Hillsdale, NY Homes for Sale

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  /7

  $15,900

  • Land
  • 1.00 Acre
  • $15,900 per Acre

  0 Holm Rd, Hillsdale, NY 12529

  Own Land A Tangible Asset That Lasts!Secure your future with real, lasting land ownership!This affordable 1-acre lot in Hillsdale, Columbia County, NY, offers a rare opportunity. Property Highlights: Grandfathered Build Rights:-New zoning requires 3 acres this 1-acre lot is grandfathered and eligible for building pending buyer research and approvals. Bonus

  Cathy Nation

  0 Holm Rd, Hillsdale, NY 12529
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  /44

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 3,282 Sq Ft

  9960 New York 22, Hillsdale, NY 12529

  Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat.The grand

  Pamela King-Belfor Four Seasons Sotheby's Int.

  9960 New York 22, Hillsdale, NY 12529
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  /50

  $3,199,000

  • 4 Beds
  • 4.5 Baths
  • 4,635 Sq Ft

  211 Mitchell St, Hillsdale, NY 12529

  Elevate Your Lifestyle in Columbia CountyDiscover the pinnacle of modern luxury in this extraordinary Columbia County estate, set against the breathtaking backdrop of the Berkshire Hills and Catamount Mountains. Spanning over 10 meticulously landscaped acres, this architectural gem blends serene country living with sophisticated design.Step into a grand double-height foyer that

  Christopher Halliburton Beach & Bartolo Realtors

  211 Mitchell St, Hillsdale, NY 12529
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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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  /25

  $1,575,000

  • 4 Beds
  • 4.5 Baths
  • 3,024 Sq Ft

  83 Schmeichel Rd, Hillsdale, NY 12529

  A Home of Distinction -- there are two distinct sections of this 4+ BR, 4.5 BA, 2 office spaces, 3,666 sf home that is sited on 18.5 private acres. Wood-burning fireplace, 2 gas wood stoves. Pond with gazebo. The main section has 3 BR's, living room, family room, eat-in kitchen, access to the deck with Catamount views and an attached 2-car garage. The addition has a welcoming entrance, 1 BR.

  Lindsay Lebrecht Copake Lake Realty Corp.

  83 Schmeichel Rd, Hillsdale, NY 12529
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  /25

  $1,495,000

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  161 Stagecoach Rd, Hillsdale, NY 12529

  Architecture meets nature in Hillsdale. A fully secluded getaway at the end of a private dead-end road on 7.3 pristine acres. This sunny 3-bedroom, 2-1/2 bath house is inspired by Scandinavian design and features 3 outdoor decks, with views of a spring-fed stream, a crystal clear pond, and deep green woodlands. Central AC for summer days and a wood stove for snowy nights. An ideal layout

  Owen Davidson Brown Harris Stevens HV LLC

  161 Stagecoach Rd, Hillsdale, NY 12529
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  /38

  $1,100,000

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

  110 Meadow Ln, Hillsdale, NY 12529

  Ultra-private dead-end lot overlooking Hillsdale, this extraordinary home offers some of the most breathtaking panoramic views in the entire Hudson Valley. Set on 11.9 totally private acres, the property is a rare combination of refined living and natural serenity, with a gentle stream meandering below and a charming footbridge crossing over—straight out of a storybook. There is even a pond with

  Michael Castellano Gilcrest Properties

  110 Meadow Ln, Hillsdale, NY 12529
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  /20

  $1,100,000

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft

  75 Upper Hollow Rd, Hillsdale, NY 12529

  Nestled along a picturesque, secluded country dirt road--surrounded by a serene pond, a flowing creek, and wooded acreage--this charming 2 bedroom log cabin offers the perfect escape. The expansive property spans 193 acres, with 18 acres located outside the Columbia Land Conservancy and Forestry Program, allowing for reduced taxes and enhanced privacy.An additional structure on the

  Janet Kain The Kinderhook Group, Inc.

  75 Upper Hollow Rd, Hillsdale, NY 12529
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  /39

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 2,834 Sq Ft

  11 Cold Water St, Hillsdale, NY 12529

  This stately Greek Revival sits proudly on a generous village lot in the historic Hamlet of Hillsdale. Dating back to c.1848, the home boasts beautiful architectural proportions and details. Pilasters accent the exterior corners of the house and a front- and side-gabled roof add additional grandeur. Arrive via a front porch — running the full width of the façade — framed with Doric columns. The

  MATTHEW CAREY Rouse + Co Real Estate, LLC

  11 Cold Water St, Hillsdale, NY 12529
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  /46

  $2,450,000

  • 2 Beds
  • 2 Baths
  • 2,755 Sq Ft

  292 White Hill Ln, Hillsdale, NY 12529

  Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side brings in the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  292 White Hill Ln, Hillsdale, NY 12529
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  /45

  $1,268,500

  • 2 Beds
  • 3.5 Baths
  • 1,700 Sq Ft

  401 Collins Street Stop 11, Hillsdale, NY 12529

  A Visionary Masterpiece in Columbia County Redefining Country Living. Tucked away on over four serene, wooded acres along one of Columbia County's most coveted roads, this extraordinary 1,700-square-foot contemporary barn home is an architectural work of art a one-of-a-kind residence conceived and crafted by acclaimed designer Angela Patterson. Marrying bold architectural innovation with the

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

  401 Collins Street Stop 11, Hillsdale, NY 12529
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  /15

  $1,095,000

  • 4 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  25 Nobletown Rd, Hillsdale, NY 12529

  Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim

  Andrew Gates Houlihan Lawrence

  25 Nobletown Rd, Hillsdale, NY 12529
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  /31

  $1,600,000

  • 3 Beds
  • 3.5 Baths
  • 2,108 Sq Ft

  181 Lockwood Rd, Craryville, NY 12521

  Set on a sprawling 6 acres, up a private driveway, off a quiet road, this sophisticated 2100 sq ft home ( 3 BR, 3.5 baths) was recently renovated for a turn key experience. Open floor plan on the first floor with natural light streaming through oversized windows. Vaulted ceilings. Chef's kitchen with island, quartz countertops, custom cabinetry, farmhouse sink, Bertozzoni stove, Miele

  Beth Cozzolino Gabel Real Estate

  181 Lockwood Rd, Craryville, NY 12521
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  /18

  $540,000

  • 2 Beds
  • 2 Baths
  • 1,493 Sq Ft

  2253 County Route 21, Hillsdale, NY 12529

  Introducing the Kinderhook Cabin, a well cared-for home where every detail has been thoughtfully considered and hand-finished by a master carpenter. Built in 2021, this ranch-style residence offers easy one-level living, a rustic-modern aesthetic and plenty of privacy, set on 5 acres along a beautiful winding country road between Kinderhook and Ghent. Step inside to a large entry hall

  Jeffries Blackerby Houlihan Lawrence Inc.

  2253 County Route 21, Hillsdale, NY 12529
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  /7

  $595,000

  • Land
  • 30 Acres
  • $19,833 per Acre

  0 Labranch Unit 20252234, Hillsdale, NY 12529

  Wonderful southern exposure on one of the most scenic byways in Columbia County. Large parcels and restrictive covenants on abutting land. High fields and ancient tree lines dotted with maples and old stone walls. Nice mix of open and wooded to tuck your home into the hedge row without another home in site. Distant views of Catamount Mountain. Close to Hawthorne Valley School and the Berkshires.

  Tracy Tassinari Gabel Real Estate

  0 Labranch Unit 20252234, Hillsdale, NY 12529
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  /38

  $649,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  47 Cherokee Dr, Hillsdale, NY 12529

  Kick off your flip flops and enjoy lake life. Tucked above Copake Lake in Hillsdale, NY, Lakelight is a freshly renovated chalet with deeded lake access, two sunny decks, and something most lake houses don't offer: privacy. This isn't a shoulder-to-shoulder shoreline setup. You've got space, trees, light, and breathing room—with the water just two minutes away down a quiet private road.Set on a

  Arlena Armstrong Anatole House LLC

  47 Cherokee Dr, Hillsdale, NY 12529
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  /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
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  /31

  $1,695,000

  • Land
  • 127 Acres
  • $13,336 per Acre

  0 Mitchell St Unit 20251360, Hillsdale, NY 12529

  Mitchell St is one of the most picturesque roads in Hillsdale and this property has a beautiful gentleness to it. Comprising of three separate contiguous lots (35.2 acres, 43.1 acres and 48.8 acres per assessor); access comes in off the southern most lot (43.10) and meanders through the property by a pond site, open meadows, old fruit trees and views of the hills around. The middle lot takes you

  Jennifer Harvey Compass Greater NY LLC

  0 Mitchell St Unit 20251360, Hillsdale, NY 12529
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  /19

  $875,000

  • Land
  • 150 Acres
  • $5,833 per Acre

  0 Overlook Dr, Hillsdale, NY 12529

  Situated in Hillsdale, this 150-acre wooded parcel offers an excellent development opportunity with potential for panoramic views of the Berkshires, Taconic Range, and/or the Catskill Mountains. Established logging roads and trails meander through the property, revealing historic stone walls, rock outcroppings, seasonal streams, and charming waterfalls. The site is currently enrolled in a

  MATTHEW CAREY Rouse + Co Real Estate LLC

  0 Overlook Dr, Hillsdale, NY 12529
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  /19

  $875,000

  • Land
  • 150 Acres
  • $5,833 per Acre

  400 Overlook Dr, Hillsdale, NY 12529

  Situated in Hillsdale, this 150-acre wooded parcel offers an excellent development opportunity with potential for panoramic views of the Berkshires, Taconic Range, and/or the Catskill Mountains. Established logging roads and trails meander through the property, revealing historic stone walls, rock outcroppings, seasonal streams, and charming waterfalls. The site is currently enrolled in a

  MATTHEW CAREY Rouse + Co Real Estate, LLC

  400 Overlook Dr, Hillsdale, NY 12529
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  /22

  $1,695,000

  • Land
  • 127 Acres
  • $13,346 per Acre

  0 Mitchell St Unit 246335, Hillsdale, NY 12529

  Mitchell St is one of the most picturesque roads in Hillsdale and this property has a beautiful gentleness to it. Comprising of three separate contiguous lots (35.2 acres, 43.1 acres and 48.8 acres per assessor); access comes in off the southern most lot (43.10) and meanders through the property by a pond site, open meadows, old fruit trees and views of the hills around. The middle lot takes you

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  0 Mitchell St Unit 246335, Hillsdale, NY 12529
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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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  /24

  $845,000

  • 6 Beds
  • 2 Baths
  • 2,998 Sq Ft

  60 Anthony St, Hillsdale, NY 12529

  Price reduction.1800s farm house. Just waiting for some TLC. This property consists of the main farm house. one very large barn. Addtional 3 out building. One of the back building contains an attractive apartment.The property butts up to the Harlem Valley Rail Trail. Walking distant to the Hamlet of Hillsdale. Including the Roe Jan Brewing Co. IGA, The Hillsdale House, The town park. Less then 5

  Gerard Meenagh The Meenagh Group Realty

  60 Anthony St, Hillsdale, NY 12529
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  /17

  $499,000

  • Land
  • 83 Acres
  • $5,996 per Acre

  50 - 61 Dugway Rd, Hillsdale, NY 12529

  Two Large Parcels Combine Offering Serenity & Great Potential. Located between the charming towns of Chatham, NY, and Great Barrington, MA, this 83 acre parcel offers you exceptional potential awaiting your vision, and ideal escape.Two adjoining proprieties come together to form this large property that is a unique blend of privacy and accessibility. Enjoy impressive road frontage on two roads

  Jeffrey McKinney Beach & Bartolo Realtors

  50 - 61 Dugway 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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  /9

  $220,000

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft

  10011 New York 22, Hillsdale, NY 12529

  Centrally located in Hillsdale, Columbia County, NY. Just about equal distance to Great Barrington, MA and Hudson, NY.This three bedroom, one bathroom, 1,000+ sf home offers a great level yard and a view of your own pond!The area is full of activities such as found at Catamount, the Harlem Valley Rail Trail (nothing motorized), Tanglewood, Copake Country Club, Copake Lake, organic farms, farmer

  Theresa Westlake Copake Lake Realty Corp.

  10011 New York 22, Hillsdale, NY 12529
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  /10

  $200,000

  • Land
  • 15 Acres
  • $13,324 per Acre

  0 Holm Rd, Hillsdale, NY 12529

  This 15-acre vacant land presents a unique opportunity for investment or development. Located next to 84 Holm Rd and directly across from the Columbia County Solid Waste Station (Hillsdale Convenience Station), the land offers easy access while maintaining privacy. With scenic views of the rolling hills and open fields, it’s ideal for a farmhouse, agricultural use, or a private retreat. The land

  Derek Greene Greene Realty Group

  0 Holm Rd, Hillsdale, NY 12529
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  /19

  $799,000

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  30 Ridge Ln, Hillsdale, NY 12529

  Ridge Lane in Hillsdale is the perfect country retreat. Set on 7+ acres on a quiet dead end road. This newly built farmhouse captures the charm and solitude that make Hillsdale so desired. Come in to the mudroom, kick off your shoes and enjoy the space of a real country kitchen. The open living space flows easily to the dining area and living room or out to the deck to enjoy the blue sky. An

  Emma French Gabel Real Estate

  30 Ridge Ln, Hillsdale, NY 12529
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  /3

  $299,000

  • Land
  • 23 Acres
  • $13,091 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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  /15

  $199,000

  • Land
  • 8 Acres
  • $25,254 per Acre

  0 Whippoorwill Rd, Hillsdale, NY 12529

  Perfect Country Retreat — Build Your Dream Home in HillsdaleEscape to the tranquility of the Hudson Valley with this beautiful, private parcel just minutes from the heart of charming Hillsdale. Set on a quiet, scenic road ideal for walking, jogging, or simply enjoying the peaceful surroundings, this land offers both tranquility and convenience.Enjoy seasonal views of Catamount Ski

  Leigh Bahnatka BHHS Hudson Valley Properties

  0 Whippoorwill Rd, Hillsdale, NY 12529
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  $8,850,000

  • 4 Beds
  • 4.5 Baths
  • 6,438 Sq Ft

  890 Bald Mountain Rd, Austerlitz, NY 12017

  Welcome to The Bald Mountain Estate, the premier family compound in the Upper Hudson Valley. What sets this property apart as one of the most invaluable parcels in the area, is the land- unique, secluded, and beautifully rugged. Inside a gated area of large acreage estates, this 4 building architectural masterpiece property sits on 85 private acres, with multiple trails and an additional building

  Rachel Haley Houlihan Lawrence Inc.

  890 Bald Mountain Rd, Austerlitz, NY 12017
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  /18

  $3,630,000

  • Land
  • 242 Acres
  • $15,000 per Acre

  2 Dugway Rd, Austerlitz, NY 12017

  242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

  Michael Tellerday Houlihan Lawrence, Inc.

  2 Dugway Rd, Austerlitz, NY 12017
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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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  /15

  $3,630,000

  • Land
  • 242 Acres
  • $15,000 per Acre

  00 Dugway Rd, Austerlitz, NY 12017

  242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

  Michael Tellerday Houlihan Lawrence Inc.

  00 Dugway Rd, Austerlitz, NY 12017
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  /6

  $199,000

  • Land
  • 33 Acres
  • $5,974 per Acre

  50 Dugway Rd, Hillsdale, NY 12529

  Create Your Own VisionEscape to 33.31 acres of untouched beauty nestled between Columbia County, NY, and Great Barrington, MA. This stunning parcel of wooded land offers complete privacy with no neighbors in sight just you and the tranquility of nature.Imagine the possibilities as you explore the lush, wooded landscape teeming with wildlife. With over 1,677 feet of road frontage, access is easy.

  Jeffrey McKinney Beach & Bartolo Realtors

  50 Dugway Rd, Hillsdale, NY 12529
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  /13

  $325,000

  • Land
  • 50 Acres
  • $6,512 per Acre

  61 Dugway Rd, Hillsdale, NY 12529

  Discover Your Dream Retreat: 49+ Acres of Serenity and Potential!Nestled between the charming towns of Chatham, NY, and Great Barrington, MA, this stunning parcel of over 49 acres offers a unique blend of privacy and accessibility. With impressive road frontage on two roads, this property is easily accessible while still providing a tranquil escape.Imagine waking up to the soothing sounds of the

  Jeffrey McKinney Beach & Bartolo Realtors

  61 Dugway Rd, Hillsdale, NY 12529
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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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  /36

  $449,900

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft

  69 SW Colony Rd, Hillsdale, NY 12529

  A Lake house in the country is perfect for those seeking a simple way of life. You'll feel like you're living in a storybook. Watch your story unfold before your eyes. Leona's Country Cottage is not your average cottage. It was architecturally designed and built to last many years to come. A new rebuild from the foundation up between 2020-2021 With all new requirements for efficiency and new code

  Michelle Ayala BHHS Hudson Valley Properties

  69 SW Colony Rd, Hillsdale, NY 12529
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  /33

  $665,000

  • 3 Beds
  • 2 Baths
  • 2,057 Sq Ft

  2657 New York 23, Hillsdale, NY 12529

  Turnkey Historic Home, Fully Renovated, No Work NeededThis 1810 Greek Revival in Hillsdale has been completely gut-renovated, offering historic charm with none of the hassle. With rising construction costs and new U.S. tariffs driving up renovation expenses. This move-in-ready home is a smart, stress-free investment.All major systems are brand new: HVAC, plumbing, water filters,

  Pamela King-Belfor Four Seasons Sothebys Intl

  2657 New York 23, Hillsdale, NY 12529
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  /41

  $2,495,000

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

  250 Island Dr, Craryville, NY 12521

  Rarely available private gated island property, offered below market value.Sought after and water-front home on a private island in the middle of the only high-speed motor boat lake in Columbia County. A modern lake cottage and carriage house on 1.1 acres with four-season hot tub, large private dock and over 100ft of direct water frontage.The main house has 2 proper bedrooms and 2 full bathrooms,

  John Barbato Compass, Hillsdale

  250 Island Dr, Craryville, NY 12521

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