Oprah Winfrey’s Hawaiian Homestead

I recently came across Oprah’s Hawaiian Home on Oprah.com and had to share this beautiful creation with you. Oprah’s personal trainer, Bob Green, found the homes gorgeous property a couple of years ago after a 15 year search through Hawaii for the “perfect spot”. The house is located in a remote up-country region on a moss covered hillside facing the ocean.

To own something even remotely close to that kind of paradise, you need more than just good taste—you need solid financial footing. Dream homes like Oprah’s don’t come cheap, and sometimes, reaching that next stage requires freeing up funds quickly. Maybe you’ve got an inherited property sitting unused, quietly gathering dust instead of value. If that’s the case, you might want to click here to explore how turning that idle asset into quick cash could bring you closer to building or buying the kind of home that truly reflects your vision of comfort and success.

With the right approach, selling an unused or inherited home isn’t just about letting go—it’s about moving forward with purpose. That cash infusion can open doors to new opportunities, whether that’s designing a home from the ground up, investing in land, or simply creating a more secure financial cushion. After all, luxury isn’t always about the size or location of a house—it’s about having the freedom to choose the life you want to build within it.

Opera Winfrey Hawaiian Home

What was originally supposed to be a quick remodel quickly turned into the ultimate Hawaiin Homestead. Oprah flew to Hawaii with her decorator Ellie Cullman and thus began the creation of this beautiful home.The house was stripped to its basic structure, the staircase moved, ceilings were raised, new French doors installed throughout, and a gorgeous veranda was wrapped around the whole house.

Opera Winfrey Hawaii Porch View

The wraparound porch looks as if it’s been there forever. The pretty outdoor furniture is from Weatherend.

Opera Winfrey Hawaii View From Master Bedroom

Opera can step directly from her bedroom into the veranda to enjoy the breathtaking view.

Opera Winfrey Hawaii Kitchen

The ceiling design in the kitchen was inspired by an old quilt.

Opera Winfrey Hawaii Living Room

The horses on the hills surrounding the ranch motivated the theme for the living room. A late-19th-century American weather vane in the shape of a galloping horse, spotted on one of Oprah and Ellie’s shopping trips, became the centerpiece of the room.

Opera Winfrey Hawaii Dining Room

The table in the dining room was brought in from an old pool  house. The chair coverings and bright walls make the room a cheerful environment.

Everywhere you look throughout the house is something of interest and quality. It invokes memories of Oprah’s rural American past.

(All photos courtesy of Oprah.com)

ZoeR

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