Courtesy: Brown Harris Stevens Hudson
518-828-0181
Willow Pond Retreat — 12 Acres of Serenity and Soul Welcome to Willow Pond Retreat, a soulful, private 12-acre country sanctuary where life is meant to be lived, not merely observed. Here, whispering willows frame a tranquil pond, daffodils bloom in abundance, and meandering garden paths invite you to wander among mature trees and timeless beauty. The four bedroom, four bath main home exudes warmth and character — with three fireplaces that beckon in every season and a sunlit kitchen that opens to nature's ever-changing landscape. An in-ground pool, newly lined in deep navy and surrounded by lush, established gardens, creates a resort-like oasis for long, languid summer days. Thoughtfully as well as privately connected to the main residence, a self-contained apartment offers versatility for guests, extended family, or inspired use as a studio or retreat. A spacious workshop/studio outbuilding extends the creative potential — ideal for artisans, makers, or those seeking meaningful workspace. Even the charming chicken coop adds a touch of pastoral whimsy to this self-sustaining haven. Private, romantic, and deeply functional, Willow Pond Retreat is both a home and a way of life — a place where beauty feels effortless and every element has soul.
Courtesy: Brown Harris Stevens HV LLC
854-871-2700
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: Gabel Real Estate
518-392-4975
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: William Pitt Sothebys Int Rlty
518-392-0244
Escape the bustle of city life and discover Bellavista Country Estate, a grand 12,000-square-foot Georgian brick residence set on over 25 private acres in the foothills of the Berkshires, ideally situated between the Hudson River Valley and the Berkshires. Designed for both gracious living and effortless entertaining, the estate offers six to nine beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, a fully stocked eat-in kitchen, and an elegant formal dining room—seamlessly blending timeless sophistication with modern comfort. Recreation and relaxation abound, with 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, a full gym, game and entertainment room with arcade favorites, home theater, and a library of hundreds of books invite endless enjoyment, while a finished attic and a 4,500-square-foot barn with foosball, ping pong, and bar space provide additional areas for leisure and gatherings. Every detail has been thoughtfully attended to, from fiber-optic internet and a full-house generator to weekly pool and grounds maintenance, ensuring ease of ownership and year-round comfort. Since 2011, Bellavista has been maintained as a premier private estate, equally suited as a full- or part-time residence, a multigenerational retreat, or a hybrid work-from-home haven, also offering a successful proven 5-Star luxury rental business. Just minutes from Chatham, Hudson, and Kinderhook—and a short drive to Lenox, Stockbridge, and Great Barrington—the property is surrounded by farm-to-table dining, art galleries, organic markets, and the renowned Crandell Theater. Convenient access via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, and Albany International Airport makes Bellavista as accessible as it is extraordinary.
Courtesy: William Pitt Sothebys Intn'l
518-392-0244
In the heart of Chatham's historic hamlet of Malden Bridge, this 19th century three bedroom Colonial house, on almost an acre of land, is the ideal country home with modern updates on one of the most bucolic roads in Columbia County. The light filled living room opens directly into the dining room with lovely French doors that lead to a screened porch, ideal for relaxing or evening dining. The spacious eat in kitchen has a modern stainless steel farmhouse sink, quartz counters, gas stove and a walk-in pantry for storage. The kitchen leads to a very spacious mudroom for coats & boots, ample cabinetry, a sink for additional prep space, a half bath and the back door that opens to the new stone patio. The original staircase leads to the second floor with three bedrooms and a bath with shower. The basement has high ceilings, a new concrete floor & beautiful stone walls, currently the location of a home gym & the laundry with a new washer & dryer. The house retains many historic details with modern updates such as energy efficient heat pumps for air conditioning, whole house water filtration & an efficient propane fired heating system. The classic two story red barn has space for a car, a workshop, storage & a large second floor, a possible studio or finished additional living space. On almost an acre of flat land, there is room for a pool, large gardens or an orchard. Across the road is the Malden Bridge Community Center with yoga classes, community events or available to be rented for your next party or a large Thanksgiving dinner, which the sellers have done. Minutes to Old Chatham restaurants & Chatham Village shops, cafes, bookstore, cheese shop, Crandell Theatre, PS 21 for dance and cultural events, the soon to open new Art Omi Pavilions and the Shaker Museum. A short drive to Hudson and Amtrak or to the Berkshires for Tanglewood, theatre, museums & winter skiing. Under 2.5 hours to NYC.
Courtesy: Brown Harris Stevens HV LLC
854-871-2700
CEDAR HILL - A HOUSE for all SEASONS - Old Chatham NY If you’re looking for sweeping views, clean modern lines, and a luxurious connection to nature, this high-design country estate delivers. Elevated on 10 private acres, the newly reimagined six-bedroom home sits in one of the most coveted corners of New York’s Hudson Valley. Seamless indoor-outdoor flow highlights the drama and beauty of every season—from summer’s golden light to autumn’s artistry to snow-capped mountains in winter. The property was completely rebuilt and expanded in a years long renovation completed in 2023 for year-round sustainable, modern living. Solar power, multiple EV charging stations, and radiant-heated interiors ensure comfort in every season. Walls of glass capture southern light and frame panoramic mountain views, while expansive bluestone patios lead to a 50-foot heated gunite pool. The cedar-clad spa pavilion—with sauna and a custom hot tub— as well as a fire-pit and illuminated tennis court—complete the private resort atmosphere, perfect for restorative retreats, festive gatherings, or quiet relaxation. Inside, soaring ceilings, abundant light, and warm finishes create interiors that balance drama with comfort. A great room anchored by a wood-burning fireplace flows into a chef’s kitchen with butler’s pantry, gracious dining area, and a second gathering room. A game and media room opens directly to the pool terrace, while the main level also offers a first-floor bedroom and bath, plus a fabulous mudroom with breezeway access. Upstairs, the primary suite is a private sanctuary, with glass doors opening to a deck that captures sunrise and mountain vistas. Four additional upstairs bedrooms, a flexible bonus room and a second laundry provide space for family, guests, work, or wellness. Surrounded by the natural beauty of the Hudson Valley and the Berkshires, Cedar Hill is a bargain that offers the best of both access to hiking, skiing, farm-to-table dining, and cultural destinations—while remaining a peaceful retreat to relax and recharge in modern.
Courtesy: Coldwell Banker Village Green
518-625-3360
Set on 21 peaceful acres in one of the Hudson Valley's most coveted locations, 'Dawnbreak' is an Adirondack-inspired property offering a rare opportunity to create a beloved retreat. With over 3,200 square feet of living space, this four-bedroom, four-bathroom home combines rustic charm with generous proportions—ready for your vision to bring it to life. At the heart of the home is a dramatic Great Room featuring soaring ceilings, rich wood paneling, exposed beams, and a wood-burning stove set against a brick chimney. A wall of windows bathes the room in natural light and frames sweeping views of the surrounding hilltop landscape—an ideal setting for gatherings both large and small. Designed for connection and comfort, the home also includes a welcoming sit-in dining room, a windowed library, and a secondary living area with an adjacent bedroom and separate entrance—well-suited for guests, creative use, or a flexible workspace. Four wood-burning fireplaces throughout the home add character and warmth. The 21-acre setting includes open meadows, wooded areas, and a small creek—an inspiring canvas with room to add a pool, gardens, or outbuilding. A three-bay garage and whole-house generator provide year-round functionality and ease. Located just minutes from the vibrant village of Chatham—close to everyday amenities as well as restaurants, farm markets, and cultural venues—and close to the Taconic State Parkway, I-90, Hudson Amtrak, and Albany, this is a rare chance to create a one-of-a-kind Hudson Valley escape. Bring your vision and make this Old Chatham haven your own. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Coldwell Banker Village Green
845-331-5357
Set on 21 peaceful acres in one of the Hudson Valley’s most coveted locations, ‘Dawnbreak’ is an Adirondack-inspired property offering a rare opportunity to create a beloved retreat. With over 3,200 square feet of living space, this four-bedroom, four-bathroom home combines rustic charm with generous proportions—ready for your vision to bring it to life. At the heart of the home is a dramatic Great Room featuring soaring ceilings, rich wood paneling, exposed beams, and a wood-burning stove set against a brick chimney. A wall of windows bathes the room in natural light and frames sweeping views of the surrounding hilltop landscape—an ideal setting for gatherings both large and small. Designed for connection and comfort, the home also includes a welcoming sit-in dining room, a windowed library, and a secondary living area with an adjacent bedroom and separate entrance—well-suited for guests, creative use, or a flexible workspace. Four wood-burning fireplaces throughout the home add character and warmth. The 21-acre setting includes open meadows, wooded areas, and a small creek—an inspiring canvas with room to add a pool, gardens, or outbuilding. A three-bay garage and whole-house generator provide year-round functionality and ease. Located just minutes from the vibrant village of Chatham—close to everyday amenities as well as restaurants, farm markets, and cultural venues—and close to the Taconic State Parkway, I-90, Hudson Amtrak, and Albany, this is a rare chance to create a one-of-a-kind Hudson Valley escape. Bring your vision and make this Old Chatham haven your own! A 3D Walkthrough Tour is available in the digital Lookbook or by request from the listing agent.
Courtesy: Houlihan Lawrence, Inc
518-822-0300
Step back in time and own a piece of Old Chatham history with the distinguished Samuel Wilbor House. Built circa 1770 and listed on the National Register of Historic Places, this exceptional estate offers a unique opportunity to live amidst authentic historic character. Once home to New York State Senator Samuel Wilbor, this is one of Columbia County’s few remaining brick Georgians, and is a stunning example of early American architecture lovingly adapted for modern life. Set on picturesque grounds in the quaint hamlet of Old Chatham, the estate includes a beautifully updated main house, three stylishly renovated apartments, and a chic converted barn. Inside, generously proportioned rooms provide comfortable living with a total of 9 bedrooms and 10 updated bathrooms across the property. The main house features rich original white pine woodwork, hand-carved moldings, exposed beams, four fireplaces, and a striking original Palladian window. An expansive kitchen with breathtaking floor-to-ceiling windows, creates a light-filled culinary haven that blends contemporary functionality and beauty with the home's traditional character. Each of the three attached apartments features its own private entrance, offering flexibility for continued rental income, live-work arrangements, or in-law accommodations. The stunning barn conversion currently serves as a yoga studio and event space, offering endless possibilities for personal use or income generation. A two-car garage with a bonus workshop is ideal for creative projects or extra storage, and surrounding bluestone patios lead to a heated saltwater pool and outdoor entertaining area. This is an extraordinary opportunity to own a piece of Old Chatham history reimagined for modern living. Whether you seek a grand estate for family and friends, a unique investment property with multiple income streams, or a harmonious blend of residential and recreational spaces, the Samuel Wilbor House is an exceptional offering in a coveted location.
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.
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.
