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$2,137,500
4 Beds ⋅ 6 Baths ⋅ 1025674 MLS
A rare opportunity to create a forever home on nearly 7 private acres in the Chappaqua School District. Rich in history, character and natural beauty, 82 Shingle House Road is a distinctive Millwood estate for the buyer who values land, privacy and potential over cookie-cutter perfection. Originally dating to 1762, the property has evolved over time and offers a unique combination of old-world charm, generous space and exceptional flexibility. The main residence features spacious living areas, a large chef’s kitchen, fireplaces, beautiful natural light and peaceful views of the grounds. While the home offers great bones and many modern day appealing features, it is ready for the next owner to bring vision, updates and restoration to make it truly their own. Set on approximately 6.97 acres, the grounds are what make this offering so special: a private pond, mature trees, landscaped stonework, concrete pool, hot tub, cabana, open lawns, wooded surroundings and an extraordinary sense of seclusion. Additional improvements include a detached guest cottage situated above a three-car garage, plus a second three-car garage with a private pine-paneled retreat and a private meditation space with a stone fireplace, offering endless possibilities for guests, extended family, office, creative or recreational use. This is a property for someone who wants more than a house. It is for the buyer who wants a setting, a lifestyle and the chance to restore and personalize a truly special estate in one of Westchester’s most sought-after school districts. Rare, private and impossible to duplicate, 82 Shingle House Road is ready for its next chapter.

82 Shingle House Road, Millwood
$4,500,000
5 Beds ⋅ 7 Baths ⋅ 950756 MLS
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!

150 Old Farm Road N, Chappaqua

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.