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Peek Inside Westchester County’s Most Expensive Homes

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Photo courtesy of Leslie McElwreath

From a retreat set on a private island to stately waterfront mansions, indulge in 10 of the county’s most expensive — and impressive — homes on the market.

When high-net individuals go shopping for real estate, wine cellars, home theaters, and infinity pools are standard fare. After all, when you’re talking mega-price tags, it’s all about the amenities.

Whether you’re looking to relocate, upsize, sequester in seclusion, or lean into the whole work-/school-/play-from-home thing, Westchester has something for everyone to consider, especially if your pockets are deep enough. Take a peek into where and how the other half (make that the 1%) lives.

Photos courtesy of Leslie McElwreath

– 1 –
$30,000,000

8 BR, 13 BA; 31,000 sq. ft.; 14 acres; estimated taxes: $205,000

14 Cowdray Park Dr, Armonk

Just Pack Your Polo Mallet
Set in the very exclusive Conyers Farm enclave — a 10-acre-zoned gated community that counts Ron Howard and Paula Zahn as former residents — this European manor offers stunning, unobstructed views and is just a stroll away from the Greenwich Polo Club fields. Totally reimagined by acclaimed designer Steven Gambrel and fully furnished and appointed, all you’ll need to add is a butler. All the extravagant comforts of home — including indoor and outdoor pools, a palatial reception hall, conservatory, and billiards room — await. (This property has a Greenwich PO, but is located in Westchester.)
Listed by Leslie McElwreath, Sotheby’s International Realty


Photos courtesy of Dolly Lenz Real Estate

– 2 –
$19,500,000

7 BR, 12 BA; 19,387 sq. ft.; 10 acres; estimated taxes: $181,302
17 Cowdray Park Dr, Armonk

It’s Got Game
Another palatial estate on Conyers Farm, and another conservatory, this sprawling, custom-designed, 26-room French Revival home on the shores of Converse Lake also comes with major b-ball cred: It’s owned by former NBA star Allan Houston. In addition to the conservatory, you’ll find an indoor basketball court (naturally), cinema, rec room with bar, marble steam room, playground, and golf green. (This property has a Greenwich PO, but is located in Westchester.)
Listed by Dolly Lenz, Dolly Lenz Real Estate


Photos courtesy of Houlihan Lawrence

– 3 –
$15,500,000

6 BR, 12 BA; 16,064 sq. ft.; 35 acres; estimated taxes: $229,464
9 Holly Branch Rd, Katonah

Right Up Your Allée
If you’ve been yearning for an allée (a very elegant-looking drive lined on both sides with evenly spaced trees), you’ll want to consider this gracious fieldstone mansion. Approached by a 1,200-foot driveway lined with English oak and pear trees, it has a private two-acre lake fed from a stream. A pool-and-tennis complex accessed by a separate drive; a dramatic, floating staircase; and the requisite indoor basketball court complete this picture of majestic living.
Listed by David Turner, Houlihan Lawrence


Photos courtesy of Ginnel Real Estate for 15 Honey Hollow

– 4 –
$15,000,000

5 BR, 7.5 BA; 9,822 sq. ft.; 16.47 acres; estimated taxes: $95,070
15 Honey Hollow Rd, Pound Ridge

Homestead For The Horsey Set
This glorious country estate dating back to 1860 is the perfect place to hunker down in style for any season. Overlooking a private lake and the Stone Hill River, and bordering the Ward Pound Ridge Reservation, the clapboard Colonial home has been meticulously restored with wide-board pine floors, crown moldings, and coffered ceilings. Throw in a pergola-covered terrace with outdoor fireplace, a barn with gym, pool, guesthouse, and chicken coop, and there’s really no reason to leave — except perhaps to set out on horseback on the adjacent Bedford Riding Lanes trails.
Listed by Benjamin Ginnel, Ginnel Real Estate


Photos courtesy of Compass Greater NY

– 5 –
$13,500,000

7 BR, 8 BA; 10,957 sq. ft.; 23 acres; estimated taxes: $117,280
8 Hickory Kingdom Rd, Bedford

Your Own Magical Kingdom
Preside over your own private lakefront estate tucked behind a gated entry. This stately stone manor marries the best of old and new — 2006 construction with an old-money aesthetic. Survey the enchanting parklike setting, replete with specimen trees, flowering gardens, and expansive meadows from the inviting patio, porch, or deck. Indoors, the property continues to charm, with soaring ceilings, custom stonework, double-height windows, and other top-of-the-line appointments.
Listed by Brian Milton, Compass Greater NY


Photos courtesy of Julia B. Fee

– 6 –
$13,200,000

8 BR, 7.5 BA; 8,900 sq. ft.; 18.41 acres; estimated taxes: $84,703
35 Schoolhouse Rd, Waccabuc

Country Estate With Cultural Cachet
This stunningly landscaped country estate will hold particular charm for devotees of music and art. Formerly owned by Tony Award-winning producers, it comes with its own one-of-a-kind performing-arts venue — a custom-built amphitheater that has hosted performances by the New York Philharmonic, Marvin Hamlisch, James Earl Jones, and Tommy Tune. A bronze sculpture by Hanneke Beaumont and Storm King-like sculpture gardens, plus a pool, cabana, tennis court, and wooded walking path, make this property, featuring a main house and four-bedroom guest cottage, a very special find.
Listed by Melissa Collabella & Anthony Lando, Julia B. Fee Sotheby’s International Realty


Photos courtesy of Julia B. Fee Sotheby’s International Realty

– 7 –
$13,000,000

4 BR, 2 BA; 5,625 sq. ft.; Columbia Island: 2 acres, Pea Island: 5 acres;estimated taxes: $42,885
1 Columbia Is, New Rochelle

Fantasy Islands
Take social distancing to a whole new level by acquiring not one but a pair of islands located on Long Island Sound. Reached by boat, the Columbia Island residence, perched 20 feet above sea level, offers spectacular water views of Manhattan and beyond. Want to get even farther away from it all? Paddleboard or kayak the .2 nautical miles to Pea Island, your second — and totally uninhabited — island, featuring an open beach and indigenous plantings.
Listed by Patti Anderson, Julia B. Fee Sotheby’s International Realty


Photos courtesy of Houlihan Lawrence

– 8 –
$12,995,000

9 BR, 14 BA; 18,359 sq. ft.; 3 acres; estimated taxes: $278,111
6 Carriage Trl, Tarrytown

Heaven-On-The-Hudson
Enter this elegant stone manor in the exclusive Greystone on Hudson gated enclave through an impressive covered portico and relax in your own reception room, boasting a sky-high 20-foot ceiling. The good life — complete with astonishing Hudson River views — awaits the new owners of this exquisite estate replete with covered porches, verandas, and patios. Other distinctive features include Old World moldings, a two-story mahogany library, a second kitchen, and an indoor basketball court.
Listed by Amy Ensign, Houlihan Lawrence


Photos courtesy of Renwick Real Estate

– 9 –
$12,800,000

9 BR, 14 BA; 20,618 sq. ft.; 25 acres; estimated taxes: $243,031
151 Sarles St, Mount Kisco

Tennis Everyone
A completely renovated Georgian manor dating back to 1930, Glencliff is located in an area chock-full of other fancy estates. Accessed by a gated entrance and long, winding driveway, it features a grand main house, two-bedroom guesthouse, pond, pool, cabana, and tennis court. If tennis is your game, it has also received approval for an indoor court.
Listed by Patricia Carpenter, Renwick Real Estate


Photos courtesy of Douglas Elliman

– 10 –
$11,950,000

6 BR, 8 BA; 9,766 sq. ft.; 57 acres; estimated taxes: $178,430
17 E Middle Patent Rd, Bedford

The Sweet Life
A charming and classy name? Check. Private orchards? Check. Fenced pastures where the horses can graze? Check, check, and check. Sugar Hill, a completely renovated and expanded whitewashed brick mansion circa 1936 will surely tick all the boxes of even the most discerning homeowner. A gated entrance, international-size tennis court, pool, and two-bedroom caretaker’s cottage complete the sweet setup.
Listed by Douglas Elliman