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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
$225,000
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. Offered at $250,000, 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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