$3,595,000
6 Bed • 7 Bath • 5,972 Sq. Ft.
69 Rye Road
Rye, NY 10580
Listed with Houlihan Lawrence Inc.
$4,500,000
Est. $27,175/moChappaqua, NY 10514 · Westchester County
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1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!
As reported by the listing office; verify enrollment with the district.
Listed with Julia B Fee Sothebys Int. Rlty · Joanna Rizoulis · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 3:09 PM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
8
Sep 2026
Average Price
Active listings
$1,857,441
Sep 2026
Average Days on Market
Active listings
92 days
Sep 2026
Computed from 34 active OneKey MLS listings in Chappaqua, NY.
$3,595,000
6 Bed • 7 Bath • 5,972 Sq. Ft.
69 Rye Road
Rye, NY 10580
Listed with Houlihan Lawrence Inc.
$5,750,000
3 Bed • 4 Bath • 6,336 Sq. Ft.
14 Brittany Lane
New Rochelle, NY 10805
Listed with William Raveis Real Estate
$4,650,000
6 Bed • 6.5 Bath • 6,091 Sq. Ft.
11 Oak Lane
Larchmont, NY 10538
Listed with Houlihan Lawrence Inc.