Hillsdale, NY Homes

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  /58

  $686,000

  Sold Jul 30, 2026

  534 Collins St, Hillsdale, NY 12529

  • 2 Beds
  • 2.5 Baths
  • 2,060 Sq Ft
  • Built 1975

  Last Sold Summary

  • 10% Above List Price
  • $333/SF
  • 17 Days On Market

  Current Estimated Value $621,452

  Last Listing Agent John Barbato Compass, Hillsdale

  534 Collins St, Hillsdale, NY 12529
• 

  

  

  /11

  Est $488,954

  Not Listed For Sale

  40 Marsten Ln, Hillsdale, NY 12529

  • 4 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • Built 1976

  40 Marsten Ln, Hillsdale, NY 12529

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Peter Darrell Tri Hudson Realty, LLC
• 

  

  

  /44

  $1,485,000

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  51 Taconic Creek Rd, Hillsdale, NY 12529

  This perfect modern farmhouse retreat is tucked away on one of Columbia County's most quiet and beautiful roads guaranteeing a tranquil respite from the city. Being one of just a handful of properties on the road creates a sense of peace and quiet that is unmatched. While a feeling of simplicity emanates throughout the land there is a clear level of sophistication in the design details. The

  Thomas Pawlowski Four Seasons Sotheby's Int.

  51 Taconic Creek Rd, Hillsdale, NY 12529
• 

  $850,000

  Sold Feb 24, 2026

  9254 New York 22, Hillsdale, NY 12529

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft
  • Built 1980

  Last Sold Summary

  • 8% Above List Price
  • $340/SF
  • 16 Days On Market

  Last Listing Agent David Birch Barns and Farms Realty LLC

  9254 New York 22, Hillsdale, NY 12529
• 

  

  /2

  Est $932,861

  Not Listed For Sale

  137 Whippoorwill Rd, Hillsdale, NY 12529

  • 4 Beds
  • 3 Baths
  • 2,322 Sq Ft
  • Built 1910

  137 Whippoorwill Rd, Hillsdale, NY 12529
• 

  

  /41

  $2,195,000

  • 3 Beds
  • 3 Baths
  • 2,755 Sq Ft

  292 White Hill Rd, 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 captures 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 Rd, Hillsdale, NY 12529
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  /4

  $81,000

  Sold Jan 27, 2026

  0 Rodman Rd, Hillsdale, NY 12529

  • Land
  • 4.4 Acres
  • $18,409 per Acre

  Last Sold Summary

  • 2% Above List Price
  • 14 Days On Market

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

  0 Rodman Rd, Hillsdale, NY 12529
• 

  

  /25

  Est $796,254

  Not Listed For Sale

  274 Texas Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,272 Sq Ft
  • Built 2002

  274 Texas Hill Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Lori Mendelis Past Member
• 

  

  /23

  $305,000

  $15K PRICE INCREASE Pending

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  9377 State Route 22, Hillsdale, NY 12529

  BACK ON MARKET!! Welcome home to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard

  Scott Zobre KW MidHudson

  9377 State Route 22, Hillsdale, NY 12529
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  /4

  $199,999

  Sold Dec 31, 2025

  2605 New York 23, Hillsdale, NY 12529

  • 5 Beds
  • 3 Baths
  • 2,578 Sq Ft
  • Built 1890

  Last Sold Summary

  • $78/SF
  • 40 Days On Market

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

  2605 New York 23, Hillsdale, NY 12529
• 

  Est $807,310

  Not Listed For Sale

  62 Bucky Rd, Hillsdale, NY 12529

  • 4 Beds
  • 3 Baths
  • 3,034 Sq Ft
  • Built 1960

  62 Bucky Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 110 Days On Market

  Last Listing Agent Ronald Green KW MidHudson
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  /26

  $1,100,000

  $175K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 1,700 Sq Ft

  401 Collins St, 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 Sothebys Intl

  401 Collins St, Hillsdale, NY 12529
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  /46

  $3,245,000

  Sold Jun 08, 2026

  411 Texas Hill Rd, Hillsdale, NY 12529

  • 4 Beds
  • 4 Baths
  • 4,000 Sq Ft
  • Built 1967

  Last Sold Summary

  • 3% Below List Price
  • $811/SF
  • 32 Days On Market

  Current Estimated Value $3,307,101

  Last Listing Agent Marina Tatistcheff Compass Greater NY LLC

  411 Texas Hill Rd, Hillsdale, NY 12529
• 

  

  /29

  Est $1,221,813

  Not Listed For Sale

  90 Overlook Dr, Hillsdale, NY 12529

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

  90 Overlook Dr, Hillsdale, NY 12529

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Jennifer Harvey Compass Greater NY LLC
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  /30

  $619,000

  $30K PRICE DROP

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

  416 Whippoorwill Rd, Hillsdale, NY 12529

  This one checks all of the boxes. Our newly listed two bedroom, two bath Cape Cod style home in Hillsdale has been meticulously maintained and is in excellent condition inside and out. The main level features a functional kitchen, dining area, bathroom, and living room centered around a propane fireplace; all with hardwood floors. A 12x12 great room with hardwood floors was added to provide

  Margaret Bower Avenia Columbia County RE Specialist

  416 Whippoorwill Rd, Hillsdale, NY 12529
• 

  $515,000

  Sold Jun 16, 2026

  180 Collins St, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1906

  Last Sold Summary

  • 14% Above List Price
  • $418/SF
  • 9 Days On Market

  Current Estimated Value $498,006

  Last Listing Agent Joseph Shirk The Kinderhook Group, Inc.

  180 Collins St, Hillsdale, NY 12529
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  /42

  Est $1,350,367

  Not Listed For Sale

  864 W End Rd, Hillsdale, NY 12529

  • 4 Beds
  • 3.5 Baths
  • 3,540 Sq Ft
  • Built 2003

  864 W End Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent John Barbato Compass, Hillsdale
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  /5

  $259,000

  • Land
  • 15.47 Acres
  • $16,742 per Acre

  191 Berkshire Rd, Hillsdale, NY 12529

  Discover the perfect opportunity to build your dream home on this expansive 15.47-acre parcel at 191 Berkshire Road, bordering Copake Country Club and just minutes from Copake Lake. This fully undeveloped property is part of the desirable Sam Hill Road community, offering shared waterfront access through the HOA. Ideally located just 25 minutes from Hudson and Great Barrington, MA, you'll enjoy

  Austin Urban Venture Fox Realty Group

  191 Berkshire Rd, 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 Backhaus William Raveis Real Estate

  25 Catamount Rd, Hillsdale, NY 12529
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  /25

  Est $602,249

  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

  • 46 Days On Market

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
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  /7

  $255,000

  $4K PRICE DROP

  • 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 1395/m. Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is 795 + 550. Ideal for live/work. Building in excellent condition, roof less than 5 years old.

  David Birch Barns & Farms Realty, LLC

  9249 Route 22 Rd, Hillsdale, NY 12516
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  /28

  $450,000

  Sold Jun 18, 2026

  364 Yonderview Rd, Hillsdale, NY 12529

  • 4 Beds
  • 5 Baths
  • 3,425 Sq Ft
  • Built 1850

  Last Sold Summary

  • 16% Below List Price
  • $131/SF
  • 7 Days On Market

  Current Estimated Value $557,163

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

  364 Yonderview Rd, Hillsdale, NY 12529
• 

  

  /37

  Est $671,549

  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

  • 61 Days On Market

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
• 

  

  /19

  $392,500

  • 2 Beds
  • 2 Baths
  • 1,494 Sq Ft

  155 Pumpkin Hollow Rd N, Hillsdale, NY 12529

  Colonial Home on a Beautiful Country Parcel with New Garage Nestled on a peaceful country road, this charming two-bedroom Colonial offers the perfect blend of privacy, comfort, and convenience. Set back from the road on a beautiful parcel, the home welcomes you into a bright, open-concept living and dining area filled with natural light and complemented by attractive hardwood floors. The

  Jonathan Scarinzi Elyse Harney Real Estate

  155 Pumpkin Hollow Rd N, 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 $253,806

  Last Listing Agent Sarah Lipsky William Pitt Sothebys Intn'l

  49 Stonehill Dr, Hillsdale, NY 12529
• 

  Est $1,581,560

  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

  • 57 Days On Market

  Last Listing Agent John Panzer Elyse Harney Real Estate
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  /51

  $729,900

  • 3 Beds
  • 2.5 Baths
  • 2,210 Sq Ft

  417 Overlook Dr, Hillsdale, NY 12529

  Discover Your Dream Cape-Style Home: A Serene Escape on 2.1 Acres Nestled in a tranquil setting, this stunning Cape-style home offers the perfect blend of comfort and luxury, with 2.1 acres of nature at your doorstep. Imagine sipping your morning coffee on the spacious front porch while listening to the gentle rustle of leaves around you. Step inside to an inviting and dramatic living room, where

  Barbara Robinson Red Apple Realty

  417 Overlook Dr, Hillsdale, NY 12529
• 

  

  /26

  $1,037,500

  Sold Apr 28, 2026

  9715 New York 22, Hillsdale, NY 12529

  • 5 Beds
  • 2.5 Baths
  • 3,350 Sq Ft
  • Built 1788

  Last Sold Summary

  • 6% Below List Price
  • $310/SF
  • 160 Days On Market

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

  9715 New York 22, Hillsdale, NY 12529
• 

  

  /28

  Est $417,897

  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

  • 211 Days On Market

  Last Listing Agent Wendy Kenney Davala Real Estate, LLC
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  /7

  $95,000

  • Land
  • 12.95 Acres
  • $7,336 per Acre

  00 Stone Ledge Rd, Hillsdale, NY 12529

  Quiet location next to the Berkshires. Dead end road with a 12 acre parcel. Hiking trails throughout. Glorious views off the top. Great value. More land available.

  Tracy Tassinari Gabel Real Estate

  00 Stone Ledge Rd, Hillsdale, NY 12529
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  /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 $516,432

  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

  • 142 Days On Market

  Last Listing Agent Amjad Mughal M J J Realty
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  /36

  $749,000

  • 3 Beds
  • 2 Baths
  • 2,040 Sq Ft

  695 Wolf Hill Rd, Hillsdale, NY 12529

  This country home is nestled on 8.7 private acres just five miles from the center of Hillsdale, this charming retreat offers the perfect blend of comfort, character, and natural beauty. A meandering driveway winds through the woods, leading to a welcoming cottage-style home surrounded by perennial gardens filled with native ferns and plantings.The inviting covered front porch opens to a

  Kimberly Baker BHHS Hudson Valley Properties

  695 Wolf Hill Rd, Hillsdale, NY 12529
• 

  

  /36

  $580,000

  Sold Jun 12, 2026

  2657 State Route 23, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,057 Sq Ft
  • Built 1780

  Last Sold Summary

  • 11% Below List Price
  • $282/SF
  • 244 Days On Market

  Current Estimated Value $587,474

  Last Listing Agent John Barbato Compass, Hillsdale

  2657 State Route 23, Hillsdale, NY 12529
• 

  

  /27

  Est $889,198

  Not Listed For Sale

  66 Fado Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,421 Sq Ft
  • Built 1850

  66 Fado Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 368 Days On Market

  Last Listing Agent John Avenia Columbia County RE Specialist
• 

  

  /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

  11 Cold Water St, Hillsdale, NY 12529
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  /114

  Est $3,070,135

  Not Listed For Sale

  184A Cambridge Rd, Hillsdale, NY 12529

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

  184A Cambridge Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 35 Days On Market

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

  

  /21

  $339,900

  $60K PRICE DROP

  • 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
• 

  $1,150,000

  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 $1,082,575

  Last Listing Agent Nancy Felcetto Brown Harris Stevens HV LLC

  306 County Route 21c, Ghent, NY 12075

Showing Results 41 - 80, Page 2 of 18