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$895,000

Welcome to The Chancery Building, an 1885 Queen Anne Victorian rising three stories behind a corner turret with conical roof and finial, its cross-gabled roofline and projecting bays adding to the architectural presence. Just a few blocks from Warren Street on a peaceful tree-lined street in Hudson's historic district, the property is fully leased and currently home to six commercial tenants generating steady income. Originally constructed for residential living, the building has transitioned to mixed-use while retaining many of its original historic details. Three separate street-level entrances, parking for six cars, and a flexible layout make it equally suited to continued leasing, an owner-operator's business, a live/work arrangement, or a return to full residential use. It's as adaptable as it is architecturally distinct.

6 Beds ⋅ 2 Baths ⋅ 202622353 MLS

Welcome to The Chancery Building, an 1885 Queen Anne Victorian rising three stories behind a corner turret with conical roof and finial, its cross-gabled roofline and projecting bays adding to the architectural presence. Just a few blocks from Warren Street on a peaceful tree-lined street in Hudson's historic district, the property is fully leased and currently home to six commercial tenants generating steady income. Originally constructed for residential living, the building has transitioned to mixed-use while retaining many of its original historic details. Three separate street-level entrances, parking for six cars, and a flexible layout make it equally suited to continued leasing, an owner-operator's business, a live/work arrangement, or a return to full residential use. It's as adaptable as it is architecturally distinct.

437 E Allen Street

$825,000

Set on 4.5 rolling acres, this stunning 1870s Ghent farmhouse is the kind of find you don't stumble on twice: 19th-century character paired with light, layout, and land that's nearly impossible to come by today. A front porch with hand-carved gingerbread brackets and delicate scrollwork announces the home's Second Empire pedigree before you've even reached the door, craftsmanship that's stood the test of 150-plus years. Step inside to wide-plank pine floors flowing through sun-drenched common rooms with soaring ceilings and original moldings. A library with a wood-burning fireplace and built-in shelving makes the perfect quiet escape. The sunny country kitchen, with open shelving and generous counters, spills into a vaulted dining room, ideal for entertaining. French doors lead out to a generous brick patio, tucked beneath a white pergola and bordered by garden beds bursting with color, an idyllic spot for long dinners outdoors, with open meadow and rolling hills unfolding just beyond. Outside is where this property truly sings: mature shade trees frame the expansive lawn, while the open meadow offers uninterrupted views across Hudson Valley hills, a backdrop that transforms with every season. A detached two-car garage adds storage and workspace without touching the property's historic footprint. Ideally located to enjoy all the Hudson Valley has to offer, with Hawthorne Valley Farm and The Campus nearby and Hudson's shops, restaurants, and Amtrak access just 15 minutes away, this home puts the best of the region within easy reach. It's a rare chance to own a piece of Hudson Valley history: move-in ready, brimming with character, and set on land that feels frozen in time.

4 Beds ⋅ 3 Baths ⋅ 202622257 MLS

Set on 4.5 rolling acres, this stunning 1870s Ghent farmhouse is the kind of find you don't stumble on twice: 19th-century character paired with light, layout, and land that's nearly impossible to come by today. A front porch with hand-carved gingerbread brackets and delicate scrollwork announces the home's Second Empire pedigree before you've even reached the door, craftsmanship that's stood the test of 150-plus years. Step inside to wide-plank pine floors flowing through sun-drenched common rooms with soaring ceilings and original moldings. A library with a wood-burning fireplace and built-in shelving makes the perfect quiet escape. The sunny country kitchen, with open shelving and generous counters, spills into a vaulted dining room, ideal for entertaining. French doors lead out to a generous brick patio, tucked beneath a white pergola and bordered by garden beds bursting with color, an idyllic spot for long dinners outdoors, with open meadow and rolling hills unfolding just beyond. Outside is where this property truly sings: mature shade trees frame the expansive lawn, while the open meadow offers uninterrupted views across Hudson Valley hills, a backdrop that transforms with every season. A detached two-car garage adds storage and workspace without touching the property's historic footprint. Ideally located to enjoy all the Hudson Valley has to offer, with Hawthorne Valley Farm and The Campus nearby and Hudson's shops, restaurants, and Amtrak access just 15 minutes away, this home puts the best of the region within easy reach. It's a rare chance to own a piece of Hudson Valley history: move-in ready, brimming with character, and set on land that feels frozen in time.

333 County Road 9

$343,000

On a nice country road in Stuyvesant you will find this one owner ranch which has been lovingly maintained thruout the years. Yes updates are needed but the roof is approx 10 years old, and the furnace and oil tank were new in 2022. There are three bedrooms, a den, large great room with fireplace, living room, eat in kitchen and a bath and a half. Laundry is in the half bath. Then you have a deep one car garage plus another garage out back for your ''toys''. Screened in porch, large workshop and storage space over the garage. Come take a look this one will not last long!

3 Beds ⋅ 2 Baths ⋅ 202622088 MLS

On a nice country road in Stuyvesant you will find this one owner ranch which has been lovingly maintained thruout the years. Yes updates are needed but the roof is approx 10 years old, and the furnace and oil tank were new in 2022. There are three bedrooms, a den, large great room with fireplace, living room, eat in kitchen and a bath and a half. Laundry is in the half bath. Then you have a deep one car garage plus another garage out back for your ''toys''. Screened in porch, large workshop and storage space over the garage. Come take a look this one will not last long!

457 Sharptown Road

$650,000

Escape to your own private retreat where lake living, outdoor adventure, and timeless country charm come together! Just steps from scenic Copake Lake, this property offers access to one of Columbia County's premier recreational destinations. Copake Country Club features an 18-hole championship golf course and year-round dining. Conveniently located between Hudson and Great Barrington, and just a short drive to Catamount Mountain Resort, the area offers four-season recreation, with the tranquility of your own beautifully landscaped 4.66 acre setting. Inside, this home is rich with warmth and timeless character. The inviting eat-in kitchen features a breakfast bar, abundant cabinetry, and a pantry, creating a functional space that will delight any home chef. Just beyond, the dining area flows seamlessly into the spacious living room where a cozy wood-burning stove, custom built-in bookcases, and decorative wood trim create a welcoming atmosphere for everyday living and entertaining. The bright, glass enclosed sunroom provides the perfect spot for morning coffee, reading, or simply relaxing, while a handily located half bath completes the main level. Upstairs, you'll find three comfortable bedrooms and two full bathrooms. Gleaming hardwood floors span throughout both levels, and an abundance of natural light fills the home, enhancing the attractive appeal. Outside, the detached two-car garage includes ample room for a workshop, lawn equipment and recreational storage. The second floor of the garage offers endless possibilities as an artist's studio, home office, fitness room, or hobby space. . Unwind beneath the covered patio and enjoy the serenity of your surroundings. Whether you're searching for a full-time residence or the perfect weekend getaway, this exceptional property offers the ideal balance of privacy, recreation, and convenience--just minutes from the Taconic State Parkway and only 2.5 hours from New York City.

3 Beds ⋅ 3 Baths ⋅ 202621523 MLS

Escape to your own private retreat where lake living, outdoor adventure, and timeless country charm come together! Just steps from scenic Copake Lake, this property offers access to one of Columbia County's premier recreational destinations. Copake Country Club features an 18-hole championship golf course and year-round dining. Conveniently located between Hudson and Great Barrington, and just a short drive to Catamount Mountain Resort, the area offers four-season recreation, with the tranquility of your own beautifully landscaped 4.66 acre setting. Inside, this home is rich with warmth and timeless character. The inviting eat-in kitchen features a breakfast bar, abundant cabinetry, and a pantry, creating a functional space that will delight any home chef. Just beyond, the dining area flows seamlessly into the spacious living room where a cozy wood-burning stove, custom built-in bookcases, and decorative wood trim create a welcoming atmosphere for everyday living and entertaining. The bright, glass enclosed sunroom provides the perfect spot for morning coffee, reading, or simply relaxing, while a handily located half bath completes the main level. Upstairs, you'll find three comfortable bedrooms and two full bathrooms. Gleaming hardwood floors span throughout both levels, and an abundance of natural light fills the home, enhancing the attractive appeal. Outside, the detached two-car garage includes ample room for a workshop, lawn equipment and recreational storage. The second floor of the garage offers endless possibilities as an artist's studio, home office, fitness room, or hobby space. . Unwind beneath the covered patio and enjoy the serenity of your surroundings. Whether you're searching for a full-time residence or the perfect weekend getaway, this exceptional property offers the ideal balance of privacy, recreation, and convenience--just minutes from the Taconic State Parkway and only 2.5 hours from New York City.

3493 County Road 7

$549,000

Live right in the center of Hudson's vibrant arts scene, acclaimed restaurants, boutique shopping, historic architecture, farmers markets, and year-round cultural events become part of your everyday life. Perfectly situated at the top of Warren Street, this historic 1960's updated ranch places you within walking distance of everything that has made Hudson one of the most sought-after destinations, including a convenient 15-minute walk to Amtrak for easy access to New York City.This charming two-bedroom, one-bath home has been thoughtfully renovated while maintaining its classic character. Enjoy seasonal Catskill Mountain views from the inviting front porch, relax on the screened three-season porch, or unwind in the included hot tub overlooking the spacious backyard. Whether you're enjoying your morning coffee on the porch or entertaining family and friends outdoors, this home offers the perfect balance of vibrant city living and comfortable indoor-outdoor enjoyment.Inside, you'll find a beautifully remodeled kitchen, refinished original hardwood floors, a renovated full bath with radiant heated floors, and a cozy wood-burning fireplace. The finished lower level provides exceptional flexibility with a home office, game room, and additional space ideal for guests, hobbies, or a potential third bedroom.Extensive recent improvements include a new roof, newly paved driveway, attractive stone retaining wall with staircase, new concrete front sidewalk and steps, new rear concrete patio, repointed chimney, new garage door, and a security system. The attached garage is currently used as a workshop with storage for bicycles, e-bikes, and outdoor equipment.Complete with natural gas, public water and sewer, and an unbeatable walkable location, this turnkey home is ideal as a full-time residence, weekend retreat, or future investment in one of the Hudson Valley's most desirable communities.Only a few hrs to NYC

2 Beds ⋅ 1 Baths ⋅ 202620692 MLS

Live right in the center of Hudson's vibrant arts scene, acclaimed restaurants, boutique shopping, historic architecture, farmers markets, and year-round cultural events become part of your everyday life. Perfectly situated at the top of Warren Street, this historic 1960's updated ranch places you within walking distance of everything that has made Hudson one of the most sought-after destinations, including a convenient 15-minute walk to Amtrak for easy access to New York City.This charming two-bedroom, one-bath home has been thoughtfully renovated while maintaining its classic character. Enjoy seasonal Catskill Mountain views from the inviting front porch, relax on the screened three-season porch, or unwind in the included hot tub overlooking the spacious backyard. Whether you're enjoying your morning coffee on the porch or entertaining family and friends outdoors, this home offers the perfect balance of vibrant city living and comfortable indoor-outdoor enjoyment.Inside, you'll find a beautifully remodeled kitchen, refinished original hardwood floors, a renovated full bath with radiant heated floors, and a cozy wood-burning fireplace. The finished lower level provides exceptional flexibility with a home office, game room, and additional space ideal for guests, hobbies, or a potential third bedroom.Extensive recent improvements include a new roof, newly paved driveway, attractive stone retaining wall with staircase, new concrete front sidewalk and steps, new rear concrete patio, repointed chimney, new garage door, and a security system. The attached garage is currently used as a workshop with storage for bicycles, e-bikes, and outdoor equipment.Complete with natural gas, public water and sewer, and an unbeatable walkable location, this turnkey home is ideal as a full-time residence, weekend retreat, or future investment in one of the Hudson Valley's most desirable communities.Only a few hrs to NYC

84 Worth Avenue

$859,000

''The Lodge at Blue Hill'' Nestled on 2.88 private acres along scenic Blue Hill Road, this exceptional 3-bedroom, 3-bath log home offers breathtaking, unobstructed Catskill Mountain views, spectacular sunsets, and a peaceful Hudson Valley setting. Providing the perfect balance of privacy, natural beauty, and accessibility.Built in 2005 and meticulously maintained, the home showcases soaring cathedral ceilings, cherry hardwood floors, and a warm propane fireplace framed by custom 8-foot built-in bookcases. Large windows throughout capture stunning mountain vistas, while thoughtfully selected finishes--including Rejuvenation lighting, Casablanca ceiling fans, custom wood blinds, quartz countertops, a farmhouse sink, and clay tile flooring--add timeless character and comfort.The open-concept kitchen, dining, and living areas create an inviting atmosphere for entertaining or everyday living. Each bedroom features its own en-suite bath, including a luxurious upstairs primary suite complete with a California Closet dressing room, blackout shades, and a private deck overlooking the Catskills.Outdoor living is equally impressive with a 42-foot covered front porch perfect for sunset views and a 16x16 screened porch surrounded by nature. The finished lower level adds approximately 1,000 square feet of living space, featuring a 7-seat home theater with Bose surround sound, a large utility/laundry room, and a soundproof guest suite with private bath.Modern amenities include a Navien on-demand furnace, central air conditioning, whole-house generator, and owner-owned propane tanks. Additional improvements include an oversized heated 2-car garage and a powered 16x16 workshop shed.This turnkey Hudson Valley retreat combines quality craftsmanship, modern convenience, and stunning natural surroundings, all within easy reach of Hudson, Germantown, Olana, the Rip Van Winkle Bridge, the Skywalk, and just two hours from New York City.

3 Beds ⋅ 3 Baths ⋅ 202620356 MLS

''The Lodge at Blue Hill'' Nestled on 2.88 private acres along scenic Blue Hill Road, this exceptional 3-bedroom, 3-bath log home offers breathtaking, unobstructed Catskill Mountain views, spectacular sunsets, and a peaceful Hudson Valley setting. Providing the perfect balance of privacy, natural beauty, and accessibility.Built in 2005 and meticulously maintained, the home showcases soaring cathedral ceilings, cherry hardwood floors, and a warm propane fireplace framed by custom 8-foot built-in bookcases. Large windows throughout capture stunning mountain vistas, while thoughtfully selected finishes--including Rejuvenation lighting, Casablanca ceiling fans, custom wood blinds, quartz countertops, a farmhouse sink, and clay tile flooring--add timeless character and comfort.The open-concept kitchen, dining, and living areas create an inviting atmosphere for entertaining or everyday living. Each bedroom features its own en-suite bath, including a luxurious upstairs primary suite complete with a California Closet dressing room, blackout shades, and a private deck overlooking the Catskills.Outdoor living is equally impressive with a 42-foot covered front porch perfect for sunset views and a 16x16 screened porch surrounded by nature. The finished lower level adds approximately 1,000 square feet of living space, featuring a 7-seat home theater with Bose surround sound, a large utility/laundry room, and a soundproof guest suite with private bath.Modern amenities include a Navien on-demand furnace, central air conditioning, whole-house generator, and owner-owned propane tanks. Additional improvements include an oversized heated 2-car garage and a powered 16x16 workshop shed.This turnkey Hudson Valley retreat combines quality craftsmanship, modern convenience, and stunning natural surroundings, all within easy reach of Hudson, Germantown, Olana, the Rip Van Winkle Bridge, the Skywalk, and just two hours from New York City.

1374 Blue Hill Road

$785,000

Welcome to Hastings House, a circa 1880s residence set high on the eastern hill of Worth Avenue in the heart of Hudson. This sophisticated 3-bedroom, 2.5-bath home features wide plank original hardwood floors, abundant natural light, and well-proportioned interiors that combine warmth with understated elegance. The galley kitchen opens both to the dining room and to a bright sunroom, creating an inviting flow for everyday living and entertaining. Updated Anderson windows bring light deep into the principal rooms, and mini split systems provide heating and cooling throughout. Mature trees and established plantings surround the property, offering privacy and a serene setting just steps from Hudson's vibrant center. The fully refurbished two-story carriage house adds 750 square feet of flexible living space, complete with a newly installed wood burning stove and air conditioning. Whether used as a studio, guest retreat, office, or creative workspace, it is among the property's most distinctive and versatile features, carrying its own history as a former schoolhouse. A covered front porch frames rooftop views of Hudson and the Catskill Mountains beyond, and a private fenced backyard with patio and fire pit offers a quiet outdoor retreat. Private off-street parking for two vehicles is accessed via the rear alley, with additional parking available out front. Located just steps from Warren Street, Hastings House offers the best of Hudson living, with easy access to Rivertown Lodge, Hudson Roastery, Union Street Brewing, Lil' Debs Oasis, and Cafe Mutton. Amtrak service to New York City is within easy walking distance.

3 Beds ⋅ 3 Baths ⋅ 202618692 MLS

Welcome to Hastings House, a circa 1880s residence set high on the eastern hill of Worth Avenue in the heart of Hudson. This sophisticated 3-bedroom, 2.5-bath home features wide plank original hardwood floors, abundant natural light, and well-proportioned interiors that combine warmth with understated elegance. The galley kitchen opens both to the dining room and to a bright sunroom, creating an inviting flow for everyday living and entertaining. Updated Anderson windows bring light deep into the principal rooms, and mini split systems provide heating and cooling throughout. Mature trees and established plantings surround the property, offering privacy and a serene setting just steps from Hudson's vibrant center. The fully refurbished two-story carriage house adds 750 square feet of flexible living space, complete with a newly installed wood burning stove and air conditioning. Whether used as a studio, guest retreat, office, or creative workspace, it is among the property's most distinctive and versatile features, carrying its own history as a former schoolhouse. A covered front porch frames rooftop views of Hudson and the Catskill Mountains beyond, and a private fenced backyard with patio and fire pit offers a quiet outdoor retreat. Private off-street parking for two vehicles is accessed via the rear alley, with additional parking available out front. Located just steps from Warren Street, Hastings House offers the best of Hudson living, with easy access to Rivertown Lodge, Hudson Roastery, Union Street Brewing, Lil' Debs Oasis, and Cafe Mutton. Amtrak service to New York City is within easy walking distance.

16 Worth Avenue

$1,599,000

Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6 spacious bedrooms and 5 bathrooms, including an ideal in-law suite or private apartment setup for extended family, guests, or potential additional living space. The heart of the home is the incredible chef's kitchen--thoughtfully designed with generous work space, high-end finishes, and the kind of layout any chef or aspiring cook would absolutely love. Step outside to enjoy the wrap around deck overlooking the built-in saltwater pool and serene grounds, creating the perfect setting for entertaining or simply relaxing into total privacy. A 3-car garage plus an additional garage beneath the residence provide plenty of room for tractor, hobbies, and storage. This one-of-a-kind Chatham retreat combines elegant country living with modern convenience, all just a short drive to the charming villages, restaurants, and culture the Hudson Valley is known for.

6 Beds ⋅ 5 Baths ⋅ 202617663 MLS

Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6 spacious bedrooms and 5 bathrooms, including an ideal in-law suite or private apartment setup for extended family, guests, or potential additional living space. The heart of the home is the incredible chef's kitchen--thoughtfully designed with generous work space, high-end finishes, and the kind of layout any chef or aspiring cook would absolutely love. Step outside to enjoy the wrap around deck overlooking the built-in saltwater pool and serene grounds, creating the perfect setting for entertaining or simply relaxing into total privacy. A 3-car garage plus an additional garage beneath the residence provide plenty of room for tractor, hobbies, and storage. This one-of-a-kind Chatham retreat combines elegant country living with modern convenience, all just a short drive to the charming villages, restaurants, and culture the Hudson Valley is known for.

20 Stony Knoll

$1,585,000

Welcome to Chicory Hill House, a unique designer home set at the end of a long private driveway on 20 beautiful acres located in Columbia County, prime Hudson Valley. The property features pastoral views, a year-round creek, and a small waterfall woven into the landscape. Following an extensive high-end renovation and infrastructure overhaul, the original 1985 contemporary has been transformed with remarkable craftsmanship and modern systems. The home features wide plank white oak floors, a floor-to-ceiling fluted marble wood-burning fireplace, stone countertops, handcrafted Zellige tile, and spa-like baths. An expansive cedar deck, hot tub, outdoor shower, solar panels, and a flexible lower level with a wood-burning stove and room for additional bedrooms complete the property. Just five minutes to Chatham, under twenty to Hudson's Warren Street, and a little over two hours to New York City.

3 Beds ⋅ 2 Baths ⋅ 202617064 MLS

Welcome to Chicory Hill House, a unique designer home set at the end of a long private driveway on 20 beautiful acres located in Columbia County, prime Hudson Valley. The property features pastoral views, a year-round creek, and a small waterfall woven into the landscape. Following an extensive high-end renovation and infrastructure overhaul, the original 1985 contemporary has been transformed with remarkable craftsmanship and modern systems. The home features wide plank white oak floors, a floor-to-ceiling fluted marble wood-burning fireplace, stone countertops, handcrafted Zellige tile, and spa-like baths. An expansive cedar deck, hot tub, outdoor shower, solar panels, and a flexible lower level with a wood-burning stove and room for additional bedrooms complete the property. Just five minutes to Chatham, under twenty to Hudson's Warren Street, and a little over two hours to New York City.

41 Chicory Lane

$365,000

Welcome to Hawthorne Cottage, a circa 1900 updated residence on Main Street in the heart of Philmont's historic district, set on a sloping lot with a stone wall and partial woodland in one of Columbia County's most authentic small villages. The home has been fully renovated. Open shelving and curated details create inviting living spaces full of warmth and character. The kitchen includes butcher block counters, a herringbone tile backsplash, stainless steel appliances, and striking navy cabinetry accented by brushed brass hardware. New laminate floors run through every room and bathrooms have been updated. The cozy layout spans 1,392 square feet, with a half bath on the first floor and three bedrooms and a full bath above. The unfinished walk-out basement adds approximately 360 square feet of flexible additional space, and is ready to be finished to your own specifications. Ideal as a home office, guest quarters, home gym, or creative studio. A brand new heating system completes a renovation that leaves little to do but move in. Philmont is a small Columbia County village with a growing creative community and a genuine historic fabric. Hawthorne Valley School and its beloved farm store are nearby, as is the High Falls Conservation Area, where trails wind through hemlock ravines to Columbia County's highest waterfall. Local 111 and other village favorites are close at hand for dining. Hudson's Warren Street galleries, restaurants, and Amtrak station are eighteen minutes away, Chatham is fifteen minutes, and New York City is two and a half hours by car. The farm stands, hiking trails, and country roads that define life in this part of the valley are all within easy reach.

3 Beds ⋅ 2 Baths ⋅ 202616964 MLS

Welcome to Hawthorne Cottage, a circa 1900 updated residence on Main Street in the heart of Philmont's historic district, set on a sloping lot with a stone wall and partial woodland in one of Columbia County's most authentic small villages. The home has been fully renovated. Open shelving and curated details create inviting living spaces full of warmth and character. The kitchen includes butcher block counters, a herringbone tile backsplash, stainless steel appliances, and striking navy cabinetry accented by brushed brass hardware. New laminate floors run through every room and bathrooms have been updated. The cozy layout spans 1,392 square feet, with a half bath on the first floor and three bedrooms and a full bath above. The unfinished walk-out basement adds approximately 360 square feet of flexible additional space, and is ready to be finished to your own specifications. Ideal as a home office, guest quarters, home gym, or creative studio. A brand new heating system completes a renovation that leaves little to do but move in. Philmont is a small Columbia County village with a growing creative community and a genuine historic fabric. Hawthorne Valley School and its beloved farm store are nearby, as is the High Falls Conservation Area, where trails wind through hemlock ravines to Columbia County's highest waterfall. Local 111 and other village favorites are close at hand for dining. Hudson's Warren Street galleries, restaurants, and Amtrak station are eighteen minutes away, Chatham is fifteen minutes, and New York City is two and a half hours by car. The farm stands, hiking trails, and country roads that define life in this part of the valley are all within easy reach.

152 Main Street

$599,000

Move right in! Enjoy the best of both worlds at 22 Van Winkle Road -- a sophisticated retreat tucked away in the serene ''Silent Zone'' of Hudson's sought-after Academy Hill community. This spacious 4-bedroom plus den, 3 full bath townhome offers stunning Hudson River and mountain views, blending peaceful suburban privacy with convenient access to the vibrant energy of nearby Warren Street's acclaimed dining, breweries, art galleries, and boutiques. Bring your own vision and personal touches to this generously sized home featuring two fireplaces, a relaxing jet bath, finished basement and two private balconies and deck overlooking the Catskill and Berkshire mountains. A scenic walking path with breathtaking views adds to the tranquil setting. Whether you are seeking a stylish primary residence, weekend escape, or investment opportunity, the low-maintenance lifestyle allows more time to enjoy the nearby Greenport Conservation area or hop on Amtrak for an easy trip to NYC. Discover modern convenience, natural beauty, and Hudson Valley charm in a community that truly offers it all.

4 Beds ⋅ 3 Baths ⋅ 202615994 MLS

Move right in! Enjoy the best of both worlds at 22 Van Winkle Road -- a sophisticated retreat tucked away in the serene ''Silent Zone'' of Hudson's sought-after Academy Hill community. This spacious 4-bedroom plus den, 3 full bath townhome offers stunning Hudson River and mountain views, blending peaceful suburban privacy with convenient access to the vibrant energy of nearby Warren Street's acclaimed dining, breweries, art galleries, and boutiques. Bring your own vision and personal touches to this generously sized home featuring two fireplaces, a relaxing jet bath, finished basement and two private balconies and deck overlooking the Catskill and Berkshire mountains. A scenic walking path with breathtaking views adds to the tranquil setting. Whether you are seeking a stylish primary residence, weekend escape, or investment opportunity, the low-maintenance lifestyle allows more time to enjoy the nearby Greenport Conservation area or hop on Amtrak for an easy trip to NYC. Discover modern convenience, natural beauty, and Hudson Valley charm in a community that truly offers it all.

22 Van Winkle Road

$12,750,000

DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling hayfields with formal gardens, offering unobstructed vistas to the Catskill Mountains, dramatic sunsets and a lifestyle rooted in beauty, craftmanship and serenity. A tree lined drive leads to the stately 4,900 SF Greek Revival manor home where classic architecture meets stately elegance. Adjacent sits a heated three-car garage complete with a 1.200 SF second floor office apartment and a spacious parking court. Entering the home, you will experience some of the finest craftmanship, curated lighting and architectural detailing. The entrance foyer, with a grand staircase to the second floor, is flanked by a Mahogany paneled library and a sunlit breakfast room. Further, is the formal salon and dining room which extend onto a deep ''southern-style'' covered sitting porch with views of the far-reaching meadows and Catskill range beyond. The chef's kitchen is designed for effortless entertaining while remaining intimate enough for everyday living. Just beyond the kitchen is a service entrance with access to a private one-bedroom apartment above. Upstairs, the primary en-suite is joined by two additional en-suite bedrooms and a richly paneled home office which connects to a third-floor studio with panoramic views. The finished lower level includes a gym, a fully appointed laundry, a second pantry, a cedar lined walk-in closet and the home's mechanical systems. Every floor is serviced by an in-home elevator.

4 Beds ⋅ 6 Baths ⋅ 202614668 MLS

DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling hayfields with formal gardens, offering unobstructed vistas to the Catskill Mountains, dramatic sunsets and a lifestyle rooted in beauty, craftmanship and serenity. A tree lined drive leads to the stately 4,900 SF Greek Revival manor home where classic architecture meets stately elegance. Adjacent sits a heated three-car garage complete with a 1.200 SF second floor office apartment and a spacious parking court. Entering the home, you will experience some of the finest craftmanship, curated lighting and architectural detailing. The entrance foyer, with a grand staircase to the second floor, is flanked by a Mahogany paneled library and a sunlit breakfast room. Further, is the formal salon and dining room which extend onto a deep ''southern-style'' covered sitting porch with views of the far-reaching meadows and Catskill range beyond. The chef's kitchen is designed for effortless entertaining while remaining intimate enough for everyday living. Just beyond the kitchen is a service entrance with access to a private one-bedroom apartment above. Upstairs, the primary en-suite is joined by two additional en-suite bedrooms and a richly paneled home office which connects to a third-floor studio with panoramic views. The finished lower level includes a gym, a fully appointed laundry, a second pantry, a cedar lined walk-in closet and the home's mechanical systems. Every floor is serviced by an in-home elevator.

199 Eichybush Road

$625,000

A 1780 Colonial farmhouse in the heart of Columbia County! updated mechanicals, character and charm throughout, zoned mix use on an over 1 acre corner lot with a 20X12 and a 16X12 outbuildings ideal for an antique shop, art gallery or home business. Main house is 3 bedrooms, 2 full baths, updated kitchen, sun room, roof deck, patio, the landscaping is amazing with a little tlc after a harsh winter- koi pond, waterfall, gazebo. A must see charm and character throughout.

3 Beds ⋅ 2 Baths ⋅ 202613626 MLS

A 1780 Colonial farmhouse in the heart of Columbia County! updated mechanicals, character and charm throughout, zoned mix use on an over 1 acre corner lot with a 20X12 and a 16X12 outbuildings ideal for an antique shop, art gallery or home business. Main house is 3 bedrooms, 2 full baths, updated kitchen, sun room, roof deck, patio, the landscaping is amazing with a little tlc after a harsh winter- koi pond, waterfall, gazebo. A must see charm and character throughout.

46 State Route 23

$299,000

1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High visibility on main NY-MA artery. Fantastic location for studio or professional spaces incl massage, acupuncture, attorney, chiropractor, accountant. Centrally located Columbia/Albany/Berkshire counties. Fully rented: 1st flr tenant 1100 dollars/mth; 2nd flr tenant 1750 dollars/mth. 24-48hr notice required to show. As a matter of brkrage policy, any co-op brokr comm, if offered, is payable solely and exclusively to a lic re brkr/brkrage company.

3 Beds ⋅ 2 Baths ⋅ 202613554 MLS

1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High visibility on main NY-MA artery. Fantastic location for studio or professional spaces incl massage, acupuncture, attorney, chiropractor, accountant. Centrally located Columbia/Albany/Berkshire counties. Fully rented: 1st flr tenant 1100 dollars/mth; 2nd flr tenant 1750 dollars/mth. 24-48hr notice required to show. As a matter of brkrage policy, any co-op brokr comm, if offered, is payable solely and exclusively to a lic re brkr/brkrage company.

1135 New York 295

$109,888

Step back in time with this historic colonial home built in 1857, a rare opportunity to own a true piece of American history predating the Civil War. Rich with character and original charm, this property offers the perfect canvas for someone who appreciates historic homes and their timeless craftsmanship With thoughtful rehabilitation, this property presents significant upside potential, with an estimated after-repair value much, much higher. Conveniently located just minutes from the rail station, it combines historic charm with modern accessibility for commuters. Inside, you'll find three bedrooms and two baths, along with beautiful wood floors and two classic fireplaces that evoke the warmth and elegance of another era. The home also features a traditional summer kitchen, a charming reminder of 19th-century living that adds both historical significance and unique character.

3 Beds ⋅ 2 Baths ⋅ 202526860 MLS

Step back in time with this historic colonial home built in 1857, a rare opportunity to own a true piece of American history predating the Civil War. Rich with character and original charm, this property offers the perfect canvas for someone who appreciates historic homes and their timeless craftsmanship With thoughtful rehabilitation, this property presents significant upside potential, with an estimated after-repair value much, much higher. Conveniently located just minutes from the rail station, it combines historic charm with modern accessibility for commuters. Inside, you'll find three bedrooms and two baths, along with beautiful wood floors and two classic fireplaces that evoke the warmth and elegance of another era. The home also features a traditional summer kitchen, a charming reminder of 19th-century living that adds both historical significance and unique character.

45 County Route 26A

$719,000

Welcome to your private retreat in the Taconic Hills School District! Set on 8 serene acres, this beautifully renovated home offers the perfect balance of comfort, style, and versatility. With 5 bedrooms and 4 full baths, there's plenty of space for family, friends, or guests. The sun-drenched great room is the heart of the home, featuring vaulted ceilings and dual stone fireplaces that create a warm, inviting atmosphere. The updated kitchen is both functional and stylish, complete with new cabinetry, butcher block countertops, and a spacious walk-in pantry. The finished lower level offers 2 additional bedrooms, a full bath, a family room, and a walkout, making it an ideal setup for guests, in-laws, or even rental potential. An oversized 2-car garage provides ample storage, while the open, peaceful grounds invite you to enjoy nature and outdoor living. Perfectly located—just 20 minutes to Catamount Ski Resort, Hudson, and Lake Taghkanic, and only an hour to Hunter and Windham—this property is ideal as a primary residence, weekend escape, or a high-potential short-term rental. Don't miss the chance to make this versatile and beautifully updated property yours!

5 Beds ⋅ 4 Baths ⋅ 202518112 MLS

Welcome to your private retreat in the Taconic Hills School District! Set on 8 serene acres, this beautifully renovated home offers the perfect balance of comfort, style, and versatility. With 5 bedrooms and 4 full baths, there's plenty of space for family, friends, or guests. The sun-drenched great room is the heart of the home, featuring vaulted ceilings and dual stone fireplaces that create a warm, inviting atmosphere. The updated kitchen is both functional and stylish, complete with new cabinetry, butcher block countertops, and a spacious walk-in pantry. The finished lower level offers 2 additional bedrooms, a full bath, a family room, and a walkout, making it an ideal setup for guests, in-laws, or even rental potential. An oversized 2-car garage provides ample storage, while the open, peaceful grounds invite you to enjoy nature and outdoor living. Perfectly located—just 20 minutes to Catamount Ski Resort, Hudson, and Lake Taghkanic, and only an hour to Hunter and Windham—this property is ideal as a primary residence, weekend escape, or a high-potential short-term rental. Don't miss the chance to make this versatile and beautifully updated property yours!

100 Schnackenberg Road