$619,900
5 Bed • 2 Bath
110-112 S Jacqueline Street
New Windsor, NY 12553
Listed with RE/MAX Benchmark Realty Group
$549,900
Est. $3,522/moMiddletown, NY 10941 · Orange County
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Cherished through generations and lovingly maintained by its owners, this remarkable circa home is ready for its next chapter. Set on 3.6 beautifully level acres in the Valley Central School District, the property offers the perfect blend of historic character, functional space, and country charm. As you approach, the care and pride of ownership are immediately evident. A welcoming front porch invites you inside, where you'll discover timeless architectural details and a warmth that only a well-loved home can provide. Upon entry, take notice of the unique concave wall, setting the tone for the character found throughout. The formal living room features a Franklin stove vented through the repointed chimney, complemented by a faux marble mantel, elegant pocket doors, and built-in bookcases. A spacious formal dining room with oversized windows and wide moldings provides the perfect setting for holidays, celebrations, and everyday gatherings. The kitchen offers abundant storage with two deep pantry closets, an additional utility closet, built-in stove, double sink, and convenient half bath. A main-level home office with its own closet creates an ideal work-from-home space. Upstairs, you'll find four generously sized bedrooms filled with natural light. The spacious primary bedroom includes a walk-in closet and linen closet, with indications of a possible original stove location hidden behind the wallpaper. An oversized full bath features a large window and soaking tub. The finished lower level offers additional living space, including a fabulous craft area, family/TV room, and abundant storage. A walk-up attic provides easy-access storage options rarely found today. One of the home's most beloved features is the sunroom—a peaceful retreat where every season brings a new view. Enjoy your morning coffee while listening to birdsong and taking in the beauty of the surrounding acreage. Outside, the possibilities are endless. The level 3.6-acre property is ideal for horses, small animals, gardening, recreation, or simply enjoying open space and privacy. A detached 1,136-square-foot garage/barn offers tremendous flexibility for vehicles, equipment, a workshop, hobbies, or agricultural use. Organic gardens. Rich in character, filled with history, and surrounded by picturesque grounds, this special property offers a rare opportunity to become the next steward of a truly grand old home.
As reported by the listing office; verify enrollment with the district.
Listed with Weichert Realtors · Rosalie W Cook · 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
77
Sep 2026
Average Price
Active listings
$559,324
Sep 2026
Average Days on Market
Active listings
152 days
Sep 2026
Computed from 325 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
$529,000
3 Bed • 3 Bath • 2,504 Sq. Ft.
104 Ayers Court
Montgomery, NY 12549
Listed with KW Hudson Valley United