2,791

Hillsdale, NY Homes

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  • /16

    $999,000

    • Land
    • 300.8 Acres
    • $3,321 per Acre

    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 Past Member

    25 Nobletown Rd, 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 $455,333

    Last Listing Agent Kate Lascar COMPASS MASSACHUSETTS , LLC GB

    51 Taconic Creek Rd, Hillsdale, NY 12529
    • 60 River Rd, Austerlitz, NY 12017

      Est $1,502,097 Not Listed For Sale

      60 River Rd, Austerlitz, NY 12017

      • 4 Beds
      • 4 Baths
      • 2,626 Sq Ft
      • Built 1890
      60 River Rd, Austerlitz, NY 12017

      Last Sold Summary

      • 16% Above List Price
      • $495/SF
      • 9 Days On Market

      Last Sold Price $1,300,000

      Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

  • /19

    $325,000

    • 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! Property

    Margaret Bower Avenia Columbia County RE Specialist

    81 SW Sw Colony Rd, Hillsdale, NY 12529
  • /2

    $1,250,000 Sold Mar 09, 2026

    0 La Branche Rd Unit 248871, Hillsdale, NY 12529

    • Land
    • 203 Acres
    • $6,158 per Acre

    Last Sold Summary

    • 8 Days On Market

    Last Listing Agent Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    0 La Branche Rd Unit 248871, Hillsdale, NY 12529
    • /3

      Not Listed For Sale

      10695 Ny-22, Hillsdale, NY 12529

      10695 Ny-22, Hillsdale, NY 12529

      Last Sold Summary

      • 39 Days On Market

      Last Sold Price $137,000

      Last Listing Agent Scott Varley KW Platform

  • /8

    $375,000

    • Land
    • 90 Acres
    • $4,167 per Acre

    0 Harlemville Rd Unit 20254229, Hillsdale, NY 12529

    On a bucolic country by-way you will find this very private wooded hilltop parcel with Catskill Mountain views. Gorgeous mature timber and beautiful rocky outcrops dot this parcel. Access is via a brief right-of-way and along a pretty private lane. Note reduced taxes due to a power line easement to the rear of the property. Suitable for a single main residence.

    James Male HOUSE Hudson Valley Realty

    0 Harlemville Rd Unit 20254229, Hillsdale, NY 12529
  • 228 County Road 21, Hillsdale, NY 12529

    $1,100,000 Sold Sep 05, 2025

    228 County Road 21, Hillsdale, NY 12529

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 1942

    Last Sold Summary

    • 7% Below List Price
    • $517/SF
    • 78 Days On Market

    Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

    228 County Road 21, Hillsdale, NY 12529
    • /32

      Not Listed For Sale

      2653 New York 23, Hillsdale, NY 12529

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1970
      2653 New York 23, Hillsdale, NY 12529

      Last Sold Summary

      • $450/SF
      • 27 Days On Market

      Last Sold Price $675,000

      Last Listing Agent John Barbato Compass, Hillsdale

  • /26

    $1,100,000 Pending

    • 5 Beds
    • 2.5 Baths
    • 3,350 Sq Ft

    9715 State Route 22, Hillsdale, NY 12529

    Said to be Hillsdale's second oldest home, this historic c1788 Shaker built center chimney Colonial sits on 17 acres of sprawling green hillside, gardens, and fruit trees. Once the home of Captain John Collin III, the home sits along the beautiful corridor connecting the Hudson Valley and the Berkshires— an area characterized by its rolling hillsides and rural landscape. Meticulously restored,

    Annabel Taylor Four Seasons Sothebys Intl

    9715 State Route 22, Hillsdale, NY 12529
  • /2

    $94,000 Sold Sep 16, 2025

    76 New York 71, Hillsdale, NY 12529

    • Land
    • 6 Acres
    • $15,667 per Acre

    Last Sold Summary

    • 24% Below List Price
    • 472 Days On Market

    Last Listing Agent Rochelle Bartolo Beach & Bartolo Realtors

    76 New York 71, Hillsdale, NY 12529
    • /33

      Est $3,765,649 Not Listed For Sale

      256 Island Dr, Copake, NY 12521

      • 5 Beds
      • 2 Baths
      • 5,300 Sq Ft
      • Built 2014
      256 Island Dr, Copake, NY 12521

      Last Sold Summary

      • 1% Below List Price
      • $718/SF
      • 36 Days On Market

      Last Sold Price $3,807,437

      Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

  • /35

    $395,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,660 Sq Ft

    50 Lockwood Rd, Craryville, NY 12521

    Anthony D'Argenzio Houlihan Lawrence, Inc

    50 Lockwood Rd, Craryville, NY 12521
  • /38

    $635,000 Sold Oct 24, 2025

    47 Cherokee Dr, Hillsdale, NY 12529

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Below List Price
    • $509/SF
    • 98 Days On Market

    Current Estimated Value $627,153

    Last Listing Agent Arlena Armstrong Anatole House LLC

    47 Cherokee Dr, Hillsdale, NY 12529
    • /20

      Not Listed For Sale

      0 W End Rd, Hillsdale, NY 12529

      0 W End Rd, Hillsdale, NY 12529

      Last Sold Summary

      • 24 Days On Market

      Last Sold Price $110,000

      Last Listing Agent Michael Tellerday Houlihan Lawrence, Inc.

  • /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
  • /41

    $2,000,000 Sold Nov 18, 2025

    250 Island Dr, Craryville, NY 12521

    • 3 Beds
    • 3 Baths
    • 2,720 Sq Ft
    • Built 2000

    Last Sold Summary

    • 20% Below List Price
    • $735/SF
    • 495 Days On Market

    Current Estimated Value $2,146,302

    Last Listing Agent John Barbato Compass, Hillsdale

    250 Island Dr, Craryville, NY 12521
    • /26

      Not Listed For Sale

      2871 New York 23, Hillsdale, NY 12529

      • 29 Beds
      • 28 Baths
      • 3,000 Sq Ft
      • Built 1920
      2871 New York 23, Hillsdale, NY 12529

      Last Sold Summary

      • $367/SF

      Last Sold Price $1,100,000

      Last Listing Agent Natalia de Amorim Preferred Country Properties

  • /20

    $598,000

    • Land
    • 12.6 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
    • /17

      Est $371,864 Not Listed For Sale

      2951 State Route 23, Hillsdale, NY 12529

      • 2 Beds
      • 1.5 Baths
      • 1,111 Sq Ft
      • Built 1930
      2951 State Route 23, Hillsdale, NY 12529

      Last Sold Summary

      • 5% Above List Price
      • $320/SF
      • 62 Days On Market

      Last Sold Price $355,000

      Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

  • /44

    $6,950,000

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

    890 Bald Mountain Rd, Austerlitz, NY 12017

    Welcome to Bald Mountain Estate, an extraordinary private compound spanning 85 breathtaking acres overlooking the Hudson Valley and the Berkshire Hills. This four-building, ultra-contemporary estate epitomizes modern country luxury, featuring floor-to-ceiling glass walls and a steel infrastructure that creates a distinctive blend of rusticelegance and architectural sophistication.The

    Lisa Bouchard Hoe The Kinderhook Group, Inc.

    890 Bald Mountain Rd, Austerlitz, NY 12017
    • /2

      Not Listed For Sale

      361 Craryville Rd, Hillsdale, NY 12529

      • 3 Beds
      • 2 Baths
      • 2,024 Sq Ft
      • Built 1900
      361 Craryville Rd, Hillsdale, NY 12529

      Last Sold Summary

      • $487/SF
      • 375 Days On Market

      Last Sold Price $985,000

      Last Listing Agent Andrew Gates Past Member

    • /26

      Est $305,283 Not Listed For Sale

      431 SW Colony Rd, Hillsdale, NY 12529

      • 3 Beds
      • 1 Bath
      • 1,200 Sq Ft
      • Built 1952
      431 SW Colony Rd, Hillsdale, NY 12529

      Last Sold Summary

      • 6% Above List Price
      • $239/SF
      • 79 Days On Market

      Last Sold Price $287,000

      Last Listing Agent John Barbato Compass, Hillsdale

    • /25

      Est $902,622 Not Listed For Sale

      184 Overlook Dr, Hillsdale, NY 12529

      • 4 Beds
      • 2 Baths
      • 2,126 Sq Ft
      • Built 1910
      184 Overlook Dr, Hillsdale, NY 12529

      Last Sold Summary

      • 5% Above List Price
      • $406/SF
      • 73 Days On Market

      Last Sold Price $863,000

      Last Listing Agent Jason Loeb Four Seasons Sotheby's Int.

    • /36

      Not Listed For Sale

      208 Cambridge Rd, Hillsdale, NY 12529

      • 3 Beds
      • 3.5 Baths
      • 2,384 Sq Ft
      • Built 1981
      208 Cambridge Rd, Hillsdale, NY 12529

      Last Sold Summary

      • $389/SF
      • 56 Days On Market

      Last Sold Price $927,000

      Last Listing Agent Gerard Meenagh The Meenagh Group Realty

    • /23

      Est $779,147 Not Listed For Sale

      161 White Hill Rd, Hillsdale, NY 12529

      • 2 Beds
      • 1 Bath
      • 1,310 Sq Ft
      • Built 1996
      161 White Hill Rd, Hillsdale, NY 12529

      Last Sold Summary

      • 108% Above List Price
      • $286/SF
      • 69 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Victor Franco Jr Weichert Realtors Northeast Gp

    • /3

      Not Listed For Sale

      0 Connelly - Off Unit 137624, Copake, NY 12517

      0 Connelly - Off Unit 137624, Copake, NY 12517

      Last Sold Summary

      • 151 Days On Market

      Last Sold Price $90,000

      Last Listing Agent Jennifer Capala William Pitt Sothebys Intn'l

    • /4

      Not Listed For Sale

      0 Mitchell St Unit 131897, Hillsdale, NY 12529

      0 Mitchell St Unit 131897, Hillsdale, NY 12529

      Last Sold Summary

      • 312 Days On Market

      Last Sold Price $1,200,000

      Last Listing Agent Jennifer Harvey Compass Greater NY LLC

    • /8

      Not Listed For Sale

      0 Mitchell St Unit 131892, Hillsdale, NY 12529

      0 Mitchell St Unit 131892, Hillsdale, NY 12529

      Last Sold Summary

      • 237 Days On Market

      Last Sold Price $999,000

      Last Listing Agent Jennifer Harvey Compass Greater NY LLC

    • /4

      Not Listed For Sale

      0 Mitchell St Unit 132496, Hillsdale, NY 12529

      0 Mitchell St Unit 132496, Hillsdale, NY 12529

      Last Sold Summary

      • 755 Days On Market

      Last Sold Price $220,000

      Last Listing Agent Tracy Tassinari Past Member

    • /9

      Not Listed For Sale

      Unlisted Address

      • 4 Beds
      • Built 1970
      Unlisted Address

      Last Sold Summary

      • $222/SF
      • 148 Days On Market

      Last Sold Price $1,200,000

      Last Listing Agent Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    • /2

      Est $855,595 Not Listed For Sale

      14 Holm Rd, Hillsdale, NY 12529

      • 3 Beds
      • 3 Baths
      • 2,500 Sq Ft
      • Built 2009
      14 Holm Rd, Hillsdale, NY 12529

      Last Sold Summary

      • 50% Below List Price
      • $228/SF

      Last Sold Price $570,000

      Last Listing Agent marylou Kersten COPAKE LAKE REALTY CORP.

    • /2

      Est $297,811 Not Listed For Sale

      100 Lockwood Rd, Craryville, NY 12521

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1950
      100 Lockwood Rd, Craryville, NY 12521

      Last Sold Summary

      • 53% Above List Price
      • $195/SF
      • 88 Days On Market

      Last Sold Price $195,000

      Last Listing Agent PATRICIA HINKEIN Patricia A. Hinkein Realty

    • /30

      Est $866,011 Not Listed For Sale

      212 Pumpkin Hollow Rd N, Hillsdale, NY 12529

      • 3 Beds
      • 2 Baths
      • 1,500 Sq Ft
      • Built 1840
      212 Pumpkin Hollow Rd N, Hillsdale, NY 12529

      Last Sold Summary

      • 15% Above List Price
      • $500/SF
      • 88 Days On Market

      Last Sold Price $749,990

      Last Listing Agent Andrea Stagg RE/MAX

    • /28

      Est $458,171 Not Listed For Sale

      14 Mansfield Rd, Hillsdale, NY 12529

      • 2 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1880
      14 Mansfield Rd, Hillsdale, NY 12529

      Last Sold Summary

      • 35% Above List Price
      • $260/SF
      • 89 Days On Market

      Last Sold Price $338,500

      Last Listing Agent Jennifer Capala William Pitt Sothebys Intn'l

    • /54

      Est $620,799 Not Listed For Sale

      1650 County Route 11, Craryville, NY 12521

      • 3 Beds
      • 2 Baths
      • 1,782 Sq Ft
      • Built 2003
      1650 County Route 11, Craryville, NY 12521

      Last Sold Summary

      • 36% Above List Price
      • $255/SF
      • 196 Days On Market

      Last Sold Price $455,000

      Last Listing Agent Steve King Venture Fox Realty Group LLC

    • /37

      Est $893,791 Not Listed For Sale

      111 Hunt Rd, Hillsdale, NY 12529

      • 3 Beds
      • 2 Baths
      • 2,234 Sq Ft
      • Built 1970
      111 Hunt Rd, Hillsdale, NY 12529

      Last Sold Summary

      • 23% Above List Price
      • $325/SF
      • 14 Days On Market

      Last Sold Price $726,000

      Last Listing Agent Jennifer Capala William Pitt Sothebys Intn'l

    • /10

      Est $700,916 Not Listed For Sale

      1000 Mitchell St, Hillsdale, NY 12529

      • 5 Beds
      • 2 Baths
      • 1,928 Sq Ft
      • Built 2008
      1000 Mitchell St, Hillsdale, NY 12529

      Last Sold Summary

      • 180% Above List Price
      • $130/SF
      • 126 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist

    • /10

      Est $777,245 Not Listed For Sale

      86 Stagecoach Rd, Hillsdale, NY 12529

      • 3 Beds
      • Built 2023
      86 Stagecoach Rd, Hillsdale, NY 12529

      Last Sold Summary

      • 1,010% Above List Price
      • $80/SF
      • 93 Days On Market

      Last Sold Price $70,000

      Last Listing Agent Marc Kusewich Past Member

    • /15

      Est $343,148 Not Listed For Sale

      234 Harder Rd, Hillsdale, NY 12529

      • 3 Beds
      • 1.5 Baths
      • 1,500 Sq Ft
      • Built 1890
      234 Harder Rd, Hillsdale, NY 12529

      Last Sold Summary

      • 77% Below List Price
      • $1,000/SF
      • 900 Days On Market

      Last Sold Price $1,500,000

      Last Listing Agent Karen Davala Davala Real Estate

Showing Results 121 - 160, Page 4 of 18

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