Oprah Gail Winfrey, an American TV host, producer, actress, author, and business owner who gained enough popularity to host her own talk show, The Oprah Winfrey Show, now possesses a whopping net worth of $3 billion. With a successful career, she has built a really strong real estate portfolio worth $150 million. Oprah Winfrey House in Montecito, California, has captured the attention of many people due to its impressive features.
Today, we’ll explore all the Oprah Winfrey Houses that she has purchased and lived in during her career. We’ll also briefly discuss their stunning amenities and architectural features inside.
Oprah Winfrey Chicago Properties
Winfrey purchased four condos in Chicago’s Water Tower Place, an apartment over the Four Seasons Hotel, and a house in Elmwood Park.
1. Oprah Winfrey House In Chicago
Address: 180 E Pearson St, Chicago, IL 60611, United States
Style: Condo
Area: 9,625 Square feet
Price: $4.63 million
Just a year before Oprah Winfrey started her career in Chicago, Illinois, hosting a local talk show named The Oprah Winfrey Show in September 1986, she bought her first condo, unit 5703. This condo was in Chicago’s Water Tower Place, which she purchased for an undisclosed amount.
Over time, she purchased three more condos nearby in the same building. She bought unit 5603 for $1.0625 million in 1992, unit 5602 for $1.5 million in 1993, and unit 5601 for $1 million in 1994. Then, she combined them into one huge home covering an area of 9,625 square feet. After the show ended in 2011, she listed her home for sale in 2014 for $7.75 million. However, it was sold for $4.63 million in 2015 with a big loss.
Features Inside Oprah Winfrey Condo House
Oprah Winfrey’s Condo on the 56th-floor features five bedrooms, five full and two half bathrooms, two gourmet kitchens, a library, a living room, and a gym. The master bedroom is especially luxurious and is decorated with fancy finishes and fabrics. The large windows let in enough sunlight and stunning city views.
Both kitchens offer top-notch appliances, customized cabinets, and enough space for cooking. The condo offers plenty of storage and lots of living space. Moreover, the building also offers many amenities like room service, valet parking, gyms, restaurants, and spas.
2. Oprah Winfrey Apartment In Four Seasons Hotel
Address: 120 E Delaware Pl, Chicago, IL 60611, United States
Style: Condo
Price: $100,000
In 1994, Oprah purchased another Condo over the Four Seasons Hotel in Chicago. She paid $100,000 for the apartment, which had three bedrooms and a great view of Lake Michigan. Oprah used this condo as a convenient place to stay near her talk show’s studios. After moving to California, she sold this apartment in 2015 for $1.275 million, with a massive profit of over $1 million.
3. Oprah Winfrey’s Last House In Chicago
Address: 1705 N 78th Ct, Elmwood Park, IL 60707, United States
Style: Colonial Style House
Area: 2,250 Square feet
Price: $298,000
In 2001, Oprah purchased her last Chicago house on Elmwood Park for $298,000. This 1941-built-in house offers a living area of just 2,250 square feet. This small house features four bedrooms, two bathrooms, a kitchen, a family room, a living room, a dining room, a basement, and a one-car garage.
She spent some amount on this house’s renovations, like updating the heating system, gutters, and roof. This last Oprah Winfrey House in Chicago was sold for $375,000 in 2018 after listing it in the same year. However, she never lived in this house.
4. Oprah Winfrey Units In Acron Lofts
Address: 1017 W Washington BlvdChicago, IL 60607, United States
Price: $2,057,000
Winfrey once owned three units in a building called Acron Lofts, located at 1017 W Washington Blvd, Chicago, which she purchased in the 2000s. However, she sold all three of them at a big loss. She sold one for $675,000, one for $507,000, and the third for $875,000, which she bought for $1.98 million.
Oprah Winfrey House on Fisher Island
Address: 7193 Fisher Island Dr, Miami Beach, FL 33109, United States
Style: Penthouse
Area: 6,170 Square feet
Price: $6.5 million
Just after purchasing an apartment over the Four Seasons Hotel in Illinois, the legendary TV host purchased another big penthouse apartment in 1995 on a private island in Miami, Florida. She used to spend winters on Fisher Island and stayed there for a long time.
Oprah Winfrey house on Fisher Island features stunning ocean views. This penthouse offers over 6,000 square feet of living area featuring four bedrooms, six bathrooms, a modern kitchen, a living room, a formal family room, a big oceanfront balcony, and other luxurious features. It had 20-foot ceilings, large windows offering beautiful outdoor views, and comfortable furniture elements. Oprah sold this apartment to a rich businessman named David Johnson in 2001 for $6.5 million.
Oprah Winfrey Promised Land Property
Oprah bought three properties in Montecito from 2001 to 2019 to build her dream home, which she named The Land Property.
1. Oprah Winfrey’s Current Home In California
Address: 120 Santa Rosa Ln, Montecito, CA 93108, United States
Style: Georgian Style House
Area: 42 acres
Price: $52 million
In 2001, the Presidential Medal of Freedom award winner purchased a massive property, also known as The Promised Land, in Montecito, California. She paid $50 million for this 42-acre estate.
Oprah still owns this luxurious house and uses it as her current residence and for interviews. This mansion features great views of the mountains and ocean. Over time, she bought more land and buildings to turn this place into almost 70 acres. Today, Oprah Winfrey’s current house is worth over $100 million, making it one of the most expensive homes in the area.
Amazing Features Inside Oprah Winfrey Montecito House
Oprah Winfrey house in Montecito features a 6,000 square feet guesthouse and a main house offering 23,000 square feet of living area. The main house features six bedrooms, fourteen bathrooms, several living and dining rooms, a formal family room, a modern kitchen, two home theaters, a library, a wine cellar, a gym, a spa, an office, and ten fireplaces.
The massive outdoor area features an infinity pool, a pool house, stables, a tennis court, multiple terraced gardens for interviews and relaxation, a fruit orchard, a horse riding area, and a peaceful garden that Oprah loves to relax in. There’s also a kitchen with a grill and a comfortable seating area to arrange barbeque parties. The exterior of Oprah Winfrey’s current home features slightly steep roofs, chimneys, and large windows offering stunning natural views.
2. Oprah Winfrey’s Seamair Farm Addition
Address: 380 Santa Rosa Ln, Santa Barbara, CA 93108, United States
Style: Ranch House
Area: 23 acres
Price: $28.8 million
In 2015, Oprah planned to expand her Promised Land on the sunny West Coast by buying the adjacent Seamair Farm for $28.8 million. This ranch offers only 4,755 square feet of living area on a massive 23 acres of land. The property offers stunning views of the Pacific Ocean and Santa Ynez Mountains.
This 1952 built-in luxurious ranch offers all the amenities like a large backyard, pool, and patio. The main house was designed by Cliff May. The estate features grazing fields, a circular paddock, stables, horse tracks, fish ponds, fruit orchards, pens, stalls, and private wells.
Shortly after, Oprah also bought a neighboring 44-acre property, where she grows her own fruits and vegetables.
3. Oprah Winfrey’s House in Montecito
Address: 1690 San Leandro Ln, Montecito, CA 93108, United States
Style: Spanish Revival Style House
Area: 4 acres
Price: $6.85 million
In 2019, Oprah Winfrey bought a Spanish Revival-style compound in Montecito from actor Jeff Bridges and his wife for nearly $6.85 million. This four-acre property features a living structure of 3,517 square feet.
This purchase brings Oprah’s total Montecito property to 70 acres. This Oprah Winfrey house back in 2017 was badly affected by mudslides, however, the Bridges restored the estate before selling it to Oprah.
Hidden Features Of Winfrey’s Spanish Revival House
This 1919-built-in house features three bedrooms, two bathrooms, a luxurious living room, a dining room, a chef’s kitchen, a media room, a gym, a central courtyard, and a spacious family room. The massive outdoor area features a swimming pool, a private well, a pool house with a family room, gardens, a 5,000-square-foot barn, and a separate one-bedroom guesthouse.
The interior features hardwood floors, exposed wooden beams, large windows, pendant lights, five fireplaces, comfortable furniture, high ceilings, and French doors. The master suite features a bay window, a beamed ceiling, a cozy fireplace, French doors, and enough space for relaxation. The kitchen is equipped with high-end appliances, wooden cabinets, and quartz countertops and connects to a spacious family room.
4. Oprah Winfrey’s Montecito House
Address: 990 Hot Springs Rd, Montecito, CA 93108, United States
Style: Tuscan Style House
Area: 2 acres
Price: $10.5 million
In 2021, Oprah bought another luxurious property in Montecito for $10.5 million. This 1999-built-in house features a main house and two cottages. This Tuscan-style farmhouse offers stunning features like a home theater, wine cellar, gym, spa, office, library, games room, and panoramic ocean views.
After just 18 months, Oprah sold the main residence to famous American actress Jennifer Aniston for nearly $14.8 million in an off-market deal in August 2022. The two cottages were sold to Oprah’s personal trainer Bob Greene for $2.3 million, making a staggering profit of $6.5 million.
Oprah Winfrey Hawaii Properties
Oprah owns more than 1,000 acres of land on Maui, Hawaii, that she uses for vacation.
1. Oprah Winfrey Maui Estate
Address: Thompson Road, Upcountry, Maui, Hawaii, United States
Style: Ranch Style House
Area: 166 acres
Price: $40 million
Oprah’s trainer, Bob Greene, convinced Oprah to buy land in Maui, Hawaii. She started buying the land in Maui in 2002. She bought her first 2-acre property in February for $2.95 million, a 102-acre property in July for $11.68 million, and a small property in October for $200,000. Overall, she bought three properties on Maui totaling over 117 acres for $17 million in 2022.
In 2023, she again bought three more properties on Maui, covering about 49 acres, for over $8 million. Her first one was a 9-acre property for $3.2 million, a 33.79-acre property for $2.875 million, and a 6.333-acre property for $2.1 million. One property had a ranch there.
Upgradations Of Oprah Winfrey Home In Maui
With the help of decorator Ellie Cullman and Architect Jeff Wooley, she turned the place into a beautiful island farmhouse, including a main house and a guesthouse. The project started small but became a big renovation. They added a porch and a spa, changed the floor plan, and upgraded the kitchen. They used country-style decorations and bright colors to make it feel fresh and welcoming.
She uses her luxury bed-and-breakfast to accommodate guests who visit her when she’s staying there. She has also built a secret road inside that connects to multiple areas of the estate, which she offered to the locals for evacuation when big fires hit Maui in 2019.
Over time, she has spent around $40 million on the Muai estate, and now, this property is known as Oprah Winfrey’s vacation home.
2. Oprah Winfrey Property In Hana
Address: Hana, Maui, Hawaii, United States
Style: Piece of Land
Area: 200 acres
Price: Unknown
From 2005 till now, Winfrey has purchased over 200 acres of coastal land in Hāna, Maui. However, Oprah hasn’t commented regarding the purpose of the land yet.
3. Oprah Winfrey Property In Kula
Address: Kula, Maui, Hawaii, United States
Style: Piece of Land
Area: 870 acres
Price: $6.6 million
In March 2023, the real estate mogul purchased about 870 acres of land in Kula, Maui, for $6.6 million. She bought this massive land in four purchases. She paid $3.89 million for 520 acres, $2.47 million for 330 acres, and $100,000 each for two smaller 10-acre pieces. After this massive property purchase, she now owns about 1,000 acres on the island.
Oprah Winfrey Homes In Telluride
The TV mogul has purchased three properties in Telluride since 1994.
1. Oprah Winfrey Cabin House in Telluride
Address: Ski Town Telluride, Colorado, United States
Style: Cabin House
Area: Unknown
Price: Unknown
In August 1994, Oprah bought a cabin in Telluride, Colorado, for an undisclosed amount. This cabin featured hardwood floors, wooden ceilings, and rustic furniture elements inside. The corridor and the outdoor area offer beautiful views of nature and the San Juan mountains.
2. Oprah Winfrey Vacation Home in Telluride
Address: Mountain Village, Telluride, CO 81435, United States
Style: Cabin House
Area: 34,000 Square feet
Price: $10.85 million
In March 2014, Oprah bought almost 60 acres of land near a ski resort in Mountain Village for $10.85 million from Carol Barnett and her husband, Hoyt Barnett. To make her dream home here, she started construction on this property. During the construction at the site, Oprah wanted a place to stay in Telluride. So, she bought a high-tech mansion there for $13.7 million as a temporary home in the following year.
A neighbor, a retired physicist, sued her over access to hiking trails. However, the lawsuit was dropped later. After finishing the construction, this Oprah Winfrey house offers breathtaking views of nature and mountains. Some of its cool features are a movie theater, a special trail for skiing, and a big wine cellar.
3. Oprah Winfrey Temporary Home On Mountain Village
Address: 184 Butch Cassidy Drive, Mountain Village, CO 81435, United States
Style: Contemporary Cabin House
Area: 8,706 Square feet
Price: $13.7 million
When Oprah’s Telluride home was being built, she purchased a Mountain Village house from a tech entrepreneur for $13.7 million. Another reason for buying this property was that she was having a dispute with her retired physicist at her other property, but the problem was eventually solved.
Oprah didn’t stay here for long and sold this stunning home for $17 million in October 2021 in a profitable deal.
Impressive Features Inside Oprah Winfrey Telluride Home
This luxurious home of Oprah Winfrey features five bedrooms, seven bathrooms, a living room, a formal dining area, a gourmet kitchen with a wood-burning pizza oven, a home gym, and a games room. Other cool features include a state-of-the-art movie theater, a 56-foot-long underground 1,600-bottle wine mine cellar, enclosed walkways, a built-in ski-in, and a ski-out trail leading to the nearby skiing trails.
This modern home is located in a private area with direct access to hiking trails offering stunning views of the San Sophia Range. The house is made of glass, steel, and natural construction materials like wood and stone. Its unique house design blends perfectly with the natural surroundings. The enclosed walkway leads to a tree-top deck with a fire pit. A funicular connects to a hiking trail. There’s also a glass and steel bridge over the great room.
Oprah Winfrey Home In Canada
Address: 512 Catspaw Ln, Olga, WA 98279, Canada
Area: 40.98 acres
Price: $8.275 million
In May 2018, Oprah fell in love with the San Juan Islands during a Pacific Northwest vacation and soon purchased a massive almost 41-acre property for $8.275 million. Oprah named this waterfront property Madroneagle. This property offers a 7,303-square-foot home that features 3,000 feet of waterfront and a large, south-facing beach on East Sound
Oprah didn’t have enough time to enjoy the getaway. Therefore, she sold Madroneagle in July 2021 for $14 million and made a significant profit.
Hidden Amenities Inside Oprah Winfrey’s Home On Orcas Island
This impressive property features four bedrooms, four bathrooms, a massive living room, a formal dining area, a gourmet kitchen, a spacious entertainment room, a large library, a wine cellar, and an office. The estate also includes a spa, docks, a sauna, an Asian-style garden, a pond, a shop, a stream, trails, and a private beach.
The interior of Oprah Winfrey’s vacation home is finished with extraordinary attention to detail, featuring radiant heated floors, stone fireplaces, reclaimed local wood, and custom ironwork. The exterior boasts a copper and slate roof, large windows, and natural construction materials like wood and stone. The chef’s kitchen is equipped with a wood-fired pizza oven and premier appliances.
Oprah Winfrey Georgia Houses
The billionaire TV host was also the proud owner of two stunning Georgian houses
1. Oprah Winfrey Penthouse In Georgia
Address: Atlanta, Georgia, United States
Area: 4,806 Square feet
Price: $1.515 million
Oprah purchased a 39th-floor penthouse apartment in Atlanta in 2003 for $1,515,000. It is not clear if she ever lived there. However, after three years, she sold this apartment with a small profit of $1.8 million in 2008.
2. Oprah Winfrey Georgia Home
Address: 4555 Stratford Dr, Douglasville, GA 30135, United States
Area: 1.26 acres
Price: $825,000
Oprah purchased a Georgian house in 2005 for $825,000 in Douglasville, GA. This 8,082 square foot home features eight bedrooms, eight bathrooms, a living room with a dining area, a kitchen, a family room, and other living spaces. This house features plush gardens, large windows, and large columns supporting the entrance. Oprah didn’t live there much and gifted this home to someone.
Oprah Winfrey Other Properties
Apart from these properties, Oprah Winfrey owns many other properties, too. These include a 164-acre Indiana farm that she purchased in the 1990s and a house in northwest Indiana. The farm features a main house, a guest house, a pool house, and many other stunning amenities. She sold it in 2004 for $6.9 million.
She purchased a condo in suburban Milwaukee for $399,000 in 1998 that her mother uses and a near-west suburban house that she purchased for $240,000 in 2001. She also bought a lakefront condo in Milwaukee in 2019 for $448,900, a house in Tennessee, which she bought in 2020 for her father for almost $1.52 million, and some other properties in Tennessee.
Frequently Asked Questions (FAQs)
Where Is Oprah Winfrey House?
Oprah Winfrey’s main home is in Montecito, California. However, she also owns properties in Hawaii, Telluride, Indiana, Tennessee, and Milwaukee.
Does Oprah Live In Chicago?
During the shooting of the Oprah Winfrey Show from 1986 to 2011, she lived some time. She bought condos in Chicago’s Water Tower Place, Four Season Hotel, and Acron Lofts and a house in Elmwood Park.
How Much Is Oprah’s House In Montecito?
Oprah Winfrey’s main home, also known as The Promised Land, is in Montecito, California, and is valued at over $100 million. She bought it in 2001 for around $52 million.
Did Jennifer Aniston Buy Oprah Winfrey’s House?
Jennifer Aniston bought Oprah Winfrey’s Montecito home located at 990 Hot Springs Rd for nearly $14.8 million in an off-market deal in August 2022.
How Many Houses Does Oprah Winfrey Own?
Oprah Winfrey owns multiple properties, including homes in Montecito, Hawaii, Tennessee, Telluride, Indiana, and Milwaukee.