104-108 Highland Avenue

Historic Elegance Meets Modern-Day Convenience in this circa 1860 home in the heart of Middletown, NY. Pristinely positioned back from the road, set on just shy of an acre, this historic gem offers 3500+ square feet of timeless character and space. From the moment you enter, soaring ceilings, rich hardwood floors, built-ins and detailed crown molding set the tone. The expansive dining room, living room and formal parlor are thoughtfully connected by solid wood pocket doors - perfect for both grand entertaining and intimate gatherings. A full bath just off the parlor adds flexibility, making it ideal as a playroom or guest space. A true standout, the wood paneled library/den exudes warmth and sophistication, complete with its own powder room, an ideal retreat or home office. The light-filled kitchen offers everyday functionality and leads to a spacious back covered porch overlooking the level backyard and detached 2 car garage. Upstairs, the primary suite is complemented by private office/bedroom and beautifully renovated (2026) bath with Signature Hardware vanity. Three additional bedrooms include a Jack-and-Jill bath, plus another full bath, a dedicated laundry room, and a charming music room offering space for every need. The detached garage has new garage doors with electric opener and plenty of storage with loft area. Adding to its rich history, the home was once owned by an individual connected to the story of the Titanic - an intriguing piece of its past that enhances its timeless allure. Commuter-friendly with easy access to Metro-North and Shortline Bus, along with a vibrant, revitalized downtown filled with dining and shopping. Nearby Garnet Health Medical Center, Touro College of Osteopathic Medicine, SUNY Orange, recreational parks, golf, and so much more.