Hawaii homes for sale starting at Fifty Thousand Dollars

$55,000,000 - Honolulu, HI

3735 Diamond Head Road Honolulu, HI - Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties, spanning over two acres across two adjacent parcels. Zoned R-7.5 and encompassing nearly 89,120 square feet, the estate features two residences and an open lot, offering sweeping ocean views, beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Offered as a singular acquisition under TMKs 1-3-1-039-042-0000 and 1-3-1-039-005-0000, Ho‘oluana Estate presents a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records. Last four digits of the listing TMK do not exist, these are used only for MLS entry purposes.

$50,000,000 - Kailua, HI

508 N Kalaheo Avenue Kailua, HI - Unparalleled, the Mele Komo Beachfront Estate located on the pristine shores of Kailua Beach, offers the most discerning connoisseur the ultimate in coastal living. With an impressive 12 beds and 13 baths, this 12,005 square-foot architectural marvel was meticulously designed prioritizing enjoyment with 9 ocean facing bedrooms and 11 private lanais. At 2.2-acres it's the largest residential lot on the Kailua Beachfront. The Primary Hale, boasting 6 beds and 6.5 baths within 5,835 sqft, and the Guest Hale, a companion masterpiece with 6 beds and 6.5 baths spanning 6,170 sqft, offer unparalleled living spaces designed with the perfect combination of luxury comforts and Hawaiian detail. Indulge in resort-style living with a 96,000 gallon pool showcasing a waterfall, slide, jacuzzi, and a private grotto. The 2,000 sqft Pool Cabana with a full kitchen, full bath, spacious loft, and laundry facilities adds an extra touch of convenience and comfort. Mele Komo provides the utmost in privacy and efficiency, featuring 94 photovoltaic panels, privately owned beach access, and stunning views of the famed Mokulua Islands. A unique opportunity to own a true jewel of the Hawaiian coastline.

$43,000,000 - Honolulu, HI

3735- Diamond Head Road Honolulu, HI - Located on Diamond Head Road, Ho‘oluana Estate is one of Honolulu’s last remaining legacy estate-sized properties. Zoned R-7.5 and encompassing nearly 80,000 square feet, the estate features an expansive residences and several open lots, offering sweeping ocean views, private/deeded beachfront access, and exceptional flexibility for development or preservation. Perfectly positioned between Kahala and Waikiki, this property combines luxury, tranquility, and proximity to world-class surfing, shopping, dining, golf, hiking, and more. Neighboring property located at 3735 Diamond Head Road A, is also available for sale, presenting a rare opportunity to establish a landmark estate in one of Honolulu’s most prestigious locations. Property details may not match tax records.

$38,000,000 - Makawao, HI

810 Piiholo Rd Makawao, HI - Discover Hokunui: 2 elegant homes on lot 3, with 8 SEPARATE Lots for a front yard, abundant water and microgrid power (with HECO option) located on 258 acres of rolling hills in Makawao, Upcountry Maui. With breathtaking views of the Ocean, West Maui Mountains and Haleakala, this unique property is a visionary blend of natural beauty, sustainable innovation and Hawaiian heritage. Designed as a regenerative agricultural self-sufficient community, the 9 lots offer the potential for up to 21 total lots and 42 residences (subject to approvals), with 6 active subdivisions being currently processed to realize this goal. Hokunui is water and energy self-sufficient, featuring a private water well with a 1.7 million-gallon-per-day allocation, and a state-of-the-art 1-megawatt solar microgrid with Tesla energy storage and a clean emissions backup generator. The two homes are LEED Gold certified; including a 4-bedroom, 3-bath main residence and a 2-bedroom, 2-bath guest cottage thoughtfully designed to harmonize luxury with environmental stewardship and stunning views. You will enjoy unparalleled amenities including private trails, equestrian paths, close proximity to Maui’s top schools, gorgeous beaches, quaint communities, Maui’s famous North Shore Ocean activities, and the Makawao Forest Reserve for hiking, biking and more. This remarkable estate offers limitless opportunities including a private self-sufficient safe haven for family and friends, a community subdivision, a private equestrian facility, a cultural hub, and/or a regenerative agricultural legacy. Contact your favorite Realtor today to explore this once-in-a-lifetime opportunity to own a self-sufficient slice of paradise in Upcountry Maui.

$38,000,000 - Makawao, HI

186 Piiholo Rd Makawao, HI - Discover Hokunui: Land for Sale. 9 SEPARATE Lots, 2 elegant homes on lot 3, abundant water and microgrid power (with HECO option) located on 258 acres of rolling hills in Makawao, Upcountry Maui. With breathtaking views of the Ocean, West Maui Mountains and Haleakala, this unique property is a visionary blend of natural beauty, sustainable innovation and Hawaiian heritage. Designed as a regenerative agricultural self-sufficient community, the 9 lots offer the potential for up to 21 total lots and 42 residences (subject to approvals), with 6 active subdivisions being currently processed to realize this goal. Hokunui is water and energy self-sufficient, featuring a private water well with a 1.7 million-gallon-per-day allocation, and a state-of-the-art 1-megawatt solar microgrid with Tesla energy storage and a clean emissions backup generator. The two homes are LEED Gold certified; including a 4-bedroom, 3-bath main residence and a 2-bedroom, 2-bath guest cottage thoughtfully designed to harmonize luxury with environmental stewardship and stunning views. You will enjoy unparalleled amenities including private trails, equestrian paths, close proximity to Maui’s top schools, gorgeous beaches, quaint communities, Maui’s famous North Shore Ocean activities, and the Makawao Forest Reserve for hiking, biking and more. This remarkable estate offers limitless opportunities including a private self-sufficient safe haven for family and friends, a community subdivision, a private equestrian facility, a cultural hub, and/or a regenerative agricultural legacy. Contact your favorite Realtor today to explore this once-in-a-lifetime opportunity to own a self-sufficient slice of paradise in Upcountry Maui.

$37,000,000 - Kihei, HI

7191 Makena Rd Kihei, HI - Makena Ranch spans nearly 160 acres in one of Maui’s most coveted regions, offering a rare combination of scale, flexibility, and scenic beauty along the island’s southern coastline. Despite its secluded ambiance, the property is just minutes from world-class resorts, pristine beaches, and celebrated golf courses, including the nearby Four Seasons and Makena Golf & Beach Club. Oriented to the west, Makena Ranch captures sweeping ocean and sunset views stretching from La Perouse Bay to Big Beach, punctuated by the silhouettes of Kaho‘olawe and Molokini. Elevated vantage points also reveal the dramatic contours of Maui’s mountainous interior, showcasing the island’s diverse landscapes in one sweeping view. A gated entrance and paved roadway introduce the estate, where underground utilities, a high-capacity private water system, and on-site fire protection offer both readiness and security. Private power generation and ample space for a solar array add potential for off-grid or hybrid energy solutions. Generous space and multiple parcels allow for a wide range of possibilities—whether creating a single private estate, establishing multiple residences, pursuing agricultural ventures, or dedicating portions of the land to conservation efforts. Free from homeowner associations or resort governance, Makena Ranch grants an uncommon level of autonomy in planning and development, giving you the freedom to shape the land to suit your vision. Beyond its physical attributes, this property offers a lifestyle defined by exclusivity and accessibility in equal measure. Enjoy the tranquil seclusion of rural Maui while staying close to five-star dining, spa services, championship golf, ocean sports, and the relaxed sophistication for which Makena is known. With its breadth of acreage, panoramic vistas, established infrastructure, and freedom from conventional restrictions, Makena Ranch is truly a blank canvas for those seeking to create a lasting legacy in one of Hawai‘i’s most desirable locales.

$31,000,000 - Kihei, HI

3254 S Kihei Rd Kihei, HI - Experience the pinnacle of oceanfront luxury in this stunning, 5 bedroom, 5 bath, plus 2 half bath, 7,244 sq. ft. estate. This over a half-acre property is located within the ideal stretch of Keawakapu Beach, offering unparalleled access to Maui’s most coveted shoreline a matter of steps from the home’s living room. This architectural triumph blends contemporary elegance and convenience with the island’s natural beauty, creating a private sanctuary of sophistication and rare serenity. Designed for those who appreciate refined living and grand entertaining, this estate features 5 spacious en-suite bedrooms, multiple areas for relaxed socializing, and a seamless indoor-outdoor flow that embraces the home’s stunning pool courtyard and oceanfront experience. Every room gifts an extraordinary vantage point of paradise – between sweeping ocean views in three master suites or tranquil poolside perspectives from the guest suites. At the heart of the home, the expansive pool and courtyard form a striking focal point, linking the media room, main entry, and living areas in perfect harmony. A private poolside retreat ensures both security and discretion, ideal for intimate gatherings or large-scale entertaining. Landscaped gardens with numerous palm trees and second-level sundecks off the guest suites provide elevated spaces to soak in a front seat view of unforgettable sunsets. A spacious oceanfront lawn offers ultra-privacy, featuring a fire pit that creates an inviting ambiance, shielded from public view and accessible only through a discreet, gated beach entrance. Whether you seek a primary residence, a lavish vacation home, or an island retreat, this estate is designed for those who desire premium beachfront living with an ultimate feel of privacy. A rare opportunity to own the most memorable oceanfront lifestyle in Maui.

$30,000,000 - Princeville, HI

3788 Ahonui Pl Princeville, HI - Ahonui Gardens, located on Kaua‘i's North Shore, is one of the largest and most versatile estate offerings in Hawai‘i. Spanning 50 acres, this estate comprises two lots, each with five units, totaling 10 units. Situated at the end of a quiet community roadway, it offers exceptional privacy, natural beauty, and a prime location.Ahonui Gardens provides a secluded, compound-like retreat, accessed via a gated, royal palm tree-lined drive. The estate includes a Spanish-modern style primary residence with over 4,200 sqft of refined interior space, designed to blend indoor and outdoor living in harmony with Kauai's natural beauty. The property also features two additional residences, expansive garages, a gazebo, yoga studio, gardening shed, kennel, chicken house, horse stable, and fenced pastures.The park-like grounds include gardens, pathways, streams, and abundant mountain and distant ocean views. The estate features a hardwood forest and a variety of avocado, mango, citrus, and other exotic trees, enhancing its natural beauty. A photovoltaic system ensures sustainable energy use.Ahonui Gardens is just minutes away from Hanalei Bay, pristine beaches, shops, dining, and renowned outdoor activities, offering a perfect balance of seclusion and convenience. The estate's superb location and flexible layout make it ideal as a legacy estate or a development opportunity for luxury homesites.Each of the two lots is approved for five luxury homesites (10 in total), allowing for further enhancement or development. This versatility makes the property suitable for creating a family compound, a corporate retreat, or selling individual parcels.Ahonui Gardens offers substantial size with exceptional potential in one of Kauai’s most desirable areas. The estate's size, location, and diverse features make it a unique and valuable asset for those seeking a serene lifestyle or a strategic investment.

$29,700,000 - Kamuela, HI

62-3680 Kiekiena Pl Kamuela, HI - Perched majestically atop 1.62 acres of prime ocean-view land within The Bluffs exclusive gated community at Mauna Kea Resort. Mauna Kea Resort, is a premier destination offering world-class amenities and 1800 acres of breathtaking natural beauty. The resort features two renowned hotels, the Mauna Kea Beach Hotel, and The Westin Hapuna, sited on 2 of the best beaches in Hawaii along with two championship golf courses; including the newly imaged Robert Trent Jones course. Include oceanfront tennis courts and you understand the rarity of this offering.This 6,300-square-foot sanctuary offers six private bedrooms and six and a half baths, seamlessly blending Balinese, Chinese, and Hawaiian design elements into an architectural masterpiece. The separate 4 Bedroom Guest Villa ensures peaceful multigenerational living. Celebrated by Architectural Digest, this estate epitomizes refined island living.The property celebrates the Big Island’s indoor-outdoor lifestyle, with over 2,000 square feet of covered lanai spaces. Custom-designed outdoor showers enhance the tropical ambiance, while 200 degree panoramic ocean views, including Maui, elevate the estate's allure. An outdoor kitchen and dining pavilion, surrounded by tranquil Koi ponds, create an idyllic setting for entertaining or quiet reflection. The 80 ft infinity-edge pool connects the main hale to the primary suite and poolside pavilions.After the dramatic bridge entrance over koi ponds, you enter the Great Room with high ceilings and retractable pocket doors that open to meticulously landscaped gardens. The adjacent @4 acres of unbuildable common area adds to the absolute privacy of the estate. A complete solar array provides sustainable power, underscoring harmony with the environment.Discover Hawaiian elegance at Hale Kiekiena, between two white sand beaches—where luxury and natural beauty converge.Be sure to click on the camera and the Video icon at the top of the page...fabulous!

$29,500,000 - Hanalei, HI

5-8192 Kuhio Hwy Hanalei, HI - Limahuli Ocean Estate is an incomparable 8.29-acre oceanfront property located at Kaua‘i’s iconic “end of the road” in Ha‘ena. With over 400 linear feet of pristine beachfront, the estate offers direct access to world-class surf and stunning views of the Pacific Ocean, Limahuli Valley, and the towering green peaks of Mt. Makana. The property comprises three parcels, offering the opportunity to expand the estate with additional improvements.Updated by Walker Warner Architects, the 3,123 sq ft main residence embraces fluid indoor-outdoor living with expansive lanais and floor-to-ceiling windows. A lush tropical landscape and surrounding preserved lands ensure natural beauty. Located just 20 minutes from Hanalei Town along one of Kaua‘i’s most scenic drives—with one-lane bridges, coastline views, and dramatic mountains—the estate offers both seclusion and accessibility.Additional features include a 1-bedroom, 1-bath caretaker’s cottage, a 490 sq ft pool, and an air-conditioned gym. Sustainability systems include photovoltaic panels with Tesla batteries, Starlink internet, and a whole-house water filtration system.Limahuli Ocean Estate is a rare offering in one of Kaua‘i’s most coveted locations.

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