$2,299,000
5 Bed • 4.5 Bath • 4,661 Sq. Ft.
20 Hitching Post Lane
Chappaqua, NY 10514
Listed with William Raveis-New York LLC
$2,995,000
Est. $21,365/moBriarcliff Manor, NY 10510 · Westchester County
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There are homes… and then there are places that feel quietly set apart from the world around them. Tucked behind a gentle approach, on nearly four private acres in the heart of Briarcliff Manor, 36 Revolutionary Road reveals itself slowly, intentionally… like a secret meant only for those who understand what true luxury feels like. This is not just a home. This is a legacy estate. Set perfectly between the Hudson River and Sleepy Hollow Country Club, the location offers the rare balance today’s buyers search for privacy, proximity, and prestige. Minutes to Metro North, fine dining, boutique shopping, and everything that defines Westchester luxury living… yet once you arrive, the outside world seems to soften. There is a stillness here. You feel it walking the grounds, where mature trees frame rolling lawns and sunlight filters through in that unmistakable golden way. There is a rhythm to the property… the kind that invites long mornings on the porch, quiet afternoons by the pool, and evenings that stretch just a little longer than planned. And somewhere within it all… life quietly thrives. Bees drift from bloom to bloom, tending to the landscape in a way that feels both timeless and grounding… a subtle reminder that this estate is not just maintained, it is alive. Inside, the home unfolds with a level of craftsmanship and scale rarely seen today. Five ensuite bedrooms offer both privacy and comfort, anchored by a truly exceptional primary suite with its own fireplace, spa like bath, expansive dressing room, and a private sleeping porch… a nod to a more romantic era of living, where fresh air and slow mornings were part of everyday life. The kitchen is designed not just for cooking, but for gathering… a chef’s workspace complemented by a generous butler’s pantry, ideal for seamless entertaining. It flows effortlessly into a formal dining room that feels pulled from the pages of a design magazine, where hand printed Zuber wallpaper and a fireplace create a setting that is both refined and deeply inviting. Every room tells a story. A wood paneled office with its own fireplace opens to the front porch, offering a work from home experience that feels anything but ordinary. The living room, wrapped in double walls of French doors, blurs the line between indoors and out, filling the space with natural light throughout the day. Nearby, the sunroom becomes its own retreat… a place to pause, unwind, and simply take in the beauty of the property. Step outside, and the estate continues to reveal itself. A gunite pool set within manicured grounds. Multiple porches designed for every mood and moment. A historic Lord and Burnham greenhouse… a rare and remarkable feature that speaks to the property’s heritage. And a four plus car garage with a private apartment above, offering flexibility for guests, extended stays, or staff. This is Westchester luxury real estate at its finest, where historic architecture meets modern lifestyle, where privacy meets convenience, and where every detail has been thoughtfully considered. Because the truth is… You can always renovate a home. But you cannot recreate land like this. You cannot replicate this setting. And you cannot manufacture the feeling this property gives you the moment you arrive. 36 Revolutionary Road is not just being listed. It is being offered.
As reported by the listing office; verify enrollment with the district.
Listed with Houlihan Lawrence Inc. · Elaine Wasserman · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 18, 2026, 7:07 AM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
16
Sep 2026
Average Price
Active listings
$1,711,056
Sep 2026
Average Days on Market
Active listings
80 days
Sep 2026
Computed from 43 active OneKey MLS listings in Briarcliff Manor, NY.
$2,299,000
5 Bed • 4.5 Bath • 4,661 Sq. Ft.
20 Hitching Post Lane
Chappaqua, NY 10514
Listed with William Raveis-New York LLC
$3,595,000
6 Bed • 7 Bath • 5,972 Sq. Ft.
69 Rye Road
Rye, NY 10580
Listed with Houlihan Lawrence Inc.
$2,395,000
5 Bed • 4 Bath • 3,579 Sq. Ft.
7 Poplar Road
Larchmont, NY 10538
Listed with Julia B Fee Sothebys Int. Rlty