1. John Barrymore’s Hollywood Estate Has True Star Appeal.  
Westside Estate Agency

This magnificent Beverly Hills estate oozes Old Hollywood glamour and with good reason -- it was once home to silver screen legend (and Drew’s grandfather), John Barrymore. Built in the 1920s by John Byers in the architect’s signature Spanish Colonial revival style, the residence was originally owned by the film director King Vidor. Barrymore purchased the seven-bedroom home in 1927 and lived there until his death in 1942. The estate is full of unique and decadent details, including an entryway fireplace, an octagonal living room, an opium den, an oversized paneled library, and an in-home pub replete with floors fashioned from the trunks of redwood trees. In addition to the main house, the 3.4-acre property includes two guest cottages and a recently constructed two-story guest house. Owning this piece of Hollywood history will set you back $42.5 million. Click here to view the full listing.

2. Here's what you get when you combine a Gucci-owned penthouse and mid-century decor.
Brown Harris Stevens

High-fashion sisters Alessandra and Allegra Gucci have put their jaw-dropping Fifth Avenue penthouse on the market for a cool $45 million. Offering stunning views of Manhattan, the sun-fill loft spans 9,450 square feet and features soaring fourteen-foot ceilings, nearly thirty full-length windows, a wood paneled library with a limestone inset and a wood burning fireplace, a formal dining room, two commanding staircases, two interior elevators, and a lavish master suite fit for fashion royalty. The eight-bedroom residence has a decidedly modern feel thanks to its clean lines, bright palette, and mid-century decor. Click here to view the full listing.

3. Wow factor galore! This hip estate is located in one of Chicago's finest neighborhoods.
Redfin

Surrounded by some of Chicago’s most lavish (and expensive) homes, this $8.95 million mansion has a decidedly more playful and approachable spirit than its neighbors. Designed by local architects Liederbach and Graham, the 7,800-square-foot home features exposed brick and industrial metalwork throughout, which lends an edgy yet refined atmosphere. Situated inside a walled garden, the five-bedroom home’s entire ground level is open to the outdoors, creating an effortless flow between interior and exterior spaces. Other unique attributes include sky-high ceilings, a guest suite coach house, a 900-bottle wine cellar and tasting room, and a recreational room outfitted with a sauna. Click here to view the full listing.

4. Summer like President Obama for only $19 million (and the price just dropped over $3 million, even with the Obama pedigree).
Wallace & Co. Sotheby’s International Realty

The First Family’s former Martha’s Vineyard summer rental has hit the market with an asking price of $19 million. Known as the Chilmark House, the six-bedroom home was designed by Seattle architect Rick Sundberg and Falmouth landscape architect Steve Stimson and built by master builder Andrew Flake. Perched 120 feet above the Atlantic Ocean, the modern masterpiece is luxe yet liveable, with interiors that blend seamlessly with the stunning surroundings. Highlights include oak and radiant-heated limestone floors, marble baths, concrete fireplaces, a chef’s kitchen, a half-basketball court, a heated infinity pool, an expansive screened porch, outdoor terraces, and sweeping ocean views. The secluded, 9.5-acre property also includes a guest cottage and three private beach lots accessible from the home’s private dock. Click here to view the full listing.

5. Worth moving to Detroit? $260k buys you quite a grand home. Needs a little updating but...
Berkshire Hathaway Home Services

Let this six-bedroom Tudor gem take you back to the Motor City’s heyday. Located in the Villages of Detroit near the mayor’s mansion, the residence was built in 1922 by Robert O. Derrick, the architect responsible for the Henry Ford Museum. The 5,242-square-foot home retains a number of original details, including Pewabic Pottery fireplace surrounds and bathrooms and charming arched doors. While it is in need of some TLC, you can’t beat the $260,000 asking price. Click here to view the full listing.