luxury houses for sale Columbia County, United States

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.

The Philmont Collection presents a rare opportunity to acquire a 36-unit multifamily portfolio encompassing nine buildings across seven tax lots in the heart of Philmont's National Register Historic District. Spanning approximately 26,606 square feet, the collection combines immediate scale, strong in-place cash flow, historic character, and meaningful redevelopment potential within one of the Hudson Valley's most closely watched village investment markets. Strategically clustered within a few walkable blocks of one another, the portfolio includes seven stabilized income-producing assets together with two historic value-add buildings, creating a level of operational efficiency and market presence rarely available in a single acquisition. The collection comprises 36 residential units with 48 bedrooms and 28 bathrooms, offering a diverse mix of apartments and duplex residences that support broad tenant appeal and stable occupancy. The stabilized core portfolio is projected to generate approximately $350,000-$360,000 in annual NOI, providing attractive current returns while preserving opportunities for future value enhancement. Ownership has invested substantially throughout the portfolio in capital improvements, infrastructure upgrades, and operational efficiencies designed to improve long-term performance and reduce operating costs. A cornerstone asset within the collection, 62 Main Street has undergone extensive renovation, including updated residential units, restored facade improvements, enhanced insulation, conversion from central oil heat to individual electric systems, and renovated bathrooms. These improvements, together with portfolio-wide upgrades, position the collection as a well-maintained and professionally operated investment. Current operations utilize the DoorLoop management platform for leasing, maintenance coordination, rent collection, tenant communication, applications, and screening, facilitating a seamless transition for future ownership. The portfolio also includes the historic front and rear buildings at 7 Church Street, presenting a compelling redevelopment opportunity within Philmont's historic core. Subject to purchaser verification and approvals, these buildings may be eligible for substantial federal and New York State historic rehabilitation tax incentives, creating a potentially powerful avenue for future value creation and income growth. Long appreciated for its architectural character and strategic location, Philmont continues to attract investors, entrepreneurs, artists, and designers drawn to its affordability relative to neighboring Hudson, its historic building stock, and its ongoing revitalization. Significant public and private investment, adaptive reuse projects, and preservation initiatives continue to strengthen the village's long-term trajectory. Ideally situated just minutes from the Taconic State Parkway and approximately fifteen minutes from Hudson and Amtrak service to New York City, the portfolio enjoys convenient access to the Berkshires, Hawthorne Valley Farm, Art Omi, hiking trails, skiing, boating, waterfalls, acclaimed dining destinations, and the cultural amenities that define the Hudson Valley lifestyle. Combining immediate income, operational scale, historic character, redevelopment potential, and an extraordinary village-wide footprint, The Philmont Collection represents a truly uncommon opportunity to establish a meaningful position within a growing and increasingly recognized Hudson Valley market. MLS information reflects the primary parcel only. Seller reserves the right to sell individual assets or subsets of assets separately from the portfolio offering. Complete financial statements, rent rolls, parcel information, and supporting materials are available upon request. Annual tax amount reflects the entire portfolio.

A very early Hudson home built c1790 likely in the Federal style, 102-104 North Fifth Street was converted into a striking Italianate at the turn of the 19th century. The beautifully ornamental porch is a fabulous place to take in the charming block, and the striking facade is adorned with bracketed cornices typical of the Italianate style. Just blocks to Warren Street, Hudson’s main drag, the neighborhood is residential and quiet. You have a large backyard with a patio, a 6ft fence for privacy, and lovely & mature plantings. Inside, the proportions are as elegant as the exterior, with high ceilings and wide spaces. The kitchen is open, grounded by a center island, and you’ll find large common spaces and small quiet nooks. An office sits at the back of the house, and you’ll find a gas fireplace clad in brick in the living room. A magnificent curved staircase has its original banister, a work of art, and upstairs you’ll find three bedrooms. The primary is ensuite, lovely and large with a soaking tub, separate shower, and double vanity. There is off street parking lined with cobblestone walls, and the double lot offers wonderful outdoor space. A wonderfully quiet corner just a 3m walk to the center of town and all that Hudson has to offer with its renowned restaurants & antique shops, and just up the road from the Amtrak train station. 102-104 North Fifth is completely turn key & done to a wonderfully high standard, just 2.5h north of NYC.

Newly completed and set on 11.7 private acres in the heart of Hillsdale, this architect-designed 4-bedroom, 4-bath modernist residence combines striking contemporary architecture with sweeping pastoral and mountain views in every direction. Arriving via a long private driveway, rolling lawns and open fields unfold toward a home defined by bold geometric forms, expansive walls of glass, and a seamless connection to the surrounding landscape. Just minutes from the Hamlet of Hillsdale, Catamount Mountain Resort, Great Barrington, and Hudson, the property offers a rare balance of architectural refinement, privacy, and access to the region’s most desirable destinations. The residence is centered around a dramatic great room with a soaring 20-foot vaulted ceiling and a wood-burning fireplace clad in richly toned chestnut marble. Floor-to-ceiling glass and oversized Arcadia sliding doors dissolve the boundary between interior and exterior, opening onto more than 540 square feet of covered outdoor living space designed for year-round entertaining and relaxed outdoor living. Throughout the home, natural light shifts across clean architectural lines and warm materiality, reinforcing a strong connection between structure and landscape. The kitchen serves as both a design centerpiece and functional workspace, featuring custom walnut cabinetry crafted by a Brooklyn cabinetmaker, integrated Fisher & Paykel and Bosch appliances, an oversized monolithic island, and a 48-inch double-oven gas range. A fully equipped butler’s pantry and bar area provides additional prep space, storage, second dishwasher, and additional refrigeration, allowing the main kitchen to remain clean and open for entertaining. The primary suite is a private retreat with vaulted ceilings, a custom dressing room, and a spa-like bath finished in dramatic Calacatta Violetta marble, featuring a soaking tub, oversized shower, and fluted glass steel-framed doors. Upstairs, a second ensuite bedroom offers its own walk-in closet and marble-appointed bath, complemented by an additional guest bedroom suite. A versatile fourth bedroom on the main level provides flexible use as a guest suite, office, media room, or wellness space with direct access to the outdoor terrace. Designed for high-performance modern living, the home includes spray foam insulation, high-performance windows, forced-air heating and central air conditioning, on-demand hot water, Lutron lighting controls, remote-access thermostats, generator hookup readiness, and a detached heated 26' x 26' two-car garage. Located just minutes from Catamount Mountain Resort and within easy reach of Great Barrington and Hudson, the home places owners at the center of the Hudson Valley and Berkshires lifestyle. Days might begin with coffee overlooking the fields, followed by a visit to the Saturday farmers market, skiing at Catamount, or hiking nearby trails. Afternoons can be spent browsing Hudson’s celebrated design and antique shops or exploring the galleries, bookstores, and restaurants of Great Barrington. Evenings bring performances at local theaters and live music venues, or a quiet return home as the light settles across the landscape. The setting balances architectural refinement, outdoor recreation, and cultural depth in equal measure. A rare expression of contemporary Hudson Valley living, where architecture, light, and landscape are held in perfect balance. An adjoining 6.73-acre parcel is also available for purchase, offering the opportunity to expand the estate or create a private family compound. (listing agent has a financial interest in the property)

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.

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.

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.

Some addresses simply carry weight and 514 Warren Street sits at the very heart of Hudson's celebrated mile-long main corridor -- the cultural and commercial spine of one of the Hudson Valley's most sought-after cities. This is not just a property. It is a front-row seat to everything that makes Hudson extraordinary. Warren Street has stood at the center of Hudson since the city's founding in 1783, when a group of Quaker whalers and merchants laid out the grid that still defines the city today. The buildings that line it have been called one of the richest dictionaries of architectural history in New York State -- and 514 Warren places you squarely within that legacy. Step outside and you are surrounded by the best Hudson has to offer. The mile-long business district centered on Warren Street boasts dozens of first-tier antique and home furnishing shops, along with an eclectic mix of art galleries, restaurants, and performance spaces. Neighbors at this stretch of Warren include acclaimed galleries, destination restaurants, and boutiques that draw visitors from New York City and beyond every weekend. The Hudson Amtrak station -- offering a direct two-hour connection to Manhattan -- is just blocks away, making this address equally compelling for full-time residents and savvy second-home buyers. Hudson is a small, supply-constrained market with persistent demand driven by second-home buyers, remote workers, and downstate transplants. Inventory remains limited, particularly for move-in-ready historic properties near Warren Street. In short: properties here don't wait. In Hudson's market, authenticity and condition are far more important value drivers than square footage alone -- and a Warren Street address is the very definition of authentic. Whether you envision a sophisticated private residence, a mixed-use live-work property, or a premium commercial space, 514 Warren Street offers the platform to realize it. Hudson's zoning along Warren Street has historically supported a flexible blend of retail, gallery, hospitality, and residential use -- giving the next owner genuine optionality. Well-priced properties on Warren Street continue to attract strong interest , and in a city where scarcity is a permanent feature of the landscape, the window to act is always shorter than it appears.

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!

OPEN HOUSE Sunday, June 28th from 11 AM - 1 PM 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 home 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.

A modern country home inspired by the farmhouses of the Hudson Valley. Taconic Creek Road is tucked away amongst rolling hills and large surrounding parcels, on a beautiful dead end road with just a few lovely houses. The palette is restrained but luxurious with a thoughtful layout and custom design details. Spanning 2,100 square feet, you’ll find lime washed walls with stunning depth of color, custom millwork and wideboard wood flooring that adds warmth to the space. The main living area is anchored by the open kitchen, with Tundra Gray marble counters, an English farmhouse sink, custom inset cabinetry and paneled appliances. A deVOL pendant hangs over the kitchen table. The sitting area is lined with custom built bookshelves and there are large, deep windows lining the room. They face out into the garden, and french doors at the center take you onto the patio. There is storage and a built in bench at the entry for your boots and bags, and a lovely bath on the main level with Noguchi pendant lights. Upstairs, a light filled sitting room walks out to a screened in porch, and there are three bedrooms spread out across the floor. The primary suite is large with a stunning picture window, an office/walk-in closet and a gorgeous bathroom. You’ll find a walk-in-shower and soaking tub with views of the surrounding treetops. Two other bedrooms share the third bathroom off the hall. There is an extensive list of upgrades that includes a new roof, HVAC and septic, and the current owners buried the electrical lines to the house. A large pool is surrounded by lilacs and hedges, private and peaceful, and there is a garage for parking. Taconic Creek Road offers a rare level of calm and sophistication just 15m to Hudson and Amtrak and under 2.5h north of NYC.

Welcome to Cricket Hill Farm-a circa 1949 country home set against sweeping Catskill Mountain views, this home offers the rare opportunity to create your own Hudson Valley retreat. Privately sited with a beautiful front lawn, mature trees, and a gorgeous bluestone patio designed for outdoor dining and summer evenings, the setting alone is worth the drive. Inside, the three-bedroom, two-bath home is filled with character, including hardwood floors throughout and a wood-burning fireplace that anchors the living space. The seller has already gutted the kitchen, opening the space and creating a true blank canvas for the next owner to design and renovate to their taste. The bathrooms are also ready for updating, making this an ideal opportunity for someone with vision looking to bring new life to a well-loved home. A detached one-car garage adds convenience, while the mountain views and established landscape create the kind of setting that's hard to replicate. An authentic Hudson Valley fixer with soul, views, and endless possibility.

A unique live/work opportunity just outside Hudson proper. Once the Claverack Rail Station, the workshop and galleries at 33 Maple are a chance to own a piece of Columbia County history. The property is made up of three historic buildings dating back to 1870 and varying in size and function. The site is pastoral, 3.5 acres of rolling green grass under a canopy of large maples. You’ll spot the old rail bed out back. For the last 35 years the property has served as a center for world-class craftsmanship in architectural restoration and antique furniture conservation, first under Sotheby’s and now STAIR Galleries. Exceptionally well cared for, utilities have been run underground and the mechanicals kept up-to-date throughout their decades-long tenure.The main building is large, spanning 8,000 square feet with high ceilings and large, open spaces. It has a standing seam metal roof and the loading dock can accommodate a large truck. Next door the 1,000 square foot ticket office is charming in its many historic details, the original ticket counter and built-in bench seating have been saved and restored. It most recently served as a jeweler’s workshop, while the final building, once a waystation for coal and hay sales and currently fitted as a  small private personal gym, serves as a medical office spanning two floors with a kitchen. The site is comprised of four distinct parcels and over 10,000 square feet of space. Perfect for an artist or craftsperson, a production studio or workshop, or to build your dream home, the possibilities are endless. You are in the heart of the Hudson Valley just 10m to Amtrak and 2h to NYC.

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a welcoming foyer, a serene bedroom suite, and an elegant formal living room.Upstairs, the master suite is a haven of sophistication, complete with a stone fireplace and ample space for relaxation. Two additional guest bedrooms share a Jack and Jill bathroom, providing comfort and privacy for friends.The finished lower level is dedicated to leisure and repose, crafted with the ultimate goal of relaxation in mind. Here, in this tranquil setting, you'll find the peace and privacy you desire, all within a home that exudes charm and character.

Escape the hustle 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. Offering 6 to 9 beautifully appointed bedrooms, including three full suites, five bathrooms, multiple fireplaces, and both a fully stocked eat-in kitchen and a formal dining room, the estate blends elegance and comfort with ease. Recreation and relaxation abound, with a spacious in-ground pool, a serene pond, and direct access to miles of hiking and snowshoeing trails, including those of the Old Chatham Hunt Club. Indoors, guests enjoy a full gym, a game and entertainment room with arcade favorites, a home theater, a library of hundreds of books, and a finished attic, while a 4,500-square-foot barn with foosball, ping pong, and bar space provides additional room for gatherings and events. Perfect for weddings, anniversaries, family celebrations, and private retreats, Bellavista also offers access to private chefs, caterers, and event planning support, with every detail—from fiber-optic internet and full-house generators to weekly pool and grounds maintenance—thoughtfully attended to. Since 2011, the estate has been a successful luxury rental for vacations and retreats, equally suited to private full- or part-time residence, a hybrid work-from-home escape, or an unforgettable destination getaway. Just minutes from Chatham, Hudson, and Kinderhook, and a short drive to Lenox, Stockbridge, and Great Barrington, the estate is surrounded by farm-to-table dining, art galleries, organic markets, and the renowned Crandell Theater, with easy access via the Taconic Parkway or I-87 from New York City, I-90 from Boston, Amtrak to Penn Station, or Albany International Airport.

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.

Designer Nick Spain reimagined this early c1800 home, sited on the historic river road connecting Hudson and Stuyvesant. Formally known as The Garrett Stickles House, recalling the prominent family that built this historic home, a four year renovation under Spain’s artful eye kept the fabulous original details intact— its wideboard floors, leaded glass sidelights, and classic six-over-six windows, juxtaposing them with modern finishes like the floor-to-ceiling glass wall in the kitchen overlooking the pastoral yard, a large concrete sink basin in the master bath & a sleek woodstove tucked into an alcove in the dining room. The center hall residence is classic in its proportions and exciting in its design, you’ll find a wood burning fireplace in the living room & a small office tucked into the back. There are two upstairs wings— one houses a guest room and the other an additional bedroom and the primary suite. The bathroom is adorned with unlaquered brass fixtures from Waterworks, handmade tiles and a double vanity. The extensive renovation went well beyond aesthetics— the chimneys were rebuilt, the roof, windows (top of the line Marvins) & septic are new, the electrical service upgraded and there is a full house generator. You’re just 15m to Hudson proper and Amtrak, as well as the charming & historical village of Kinderhook. The Garrett Stickles House has been published in Wallpaper and Upstate House, it is a fully turn-key home that both design lovers and old house aficionados will enjoy. Just 2.5h north of NYC.

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.

Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining. A tranquil sun-room provides a versatile space, ideal for a home office or a quiet retreat. Down a private hall, the sleeping wing awaits. The primary suite is a true haven, featuring a second fireplace, a charming window seat for reading, a large walk-in closet, and an en-suite bath. Two additional well-proportioned bedrooms with ample closet space share a pristine hall bathroom. A generous two-car attached garage and a full basement offer abundant storage and convenience right off the main entry.Outside, the 8.3-acre grounds are a serene blend of manicured lawn, wild meadow, and mature plantings. The location is truly stellar: less than five minutes to Catamount Mountain Resort for year-round adventure, and just moments from

Experience the perfect blend of historic settlement and pastoral tranquility, enhanced by the abounding Valatie Kill on the property in the coveted hamlet of North Chatham. This is a rare opportunity to own a home in a nationally recognized Historic District, where 18th-century charm meets the modern desire for space and serenity. This very sweet 3200 square foot 4 bedroom 2.5 bathroom home comes to the market for the first time in nearly 50 years and preserves its colloquial charm throughout. Featuring an eat in kitchen and gracious dining room, it is a wonderful gathering spot. A downstairs primary en suite bedroom is coupled with a living room with fireplace and a seasonal sunroom with a herringbone patterned red brick floor, creating a heart and hearth with plenty of rooms to congregate. Add to the main house a two story barn and a one car garage making this offering a workable home for many folks. North Chatham NY is a close knit community and a collection of perfectly charming 18th and 19th century residences of architectural significance surrounded entirely by equestrian estates and arcadian farmland. Once a trolley stop on the Albany-Hudson line developed in 1795 and conveniently situated between the villages of Kinderhook and Chatham NY and 2.5 hours from NYC, this offering inhabits the essential Upstate farm to table lifestyle with fabulous restaurants and shops nearby. This community is a haven for those seeking a slower pace without sacrificing connectivity.

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.

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.