$619,900
5 Bed • 2 Bath
110-112 S Jacqueline Street
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$765,000
Est. $4,934/moMiddletown, NY 10940 · Orange County
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Timeless Character. Endless Possibilities. Nestled on over 12 private, wooded acres along a quiet country road, this stately brick Colonial offers the rare opportunity to own a home where history, craftsmanship, and natural beauty come together. Built circa 1900 and encompassing more than 3,000 square feet, this remarkable residence is filled with the warmth and architectural character that only a historic home can provide. The classic brick facade, welcoming front porch, and mature landscape create an unforgettable first impression. Inside, oversized windows bathe each room in natural light while preserving peaceful views of the surrounding property. Original details throughout the home—including wide-plank wood floors, handsome millwork, multiple fireplaces, and gracious proportions—reflect the quality and charm of a bygone era. Offering four to five bedrooms and three full baths, the home provides an abundance of living space for everyday comfort and entertaining. The country kitchen captures the home's historic appeal, while formal living areas and generously sized rooms offer flexibility for today's lifestyle. One of the home's most captivating spaces is the stunning four-season family room, where soaring wood ceilings, walls of windows, and a dramatic wood-burning brick fireplace create an inviting retreat in every season. Whether enjoying a quiet morning coffee or gathering with family and friends, this spectacular room is certain to become the heart of the home. Outside, the property continues to impress. Over 12 wooded acres provide exceptional privacy and a peaceful setting without sacrificing convenience. A tremendous bonus is the attached heated three-bay garage with an expansive walk-up loft. Whether you're a car enthusiast, contractor, hobbyist, collector, or simply need room for recreational vehicles, equipment, or a workshop, this versatile space offers endless possibilities rarely found on residential properties. This home presents an exceptional opportunity for the next owner to enhance and personalize a property already rich in history and character. For those who appreciate timeless architecture, generous acreage, and the enduring craftsmanship of a historic home, this is truly a place unlike any other. This home is centrally located just minutes to Middletown, Matamoras, PA and the Otisville Station on the Metro-North Port Jervis Line.
As reported by the listing office; verify enrollment with the district.
Listed with RE/MAX Benchmark Realty Group · Patricia M Sassi · Source: OneKey MLS
Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Sep 17, 2026, 9:07 PM ET. ©2026 One Key MLS.
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Market Insights
Current Listings
New in the last 30 days
77
Sep 2026
Average Price
Active listings
$558,142
Sep 2026
Average Days on Market
Active listings
152 days
Sep 2026
Computed from 326 active OneKey MLS listings in Middletown, NY.
$619,900
5 Bed • 2 Bath
110-112 S Jacqueline Street
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$629,900
3 Bed • 2 Bath • 1,440 Sq. Ft.
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Listed with Howard Hanna Rand Realty
$589,900
4 Bed • 3 Bath • 1,780 Sq. Ft.
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Washingtonville, NY 10992
Listed with KW Hudson Valley United