Issue 1147 | March 25th, 2025
Aloha ,
10 Facts About Oprah’s Palatial $60M Maui Estate
1. The value
The value $60 million is based on Winfrey’s purchases of land with inflation added. This price includes value estimates due to renovations.
So, the 2003 $5.3 million the price valuation based on inflation is now $9.5 million. Similarly, the 2021 purchase at $7 million and 2023 purchase at $6.6 million are valued at $8.2 million and $6.9 million, respectively.
This price includes value estimates due to renovations.
2. Several estates cobbled together
The palatial estate took years to amass. In 2003, Oprah bought two pieces of land on Maui that included 23.7 acres of land for $5.3 million. The land came with a small grey farmhouse that has since been turned into a beautiful vacation home.
Over time, Oprah has bought more land and at least twelve buildings in Maui. It is said that she has spent a total of $60 million on all of it.
3. Renovations
Originally, Winfrey was planning to build the “ultimate Hawaii homestead” on the land she purchased in 2003. However, instead of starting fresh, Oprah fell in love with the original house and decided to renovate it based on aesthetics she likes.
4. She relocated an entire staircase
The renovation project turned out to be much bigger than she and her architects had planned. Jeff Wooley from John B. Murray Architect changed the floor plan, took apart parts of the house, moved the staircase and added a large porch so that every room could have a view.
Although Winfrey fell in love with the home, she had to gut it. Once it was completely renovated, she said she loves it and describes it as a real, normal home that feels cozy and comforting.
5. There’s a functional/renovated bed and breakfast
One of the purchases Winfrey made included a 12-room bed and breakfast on 17 acres she renovated to house guests and wealthy customers.
While it was zoned for this purchase and renovation, there is no word if it is operating.
6. Land remains undeveloped
One of the precipitating factors that motivated Winfrey to make her first Hawaii purchase in 2003 was her attempt to save a section of Kula from being developed into condominiums.
As Winfrey continues to buy up large swaths of land on Maui, it appears that is mostly remaining undeveloped; and this had made strides amongst locals to accept Winfrey’s continued purchases of land.
7. Locals care for the land
It has been cited that Winfrey uses local workers to maintain her estates. This helps funnel money into the local economy.
8. She has a private road
Being an internationally famous super star, Winfrey has taken extra precautions to ensure her privacy by successfully acquiring the right to make the road to estate private.
9. There’s lots of animal statues
Throughout the home, Winfrey has decided to decorate with these metal animal figures. They aren’t really sculptures or pieces of art. But they do distract from the beauty of the home and the natural surroundings.
10. Gardens abound
She has chosen to cultivate several vegetable, fruit and herb gardens. The foods produced by these gardens are sold locally to help alleviate the exorbitant amount of food that has to be shipped in from places outside Hawaiʻi.
So, it seems that Oprah Winfrey is working to ensure she is integrated into the existing community on Maui as she preserves land and works to feed locals.
For more information you can click here to read more about it.
Mahalo Nui Loa,
Ken Smith R(S), Melissa Smith R(B), and Gregory P Smith R(B)
The Smith Team
P.S. Hale O Piʻikea III affordable housing on Maui is backed by $15.4M in financing.
P.S.S. If you do not agree with the assessed value or tax classification on your assessment notice, the deadline to file an appeal with the real property tax division is April 9th. https://www.mauicounty.gov/1109/Appeals.
Market Watch
|
Active |
Pending |
Sold |
Change |
Homes |
426 (372) |
126 (99) |
714 (533) |
+13 |
Condos |
843 (330) |
96 (36) |
783 (337) |
+4 |
Land |
184 (82) |
31 (11) |
159 (56) |
-3 |
Total |
1453 (784) |
253 (146) |
1656 (926) |
+14 |
1. Numbers in parentheses reflect listings over $1M
2. Sold listings are for the previous 12 months
3. Change is the increase/decrease from the previous week
January 2025
February 2025
Market Statistics
Homes Over $1M
1870 Kaahele Place
Kihei
$1.399M (FS)
|
A palm tree-lined driveway welcomes you into this secluded oasis, where indoor-outdoor living is seamlessly integrated for the ultimate island lifestyle. The single-level main home features three bedrooms and two and a half bathrooms, with a bright, open-concept design that invites natural light and a sense of spaciousness.
Customer Listing Synopsis
|
115 Kumula'au Ohia Loop
Wailuku
$1.495M (FS)
|
This exquisite home is a true gem, showcasing countless upgrades and meticulous care throughout. From the moment you step inside, you’ll notice the thoughtful enhancements, including beautiful hardwood floors, elegant crystal chandelier and pendant lighting, and Split AC in the great room and primary bedroom for year-round comfort.
Customer Listing Synopsis
Video Tour
|
18 Luanaiki Place
Kihei
$1.575M (FS)
|
This single-level, 3 bedroom, 2 bathroom home offers a perfect blend of convenience and tranquility. Situated just 1 mile from the popular Kamaole Beach Park III and located on a quiet cul-de-sac, this property promises a peaceful retreat while being close to everything you need. Step inside to an inviting open floor plan with laminate flooring throughout.
Customer Listing Synopsis
Video Tour
|
10 Meakoho Place
Kula
$1.649M (FS)
|
This exquisite property spans over half an acre, boasting two fully renovated homes with separate entrances, ensuring privacy and convenience. The main residence, features a two-car garage and a private yard, ideal for intimate gatherings or serene solitude. Every detail has been meticulously upgraded in 2022.
Customer Listing Synopsis
Video Tour
|
326 Kahana Ridge Drive
Kahana
$1.95M (FS)
|
Beautiful ocean views, with 4 bedrooms and 2 1/2 baths, 3 car garage and located in the lovely Kahana Ridge neighborhood. This stunning home in the coveted Kahana Ridge neighborhood offers an idyllic blend of comfort and breathtaking ocean views. With four bedrooms and two and a half baths, the property boasts ample space for family and guests alike.
Customer Listing Synopsis
|
69 Halelo Street
Kaanapali
$2.495M (FS)
|
This beautiful home sits on an approximately 1/3 acre landscaped lot featuring mango, lychee, longon, and ice cream bean trees. Rock walls provide privacy in this quiet sanctuary. The hot tub and swimming pool are front and center yet private, with ample room for entertaining or relaxing. Golf courses surround the neighborhood offering a green buffer.
Customer Listing Synopsis
Video Tour
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Homes Under $1M
7953 Hana Highway
Haiku
$845K (FS)
|
This absolutely astonishing oceanfront chateau located on 2 acres and at the very end of a quiet. This recently upgraded and well-maintained home boasts amazing ocean views and is equipped with top-of-the-line, off-grid living features. Enjoy a new metal roof and gutters and a reverse osmosis drinking port.
Customer Listing Synopsis
Video Tour
|
306 Kopiko Street
Wailuku
$895K (FS)
|
Ocean view from kitchen and back bedroom. Iao Valley mountain view from living room and front bedroom. The downstairs has a separate living room area that has been used in the past as another bedroom which would bring the total house bedrooms to 5. There is a connecting internal stairwell that can be locked to keep the downstairs and upstairs living areas separate.
Customer Listing Synopsis
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293 Manini Place
Kihei
$925K (FS)
|
This single-level, 2 bedroom, 1.5 bath home is built with durable CMU block construction, providing easy maintenance, a clean aesthetic and a solid foundation. The existing floor plan allows for an easy addition of a third bedroom, with plenty of potential for future expansion, including an ohana.
Customer Listing Synopsis
|
Vacation Condos Over $1M
Papakea Resort G-407
Honokowai
$1.075M (FS)
|
The perfect place for a family vacation or a romantic escape. From your 4th floor lanai, you have 180-degree, beautiful views of the ocean, shuffleboard court, pool/Jacuzzi/barbecue area, putting green, tropical gardens, koi ponds, and the West Maui Mountains.
Customer Listing Synopsis
Video Tour
|
Wailea Ekolu 1705
Wailea
$1.5M (FS)
|
This modern single level 2 bedroom, 2 bath ground floor residence. Open-concept design with luxury gray vinyl plank flooring throughout. Stylish interior with remodeled features like beautiful white cabinets, stainless steel appliances, and quartz counter tops.
Customer Listing Synopsis
Video Tour
|
Wailea Elua 708
Wailea
$3.75M (FS)
|
Stunning 2 bedroom, 2 bathroom top-floor condo with breathtaking ocean views. Located in the highly sought-after Wailea Resort, this fully furnished vacation rental unit features high vaulted ceilings, recessed lighting, and two separate lanais to enjoy Maui's incredible sunsets.
Customer Listing Synopsis
Video Tour
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Wailea Beach Villas J-106
Wailea
$4.395M (FS)
|
Stylishly furnished and turnkey, this villa offers central A/C for year-round comfort. The primary suite is a palatial retreat, boasting a spacious sitting area, an opulent walk-in closet, and a spa-inspired en-suite with a soaking tub, separate shower, and gleaming quartz countertops. A beautifully appointed guest bedroom ensures comfort.
Customer Listing Synopsis
Video Tour
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Vacation Condos Under $1M
Paki Maui 320
Honokowai
$458.7K (FS)
|
This is your opportunity to own this lovely unit that shows like a gem and over looks the courtyard of lush gardens where you can enjoy your morning coffee while listening to the tranquil background of the cascading water fall into the koi pond.
Customer Listing Synopsis
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Kalama Terrace L-204
Kihei
$475K (FS)
|
This charming 1 bedroom, 1 bath unit. This condo features a newer gas stove and refrigerator, along with granite counters in the kitchen and updated wood cabinets, tiled shower walls, and tiled floors throughout. Enjoy the view of the peaceful grounds from your covered lanai area. Unit comes fully furnished.
Customer Listing Synopsis
|
Royal Kahana 213
Kahana
$675K (FS)
|
This stunning residence boasts sweeping ocean views from the moment you step through the door, making it the perfect vantage point for whale watching, people watching at the pool, and enjoying vibrant sunsets. Recently remodeled in 2021, this condo features contemporary upgrades throughout.
Customer Listing Synopsis
|
Residential Condos Over $1M
Kai Ani Village 3-109
Kihei
$1.199M (FS)
|
This rare work/live opportunity boasts a two-car garage and is designed to cater to both your residential and business needs. The ground floor is fully ADA accessible and offers an ideal space for your business or generate rental income from a commercial tenant. This 500 Sq Ft commercial space features air conditioning for year-round comfort.
Customer Listing Synopsis
Video Tour
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Masters 2603
Kaanapali
$1.7M (FS)
|
Experience breathtaking panoramic views of the Pacific Ocean and the Islands of Lanai and Molokai from nearly every room in this beautifully remodeled 2 bedroom, 2 bathroom suite at The Masters. Thoughtfully upgraded in 2014.
Customer Listing Synopsis
Video Tour
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Residential Condos Under $1M
Puuone Towers and Plaza 308
Wailuku
$399K (FS)
|
This 6-story high-rise building is located in the heart of Wailuku, and super convenient to Central Maui's main shopping district, hospital, government services, UH Maui, Maui Arts and Cultural Center, and downtown Wailuku's eclectic shops and dining options can't be missed! Unit comes partially furnished to help you get started to your new "city life" in Maui.
Customer Listing Synopsis
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Keonekai Villages 9-202
Kihei
$549.8K (FS)
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This upgraded 2 bedroom, 1.5 bath upstairs condo is nestled in the highly desirable Keonekai Villages complex, just a few blocks from the golden sands of Kamaole Beach Park III. Offering breathtaking views of Haleakala from your private lanai, this home captures the essence of Maui living.
Customer Listing Synopsis
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Kahului Ikena 327
Kahului
$525K (FS)
|
This charming 2 bedroom, 2 bathroom condo offers the perfect blend of convenience and tranquility. Located on the second floor, Unit boasts an open and airy layout, designed to maximize natural light and ocean breezes. Enjoy modern comforts with a spacious kitchen, inviting living area, and two well-appointed bedrooms, each offering privacy and relaxation.
Customer Listing Synopsis
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Keonekai Villages 9-102
Kihei
$599.8K (FS)
|
Welcome to this beautifully remodeled 2 bedroom, 1.5 bath ground-floor condo with a large yard, in the highly desirable Keonekai Villages in South Maui. Just one block from Kamaole Beach Park III, you’ll enjoy easy access to golden sand, turquoise waters, and breathtaking sunsets.
Customer Listing Synopsis
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Haleakala Gardens 3-E
Kihei
$650K (FS)
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Step into this bright and inviting second-floor end unit, where comfort and convenience come together in the heart of Kihei. With 3 spacious bedrooms and 2 beautifully upgraded bathrooms, this home is perfect for relaxing and making memories. Located near the new Kihei High School, it’s a treasure in a sought-after neighborhood.
Customer Listing Synopsis
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Vacant Land
511 Kualau Street
Wailuku
$599K (FS)
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Make building your dream home a reality. This is a rare opportunity to own one of the remaining vacant lots, nestled in the prestigious area of Wailuku Heights I. Begin and end your day with tranquil views of Haleakala, the North Shore and the majestic West Maui Mountains.
Customer Listing Synopsis
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