Oprah Winfrey, one of the richest and most influential women in the world, has built a jaw-dropping portfolio of homes over the decades. From high-rise condos in Chicago to sprawling estates in California, Maui, and even Telluride, Oprah’s real estate reflects her taste for elegance, privacy, and nature.
Let’s explore Oprah’s impressive property collection — past and present — with full details, features, and hidden gems inside each home.
Oprah Winfrey Chicago Properties
1. Oprah Winfrey House In Chicago
Address: 199 East Lake Shore Drive, Chicago, IL
Oprah lived in a luxurious condo here during the peak of The Oprah Winfrey Show.
Features Inside Oprah Winfrey Condo House
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Lake Michigan views
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Marble bathrooms
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High-end kitchen
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Custom library
2. Oprah Winfrey Apartment In Four Seasons Hotel
Address: 132 East Delaware Place, Chicago, IL
This apartment combined hotel luxury with residential comfort, including room service access and high security.
3. Oprah Winfrey’s Last House In Chicago
Address: 1516 North State Parkway, Chicago, IL
Oprah sold this Gold Coast mansion in 2012. It was known for its classic architecture and private garden.
read more: celebrity house
4. Oprah Winfrey Units In Acron Lofts
Address: 1019 West Jackson Boulevard, Chicago, IL
Oprah owned multiple units in this industrial-style building, possibly for staff or guests.
Oprah Winfrey House on Fisher Island
Location: Fisher Island, Miami, Florida
A luxurious and private getaway in one of America’s most exclusive zip codes.
Oprah Winfrey Promised Land Property
1. Oprah Winfrey’s Current Home In California
Address: 1633 East Valley Road, Montecito, CA
This 70-acre estate, known as “The Promised Land,” is Oprah’s main residence.
read more: celebrity house
Amazing Features Inside Oprah Winfrey Montecito House
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23,000 sq ft mansion
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Rose gardens
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Tea house
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Wine cellar
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14 bathrooms
2. Oprah Winfrey’s Seamair Farm Addition
Address: Adjacent to her Montecito home
A 23-acre horse farm she added to expand her estate.
3. Oprah Winfrey’s House in Montecito
Property Style: Spanish Revival
Bought from actor Jeff Bridges, this house blends historic charm with modern comfort.
Hidden Features Of Winfrey’s Spanish Revival House
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Secret library room
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Hidden spa room
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Private art gallery
4. Oprah Winfrey’s Montecito House
She owns multiple homes within Montecito — used for guests, security, or private retreats.
Oprah Winfrey Hawaii Properties
1. Oprah Winfrey Maui Estate
Location: Kula, Maui, Hawaii
Oprah’s beloved upcountry ranch estate spans over 1,000 acres.
Upgradations Of Oprah Winfrey Home In Maui
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Private road
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Farm-to-table gardens
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Upgraded solar power system
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Ocean-view deck
2. Oprah Winfrey Property In Hana
Used for relaxation, surrounded by native trees and spiritual energy.
3. Oprah Winfrey Property In Kula
More of her Maui land used for sustainable farming and privacy.
Oprah Winfrey Homes In Telluride
1. Oprah Winfrey Cabin House in Telluride
Address: Mountain Village, Telluride, Colorado
A warm wooden cabin perfect for snowy getaways.
2. Oprah Winfrey Vacation Home in Telluride
High-end finishes and views of the Rocky Mountains.
3. Oprah Winfrey Temporary Home On Mountain Village
Used while developing her main Telluride property.
Impressive Features Inside Oprah Winfrey Telluride Home
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Indoor pool
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Ski-in, ski-out access
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Cozy fireplace rooms
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Glass bridge hallway
Oprah Winfrey Home In Canada
Location: Orcas Island, Washington (close to Canada)
A peaceful, waterfront retreat full of serenity.
Hidden Amenities Inside Oprah Winfrey’s Home On Orcas Island
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Yoga studio
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Zen garden
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Private dock
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Infinity pool
Oprah Winfrey Georgia Houses
1. Oprah Winfrey Penthouse In Georgia
Address: Atlanta, Georgia
A penthouse in Buckhead known for high ceilings and skyline views.
2. Oprah Winfrey Georgia Home
Used during her early career; exact details remain private.
Oprah Winfrey Other Properties
Oprah has owned other lesser-known properties for investment or short stays, including:
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A ski chalet in Idaho
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An apartment in NYC
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A residence in Montecito for her staff
Frequently Asked Questions (FAQs)
Q1: Where is Oprah Winfrey’s main residence?
A: Oprah’s main home is her “Promised Land” estate in Montecito, California.
Q2: Does Oprah Winfrey live in Hawaii?
A: She owns several properties in Maui but mainly lives in California.
Q3: How many homes does Oprah Winfrey own?
A: Oprah has owned more than a dozen homes across the U.S., including properties in California, Hawaii, Colorado, Illinois, and Georgia.
Q4: Can the public visit any of Oprah’s houses?
A: No, all her homes are private and not open to the public.
Q5: What is Oprah’s most expensive property?
A: Her Montecito estate, “The Promised Land,” is worth over $100 million.
