Hillsdale, NY Homes

• 

  

  

  /18

  $335,000 Sold Jul 24, 2025

  118 Yonderview Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,536 Sq Ft
  • Built 1963

  Last Sold Summary

  • 4% Below List Price
  • $218/SF
  • 58 Days On Market

  Current Estimated Value $355,140

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

  118 Yonderview Rd, Hillsdale, NY 12529
• Selling your home? Sell it faster and for more with a Homes.com Boost.

  Learn More
• 

  

  

  /25

  Est $554,943 Not Listed For Sale

  15 Henich Ln, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1990

  15 Henich Ln, Hillsdale, NY 12529

  Last Sold Summary

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

  Last Sold Price $528,000

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
• 

  

  

  /6

  $199,000

  • Land
  • 33.31 Acres
  • $5,974 per Acre

  50 Dugway Rd, Hillsdale, NY 12529

  Create Your Own Vision.Escape to 33.31 acres of untouched beauty in Columbia County, NY, and close to 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. Over 1,677 feet of road frontage, and an old roadway that

  Jeffrey McKinney Beach & Bartolo Realtors

  50 Dugway Rd, Hillsdale, NY 12529
• 

  

  

  /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
• 

  

  

  /37

  Est $603,680 Not Listed For Sale

  68 Cherokee Dr, Hillsdale, NY 12529

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

  68 Cherokee Dr, Hillsdale, NY 12529

  Last Sold Summary

  • 6% Above List Price
  • $338/SF
  • 61 Days On Market

  Last Sold Price $570,000

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
• 

  

  /32

  $339,000

  • 3 Beds
  • 1 Bath
  • 1,470 Sq Ft

  9539 New York 22, Hillsdale, NY 12529

  Newly Renovated Hillsdale Gem! Welcome to this beautifully renovated 3-bedroom home in the heart of Hillsdale. Thoughtfully updated with today's buyer in mind, this residence blends modern comfort with timeless charm. Inside, you'll find a bright, welcoming kitchen featuring quartz countertops, high-end vinyl plank flooring, and a suite of updated appliances designed for both style and

  Marie Rodriguez Red Apple Realty

  9539 New York 22, Hillsdale, NY 12529
• 

  

  /14

  $255,000 Sold Feb 13, 2026

  49 Stonehill Dr, Hillsdale, NY 12529

  • 1 Bed
  • 1 Bath
  • 525 Sq Ft
  • Built 1963

  Last Sold Summary

  • 9% Above List Price
  • $486/SF
  • 78 Days On Market

  Current Estimated Value $231,717

  Last Listing Agent Sarah Lipsky William Pitt Sothebys Intn'l

  49 Stonehill Dr, Hillsdale, NY 12529
• 

  Est $1,458,998 Not Listed For Sale

  656 Breezy Hill Rd, Hillsdale, NY 12529

  • 4 Beds
  • 3.5 Baths
  • 2,272 Sq Ft
  • Built 1850

  656 Breezy Hill Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 2% Above List Price
  • $632/SF
  • 57 Days On Market

  Last Sold Price $1,435,000

  Last Listing Agent John Panzer Elyse Harney Real Estate
• 

  

  /24

  $615,000

  • 3 Beds
  • 1.5 Baths
  • 864 Sq Ft

  5 Adams Dr, Hillsdale, NY 12529

  This charming 3 BR, 1.5 Bath cottage is located across the street from Copake Lake and the HOA Waterfront, Marina and Beach area. Unlike some of the other homes in the area, the house is situated on an elevated, oversized lot with a big front yard and spectacular sunset views. Inside, the house features real wood paneling and a wood burning stove in the living room, a cozy kitchen with a new gas

  Russ Stein Compass Greater NY LLC

  5 Adams Dr, Hillsdale, NY 12529
• 

  

  /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 $3,304,102

  Last Listing Agent John Barbato Compass, Hillsdale

  149 Tory Hill Farm Rd, Hillsdale, NY 12529
• 

  

  /28

  Est $378,394 Not Listed For Sale

  119 Black Grocery Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • Built 1971

  119 Black Grocery Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 7% Above List Price
  • $286/SF
  • 211 Days On Market

  Last Sold Price $352,000

  Last Listing Agent Wendy Kenney Davala Real Estate, LLC
• 

  

  /46

  $3,350,000

  • 4 Beds
  • 4 Baths
  • 4,000 Sq Ft

  411 Texas Hill Rd, Hillsdale, NY 12529

  411 Texas Hill Road is an exemplary portrait of a Mid-Century home, set on 40 private acres. The home is positioned on one of the highest points in Columbia County, with views of both the Taconic and the Helderberg ranges. Located just 20 minutes from Hudson and surrounded by all the wonderful amenities of the Hudson Valley. Set on a quiet one-lane, town-maintained road, this private sanctuary is

  Marina Tatistcheff Compass Greater NY LLC

  411 Texas Hill Rd, Hillsdale, NY 12529
• 

  

  /4

  $150,000 Sold Jan 29, 2026

  0 Knapp Hollow Ln, Hillsdale, NY 12529

  • Land
  • 6.25 Acres
  • $24,000 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 39 Days On Market

  Last Listing Agent marylou Kersten Copake Lake Realty Corp.

  0 Knapp Hollow Ln, Hillsdale, NY 12529
• 

  

  /14

  Est $494,604 Not Listed For Sale

  52 Connelly Rd, Hillsdale, NY 12529

  • 4 Beds
  • 2 Baths
  • 2,343 Sq Ft
  • Built 1952

  52 Connelly Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 77% Above List Price
  • $120/SF
  • 142 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Amjad Mughal M J J Realty
• 

  

  /13

  $595,000

  • Land
  • 30 Acres
  • $19,833 per Acre

  0 Labranch Unit 20252234, 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.

  Tracy Tassinari Gabel Real Estate

  0 Labranch Unit 20252234, Hillsdale, NY 12529
• 

  

  /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
• 

  

  /27

  Est $899,682 Not Listed For Sale

  66 Fado Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • Built 1850

  66 Fado Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 28% Above List Price
  • $496/SF
  • 368 Days On Market

  Last Sold Price $705,000

  Last Listing Agent John Avenia Columbia County RE Specialist
• 

  

  /21

  $364,900

  • 3 Beds
  • 1 Bath
  • 1,381 Sq Ft

  9659 New York 22, Hillsdale, NY 12529

  Come see the new me!. I've had a face lift and you are sure to enjoy the gleaming hardwood floors and the updated kitchen with granite counters and new appliances. It's one level of easy living, and offers many wonderful features. Enjoy the spacious living room framed by a fireplace, or the cozy den which has one as well..The middle bedroom features sliders that open onto a deck, great to enjoy

  Tammy Molinski Coldwell Banker Advisor Realty

  9659 New York 22, Hillsdale, NY 12529
• 

  $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
• 

  /2

  Est $377,265 Not Listed For Sale

  189 Prach Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • Built 1964

  189 Prach Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 51% Above List Price
  • $283/SF
  • 24 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Daniel Mahar Coldwell Banker Advisor Realty
• 

  

  /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
• 

  $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

  Current Estimated Value $1,186,418

  Last Listing Agent Nancy Felcetto Brown Harris Stevens HV LLC

  306 County Route 21c, Ghent, NY 12075
• 

  

  /20

  Est $309,856 Not Listed For Sale

  10977 New York 22, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,841 Sq Ft
  • Built 1950

  10977 New York 22, Hillsdale, NY 12529

  Last Sold Summary

  • 47% Above List Price
  • $115/SF
  • 34 Days On Market

  Last Sold Price $211,000

  Last Listing Agent Scott Varley KW Platform
• 

  

  /28

  $490,000 Pending

  • 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
• 

  

  /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
• 

  

  /13

  Est $378,811 Not Listed For Sale

  4 Texas Hill Rd, Hillsdale, NY 12529

  • 4 Beds
  • 2 Baths
  • 1,076 Sq Ft
  • Built 1952

  4 Texas Hill Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 15% Above List Price
  • $307/SF
  • 38 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
• 

  

  /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
• 

  

  /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 $1,224,073

  Last Listing Agent PATRICIA HINKEIN Patricia A. Hinkein Realty

  17 White Hill Rd, Hillsdale, NY 12529
• 

  

  /44

  Est $1,219,373 Not Listed For Sale

  2367 County Road 11, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,600 Sq Ft
  • Built 1887

  2367 County Road 11, Hillsdale, NY 12529

  Last Sold Summary

  • 17% Below List Price
  • $567/SF
  • 27 Days On Market

  Last Sold Price $1,475,000

  Last Listing Agent Raj Kumar Four Seasons Sotheby's Int.
• 

  

  /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
• 

  $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

  Current Estimated Value $797,409

  Last Listing Agent Tom Lynch Compass Greater NY LLC

  470 N Mountain Rd, Copake Falls, NY 12517
• 

  

  /20

  Est $351,658 Not Listed For Sale

  1337 County Route 21, Ghent, NY 12075

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 1910

  1337 County Route 21, Ghent, NY 12075

  Last Sold Summary

  • 43% Above List Price
  • $134/SF
  • 35 Days On Market

  Last Sold Price $246,000

  Last Listing Agent April Seney Core Real Estate Team
• 

  

  /36

  $595,000 Under Contract

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

  2657 State Route 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 State Route 23, Hillsdale, NY 12529
• 

  

  /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
• 

  

  /17

  Not Listed For Sale

  9398 New York 22, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1951

  9398 New York 22, Hillsdale, NY 12529

  Last Sold Summary

  • $157/SF
  • 32 Days On Market

  Last Sold Price $143,100

  Last Listing Agent Barbara Robinson Red Apple Realty
• 

  

  /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
• 

  

  /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 $1,466,222

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

  57 Cold Water St, Hillsdale, NY 12529
• 

  

  /6

  Not Listed For Sale

  0 Pumpkin Hollow Rd S, Hillsdale, NY 12529

  0 Pumpkin Hollow Rd S, Hillsdale, NY 12529

  Last Sold Summary

  • 190 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Austin Urban Venture Fox Realty Group
• 

  

  /29

  $425,000 Under Contract

  • 2 Beds
  • 1.5 Baths
  • 1,630 Sq Ft

  44 Collins St, Hillsdale, NY 12529

  Classic country homes like this one don't come on the market often and don't last long when they do.This 1933 Cape Cod home is new to the market after 49 years of stewardship by the current owner.The 1.5 acre parcel is deep, with an open and private back yard. In the front, the parcel is bordered by ayear-round stream that is a tributary of the Roeliff Jansen Kill. Collins Street is

  Margaret Bower Avenia Columbia County RE Specialist

  44 Collins St, Hillsdale, NY 12529
• 

  

  /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 $404,836

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

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

Showing Results 41 - 80, Page 2 of 18