Chatham, NY homes for sale & real estate

Chatham, NY Homes for Sale

Charming and walkable 4BR home in the heart of Chatham village! Set on a spacious half-acre lot, this sun-filled home blends original character with modern updates—featuring hardwood floors, a flexible layout with home office/music room, and plumbing in place for a second bath. Enjoy golden hour on the front porch or entertain in the deep, private backyard with a stone patio. Steps to yoga, bookstores, co-op, restaurants, and more. Minutes to Hudson, Berkshires, ski resorts, and nature trails. A perfect full-time or weekend retreat!

Chatham, NY Homes for Sale

Welcome to Dogwood Cottage! Tucked along one of the most darling streets in the Village of Chatham, Dogwood Cottage is a storybook gem framed by the blooms of its namesake tree. Set on a sweet quarter-acre lot, this 3 bedroom, 2 bath 1945 ''Victory Cottage'' offers the perfect blend of charm, privacy, and village convenience. Inside, natural light pours through every room, highlighting the warmth of original hardwood floors and a thoughtfully designed custom kitchen. Cozy up by the fire on a chilly fall evenings after a walk to one of the many restaurants in the village. One of the three bedrooms is conveniently located on the first floor, offering flexibility for guests, work-from-home nee

Chatham, NY Homes for Sale

Chatham Village Income Gem! This tastefully updated Craftsman two-family offers substantial investment return and steady income. Situated on a quiet village street, this meticulously maintained property with two spacious, side-by-side units, each featuring 3 bedrooms, an office area, sunroom, and large enclosed entryway. Enjoy a large yard, four-car garage, and storage/workshop. Recent improvements include a rebuilt chimney and cap, extensive tree work, fresh interior and exterior paint, updated kitchens and appliances, and new garage siding and doors. Benefit from long-term, reliable tenants and walkability to all village amenities, including shops, restaurants, and the Co-op. Conveniently

Chatham, NY Homes for Sale

This well-maintained multi-unit building offers a strong investment opportunity, with numerous updates, upgrades, and consistent maintenance over the years. The perfect opportunity to live and invest simultaneously, with three units that cater to both owner-occupants and investors. As of July 1st, 2025, Apt #3 with 2 Bedrooms will be available, making it perfect for those looking to owner occupy. Located near restaurants, shops, Chatham Brewery, and the renowned Crandell Theater, home to the Columbia Film Festival, this property combines charm and practicality. Each apartment features upgraded kitchens equipped with dishwashers, along with thoughtfully designed spaces that offer unique char