Hillsdale, NY Homes for Sale

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  /39

  $2,895,000

  • 5 Beds
  • 7 Baths
  • 4,645 Sq Ft

  42 Golf Course Rd, Craryville, NY 12521

  Discover the epitome of quiet luxury in this custom-designed lake home by the renowned New York design duo, Meyer Davis, nestled in the vibrant Copake Lake community. As you enter through the gates, you're welcomed into a relaxed and serene getaway. The open-concept main level features a primary bedroom en-suite with a soaking tub and luxuriously tiled shower; a kitchen complete with a pantry; a

  

  Veronica Newton

  Compass Greater NY, LLC

  (518) 333-3956

  42 Golf Course Rd, Craryville, NY 12521
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  /4

  $289,900

  • 7 Beds
  • 3 Baths
  • 2,578 Sq Ft

  2605 State Route 23, Hillsdale, NY 12529

  The George and Harriet Sornberger House dates back to the 1870's and is sited among historic homes in Hillsdale, NY. Renovation had started; many original details remain. Last use was a three-unit building, however, it could be restored to a one-family home.Seller financing, including renovation costs, negotiable.

  

  Lindsay Lebrecht

  Copake Lake Realty Corp.

  (518) 809-8328

  2605 State Route 23, Hillsdale, NY 12529
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  /3

  $350,000

  • Land
  • 23 Acres
  • $15,324 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.

  (518) 672-6693

  0 County Route 21, Hillsdale, NY 12529
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  /57

  $1,195,000

  • 3 Beds
  • 2.5 Baths
  • 1,931 Sq Ft

  523 Breezy Hill Rd, Hillsdale, NY 12529

  Well maintained ranch set on 8.3 open acres with beautiful views of the Taconic Range. The home with 3 bedrooms and 2.5 baths is lovely as is, and offers excellent possibilities for future additions. Enjoy expansive mountain views from both the open living space and the primary bedroom. A large deck provides great outdoor living/dining space, mature gardens and landscaping finish the property

  Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  523 Breezy Hill Rd, Hillsdale, NY 12529
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  /28

  $1,185,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  228 County Road 21, Hillsdale, NY 12529

  Set amongst the rolling hills of southern Columbia County, this c1942 antique farmhouse sits on seven acres with beautiful, pastoral views down the valley to the east. There is a separate studio, a three car garage and a potting shed on the property. Renovated top-to-bottom, the main house has both old world charm with its original hardwood floors, and modern comforts like new windows and roof,

  Annabel Taylor Four Seasons Sothebys Intl

  228 County Road 21, Hillsdale, NY 12529
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  /32

  $1,295,000

  • 3 Beds
  • 2.5 Baths
  • 2,194 Sq Ft

  17 White Hill Rd, Hillsdale, NY 12529

  Secluded Hillsdale Contemporary on 27.7 acres with incredible far reaching views. Located off a scenic country road, the long private driveway leads to this 2200 square foot home. Originally built in 1970, the house has been upgraded with new windows and sliding doors which create walls of glass for enjoying the natural beauty of the surrounding landscape. The house features 3 bedrooms, 2.5

  PATRICIA HINKEIN Patricia A. Hinkein Realty

  17 White Hill Rd, Hillsdale, NY 12529
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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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  /45

  $1,335,000

  • 2 Beds
  • 1,700 Sq Ft

  401 Collins Street Stop 11, Hillsdale, NY 12529

  Now You Can See Around Corners: Discover this extraordinary one-of-a-kind 1,700-sf octagonal contemporary barn home, conceived and built by its visionary owner, architectural designer Angela Patterson, and tucked away on more than four acres of woodlands on one of the most desirable streets in Columbia County. Boasting huge, pivoting picture windows that invite a flood of natural light and

  DeWayne A. Powell William Pitt Sothebys Intn'l

  401 Collins Street Stop 11, Hillsdale, NY 12529
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  /17

  $1,270,000

  • 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.

  Andrew Gates HOULIHAN LAWRENCE, INC

  25 Nobletown Rd, 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 Greater NY LLC

  250 Island Dr, Craryville, NY 12521
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  /57

  $3,350,000

  • 5 Beds
  • 7 Baths
  • 5,667 Sq Ft

  32 Oxbow Rd, Egremont, MA 01230

  This spacious stunning home is a true masterpiece! Set on 13+ acres w/ breathtaking mountain and pastoral views, complemented by a vast open sky. The open floor plan and expansive windows create a seamless flow between the indoor and outdoor spaces. Gourmet kitchen, great room, formal dining & living rooms are ideal for hosting gatherings. Five en suite bedrooms, including two luxurious primary

  Molly Thomas COMPASS MASSACHUSETTS , LLC GB

  32 Oxbow Rd, Egremont, MA 01230
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  /44

  $2,475,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 3,886 Sq Ft

  49 Sky Top Rd, Copake, NY 12516

  The Nine-Square House was born of a several-year-long collaboration between multi-disciplinary artist Zak Kitnick & esteemed architect Francesco Galetto. At its core, an authentic country house, it joins & (and is inspired by) the vernacular of brutalist mid-century villas peppered throughout German, Austrian, & Scandinavian rural landscapes. The home is minimalist in structure so that it may

  Raj Kumar Four Seasons Sotheby's Int.

  49 Sky Top Rd, Copake, NY 12516
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  /40

  $759,000

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft

  161 Stone Ledge Rd, Hillsdale, NY 12529

  Tucked away on a quiet, secluded backroad, this striking contemporary home offers the perfect blend of privacy, modern design, and convenience. With three thoughtfully designed levels, the main house features 4 bedrooms and 3 recently updated full bathrooms, providing ample space for both everyday living and entertaining.The top floor is dedicated to the serene primary suite, featuring a spacious

  161 Stone Ledge Rd, Hillsdale, NY 12529
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  /32

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft

  58 Deer Track Ln, Hillsdale, NY 12529

  Authentic Hillside Haven with Mountain ViewsMorning light streams through the wide bay window of this classic mid-century ranch, revealing the ridge of mountains beyond and even a glimpse of Catamount Ski area in the distance. On special mornings, you might witness what the current family calls a ''Martian Dawn Sunrise,'' when the distant mountains glow a magnificent red - a rare spectacle

  Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  58 Deer Track Ln, Hillsdale, NY 12529
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  /18

  $569,000

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft

  676 County Route 21, Ghent, NY 12075

  Private and Quiet 19+ Acres Surround this Hidden Contemporary Single-level Home. Built with pride and love by the skillful carpenter owner with a soothing stream included. Two bedrooms with large windows allowing one to take in the beauty of the setting and offering seasonal Catskill Mountain views to the west. Sunny and bright kitchen with skylights and glass sliding doors leading to a

  Terry Cozzolino Cozzolino Real Estate Inc

  676 County Route 21, Ghent, NY 12075
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  /10

  $199,000

  • Land
  • 15 Acres
  • $13,258 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.

  Derek Greene Greene Realty Group

  0 Holm Rd, Hillsdale, NY 12529
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  /14

  $849,000

  • 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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  /5

  $199,000

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

  0 Whippoorwill Rd, Hillsdale, NY 12529

  Build your dream home!! Great road for running or strolling. Very close to the center of Hillsdale. Close to Hawthorne Valley and skiing at Catamount. You can see Catamount from the road. Incredible houses up and down the road. Land is very private and where the potential home could be built is very protected. Perc test was done. If coming from 22 it is 1.8 miles and will be before the

  Leigh Bahnatka BHHS Hudson Valley Properties

  0 Whippoorwill Rd, Hillsdale, NY 12529
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  /9

  $289,000

  • 3 Beds
  • 3 Baths
  • 2,304 Sq Ft

  9249 State Route 22, Hillsdale, NY 12529

  Mixed Residential/Commercial building, with 2 or 3 rentable spaces. Current RR $36,000. One side of building has commercial reception area down and 1BR apartment above. Rental $1400/m. Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is $875 + $550. Or could be rented to same party for live/work. Building in excellent

  David Birch Barns and Farms Realty LLC

  9249 State Route 22, Hillsdale, NY 12529
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  /7

  $279,000

  • 3 Beds
  • 3 Baths
  • 2,304 Sq Ft

  9249 Route 22 Rd, Hillsdale, NY 12516

  Mixed Residential/Commercial building, with 3 rentable spaces. Current RR $30,540. One side of building has commercial reception area down and 1BR apartment above. Rental $1250/m (month-to- month, should be 1450 on lease). Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is $895 + $400 ( should be $550). Ideal for

  David Birch Barns & Farms Realty, LLC

  9249 Route 22 Rd, Hillsdale, NY 12516
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  /12

  $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

  67 Taconic Creek Rd, Hillsdale, NY 12529
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  $8,950,000

  • 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

  2 Dugway Rd, Austerlitz, NY 12017
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  /17

  $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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  /18

  $5,930,000

  • Land
  • 517 Acres
  • $11,470 per Acre

  4 W Hill Rd, Austerlitz, NY 12017

  517 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.

  4 W Hill Rd, Austerlitz, NY 12017
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  /7

  $725,000

  • Land
  • 30 Acres
  • $24,167 per Acre

  0 Labranch Unit 155115, 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.

  0 Labranch Unit 155115, Hillsdale, NY 12529
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  /13

  $370,000

  • Land
  • 50 Acres
  • $7,413 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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  /6

  $270,000

  • Land
  • 33 Acres
  • $8,106 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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  /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 Open Sun 12PM - 2PM

  • 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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  $714,500 Open Sat 12:30PM - 2:30PM

  • 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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  /8

  $99,000

  • Land
  • 6 Acres
  • $16,500 per Acre

  76 New York 71, Hillsdale, NY 12529

  Six acres of prime land on NY-Berkshire border. Discover your dream escape with is exceptional six-acre parcel. This property offers a rare opportunity to build your custom home or vacation retreat in an area know for its natural beauty and tranquility. Enjoy easy access to the culture and recreational amenities of the Berkshires, and the vibrant local communities of New York's Hillsdale,

  Rochelle Bartolo Beach & Bartolo Realtors

  76 New York 71, Hillsdale, NY 12529
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  /13

  $1,080,000

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

  0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529

  Picturesque farmland located close to the Village of Hillsdale, only 1.8 to Catamount Ski Area, and 9.5 miles to Great Barrington. Extensive road frontage, totaling 3979 feet on Yonderview Road and Route 23. Barn complex. This parcel is zoned RU in the Town of Hillsdale. Property currently enjoys an agricultural exemption. Survey available. Inspect Now!

  Robert D Ferris R. Ferris Real Estate, LLC

  0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529
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  /15

  $325,000

  • Land
  • 8 Acres
  • $40,932 per Acre

  2 Darling Rd, Hillsdale, NY 12529

  Lot 2: Catskill mountain and far reaching value views! 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 acres. New road to access the land is

  John Barbato Compass Greater NY LLC

  2 Darling Rd, Hillsdale, NY 12529
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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 Greater NY LLC

  4 Darling Rd, Hillsdale, NY 12529
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  /20

  $1,495,000

  • Land
  • 66 Acres
  • $22,498 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, a serene pond and gentle slopes. Ready for building. Divided into 7 lots (6 of which are buildable) of varying

  John Barbato Compass Greater NY LLC

  7 Darling Rd, Hillsdale, NY 12529
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  /9

  $829,000

  • Land
  • 57 Acres
  • $14,569 per Acre

  3244 Cr 7, Hillsdale, NY 12529

  Stonegate Hill is 56+ private acres with views of Copake Lake and Catskill Mountain sunsets. After entering the gates, the tree-lined driveway meanders to the sweet spot.Equidistant to Hudson, NY and Great Barrington, MA., there is so much the area has to offer. From Catamount Ski/Adventure Park to Tangelwood, come explore the area. Copake Lake and Copake Country Club are 5 minutes away.Amtrak,

  Theresa Westlake Copake Lake Realty Corp.

  3244 Cr 7, Hillsdale, NY 12529
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  /20

  $660,000

  • 1,080 Sq Ft

  15 Roosevelt Dr, Hillsdale, NY 12529

  This is absolutly charming. All on one floor with a covered porch. Looks straight towards Copkae Lake with it's own dock. Has it's own septic. 1000 Gal with Leach Fielld.

  Donna Peck Copake Realty

  15 Roosevelt Dr, Hillsdale, NY 12529
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  /40

  $649,000

  • Land
  • 40 Acres
  • $16,124 per Acre

  209 Anthony St, Hillsdale, NY 12529

  Price Reduction! Incredible Development Opportunity in Hillsdale, NY - 40.25 Acres of Potential Now offered at a reduced price, this expansive 40.25-acre parcel in the charming Hamlet of Hillsdale, NY, presents an incredible opportunity for developers, nature lovers, or those seeking the perfect spot to build their dream home (or homes). With its ideal location, natural beauty, and proximity to

  Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  209 Anthony St, Hillsdale, NY 12529
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  /19

  $4,250,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 6,124 Sq Ft

  250 Island Dr, Craryville, NY 12521

  New construction home on a private gated island with the possibility to customize further for 2026 completion.Exclusive location on a private island in the middle of the only water ski motor boat lake in Columbia County. A contemporary house on 1.1 acres with a large private dock and over 120ft of direct water frontage on Lake Copake. This beautiful home has 5 proper bedrooms (with the

  John Barbato Compass Greater NY LLC

  250 Island Dr, Craryville, NY 12521

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