Columbia County NY Homes under $400,000

• 

  

  

  /18

  $395,000

  • 6 Beds
  • 2.5 Baths
  • 4,000 Sq Ft

  3630 Mechanic St, Valatie, NY 12184

  Large farmhouse on one of Valatie's largest village lots of 1.11 A. 4000+ sq ft country home with 6 bedrooms and 2.5 baths. Large meandering rooms suitable for a large extended family or make apartments. There are two large enclosed porches (one with a woodstove) plus a covered outdoor summer patio. Also on the property is a 1000 square foot outbuilding suitable for a studio or workshop. Many

  

  William Laraway

  Val Kin Properties, LLC

  (518) 873-4404

  3630 Mechanic St, Valatie, NY 12184
• 

  

  

  /20

  $320,000

  • Land
  • 9 Acres
  • $36,364 per Acre

  0 County Route 27, Copake, NY 12516

  Wooded 8+ acre building lot in Copake NY. Build your dream home on this spacious, wooded, 8+ acre lot in scenic Copake. Conveniently located just minutes from Copake Lake, Ancram, the Taconic Parkway, and a variety of outdoor and recreational activities. Enjoy peaceful country living with easy access to shopping, dining, and local attractions. A perfect blend of seclusion and convenience. Land is

  Allen Olmsted

  0 County Route 27, Copake, NY 12516
• 

  

  

  /8

  $399,000

  • 1 Bed
  • 1 Bath
  • 690 Sq Ft

  251 Overlook Dr, Hillsdale, NY 12529

  Location location. Picturesque Overlook Dr in Hillsdale. Surrounded by large estates. The perfect early 1900s cottage on a gorgeous parcel. Lightly wooded with the potential for bigger views. Seasonal Berkshire views and stream that runs year round. Massive stone fireplace newly lined perfect for fall and winter nights. New enameled wood stove perfect for apres ski enjoyment. Close to Catamount

  Tracy Tassinari Gabel Real Estate

  251 Overlook Dr, Hillsdale, NY 12529
• 

  

  

  /48

  $390,000

  • 4 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  33 Mountain View Dr, Valatie, NY 12184

  Meticulously well-maintained split-level ranch home is move in ready! Upon entering this home you'll be greeted with hardwood floors throughout, 3 nicely sized bedrooms upstairs with the primary boasting a full bath. Updated windows, new septic in 1990, 6 panel doors, an open kitchen, dining, living area with working. Downstairs boasts an additional bedroom, and family area w/ wood fireplace a

  Christie Cimmino Gabler Realty, LLC

  33 Mountain View Dr, Valatie, NY 12184
• 

  

  

  /12

  $399,999 Open Sat 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  7 James St, Hudson, NY 12534

  An absolute perfect starter , retirement or family home convenient to all amenities . One of the best features is a double lot completely fenced in for the safety of children or pets. This home was built to last with loving care. Another great feature is the large, enclosed back porch with all new windows and a view of the lovely back yard. The inside is extremely well cared for with custom

  Nancy Randall Val Kin Properties, LLC

  7 James St, Hudson, NY 12534
• 

  

  /21

  $399,000

  • 1 Bed
  • 1.5 Baths
  • 1,872 Sq Ft

  33 Fischer Rd, Kinderhook, NY 12106

  Welcome to this private, peaceful, 1800 square ft Home bi-level ranch 900 square ft Upstairs with 1 bedroom and Full bathroom, kitchen, dining area and living room with a working fireplace, Downstairs also 900 square ft easy second bedroom or entertaining room with 1/2 bath and laundry Plus another working fireplace. Located on a quiet dead-end road with its own private driveway. Enjoy a seamless

  George Opshanski George Opshanski Real Estate

  33 Fischer Rd, Kinderhook, NY 12106
• 

  

  /96

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft

  4520 New York 66, Malden Bridge, NY 12115

  A Lovely 3 to 4 Bedroom, 2 Bath Home with a 2 Car Garage on 8.8 Acres! The 1st floor features 3 bedrooms, 1 bath, a kitchen, a dining area, a living room with a fireplace, and a sunroom. The living room has a beautiful stone fireplace with a Jotul Wood Stove insert. The kitchen has a breakfast bar. The dining area walks out to a charming sunroom. The basement features partially finished living

  Ted Banta RVW Select Properties

  4520 New York 66, Malden Bridge, NY 12115
• 

  

  /18

  $375,000

  • 4 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  16 Oakwood Blvd, Hudson, NY 12534

  Classic Hudson Home with Big Potential!!Priced below appraisal, this 4BR, 1.5BA 1925 home sits on a 0.33-acre lot in a quiet neighborhood. Features include a large eat-in kitchen, original wood floors (under carpet), vintage details, and a layout ready for your updates. Spacious yard, detached garage, and room to garden or expand. Walk to downtown shops, restaurants, and galleries.

  Elizabeth Hendler Berkshire Hathaway HomeServices Blake, REALTORS

  16 Oakwood Blvd, Hudson, NY 12534
• 

  

  /30

  $374,900

  • 5 Beds
  • 2 Baths
  • 1,876 Sq Ft

  4283 County Route 9, East Chatham, NY 12060

  PRICED TO SELL!! Attention race fans. One floor living at it's best. This sprawling ranch has 5 Bedrooms, including a main bedroom ensuite, 2 full baths, oversized kitchen and living room, and a 3 Season room. All set on 8 flat acres. Off of route 20 but close access to the TSP, and I90. If you like the racing scene, Lebanon Valley Speedway is right down the road. Close to skiing and all

  Leonard Brown Berkshire Hathaway HomeService

  4283 County Route 9, East Chatham, NY 12060
• 

  

  /31

  $335,000

  • 4 Beds
  • 1.5 Baths
  • 1,951 Sq Ft

  40 Broad St, Kinderhook, NY 12106

  Experience life in Kinderhook Village in this 19th century four bedroom house. Updated in the 1920's and now is ready for improvements and renovation. Beautiful wood floors are throughout the house along with original 19th century window moldings in the living room, an elegant staircase with the original banister and lovely details throughout the house. The classic center hall design has a

  Sarah Lipsky William Pitt Sothebys Intn'l

  40 Broad St, Kinderhook, NY 12106
• 

  

  /33

  $345,000

  • 4 Beds
  • 2 Baths
  • 2,612 Sq Ft

  45 Chatham St, Kinderhook, NY 12106

  Step into the charm of early American history with this 1830-built home, just a quarter-mile from the heart of the vibrant Village of Kinderhook. Set on a spacious 0.88-acre lot, this 5-bedroom, 2-bath residence showcases original wide plank floors, exposed beams, wood paneling, and remnants of historic brick ovens—ready to inspire your vision.Recent updates include newly redone walls,

  Janet Glaude Howard Hanna Capital Inc

  45 Chatham St, Kinderhook, NY 12106
• 

  

  /5

  $310,000

  • 5 Beds
  • 2 Baths
  • 2,350 Sq Ft

  225 1/2 Columbia St, Hudson, NY 12534

  Fantastic investment or starter opportunity in the heart of Hudson! This two-family home sits on a double lot offering endless possibilities. Each spacious apartment is approximately 1,200 sq ft, perfect for owner-occupants to live in one unit and have rental income to cover expenses. There is an additional structure next to the 2 family. This was a former neighborhood store. Both buildings need

  Elizabeth Hendler Berkshire Hathaway HomeService

  225 1/2 Columbia St, Hudson, NY 12534
• 

  

  /5

  $325,000

  • Land
  • 24 Acres
  • $13,363 per Acre

  0 W Hill Rd Unit 20253831, Austerlitz, NY 12017

  Wonderful private parcel of land with wooded glens, open fields and Green River frontage. Views of Harvey Mountain. Usable land, close to the Berkshires. Frontage on two roads. Subdividable. Level land with mature trees. Great location close to the Berkshires, Hawthorne Valley School, Hudson and Chatham.

  Tracy Tassinari Gabel Real Estate

  0 W Hill Rd Unit 20253831, Austerlitz, NY 12017
• 

  

  /14

  $310,000

  • 3 Beds
  • 1 Bath
  • 1,504 Sq Ft

  176 Main St, Philmont, NY 12565

  Charming three bedroom, one bath farm house featuring wood flooring and timeless character. The rooms on the main floor are spacious and bright, always warm and welcoming. There is a home office for those working from home or use for a small library. Private quarters are upstairs featuring three bedrooms with wood floors and a room at the end of the hall for a second bath or closet. Outside, a

  Karen Davala DAVALA REAL ESTATE LLC

  176 Main St, Philmont, NY 12565
• 

  

  /20

  $310,000

  • 2 Beds
  • 2 Baths
  • 1,318 Sq Ft

  10 County Route 9, Hudson, NY 12534

  This charming Greek Revival offers the perfect blend of historic character and modern comfort. Set beside a tranquil creek, the home is filled with natural light and features a spacious living room that opens to a beautiful three-season screened porch with serene views of the water and lush green trees.Inside, you'll find two bedrooms, two full baths, and original wide-plank floors dating

  Dana Matthews Rouse + Co Real Estate, LLC

  10 County Route 9, Hudson, NY 12534
• 

  

  /14

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  229 Cold Spring Rd, Hudson, NY 12534

  Tucked away on a peaceful country road just outside Hudson is this 3-bedroom, 2 bathroom home. This residence offers a solid foundation with endless renovation possibilities perfect for buyers looking to tailor their own style. Step outside to discover a generous yard offering room for gardening, outdoor dining or play. A partially finished basement perfect for home gym, home office or additional

  Joyce Vale Coldwell Banker Advisor Realty

  229 Cold Spring Rd, Hudson, NY 12534
• 

  

  /14

  $375,000

  • 4 Beds
  • 4 Baths
  • 1,976 Sq Ft

  36 Spring St, Chatham, NY 12037

  This well-maintained multi-unit building offers a strong investment opportunity, with numerous updates, upgrades, and consistent maintenance over the years. The perfect opportunity to live and invest simultaneously, with three units that cater to both owner-occupants and investors.As of July 1st, 2025, Apt #3 with 2 Bedrooms will be available, making it perfect for those looking to owner

  Melinda Barbanti Davala Real Estate, LLC

  36 Spring St, Chatham, NY 12037
• 

  

  /21

  $398,000

  • 3 Beds
  • 2 Baths
  • 1,509 Sq Ft

  19 Fabiano Blvd, Hudson, NY 12534

  Welcome to a charming 3 bedroom, 2 bathroom home nestled in the heart of Greenport. Whether you are dreaming of a modern update or prefer the character of its current style, there's plenty of renovation potential to explore. Inside you will find well proportioned layouts just waiting for your personal touch. Just a short trip away to shopping. Nearby Empire State Trail. Come see what's possible,

  Joyce Vale Coldwell Banker Advisor Realty

  19 Fabiano Blvd, Hudson, NY 12534
• 

  

  /19

  $334,000

  • 3 Beds
  • 1.5 Baths
  • 1,136 Sq Ft

  623 Empire Rd, Copake, NY 12516

  Completely renovated and update 3BR1.5BA Ranch Home in mint condition with room in basement. New furnace, water conditioner, well pump, washer, dryer. Great yard with fire pit and backyard plantings adjoining deck. Also has front porch. This is in move in condition with easy walking to Copake Village, including diner, gas station, grocery stores, bank. Short walk to emergency care.

  David Birch Barns & Farms Realty, LLC

  623 Empire Rd, Copake, NY 12516
• 

  

  /18

  $335,000

  • Land
  • 7 Acres
  • $47,383 per Acre

  13191 Route 22 Stop #20, Canaan, NY 12029

  7 Acres of Prime Farmland with Barns in Canaan, NYLooking to start or grow your farm? This 7-acre parcel right on State Route 22 in Canaan has everything you need to hit the ground running. The fields have a high pH level--great for growing crops--and there's a reliable well on site producing 8 gallons per minute.You'll also find two solid barns with newer roofs (just 5 years old), perfect for

  Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  13191 Route 22 Stop #20, Canaan, NY 12029
• 

  

  /19

  $355,000

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  438 Route 217, Hudson, NY 12534

  Originally built circa 1960, the updated and expanded four-bedroom rambling farmhouse, provides a blend of charm and modern convenience with a top-tier Mitsubishi Mini-Split system for AC, heat, and dehumidification backed by state-of-the-art Buderus hot water baseboard heating system. The ground floor includes the kitchen and breakfast area, open living/dining area, den (with glass sliding doors

  Peggy Lampman Peggy Lampman

  438 Route 217, Hudson, NY 12534
• 

  

  /28

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  41 Cheviot Rd, Germantown, NY 12526

  Well-maintained and cared for home just a short stroll from the banks of the Hudson River located in the picturesque Hamlet of Cheviot in the town of Germantown. Enjoy year-round views of the Catskill Mountains blue silhouette from the rear deck and partial-year views of the majestic Hudson River. Move-in ready but with options for updates to make the space your own. Only minutes from the

  Marco Carvajal Coldwell Banker Prime

  41 Cheviot Rd, Germantown, NY 12526
• 

  

  /18

  $345,000

  • 6 Beds
  • 4 Baths
  • 6,046 Sq Ft

  170 County Route 7a Unit 1, Copake, NY 12516

  BRING ALL OFFERS! Put A Fork in Us, We're Done!! It's time for the next chapter of the Copake Inn. With a long-standing history in the center of Copake -- ahh, if only the walls could talk, the stories that could be told.The Horse Shoe bar remains, along with room for dining tables, dancing and a pool table on the main floor. Living space on the upper level includes single rooms with a hallway

  Lindsay Lebrecht Copake Lake Realty Corp.

  170 County Route 7a Unit 1, Copake, NY 12516
• 

  

  /27

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  623 New York 9j, Stuyvesant, NY 12173

  Tucked away along the serene banks of the Hudson River, this beautifully maintained three-bedroom home offers a rare blend of rustic charm and tranquil living. Centered around a stunning, oversized stone fireplace, the heart of the home radiates warmth and comfort, perfectly complemented by rich wood tones and exposed timber beams. Outdoors, the property feels like your own private nature

  Ryan Lane Gilcrest Properties

  623 New York 9j, Stuyvesant, NY 12173
• 

  

  /14

  $340,000

  • 3 Beds
  • 2 Baths
  • 1,308 Sq Ft

  148 Lake Shore Dr, Copake, NY 12516

  Mid-Summer Price Improvement. The owners offer this beautifully renovated 3-bedroom 2 full bath home on Robinson Pond in picturesque Columbia County! Featuring 3 bedrooms (1 ensuite primary and 2 guest rooms), the home has been freshly painted and updated including brand new stainless steel appliances. The bathroom vanities and tiled showers with large glass doors are right out of the best HGTV

  Mark Saxby Berkshire Hathaway HomeService

  148 Lake Shore Dr, Copake, NY 12516
• 

  

  /18

  $399,900

  • 5 Beds
  • 3 Baths
  • 3,504 Sq Ft

  75-77 S 3rd St, Hudson, NY 12534

  Prime investment opportunity in the heart of Hudson NY! Just a short distance to Warren Street, the antique warehouse and the Amtrak station, this 3-unit property offers incredible potential! It includes two 2-BD, 1-BA units with an extra room that could be a 3rd bedroom with proper zoning. The first-floor unit is framed as a 1-BD, 1-BA and ready to be finished. A detached carriage house adds

  Emma Schaeffer Empire Real Estate Firm LLC

  75-77 S 3rd St, Hudson, NY 12534
• 

  

  /12

  $390,000

  • Land
  • 10 Acres
  • $40,710 per Acre

  2094 County Route 8, Taghkanic, NY 12523

  Elizaville area 9.58 acre parcel of land with electric, well, 300 sq ft outbuilding/studio and Doove Kill Stream frontage. Cleared building site, privately located back from the road. Board of Health approved for a four bedroom house with an inground septic system. Easy to reach from the Taconic Parkway and 15 minutes from Hudson and the Amtrack Station.

  PATRICIA HINKEIN Patricia A. Hinkein Realty

  2094 County Route 8, Taghkanic, NY 12523
• 

  

  /10

  $399,000

  • Land
  • 10 Acres
  • $39,272 per Acre

  0 Pleasantvale Rd, Tivoli, NY 12583

  Your Hudson Valley dream enclave awaits. Set at the end of a quiet road lined with hard woods framing your drive to paradise, this 10-acre parcel is something out of a story book. Bucolic and majestic views unroll on every acre of this parcel. The perfect home site has already been chosen, with dreamy views of rolling greens and the tops of the Catskill mountains perched behind it. This prime

  Chelsea Pollard-Seiler Mondello Upstate Properties

  0 Pleasantvale Rd, Tivoli, NY 12583
• 

  

  /19

  $347,000

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft

  81 SW Sw Colony Rd, Hillsdale, NY 12529

  Welcome to Copake Lake!! Sweet two-bedroom, one bath cottage, eat in kitchen, views of the lake from living room and one of the two bedrooms, nice big yard to enjoy outdoor fun. All appliances included. PLUS (As per Seller) water rights along that 20-foot stretch, a buyer may be able to agree with others in the area to extend the existing dock, which could be up to 60 feet into the lake!

  Margaret Bower Avenia Columbia County RE Specialist

  81 SW Sw Colony Rd, Hillsdale, NY 12529
• 

  

  /11

  $390,000

  • Land
  • 45 Acres
  • $8,667 per Acre

  0 County Route 28-A Unit 20251992, Chatham Center, NY 12184

  Commanding panoramic views in the heart of Chatham Center span the Helderbergs, Jiminy Peak and the Berkshires, and into Village of Chatham — all visible from the top of this dramatic hilltop parcel. With 5-acre zoning, the property has potential for subdivision, or the perfect opportunity to build a striking home on the hill, surrounded by sweeping, bucolic landscapes. A rare and spectacular

  Scott Paladino Chatham Properties

  0 County Route 28-A Unit 20251992, Chatham Center, NY 12184
• 

  

  /22

  $395,000

  • 3 Beds
  • 1 Bath
  • 1,240 Sq Ft

  85 Summit St, Philmont, NY 12565

  Hilltop living in Philmont! Welcome to 85 Summit Street, a three bedroom ranch located off of a private driveway just outside the village of Philmont. The property is 12 minutes to Hudson. You're greeted by a stone facade as you arrive by the well-landscaped driveway. Park in back and enter the house through a skylit, floor-heated gallery suitable for studio, workshop or just hanging out. The

  Andrew Edwards Tri Hudson Realty, LLC

  85 Summit St, Philmont, NY 12565
• 

  

  /10

  $320,000

  • Land
  • 9 Acres
  • $36,364 per Acre

  L34&35 County Route 27, Copake, NY 12516

  Wooded 8+ acre building lot in Copake NY. Build your dream home on this spacious, wooded, 8+ acre lot in scenic Copake. Conveniently located just minutes from Copake Lake, Ancram, the Taconic Parkway, and a variety of outdoor and recreational activities. Enjoy peaceful country living with easy access to shopping, dining, and local attractions. A perfect blend of seclusion and convenience.

  Allen Olmsted Canaan Realty

  L34&35 County Route 27, Copake, NY 12516
• 

  

  /8

  $320,000

  • Land
  • 9 Acres
  • $36,364 per Acre

  Lot 34&35 County Route 27, Copake, NY 12516

  Wooded 8+ acre building lot in Copake NY. Build your dream home on this spacious, wooded, 8+ acre lot in scenic Copake. Conveniently located just minutes from Copake Lake, Ancram, the Taconic Parkway, and a variety of outdoor and recreational activities. Enjoy peaceful country living with easy access to shopping, dining, and local attractions. A perfect blend of seclusion and convenience. Land is

  Allen Olmsted Canaan Realty

  Lot 34&35 County Route 27, Copake, NY 12516
• 

  

  /8

  $320,000

  • Land
  • 9 Acres
  • $36,364 per Acre

  Lot34&35 County Route 27, Copake, NY 12516

  Wooded 8+ acre building lot in Copake NY. Build your dream home on this spacious, wooded, 8+ acre lot in scenic Copake. Conveniently located just minutes from Copake Lake, Ancram, the Taconic Parkway, and a variety of outdoor and recreational activities. Enjoy peaceful country living with easy access to shopping, dining, and local attractions. A perfect blend of seclusion and convenience. Land is

  Allen Olmsted Listing by Canaan Realty

  

  Lot34&35 County Route 27, Copake, NY 12516
• 

  

  /13

  $385,000

  • 5 Beds
  • 2 Baths
  • 1,248 Sq Ft

  355 Maple Avenue Extension, Germantown, NY 12526

  1977 Ranch nicely sited on a knoll located at the end of a quiet dead end road less than a half mile from the historic hamlet of Germantown. House features a nice size kitchen with dining area, livingroom overlooking the seasonal mountain views, 3 bedrooms and a full bath on the first floor. The lower level includes a familyroom, 2 additional bedrooms and a full bath as well as workshop/garage

  PATRICIA HINKEIN Patricia A. Hinkein Realty

  355 Maple Avenue Extension, Germantown, NY 12526
• 

  

  /15

  $399,000

  • 4 Beds
  • 4 Baths
  • 2,952 Sq Ft

  2457 State Route 82, Ancram, NY 12502

  Charming Historic Duplex. A Smart Country InvestmentJust two hours north of NYC, this well situated 0.8 acre duplex in Ancram's Historic District offers both immediate rental income and upside through tasteful renovations. Nestled on the Roeliff Jansen Kill, stocked by DEC with trout. This property includes a detached garage, and barn, property combines rustic appeal with strong investment

  Libby McKee Berkshire Hathaway HomeService

  2457 State Route 82, Ancram, NY 12502
• 

  

  /26

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,376 Sq Ft

  3859 County Route 9, East Chatham, NY 12060

  PRICE IMPROVEMENT!! Remodeled sprawling ranch with huge front yard. 3 bedrooms, 2.75 baths. Brand new siding, windows, fridge and stove, flooring, bath fixtures. Freshly painted, spacious and bright. Open concept, set on 35 acres. Heated full basement with a 3/4 bath giving you the opportunity to finish it as you wish. Surround yourself with mature trees and enjoy serene outside living on

  Sharon McArdle Berkshire Hathaway Home Services Blake

  3859 County Route 9, East Chatham, NY 12060
• 

  

  /18

  $345,000

  • 3 Beds
  • 1 Bath
  • 1,352 Sq Ft

  347 W West Hill Rd, New Lebanon, NY 12125

  3BR2BA Ranch on 10 acres with partially finished basement. Great rural setting for getaway, Convenient to skiing. Commute to Albany or Pittsfield. Ski Jiminy

  David Birch Barns & Farms Realty

  347 W West Hill Rd, New Lebanon, NY 12125
• 

  

  /13

  $370,000

  • Land
  • 43 Acres
  • $8,585 per Acre

  L8 Lower Cady Rd, Chatham, NY 12136

  Enjoy this private country property located near a rural historic community. Located just a short drive to the NYS thruway and Mass Pike. Enjoy a short drive to the beautiful Berkshires and Jiminy Peak ski resort. Located minutes to the Taconic State Parkway for a scenic drive to NYC. There are two power poles on property located to the right of the meadow.

  Barry Shatney Bovair Real Estate

  L8 Lower Cady Rd, Chatham, NY 12136
• 

  

  /20

  $314,000

  • 3 Beds
  • 1 Bath
  • 978 Sq Ft

  40 Fairview Ave, Hudson, NY 12534

  This move-in ready, 3-bed 1-bath Hudson cutie has been tastefully updated throughout by an experienced local builder, with gorgeous light-colored hardwood floors, Shaker-style kitchen and bathroom cabinets, quartz countertops, new stainless steel appliances, and other important updates to the mechanical systems. High ceilings give the open-plan living/dining area a light and airy feel, while the

  Carolyn Michelle KW MidHudson

  40 Fairview Ave, Hudson, NY 12534

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