Laguna Beach, California Villa Rockledge, a Mission-style six-villa compound perched high on the cliffs of Laguna Beach, was built by hand in 1918. The 5,000-square-foot brainchild of builder Frank A. Miller and designer Arthur Benton, it “ranks up there as one of the most beautiful homes anywhere on the coast of California,” Huell Howser, host of California’s Gold, a local PBS history and travel show, told The Wall Street Journal. The reddish brick compound was added to the National Registry of Historic Places in 1984 and was once a coveted getaway for Hollywood stars like Clifton Webb, Robert Mitchum, and Errol Flynn. Today, it’s one of the priciest homes in Laguna Beach. “If you’re really into ocean views,” writes Matt Coker in the OC Weekly, “this place seems to have them from all directions.” Greenwich, Connecticut Oldfield Farm is made up of 20 manicured acres bordering a land trust in one of America’s toniest—and richest—towns: Greenwich, Connecticut. Home to a 20,000-square-foot Palladian-style villa, the estate includes a pool, tennis court, horse stables, and a groom’s quarters. The property’s curvy driveway is breathtaking, too: It snakes along green fields and ends at the tasteful, custard-colored mansion’s front door. A must-have for the equestrian set. “Very refined, yet restrained,” wrote one commenter on the website Luxist.com. “Looks like a home that someone would actually live in.” Which is notable for Greenwich, a town in which many estates tend to be over-the-top. New York, New York The Duke-Semans Mansion, a 19,500-square-foot Beaux-Arts behemoth, made Curbed’s “ 20 Biggest Residential Deals of the Decade" list—and rightfully so—when real-estate magnate Tamir Sapir bought the place for $40 million in 2006. One of three private residences on Manhattan’s Fifth Avenue, it’s the only one to enter the real-estate market in years, having just sold for $40 million. Built in 1901, the eight-level Upper East Side home includes a penthouse duplex, a doctor’s office, 12 bedrooms, 14 bathrooms, and 11 wood-burning fireplaces. Pasadena, California Millard House, built in 1923, is more of a museum than a home. Designed by the legendary architect Frank Lloyd Wright, the 2,400-square-foot textile-block villa is, as the Los Angeles Times puts it, “an utterly modern, and democratic, expression of [Wright’s] organic architecture ideal.” Even Wright once said, “I would rather have built this little house than St. Peter’s in Rome.” A simple, three-story manor, it includes three bedrooms, a two-story living room, and a terrace with a reflecting pool. A separate studio, designed by Wright’s son, Lloyd, was added in 1926. The house’s downside: occasional flooding. “You will be sorry to know we had a very hard time during the recent flood,” Alice Millard, the home’s first owner, wrote in a letter to Wright in 1933. “The storm drain was not adequate. The ravine filled up. The basement was entirely full of water.” Cohasset, Massachusetts The Oaks—once owned by Clarence Barron, who purchased Dow Jones & Co. in 1902—is located on a nine-acre lot about 20 miles south of Boston. The resort includes a 20,000-square-foot 45-room mansion, a tennis court, pool, and private beach; the Cohasset Harbor Resort, a 55-room inn and conference center; and a marina and restaurant. The main house, an ivy-covered Georgian Revival, has eight bedrooms, a wood-paneled library, and an English-style pub in the basement. Of the property, Jonathan P. Radford, a Coldwell Banker agent, told The Patriot Ledger, “There are many individual properties that are attractive on the East Coast, but I have not found anything that combines four properties that essentially make up an entire harbor.” Montauk, New York This four-acre Montauk, New York, compound—just 75 feet above the Atlantic Ocean’s shoreline—stands in stark contrast to many of Long Island’s more traditional estates. Designed by James Biber, the low-slung home bucks “the trend for quaint clapperboard and shingles,” as Wallpaper magazine puts it, and “makes the case for a return to a modernism infused with craft, taste, and a sense of place.” Perhaps it’s no surprise, then, that the modernist residence won a 2007 American Architecture Award and gained some renown for its funky, red-walled home theater. Combining steel, glass, wood, stone, and brick, the compound includes a 7,192-square-foot main house with two L-shaped sections and a guest home, supported on steel beams, with a yellow circular outdoor staircase. Windermere, Florida Versailles—a name the house was given by time-share mogul David Siegel after he visited the French palace—is billed as the largest single-family home in America. The 90,000-square-foot mansion on Lake Butler in Florida includes 13 bedrooms and 23 bathrooms; a 20-car garage; 11 kitchens (one of which has a hibachi grill that seats 12); two movies theaters; six pools; an indoor roller skating rink; a two-lane bowling alley; and a 7,200-square-foot grand hall. But wait—there’s more: 1.4 miles of lakeshore; a stadium-size tennis court; and a full-sized baseball diamond. “It would be perfect for a sheik with a harem. I mean, there are plenty of bedrooms for all of his wives’ children, too,” Lorraine Barrett, the home’s real-estate agent, told My Fox Orlando. “Or maybe I was thinking a rich Russian that likes to show off his money.” Aspen, Colorado West Buttermilk Estate, located near Colorado’s scenic Aspen Valley, is the ultimate getaway pad. The 14,989-square-foot villa includes seven bedrooms (the master is massive, with sleek wood-paneled ceilings); six bathrooms; a wine cellar, home theater, and gym; and several fireplaces, decks, and terraces. Plus a couple of extra buildings, too: a two-bedroom caretaker’s unit and an eight-stall horse stable—with a hayloft, tack room, and plenty of storage. Beautiful, wide-spanning views of the Rocky Mountain terrain are a given. Westhampton Beach, New York Seafield Estate, a 16,000-square-foot waterfront home on 10.4 acres, was bought in 1903 by William C. Atwater, a coal baron. Designed by the architect Henry Bacon—famous for his design of the Lincoln Memorial in Washington, D.C.—it features a three-story staircase in the entryway and a banquet-size dining room. “You wouldn’t be able to recreate it,” Len Conway, who owns the property, told The New York Times, “and if you tried to replace it, to do it modern, but keeping with the details that are there, it would be at least $1,000 a square foot.” The home includes nine bedrooms and nine baths, as well as a carriage house, a pool, a tennis court, century-old grape vines, and a cottage. And a deepwater dock, too. Henderson, Nevada Las Vegas has become known for creating a sense of being elsewhere, and this nearby estate—or mini-medieval European village, really—helps prove why. Surrounded by Lake Las Vegas and Lake Mead National Park, the 6,500-square-foot home feels less like Nevada and more like southern France. This shouldn’t be surprising, though, because that’s exactly where the estate’s reclaimed bricks and stones—and 300-year-old Bavarian pine tree, too—were imported from. To add to the faux old-timey feel, the home also features a fresco-ceilinged living room, three fireplaces, a bell tower, and four “casitas” (one-room guest homes). Then there’s a spa, a saltwater pool, and a three-car garage. Los Angeles, California Ennis House, another textile-block architectural wonder designed by Frank Lloyd Wright, is located in the hilly Los Feliz neighborhood of Los Angeles. Built in 1924, the home’s design is based on ancient Mayan temples. One of Wright’s most famous creations, it was featured in several movies— Day of the Locust in the ’70s and Blade Runner and Black Rain in the ’80s—and has become renowned in the architecture world. Flooding, however, has caused significant water and structural damage over the years, much of which was fixed up by three nonprofit agencies recently. “It’s a trophy property,” Linda Dishman, executive director of the Los Angeles Conservancy, told NPR. “Some people have trophy wives—this is a trophy house.” Meaning, it’s perfect for a deep-pocketed buyer with a passion for Wright’s architecture. San Francisco, California The Museum Tower Penthouse, a 20,000-square-foot residence located on the top floor of San Francisco’s St. Regis Hotel, boasts 22-foot-high windows with a 360-degree panoramic view of the city and the surrounding region. Among its many amenities: six bedrooms, seven baths, two offices, four powder rooms, four fireplaces, a gym with a sauna and steam room, a wine storage room, a 13-seat theater, and 2,900 square feet of terraces. “It’s certainly the most extraordinary apartment outside of New York, and probably one of the two or three biggest homes in San Francisco,” Patrick Barber, managing broker with Sotheby’s International Realty, told the San Francisco Chronicle. Sante Fe, New Mexico Located on the outskirts of Sante Fe, New Mexico, on an 11.5-acre plot, this contemporary Pueblo revival-style compound features a 15,000-square-foot main house, a guest home, a casita, and heated horse stables. The main home includes eight bedrooms, nine full baths, and four fireplaces. There’s also a pool, hot tub, and spa, as well as an outdoor kitchen. Stunning mountain views of the surrounding canyon—full of red sand and dried-up desert shrubs—are part of the deal, too. East Hampton, New York A four-acre compound owned by the Breyers ice cream family, this East Hampton spread includes a 7,500-square-foot French-style mansion; two guesthouses and a caretaker’s cottage; a gunite pool with a pool house, lounge area, and changing rooms; a two-car garage and a workman’s shed; and two vacant lots. The main house has four bedrooms and six bathrooms. Alpine, New Jersey Located just eight miles outside of Manhattan, this 30,000-square-foot New Jersey villa sits on two acres. The five-story mansion includes 12 bedrooms, 19 bathrooms, and four kitchens, an 11-car garage, nine fireplaces, a wine cellar (which fits more than 3,000 bottles and uses thumbprint security to get in), tennis courts, a two-lane bowling alley, two pools, and a movie theater. It’s said to be the state’s highest list price ever for a home. “Nothing’s sold for that kind of money in New Jersey,” Jack Turpin, owner of Turpin Realtors, told Forbes.