Winfrey spent around $5.3 million on two properties in Maui that combined for 163 acres. She had no additional Chicago properties after it was ultimately sold in 2018 for $375,000. The 2,250-square-foot house was mostly kept in its original condition by the television star, who invested some money in replacing the roof and gutters, the garage door, and the heating and conditioning system. Winfrey spent $298,000 on a much smaller four-bedroom Colonial-style house in the Elmwood Park neighbourhood, just outside of Chicago, that same year. Winfrey still refers to this large estate as her primary residence and has continued to acquire surrounding properties over the years to increase her Montecito holdings.

The initial 42-acre property cost the media magnate roughly $50 million, and it had a 23,000-square-foot Georgian-style home, a 6,000-square-foot redwood guesthouse, and an outside space ideal for a pool, tennis court, and numerous patios. In 2001, Winfrey started putting down roots in her expansive property in Montecito, which has come to be known as the Promised Land. In the end, Winfrey sold the property to the former chairman of Campbell’s Soup for a then-unprecedented $6.5 million. With a wood-burning oven in the kitchen and a roomy master suite with his-and-hers en suite baths and dressing rooms, the house itself was airy and well-lit. The apartment was in the upscale Villa Del Mare condos, which had a billiards club, a bicycle trail, numerous swimming pools, and a spa as facilities. She spent an undisclosed sum on a 6,170 square foot penthouse property with four bedrooms, six bathrooms, 20-foot ceilings, and a sizable oceanfront balcony. On Fisher Island, a 216-acre man-made island located just off the coast of Miami, Winfrey made a much-discussed acquisition this year. The property was subsequently sold by Winfrey for $1.275 million in 2015, the same year the studios were permanently closed and she moved to the West Coast. The famed luxury hotel is not far from the Near West Side, where Winfrey’s multimedia production firm at the time, Harpo Studios, is located, and a few steps from Lake Michigan. Winfrey spent $100,000 on a three-bedroom condominium at the Four Seasons Chicago at about the same time she bought the final of the four adjacent condos at Water Tower Place.

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