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152 Main Street, Philmont
$295,000
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

1135 NY-295, Chatham
$289,000
2 Baths ⋅ 202613557 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 NY-295, Chatham

1135 New York 295, Chatham
$289,000
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

1711 County Route 27, Taghkanic
$285,000
202626946 MLS
A truly unique Upstate NY opportunity! Offered together, 27.14 total acres combine a 1,040 sq ft cabin (26x40, seller-confirmed) on 1.74 acres with an additional 25.40-acre parcel (153.-1.46), conveyed as one incredible package -- Set up game cameras, hang your tree stands, and gather your buddies for group hunting outings on land built for whitetail, turkey, and true four-season recreation. Well laid-out, easy-to-follow trails wind through the property to clearings, creeks, and beyond, with ATV and snowmobile access right out your back door. The cozy cabin offers an open-concept kitchen and living room plus a private sleeping quarters, full electric, and comes fully furnished -- including AC units and wood stove -- so it's ready to enjoy from day one. Several outbuildings provide ample storage for ATVs, snowmobiles, and all your gear. A portable toilet on-site keeps things simple; no other infrastructure needed. Just a short drive from Albany, Connecticut and within easy reach of New York City and New Jersey, this is a true wilderness destination for anyone craving an escape from the city without the long haul. Prefer to build instead? This sprawling acreage is also a fantastic new construction opportunity -- bring your builder and create the Upstate NY retreat or homestead you've always dreamed of. Properties combining this much acreage, bordering state land, with an existing cabin and power already in place don't come around often!

1711 County Route 27, Taghkanic

1711 County Route 27, Taghkanic
$285,000
1 Beds ⋅ 202626069 MLS
A truly unique Upstate NY opportunity! Offered together, 27.14 total acres combine a 1,040 sq ft cabin (26x40, seller-confirmed) on 1.74 acres with an additional 25.40-acre parcel (153.-1.46), conveyed as one incredible package -- Set up game cameras, hang your tree stands, and gather your buddies for group hunting outings on land built for whitetail, turkey, and true four-season recreation. Well laid-out, easy-to-follow trails wind through the property to clearings, creeks, and beyond, with ATV and snowmobile access right out your back door. The cozy cabin offers an open-concept kitchen and living room plus a private sleeping quarters, full electric, and comes fully furnished -- including AC units and wood stove -- so it's ready to enjoy from day one. Several outbuildings provide ample storage for ATVs, snowmobiles, and all your gear. A portable toilet on-site keeps things simple; no other infrastructure needed. Just a short drive from Albany, Connecticut and within easy reach of New York City and New Jersey, this is a true wilderness destination for anyone craving an escape from the city without the long haul. Prefer to build instead? This sprawling acreage is also a fantastic new construction opportunity -- bring your builder and create the Upstate NY retreat or homestead you've always dreamed of. Properties combining this much acreage, bordering state land, with an existing cabin and power already in place don't come around often!

1711 County Route 27, Taghkanic

184 The Concourse, Kinderhook
$275,000
3 Beds ⋅ 1 Baths ⋅ 202628788 MLS
Welcome to 184 The Concourse in the Town of Kinderhook! Situated on a 0.29-acre lot within the Ichabod Crane Central School District, this 3-bedroom, 1-bath ranch offers approximately 1,818 sq. ft. of living space. Inside, you'll find spacious living areas, a generously sized kitchen with ample countertop space, two pellet stoves, and electric heat. Just off the kitchen, a spacious deck overlooks the fenced backyard, perfect for relaxing or entertaining. Additional highlights include cedar siding, a beautiful U-shaped driveway, a fiberglass shingle roof installed approximately five years ago with an estimated five years remaining on its 10-year transferable warranty, private well, and septic system. Don't miss the opportunity to explore all this property has to offer—schedule your showing today!

184 The Concourse, Kinderhook

43 Frisbee Street, Chatham
$264,900
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

2261 State Route 66, Ghent
$259,000
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

32 Lovers Lane, New Lebanon
$257,000
6 Beds ⋅ 2 Baths ⋅ 202628378 MLS
Don't miss this bright and versatile two-family home! Filled with natural light and full of character, this well-maintained property offers endless possibilities. Each apartment features three bedrooms, a full bath, kitchen, living room, and dining room, along with a charming three-season room highlighted by a wall of glass that welcomes abundant sunlight. Original woodwork throughout adds warmth and timeless appeal, while two electric meters and two boilers provide convenience and flexibility. Both units are move-in ready and awaiting your personal touches and updates. Whether you're looking for an owner-occupied investment, a multi-generational living arrangement, or the opportunity to convert the property into a spacious single-family home, this property delivers. Ideally situated on a quiet country road just minutes from town, you'll enjoy easy access to the Berkshires, Chatham, Hudson, the Taconic State Parkway, and I-87. Albany is less than 30 minutes away, making this an excellent location for both convenience and country living.

32 Lovers Lane, New Lebanon

1432 Rte 295, Canaan
$249,000
2 Beds ⋅ 1 Baths ⋅ 202628630 MLS
Welcome to this charming 1850 post-and-beam country retreat set on 5 peaceful acres in the heart of East Chatham. Rich with character and surrounded by nature, this inviting 2-bedroom home blends historic warmth with flexible modern living--perfect for full-time residents, weekenders, and anyone seeking a creative escape minutes from the Berkshires. Inside, exposed beams, wide plank floors, and sunlit rooms create an atmosphere that feels instantly grounding. The layout offers comfortable everyday living with opportunities to personalize through light cosmetic updates, allowing buyers to add their own style without taking on major renovation projects. A standout feature of this property is the detached, heated ''bungalow/flex space'', equipped with 50-amp service and electric baseboard heat. This versatile building is ideal for an art studio, private office, home gym, wellness space, or a remote-work retreat--a rare amenity that expands how you live, create, and work. Outside, the acreage offers privacy, wooded buffers, and room to explore, garden, or simply enjoy the quiet rhythm of country life. Located along scenic Route 295, you're minutes to Queechy Lake, the Taconic, I-90, and the cultural and outdoor experiences of the Berkshires. A character-rich home with land, lifestyle appeal, and a multi-purpose heated space--this is a special opportunity in one of Columbia County's most sought-after rural corridors.

1432 Rte 295, Canaan

10695 Route 22, Hillsdale
$248,000
202628023 MLS
Discover an extraordinary opportunity to create your dream home or private country retreat on this beautiful 15.8-acre parcel located within the Hudson Valley of Columbia County on the western edge of the Berkshire Mountains. Potential home site can put you well away from the road for exceptional privacy overlooking a picturesque, one+- acre spring-fed pond. Imagine waking each morning to tranquil water views, surrounded by the natural beauty of a mature woodland with the perfect blend of maple, oak, ash, beech, etc. Whether envisioned as a year-round primary residence or a peaceful weekend escape, this special setting offers an appealing blend of seclusion, scenery, and the best of nature. Enjoy the serenity of a private country setting while remaining conveniently located just 10 minutes from Great Barrington where you can enjoy a mix of outdoor adventures, cultural landmarks, local shopping, distinctive shops, farm-to-table dining and more. Only two hours south of New York City, this is a rare opportunity to create a personal sanctuary in one of the Northeast's most desirable destinations.

10695 Route 22, Hillsdale

L30.4 Old Gale Hill Road, New Lebanon
$245,000
202627750 MLS
Peace, privacy, and natural beauty come together on this expansive parcel of nearly 32 acres in New Lebanon. Set along quiet Old Gale Hill Road, the property offers a serene country setting surrounded by woods, with a substantial cleared area already completed and ready to be incorporated into your plans. A driveway has been started, adding to the property's accessibility and potential. The combination of open space and wooded acreage creates a versatile landscape with room to explore, enjoy the outdoors, or envision a private retreat surrounded by nature. The quiet setting is truly the standout feature here—peaceful, private, and removed from the everyday hustle. Just minutes from Hand Hollow Conservation Area and within easy reach of the Berkshires, the property offers convenient access to outdoor recreation, dining, arts, culture, and year-round attractions while maintaining the tranquility of a rural Columbia County setting. A rare opportunity to secure substantial acreage in a beautiful and peaceful corner of Columbia County, with the space and flexibility to make it your own.

L30.4 Old Gale Hill Road, New Lebanon

396 U.S. 20, New Lebanon
$210,000
202622183 MLS
Position your business for success in this versatile 3,170 sq. ft. commercial building in the heart of New Lebanon, just minutes from the Massachusetts border. Situated on a highly traveled roadway, this outstanding location offers exceptional visibility and easy access for customers and clients alike. The sale includes the building and 1.99-acre parcel only; the existing auto repair business is not included. The flexible layout features four oversized garage bays, making it ideal for a wide range of commercial uses including retail, professional offices, contractor headquarters, light manufacturing, warehouse space, artist studios, sculpture workshops, maker space, or a creative mixed-use environment. The expansive interior provides endless possibilities to customize the space to fit your vision. The nearly 2-acre lot offers ample parking, room for expansion, and a peaceful creek running through the property, creating a unique natural backdrop rarely found with commercial real estate. Whether you're launching a new venture, relocating an established business, or investing in a property with incredible potential, this high-visibility location is ready for its next chapter.

396 U.S. 20, New Lebanon

L9.111 US Route 20, New Lebanon
$160,000
202623883 MLS
Seller financing is available! This picturesque property offers a beautiful creek, mature timber, abundant wildlife, and exceptional privacy, making it an ideal investment or private retreat. With versatile mixed-use zoning, the possibilities are wide open; build a cabin or future homesite, create your own hunting or recreational getaway, hold the property as a long-term land and timber investment, or bring a business, farm, or other creative vision to life. An up-to-date survey is available from the seller and will be provided to the buyer, offering valuable information for planning and evaluating the property. The property features a flowing creek highlighted in the newly updated photos, rolling natural terrain, plenty of room to explore or build, and rare development flexibility for a parcel of this size in New Lebanon. With attractive pricing and seller financing available, this is a great opportunity to secure your own Upstate getaway while investing in land with long-term potential. Schedule a private showing and come walk the creek before this opportunity is gone!

L9.111 US Route 20, New Lebanon

1780 County Route 22, Valatie
$140,000
202620328 MLS
Opportunity awaits on this beautiful 5.8-acre parcel loaded with potential! Already cleared and featuring a roughed-in driveway, existing slab, dug well, and two septic systems, much of the groundwork has been started for you. Whether you're dreaming of building a private country estate, creating a multi-generational family compound, or exploring other possibilities, this property offers the space and flexibility to make it happen. With plenty of room to spread out and a variety of potential future uses, this is a rare chance to own acreage that's ready for your vision. Bring your ideas and imagine the possibilities! Situated in a prime location just 10 minutes from Chatham, Kinderhook or Valatie! Located in the Chatham CSD.

1780 County Route 22, Valatie

67 River Street, Chatham
$125,000
202625080 MLS
Beautiful 8.5-acre piece of land composed of 2 parcels with an exceptional location near the Village of Chatham. The property includes approximately 1.8 acres within the Village, with municipal water and sewer located just up the road, offering convenient access to utilities. The land features plenty of cleared, usable acreage with room to build your dream home, create a small farm, or enjoy your own private country setting--subject to town approvals. A perc test has already been completed, adding valuable peace of mind for future planning. Enjoy the best of both worlds: peaceful open space with the Village of Chatham close by, providing convenient access to local shops, restaurants, services, and community amenities. A wonderful opportunity to create your ideal home or homestead in a beautiful, convenient Chatham location. Listing contains 2 parcels: 56.-1-39 and 56.18-1-4.

67 River Street, Chatham

189 Covenant Circle, New Lebanon
$85,000
202621732 MLS
If you're seeking privacy in the woods with stunning seasonal views, this property offers incredible potential. The proposed building site, sits halfway up the land and has already begun to be cleared, giving you a head start on creating your dream retreat. The beginnings of a roadway are in place, though a full driveway will need to be completed to access the site. With additional clearing, you can unlock breathtaking west-facing views--perfect for sunsets and long-range scenery. From this elevated vantage point, you'll enjoy complete seclusion, with no visible neighboring homes for miles. Ideally located just a short drive from the Berkshires, Albany, Chatham, and Hudson, this property combines peaceful rural living with convenient access to culture, dining, and outdoor recreation. An annual HOA fee of 850 covers road maintenance, snow plowing, and general upkeep. Bring your vision and transform this private woodland setting into something truly special.

189 Covenant Circle, New Lebanon

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