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Welcome to this beautifully maintained 1910 American Foursquare, one of Hudson's historic Boulevard homes. Lovingly cared for by the same owner for more than 30 years, this legal two-family residence is currently enjoyed as a spacious single-family home w/ an in-law apt. on the second floor - features that make it an outstanding owner-occupied multigenerational residence or income-producing property.Offering approximately 1,912 square feet of living space on the first and second floors, and appx. 400 sq ft. on 3rd floor. This classic home showcases beautifully refinished original hardwood floors, high ceilings, rich original woodwork, and timeless architectural character throughout. The main level features spacious living and gathering rooms, two generous bedrooms, a remodeled handicap-accessible full bathroom, and an updated kitchen complete with new appliances, a center island, abundant cabinetry, new luxury vinyl flooring, and direct access to the laundry room which includes pantry storage, new washer and dryer, and a rear entrance.The second floor offers two additional bedrooms, an updated full bathroom, a large kitchen, and a cozy den with a private entrance, providing exceptional flexibility for owner occupancy, extended family, or rental use. The partially finished third floor features separate electrical service, beautiful original wide-plank wood floors, full insulation, and an egress window, offering excellent potential for additional living space, a home office, studio, or guest suite.Recent improvements include a new roof , Buderus Boiler, updated windows, plumbing, recent interior painting and masonry and much more.

4 Beds ⋅ 2 Baths ⋅ 202621074 MLS

Welcome to this beautifully maintained 1910 American Foursquare, one of Hudson's historic Boulevard homes. Lovingly cared for by the same owner for more than 30 years, this legal two-family residence is currently enjoyed as a spacious single-family home w/ an in-law apt. on the second floor - features that make it an outstanding owner-occupied multigenerational residence or income-producing property.Offering approximately 1,912 square feet of living space on the first and second floors, and appx. 400 sq ft. on 3rd floor. This classic home showcases beautifully refinished original hardwood floors, high ceilings, rich original woodwork, and timeless architectural character throughout. The main level features spacious living and gathering rooms, two generous bedrooms, a remodeled handicap-accessible full bathroom, and an updated kitchen complete with new appliances, a center island, abundant cabinetry, new luxury vinyl flooring, and direct access to the laundry room which includes pantry storage, new washer and dryer, and a rear entrance.The second floor offers two additional bedrooms, an updated full bathroom, a large kitchen, and a cozy den with a private entrance, providing exceptional flexibility for owner occupancy, extended family, or rental use. The partially finished third floor features separate electrical service, beautiful original wide-plank wood floors, full insulation, and an egress window, offering excellent potential for additional living space, a home office, studio, or guest suite.Recent improvements include a new roof , Buderus Boiler, updated windows, plumbing, recent interior painting and masonry and much more.

10 Oakwood Boulevard, Hudson

$725,000

Discover the perfect blend of privacy, space, and versatility with this custom-built 2,400 sq. ft. home nestled on 5.5 scenic acres. Featuring 3 bedrooms, 1 bath, and soaring cathedral ceilings, this one-of-a-kind property offers comfortable living with exceptional indoor and outdoor amenities. Step outside to your own private retreat, complete with an inground pool, pool house, greenhouse with a newer metal roof, basketball court, and beautifully landscaped grounds. Enjoy the beauty of mature plum, apple, pear, and mimosa trees, stunning Japanese maples, and a charming grape arbor that creates a peaceful setting for relaxing or entertaining. Ideal for car enthusiasts, hobbyists, or small business owners, the property includes an attached 4-car garage plus a separate insulated building with electric that accommodates up to three additional vehicles. The upper level offers a dedicated home office and a second finished room perfect for a gym, art studio, guest space, hobby room, or private retreat. Whether you're dreaming of a hobby farm, home-based business, workshop, studio, or simply a peaceful country escape with room to grow, this exceptional property offers endless possibilities. The combination of acreage, multiple outbuildings, abundant storage, recreation, and mature landscaping makes this a rare opportunity. Conveniently located while offering the privacy and tranquility of country living, this is more than a home--it's a lifestyle. Schedule your private showing today and experience everything this remarkable property has to offer.

3 Beds ⋅ 1 Baths ⋅ 202620821 MLS

Discover the perfect blend of privacy, space, and versatility with this custom-built 2,400 sq. ft. home nestled on 5.5 scenic acres. Featuring 3 bedrooms, 1 bath, and soaring cathedral ceilings, this one-of-a-kind property offers comfortable living with exceptional indoor and outdoor amenities. Step outside to your own private retreat, complete with an inground pool, pool house, greenhouse with a newer metal roof, basketball court, and beautifully landscaped grounds. Enjoy the beauty of mature plum, apple, pear, and mimosa trees, stunning Japanese maples, and a charming grape arbor that creates a peaceful setting for relaxing or entertaining. Ideal for car enthusiasts, hobbyists, or small business owners, the property includes an attached 4-car garage plus a separate insulated building with electric that accommodates up to three additional vehicles. The upper level offers a dedicated home office and a second finished room perfect for a gym, art studio, guest space, hobby room, or private retreat. Whether you're dreaming of a hobby farm, home-based business, workshop, studio, or simply a peaceful country escape with room to grow, this exceptional property offers endless possibilities. The combination of acreage, multiple outbuildings, abundant storage, recreation, and mature landscaping makes this a rare opportunity. Conveniently located while offering the privacy and tranquility of country living, this is more than a home--it's a lifestyle. Schedule your private showing today and experience everything this remarkable property has to offer.

25 Hawthorne Hill Road, Chatham

$525,000

Welcome home to this sweet, impeccably maintained property nestled on 4.5 acres of beautifully manicured rolling lawns. Move-in ready and full of charm, this inviting home offers the perfect balance of comfort, privacy, and opportunity. The second floor features three spacious bedrooms, a versatile office or sitting room, convenient second-floor laundry, and a walk-in closet in the primary bedroom. On chilly winter evenings, gather around the cozy fireplace in the open living room. The quaint country kitchen opens seamlessly to the dining and living areas, creating an ideal space for entertaining while offering peaceful views of the backyard. Step outside onto the back deck and enjoy your own private oasis, where a gently flowing creek provides the perfect place to relax and cool off while surrounded by nature. Thoughtful updates include Castle Windows with a transferable lifetime warranty and a new roof with a LeafFilter gutter protection system, offering peace of mind for years to come. A truly exceptional bonus is the massive approximately 65' x 35' detached two-car garage with an attached storage building, workshop, retail space, or small business area. Whether you're an entrepreneur, hobbyist, collector, or simply need abundant storage, the possibilities are endless. Conveniently located with easy access to the Berkshires, Hudson, Chatham, Albany, the Taconic State Parkway, I-90, and I-87, this property combines peaceful country living with exceptional accessibility. Come experience everything this unique property has to offer--you may just find your forever home.

3 Beds ⋅ 2 Baths ⋅ 202620781 MLS

Welcome home to this sweet, impeccably maintained property nestled on 4.5 acres of beautifully manicured rolling lawns. Move-in ready and full of charm, this inviting home offers the perfect balance of comfort, privacy, and opportunity. The second floor features three spacious bedrooms, a versatile office or sitting room, convenient second-floor laundry, and a walk-in closet in the primary bedroom. On chilly winter evenings, gather around the cozy fireplace in the open living room. The quaint country kitchen opens seamlessly to the dining and living areas, creating an ideal space for entertaining while offering peaceful views of the backyard. Step outside onto the back deck and enjoy your own private oasis, where a gently flowing creek provides the perfect place to relax and cool off while surrounded by nature. Thoughtful updates include Castle Windows with a transferable lifetime warranty and a new roof with a LeafFilter gutter protection system, offering peace of mind for years to come. A truly exceptional bonus is the massive approximately 65' x 35' detached two-car garage with an attached storage building, workshop, retail space, or small business area. Whether you're an entrepreneur, hobbyist, collector, or simply need abundant storage, the possibilities are endless. Conveniently located with easy access to the Berkshires, Hudson, Chatham, Albany, the Taconic State Parkway, I-90, and I-87, this property combines peaceful country living with exceptional accessibility. Come experience everything this unique property has to offer--you may just find your forever home.

1188 U.S. 20, New Lebanon

$529,000

MLS Public Remarks: ''Our Little Oasis'' is how the owners describe this thoughtfully updated 1960s ranch in the heart of Hudson. Set back from Worth Avenue, the home offers a private backyard with subtle outdoor lighting, Catskill Mountain sunsets, and plenty of space for gardening and entertaining. Relax at the end of the day with a glass of wine in the hot tub and enjoy the peaceful surroundings. The interior features two bedrooms, a beautifully remodeled kitchen with granite countertops and new appliances, a renovated full bathroom with radiant heated flooring, refinished original hardwood floors, and a cozy wood-burning fireplace. The finished lower level offers flexible space for a home office, game room, guests, hobbies, or a potential third bedroom. EXTENSIVE RECENT IMPROVEMENTS INCLUDE: New roof; newly paved driveway; new stone retaining wall with staircase; new concrete front sidewalk and steps; new rear concrete patio; repointed chimney; new garage door; remodeled kitchen; renovated bathroom with radiant heated flooring; refinished hardwood floors; and a security system. Additional amenities include a three-season porch, hot tub, attached garage currently used as a workshop and storage area, natural gas, and public water and sewer. Located near the top of Warren Street, the home is within walking distance of Hudson's restaurants, galleries, shops, farmers markets, and cultural attractions. Approximately five minutes by car to the Hudson Amtrak station.

2 Beds ⋅ 1 Baths ⋅ 202620692 MLS

MLS Public Remarks: ''Our Little Oasis'' is how the owners describe this thoughtfully updated 1960s ranch in the heart of Hudson. Set back from Worth Avenue, the home offers a private backyard with subtle outdoor lighting, Catskill Mountain sunsets, and plenty of space for gardening and entertaining. Relax at the end of the day with a glass of wine in the hot tub and enjoy the peaceful surroundings. The interior features two bedrooms, a beautifully remodeled kitchen with granite countertops and new appliances, a renovated full bathroom with radiant heated flooring, refinished original hardwood floors, and a cozy wood-burning fireplace. The finished lower level offers flexible space for a home office, game room, guests, hobbies, or a potential third bedroom. EXTENSIVE RECENT IMPROVEMENTS INCLUDE: New roof; newly paved driveway; new stone retaining wall with staircase; new concrete front sidewalk and steps; new rear concrete patio; repointed chimney; new garage door; remodeled kitchen; renovated bathroom with radiant heated flooring; refinished hardwood floors; and a security system. Additional amenities include a three-season porch, hot tub, attached garage currently used as a workshop and storage area, natural gas, and public water and sewer. Located near the top of Warren Street, the home is within walking distance of Hudson's restaurants, galleries, shops, farmers markets, and cultural attractions. Approximately five minutes by car to the Hudson Amtrak station.

84 Worth Avenue, Hudson

$645,000

Explore the possibilities with this 22 acre property featuring a 2,000-square-foot Cape with 3 bedrooms, 2 full baths, hardwood floors, and an attached 2-car garage. A separate 28′ x 36′ heated garage provides generous space for vehicles, hobbies, or a workshop, plus a 960-square-foot, 1-bedroom apartment above with its own septic system. Live in one residence and rent the other, accommodate guests, or explore potential Airbnb use, subject to local requirements. Enjoy country living within approximately 3 hours of NYC and just 20 minutes from skiing at Jiminy Peak. Explore nearby Chatham and the Berkshires, with the Catskills offering additional options for day trips and outdoor adventures. Whether you're seeking a full-time home or a weekend escape, this property offers space, privacy, and the flexibility to live in one residence while renting the other.

3 Beds ⋅ 2 Baths ⋅ 202620622 MLS

Explore the possibilities with this 22 acre property featuring a 2,000-square-foot Cape with 3 bedrooms, 2 full baths, hardwood floors, and an attached 2-car garage. A separate 28′ x 36′ heated garage provides generous space for vehicles, hobbies, or a workshop, plus a 960-square-foot, 1-bedroom apartment above with its own septic system. Live in one residence and rent the other, accommodate guests, or explore potential Airbnb use, subject to local requirements. Enjoy country living within approximately 3 hours of NYC and just 20 minutes from skiing at Jiminy Peak. Explore nearby Chatham and the Berkshires, with the Catskills offering additional options for day trips and outdoor adventures. Whether you're seeking a full-time home or a weekend escape, this property offers space, privacy, and the flexibility to live in one residence while renting the other.

2439 County Route 5, New Lebanon

$645,000

Explore the possibilities with this 22 acre property featuring a 2,000-square-foot Cape with 3 bedrooms, 2 full baths, hardwood floors, 4 Season Room, and an attached 2-car garage. A separate 28′ x 36′ heated garage provides generous space for vehicles, hobbies, or a workshop, plus a 960-square-foot, 1-bedroom apartment above with its own septic system. Live in one residence and rent the other, accommodate guests, or explore potential Airbnb use, subject to local requirements. Enjoy country living within approximately 3 hours of NYC and just 20 minutes from skiing at Jiminy Peak. Explore nearby Chatham and the Berkshires, with the Catskills offering additional options for day trips and outdoor adventures. Whether you're seeking a full-time home or a weekend escape, this property offers space, privacy, and the flexibility to live in one residence while renting the other.

4 Beds ⋅ 3 Baths ⋅ 202620368 MLS

Explore the possibilities with this 22 acre property featuring a 2,000-square-foot Cape with 3 bedrooms, 2 full baths, hardwood floors, 4 Season Room, and an attached 2-car garage. A separate 28′ x 36′ heated garage provides generous space for vehicles, hobbies, or a workshop, plus a 960-square-foot, 1-bedroom apartment above with its own septic system. Live in one residence and rent the other, accommodate guests, or explore potential Airbnb use, subject to local requirements. Enjoy country living within approximately 3 hours of NYC and just 20 minutes from skiing at Jiminy Peak. Explore nearby Chatham and the Berkshires, with the Catskills offering additional options for day trips and outdoor adventures. Whether you're seeking a full-time home or a weekend escape, this property offers space, privacy, and the flexibility to live in one residence while renting the other.

2439 County Route 5, New Lebanon

$269,900

Imagine a crisp autumn morning, dew still resting on the ground. You step onto your front porch with a warm beverage in hand and take in the peaceful beauty of the surrounding countryside. For a few quiet moments, it's simply you and nature. As the cool air settles in and your drink begins to lose its warmth, you head back inside, where the woodstove keeps the living room cozy and inviting. Wander into the kitchen, finish making breakfast, and settle in to enjoy your morning in the comfort of home. Situated on approximately one acre, this three-bedroom, one-bath home offers the country setting you've been looking for while keeping you within reach of everyday destinations. East Chatham provides convenient access toward the Massachusetts border and the Berkshires, including the Pittsfield and Stockbridge areas, while Albany, Troy, and East Greenbush are also within driving distance. After a long day, pull into the attached basement garage and leave the outside world behind. As you walk up the stairs from the garage into the kitchen, the inviting aroma of the meal you left simmering in the crockpot all day welcomes you home. Relax to the sounds of nature, enjoy a refreshing shower in the updated bath, and settle in for a comfortable evening at home. Whether you're enjoying the brilliant colors of autumn, the warmth of the woodstove on a chilly day, or the peaceful surroundings of your own acre, 43 Frisbee Street offers a place to slow down, settle in, and feel at home. Welcome to 43 Frisbee Street--cozy, comfortable, and close.

3 Beds ⋅ 1 Baths ⋅ 202620053 MLS

Imagine a crisp autumn morning, dew still resting on the ground. You step onto your front porch with a warm beverage in hand and take in the peaceful beauty of the surrounding countryside. For a few quiet moments, it's simply you and nature. As the cool air settles in and your drink begins to lose its warmth, you head back inside, where the woodstove keeps the living room cozy and inviting. Wander into the kitchen, finish making breakfast, and settle in to enjoy your morning in the comfort of home. Situated on approximately one acre, this three-bedroom, one-bath home offers the country setting you've been looking for while keeping you within reach of everyday destinations. East Chatham provides convenient access toward the Massachusetts border and the Berkshires, including the Pittsfield and Stockbridge areas, while Albany, Troy, and East Greenbush are also within driving distance. After a long day, pull into the attached basement garage and leave the outside world behind. As you walk up the stairs from the garage into the kitchen, the inviting aroma of the meal you left simmering in the crockpot all day welcomes you home. Relax to the sounds of nature, enjoy a refreshing shower in the updated bath, and settle in for a comfortable evening at home. Whether you're enjoying the brilliant colors of autumn, the warmth of the woodstove on a chilly day, or the peaceful surroundings of your own acre, 43 Frisbee Street offers a place to slow down, settle in, and feel at home. Welcome to 43 Frisbee Street--cozy, comfortable, and close.

43 Frisbee Street, Chatham

$475,000

Welcome to your private retreat at 28 Covenant Circle in East Nassau. Nestled on 5 peaceful acres, this beautifully updated 4-bedroom, 2.5-bath home offers the perfect blend of modern comfort and country tranquility. The inside features many updates including: the entire home has been freshly painted, the gorgeous farmhouse wood floors have just been redone, the bathrooms have modern vanities and fixtures, and at the center of it all is the showstopping gourmet kitchen. Designed for both everyday living and entertaining, the expansive wraparound porch offers the perfect space to host gatherings, enjoy your morning coffee, or simply relax while taking in the privacy and natural surroundings. During the warmer months, the above-ground pool is the ideal place to cool off and enjoy the outdoors. The spacious basement offers abundant storage and the opportunity to create additional finished living space, whether you envision a recreation room, home gym, office, or guest suite. If you're looking for modern updates, generous space, and a quiet, private setting just a short drive from everyday conveniences, this exceptional property is one you won't want to miss. This home is USDA Loan Eligible, and the sellers are offering negotiable closing costs.

4 Beds ⋅ 3 Baths ⋅ 202620014 MLS

Welcome to your private retreat at 28 Covenant Circle in East Nassau. Nestled on 5 peaceful acres, this beautifully updated 4-bedroom, 2.5-bath home offers the perfect blend of modern comfort and country tranquility. The inside features many updates including: the entire home has been freshly painted, the gorgeous farmhouse wood floors have just been redone, the bathrooms have modern vanities and fixtures, and at the center of it all is the showstopping gourmet kitchen. Designed for both everyday living and entertaining, the expansive wraparound porch offers the perfect space to host gatherings, enjoy your morning coffee, or simply relax while taking in the privacy and natural surroundings. During the warmer months, the above-ground pool is the ideal place to cool off and enjoy the outdoors. The spacious basement offers abundant storage and the opportunity to create additional finished living space, whether you envision a recreation room, home gym, office, or guest suite. If you're looking for modern updates, generous space, and a quiet, private setting just a short drive from everyday conveniences, this exceptional property is one you won't want to miss. This home is USDA Loan Eligible, and the sellers are offering negotiable closing costs.

28 Covenant Circle, New Lebanon

$469,000

Surrounded by nature with 21 acres of private trails to roam. This architecturally striking 3BR/2BA home features a soaring cathedral-ceiling great room opening to a wrap deck, plus a lower-level hangout space perfect after a day outdoors. Central air, efficient propane systems, and an oversized 2-car garage make it easy to enjoy in every season. Minutes to Queechy Lake, Chatham, Hudson, the Berkshires, and skiing just 15 miles away. A private retreat with huge redecorating potential -- ideal for year-round adventure or a high-demand AirBnB escape. Short notice showings possible. Fiber optic high speed internet. 35-year architectural shingle guarantee (6-10yrs left). Decks 4-5yrs old. Mailbox end of driveway.

3 Beds ⋅ 2 Baths ⋅ 202619674 MLS

Surrounded by nature with 21 acres of private trails to roam. This architecturally striking 3BR/2BA home features a soaring cathedral-ceiling great room opening to a wrap deck, plus a lower-level hangout space perfect after a day outdoors. Central air, efficient propane systems, and an oversized 2-car garage make it easy to enjoy in every season. Minutes to Queechy Lake, Chatham, Hudson, the Berkshires, and skiing just 15 miles away. A private retreat with huge redecorating potential -- ideal for year-round adventure or a high-demand AirBnB escape. Short notice showings possible. Fiber optic high speed internet. 35-year architectural shingle guarantee (6-10yrs left). Decks 4-5yrs old. Mailbox end of driveway.

3620 County Route 9, New Lebanon

$430,000

New price reduction! This charming Hudson Home featuring 3 bedrooms and 1 bath is full of timeless character and thoughtful updates. Its original craftsmanship, abundant natural light and ideal location, being just minutes from vibrant Warren Street with all that Hudson has to offer, is just waiting for you to move right in. Inside, you'll find beautiful original woodwork, hardwood floors, and classic windows that preserve the home's historic charm. Sunlight fills the living spaces throughout the day, creating a warm and inviting atmosphere. The living and dining rooms have been recently painted, and the exterior of the home has also been freshly painted for excellent curb appeal. Recent updates include new furnace and hot water heater, new front and back storm doors and finished basement space. Outdoor features include a welcoming covered front porch and a partially fenced backyard perfect for relaxing, gardening, or entertaining. Conveniently located just a 5-minute drive to the Hudson Amtrak Station, making travel to New York City and beyond easy and accessible. A wonderful opportunity to own a character-filled home in one of the Hudson Valley's most desirable communities. Call today for your private showing.

3 Beds ⋅ 1 Baths ⋅ 202617293 MLS

New price reduction! This charming Hudson Home featuring 3 bedrooms and 1 bath is full of timeless character and thoughtful updates. Its original craftsmanship, abundant natural light and ideal location, being just minutes from vibrant Warren Street with all that Hudson has to offer, is just waiting for you to move right in. Inside, you'll find beautiful original woodwork, hardwood floors, and classic windows that preserve the home's historic charm. Sunlight fills the living spaces throughout the day, creating a warm and inviting atmosphere. The living and dining rooms have been recently painted, and the exterior of the home has also been freshly painted for excellent curb appeal. Recent updates include new furnace and hot water heater, new front and back storm doors and finished basement space. Outdoor features include a welcoming covered front porch and a partially fenced backyard perfect for relaxing, gardening, or entertaining. Conveniently located just a 5-minute drive to the Hudson Amtrak Station, making travel to New York City and beyond easy and accessible. A wonderful opportunity to own a character-filled home in one of the Hudson Valley's most desirable communities. Call today for your private showing.

957 Columbia Street, Hudson

$325,000

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, Philmont

$495,000

Discover the Charm of Country Living Escape to this authentic 3-bedroom, 2-bath log home tucked away on a peaceful private road in Ancram. Set on 5 acres, the property also includes a separate 3-acre buildable lot across the lane-perfect for maintaining privacy, creating a guest house or studio, or simply preserving your view and open space. Start your day with coffee on the front porch, or soak up the sunshine from the back deck. After a crisp autumn afternoon, unwind with a hot drink by the fire. With high-speed, fiber optic internet, you can stream your favorite shows or work remotely while surrounded by nature. Whether your passions lean toward the outdoors, local arts, farm-to-table dining, or simply quiet moments in the beauty of the Taconic Valley, this home offers the best of upstate living-serenity, character, and endless possibilities.

3 Beds ⋅ 2 Baths ⋅ 202616272 MLS

Discover the Charm of Country Living Escape to this authentic 3-bedroom, 2-bath log home tucked away on a peaceful private road in Ancram. Set on 5 acres, the property also includes a separate 3-acre buildable lot across the lane-perfect for maintaining privacy, creating a guest house or studio, or simply preserving your view and open space. Start your day with coffee on the front porch, or soak up the sunshine from the back deck. After a crisp autumn afternoon, unwind with a hot drink by the fire. With high-speed, fiber optic internet, you can stream your favorite shows or work remotely while surrounded by nature. Whether your passions lean toward the outdoors, local arts, farm-to-table dining, or simply quiet moments in the beauty of the Taconic Valley, this home offers the best of upstate living-serenity, character, and endless possibilities.

284 Hall Hill STOP 18, Ancram

$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, Hudson

$259,000

Tenants require 48hour notice to show and only after 10a.m. No Sunday showings preferred. All photos pre-occupancy. Easy living in this low-maintenance, fully renovated income home. Two two-bedroom apartments, each with refrigerator, range/oven, washer/dryer. MUNICIPAL WATER/SEWER. Covered front porch with a second-floor veranda above. Bright, happy home. Cable/High-speed internet available. 3 miles to Chatham Village/schools, 9 to Hudson/Amtrak, and a stroll to town park w/tennis courts, Bartlett House cafe and Dairy Queen. A wonderful small-town feel while being minutes from shopping and popular attractions, including bustling Warren Street, Chatham's Main Street, Omi, Hawthorne Valley Farm Store/School, libraries, MacHaydn and Crandell Theaters. Shown by Appt Only. Tenants require a minimum of 48-72 hours' notice.

4 Beds ⋅ 2 Baths ⋅ 202615136 MLS

Tenants require 48hour notice to show and only after 10a.m. No Sunday showings preferred. All photos pre-occupancy. Easy living in this low-maintenance, fully renovated income home. Two two-bedroom apartments, each with refrigerator, range/oven, washer/dryer. MUNICIPAL WATER/SEWER. Covered front porch with a second-floor veranda above. Bright, happy home. Cable/High-speed internet available. 3 miles to Chatham Village/schools, 9 to Hudson/Amtrak, and a stroll to town park w/tennis courts, Bartlett House cafe and Dairy Queen. A wonderful small-town feel while being minutes from shopping and popular attractions, including bustling Warren Street, Chatham's Main Street, Omi, Hawthorne Valley Farm Store/School, libraries, MacHaydn and Crandell Theaters. Shown by Appt Only. Tenants require a minimum of 48-72 hours' notice.

2261 State Route 66, Ghent

$495,000

Prime development opportunity in the heart of Hudson, NY, just a block from Warren Street and neighboring the beautifully restored Cannonball Factory. Three interconnected structures offer 4,400 square feet of versatile space: a historic brick building and two warehouse bays with wood frame truss construction, soaring ceilings, and an open, adaptable layout suited for office, retail, mixed-use, and beyond. Since last coming to market, the property has been advanced with structural stabilization, a full asbestos survey with clean results, and a new 400-amp electrical service, giving the next owner a meaningful head start. Located in an Opportunity Zone with significant capital gains tax incentives, this is a shovel-ready investment with the bones, location, and groundwork already in place. *Some photos have been virtually staged.

202614562 MLS

Prime development opportunity in the heart of Hudson, NY, just a block from Warren Street and neighboring the beautifully restored Cannonball Factory. Three interconnected structures offer 4,400 square feet of versatile space: a historic brick building and two warehouse bays with wood frame truss construction, soaring ceilings, and an open, adaptable layout suited for office, retail, mixed-use, and beyond. Since last coming to market, the property has been advanced with structural stabilization, a full asbestos survey with clean results, and a new 400-amp electrical service, giving the next owner a meaningful head start. Located in an Opportunity Zone with significant capital gains tax incentives, this is a shovel-ready investment with the bones, location, and groundwork already in place. *Some photos have been virtually staged.

357 Columbia Street, Hudson

$475,000

Lucrative income property in the center of a New England hamlet's business district. Minutes to Taconic State Parkway/ I90/ Berkshire Spur, 15 minutes to Lenox/ Tanglewood, 30 minutes Albany/ Capital Region. 3 buildings fully occupied incl 2BR/1.5BATH center hall 1930's home w/LG foyer staircase flanked by LG common RMS incl LR w/wood fireplace opposite spacious DR. Wood flrs throughout and leased for 2,300 dollars/MTH til 8/31/26. 2nd bldg is East Chatham Wine & Spirits store w/half-bath currently 1541 dollars/MTH-to-mth. 3rd bldg currently a funeral parlor/office w/half-bath 850 dollars/MTH til 4/30/26 All photos pre-occupancy. All units occupied. No interior liquor store photos. Tenants must approve all showings and provide access. 48HR notice minimum.

3 Beds ⋅ 2 Baths ⋅ 202613968 MLS

Lucrative income property in the center of a New England hamlet's business district. Minutes to Taconic State Parkway/ I90/ Berkshire Spur, 15 minutes to Lenox/ Tanglewood, 30 minutes Albany/ Capital Region. 3 buildings fully occupied incl 2BR/1.5BATH center hall 1930's home w/LG foyer staircase flanked by LG common RMS incl LR w/wood fireplace opposite spacious DR. Wood flrs throughout and leased for 2,300 dollars/MTH til 8/31/26. 2nd bldg is East Chatham Wine & Spirits store w/half-bath currently 1541 dollars/MTH-to-mth. 3rd bldg currently a funeral parlor/office w/half-bath 850 dollars/MTH til 4/30/26 All photos pre-occupancy. All units occupied. No interior liquor store photos. Tenants must approve all showings and provide access. 48HR notice minimum.

1129 New York 295, Chatham

$599,000

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, Claverack

$289,000

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, Chatham

$550,000

A peaceful, private retreat bordering protected land with no homes in sight. Enjoy a sparkling swimming pool, a dramatic 20' cathedral-ceiling great room, and seamless access to a deck overlooking the grounds and pool. Total quiet, total privacy, and minutes to the Berkshires for culture, dining, and farm-to-table markets. Includes coveted Queechy Lake rights. Principal en-suite and 3 other generously sized bedrooms - 3 baths - 8 person SAUNA -- must see Owner-occupied. Please allow 24-48 hours' notice.

4 Beds ⋅ 3 Baths ⋅ 202613439 MLS

A peaceful, private retreat bordering protected land with no homes in sight. Enjoy a sparkling swimming pool, a dramatic 20' cathedral-ceiling great room, and seamless access to a deck overlooking the grounds and pool. Total quiet, total privacy, and minutes to the Berkshires for culture, dining, and farm-to-table markets. Includes coveted Queechy Lake rights. Principal en-suite and 3 other generously sized bedrooms - 3 baths - 8 person SAUNA -- must see Owner-occupied. Please allow 24-48 hours' notice.

614 Salls Road, New Lebanon

$440,000

142 Main Street, Philmont, NY 12565 Fully Rented 4-Unit Investment Opportunity Turn-key multi-family property in the heart of Philmont featuring four fully rented units with strong rental income and diverse layouts. Ideal for investors seeking immediate cash flow in a centrally located village setting. This building offers: Unit 1 (1st Floor): 2 Bedrooms, 1 Bath Approx. 800 sq ft. Unit 2 (2nd Floor): 2 Bedrooms, 1 Bath Approx. 800 sq ft. Unit 3 (Townhouse Style): Spanning first & second floors with private basement space and in-unit washer/dryer Approx. 900 sq ft. Unit 4 (2nd Floor Rear): 1 Bedroom, 1 Bath Approx. 500 sq ft. All units are currently leased, offering immediate income from day one. The mix of two-bedroom layouts and an efficient one-bedroom unit provides strong tenant appeal. Unit 3's multi-level design and private basement area add flexibility and value. Conveniently located near local shops, dining, and village amenities with easy access to major routes including the TSP. 15 minutes to Amtrak. A solid addition to any investment portfolio with established rental history and upside potential.

8 Beds ⋅ 4 Baths ⋅ 202612282 MLS

142 Main Street, Philmont, NY 12565 Fully Rented 4-Unit Investment Opportunity Turn-key multi-family property in the heart of Philmont featuring four fully rented units with strong rental income and diverse layouts. Ideal for investors seeking immediate cash flow in a centrally located village setting. This building offers: Unit 1 (1st Floor): 2 Bedrooms, 1 Bath Approx. 800 sq ft. Unit 2 (2nd Floor): 2 Bedrooms, 1 Bath Approx. 800 sq ft. Unit 3 (Townhouse Style): Spanning first & second floors with private basement space and in-unit washer/dryer Approx. 900 sq ft. Unit 4 (2nd Floor Rear): 1 Bedroom, 1 Bath Approx. 500 sq ft. All units are currently leased, offering immediate income from day one. The mix of two-bedroom layouts and an efficient one-bedroom unit provides strong tenant appeal. Unit 3's multi-level design and private basement area add flexibility and value. Conveniently located near local shops, dining, and village amenities with easy access to major routes including the TSP. 15 minutes to Amtrak. A solid addition to any investment portfolio with established rental history and upside potential.

142 Main Street, Philmont

$599,000

2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers - properties not sold separately. Assessment/tax figures herein reflect total due for both properties. Photos incl Ranch house and 2 apartments pre-occupancy. 48hour notice required to show. Buyer/Coop brokers must attend all appointments. Thank you for your interest. Tenants must approve and provide access.

9 Beds ⋅ 6 Baths ⋅ 202610680 MLS

2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers - properties not sold separately. Assessment/tax figures herein reflect total due for both properties. Photos incl Ranch house and 2 apartments pre-occupancy. 48hour notice required to show. Buyer/Coop brokers must attend all appointments. Thank you for your interest. Tenants must approve and provide access.

1121-1123 New York 295, Chatham

$495,000

PRICE CHANGE!!! Newly remodeled from top to bottom. Well known area top builder is the owner. Beautiful flat lot, protected on one side by a conservancy. Move in and live maintenance free for many years. 3 beds, 2 full baths. One bed and bath on the first floor. Light and bright in every room. Basement fully insulated, whole house is energy efficient. Semi private but close to everything. Skiing, Berkshires, TSP, I90.

3 Beds ⋅ 2 Baths ⋅ 202530207 MLS

PRICE CHANGE!!! Newly remodeled from top to bottom. Well known area top builder is the owner. Beautiful flat lot, protected on one side by a conservancy. Move in and live maintenance free for many years. 3 beds, 2 full baths. One bed and bath on the first floor. Light and bright in every room. Basement fully insulated, whole house is energy efficient. Semi private but close to everything. Skiing, Berkshires, TSP, I90.

263 Old Hudson Turnpike, Canaan

$290,000

Price has been dropped to a saleable price

3 Beds ⋅ 1 Baths ⋅ 202530043 MLS

Price has been dropped to a saleable price

4649 County Route 9, New Lebanon

$699,000

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, Ghent