Chatham, NY Houses for Sale

Fall in Love with This Private Saltbox Retreat on 21+ AcresWelcome to your own secluded paradise—this charming Saltbox-style home is perfectly nestled on 21.4 private acres, offering complete privacy and beautiful views of the Catskill Mountains and Hudson Valley.Thoughtfully positioned so that no neighbors are in sight, this home is tucked away in nature where the only sounds

Jason Walch Coldwell Banker Advisor Realty

At the heart of this timeless hamlet sits The Chatham House, offering a poetic blend of early American architecture and modern ease. Thoughtfully evolved over centuries, the home preserves its soul while embracing the comforts of today.Inside, light spills through elegant original windows and into the sweeping central hall and formal sitting rooms on either side of the house. A library and office

Alexandra Demetrakis Upstate Down

Welcome home!This thoughtfully restored 1880's village residence maintains its original integrity. The home has been meticulously renovated, featuring spacious rooms with lofty ceilings, abundant natural sunlight, and beautiful hardwood floors throughout.A beautiful front entryway opens to an elegantly curved staircase and parlor. Just beyond the French doors an inviting dining

Lenore Packet Stone House Properties, LLC

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,

Joseph Briggs William Pitt Sotheby's

Contractor Special: Office building ready for transformation to many possibilities. Common areas can accommodate open living/dining/kitchen concepts. Wideboard floors throughout. Attached shed serves as ample storage. A detached three bay garage is also on this 1.5 acre lot. Bring your vision for single-floor living to this blank slate just outside of Chatham Village.

Jennifer Wall Anderson Agency

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

Brittany Craig Houlihan Lawrence Inc.

A Chatham farm property with endless possibilities. Anchoring this 7-acre parcel is a 3BR, 3-1/2 BA home surrounded by fields, paddocks and woodlands. Set off from the home is an amazing barn complex and spring-fed pond. All less than a minute to downtown Chatham and equally close to the Taconic Pkwy. The property abuts the 65-acre Borden Pond conservation land - a hiker's paradise. The barn

Jason Karadus Corcoran Country Living

The Waterfall House is a modernist masterpiece, uniquely defined by its own cascading waterfall--a view you can enjoy from every room. Wade in the serene swimming hole below or wander through the exquisitely landscaped gardens that surround the home. Cozy up by the living room fire and admire the waterfall through a dramatic wall of glass.Designed to exist in perfect harmony with its natural

Lisa Bouchard Hoe The Kinderhook Group, Inc.

Elegantly poised on 56.47-acres, this exceptional estate encapsulates the very essence of luxury living. A pristine pond, versatile outbuildings, and panoramic mountain views create a magnificent backdrop of natural splendor. The interior unfolds as a symphony of lavish indulgence, boasting the finest stainless steel appliances, a sumptuous sauna, 2 executive offices and a stunning wet bar within

Vera Cohen Vera Cohen Realty, LLC

Elegantly poised on 56.47-acres, this exceptional estate encapsulates the very essence of luxury living. A pristine pond, versatile outbuildings, organic garden & panoramic mountain views create a magnificent backdrop of natural splendor. The interior unfolds as a symphony of lavish indulgence, boasting the finest appliances, a sauna, 2 executive offices, a wet bar, outdoor kitchen. A sprawling

Vera Cohen Vera Cohen Realty, LLC

Former Schoolhouse Completely Redone1840s One room schoolhouse with the most amazing floors and exposed beams. Come in through the original entrance! The classroom is now a living room with a fireplace and full bath. The expansive and well appointed kitchen has all locally crafted handmade cherry cabinets. A den just off the kitchen is perfect for a post dinner chat. The french doors lead out to

Emma French Gabel Real Estate

Nestled in a serene, wooded setting, 326 Pratt Hill Road is a thoughtfully designed Cape-style home that blends rustic charm with modern comforts. Originally a quaint cabin, it has been carefully expanded over the years and now offers three bedrooms, two full bathrooms, and 8.1 private acres – perfect for a weekend escape or year-round living. The oversized living area features hardwood floors, a

Callan Bergmann Compass Greater NY, LLC

At the end of a dead end road. Close to Chatham yet a world of privacy. 1874 gem with a post and beam barn to drool over. Historic cottage with original floors. Handcrafted features. Cherry kitchen with great storage and workspace. Dining area open to a deck overlooking the blooming bulbs, ornamental trees, flowering shrubs and picture perfect vegetable and cutting garden. Two bedrooms. Huge

Tracy Tassinari Gabel Real Estate