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59-635 Akanoho Place, Haleiwa
$3,500,000
4 Beds ⋅ 5 Baths ⋅ 202418617 MLS ⋅ FS - Fee Simple Tenure ⋅ 437 DOM
Price Reduction! Incredible 1.234 Acre Estate with a 3 Level Custom Home and an interior elevator. Also: 2 double-car Garages, 6 person Spa-Hot-Tub, Gourmet-Kitchen and Fully-Furnished! This home looks into a tropical forest valley for the most peaceful setting in all of Pupukea and watching the sunset in the ocean beyond is fantastic! Much cooler and quieter than any properties down below (therefore the fully operational wood burning fireplace) yet every room is air-conditioned with separate Split-Air Systems. Cool & Quiet is a key feature yet just minutes to world-famous beaches, Historic Haleiwa Town and Turtle Bay Resort. Cathedral Ceilings and floor to ceiling windows bring in the light and dramatic views! Every room is pre-wired w/Fiber-Optics and Co-Axle Cable plus a Full Security System, Formal Dining Room, hardwood floors and Majestic Entry-Foyer and an entire lower level perfect for Hobby Workshop or a huge workout room (elevator stops at this ground level). One of the most dramatic estates in all of Pupukea Highlands and perfect for an extended family or mountaintop retreat! Must see to truly appreciate. Country Living at its Best!

59-635 Akanoho Place, Haleiwa

59-380 Wilinau Road, Haleiwa
$3,092,500
3 Beds ⋅ 3 Baths ⋅ 202601536 MLS ⋅ FS - Fee Simple Tenure ⋅ 113 DOM
Perched in the highly coveted Sunset Hills neighborhood of Pupukea, this exceptional North Shore estate captures the essence of elevated island living. A rare opportunity to own a legacy property in one of Oahu’s most exclusive and tightly held enclaves, where panoramic ocean views, privacy, and enduring value converge. From sunrise to sunset, the home is immersed in breathtaking, views of the Pacific Ocean extending to Ka?ena Point. Designed for single-level living, every room is thoughtfully oriented toward the ocean, allowing each space to frame endless blue horizons, cooling trade winds, and abundant natural light throughout the day. A large wraparound lanai anchors the home, creating a seamless indoor-outdoor connection. Ideal for entertaining or quiet moments alike, the lanai features a dedicated outdoor dining area with a full dining table, surrounded by integrated tropical planting that enhances privacy while framing the dramatic ocean backdrop. This expansive outdoor living space becomes a natural extension of the home—perfect for sunset dinners, morning coffee, and year-round enjoyment of the North Shore lifestyle.

59-380 Wilinau Road, Haleiwa

59-414 Makana Road Unit 2, Haleiwa
$2,500,000
4 Beds ⋅ 4 Baths ⋅ 202519957 MLS ⋅ FS - Fee Simple Tenure ⋅ 260 DOM
Lifetime opportunity to own 1.5 acres of prime real estate in Pupukea at an unbeatable price! Found on a prized rim lot location between Waimea Bay and Sunset Beach, in the highly coveted subdivision of Sunset Hills. Perched above Oahu's fabled North Shore, this property provides unobstructed views from Ka'ena Point to the world-famous Banzai Pipeline surf break- so close you can hear the waves breaking and watch surfers take off! Several terraced areas offer plenty of room to expand your dream estate- room for an infinity pool and spa included! Buffered by the Pupukea Forest Reserve, offers valley views too- with a unique rock outcrop to gaze upon. You couldn't find a spot on this lot without a breathtaking view to take in. Access to the property includes a curved, paved driveway that leads to a private 4 bedroom home. Sandy coastline views, captivating sunsets, and consistent trade winds add to the property's charm and appeal. Mature fruit trees are a symbol of the abundance this land has to offer. Highly valued in this area is an existing septic system, approved for use up to 5 bedrooms. This is a newly developed CPR. Unit 1 is also listed for sale- 1/2 acre for $2,200,000.

59-414 Makana Road Unit 2, Haleiwa

59-555 Makana Road, Haleiwa
$2,500,000
3 Beds ⋅ 1 Baths ⋅ 202518741 MLS ⋅ FS - Fee Simple Tenure ⋅ 79 DOM
Incredible cedar home located in the peaceful and secluded “Sunset Hills” —a highly desired private community in Pupukea, on the North Shore of Oahu. This home sits on more than an acre of land, with beautiful tropical landscape, a 4-car garage, and a greenhouse. The property features a cemented driveway with ample parking space, and is secured by a gated entrance with private code access. The oversized garage is newly renovated with split ACs, large ceiling fans, full insulation, ample space, and a half bath —making it perfect for an indoor gym, workshop, or creative studio. This versatile space adds immense value to the property. The home itself is equally impressive, with 3 bedrooms, 1 bathroom, kitchen, dining area, laundry room, and a lanai with ocean view. With vaulted ceilings and a warm, inviting, and well-kept space, you will love the cozy cabin feel of this home, as well as waking up to the sound of singing birds. With plenty of land, you’ll love the serenity and natural beauty surrounding this property. The lush, well-maintained lawn offers expansive open space perfect for gardening, entertaining, and room to build future additions.

59-555 Makana Road, Haleiwa

59-507 Pupukea Road, Haleiwa
$2,200,000
3 Beds ⋅ 2 Baths ⋅ 202607457 MLS ⋅ FS - Fee Simple Tenure ⋅ 86 DOM
Welcome to this quiet and peaceful Hawaiian-style home, set on a full acre of lush tropical landscaping and vibrant flowers, shaded by two magnificent monkey pod trees. The level property features a stretch of soft green lawn and a charming old stone built-in barbecue, perfect for gathering with family and friends. Inside, the home offers high ceilings and warm wood tones throughout, creating a comfortable, island-inspired atmosphere. The open kitchen flows easily into the living spaces, complemented by 3 bedrooms and 1.5 baths. Start your mornings on the covered lanai, sipping coffee while surrounded by serene natural beauty. A truly rare find. Home is being sold “as is.” *Additional photo and video- COMING SOON!

59-507 Pupukea Road, Haleiwa

59-720 Kanalani Place, Haleiwa
$2,120,000
4 Beds ⋅ 3 Baths ⋅ 202519639 MLS ⋅ FS - Fee Simple Tenure ⋅ 50 DOM
Tucked away at the end of a palm lined driveway, this must see private 1+ acre estate offers lush surroundings with mango banana and puakenikeni trees. Your tropical sanctuary features ocean views from nearly every room, a deep tile swimming pool overlooking a fully useable 1 acre yard which is perfect for get togethers and celebrations. Also, a huge three car garage and plenty of parking for boats, jet skis, dirt bikes, classic cars and all your toys! The 3 bedroom 2 bath upstairs combined with a large 1 bedroom, 1 bath ground level unit with living room, fireplace, wet bar, and two private entrances perfect for multigenerational living or rental income. The upstairs home features a fireplace, vaulted ceilings, large bedrooms, and HUGE lanai overlooking the ocean. Each bedroom has a lanai just outside the door to take advantage of the views and cool breezes of Pupukea. *School district information taken from Hawaii DOE School Finder website. Buyer to verify. *Bedroom count on MLS and tax records does not match. *Check out 3-D and aerial tours!

59-720 Kanalani Place, Haleiwa

59-586 Pupukea Road, Haleiwa
$2,100,000
5 Beds ⋅ 4 Baths ⋅ 202608956 MLS ⋅ FS - Fee Simple Tenure ⋅ 70 DOM
Rare opportunity in coveted Pupukea on Oahu’s North Shore. Set on 1.27 acres of lush, wooded land, this private retreat offers a peaceful lifestyle surrounded by nature. Two gated driveways create a true sense of privacy and arrival, while the expansive grounds provide flexibility for multi-generational living, entertaining, or simply enjoying the space and serenity. The property features split AC systems, a fireplace, outdoor shower, stone pizza oven, gazebo, generous storage, and parking for 6+ vehicles including boat parking. Mature landscaping and a thoughtfully spread-out layout create a secluded retreat with the convenience of nearby North Shore beaches, hiking trails, and outdoor recreation. A rare North Shore offering with space, privacy, and endless potential.

59-586 Pupukea Road, Haleiwa

59-496 Pupukea Road, Haleiwa
$1,975,000
5 Beds ⋅ 3 Baths ⋅ 202517264 MLS ⋅ FS - Fee Simple Tenure ⋅ 103 DOM
TWO PERMITTED HOMES + STUDIO on Private, Gated Acre in Pupukea This rare level one-acre parcel features 2 permitted homes plus an additional studio, offering incredible flexibility and income potential. HOME 1: 3 Bedrooms | 1 Bath | Expansive exterior deck HOME 2: 2 Bedrooms | 1 Bath STUDIO: Separate entrance, full kitchen & bath. Actual/previously earned Net Operating Income of $105,525/year-live in one & rent out the others, rent all 3, or expand existing structures and/or build an Ohana (subject to approval). Tastefully updated with high-quality finishes thruout: Hardwood & tiled floors, fully tiled bathrooms with marble showers, and updated kitchens Located just minutes from Haleiwa town and the world-famous North Shore beaches, this is your chance to own a truly special property in one of Oahu’s most desirable communities. Seller Financing Available – just 1/3 down, 5-year term starting at 6% interest-only (subject to qualification). DPP Records indicate 1,860 sq. ft. across two buildings; Buyer to conduct their own due diligence. Actual/previously earned Net Operating Income of $105,525/year. Staged photos

59-496 Pupukea Road, Haleiwa

59-450 Alapio Road Unit B1, Haleiwa
$1,925,000
4 Beds ⋅ 2 Baths ⋅ 202600508 MLS ⋅ FS - Fee Simple Tenure ⋅ 62 DOM
Welcome your private retreat in tranquil Pupukea. This 4 bed, 2 bath home is situated on .7 acres of land featuring mature lychee, guava, mango, lilikoi and banana trees. Set on a quiet, private street, the possibilities are endless - expand your estate on this lush and gated spacious property, or utilize the primary suite as a private guest quarters or rental unit. Enjoy island breezes while sitting outside on your front or back lanai! Cozy up in the evenings and look up from the front lanai - this property offers incredible opportunities to stargaze away from the lights of town! This home truly embodies comfortable island living. Iconic surf breaks, swimming coves, and some of Hawaii's most famed beaches and breaks are just a short drive down the hill. More photos coming soon!

59-450 Alapio Road Unit B1, Haleiwa

59-450 Alapio Road Unit B, Haleiwa
$1,850,000
2 Beds ⋅ 1 Baths ⋅ 202607537 MLS ⋅ FS - Fee Simple Tenure ⋅ 51 DOM
Tucked into the lush landscape of Pupukea, this charming 2-bedroom, 1-bath plantation cottage feels like a true North Shore retreat. Set on a generous 24,000 sq ft lot, the property offers space, privacy, and a slower pace of living that’s hard to find. The home has been thoughtfully renovated, blending modern touches with the warmth and character of old Hawai‘i. Natural light, simple finishes, and a comfortable layout create a space that feels easy to live in and easy to love. Step outside and you’ll find where this property really shines. Rinse off in the outdoor shower after a day at the beach, unwind in the private sauna, or simply enjoy the open space and surrounding greenery. There’s room here to grow, create, or just be. Just minutes from some of the North Shore’s best beaches and trails, this home offers an easy connection to the lifestyle that makes this side of the island so special.

59-450 Alapio Road Unit B, Haleiwa

59-414 Makana Road Unit 1, Haleiwa
$1,700,000
1 Baths ⋅ 202516470 MLS ⋅ FS - Fee Simple Tenure ⋅ 312 DOM
MUST SEE! Own 1/2 an acre of prime Pupukea real estate overlooking Sharks Cove to Pipeline! Located on the rim side of one of the most regarded streets in Pupukea, in the highly coveted subdivision of Sunset Hills. Captivating sunsets, consistent trade winds, and ocean views so close you can hear the waves crashing. Currently there is a Meditation/Yoga Studio structure that is attached to a shared septic system. There is a permit in process to turn Meditation/Yoga Studio into a single family home which will offer the possibility to expand to a 3 bedrm or more single family home. This is a newly developed CPR. Unit 2 also offered for sale- 1.5 acres for $2,950,000. Also listed as Vacant Land - See MLS 202515822

59-414 Makana Road Unit 1, Haleiwa

59-414 Makana Road Unit 1, Haleiwa
$1,700,000
202515822 MLS ⋅ FS - Fee Simple Tenure ⋅ 316 DOM
Rare opportunity to own 1/2 an acre of prime Pupukea real estate at an unbeatable price! Located on the makai side of one of the most regarded streets in Pupukea, in the highly coveted subdivision of Sunset Hills. Captivating sunsets, consistent trade winds, and ocean views so close you can hear the waves crashing. Currently there is a studio ("craft room") structure that is attached to a shared septic system. There is a permit in process to turn this craft room into a single family home which will offer the possibility to expand to a 3 bedroom single family home. This is a newly developed CPR. Unit 2 also offered for sale- 1.5 acres for $2,950,000. Also listed as Single Family - See MLS 202516470

59-414 Makana Road Unit 1, Haleiwa

59-550 Pupukea Road Unit 2, Haleiwa
$1,198,000
1 Beds ⋅ 1 Baths ⋅ 202524951 MLS ⋅ FS - Fee Simple Tenure ⋅ 28 DOM ⋅ Oahu Market BLDG.
*VA Assumable Loan Available! Discover this charming A-frame treehouse retreat nestled in the lush Pupukea hillside - just 5 minutes from world-class North Shore beaches and 10 minutes from historic Haleiwa Town. Brand new rock wall and electric gate to keep this home private and quiet from the road noise. 1 Loft - Bedroom, 2 lanai's, and a large outdoor shower zone. This unique property offers the perfect blend of island living and potential: enjoy it now as a cozy starter home or use it as a foundation to build your dream home in one of Oahu's most desirable and competitive neighborhoods. A rare opportunity to secure your place in the sought after community of Pupukea.

59-550 Pupukea Road Unit 2, Haleiwa

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.