Start Living Your Best Life by the Sea! This expansive beachfront compound runs from street to ocean and offers nearly 29,000 square feet of sprawling tropical grounds, beautiful mature trees, and a tranquil sandy beachfront setting. Wake to panoramic seaside vistas by day and relax to mesmerizing sunsets by night. This multi dwelling compound offers a main residence complete with five bedrooms and a large open floor plan with vaulted ceilings and mesmerizing views of the Pacific Ocean, where one can enjoy every imaginable water sport right at your back door. Surfing, SUP boarding, kayaking, kite surfing, snorkeling & more are all part of a day in the life of this special island compound. The detached cottages provide additional space and separation and are ideal for extended family use, home offices, yoga studio, home gym & more. A sizable, tiled swimming pool with wraparound sun deck provides the perfect place for weekend fun and relaxation. If you are looking for the ultimate private retreat with an abundance of open space on one of Oahu’s most beautiful sandy shorelines; then grab your surfboard and welcome home! This is Beach Life!
Wailupe Beach is a luxury oceanfront neighborhood of about 2 dozen beachfront homes along Kalanianaole Hwy plus about 120 homes within the Wailupe Peninsula. The Wailupe Beach neighborhood is bordered by Kai Nani to the west and Aina Haina Beach to the east.
Most Wailupe Beach homes for sale are priced between $1.2M to $5M with lot sizes between 6,000 to 30,000 sq ft. Coveted Wailupe Peninsula homes for sale are priced in the $1.3M to $8M range with typical lot sizes between 11,000 to 18,000 sq ft.
The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on January 31, 2026.Information is deemed reliable but not guaranteed.
Sold 10/20/21 at $6,500,000 (List Price: $5,895,000)
Description
Start Living Your Best Life by the Sea! This expansive beachfront compound runs from street to ocean and offers nearly 29,000 square feet of sprawling tropical grounds, beautiful mature trees, and a tranquil sandy beachfront setting. Wake to panoramic seaside vistas by day and relax to mesmerizing sunsets by night. This multi dwelling compound offers a main residence complete with five bedrooms and a large open floor plan with vaulted ceilings and mesmerizing views of the Pacific Ocean, where one can enjoy every imaginable water sport right at your back door. Surfing, SUP boarding, kayaking, kite surfing, snorkeling & more are all part of a day in the life of this special island compound. The detached cottages provide additional space and separation and are ideal for extended family use, home offices, yoga studio, home gym & more. A sizable, tiled swimming pool with wraparound sun deck provides the perfect place for weekend fun and relaxation. If you are looking for the ultimate private retreat with an abundance of open space on one of Oahu’s most beautiful sandy shorelines; then grab your surfboard and welcome home! This is Beach Life!
The MLS properties are based on information from the Multiple Listing Service of Hicentral MLS, Ltd. Listings last updated on January 31, 2026.Information is deemed reliable but not guaranteed.
Wailupe Beach is a luxury oceanfront neighborhood of about 2 dozen beachfront homes along Kalanianaole Hwy plus about 120 homes within the Wailupe Peninsula. The Wailupe Beach neighborhood is bordered by Kai Nani to the west and Aina Haina Beach to the east.
Most Wailupe Beach homes for sale are priced between $1.2M to $5M with lot sizes between 6,000 to 30,000 sq ft. Coveted Wailupe Peninsula homes for sale are priced in the $1.3M to $8M range with typical lot sizes between 11,000 to 18,000 sq ft.
You do not own the land, but have the right to use the land until an expiration year. At expiration the ownership typically reverts back to the land owner.
Buyer and Seller have reached an agreement and are under contract. The sale may be subject to one or more contingencies.
We have handled many transactions for clients who purchase Hawaii real estate without visiting. By request, we can prepare thorough property videos to ensure you are familiar with every detail necessary. All documents can be signed remotely.
Buyer and Seller have reached an agreement and are under contract. The sale is expected to close / record soon.
We will be happy to work with you as a Buyer's agent. Call us to learn more: 808-943-9000. Note: A Seller's agent has a fiduciary responsibility towards the Seller. Working with a Buyer's agent objectives and goals are aligned, at no cost to you, the Buyer.
Other fees could be a special assessment, reserve contributions etc.
DOM = Days On Market. Our site shows listings immediately. A brand new listing may show DOM 2 or 3 days, if listing agent did not upload the same day listing agreement was executed.
Includes estimated monthly mortgage payment, maintenance / HOA fees & property taxes. The estimate does not include insurance premiums.
"....ensuring you have all the facts...." It’s with immense pleasure that I share my experience with Tracy, a realtor who I wholeheartedly endorse for anyone navigating the O‘ahu real estate market. From day one, communication with Tracy was refreshingly easy. He listens intently, articulates his points clearly, and ensures that every question is answered with precision.
Tracy’s expertise in the local property market is unparalleled. He has a vast network of contacts that proves invaluable in every transaction. It’s not just about having a realtor with knowledge; it’s about having one who can harness that knowledge to connect you with the right people and opportunities.
Over the course of our four-year acquaintance, Tracy has patiently worked to understand our specific needs. For my wife and me, relocating from Texas meant finding a home that wasn't just a space to live, but a place that resonated with our lifestyle and aspirations. Tracy’s approach to real estate goes beyond the transactional aspect; he has an intuitive grasp of what makes a house a home for his clients.
He has been an anchor, offering candid and practical advice. His straightforward feedback has been crucial in helping us discern the best choices for us amidst a sea of possibilities. Navigating the technicalities of real estate can be daunting, but Tracy provided us with the guidance and support needed to understand the finer points, ensuring we made well-informed decisions.
Our professional relationship with Tracy has evolved into a cherished friendship. His integrity and dedication are evident in his every action. He's a realtor who gives you the unvarnished truth, ensuring you have all the facts to make decisions that are right for you.
As our long and sometimes challenging journey to find the perfect home comes to a close, we reflect on the path we’ve traveled with gratitude. Tracy has been more than a realtor; he has been a trusted advisor, a confidant, and a friend. We’re profoundly grateful for his relentless dedication to our cause.
Mahalo, Tracy, for your exceptional service and for being an integral part of our life-changing adventure to find our dream home in the beautiful state of Hawai‘i. I highly recommend. Naoto Ueno - Home Buyer, Kakaako
"....full of knowledge...." We finally did it!!!! We worked with Tracey Yamato at Hawaii Living to get through one of the most confusing processes I've ever been a part of... WOW! Thank goodness for Tracey! Buying a home has been a dream but the actual process is WAY more involved than you might imagine. It can takes months of scouring properties before finding the home you love and only then does the real work begin. Deadlines, paperwork, inspections, contractors to schedule, do's, don'ts etc. etc. etc... it was crazy. There is so much to know and so much paperwork to understand we truly couldn't have done this without Tracey by our side. It is legitimately a full time job to handle all of the deadlines and inspections and there is just no way my partner and I could have kept up with our actual jobs while also managing all of this. Thank goodness Tracey was there every step of the way and so full of knowledge about every little thing that we could have possibly needed to know about. Thank you Tracey for all you did
