Chatham, NY Homes for Sale

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

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 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

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.

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

Discover this charming 1920's two-family home nestled off a quiet one-way side street in the Village of Chatham. This well-maintained duplex has so much to offer- lots of natural light, hardwood floors, updated kitchens & baths, vinyl clad Thermopane windows, vinyl siding, spacious living & dining rooms, a large back yard and each side offers an enclosed sunporch & laundry room. A smart

Anne Harrison Country Life Real Estate, LLC

Rich in history, 1 Hudson Ave was originally built in the late 1800s with many additions and modifications over time. For many years, the Capozzo family operated a fruit and confectionery store with an adjoining billiard parlor. The capozzo family took up residence on the second floor.In 1984 the iconic Video Visions opened it's doors. Beloved by many, the VHS rental store and ice cream parlor

Linnea VanTassel Country Life Real Estate, LLC

Two newer homes for the price of ONE, situated on almost 30 acres! The stunning chalet built in 2018, consists of 2bedrooms + office/den in basement, offering a spacious and inviting open floor plan perfect for entertaining(indoor & outdoor!), tons of natural sunlight & so much more. Adding to the allure is a newly constructed detached garage, completed in 2023, which includes a 1BED/1BATH

Paige Ryan Core Real Estate Team

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

Tucked in the Hudson Valley, Foxglove & Fern is a 101-acre sanctuary where rolling meadows, ancient trees, and two ponds create a peaceful retreat. The 7-bedroom main house exudes warmth, with an inviting living room, a dining room anchored by a hand-laid stone fireplace, and a kitchen designed for gathering. A detached office offers endless possibilities—an artist's studio, a private retreat, or

Heather Etzel Four Seasons Sotheby's International Realty

Discover this exceptional custom home nestled on 5.97 acres, complete with a serene ponda perfect blend of privacy and convenience. Located in Chatham, this property offers endless potential, whether you're seeking a private retreat or an investment opportunity. Currently configured as a two-unit, it can easily be transformed into a charming single-family residence. Since its purchase in 2020,

Allison Rada Stone House Properties, LLC

Discover this exceptional custom home nestled on 5.97 acres, complete with a serene ponda perfect blend of privacy and convenience. Located in Chatham, this property offers endless potential, whether you're seeking a private retreat or an investment opportunity. Currently configured as a two-unit, it can easily be transformed into a charming single-family residence. Since its purchase in 2020,

Allison Rada Stone House Properties, LLC

Unique, mixed-use opportunity in the Village of Chatham on 0.17 acre with great exposure and free on-street parking. Currently used by the resident/seller, as retail on first level and two apartments above. Apartments could also be created on first level. The diverse 4,566 sq. ft. building featuring a rare backyard with lush landscaping, fountain and mature arborvitae along paneled fencing for

Frances Ingraham- Heins William Pitt Sothebys Intn'l

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

Steps away from thriving Main Street in Chatham, this fully occupied three unit building offers strong returns. Continue to rent the three units or occupy one unit and have the building cover your expenses. There is ample off street parkingas well as a fenced back yard and a sweet front porch..

Philip Feiner Country Life Real Estate, 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. Located near restaurants, shops, Chatham Brewery, and the renowned Crandell Theater, home to the Columbia Film

Melinda Barbanti Davala Real Estate, LLC

Open House April 19th 12PM - 2PM. Charming 1850 two-family home in the heart of Chatham Village, tastefully renovated by a nationally known writer. Live on one side and rent the other, or use as a pure investment. Just a short trip to Main Street, with its classic Crandell Theatre, award-winning brewery, Bimi's Canteen, and all the small-town energy you want. Out front of the home is a deep front

Open House April 19th 12PM-2PM. Charming 1850 two-family home in the heart of Chatham Village, tastefully renovated by a nationally known writer. Live on one side and rent the other, or use as a pure investment. Just a short trip to Main Street, with its classic Crandell Theatre, award-winning brewery, Bimi's Canteen, and all the small-town energy you want. Out front of the home is a deep front

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

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

Custom designed and built country contemporary in a very quiet setting. This light filled home offers almost 4000 sq ft of spacious, one level living. The finished living area is ADA compliant with open floor plan and wide passages. The Great room is central to the home and leads to additional gathering rooms, breakfast area, screened porch and stone terrace. There is an en suite master, with 3

Linnea VanTassel Country Life Real Estate, 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

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.

Hilltop land so close to Malden Bridge and Old Chatham? Here is an opportunity to own an impressive parcel of land in one of the most beautiful towns in the Hudson River Valley, Chatham NY. This is a 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

Thomas Jan Van Alstyne Anderson Agency

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