Hillsdale, NY Homes

• 

  Est $792,000 Not Listed For Sale

  0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529

  • 4 Beds
  • Built 1960

  0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529

  Last Sold Summary

  • 164% Above List Price
  • $337/SF
  • 219 Days On Market

  Last Sold Price $300,000

  Last Listing Agent Robert D Ferris R. Ferris Real Estate, LLC
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  /37

  $695,000 New Construction

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

  30 Ridge Ln, Hillsdale, NY 12529

  Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town. Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in mind.

  John Barbato Compass, Hillsdale

  30 Ridge Ln, Hillsdale, NY 12529
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  /41

  $786,000 Sold Nov 20, 2025

  441 Overlook Dr, Hillsdale, NY 12529

  • 3 Beds
  • 3 Baths
  • 1,875 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Below List Price
  • $419/SF
  • 50 Days On Market

  Current Estimated Value $772,583

  Last Listing Agent Jennifer Harvey Compass Greater NY LLC

  441 Overlook Dr, Hillsdale, NY 12529
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  /10

  Not Listed For Sale

  10344 New York 22, Hillsdale, NY 12529

  • 5 Beds
  • 2 Baths
  • Built 1875

  10344 New York 22, Hillsdale, NY 12529

  Last Sold Summary

  • $549/SF
  • 281 Days On Market

  Last Sold Price $1,395,000

  Last Listing Agent Parker Meyer Four Seasons Sotheby's Int.
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  /34

  $589,900

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

  66 Anthony St, Hillsdale, NY 12529

  This home on almost 4 acres with a private pond and scenic mountain and sunset views year-round, also abuts the Harlem Valley Rail Trail. It is withinwalking distance to the village of Hillsdale. Including the Roe Jan Brewing Co. IGA, the Hillsdale House, and the town park. Less then 5-min driveto Catamount; 25 min to Hudson NY, and 20 min to Great Barrington MA.

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  66 Anthony St, Hillsdale, NY 12529
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  /13

  $725,000 Sold Jan 20, 2026

  2318 County Road 11, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,569 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $462/SF
  • 24 Days On Market

  Last Listing Agent Emma French Gabel Real Estate

  2318 County Road 11, Hillsdale, NY 12529
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  /50

  Est $321,273 Not Listed For Sale

  9376 New York 22, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,684 Sq Ft
  • Built 1951

  9376 New York 22, Hillsdale, NY 12529

  Last Sold Summary

  • 11% Above List Price
  • $172/SF
  • 30 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Nicholas Miuccio Miuccio Real Estate Group
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  /23

  $495,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft

  217 Anthony St, Hillsdale, NY 12529

  A newly built home ideally located on the edge of the charming hamlet of Hillsdale, NY, this home offers the convenience of true walkability--just steps to everyday essentials including the local hardware store, grocery market, wine shop, post office, town hall, coffee shops, restaurants, and boutique shops. With 3-bedrooms and 2-bathrooms, the home spans approximately 1,350 square feet of modern

  John Barbato Compass, Hillsdale

  217 Anthony St, Hillsdale, NY 12529
• 

  $426,500 Sold Sep 11, 2025

  69 SW Colony Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft
  • Built 2021

  Last Sold Summary

  • 10% Below List Price
  • $421/SF
  • 358 Days On Market

  Current Estimated Value $438,166

  Last Listing Agent Michelle Ayala BHHS Hudson Valley Properties

  69 SW Colony Rd, Hillsdale, NY 12529
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  /13

  Est $386,000 Not Listed For Sale

  149 Yonderview Rd, Hillsdale, NY 12529

  149 Yonderview Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 40% Above List Price
  • 21 Days On Market

  Last Sold Price $275,500

  Last Listing Agent John O'Neill-Knasick eXp Realty
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  /18

  $2,999,000

  • Land
  • 242 Acres
  • $12,393 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

  $2,180,000 Sold Mar 02, 2026

  35 Harlemville Rd, Hillsdale, NY 12529

  • 5 Beds
  • 5.5 Baths
  • 7,200 Sq Ft
  • Built 1980

  Last Sold Summary

  • 34% Below List Price
  • $303/SF
  • 441 Days On Market

  Current Estimated Value $1,989,454

  Last Listing Agent Non MLS HVCR MLS HV Catskill Region MLS

  35 Harlemville Rd, Hillsdale, NY 12529
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  /29

  Not Listed For Sale

  10247 Ny-22 --, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,556 Sq Ft
  • Built 1970

  10247 Ny-22 --, Hillsdale, NY 12529

  Last Sold Summary

  • $353/SF
  • 247 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Paige Paluch WILLIAM RAVEIS - BERKSHIRE
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  /24

  $347,000

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft

  81 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! Property

  Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

  81 SW Colony Rd, Hillsdale, NY 12529
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  /9

  $215,000 Sold Nov 13, 2025

  10011 New York 22, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1975

  Last Sold Summary

  • 17% Below List Price
  • $207/SF

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

  10011 New York 22, Hillsdale, NY 12529
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  /34

  Est $2,769,009 Not Listed For Sale

  383 Mitchell St, Hillsdale, NY 12529

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft
  • Built 2023

  383 Mitchell St, Hillsdale, NY 12529

  Last Sold Summary

  • 2% Below List Price
  • $743/SF
  • 72 Days On Market

  Last Sold Price $2,825,000

  Last Listing Agent Nancy Felcetto Brown Harris Stevens Hudson
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  /44

  $1,250,000

  • 5 Beds
  • 3 Baths
  • 2,708 Sq Ft

  1 van Bueran Dr, Hillsdale, NY 12529

  Tucked away at Copake Lake! This fully renovated home is set on a private 5-acre lot and features an open floor plan with a spacious eat-in kitchen and large island, a dining area that seats 10, and a living room with a grand fireplace and custom built-in benches. French doors open to a large screened-in porch on a wrap-around deck, offering sweeping views of the surrounding landscape. A second,

  John Barbato Compass, Hillsdale

  1 van Bueran Dr, Hillsdale, NY 12529
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  /114

  $3,000,000 Sold Jun 10, 2025

  184A Cambridge Rd, Hillsdale, NY 12529

  • 5 Beds
  • 4.5 Baths
  • 4,130 Sq Ft
  • Built 2021

  Last Sold Summary

  • 12% Below List Price
  • $726/SF
  • 35 Days On Market

  Current Estimated Value $2,538,886

  Last Listing Agent Annabel Taylor Four Seasons Sotheby's International Realty

  184A Cambridge Rd, Hillsdale, NY 12529
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  /25

  Not Listed For Sale

  0 Railroad Ln Unit 149543, Hillsdale, NY 12529

  0 Railroad Ln Unit 149543, Hillsdale, NY 12529

  Last Sold Summary

  • 257 Days On Market

  Last Sold Price $252,000

  Last Listing Agent John Avenia Columbia County RE Specialist
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  /28

  $1,275,000

  • 1 Bed
  • 2 Baths
  • 1,700 Sq Ft

  401 Collins St Unit Stop 11, Hillsdale, NY 12529

  Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County's most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a

  Pamela King-Belfor Four Seasons Sotheby's Int.

  401 Collins St Unit Stop 11, Hillsdale, NY 12529
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  /29

  $1,220,000 Sold Jun 24, 2025

  90 Overlook Dr, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $581/SF
  • 10 Days On Market

  Current Estimated Value $1,265,758

  Last Listing Agent Jennifer Harvey Compass Greater NY LLC

  90 Overlook Dr, Hillsdale, NY 12529
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  /31

  Not Listed For Sale

  615 County Route 21, Ghent, NY 12075

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 2002

  615 County Route 21, Ghent, NY 12075

  Last Sold Summary

  • $259/SF
  • 59 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Beth DeMatteo Berkshire Hathaway HomeService
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  /7

  $259,000

  • 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 live/work.

  David Birch Barns & Farms Realty, LLC

  9249 Route 22 Rd, Hillsdale, NY 12516
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  /85

  $3,850,000 Sold Dec 05, 2025

  350 Tory Hill Farm Rd, Hillsdale, NY 12529

  • 4 Beds
  • 5 Baths
  • 5,998 Sq Ft
  • Built 2008

  Last Sold Summary

  • 4% Below List Price
  • $642/SF
  • 142 Days On Market

  Current Estimated Value $3,972,215

  Last Listing Agent John Barbato Compass, Hillsdale

  350 Tory Hill Farm Rd, Hillsdale, NY 12529
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  /17

  Not Listed For Sale

  39 Stop 26 Justice Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 1,896 Sq Ft
  • Built 1984

  39 Stop 26 Justice Rd, Hillsdale, NY 12529

  Last Sold Summary

  • $203/SF
  • 35 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Karen Davala Davala Real Estate
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  /19

  $225,000

  • 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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  $359,900 Sold Apr 21, 2025

  631 SW Colony Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,219 Sq Ft
  • Built 1955

  Last Sold Summary

  • $295/SF
  • 80 Days On Market

  Last Listing Agent Angel Ayala BHHS Hudson Valley Properties

  631 SW Colony Rd, Hillsdale, NY 12529
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  /37

  Not Listed For Sale

  9361 Ny-22 --, Hillsdale, NY 12529

  • 4 Beds
  • 2.5 Baths
  • 2,681 Sq Ft
  • Built 1830

  9361 Ny-22 --, Hillsdale, NY 12529

  Last Sold Summary

  • $263/SF
  • 45 Days On Market

  Last Sold Price $705,000

  Last Listing Agent Jessie Bennett William Pitt
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  /21

  $1,650,000

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

  75 Upper Hollow Rd, Hillsdale, NY 12529

  This rare 193-acre estate in Austerlitz/Hillsdale, very close to the Berkshire border, offers incredible possibilities as a private family compound. Live in the charming log cottage enjoying the existing pond, creek, and wooded hiking trails, while you build your dream home. Recently renovated, the cottage features an updated bathroom and an expanded living room, blending modern comfort with

  Janet Kain The Kinderhook Group, Inc.

  75 Upper Hollow Rd, Hillsdale, NY 12529
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  /26

  $715,000 Sold May 12, 2025

  35 Stagecoach Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1973

  Last Sold Summary

  • 23% Above List Price
  • $440/SF
  • 33 Days On Market

  Current Estimated Value $645,972

  Last Listing Agent Maggie Merelle William Pitt Sothebys Intn'l

  35 Stagecoach Rd, Hillsdale, NY 12529
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  /2

  Not Listed For Sale

  0 Justice Rd, Hillsdale, NY 12529

  0 Justice Rd, Hillsdale, NY 12529

  Last Sold Summary

  Last Sold Price $73,000

  Last Listing Agent Kelsey Winters Davala Real Estate, LLC
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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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  /27

  $1,290,000 Sold Nov 03, 2025

  120 Pumpkin Hollow Rd N, Hillsdale, NY 12529

  • 3 Beds
  • 3 Baths
  • 1,474 Sq Ft
  • Built 2025

  Last Sold Summary

  • $875/SF
  • 27 Days On Market

  Current Estimated Value $1,356,000

  Last Listing Agent Steven Gray Compass Greater NY, LLC

  120 Pumpkin Hollow Rd N, Hillsdale, NY 12529
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  /45

  Not Listed For Sale

  228 County Route 21 --, Hillsdale, NY 12529

  • 6 Beds
  • 3 Baths
  • 3,028 Sq Ft
  • Built 1942

  228 County Route 21 --, Hillsdale, NY 12529

  Last Sold Summary

  • $182/SF
  • 13 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Michael Castellano GILCREST PROPERTIES
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  /69

  $2,995,000

  • 4 Beds
  • 3 Baths
  • 3,641 Sq Ft

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

  Welcome to Wolverton Creative Compound, a 119-acre estate in Claverack, NY, offering total privacy, wide southern light, integrated live-work studios, and a large swimmable pond with pebble beach. The 1830s farmhouse features four bedrooms, two baths, original moldings and Dutch doors, a whole-house water filter, and a bright layout for indoor-outdoor living. A fully insulated studio barn is

  Anthony D'Argenzio Houlihan Lawrence

  88 Mac Brown Rd, Claverack-Red Mills, NY 12513
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  /41

  $534,000 Sold Oct 29, 2025

  58 Deer Track Ln, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1965

  Last Sold Summary

  • 1% Below List Price
  • $315/SF
  • 177 Days On Market

  Current Estimated Value $536,756

  Last Listing Agent Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  58 Deer Track Ln, Hillsdale, NY 12529
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  /20

  Est $457,680 Not Listed For Sale

  3133 County Route 7, Copake, NY 12516

  • 2 Beds
  • 1 Bath
  • 1,494 Sq Ft
  • Built 1951

  3133 County Route 7, Copake, NY 12516

  Last Sold Summary

  • 8% Above List Price
  • $284/SF
  • 73 Days On Market

  Last Sold Price $425,000

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.
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  /17

  $499,000

  • Land
  • 83.22 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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  /34

  $640,000 Sold Oct 15, 2025

  7 Memory Ln, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,010 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Below List Price
  • $634/SF
  • 27 Days On Market

  Current Estimated Value $679,734

  Last Listing Agent John Barbato Compass, Hillsdale

  7 Memory Ln, Hillsdale, NY 12529
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  /11

  Not Listed For Sale

  10118 State Route 22, Hillsdale, NY 12529

  10118 State Route 22, Hillsdale, NY 12529

  Last Sold Summary

  • 332 Days On Market

  Last Sold Price $12,800

  Last Listing Agent John Avenia Columbia County RE Specialist

Showing Results 81 - 120, Page 3 of 18