Old Chatham, NY Homes for Sale

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  $999,888

  • 3 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  167 May Hill Rd, Ghent, NY 12075

  A totally unique property unlike any other in Columbia County. This premier hilltop location overlooks the Hawthorne Valley Farm & Waldorf School. Sweeping views of Harlemville and the Taconic mountain range from large picture windows and an expansive 600 sq ft deck. Short stroll on private path through woods to the oldest Waldorf school in the United States and the renowned Hawthorne Valley

  Allen Halstead Berkshire Hathaway HomeService

  167 May Hill Rd, Ghent, NY 12075
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  /43

  $1,120,000

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

  83 May Hill Road Stop 36, Ghent, NY 12075

  Ensconced in greenery, at the end of a quiet country road sits The Dome House: a mahogany-sided passive home that is equal parts function and form, on just over 5 acres. The home is sprawling and airy in nature, and contains a multitude of environments for living, creating, utility and play. Each carefully considered design decision was made in the pursuit of living in harmony with the natural

  Sarah Kardos Four Seasons Sotheby's Int.

  83 May Hill Road Stop 36, Ghent, NY 12075
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  /50

  $799,000

  • 5 Beds
  • 4 Baths
  • 4,052 Sq Ft

  100 Schnackenberg Rd, Ghent, NY 12075

  Beautifully renovated home on 8 private acres in Taconic Hills SD. Offers 5 bedrooms, 4 baths, and a sunlit great room with vaulted ceilings and dual stone fireplaces. The updated kitchen features new cabinets, butcher block counters, and a walk-in pantry. The finished lower level includes 2 bedrooms, full bath, family room, and walkout—perfect for guests or in-laws. Includes an oversized 2-car

  Dominique Wasilewski EXP Realty

  100 Schnackenberg Rd, Ghent, NY 12075
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  /50

  $799,999

  • 5 Beds
  • 4 Baths
  • 4,052 Sq Ft

  100 Schnackenberg Rd, Ghent, NY 12075

  Beautifully renovated home on 8 private acres in Taconic Hills SD. Offers 5 bedrooms, 4 baths, and a sunlit great room with vaulted ceilings and dual stone fireplaces. The updated kitchen features new cabinets, butcher block counters, and a walk-in pantry. The finished lower level includes 2 bedrooms, full bath, family room, and walkout—perfect for guests or in-laws. Includes an oversized 2-car

  Wayne Hartard eXp Realty

  100 Schnackenberg Rd, Ghent, NY 12075
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  /36

  $880,000

  • 3 Beds
  • 2.5 Baths
  • 3,012 Sq Ft

  368 Gahbauer Rd, Hudson, NY 12534

  Welcome to your very own private retreat in the heart of Hudson, New York! Nestled on 8.5 sprawling acres of pristine land, this historic colonial home offers the perfect escape from the hustle and bustle of city life while keeping you just a short 10-minute drive from the vibrant town of Hudson. This home features over 3,000 sqft, 3 bedrooms, and 2.5 baths. Explore your very own wooded

  Dominick DiFilippo Keller Williams Realty Partner

  368 Gahbauer Rd, Hudson, NY 12534
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  /23

  $655,000

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  422 County Route 9, Ghent, NY 12075

  Charming 3-bed, 2-bath craftsman-style farmhouse in Columbia County, fully renovated on 1.5 acres. Borders North Creek and vast open land. Features open-concept living, modern kitchen, primary bedroom with ensuite bath, large deck, and front porch. Bright, airy design with natural light. Minutes from Hudson, Chatham, and Kinderhook for dining, galleries, and outdoor activities. Perfect Hudson

  Rachel Haley Houlihan Lawrence, Inc

  422 County Route 9, Ghent, NY 12075
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  /25

  $625,000

  • 4 Beds
  • 4 Baths
  • 2,676 Sq Ft

  49 Macintosh Dr, Hudson, NY 12534

  Discover Macintosh Drive, bordering historic Philip Apple Orchards, minutes from Hudson, NY—recently celebrated as one of America's coolest small towns. This spacious 2,676 sq ft home features the perfect floor plan for comfortable living. The first floor flows from living room with gas fireplace to formal dining, updated eat-in kitchen, family room, and guest half bath. Second floor: 4 bedrooms

  Martin Salerno The Kinderhook Group, Inc.

  49 Macintosh Dr, Hudson, NY 12534
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  /32

  $547,000

  • 3 Beds
  • 2 Baths
  • 1,729 Sq Ft

  26 Woodland Rd, Craryville, NY 12521

  26 Woodland, Craryville NY ~ 3 (4 with the 'bonus room' upstairs) bedrooms, 2 bath, partially finished basement, great barn w/2nd floor, oversized 2-car heated garage, fruit trees+++. Recent $610,000 appraisal comp. For anyone who has dreamed of a log cabin home in the country, your day has come! Perfectly sited at the crest of a 2-acre lot this gambrel style log home is the complete package. You

  Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

  26 Woodland Rd, Craryville, NY 12521
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  /24

  $625,000

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

  49 Macintosh Dr, Hudson, NY 12534

  Discover Macintosh Drive, bordering historic Philip Apple Orchards, minutes from Hudson, NY—recently celebrated as one of America's coolest small towns. This spacious 2,676 sq ft home features the perfect floor plan for comfortable living.The first floor flows from living room with gas fireplace to formal dining, updated eat-in kitchen, family room, and guest half bath. Second floor: 4

  Martin Salerno The Kinderhook Group, Inc.

  49 Macintosh Dr, Hudson, NY 12534
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  /19

  $395,000

  • 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 Real Estate

  438 Route 217, Hudson, NY 12534
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  /50

  $3,300,000

  • 4 Beds
  • 3 Baths
  • 2,825 Sq Ft

  88 Mac Brown Rd, Claverack-Red Mills, NY 12513

  Welcome to Mac Brown Waterhouse, a storied 119-acre estate set within a hidden valley offering complete seclusion and timeless beauty. The original 1830s farmhouse is tucked away at the end of a private lane in Claverack, NY, where the road terminates in a round gravel driveway anchored by the property’s original stone well. Two large ponds grace the land, one directly in front of the house that

  Anthony D'Argenzio Houlihan Lawrence, Inc

  88 Mac Brown Rd, Claverack-Red Mills, NY 12513
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  /61

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 2,400 Sq Ft

  361 Schnackenberg Rd, Ghent, NY 12075

  An incredible 188 acre property on a highly desirable rural road in the heart of the rolling farmlands of Columbia County. Spectacular west facing views make for incredible sunsets over the Catskill Mountains, the Hudson Valley spreads out beneath them. The acreage includes pastoral farm fields, largely maintained by the neighboring biodynamic farm, forest, and a beautiful swimming pond to cool

  Annabel Taylor Four Seasons Sotheby's Int.

  361 Schnackenberg Rd, Ghent, NY 12075
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  /36

  $222,900

  • 3 Beds
  • 1.5 Baths
  • 1,536 Sq Ft

  57 Main St, Philmont, NY 12565

  Charming Reverse Salt Box Colonial - A Timeless Treasure!Step into history with this unique Reverse Salt Box Colonial, gracefully built in 1883 and brimming with character. Nestled nearby to the serene Agawamuck Creek, this enchanting home offers a rare blend of classic architecture and modern comfort, perfect for those seeking a tranquil getaway or a vibrant community lifestyle.As you enter,

  Barbara Robinson Red Apple Realty

  57 Main St, Philmont, NY 12565
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  /22

  $425,000

  • 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
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  /24

  $255,000

  • 3 Beds
  • 1 Bath
  • 976 Sq Ft

  24 New York 217, Hudson, NY 12534

  Welcome to this inviting 3-bedroom, 1-bath single-family home set on a beautiful, private 1-acre lot in the heart of Hudson.. Nestled on a quiet country road just minutes from downtown Hudson and the Taconic Parkway, this property offers a perfect blend of rural tranquility and accessibility. Step inside to find a bright, functional layout featuring a spacious living room, and a cozy eat-in

  Karen Chung Keller Williams Realty HV Nort

  24 New York 217, Hudson, NY 12534
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  /26

  $255,000

  • 3 Beds
  • 1 Bath
  • 976 Sq Ft

  24 Route 217, Hudson, NY 12534

  Welcome to this inviting 3-bedroom, 1-bath single-family home set on a beautiful, private 1-acre lot in the heart of Hudson.. Nestled on a quiet country road just minutes from downtown Hudson and the Taconic Parkway, this property offers a perfect blend of rural tranquility and accessibility.Step inside to find a bright, functional layout featuring a spacious living room, and a cozy eat-in

  Karen Chung Keller Williams Hudson Valley

  24 Route 217, Hudson, NY 12534
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  /18

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 3,720 Sq Ft

  753 New York 217, Hudson, NY 12534

  For Sale: Speeds Garage - A Rare Commercial Opportunity in the Heart of Claverack. Unlock the potential of this unique property offering both commercial and residential possibilities! Located in a prime, high-visibility spot in Claverack, Speeds Garage has long served the community and continues to be a thriving business since opening in 1982. So whats included? Everything! Indoor and outdoor car

  Heather Davala Davala Real Estate, LLC

  753 New York 217, Hudson, NY 12534
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  /26

  $489,900

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft

  30 Overlook Ct, Hudson, NY 12534

  Accepted Offer 6/6/2025. Continuing to show for backup. Welcome to 30 Overlook Court Set on a quiet cul-de-sac near Claverack town line and within the Village of Philmont, a turnkey three-bedroom, two-bath home with office, central air, propane fireplace, and multiple heating zones. Enjoy a pool, hot tub, mountain views, and oversized two-car garage.Entertain with ease in the spacious dining

  Daniel Mahar Mahar Real Estate, LLC

  30 Overlook Ct, Hudson, NY 12534
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  /20

  $598,000

  • Land
  • 13 Acres
  • $47,460 per Acre

  67 Taconic Creek Rd, Hillsdale, NY 12529

  Set down a secluded 1/8-mile driveway, this 12.6-acre property in the tranquil countryside of Hillsdale offers unmatched privacy and sweeping valley and mountain views. This beautiful home site includes plans for a stunning, modern-country 4,200sq ft main house and a separate 1,700sq ft 3 car garage with studio. Ready to build your dream home, this site provides an ideal canvas for creating your

  Peter Yates Four Seasons Sotheby's Int.

  67 Taconic Creek Rd, Hillsdale, NY 12529
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  /18

  $274,900

  • 2 Beds
  • 2 Baths
  • 794 Sq Ft

  2227 County Route 21, Hillsdale, NY 12529

  Tucked away on over 17 serene, subdividable acres in the Town of Kinderhook, this rare offering includes a half-finished 2-bedroom home (a shell awaiting your vision) with a brand-new raised-bed septic system and drilled well (newer pump) & new pressure tank already in place. With frontage on two quiet country roads; County Route 21 and Fowler Lake Rd. this land is a mix of old stone walls,

  Michael Castellano Gilcrest Properties

  2227 County Route 21, Hillsdale, NY 12529
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  /41

  $739,000

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  292 County Route 27b, Hudson, NY 12534

  Unleash Your Creativity: A Unique Columbia County Retreat with Custom Built Art StudioDiscover an unparalleled opportunity for artists, writers, and creative professionals in the heart of Columbia County, New York. This unique one-acre property offers an extraordinary modern art studio that truly takes center stage, complemented by a beautifully renovated home with income potential.The Studio:

  Reta Meisner Beach & Bartolo Realtors

  292 County Route 27b, Hudson, NY 12534
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  /3

  $110,000

  • Land
  • 5 Acres
  • $21,611 per Acre

  0 Catskill View Rd Unit 157004, Claverack, NY 12513

  A fantastic opportunity! A 5.09-acre lot just outside Claverack, NY, offering a mix of open and wooded land with scenic farmland views. With housing inventory low, this could be the perfect chance to build a home tailored to your vision, rather than settling for someone else's design.The property is conveniently located near the Taconic State Parkway, making travel easy. It does require Board of

  Arleen Shepley Elyse Harney Real Estate

  0 Catskill View Rd Unit 157004, Claverack, NY 12513
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  /10

  $159,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  9 Prospect St, Hudson, NY 12534

  This 3-bedroom, 1 bath row house in the village of Philmont has been updated with new windows, modernized electrical systems, and a substantial amount of plaster and lathe replaced with sheetrock. The home includes a 3-season porch, offering a great space to enjoy the outdoors most of the year, and a small outdoor space with a work or storage shed.Located just minutes from both Hudson and

  Scott Paladino Chatham Properties

  9 Prospect St, Hudson, NY 12534
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  $797,850

  • 3 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  627 State Route 23, Craryville, NY 12521

  Catskill Views, Colonial Charm and Endless Tranquility. Enjoy breathtaking Catskill Mountain views from nearly every room of this meticulously maintained 3-bedroom, 2.5-bathroom colonial-style home set on 13.9 private acres. With 2,456 square feet of living space, this home offers a perfect balance of comfort, style and natural beauty.The sun-filled interior features an open-concept, eat-in

  DeWayne A. Powell William Pitt Sotheby's Int'l

  627 State Route 23, Craryville, NY 12521
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  /33

  $299,000

  • 2 Beds
  • 1 Bath
  • 1,464 Sq Ft

  51 Dunbar Rd, Hudson, NY 12534

  The yard gently rolls up and down between rock outcroppings and clusters of trees creating a canvas true gardeners will appreciate. Nature surrounds this petite farmhouse style with side addition offering a clean slate. Potential in every nook and cranny waiting for the right buyer to accentuate the possibilities. The living room is spacious, has plank wood floors, exposed beam, a 3/4 bath and

  Melinda Barbanti Davala Real Estate, LLC

  51 Dunbar Rd, Hudson, NY 12534
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  /4

  $227,525

  • Land
  • 1.88 Acres
  • $121,024 per Acre

  0 Chestnut Ct, Philmont, NY 12534

  Chestnut Court offers an exceptional development opportunity currently with 8 lots adjacent to a 20-acre conservation area.Located just minutes from the village's amenities, this property is ideally positioned for a residential project.The area boasts a variety of outdoor activities making it highly attractive to potential buyers.Developers can purchase and design a unique subdivision

  Karen Davala Davala Real Estate

  0 Chestnut Ct, Philmont, NY 12534
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  /9

  $32,775

  • Land
  • 0.22 Acre
  • $148,977 per Acre

  66 Chestnut Ct, Claverack, NY 12565

  Chestnut Court offers an exceptional development opportunity with EIGHT individual lots available adjacent to a 20-acre conservation area OR someone can purchase the entire property. Located just minutes from the village's amenities, the area boasts a variety of outdoor activities including the City of Hudson, a sport park, conservation areas, hiking, nearby lakes and quaint boutique shopping.

  Karen Davala Davala Real Estate, LLC

  66 Chestnut Ct, Claverack, NY 12565
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  /4

  $227,525

  • Land
  • 1.88 Acres
  • $121,024 per Acre

  0 Chestnut Ct Unit 156459, Claverack, NY 12565

  Chestnut Court offers an exceptional development opportunity with lots adjacent to a 20-acre conservation area, featuring trails leading to Summit Lake. Located just minutes from the village's amenities including a co-op, deli, pizzeria, and fine dining restaurants. This property is ideally positioned for a residential project.The area boasts a variety of outdoor activities, including the City of

  Karen Davala Davala Real Estate, LLC

  0 Chestnut Ct Unit 156459, Claverack, NY 12565
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  /16

  $365,000

  52 Church St, Hudson, NY 12534

  Welcome to 52 Church St. Tucked in the heart of Philmont, this charming and lovingly restored home is full of warmth and character.Thoughtful updates including a new heating system, roof, electrical, and plumbing ensure comfort and peace of mind for years to come.The home's flexible layout includes a studio apartment, perfect for extra income, a guest suite, or an in-law space.Step inside to a

  Shaina Marron Houlihan Lawrence, Inc

  52 Church St, Hudson, NY 12534
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  /8

  $63,000

  • 3,506 Sq Ft

  4 Ellsworth St, Philmont, NY 12565

  Unlock the potential of this 3,500 sq. ft. handyman special in the heart of Philmont Village! Whether you're an investor, contractor, or visionary, this multi-family zoned property offers endless opportunities. Nestled on a compact .10-acre lot, it's a prime location just seconds from local shops, restaurants, and parks.Bring your tools and creativitythis building is ready for a full

  Heather Davala Davala Real Estate, LLC

  4 Ellsworth St, Philmont, NY 12565
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  /3

  $335,000

  • Land
  • 23 Acres
  • $14,667 per Acre

  0 County Route 21, Hillsdale, NY 12529

  Peaceful Easy Feeling in Hillsdale, New York, near the Massachusetts boarder. This 22+ acre parcel is a blend of an open field, stone walls, mature hardwoods and new growth. There is an identified building location at the back of the open field (left), where there is BOHA (on the survey map).A portion of the field is protected from building, however there is still a generous area for your home --

  Lindsay Lebrecht Copake Lake Realty Corp.

  0 County Route 21, Hillsdale, NY 12529
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  /10

  $2,600,000

  • Land
  • 39 Acres
  • $66,042 per Acre

  873 New York 66, Hudson, NY 12534

  Unlock a Rare Opportunity in Columbia County! Discover 39.369 acres of undeveloped land just 3 miles outside Hudson, NY. Perfectly positioned only 2 hours from NYC and 35 minutes from Albany, the state capital. This property is ideal for industrial, commercial, and residential development, offering unmatched potential. Strategically located 1.6 miles from Columbia County Airport and directly

  Kevin Mullaney eRealty Advisors, Inc.

  873 New York 66, Hudson, NY 12534
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  /40

  $2,995,000

  • 5 Beds
  • 5.5 Baths
  • 7,200 Sq Ft

  35 Harlemville Rd, Hillsdale, NY 12529

  Where Norman charm meets Hudson Valley splendor, "Dragonfly" stands as a fine example of country living - a rare 130-acre estate that marries grand European sophistication with the pastoral beauty of Claverack. Just twenty minutes from the cultural centers of Hudson and the Berkshires, this property strikes a balance between secluded sanctuary and connected countryside living.A winding private

  Chris Getman Houlihan Lawrence Inc.

  35 Harlemville Rd, Hillsdale, NY 12529
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  /26

  $4,150,000

  • 34,576 Sq Ft

  20 Church St, Philmont, NY 12565

  This exclusive opportunity features a portfolio of seven properties in Philmont, NY, offering a mix of residential units across various addresses, all within a few block radius. The seller, a seasoned investor, prefers to sell the portfolio as a whole, though individual sales are possible. This portfolio offers an immediate income-generating investment with a projected NOI of $358,022. With a mix

  Rachel Haley Houlihan Lawrence Inc.

  20 Church St, Philmont, NY 12565
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  /19

  $364,000

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  677 Route 66, Hudson, NY 12534

  Great 3 Bedroom 1 Bath Ranch large lot, 2 car detatched Garage. Minutes to Hudson, Skiing Amtrak, Riverfront Marina and Park. Receent improvements, New roof on house,New submersible well pump, Upgrades and fresh paint to garage.

  Bob Kavanaugh Barns & Farms Realty, LLC

  677 Route 66, Hudson, NY 12534
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  /33

  $309,900

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  6154 New York 9h, Claverack-Red Mills, NY 12513

  Charming residence situated in the Town of Claverack, nestled in the picturesque Columbia County, offering convenient access to Albany, Boston, and New York City. Experience the myriad attractions this region presents, such as the renowned Olde York Farm Distillery & Cooperage, the Mill at Green Hole, and the Columbia Golf and Country Club. The property is in close proximity to Hudson, NY, where

  Justin Phillips United RE Hudson Valley Edge

  6154 New York 9h, Claverack-Red Mills, NY 12513
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  /9

  $395,000

  • Land
  • 22 Acres
  • $18,287 per Acre

  0 Texas Hill Rd, Hillsdale, NY 12529

  This beautiful lot with breathtaking views is waiting for you to come build your dream home, exactly how you want it. With over 20 acres of raw, wooded land, you can create a compound of homes with your family or friends, or build a possible subdivision. This property offers the privacy you're looking for while still being close to town. Minutes from Route 23 and Taconic Hills School.

  Ronald Green KW MidHudson

  0 Texas Hill Rd, Hillsdale, NY 12529
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  /6

  $15,000

  • Land
  • 1.50 Acres
  • $10,000 per Acre

  0 Route 23 Rd, Copake, NY 0

  ideal small lot on Route 23 with lots of traffic, zoned residential, but commercial use possible with property approvals. Back of property is wet. Broker owned

  David Birch Barns & Farms Realty, LLC

  0 Route 23 Rd, Copake, NY 0
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  /14

  $299,000

  • Land
  • 10 Acres
  • $30,448 per Acre

  4 Darling Rd, Hillsdale, NY 12529

  Lot 4: Level land with few trees. Beautiful far stretching view of the valley to the south. A short 5 minute drive from the Taconic State Parkway, tucked up on a mountainside with great views of the valley. Untouched and unencumbered, this former farmland land has gentle slopes, no archaeological issues or no endangered species. Ready for building. Other neighboring lots available totaling 66.45

  John Barbato Compass, Hillsdale

  4 Darling Rd, Hillsdale, NY 12529
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  /20

  $1,245,000

  • Land
  • 50 Acres
  • $24,653 per Acre

  7 Darling Rd, Hillsdale, NY 12529

  A short 5 minute drive from the Taconic State Parkway, tucked up on a mountainside with incredible far-reaching panoramic views of the Catskills and the Hudson Valley. Untouched and unencumbered, this former farmland has no archaeological issues or no endangered species. Stone walls and gentle slopes. Ready for building. Divided into 5 lots of varying sizes. Sell off the lots one by one, or keep

  John Barbato Compass, Hillsdale

  7 Darling Rd, Hillsdale, NY 12529

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