Oprah's Ever-Increasing Hawaiian Holdings

Former chat show queen turned struggling tee-vee network owner Oprah Winfrey may be downsizing her property portfolio in her long-time home base of Chicago, IL but according to The Bizzy Boys at Celebrity Address Aerial (and some additional research into the property records by Your Mama) the big-livin' billionairess continues to spend boo-coo bucks enlarging her somewhat remote ranch near the community of Kula on the Hawaiian island of Maui.

As best as we can surmise from public property records, Miz Winfrey's ever-expanding Hawaiian hideaway currently encompasses at least 31 parcels that combined span just over 782 acres. Most of the the various parcels are contiguous although some key pieces remain missing from the middle of her property puzzle and Your Mama would fall off our inflatable donut with shock if over the next few years she didn't drop a substantial wad of dough to snatch those up too.

Although some of the property records are a mite confusing, Miz Winfrey has, buy our rudimentary and unscientific calculations, spent at least $44,000,000 and perhaps more than $60,000,000 on the various properties that altogether have at least a dozen homes and scores of outbuildings and farm-related structures. She's had at least one of the many houses on her ranch photographed for her magazine.

Property records indicate Miz Winfrey first starting buying up property on Maui in October of 2003 when she shelled out $5,300,000 to purchase a pair of adjacent parcels that combined span 23.7 acres and include a recently re-built compound with an 8,838 square foot main mansion plus at least 3 additional structures.

Over the last nearly 10 years Miz Winfrey has steadily bought up dozens of surrounding properties. Some of her most recent acquisitions came in March 2011 when she snapped up three vacant parcels that combined measure 24.5 acres and cost $3,300,000. At just about the same time she picked up a 12.57 acre spread with a 4,253 square foot house (plus equestrian facilities) for $4,400,000 and just about a month later she dropped another $4,500,000 on a 6.87 acre spread with a couple of modestly-sized residences.

Most of Miz Winfrey's Hawaiian holdings are contiguous but there remain a healthy handful of key properties missing in the center of her real estate puzzle that Your Mama would be shocked if she doesn't purchase in the the not so distant future.

After years in Chicago (IL) where her eponymous and insanely influential talk show taped, Miz Winfrey now makes her primary home at The Promised Land, a 42-acre, fully-landscaped estate in Montecito, CA with a 23,000(ish) square foot mansion, numerous outbuildings and a distant, sparkling view of the Pacific Ocean. She paid, so the story goes, around $52,000,000 for the property which carried 2011 taxes of more than $886,000.

Miz Winfrey still owns her long-time, 4-unit combination Chicago duplex at Water Tower Place as well as a 4,607 square foot Streeterville condo she bought in 2006 for $5,600,000 and recently (re-)listed for $2,800,000. It's now in contract. She also owns a number of less significant properties in Tennessee, Illinois and Indiana, most of which are believed to be occupied by family members.

Real estate watchers expect Miz Winfrey will eventually purchase a posh pied-a-terre in Los Angeles since the commute from Montecito to her OWN offices in L.A. is considerable, ninety minutes on a good day by car. Of course, she may be holding off to see if her limping network is going to sink or swim. We shall she, puppies, we shall see.