Chatham, NY Homes 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 you'll hear are

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

Eden personified. A true country fairyland. Quiet dirt road leading to a dead quiet spot. Meander up the long private drive past the tennis court & swimming pond to a classic country shake & stone farmhouse. Walk through the gated garden to the front entry. High ceilings & views rolling over the pond. Flowering trees & gorgeous perennial gardens. Beamed ceilings & stone fireplace. Window seats

Andrea Gabel Gabel Real Estate

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

Charming 2-Bed, 2-Bath Single-Wide Mobile Home in Sought-After Chatham - No Age Restrictions!Don't miss this rare opportunity to own a beautifully maintained 2-bedroom, 2-full-bath single-wide mobile home in the highly desirable area of Chatham—and best of all, it's located in a non-55+ community!This home offers a bright, open-concept layout with a spacious living area, a functional kitchen with

Margaret Guerra Gilcrest Properties

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.

Unique Mixed-Use Opportunity in the Heart of Chatham VillageThis rare 4,566 sq. ft. mixed-use property on 0.17 acres offers prime visibility in the Village of Chatham, complete with free on-street parking and a rich blend of business, residential, and lifestyle potential. Thoughtfully renovated by the resident/owner, two storefronts have been combined into a vibrant boutique and pottery studio

Joseph Briggs William Pitt Sothebys Int Rlty

A newer and, truly beautiful, manufactured home that is1800 sq feet and will be less expensive monthly than renting! The home is in Edgewood Acres, an established and well maintained community property in Chatham. The home features an update and large kitchen with stainless appliances and plenty of storage.. There are 3 bedrooms and 2 baths. The primary en-suite bedroom has a HUGE walk-in

Peter Newman Beach & Bartolo Realtors

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.

Enjoy this private country property located near a rural historic community. Located just a short drive to the NYS thruway and Mass Pike. Enjoy a short drive to the beautiful Berkshires and Jiminy Peak ski resort. Located minutes to the Taconic State Parkway for a scenic drive to NYC. There are two power poles on property located to the right of the meadow.

Barry Shatney Bovair Real Estate

A little slice of heaven. Situated between the hamlets of New Concord and Red Rock this lot is ready for its future owners home. Percolation test has been done for a BOHA letter. There is an existing well on the property. Less than 10 minutes to Chatham with easy access to the Taconic state parkway from the East Chatham exit. Less than 30 minutes to Jiminy Peak, Hudson, Pittsfield, Lenox and

Tyler Bervy Stone House Properties, LLC

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

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

Melinda Barbanti Davala Real Estate, LLC

Nestled in the heart of Chatham, this 123-acre pristine wooded paradise is a rare gem. With a serene pond and enchanting old stone walls that meander throughout the property it is a harmonious blend of natural beauty and timeless character. Here are 123 acres of unspoiled land. The property is a truly stunning canvas of mature trees, stone outcroppings and picturesque landscape. There are two

Laurie Ylvisaker Coldwell Banker Village Green

Chatham Village two-family with substantial investment return and steady income producer available. The tastefully updated craftsman is set on a quiet village street with a large yard, two car garage, and storage/workshop area. The side by side two-level units both have 3 bedrooms, office area, sunroom, and large enclosed entryway. Recent improvements include; chimney rebuild and cap,

Rachel Haley Houlihan Lawrence, Inc

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

Hilltop land so close to Malden Bridge and Old Chatham? Here's an opportunity to own a parcel of land and nature in one of the most beautiful towns in the Hudson River Valley, Chatham NY. Private and secluded 27+ acre parcel nestled between the hamlet of Malden Bridge and Riders Mills Road and situated on a town-maintained, paved road. This wooded parcel has a combination of deciduous, coniferous

Thomas Jan Van Alstyne Anderson Agency, Inc.

Nestled along a tranquil country road, discover 65 breathtaking acres of pristine land, offering a harmonious blend of open fields, enchanting woodlands, and serene stream. This idyllic parcel invites you to build your dream home amidst nature's splendor, providing ample space to roam, explore, and unwind.Imagine mornings spent wandering along picturesque stone walls and scenic walking paths, or

Nikki Carchedi STONE HOUSE PROPERTIES, LLC