Courtesy: Four Seasons Sotheby's Int.
518-822-0800
Set along one of the most beautiful roads in Columbia County, this extraordinary country property offers a rare convergence of architecture, design, and landscape. Surrounded by 13 gorgeous acres of rolling hillside and forest, the setting feels both cinematic and deeply peaceful. Just beyond, the road is famously home to the Chatham Sheepherding Company's iconic complex of vernacular barns and agricultural buildings, lending the area a distinctly historic and pastoral character that is increasingly difficult to find. This is a home with true soul--restored and refined with remarkable sensitivity. The interiors were led by a House & Garden UK 100 designer, and that level of design fluency is immediately apparent. Every decision feels intentional, creating spaces that are quietly luxurious, deeply livable, and impossible to replicate. Throughout the home, original character is honored and elevated through exceptional materials and thoughtful detailing. Wide-board antique pine floors run throughout, grounding each room with warmth and patina. Even the smallest elements were considered: Forbes & Lomax brass switches punctuate the walls like jewelry--subtle yet unmistakably luxurious. Lighting by Workstead brings sculptural warmth to the interiors, while Lefroy Brooks bathroom fittings introduce a quietly classic sensibility rooted in craftsmanship and timeless design. The living spaces unfold with intimacy and grace. A richly layered library wrapped in custom shelving invites slow mornings and long evenings. A stunning music room, anchored by a grand piano and bathed in soft natural light, feels both elegant and welcoming. The kitchen and dining spaces are especially compelling--bright, beautifully composed, and effortlessly functional, with bespoke cabinetry, marble surfaces, and seamless connection to the outdoors for summer dinners and quiet morning coffee. The home offers three bedrooms plus a flex space, allowing for a variety of uses--guest quarters, office, studio, or media room. Each space has been designed with extraordinary sensitivity to proportion, light, and texture, resulting in interiors that feel collected over time yet perfectly resolved. What makes this property so exceptional is not simply its beauty, but its atmosphere. It possesses that elusive quality of the very best country houses: sophistication without formality, design without excess, and luxury rooted in authenticity. A truly rare offering--an extraordinary design-forward retreat on one of the county's most storied roads, immersed in the timeless beauty of the Hudson Valley.
Courtesy: Stone House Properties, LLC
518-392-0332
Charming 3-Bedroom Ranch on 14 Acres in Old Chatham, NY Discover peaceful country living at its finest in this inviting 3-bedroom ranch-style home, nestled on a sprawling 14-acre parcel in Old Chatham. Offering the perfect blend of comfort, functionality, and outdoor adventure, this property is ideal for horse enthusiasts, nature lovers, and those seeking a private retreat just minutes from charming local amenities and the scenic Hudson Valley. Step inside to find a bright, single-level layout designed for easy living. The three bedrooms provide ample space for family, guests, or a home office, while the open flow between living areas creates a warm and welcoming atmosphere. A highlight of the home is the screened-in porch--perfect for morning coffee, evening relaxation, or entertaining while enjoying fresh air and views of the surrounding countryside without a single bug in sight. A full basement offers tremendous potential--whether you're looking for additional storage, a workshop, a home gym, or future finishing into extra living space, the possibilities are endless. Outside, the 14 acres truly set this property apart. Enjoy wide-open skies and dedicated horse pasture complete with a small barn--ready for your equine companions or future projects. Whether you're riding, gardening, hiking your own trails, or simply soaking in the tranquility, this land delivers endless opportunities for rural recreation and self-sufficiency. Located in the desirable Old Chatham area, you'll benefit from the tranquility of country roads while remaining conveniently close to Hudson, Great Barrington, and the Berkshires. Farm stands, cultural attractions, and outdoor activities are all within easy reach. Contact us today to schedule a private showing and experience the lifestyle this exceptional property has to offer!
Courtesy: Gilcrest Properties
518-610-8121
Escape to the country and settle in at this inviting three-bedroom, two-bath home set on a beautifully maintained property in a highly desirable location. The spacious interior features a massive great room perfect for gathering with family and friends, a large loft offering flexible living space, and a cozy pellet stove that adds warmth and charm throughout the seasons. Enjoy the outdoors from the screened-in porch overlooking the picturesque yard, designed for relaxation and entertaining. Whether hosting summer barbecues, enjoying quiet evenings under the stars, or spending weekends away from the city, this property offers the ideal setting. Additional features include a paved driveway, a one-car garage with workshop space, and ample upstairs storage. Conveniently situated between the Hudson Valley, the Capital Region, and the Berkshires, you'll enjoy easy access to shopping, dining, cultural attractions, outdoor recreation, and year-round activities. Ideal as a weekend retreat or a full-time residence, this unique property offers exceptional space, versatility, and location. Please note: the home is technically classified as a manufactured home and is not financeable through conventional lending; cash purchasers are encouraged to inquire.
Courtesy: Stone House Properties, LLC
518-392-0332
Nestled on 12 private acres in the serene hamlet of Old Chatham, New York, this charming log cabin offers the perfect blend of rustic appeal and modern comfort, with breathtaking panoramic views of the Catskill Mountains that change with the seasons from vibrant autumn foliage to snow capped peaks in winter. The warm, inviting main home features 3 spacious bedrooms and 2 full baths, highlighted by classic log construction that fills the interior with natural wood tones and cozy ambiance. A welcoming porch spans the front, ideal for morning coffee while soaking in the mountain vistas or evening relaxation with friends. Additional highlights include a fully functional basement apartment perfect for guests, extended family, in law suite, or potential rental income providing flexibility and privacy. Step outside to your own private oasis: an above ground pool awaits for refreshing summer swims, surrounded by ample yard space and the tranquility of wooded acreage. Stay prepared and comfortable with a reliable backup generator, ensuring peace of mind during any weather event. Old Chatham's peaceful, rural setting dotted with rolling hills, historic charm, and easy access to the Hudson Valley's cultural offerings makes this an exceptional retreat or full time residence. Whether you're seeking a weekend escape or year-round sanctuary, this log cabin delivers authentic Catskills living with stunning views and room to roam. Don't miss this rare opportunity to own a piece of upstate paradise!
Courtesy: Gabel Real Estate
518-392-4975
A Grand Dame in Old Chatham. Discover the joy in bringing back a classic. All the bones are solid. Five bedrooms in that rambling feel that makes farmhouses so lovable. The great room fireplace combines stone and real wood panels with views of the pond out the windows. A formal dining with wainscoting leads to a kitchen that leads out back. A second living room that could be it's own apartment. Finish the primary and create a vaulted masterpiece. The land runs over 15 acres of forest with a magnificent pond. There's a garge at the house. Then there's a 40'x60' garage/workshop is perfect for the hobbiest.
Courtesy: Stone House Properties, LLC
413-232-4253
Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers generous space to gather and unwind with family and friends. At its center, the kitchen and living areas are designed for connection. The open kitchen and dining space flows easily into the main living room, where a stone fireplace anchors the room and creates a natural place to come together after a day outdoors. Stainless steel appliances and ample workspace make the kitchen as functional as it is welcoming, equally suited to large weekend meals or quiet mornings overlooking the landscape. Windows throughout frame views of pasture, pond, and sky, keeping the surrounding land present from nearly every angle. Outdoor living is just as inviting. A stone patio with outdoor fireplace extends the entertaining space beyond the house, creating a natural gathering spot for summer evenings and crisp fall nights. A basketball court and playground add to the sense that this is a property meant to be enjoyed by all ages. For the equestrians at heart, the property is thoughtfully equipped with a 12-stall stable, heated tack room, paddocks, and outdoor riding facilities, offering everything needed for both recreational and more serious riding. A detached office provides additional flexibility — ideal for working from home, a studio, or a quiet space removed from the main house. The land is what truly sets the tone. Whether on horseback, on foot, or exploring by ATV, the acreage offers a sense of freedom and room to roam that's increasingly rare. Trails wind through meadow and forest, eventually leading to a private stretch of Kinderhook Creek with its own natural pebble beach — an ideal spot for quiet afternoons, summer swims, or simply taking in the setting. This is a property designed for gathering, for outdoor living, and for making full use of the landscape in every season. Equal parts retreat and playground, it offers a combination of privacy, scale, and natural beauty that defines Hudson Valley country living at its best.
Courtesy: Brown Harris Stevens HV LLC
518-828-0181
Where History Breathes and Beauty Dwells: WHITE BRIDGE FARM c1775 Welcome to White Bridge Farm, an exquisite historic18th century estate restored and designed honoring and preserving the history with imagination and perfection. White Bridge Farm will take your breath away at every turn from the original restored iron main gate to magical stonewalls, pathways and gardens landscaped to intrigue all your senses with three miles of trails to the magic in all her structures. Pause at sitting areas overlooking the stream, the waterfall and fields with fountains and fire-pits and decorative arbors found throughout this160-acre sanctuary. The 1700's main home, with enchanting courtyard, interior and exterior original and authentic details is comprised of three bedrooms, formal living and dining rooms each with wood burning fireplace, the masterful kitchen, office, mudroom and four full baths and one-half bath. The main level primary en-suite with double height ceiling, wood burning fireplace and master bath is stunning. Upstairs you will find two sunlit en-suite bedrooms and an inviting sitting area. The roof is of handcrafted "dog-ear" copper tiling. All other buildings have copper standing seam roofing. The air is central, and floors are radiant, as in all living structures. The Barn complex creates a delightful courtyard comprised of two guest suites flanked by two magnificent barns. The main level ‘Bridle Suite', with flagstone flooring on the main level is an intriguing open concept space with original stall walls retained to define the spaces opening to brick patio. Above, the light-filled three bedroom ‘Hayloft Suite’ with restored wood flooring has open dining, three bedrooms and lounging terrace. Each suite has Big Chill appliances, WBFP, radiant flooring and W/D. The Barns: the "Horse Barn', has original cobblestone floors and completely restored. The stalls are intact and decorated as living spaces for gathering and bath with shower and copper tub with Lillie Herbeau filter. Upstairs is open space with soaring ceilings to dance, dream and create. The "Gathering Barn" completely restored with soaring ceilings and all original beams and intact stalls originally for hunting dogs decorated as living spaces and grand open spaces for gathering is truly incredible. Attached is a four bay garage with original barn doors, radiant floors and custom storage. The pool house with floor to ceiling stone wood burning fireplace and soaring ceiling highlighting architectural trusses is fabulous, as are the kitchen and bath. French doors open to the custom gunite pool with seating area designed to take in the views and surrounded by gracious plantings and gardens with bluestone decking, pergola, hot tub and stone shower. The systems throughout the property are as spectacular. A magical property for a lifetime of memories. Truly a sanctuary to be marveled.
Courtesy: William Pitt Sothebys Int Rlty
518-392-0244
A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, a fully equipped eat-in kitchen, and a gracious formal dining room—an exceptional blend of timeless architecture and modern luxury. The grounds are equally compelling, featuring a spacious in-ground pool, a tranquil pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, amenities rival those of a private resort, with a full gym, game and entertainment room, home theater, and a refined library creating an environment of comfort, recreation, and retreat. A finished attic and an impressive 4,500-square-foot barn with foosball and ping pong provide additional flexible space for leisure and gathering. Fiber-optic internet and a full-house generator ensure seamless modern living, while the estate's thoughtful infrastructure and meticulous maintenance support effortless year-round ownership. Bellavista stands as a premier private estate, offering a rare combination of total privacy, exceptional amenities, and enduring quality. Just minutes from Chatham, Hudson, and Kinderhook—and a short drive to Lenox, Stockbridge, and Great Barrington—the property is surrounded by acclaimed farm-to-table dining, art galleries, organic markets, and the historic Crandell Theater. Easily accessible via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, and Albany International Airport, Bellavista is as convenient as it is extraordinary.
You know what they say about brick houses, "they're mighty, mighty"Super sweet location for this privately situated country home in horse country. Ez one story living with updated kitchen and baths. The gathering rooms are open to each other and the living room offers a brick fireplace. There is a full bath off the hall and a half bath off the primary bedroom.Bring the horses, goats or chickens as there is plenty of pasture and a good 2+ stall barn with water, electric and it's own access. Walk to the beautiful Ooms conservancy land for hiking or fishing. You're less than 10 min to Chatham Village, 35 min to Albany and easy access to the Taconic State Parkway. Come hang your hat!!
In the heart of Old Chatham, is this rare opportunity to purchase a historic, well maintained, 3 unit property with views of breathtaking, cascading waterfalls. The Old Chatham Post Office currently occupies one unit (3 years remain on the lease) and, there are 2 updated, currently vacant apartments to rent, live in or use as office space. The two level, 2 bedroom apartment and a 1 (could be 2) bedroom apartment both feature wide board floors and original woodwork. Each unit has its own meter, and utilitiesThe building has been in loving hands for many years. and the owner occupied one of the units There have been numerous improvements to the property: a new roof, heating systems, water heaters. new fencing and deck are a few of the upgrades.The mature and lush landscape is a sight to behold. There is a full and heated walkout basement which is usable in part for a studio or work area. Immediate income and easily rented apartments make this investment a sure thing! Close to Chatham Village and an easy drive to Hudson, Albany and the Berkshires.
Discover your private country retreat on this lush, secluded property set back from the main road. This charming home welcomes you with a covered front porch perfect for morning coffee or evening relaxation while enjoying the peaceful surroundings.The main level features a spacious living room perfect for gatherings or quiet evenings. The updated kitchen boasts modern appliances, elegant cabinetry, and flows into a generous dining area ideal for entertaining.Step through the rear of the home onto a spacious deck, creating an ideal outdoor living space for al fresco dining, entertaining, or simply unwinding while taking in the serene property views.The expansive yard offers endless possibilities host summer barbecues, create your dream garden with raised beds and flowering perennials, or simply enjoy the open green space. With room for outdoor games and gatherings, this property provides the perfect backdrop for creating lasting memories.Outdoor enthusiasts will appreciate the proximity to three Columbia County Conservancy locations Ooms, Hand Hollow, and Schor offering miles of scenic hiking trails. The Empire State Trail is also nearby for biking and walking adventures. Cultural attractions abound with Art Omi just minutes away and the future home of the Shaker Museum in the vicinity.This move-in ready home requires no renovations, allowing you to immediately enjoy its character and comfort. The property includes a versatile outbuilding perfect as a home office, studio, workshop, or storage space.Additional features include an Adirondack basement system and newer furnace/central air for year-round comfort and efficiency.
Tucked into the heart of the Hudson Valley, where life slows and nature flourishes, lies Foxglove & Fern a breathtaking 101-acre sanctuary. As you follow the circular driveway, rolling meadows, ancient trees, and a shimmering private pond welcome you to a world of serenity.More than a home, this estate is a legacya place where generations gather, and every sunrise brings new adventures. The main house features seven spacious bedrooms, two of which once served as a private library and study, offering endless possibilities as creative retreats or home offices. Sunlit interiors, timeless character, and stunning views define each space.The heart of the home is a warm, inviting living room, while the dining room is anchored by a hand-laid stone fireplace, perfect for candlelit dinners. The chef's kitchen, outfitted with stainless steel appliances and a Viking double oven, is designed for both casual gatherings and gourmet creations.Equestrians will appreciate the 12-stall stable, heated tack room, paddocks, and outdoor riding facilities. Meandering trails invite horseback rides or quiet nature walks. A detached office provides a fully wired workspace, offering a seamless blend of work and retreat.With approximately mile of frontage along Kinderhook Creek, a charming pebble beach is perfect for skipping stones, floating downstream, or simply enjoying nature's tranquility. One of two private ponds, the 2.5-acre pond offers space for boating, fishing, or peaceful reflection. A stone patio and outdoor fireplace create an inviting setting for entertaining under the stars, while a basketball court and playground add to the estate's charm.Despite its seclusion, Foxglove & Fern is ideally located. Lake George, hiking trails, and ski resorts are just a short drive away, with Hudson's vibrant culture only 30 minutes away. Amtrak access allows for effortless travel to NYC and Boston, making this estate a perfect balance of retreat and accessibility.
A post and beam barn on a dead end road in Old Chatham. Cathedral ceilings, walls wrapped in windows, bring in light and views from every angle. In the great room a brick fireplace with a chestnut mantle. Open floor plan makes it easy for entertaining. Shaker cabinets, soapstone counters, and hand crafted lighting. First floor primary bedroom ensuite with walk in closet. Two additional bedrooms upstairs both en suite.. One bedroom with extra bunk space. Outside, an oversized deck looking out to the bucolic rolling 8 acres. Lower level with high ceilings waiting to be finished.
Courtesy: GABEL REAL ESTATE CC
One of the few brick Georgians in Columbia County, the Samuel Wilbur House is a stately reminder of the past. Wilbur, a NYS Senator during the Colonial era, created a home of outstanding beauty and balance. Huge original barns, renovated Carriage House, 20 x 40 heated, saltwater pool, bluestone patios and stream give the outdoor space an instant country feel. The home consists of five separate but connected living spaces, each with their own kitchen, baths and bedrooms. A family compound in a single building, a small inn or bed and breakfast. All of the finishes are of the highest quality, with many of the original details intact. The floors have over a century of patina, the moldings are hand crafted, the fireplace mantels works of art, exposed beams and bricks lend interest to the ceilings and walls. Updated where it's needed, particularly in the main kitchen where modern aesthetics give clean thought to this antique beauty. Wonderful new windows bring in the light and amazing original windows, including the original Palladian window in the upper hall
Courtesy: ILLUSTRATED PROPERTIES GROUP LLC CC
Stunning contemporary colonial in absolute like-new condition set far back on 11+ acres with scenic pond and rolling park-like views in prime Old Chatham. This understated country masterpiece offers low maintenance living with current streamlined style and premium comfort features throughout. Three gracious living levels with soaring 9' ceilings, solid walnut floors, masterfully crafted trim/millwork , spectacular white quartz/shaker/stainless kitchen, 3.5 updated baths, 2 wood burning fireplaces (LR and Primary BR), 400 amp electric, premium high efficiency Viessmann boiler with 6 zones including 2 zone radiant heat in kitchen/foyer and entire lower level, Bosch mini-split cooling with 6 zones, main level laundry, office/guest room over garage w/ skylights, workout room/studio space in lower level, loads of closets, giant wrap around deck of 1000+ sq ft, and the list goes on. A gorgeous turn-key private retreat built to the highest standards in a lovely setting just 1 mile from the hamlet of Old Chatham, 10 mins to Chatham Village and 30 mins to Hudson or Albany.
Courtesy: GABEL REAL ESTATE CC
Raccoon Forks is the type of country home that you never tire of. The land rolls into the view of the Chatham hills and countryside. The pond sits just waiting for you to jump in! The quiet and private country road is perfect for strolling. Two homes opens the possibility of rental or a family compound. The main home's Posts and Beams combine for a stunning display of engineering prowess. A huge kitchen stretches across the back of the house with plenty of room for your inner master chef. The dining area can spill to the deck with its pond and mountain views. The living room is anchored by a field stone fireplace. The formal dining can handle a crowd. The loft upstairs makes a great office or a huge bedroom. Two more large bedrooms with a sitting room downstairs. The guest house has a gorgeous kitchen, a nicely sized living room and two more big bedrooms. The most wonderful spot to enjoy the country!
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Old Chatham is located in New York. Old Chatham, New York has a population of 772. Old Chatham is more family-centric than the surrounding county with 29.02% of the households containing married families with children. The county average for households married with children is 22.64%.
The median household income in Old Chatham, New York is $116,471. The median household income for the surrounding county is $73,065 compared to the national median of $69,021. The median age of people living in Old Chatham is 57.2 years.
The average high temperature in July is 81.9 degrees, with an average low temperature in January of 13.3 degrees. The average rainfall is approximately 44.6 inches per year, with 52.8 inches of snow per year.
