Hillsdale, NY Homes

• 

  

  

  /42

  $1,500,000 Sold Aug 01, 2025

  57 Cold Water St, Hillsdale, NY 12529

  • 2 Beds
  • 3 Baths
  • 7,656 Sq Ft
  • Built 1928

  Last Sold Summary

  • 5% Below List Price
  • $196/SF
  • 59 Days On Market

  Current Estimated Value $1,503,752

  Last Listing Agent Annabel Taylor Four Seasons Sotheby's Int.

  57 Cold Water St, Hillsdale, NY 12529
• 

  

  

  /34

  Est $2,853,726 Not Listed For Sale

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

  383 Mitchell St, Hillsdale, NY 12529

  383 Mitchell St, Hillsdale, NY 12529
• 

  

  

  /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
• 

  

  

  /28

  $400,000 Sold Sep 02, 2025

  840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1900

  Last Sold Summary

  • 11% Above List Price
  • $231/SF
  • 27 Days On Market

  Current Estimated Value $402,377

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

  840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529
• 

  

  

  /25

  Not Listed For Sale

  0 Railroad Ln Unit 149543, Hillsdale, NY 12529

  0 Railroad Ln Unit 149543, Hillsdale, NY 12529
• 

  

  /25

  $1,250,000

  • 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 for

  Owen Davidson Brown Harris Stevens HV LLC

  161 Stagecoach Rd, Hillsdale, NY 12529
• 

  

  /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

  Last Listing Agent Jennifer Harvey Compass Greater NY LLC

  441 Overlook Dr, Hillsdale, NY 12529
• 

  

  /31

  Not Listed For Sale

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

  615 County Route 21, Ghent, NY 12075

  615 County Route 21, Ghent, NY 12075
• 

  

  /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
• 

  $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 $434,677

  Last Listing Agent Michelle Ayala BHHS Hudson Valley Properties

  69 SW Colony Rd, Hillsdale, NY 12529
• 

  

  /17

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,896 Sq Ft

  39 Stop 26 Justice Rd, Hillsdale, NY 12529

  39 Stop 26 Justice Rd, Hillsdale, NY 12529
• 

  

  /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
• 

  

  /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
• 

  

  /37

  Not Listed For Sale

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

  9361 Ny-22 --, Hillsdale, NY 12529

  9361 Ny-22 --, Hillsdale, NY 12529
• 

  

  /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

  David Birch Barns & Farms Realty, LLC

  9249 Route 22 Rd, Hillsdale, NY 12516
• 

  

  /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 $2,468,221

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

  184A Cambridge Rd, Hillsdale, NY 12529
• 

  /2

  Not Listed For Sale

  0 Justice Rd, Hillsdale, NY 12529

  0 Justice Rd, Hillsdale, NY 12529
• 

  

  /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
• 

  

  /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 $1,239,981

  Last Listing Agent Jennifer Harvey Compass Greater NY LLC

  90 Overlook Dr, Hillsdale, NY 12529
• 

  

  /45

  Not Listed For Sale

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

  228 County Route 21 --, Hillsdale, NY 12529

  228 County Route 21 --, Hillsdale, NY 12529
• 

  

  /13

  $749,000 Pending

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

  2318 County Road 11, Hillsdale, NY 12529

  Warm and inviting custom new construction. 5 private acres, high end kitchen and baths, open layout. Soaring two story ceilings with oversized windows to take in the abundant light. Expansive covered porch provides the perfect outdoor living space. Step in to your own slice of peace and tranquility.Central location - 10 minutes to Hudson, 5 minutes to Taconic Pkwy.

  Emma French Gabel Real Estate

  2318 County Road 11, Hillsdale, NY 12529
• 

  

  /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

  Last Listing Agent John Barbato Compass, Hillsdale

  350 Tory Hill Farm Rd, Hillsdale, NY 12529
• 

  

  /20

  Est $526,481 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,494 Sq Ft

  3133 County Route 7, Copake, NY 12516

  3133 County Route 7, Copake, NY 12516
• 

  

  /40

  $2,695,000

  • 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
• 

  $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
• 

  

  /11

  Not Listed For Sale

  10118 State Route 22, Hillsdale, NY 12529

  10118 State Route 22, Hillsdale, NY 12529
• 

  

  /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
• 

  

  /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 $637,381

  Last Listing Agent Maggie Merelle William Pitt Sothebys Intn'l

  35 Stagecoach Rd, Hillsdale, NY 12529
• 

  Est $1,437,889 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,626 Sq Ft

  60 River Rd, Austerlitz, NY 12017

  60 River Rd, Austerlitz, NY 12017
• 

  

  /46

  $2,250,000

  • 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
• 

  

  /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

  Last Listing Agent Steven Gray Compass Greater NY, LLC

  120 Pumpkin Hollow Rd N, Hillsdale, NY 12529
• 

  

  /3

  Not Listed For Sale

  10695 Ny-22, Hillsdale, NY 12529

  10695 Ny-22, Hillsdale, NY 12529
• 

  

  /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
• 

  

  /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

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

  58 Deer Track Ln, Hillsdale, NY 12529
• 

  

  /32

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  2653 New York 23, Hillsdale, NY 12529

  2653 New York 23, Hillsdale, NY 12529
• 

  

  /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
• 

  

  /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

  Last Listing Agent John Barbato Compass, Hillsdale

  7 Memory Ln, Hillsdale, NY 12529
• 

  

  /33

  Est $4,191,205 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 5,300 Sq Ft

  256 Island Dr, Copake, NY 12521

  256 Island Dr, Copake, NY 12521
• 

  

  /38

  $1,295,000

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  2955 New York 23, Hillsdale, NY 12529

  Historic Upstate NY Sanctuary - 8.7 Magical Acres in Hillsdale, NY - known for its scenic beauty and small-town charmEscape to your own private paradise on this enchanting 8.7-acre property featuring a charming 1820's cottage, pristine swimming pond with waterfall, and endless outdoor adventures. This secluded sanctuary offers the perfect blend of historic character and natural beauty, just

  Chris Getman Houlihan Lawrence Inc.

  2955 New York 23, Hillsdale, NY 12529
• 

  

  /35

  $410,000 Sold Aug 15, 2025

  51 Taconic Creek Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1993

  Last Sold Summary

  • 12% Below List Price
  • $214/SF
  • 24 Days On Market

  Current Estimated Value $427,333

  Last Listing Agent Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  51 Taconic Creek Rd, Hillsdale, NY 12529

Showing Results 81 - 120, Page 3 of 18