Hillsdale, NY Homes

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  /14

  $235,000 Under Contract

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft

  49 Stonehill Dr, Hillsdale, NY 12529

  This completely redone Hillsdale cottage is the perfect rustic but refined getaway! Only 525 square feet, with one studio style bedroom, it feels spacious with a vaulted beamed ceiling, new wideboard pine floors, a stunning new kitchen with all new appliances including a five burner gas stove with a stainless steel hood, Fisher Paykel dishwasher drawers, double sinks, butcher block counters and a

  Sarah Lipsky William Pitt Sothebys Intn'l

  49 Stonehill Dr, Hillsdale, NY 12529
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  /26

  $510,000 Sold Dec 15, 2025

  25 Catamount Rd, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 820 Sq Ft
  • Built 2024

  Last Sold Summary

  • 7% Below List Price
  • $622/SF
  • 33 Days On Market

  Last Listing Agent Paige Paluch Lance Vermeulen Real Estate

  25 Catamount Rd, Hillsdale, NY 12529
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  /28

  Est $356,130 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft

  119 Black Grocery Rd, Hillsdale, NY 12529

  119 Black Grocery Rd, Hillsdale, NY 12529
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  /15

  $2,999,000

  • Land
  • 242 Acres
  • $12,393 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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  /22

  $347,000 Sold Feb 11, 2025

  105 Seekonk Rd, Hillsdale, NY 12529

  • 1 Bed
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Below List Price
  • $306/SF
  • 56 Days On Market

  Last Listing Agent Paige Paluch LANCE VERMEULEN RE, INC

  105 Seekonk Rd, Hillsdale, NY 12529
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  /14

  Est $422,476 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,343 Sq Ft

  52 Connelly Rd, Hillsdale, NY 12529

  52 Connelly Rd, Hillsdale, NY 12529
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  /28

  $490,000

  • 4 Beds
  • 5 Baths
  • 3,425 Sq Ft

  364 Yonderview Rd, Hillsdale, NY 12529

  Reduced Price! Close to skiing and the Berkshires. Once the Flood farmhouse, circa 1850. Over 3400 sf sited on 5 acres. Beautiful perennial gardens. Farmland views of the Taconic Range. Attached 2-car garage. The main floor has an office, that connects the home to the garage. Formal living room and formal dining room. The primary suite includes both his and hers full bathrooms, and a changing

  Lindsay Lebrecht Copake Lake Realty Corp.

  364 Yonderview Rd, Hillsdale, NY 12529
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  /2

  $999,990 Sold Jan 10, 2025

  40 Dugway Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 965 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $1,036/SF
  • 97 Days On Market

  Last Listing Agent Paige Paluch LANCE VERMEULEN RE, INC

  40 Dugway Rd, Hillsdale, NY 12529
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  /27

  Est $858,797 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths

  66 Fado Rd, Hillsdale, NY 12529

  66 Fado Rd, Hillsdale, NY 12529
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  /31

  $1,695,000

  • Land
  • 127.1 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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  /68

  $3,700,000 Sold Aug 18, 2025

  149 Tory Hill Farm Rd, Hillsdale, NY 12529

  • 4 Beds
  • 2.5 Baths
  • 3,604 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Above List Price
  • $1,027/SF
  • 39 Days On Market

  Current Estimated Value $3,614,646

  Last Listing Agent John Barbato Compass, Hillsdale

  149 Tory Hill Farm Rd, Hillsdale, NY 12529
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  /2

  Est $361,181 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft

  189 Prach Rd, Hillsdale, NY 12529

  189 Prach Rd, Hillsdale, NY 12529
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  /26

  $1,100,000

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

  9715 New York 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 Sotheby's Int.

  9715 New York 22, Hillsdale, NY 12529
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  /39

  $912,500 Sold Nov 07, 2025

  11 Cold Water St, Hillsdale, NY 12529

  • 5 Beds
  • 3.5 Baths
  • 2,834 Sq Ft
  • Built 1848

  Last Sold Summary

  • 2% Above List Price
  • $322/SF
  • 29 Days On Market

  Last Listing Agent MATTHEW CAREY Rouse + Co Real Estate, LLC

  11 Cold Water St, Hillsdale, NY 12529
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  /20

  Est $284,928 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,841 Sq Ft

  10977 New York 22, Hillsdale, NY 12529

  10977 New York 22, Hillsdale, NY 12529
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  /14

  $725,000

  • 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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  /10

  Sold Mar 21, 2025

  199 Rt 217, Ghent, NY 12075

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1925

  Last Sold Summary

  • 99 Days On Market

  Last Listing Agent Kylah Campeta LYF Homes

  199 Rt 217, Ghent, NY 12075
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  /13

  Est $399,987 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,076 Sq Ft

  4 Texas Hill Rd, Hillsdale, NY 12529

  4 Texas Hill Rd, Hillsdale, NY 12529
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  /4

  $170,000 Under Contract

  • Land
  • 6.25 Acres
  • $27,200 per Acre

  0 Knapp Hollow Ln, Hillsdale, NY 12529

  6+ acres of gentle rolling land in a scenic Hillsdale location. Nestled along a quiet back country dead end road this privately located land offers the perfect blend of natural beauty and tranquility. Possible western views with gentle clearing. A stream partially borders the land adding to the charm.Conveniently located midway to Great Barrington and Hudson this surveyed property offers easy

  marylou Kersten Copake Lake Realty Corp.

  0 Knapp Hollow Ln, Hillsdale, NY 12529
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  $1,100,000 Sold Aug 18, 2025

  515 Turnpike, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Built 1983

  Last Sold Summary

  • 8% Below List Price
  • $515/SF
  • 50 Days On Market

  Last Listing Agent Joseph Briggs William Pitt Sothebys Int Rlty

  515 Turnpike, Hillsdale, NY 12529
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  /44

  Est $1,104,989 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  2367 County Road 11, Hillsdale, NY 12529

  2367 County Road 11, Hillsdale, NY 12529
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  /10

  $3,600,000

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

  90 W End Rd, Hillsdale, NY 12529

  For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is

  Parker Meyer Four Seasons Sotheby's Int.

  90 W End Rd, Hillsdale, NY 12529
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  $1,150,000 Sold Nov 17, 2025

  306 County Route 21c, Ghent, NY 12075

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • Built 1890

  Last Sold Summary

  • 8% Below List Price
  • $460/SF
  • 48 Days On Market

  Last Listing Agent Nancy Felcetto Brown Harris Stevens HV LLC

  306 County Route 21c, Ghent, NY 12075
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  /20

  Est $326,224 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft

  1337 County Route 21, Ghent, NY 12075

  1337 County Route 21, Ghent, NY 12075
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  /36

  $650,000

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

  2657 New York 23, Hillsdale, NY 12529

  Proudly offering one of Hillsdale's most iconic and enduring homes—an exquisite piece of the Hudson Valley's heritage, perfectly positioned at the crossroads between Hudson, NY and Great Barrington, MA. Set in the vibrant and historic hamlet center, this timeless 3-bedroom, 2-bathroom residence is simply beautiful colonial charm.Thoughtfully renovated from top to bottom, the home retains its

  John Barbato Compass, Hillsdale

  2657 New York 23, Hillsdale, NY 12529
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  /18

  $586,000 Sold Jun 30, 2025

  676 County Route 21, Ghent, NY 12075

  • 2 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1988

  Last Sold Summary

  • 3% Above List Price
  • $452/SF
  • 38 Days On Market

  Last Listing Agent Terry Cozzolino Cozzolino Real Estate Inc

  676 County Route 21, Ghent, NY 12075
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  /17

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  9398 New York 22, Hillsdale, NY 12529

  9398 New York 22, Hillsdale, NY 12529
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  /30

  $810,000

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

  60 Anthony St, Hillsdale, NY 12529

  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 min ride to

  Gerard Meenagh The Meenagh Group Realty

  60 Anthony St, Hillsdale, NY 12529
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  /32

  $1,175,000 Sold Jul 03, 2025

  17 White Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,194 Sq Ft
  • Built 1970

  Last Sold Summary

  • 9% Below List Price
  • $536/SF
  • 38 Days On Market

  Current Estimated Value $1,194,598

  Last Listing Agent PATRICIA HINKEIN Patricia A. Hinkein Realty

  17 White Hill Rd, Hillsdale, NY 12529
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  /6

  Not Listed For Sale

  0 Pumpkin Hollow Rd S, Hillsdale, NY 12529

  0 Pumpkin Hollow Rd S, Hillsdale, NY 12529
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  /13

  $325,000

  • Land
  • 49.91 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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  /34

  $805,000 Sold Nov 14, 2025

  470 N Mountain Rd, Copake Falls, NY 12517

  • 3 Beds
  • 3 Baths
  • 1,636 Sq Ft
  • Built 1840

  Last Sold Summary

  • 1% Above List Price
  • $492/SF
  • 8 Days On Market

  Last Listing Agent Tom Lynch Compass Greater NY LLC

  470 N Mountain Rd, Copake Falls, NY 12517
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  /50

  Est $326,868 Not Listed For Sale

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

  9376 New York 22, Hillsdale, NY 12529

  9376 New York 22, Hillsdale, NY 12529
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  /25

  $1,525,000

  • 4 Beds
  • 4.5 Baths
  • 3,666 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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  /33

  $310,000 Sold May 01, 2025

  287 New York 71, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Above List Price
  • $221/SF
  • 26 Days On Market

  Last Listing Agent Peter Newman Beach & Bartolo Realtors

  287 New York 71, Hillsdale, NY 12529
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  /13

  Est $225,000 Not Listed For Sale

  149 Yonderview Rd, Hillsdale, NY 12529

  149 Yonderview Rd, Hillsdale, NY 12529
• 

  

  /29

  $785,000 Pending

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

  9254 New York 22, Hillsdale, NY 12529

  Hillsdale 2500 SF 4BR residence with large deck, inground pool and 60x100 garage on 2.9 acs. Currently Auto Repair Business near Junction of Routes 22 & 23. Incredible opportunity to continue Auto Repair and towing business or convert 60x100 Garage into Storage Facility or other use. House would make great rental property.

  David Birch Barns & Farms Realty

  9254 New York 22, Hillsdale, NY 12529
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  /37

  $570,000 Sold Jan 09, 2025

  68 Cherokee Dr, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft
  • Built 1994

  Last Sold Summary

  • 1% Below List Price
  • $338/SF
  • 61 Days On Market

  Current Estimated Value $609,502

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist

  68 Cherokee Dr, Hillsdale, NY 12529
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  /29

  Not Listed For Sale

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

  10247 Ny-22 --, Hillsdale, NY 12529

  10247 Ny-22 --, Hillsdale, NY 12529
• 

  

  /25

  $799,800 New Construction

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

  801 Rodman Rd, Hillsdale, NY 12529

  New listing in Hillsdale, set high on a quiet dirt road where privacy, peace, and panoramic views define your backdrop. Why wait a year and a half for a new build when you could be in by Christmas? This brand-new construction is underway and ready for you to make it your own. The structure is in place with a brand-new drilled well, septic system, and 200-amp electrical service already set.

  Michael Castellano Gilcrest Properties

  801 Rodman Rd, Hillsdale, NY 12529

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