Chatham Central School District, NY Homes for Sale
Welcome to Skyfields, a serene 42-acre sanctuary perched on a hilltop in East Chatham, offering far-reaching panoramic views of the Catskills, Berkshires, and surrounding pastoral valleys. This private retreat blends wooded seclusion with open country landscapes, featuring a charming main residence, a cozy guest cottage, and a versatile barn/garage—all thoughtfully updated and positioned for ultimate tranquility. This post-and-beam, 1.5-story home, constructed in 1976, spans approximately 2,200 square feet with three bedrooms and 2.5 bathrooms in the main house. The open layout emphasizes natural light through insulated casement windows with screens, complemented by sheet
Wooded seclusion • Spacious studio loft • Versatile barn
OPEN SUN, 12PM TO 2PM
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Chatham Central School District, NY Homes for Sale
Welcome to Bear Paw Creek. Explore this captivating 24.68-acre retreat in East Chatham, New York, where a private drive leads to an idyllic blend of historic charm and contemporary elegance in an 1825 farmhouse. Featured in Domino Magazine this designer home is nestled amid rolling pastoral valleys, dense woods, and a gently flowing stream, the property unfolds with sublime gardens, a unique heated in-ground pool sanctuary framed by two striking giant silos and an antique dairy barn with soaring ceilings—creating an enchanting escape for reflection and cherished moments, conveniently accessible to the Taconic Parkway, Hudson, and the Berkshires. This post-and-beam Colonial farmhouse,
Sublime gardens • Antique dairy barn • 24.68 acre retreat
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NEW 7 HRS AGO
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Chatham Central School District, NY Homes for Sale
A House by the Pond. A thoughtfully rethought ranch in a private picturesque setting near the end of a dead end road. Delight in the wildlife as sunbeams dance across the pond. Windows act as picture frames for the view. An open and airy layout where all the living space flows. The kitchen anchors with enough space to create epic feasts. Four bedrooms with wonderfully tiled baths. The primary has a screened porch for morning coffess or a nightcap.
Screened porch • Open and airy layout • 5 acre lot
NEW 16 HRS AGO
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Chatham Central School District, NY Homes for Sale
This historic home was constructed by Thomas Bishop, a veteran of the War of 1812 in the early 1800's and was once known as Bishop's Tavern. It began as an inn and tavern on what was once, the Stockbridge and Hudson stagecoach line. Since then it has been lovingly tended and updated with an eye to preservation. Located on a quiet country road in Red Rock and surrounded by mature gardens and stately trees this property has much to offer. The front of the house has access to two covered porches, one on each floor that offer seating and views of the pasture and hill beyond. Entering the home from the side, this open porch entry brings you into a large parlor that stretches across the length of
Quiet country road • Mature gardens • Historic home
Listing by Houlihan Lawrence
NEW 27 HRS AGO
ABOUT THIS HOME
Chatham Central School District, NY Homes for Sale
OWNER OCCUPIED. NO TRESPASSING or access please without appt. Showings to begin only on Mid renovation home situated on 6.58 acres where an overgrown pond was the little one's favorite cooling place in the summers of years gone by . .. this 1900+/- sqft single floor home is comprised of L style open floor plan incorporating kitchen/dining area/living room---down the hall are 4 bedrooms and full bath. Downstairs is full poured cement basement under original home and crawl space under addition. Vaulted ceiling breezeway connects house and oversized 2 car garage, plus additional 2 car size metal barn. Pretty and usable land. Note: mid renovation, momma lived there alone/ deferred maintenance a
Based on information submitted to the MLS GRID as of Wed Sep 17 2025. 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.
How to buy a house in Chatham Central School District, NY