Homes for High Net-Worthers

The Four Most Expensive Homes in Westchester

$75 million
34 Lower Shad Rd, Pound Ridge
8 BR, 10.4 BA, 20,043 sq ft, 262 acres;
$233,034 estimated taxes

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It’s easy to see why this grand estate is the most expensive home on the market in Westchester. Its 260-plus acres—which spill into Connecticut—includes Versailles-worthy gardens, a greenhouse, a private lake, a life-size chessboard, barns, and lighted tennis courts complete with a shaded cabana viewing area. Inside, you’ll find opulent touches like imported antique marble, limestone, onyx, mosaic tile, and stained glass. Among its abundant spaces are formal living and dining rooms, cloak room, library, conservatory, and breakfast room. The final over-the-top touches? A sumptuous indoor pool with Italian mosaics and four guest/staff residences.
Listing courtesy ofRenwick Sothebys Int’l Realty.


$36 million
77 Oregon Rd, Bedford Corners
10 BR, 9.1 BA, 10,000 sq ft, 63.8 acres;
$189,794 estimated taxes

Classic, timeless elegance and sweeping open meadow and Hudson River views are the hallmarks of this 10,000-square-foot 1920s-era Georgian mansion. The serene setting (you approach the home via a gated, half-mile driveway that winds through an orchard) is complemented by outdoor amenities that include a heated pool with cabana, a tennis court, and a golf tee and greens. The interior of the main house (there is also a private guest house) is characterized by architectural details that include wide-board floors, Old World custom detailing, rich paneling, 9- to 11-foot ceilings, graceful archways, and six fireplaces. Bonus for golf enthusiasts: There is also an indoor golf simulator. Listing courtesy of Douglas Elliman Real Estate.


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$23 million
Glencliff, Bedford Corners
9 BR, 12.2 BA, 20,618 sq ft,
25.2 acres; $203,382 estimated taxes

If you’re looking for high drama, you’re $23 million is well spent here. Sleek, modern, and unexpected architectural and stylistic details (not to mention an elevator) abound at every turn—an interesting contrast to the home’s 1930s Georgian-manor exterior and pastoral location atop 25 acres of rolling meadows. The property—which boasts a pond, garaging for seven cars, two-bedroom guest cottage, 65-foot pool with cabana, and tennis court—borders the 150-acre Marsh Sanctuary, so you don’t have to worry about any pesky neighbors impinging on your sightlines with new construction. Listing courtesy of Renwick Sothebys Int’l Realty.


$19.9 million
17 Cowdray Park Dr, Armonk
6 BR, 10.2 BA, 19,387 sq ft, 10.29 acres;
$180,950 estimated taxes

Basketball fans with deep pockets may want to snatch up this home, which belongs to former New York Knicks star (and current Westchester Knicks GM) Allan Houston and features (obviously) an indoor basketball court and fully equipped home gym. The French-inspired stone showstopper also boasts a music room, gentleman’s library, custom-crafted trophy room, soundproof cherry-paneled home theater, oversized his-and-hers master closets, and the requisite gourmet kitchen. Outside, enjoy the putting green, heated pool with spa and poolside conservatory, and multilevel terraces overlooking spectacular gardens. Listing courtesy of Houlihan Lawrence Inc.

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