showers, and thoughtfully designed dressing areas. Each cottage enjoys its own private tropical in-ground spa surrounded by native landscaping and BBQ area, creating a peaceful setting for relaxation. Additional features include a climate-controlled garage, owned solar, battery backup, a Tesla charging station, and generous driveway parking.

5033 Lau Nahele St, KOLOA

Listing courtesy of Aloha Sotheby's Intl Realty - Kaua'i.

917 Iiwi Street, Honolulu
$5,495,000
5 Beds ⋅ 6 Baths ⋅ 202612065 MLS ⋅ FS - Fee Simple Tenure
Privately gated and offered fully furnished, this exceptional Mediterranean-inspired estate evokes the ambiance of a private resort. Crowned by a striking turquoise tile roof and surrounded by lush tropical landscaping, the residence blends timeless architecture with Kahala's coveted indoor-outdoor lifestyle. Designed by Pyramid Premier Properties, the home features 5 bedrooms, a den, and 5.5 baths, including dual primary suites—one on the main level and another upstairs. Thoughtfully designed for both everyday living and gracious entertaining, the chef's kitchen is appointed with a Sub-Zero refrigerator, 60-inch Viking gas range, walk-in pantry, and abundant storage. Outside, a private oasis unfolds with a sparkling heated pool, spa, cascading waterfall, and Badu swim jet system for exercise. A whimsical bridge and separate pool cabana with full bath complete the resort-like setting. With an oversized garage, gated entry, and beautifully curated living spaces throughout, this remarkable Kahala retreat offers a rare blend of elegance, comfort, and escape.

917 Iiwi Street, Honolulu

Listing courtesy of Hawaii Life.

1600 Lower Nahiku Rd, Hana
$5,495,000
4 Beds ⋅ 4 Baths ⋅ 406329 MLS ⋅ Fee Simple Tenure
Self Sustaining Tropical Estate and Cacao Farm - Potential for Seller Financing - Nestled between two river streams on Maui’s serene east end, this extraordinary 14.9-acre tropical estate and working farm offers a rare chance to embrace an off-the-grid lifestyle in true paradise. Designed for self-sustainability at its finest, this unique gentleman’s and ladies’ farm features a deep water well providing pristine drinking water, a powerful state-of-the-art solar energy system, modern septic systems, and acres of mature, fruit-bearing cacao trees. The land is also rich with juicy tropical fruits and vibrant flowering plants. Currently home to approximately 600 cacao trees, the property has the potential to expand up to 11,500 trees. Additionally, an adjacent 180 acres may be available, supporting up to 180,000 more trees. As global cacao production declines and chocolate prices soar, Hawaii is emerging as a prime location for cacao cultivation—making this a timely and strategic investment. Located just 600 feet from the ocean, the estate is exceptionally private and peaceful, with lush botanical surroundings, sweeping ocean views, and three separate access points. Bordered by streams and wrapped in natural beauty, this tropical sanctuary offers unparalleled tranquility, sustainability, and the luxury of living in harmony with nature.

1600 Lower Nahiku Rd, Hana

Listing courtesy of Coldwell Banker Island Prop(S).

132 Poipu Drive, Honolulu
$5,493,000
4 Beds ⋅ 4 Baths ⋅ 202601273 MLS ⋅ FS - Fee Simple Tenure
Luxury living beyond expectations - Sweeping, breathtaking views unfold in a way that can only be fully appreciated in person. Meticulously redesigned and rebuilt, the home blends architectural sophistication with tranquility, oriented to capture expansive ocean views, mountain ranges, and iconic Diamond Head stretching as far as the eye can see. High ceilings, an open floor plan, and beautiful finishes elevate both form and function, with the home thoughtfully designed for effortless entertaining. Expansive living spaces and a seamless indoor/outdoor flow create the perfect setting for gatherings, allowing the home to live as beautifully as it looks. The architectural design is further enhanced by premium, custom-made and imported Eagon aluminum doors engineered for luxury living, offering exceptional thermal performance and effortless function. Refined design, coastal serenity, and craftsmanship that speaks for itself. Walk through video and upgrades and features list attached. Rebuilt in 2023!

132 Poipu Drive, Honolulu

Listing courtesy of Coldwell Banker Island Prop.

41-539 Makakalo Street, Waimanalo
$5,400,000
3 Beds ⋅ 2 Baths ⋅ 202619098 MLS ⋅ FS - Fee Simple Tenure
A Rare Waimanalo Opportunity: Where Country Living Meets Exceptional Possibilities. Perfect for equestrian enthusiasts, ranchers, farmers, and those seeking a truly unique piece of paradise. Set against the dramatic beauty of the Ko'olau mountains, this private, fully fenced property offers a remarkable combination of natural beauty, usable space and convenient access to town. Enjoy the peaceful, open atmosphere of Waimanalo while remaining close to its beautiful white-sand beaches. Featuring two cottages, over 26,000 square feet of warehouse, office space, and other roofed area. Surrounded by O'ahu’s lush windward landscape and magnificent mountain views, it’s more than just a property; it’s an opportunity to create a distinctive lifestyle, agricultural operation, or private retreat in Waimanalo’s scenic setting. Private. Fully fenced. Expansive. Versatile. Enjoy the beauty and tranquility of country living while staying connected to the conveniences of O'ahu. Priced under the appraised value!

41-539 Makakalo Street, Waimanalo

Listing courtesy of Coldwell Banker Realty.

75-656 Makalauna Pl, KAILUA KONA
$5,300,000
5 Beds ⋅ 5 Baths ⋅ 734679 MLS ⋅ ['Fee Simple'] Tenure
Rarely does an estate of this caliber come to market on Hawaiʻi Island. Set on nearly two private acres above Kailua Bay, this Lucky Bennett-designed residence is a study in scale, craftsmanship and island grace. A long private drive winds through mature gardens to a grand four-car carport pavilion, built to match the residence, and a courtyard with a stone water feature, where the view opens straight through the home to the Pacific. Within 5,830 square feet of single-level living, warm teak and mahogany run throughout beneath soaring coffered ceilings washed in cove lighting. Walls of glass slide away entirely, dissolving the line between home and island. The great room and the dining area flow as one onto 1,354 square feet of covered lanai. The chef's kitchen, anchored by a French range, opens through a window counter to the lanai bar. Beyond, a 75-foot infinity-edge pool and travertine spa stretch toward the horizon. Lounges, outdoor dining, a koi pond and fire bowls invite long evenings as the sun sets over the Pacific and the lights of Kona town glow along the coast. Five bedrooms and four and a half baths offer privacy throughout. The primary suite opens to the lanai and ocean views, with a custom wood dressing room and a spa-inspired bath of river stone sinks and a soaking tub framed in live-edge wood. One bedroom opens to a private lanai among the treetops. A separate guest retreat offers its own living space, wet bar and garden courtyard, while a game room lined with library shelving flows into an office with its own garden lanai. Thoughtfully refreshed with designer lighting, a renewed pool, new plantings and an owned photovoltaic system, the home is ready for its next chapter. Framed by lava rock walls and terraced lawns, with mango and an abundance of fruit trees bearing throughout the grounds, this is one of Hawaiʻi Island's premier estates. A Kona legacy, made for gathering.

75-656 Makalauna Pl, KAILUA KONA

Listing courtesy of Coldwell Banker Island Properties - Kona.

3955 Round Top Drive, Honolulu
$5,300,000
5 Beds ⋅ 3 Baths ⋅ 202618721 MLS ⋅ FS - Fee Simple Tenure
Perched high above Honolulu on Round Top Drive, this extraordinary estate spans six parcels totaling 76,970 square feet and offers a rare combination of privacy, history, and unrivaled panoramic views stretching from Diamond Head and the Pacific Ocean across the Honolulu skyline to Manoa Valley and the surrounding mountains. Held by the same family for nearly a century, the property is anchored by a 5-bedroom, 3-bath residence with a total of 3,360 square feet of interior living space. Originally built in 1937 and later expanded with an addition designed by renowned architect Alfred Preis, the home retains distinctive midcentury features and character throughout. A separate downstairs living area with its own kitchenette offers flexibility for extended family, guests, or rental use. Decades of thoughtful landscaping have created lush, established grounds with mature koa and fruit trees and a remarkable sense of privacy. The estate also presents significant potential for additional residences, a multi-generational compound, or a thoughtful reimagining, subject to buyer due diligence. A rare opportunity to own a legacy property of this scale, setting, and character in Honolulu.

3955 Round Top Drive, Honolulu

Listing courtesy of Compass.

59-011 Kamehameha Highway Unit B, Haleiwa
$5,300,000
5 Beds ⋅ 5 Baths ⋅ 202611319 MLS ⋅ FS - Fee Simple Tenure
RARE North Shore luxury retreat with panoramic ocean views to Kaena Point! Elevated approx. 85 ft above sea level and outside the flood zone, enjoy peace of mind, cooling trade winds, and seasonal whale watching from your own property. Ideally located near the world-famous "7 Mile Miracle" surf breaks, Haleiwa, and Turtle Bay Resort. The expansive 5 bedroom, 4 bath main home offers open-concept living, seamless indoor-outdoor flow, and a grand porte-cochere entry. Resort-style grounds feature a pool, jacuzzi, covered outdoor grill, cabana, and hotel quality turf lawn--perfect for entertaining. A detached guest house with full bath plus an attached apartment WITHIN the main home (separate entry + kitchenette) creates strong multi-generational living or income potential. Opportunities like this are limited-- secure your piece of North Shore paradise before it's gone. One or more photos have been enhanced.

59-011 Kamehameha Highway Unit B, Haleiwa

Listing courtesy of Keller Williams Honolulu.

Based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on . Information is deemed reliable but not guaranteed. Copyright: 2026 by HiCentral MLS, Ltd. IDX information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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