luxury houses for sale Columbia County, United States

River Watch is quietly set back from the road and poised at the top of a hill. This purposefully chosen setting offers both Hudson River and Catskill Mountain views - sunsets are glorious. The hamlet is known as Young America and the residence, an 1890 Folk Victorian, reflects the artistry and design of a not so young American era. The rocking chair front porch, with its requisite turned posts and detailed brackets, sets the tone for the entire experience of serenity and charm. Enter through two sets of crafted double doors, via the vestibule, and into a sundrenched living room. Here we have built-in bookcases and cabinetry as well as double multi-light French doors which lead to the flower garden. The formal dining room, also imbued with magical light, easily provides space for vast farmers' market-fare meals prepared in the country kitchen with its generous butcher-block island. Wide doors open onto a large deck for al fresco meals and where your potted herbs and flowers will adorn both taste and table. Entertaining made simple. In every season. Throughout the house we have a mix of wide and medium board floors as well as traditional cottage style plank doors with wrought iron handles. The second floor is reached via two separate interesting staircases. Upstairs we have two landings, three quite comfortable bedrooms, and two full baths; yes, one with a claw-foot tub. The one-acre property is exquisitely dotted with old-growth trees and fenced flower as well as vegetable gardens. A silver maple on the east border might be the oldest tree in Germantown! Down the gravel driveway, along a laid stone wall, we reach a building. Within is a 2-car garage and fabulous studio! Presently used for pottery, but clearly available for your own, long-delayed artistic expression - No matter the medium: Sculpture, paint, movement, writing. If you think of it, it can be done here. Mostly. The vehicular area is so large it can be divided to provide for other desired space - gym, workshop, greenhouse, home office, or perhaps pool house. The property beyond this structure is open and level offering the perfect situation for a pool. At the north border, we have a sheltered brook which is a tranquil gift, a place to listen to her melodic sounds. Less than a one mile walk into the village center of Germantown, yet a world apart.

Don't miss an opportunity to own one of the most stately and desirable properties in the historic and charming Village of Kinderhook, the former hometown of Martin Van Buren, the Eighth President of the United States. Tucked in the center of the historic district, steps from the Village Square, sits a grand early Nineteenth Century colonial, on 1.3 private acres, which harkens back to a bygone era. The eighteen room home's distinctive features include a large front porch, nine over six windows, seven mantels, period moldings, vintage hardware, soaring ceilings, shiplap, built-in cabinets and bookshelves, and beautifully refinished classic wood floors. The owners have maintained the historic character of the home while updating the kitchen and baths to provide functionality and modern conveniences. The first floor is ideal for entertaining. Enter through the original eight panel front door to find the center hall complete with refinished narrow wood floors and a classic staircase with newel post. To the left of the entry hall is a huge parlor with large windows, hardwood floors, and beautiful woodwork. The hardwood floors, woodwork, and large windows continue into the adjacent formal dining room with original crystal chandelier. To the right of the entry hall is another large room with narrow board floors, vintage woodwork, and large windows, including a splendid bay window which floods the room with light. An impressive gathering room with architectural details, wide board floors and a crystal chandelier anchor the space at the rear of the entry hall. Also on the first floor is an eat in kitchen with vintage coffered ceiling, large pantry with hosier and open shelving, full laundry room with farm sink, half bath with classic tile floor, a spacious bedroom with period lighting and wide board floors, a separate dressing room with built-in cabinet, a mudroom, a heated screen porch, and an office with separate entrance. The second floor contains an immense primary bedroom with double closets, two additional large bedrooms with walk-in closets, and an ensuite bedroom with separate dressing room with vanity. A bath with a marble floor, updated shower, and period vanity service the three front bedrooms. The ensuite bedroom is serviced by a private bath with a marble floor, shower, and soaking tub. The ensuite can also be accessed by a private back staircase. There is a walk-up attic for ample storage, and a two-story mortise and tendon barn suitable for a workshop, additional storage or as a two-car garage. The private lot consists of 1.3 grassy acres of flat land with gardens, shade trees, and lots of wide-open spaces. There is ample room for a pool. The property is convenient to Hudson, Chatham, Albany, Troy, the Catskill Mountains and the Berkshires and easily accessible by car or train to New York City and Boston. It is a short walk to restaurants, coffee shops, a seasonal farmer's market, the post office, churches, art galleries, shops, parks, a museum, a garden center, an orchard, a yoga studio, the Kinderhook Creek boat launch, the Hudson River Valley Greenway, and all of the wonderful activities, concerts and events that make the Village of Kinderhook such a special place. Seize the opportunity to own a truly special property in a truly unique place before it is too late. Call to make an appointment for a private showing.

Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simplicity—ideal for a buyer who values design, nature, and ease. Tucked away yet minutes from Hillsdale, Hudson, Egremont, and Great Barrington, the location offers instant access to the region’s best culture, dining, and outdoor recreation. With NYC and Boston a little over 2 hours away, this property is the perfect full-time escape or effortlessly luxurious weekend base. A rare architectural and design statement, this steel-and-glass modern barn redefines country living for the buyer seeking something truly unique. Plans are available for a one or two bedroom addition.

This serene 5-acre property boasts open meadows and mature trees, offering a tranquil retreat that feels a world away, yet remains highly accessible to the best of the Hudson Valley and Berkshires. Its proximity to the Taconic State Parkway and Interstate 90 ensures an easy retreat from both New York City and Boston. Locally, you'll delight in the charming town of Chatham's cafes, restaurants, bars, and a burgeoning art museum scene, with Queechy Lake just a 10-minute drive away. Popular destinations like Hudson and Great Barrington are also easily reached in just 35 minutes. Inside, discover the ease of single-floor living, featuring a spacious living room with a high vaulted ceiling and a warming wood-burning fireplace. The perfectly updated kitchen is both tasteful and functional, complemented by three generously sized bedrooms and two full bathrooms. The full-footprint basement, partially finished, presents an excellent opportunity to create additional bedrooms, home theater or even a self contained inlaw suite. True to its agricultural surroundings, this perfect home is perched above grounds that are mostly flat and highly versatile for a variety of activities. A charming chicken coop is discreetly tucked behind a 1.5-car garage, inviting you to embrace the farm-to-table lifestyle of the area. A barn sits across the field behind the home providing a bucolic view and awaits your vision for an art studio, guest house or stable. Truly a fantastic value for those looking to find peace of mind in their own private Hudson Valley oasis.

Just two blocks from the most coveted stretch of Warren Street, the State Street House is an authentic c.1880 Victorian era townhouse that has been lovingly restored--honoring its historic character while introducing modern comforts with remarkable restraint and taste. Behind its understated facade, the main residence unfolds in a series of luminous, airy spaces defined by soaring ceilings, original wide-plank floors, oversized windows, all draped in a palette of soft whites that amplify the home's quiet elegance. The entry opens to a gracious central hall anchored by the hand-restored original staircase and balustrade. Beyond, a generous living room is separated from the dining room by the home's original--and fully functional--pocket doors, creating an effortless flow between intimate and open gathering spaces. At the rear of the house, the dining room--complete with a wood pellet stove-- opens onto the kitchen, powder room, and a deck overlooking the garden below. Upstairs, three sun-filled bedrooms and two full baths continue the home's serene sensibility; one bath features a soaking tub while the other offers a walk-in shower. Above it all, a substantial attic--already prepped for expansion--awaits its next chapter as a studio, guest quarters, or additional living space. Below, the sweetest garden apartment feels like a private retreat unto itself. Framed by lush greenery and accessed through its own separate gated entrance, the one-bedroom residence is bright, calm, and exceptionally well-appointed, complete with new appliances and its own laundry. A timeless, elegant, and effortless oasis in Hudson--steps from it all, while feeling entirely removed from the bustle beyond.

Rare waterfront opportunity on the Roeliff Jansen Kill / Green River! This prime .58-acre parcel in Hillsdale is the ultimate head-start for your dream home or weekend escape. Save thousands in development, the essential infrastructure is already completely in place, including an existing septic system, well, electric hookup, and a cleared house foundation ready for your vision. Imagine stepping out of your future back door right onto the water's edge. The property also features a detached one-car garage perfect for vehicle parking or secure storage, perennials throughout, and a charming, well-maintained gazebo for relaxing by the river. Located just minutes from Catamount Mountain Resort, Great Barrington, and the heart of Hillsdale, you get the perfect blend of tranquil waterfront living and Berkshire/Hudson Valley convenience.

There are houses that have been renovated, and then there are houses that have been thoughtfully stewarded. Occupying one of the most coveted stretches of Hudson's sought after 500 block of Warren Street, this exceptional brownstone is a masterclass in preservation—a home where extraordinary period architecture has been honored rather than replaced, and where every modern intervention feels quietly inevitable. For those drawn to historic homes, it is an increasingly rare offering. Throughout, original architectural details remain remarkably intact. Towering windows flood the interiors with natural light, while substantial moldings, deep baseboards, elaborate tin ceilings, oversized door casings, solid brass hardware, decorative cast-iron hinges, and weighty original doorknobs speak to a level of craftsmanship that simply isn't replicated today. Every room carries the quiet confidence of another era, lending the home an unmistakable sense of old-world glamour. Yet despite its reverence for the past, the house never feels like a museum. Instead, it possesses a sophistication that is difficult to manufacture—a layered, collected quality that suggests generations of thoughtful stewardship rather than a single decorating project. Rich textures, wallpapers, antique furnishings, and beautifully composed spaces create interiors that feel both deeply personal and effortlessly elegant. Every room has been edited with remarkable restraint from the area's local artisans and antique shops, allowing the architecture to remain the true focal point. The home unfolds across gracious entertaining spaces, intimate bedrooms, and beautifully appointed baths, each one carrying its own distinct character while remaining part of a cohesive whole. From richly paneled rooms and dramatic fireplaces to sunlit bedrooms, every space invites a slower pace and rewards careful attention. Beneath it all, a fully finished walkout lower level adds an entirely different dimension to daily living. Complete with a gym, generous mudroom, and dedicated dog wash, it offers the kind of practical luxury rarely found in historic townhouses, seamlessly connecting to the rear of the property. Outside, private rear parking—an invaluable amenity in Hudson—provides effortless convenience while preserving the home's elegant Warren Street presence. Situated on one of the city's most sought-after blocks, just moments from Hudson's renowned restaurants, galleries, boutiques, and cafés, the location is every bit as exceptional as the home itself. The 500 block of Warren Street has long been considered among the finest addresses in the city, where beautifully preserved nineteenth-century architecture forms one of the most distinguished streetscapes in the Hudson Valley. This is more than a beautifully renovated townhouse. It is a home for someone who appreciates the romance of period architecture, the quality of enduring craftsmanship, and the quiet luxury of spaces that have been assembled with patience. Homes of this caliber are exceptionally rare, and rarer still are those that feel as authentic, sophisticated, and timeless as this one.

Set on a beautifully landscaped parcel in one of the Hudson Valley's most sought-after river towns, this impeccably maintained home offers the ease of single-level living with timeless appeal. Built in 1991, the home features three bedrooms, two full baths, warm wood floors, a spacious two-car garage, and a full basement offering abundant storage and future possibilities. Recent mechanical updates, including a new central heating and air conditioning system, provide comfort and peace of mind for years to come. Outside, thoughtfully landscaped grounds create a private, park-like setting, while multiple patios offer inviting spaces for outdoor dining, entertaining, or simply enjoying the quiet beauty of the property. Ideally located just minutes from the Hudson River, the Amtrak station in Hudson, the vibrant village of Tivoli, and the celebrated restaurants, galleries, antique shops, and cultural destinations of both Hudson and Rhinebeck, this home offers the perfect balance of country living and convenience. Move-in-ready Hudson Valley retreat where comfort, charm, and location come together effortlessly.

All of the charm of an old farmhouse with none of the headaches. This c2005 build has sweeping views of the Catskill Mountains and loads of charm. Down a long, tree lined driveway, you're just two minutes from the historic hamlet of Germantown but you feel like you're in a world of your own. Peaceful, private and quiet, 336 Main Street truly offers the best of both worlds. Rocking chairs line the porch to watch the show as the sun sets over the mountains, a fire pit sits in the yard and hammocks hang in the trees. The eight acres have been beautifully landscaped with low maintenance, perennial gardens, and the rolling green lawn brings your eye to the mountains. A bucolic view, the only building in sight is a church steeple in the distance. Inside, you'll find high ceilings and walls of windows and glass doors to let the outside in-- the house was truly built to frame the view. The chef's kitchen is an absolute dream with a large island, a Sub Zero refrigerator, Viking gas range, two sinks and two dishwashers. A screened in porch runs the length of the house, perfect for entertaining, while there are quiet sitting rooms and an office tucked off to the side with dreamy views of the landscape and mountains. Upstairs there are three bedrooms, all ensuite. The primary has a private balcony & a large bathroom with a double vanity, a soaking tub and a large walk-in shower. The third floor has been built out with bunk beds, perfect for overflow or a place to park the kids. 336 Main is the ultimate in country living-- it leaves no stone unturned with its modern conveniences, old world charm, and those quintessential Hudson Valley pastoral views. Just 10m to Hudson & Amtrak, 15m to Rhinebeck village and 2h north of NYC.

This quintessential 19th century four bedroom farmhouse with a classic front porch, on over an acre of land, boasts impressive Catskill Mountain and sunset views. Only minutes from Hudson, the house, built in 1860, and now beautifully restored with wood floors throughout, has an expansive great room that includes the kitchen, a living area and a banquette for casual dining. The center island has a convenient prep sink and a breakfast bar for more seating. The room is perfect for cooking and entertaining with space for everyone. A wood stove warms the room and radiant heated floors in the banquette area keep feet warm in winter. Maple wood counter tops with mahogany trim are throughout the kitchen, a classic porcelain farm sink overlooks the garden, a subway tile backsplash and a high performance six burner gas stove for discerning cooks. Glass doors open to the bluestone patio and gardens, easily combining inside and out. A convenient pantry and laundry room off the kitchen offers ample storage. A separate dining room has space for formal dining and on the other side of the hallway, the light filled living room has a wood stove. The original staircase leads to the second floor with four bedrooms and two full baths. The primary bedroom has a vaulted ceiling, an office nook, a private dressing room and a wonderful en suite bathroom with a tiled walk-in shower and clawfoot soaking tub with views of the garden. A loft area can be opened in the primary bedroom creating an additional private space. Outside, the gardens have been meticulously tended with raised beds for vegetables, perennial plantings, native species, stunning gabion stone walls and a built-in fire pit for chilly evenings. An important historic heritage sugar maple tree graces the fenced back yard along with black walnut trees, ornamental cherry, hydrangea, forsythia, magnolia, mulberry, white pines and a lovely orchard of apples and peaches. The front porch wraps around the house and provides the ideal spot for relaxing with a summer breeze and wonderful distant views of the Catskills and vibrant sunsets. A vintage garage has space above that could be work or creative space. A well-maintained house with a standing seam metal roof on the main part of the house, new asphalt shingled roofs, a Buderus boiler, a new hot water heater, a water filtration system and an automatic generator for summer or winter storms. A beautiful country home in an ideal location on the historic Old Post Road that linked NYC to Albany. A short drive to historic Kinderhook Village, Art OMI sculpture park, Chatham Village, farmstands, restaurants, shops, Hudson and Amtrak. Just over two hours to NYC.

Greendale House is a rare Hudson River estate where historic character, graceful architecture, and breathtaking natural surroundings come together in one remarkable offering. Set within one of the Hudson Valley's most iconic landscapes, the property carries the quiet elegance and enduring presence of a true legacy home. Walking distance from Frederic Church's Olana and across the river from Thomas Cole's studio. You will recognize the landscape from their paintings. Around 2000, the home underwent a thoughtful renovation and the addition of the expansive screened porch, designed by architect Harry Van Dyke, best known for his association with the 1977 restoration of the Frick Collection on Fifth Avenue. The main residence features four bedrooms and three-and-a-half bathrooms, centered around a dramatic light-filled living room that feels both grand and inviting. Designed for effortless entertaining and comfortable daily living alike, the home opens to an expansive riverside verandah and screened porch overlooking the Hudson River — an idyllic setting for quiet mornings, summer dinners, and unforgettable sunsets. Rich with timeless appeal and a profound sense of place, Greendale House offers a rare opportunity to own a storied piece of Hudson Valley history. Tucked at the end of a dead-end road shared by only one other home, the property enjoys an exceptional level of privacy and tranquility along the Hudson River. Conservation easements in place.

A mixed use building in the heart of historic Hudson. This c1860 Federal style brick building is a fabulous investment with four beautifully updated apartments. Gut renovated in 2021, the building is completely turn key and has retained much of its historic charm. You’ll find a studio garden apartment in the lower level, a 2BR apartment on street level which could also be used as commercial/retail space, a 2BR apartment on the second floor, and a stunning duplex takes up the top two stories. Off-street parking for three cars in the rear, a fenced in yard planted with lovely perennials and a deck. With minimal maintenance and a healthy cap rate, 358 Warren is an incredible location, a wonderful opportunity for live/work or a pure investment play. Walking distance to Amtrak and in the heart of all that Hudson has to offer.

Originally built in the year 1800 on one the areas most historically significant roads lies this delightful antique farmhouse brimming with original details and charm. Perched above the road with its wrap around porch you are immediately transported to a simpler time where quality and beauty mattered. Further selling the vision, the periphery of your view is flanked with mature trees and one of two large barns providing a nostalgic aesthetic and endless opportunities. The barn closer to the home contains a garage for sheltered parking and the ability to create a guest house, work studio, private gym or anything you can dream up. In fact, there's room for all of those options within the same structure. A serene hilltop view in the distance beckons you to walk through the more than five and half acres of lawn, meadow and fruit trees to the second barn structure to continue dreaming up the possibilities. Currently this space is absolutely perfect to host outdoor dinner parties and gatherings with a bucolic view. The interior experience begins in the entry parlor, anchored by a traditional wood-burning stove. Original wide plank painted floors flow seamlessly into a spacious dining area bathed in natural light. Adjacent to this space, the modernized kitchen offers optimized storage solutions and updated appliances. The main level extends toward the rear of the residence, where the family room features stunning beamed ceilings that evoke a historical atmosphere. Completing this floor is a versatile adjoining room, ideally suited for guest accommodations or a home office and also conveniently hosts the laundry room. Up the wooden stairwell from the entry parlor three bedrooms and a bathroom surround the landing which has enough room to be its own library/reading space. The bedrooms are quite large for the era continuing this property's themes of charm, beauty and modern comfort. Just minutes away from Queechy Lake, where residents can enjoy access via an annual pass, its prime location offers easy reach to Chatham, Ghent, and Hudson on the New York side, while Great Barrington, West Stockbridge, and the Berkshires are equally accessible. Whether you are looking for a full-time residence or a perfect weekend retreat from NYC or Boston, this home serves as an ideal destination.

Set on just over three private acres in one of the Hudson Valley’s most sought-after towns, 249 Old Saw Mill is a house with extraordinary presence. Conceived as a contemporary interpretation of the vernacular barn structures that define the surrounding landscape, the home feels both grounded and transportive—architectural in form, yet deeply soulful in execution. Clad in charcoal-stained wood, the house reveals itself quietly. Inside, the mood shifts immediately: hand-troweled plaster walls, wide plank floors, reclaimed beams and millwork, stained poured concrete, antique doors, richly layered textiles, and globally sourced furnishings create interiors with unusual depth and warmth. Every surface feels considered. Every room carries a distinct sense of atmosphere. At the heart of the home is a dramatic open living, dining, and kitchen space anchored by a wood-burning fireplace and framed by expansive windows that draw in light throughout the day. The kitchen balances rustic materiality with modern function, while the adjoining covered porch extends living outdoors for long dinners and slow summer evenings. The layout offers three beautifully private en suite bedrooms, including two exceptional primary suites on the second floor, each with its own balcony overlooking the Catskills. Both are designed as true retreats, with open mountain views and spectacular sunset vistas that shift with the seasons. One suite is centered around a wood-burning fireplace, creating a particularly memorable sanctuary in colder months. Spa-like baths feature freestanding soaking tubs, vintage-inspired fixtures, and a tactile mix of stone, wood, and plaster. A lower-level media lounge adds an entirely different mood—moody, cocoon-like, and ideal for movie nights, work, or overflow guests. Practical features including a heated two-car garage, outdoor shower, and integrated firewood storage have been handled with the same thoughtful attention to design as the primary living spaces. Properties like this rarely come to market in Germantown. Equal parts architectural statement and deeply livable retreat, 249 Old Saw Mill offers something increasingly hard to find: a home with genuine soul. Just 5 minutes to the center of Germantown, 15 minutes to Hudson, and 20 minutes to Rhinebeck/Amtrak.

Welcome to 13149 NY 22, Canaan, NY 12029—a beautifully updated 3-bedroom, 1.5-bath ranch set on two open, usable acres. This home has been thoughtfully refreshed from top to bottom, offering true ease of living in a peaceful countryside setting. Step inside to find gleaming wood floors throughout, freshly painted interiors, and renovated bathrooms with crisp, modern finishes. The efficient single-level layout provides comfortable flow between the bright living spaces and the three well-sized bedrooms. Recent improvements include a brand-new roof, ensuring years of worry-free ownership. An attached two-car garage adds convenience and storage, while the expansive yard gives you plenty of room to garden, relax, or simply enjoy the quiet surroundings. Whether you're downsizing, seeking a weekend retreat, or looking for a low-maintenance full-time home, this ranch delivers a perfect blend of comfort, style, and practicality.

OPEN HOUSE on Saturday July 11 from 11AM to 1 PM Surrounded by rolling farmland, sweeping Catskill views, and spectacular sunsets, this historic Columbia County farmhouse offers the quintessential Hudson Valley retreat. Dating to the late 1700s or early 1800s, the home sits on 1.5 private acres along a quiet country road, bordered by more than 500 acres of adjoining pastureland where cows often graze. With no neighboring homes in sight, the setting offers a rare sense of privacy, beauty, and tranquility just 2¼ hours from New York City. Rich in character, the home retains many original architectural details, including exposed beams, wide-plank hardwood floors, and historic craftsmanship throughout. Thoughtful updates provide modern comfort while preserving the warmth and authenticity that make historic homes so special. The spacious country kitchen features a breakfast bar and adjoining dining area, while the inviting living room is anchored by a wood-burning fireplace. A first-floor primary bedroom includes a renovated en suite bath, and a flexible additional room can serve as a guest bedroom, office, library, or studio. Upstairs are two additional bedrooms and a large updated bath with a classic clawfoot soaking tub. Outside, enjoy quiet mornings on the rocking-chair front porch and evenings on the rear deck and patio overlooking open fields, distant Catskill peaks, and unforgettable sunsets. Mature trees and established landscaping frame the property, while a large garden with raised beds and drip irrigation offers ample space for growing flowers, herbs, and vegetables. Recent improvements include a Buderus boiler, an energy-efficient mini-split AC system, and a brand-new roof installed in 2026. A two-car garage barn provides additional storage and convenience. Ideally located near Hudson (15 min), Kinderhook (7 min), Chatham (15 min), Art Omi (5 min), Hawthorne Valley (20 min), farm stands, orchards, hiking trails, swimming holes, and skiing destinations, this special property captures the very best of Columbia County living.

If you can imagine living in a stunning mountain view shed among poetic gardens, Three Willows, an adorable Cape Cottage built in 1954 in the historic hamlet of Copake, NY, must be right for you. This wonderfully situated 2 bedroom 2.5 bathroom residence is located in the quaint hamlet center within walking distance to both the Copake General Store and the local yoga studio. The grounds of this lovely home are a garden paradise with waves of beautifully curated and native New York blooms for every week in season accompanied by a soul soothing, protected view of the Taconic mountain range at Bash Bish Falls and it's own deep, spring fed pond for a cold plunge beneath a giant, gentle willow amongst the birch and the bees. The kitchen boasts clean, white Viking appliances with a center island for the chef’s convenience with custom cabinetry and granite countertops with a dining area overlooking the back gardens and mountain views. The house is all electric and efficient with systems in place built to walk away and head to the city with ease. The two bedrooms are both en suite and very separate from one another, allowing for guests’ privacy. A home for all seasons with a park like setting for both gardening galore and cross country skiing across a wide expanse of snow covered hills for the winter buffs. The hamlet of Copake is a mini fertile valley contained within the wider Hudson Valley because it lies at the foot of the Mt. Washington State Forest with its magnificent Bash Bish waterfall flowing into the famed Roeliff Jansen Kill through the community and it’s contiguity of both Berkshires and Taconic ranges. Much like a little gem lettuce patch, this Copake hamlet boasts some of the very best alluvial soil and, therefore, produce in the region. Copake is definitely becoming an established flower farming community and this offering holds its own as a notable garden in the area.

Wildflower Hill is a rare and distinctive country retreat set behind a gated entrance on nearly six private acres in the gently rolling countryside of Southern Columbia County. Tucked behind mature trees and open lawns in the heart of Ancram, this four-bedroom, two-and-a-half-bath residence offers over 3,900 square feet of well-proportioned living space, where reclaimed wood beams, abundant natural light, a striking stone fireplace, and artful architectural details create a home of warmth, character, and timeless style. Designed for relaxed daily living, weekend entertaining, and four-season enjoyment, the interiors unfold through generous living and dining spaces with an easy connection to the outdoors. A large deck overlooks the grounds and extends the home beautifully for summer dinners, visiting guests, and quiet mornings in the country. Recent improvements include a brand-new boiler and brand-new septic system, offering immediate comfort, efficiency, and long-term peace of mind. Outside, the setting is both serene and full of charm. A koi pond, fruit trees, rolling lawns, fenced garden, and light-filled potting shed create a property that feels established, private, and deeply connected to the land. The acreage is beautiful and usable, with room to garden, entertain, explore, or simply enjoy the quiet rhythm of the seasons. Wildflower Hill balances privacy with exceptional access to the region's most beloved destinations. A short walk leads to the Ancram Little Store for coffee, breakfast, lunch, local cheeses, dairy, teas, and seasonal provisions. Farmers Wife is approximately six minutes away, Hillrock Estate Distillery is approximately nine minutes away, and Stissing House is about thirteen minutes away for celebrated farm-to-table dining. Millerton is roughly fifteen minutes away for restaurants, shopping, The Moviehouse, and Oblong Books, while Mashomack Polo Club, Catamount Mountain Resort, Hudson, Hillsdale, and the Berkshires are all within easy reach. New York City is approximately two hours away. Equally suited as a full-time residence, refined weekend retreat, or year-round lifestyle investment, Wildflower Hill captures the enduring appeal of Hudson Valley living with privacy, character, and a setting worth discovering.

On one of the most scenic country roads in the County, Willow Branch Farm, a 19th century farmhouse on over 53 acres has been transformed by the noted architect owner into a stunning property with Catskill views and sunsets. The Italianate three bedroom house is surrounded by a traditional English style landscape with a picturesque pond that delights the eye. Inside, 10 foot tall ceilings, wood floors and large windows bring in light and views throughout the day. Enter through original 19th century carved doors into the foyer. To the right, the expansive living room has a bay window to take in the view, floor to ceiling windows and a gas fireplace with an exceptional 19th century French Portoro black marble mantel. French doors open to the north porch. The spacious kitchen and dining room combine for the perfect place for cooking and entertaining. Custom rift and quartered white oak cabinetry hides a convenient coffee area and pantry space. A walnut topped island contains an induction cooktop and ample storage underneath. Top of the line appliances include a Sub-Zero refrigerator, a Bosch dishwasher, refrigerated drink drawers in the coffee station and two full size, convection wall ovens hidden behind a custom designed cabinet. A wall of floor to ceiling glass doors open to the west porch with dramatic views and sunsets throughout the year. Grass cloth walls, an English Wilton carpet and a 1940's French chandelier make for a very cozy library or ''Snug.'' The back hall, with a black basalt stone floor from Waterworks and antique 1920's pendant lights, leads to a large pantry and a separate laundry room with storage and a sink. The mud room, with double closets, hooks for hanging and a convenient bench, has a side door for easy access to and from the outside. The screened porch at the end of the hallway, which overlooks the pond and property, is ideal for summer relaxing and dining. A custom-built staircase with walnut bannister spindles and a hand tufted wool runner leads to the second floor. The primary bedroom has spectacular views facing west, a walk-in closet and en suite marble tiled bathroom. Off the hallway are two guest rooms, each with their own bathroom. The tower room with 16' ceilings is the ideal office or workspace. Bespoke details are throughout the home including St. Jude and Christopher Farr wallpaper in the bedrooms and first-floor half bath, all bathroom and kitchen fixtures and tile from Waterworks, many Vaughan and antique lighting fixtures, and all custom cabinetry. Outside, the barn has been redone with a new roof, concrete floor, plumbed for a bathroom, space for cars or workshop on the first floor and an impressive, high ceiling space on the second floor that can become guest space, extra living, studio, or work space. Beautifully restored original columns and decorative brackets line the north and west porches. Modern improvements include a new standing seam metal roof, buried power lines, energy efficient geo-thermal heating and cooling, new insulation, full house generator, Lutron lighting, motorized window shades, irrigation, sound, and security systems. The property is on two parcels. There is a separate 4-acre parcel of vacant land can be built on for a guest house, an, investment property, or sold. Just a few miles from the Hudson River and only minutes to the historic Village of Kinderhook with restaurants, bookstore, wine shop, Jack Shainman gallery, library, orchard, and the Empire Trail for walking or biking. Twenty minutes to Chatham Village. Just 30 minutes to Hudson's vibrant Warren Street and Amtrak. An easy drive to Albany Airport. Willow Branch Farm is the perfect blend of location, history, elegant design, and modern updates.

Experience idyllic country life and the best this area has to offer in this charming wood shingled house. Situated on two acres, this three-bedroom cape has an updated kitchen with stone counters which opens into the dining room. The spacious living room has a brick fireplace, built-in shelves and lovely French doors that open into a four-season heated sunroom with a vaulted ceiling and large windows that look out onto the property. Glass doors open onto a small porch that leads to the backyard. Enjoy days and evenings relaxing or entertaining outdoors with the fire pit, stone patio and the clawfoot tub converted into an outdoor shower. Upstairs are three bedrooms and a full bath. The large primary bedroom has double closets. Additional finished space adjacent to one bedroom could be used as an office, playroom or studio space. Finished space in the basement contains a cozy den, an exercise area, the laundry with a utility sink and a separate storage room. Two car garage opens directly into the kitchen and a convenient first floor half bath. EV/RV chargers. Just minutes to Beebe and Harvey Mountain State Forests with thousands of acres for hiking, many local ski options, Tanglewood, Berkshires cultural offerings and Chatham Village restaurants, shops and movie theater. A short drive to Hudson and Amtrak. Come visit this charming home in an ideal location!

Timeless farmhouse charm meets modern luxury in the heart of Old Chatham. Set on 1.4 picturesque acres, this beautifully renovated 1875 home has been thoughtfully restored from top to bottom, blending historic character with contemporary comfort. Inside, you’ll find sun-filled living spaces, gleaming hardwood floors, a gourmet kitchen featuring a Wolf range, Bosch appliances, quartz countertops, and custom solid wood cabinetry, plus three spacious bedrooms, 2.5 designer baths, and an oversized dressing room. Outside, enjoy a brand-new wraparound porch overlooking peaceful grounds that invite morning coffee, evening cocktails, and everything in between. Whether you’re searching for a full-time residence or the perfect Hudson Valley weekend escape, this move-in-ready home offers the rare combination of classic farmhouse warmth, exceptional craftsmanship, and effortless living in one of Columbia County’s most charming villages.

Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat. The grand living room, anchored by a wood-burning fireplace and lined with a wall of windows, frames views of the grounds and invites natural light throughout the day. The custom-designed kitchen marries modern function with period detail, while the sun-drenched dining room—with exposures on two sides—provides an elegant setting for intimate gatherings. A deep, screened porch spans the length of the north wing, overlooking the gardens and flowing lawns. On the main floor, a serene en suite bedroom and a private guest suite with sitting room and separate entrance offer flexible accommodations. Upstairs, two charming bedrooms share a beautifully appointed bath. A short stroll through lush gardens and across a second private drive leads to the stunning, two-story post-and-beam barn. Currently curated as an antique store, the structure offers an expansive lofted studio and is zoned for commercial or residential use—ideal for a gallery, guesthouse, or creative workspace. This rare, historic compound offers a peaceful, pastoral lifestyle just over two hours from Manhattan—a perfect fusion of old-world charm and modern-day potential. Tucked into the rolling foothills of the Berkshires, Hillsdale is one of the Hudson Valley’s most coveted enclaves—quietly elegant, unspoiled, and deeply rooted in charm. Just over two hours from Manhattan, it offers the ideal blend of refined rural living and easy access to the region’s most sophisticated cultural and culinary experiences. Here, sweeping vistas, winding country roads, and historic farmhouses coexist with curated farm-to-table restaurants, chic design shops, and proximity to world-class destinations like Hudson, Great Barrington, and Tanglewood. Hillsdale is home to Catamount Mountain Resort for year-round recreation, from skiing to ziplining, and just minutes from Copake Lake, private golf clubs, and nature preserves. Discreet, low-key, and deeply authentic, Hillsdale attracts those seeking serenity without sacrifice—an elevated escape that feels worlds away, yet entirely within reach. Hillsdale is fast becoming one of one of Columbia County’s most desirable investment destinations. Just over two hours from Manhattan, this historic town offers a rare combination of timeless charm and smart, long-term value. As boutique hospitality, curated design, and high-end food culture continue to expand nearby—in Hudson, Great Barrington, and Chatham—Hillsdale has quietly emerged as a prime location for luxury second homes and discreet development. With a strong track record of appreciation and zoning that allows for flexibility, it's an ideal market for those looking to balance lifestyle with strategic growth Hillsdale offers proximity to a refined network of private clubs, golf courses, and recreational resorts that define the elevated Hudson Valley lifestyle. You're just minutes from the exclusive Copake Country Club, private lakefront communities, and the slopes of Catamount Mountain, offering four-season access to skiing, hiking, and ziplining. Paired with nearby spas, organic farms, and award-winning restaurants, Hillsdale is a magnet for those who appreciate privacy, taste, and a quietly luxurious pace—without sacrificing access to world-class experiences.

4 Union St offers a fabulous location, incredible views and comfortable living just steps from the Amtrak station. The c1830 townhouse on desirable lower Union Street is an early example of the federal style in a town renowned for its architecture. Inside, the home has been wonderfully modernized while still remaining true to its historic roots. Walls have been opened on the ground floor to create a large and light filled open space, the living room and kitchen connected. An old brick mantle grounds the living room, and a large center island grounds the kitchen. The ceilings are high, the windows are large, the wide old growth pine floorboards are original. The second floor has also been reimagined, opened up into a single, large bedroom designed with gorgeous views of the Hudson River taking center stage. The third floor at the home’s highest elevation has a large open landing and two small rooms at the house’s southern end. Currently used as offices, both have windows overlooking the Hudson Athens lighthouse, an incredibly rare and coveted vantage point, and the Catskill Mountains beyond the river. One of the best views that this charming rivertown has to offer. The lower level of the home has been converted to additional living space with a bedroom and full bath It walks out to a lovely and sizable tiered courtyard with expertly laid stonework and perennial plantings. A sun filled spot when the weather turns. 4 Union is all buttoned up, steps to the Amtrak and all that Hudson has to offer.

For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is experiencing a renaissance and is dotted with new restorations of gorgeous farmhouses and new builds, adding a fresh dynamic to the area. This site is perfect for any health and wellness guru looking to recreate life on a farm for the benefit of the community, for an hotelier or hospitality group to develop an Upstate experience compound or simply to restore a piece of American architectural history to become a beautiful 4 bedroom 2 bathroom residence in the heart of the Craryville to Hillsdale corridor and all the conveniences that entails. The house sits high on a bluff overlooking West End Road and below the dale is a large former dairy barn with a metal roof and cattle stalls. There is a detached garage with an efficiency apartment over it behind the house with the opportunity to plant a crop in an adjacent waiting field. Three large parcels make up this offering and the residence has the opportunity to sell the remaining two while maintaining 100 acres for an impressive estate.