Hillsdale, NY Homes

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  $1,695,000

  • 4 Beds
  • 3 Baths
  • 2,608 Sq Ft

  46 Collins St, Hillsdale, NY 12529

  Welcome to Nobletown Farmhouse, a circa 1850 home on 2+ peaceful acres in prime Hillsdale, on one of Columbia County's prettiest country roads. This beautifully updated four-bedroom, three-bath antique farmhouse showcases the elegant proportions and craftsmanship of mid-19th century architecture, with designer finishes, modern systems, and a full complement of additional structures that make it a

  Anthony D'Argenzio Houlihan Lawrence Inc.

  46 Collins St, Hillsdale, NY 12529
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  /13

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  3191 New York 23 Unit 3, Hillsdale, NY 12529

  Well-maintained 2-bedroom, 1-bath apartment offering comfortable living with a functional layout. The unit features a bright living area, an updated kitchen with ample cabinetry, and two well-sized bedrooms with good natural light. The bathroom is clean and modern, with a full tub/shower. Enjoy easy access and sliding glass doors that open to a covered outdoor space—perfect for fresh air and

  Greg Berardi Berardi Realty

  3191 New York 23 Unit 3, Hillsdale, NY 12529
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  $25,000 Sold May 28, 2025

  0 Stonehill Dr, Hillsdale, NY 12529

  • Land
  • 0.96 Acre
  • $26,042 per Acre

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent David Birch Barns & Farms Realty, LLC

  0 Stonehill Dr, Hillsdale, NY 12529
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  /22

  Not Listed For Sale

  39 - stop 26 Justice Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 1,896 Sq Ft
  • Built 1984

  39 - stop 26 Justice Rd, Hillsdale, NY 12529

  Last Sold Summary

  • $203/SF
  • 69 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Kelsey Winters Davala Real Estate, LLC
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  /40

  $979,000

  • 3 Beds
  • 1.5 Baths
  • 1,293 Sq Ft

  44 SW Colony Rd, Hillsdale, NY 12529

  Set on the shores of Copake Lake, this charming waterfront home blends classic lake character with thoughtful modern updates. Offering three bedrooms and 1.5 baths, the home features a bright open kitchen, living, and dining area designed for easy lake living and entertaining. Recent renovations, including HVAC, septic system, and expansion to main floor, bring fresh style and comfort while

  Austin Urban Venture Fox Realty Group

  44 SW Colony Rd, Hillsdale, NY 12529
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  /14

  $1,950 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Apartment for Rent

  3191 New York 23 Unit 1, Hillsdale, NY 12529

  Well-maintained 2-bedroom, 1-bath ground-floor apartment (with limited steps) offering comfortable living with a functional layout. The unit features a bright living area, an updated kitchen with ample cabinetry, and two well-sized bedrooms with good natural light. The bathroom is clean and modern, with a full tub/shower. Enjoy easy access with ground-level entry and sliding glass doors that open

  Greg Berardi Berardi Realty

  3191 New York 23 Unit 1, Hillsdale, NY 12529
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  /30

  $650,000 Sold Dec 22, 2025

  63 Cherokee Dr, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,256 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $288/SF
  • 33 Days On Market

  Current Estimated Value $644,337

  Last Listing Agent Blanche Mackey Copake Lake Realty Corp.

  63 Cherokee Dr, Hillsdale, NY 12529
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  Not Listed For Sale

  0 - No# Justice Rd, Hillsdale, NY 12529

  0 - No# Justice Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 71 Days On Market

  Last Sold Price $32,500

  Last Listing Agent John Avenia Columbia County RE Specialist
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  $875,500

  • 4 Beds
  • 2.5 Baths
  • 2,225 Sq Ft

  2999 New York 23, Hillsdale, NY 12529

  Classic Country Home with Pond, Pool & Barns Located just minutes from Catamount Ski Area, Hudson, NY, and Great Barrington, MA. Steeped in history and charm, this distinctive residence—believed to date back to the late 1800s—offers timeless character with thoughtful updates and plenty of space to enjoy country living.This 4 BR, 2.5 BA, 2,225± sq. ft. home is sited on 12+ acres. The rocking

  Lindsay Lebrecht Copake Lake Realty Corp.

  2999 New York 23, Hillsdale, NY 12529
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  /10

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 1,107 Sq Ft
  • House for Rent

  419 SW Sw Colony Rd, Hillsdale, NY 12529

  Enjoy lake living at this cozy 2 bedroom 1 bath cottage at beautiful Copake Lake. Lake access providing the perfect spot to relax and swim. Conveniently located near local dining, outdoor recreation and just a short drive to Hudson, Great Barrington and the Taconic State Parkway. 18 month lease preferred. All utilities and maintenance responsibility of the tenant. Must have renters insurance and

  Theresa Westlake Copake Lake Realty Corp.

  419 SW Sw Colony Rd, Hillsdale, NY 12529
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  /18

  $500,000 Sold Jan 23, 2026

  2253 County Route 21, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,493 Sq Ft
  • Built 2021

  Last Sold Summary

  • 7% Below List Price
  • $335/SF
  • 124 Days On Market

  Last Listing Agent Jeffries Blackerby Houlihan Lawrence Inc.

  2253 County Route 21, Hillsdale, NY 12529
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  /10

  Not Listed For Sale

  199 Rt 217, Ghent, NY 12075

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

  199 Rt 217, Ghent, NY 12075

  Last Sold Summary

  • $292/SF
  • 99 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Kylah Campeta LYF Homes
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  /28

  $1,275,000

  • 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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  $1,350,000 Sold Jun 27, 2025

  864 W End Rd, Hillsdale, NY 12529

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

  Last Sold Summary

  • 4% Above List Price
  • $381/SF
  • 15 Days On Market

  Current Estimated Value $1,337,431

  Last Listing Agent John Barbato Compass, Hillsdale

  864 W End Rd, Hillsdale, NY 12529
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  /19

  Est $206,667 Not Listed For Sale

  22 Anthony St, Hillsdale, NY 12529

  • 5 Beds
  • 5 Baths
  • 2,502 Sq Ft
  • Built 1888

  22 Anthony St, Hillsdale, NY 12529

  Last Sold Summary

  • 8% Above List Price
  • $76/SF
  • 83 Days On Market

  Last Sold Price $191,000

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
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  $1,100,000 Under Contract

  • 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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  /20

  $605,000 Sold Sep 17, 2025

  15 Roosevelt Dr, Hillsdale, NY 12529

  • 1,080 Sq Ft
  • Built 1958

  Last Sold Summary

  • 34% Below List Price
  • $560/SF
  • 742 Days On Market

  Current Estimated Value $568,314

  Last Listing Agent Donna Peck Past Member

  15 Roosevelt Dr, Hillsdale, NY 12529
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  Not Listed For Sale

  105 Seekonk Rd, Hillsdale, NY 12529

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

  105 Seekonk Rd, Hillsdale, NY 12529

  Last Sold Summary

  • $306/SF

  Last Sold Price $347,000

  Last Listing Agent Paige Paluch WILLIAM RAVEIS - BERKSHIRE
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  /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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  /20

  $295,000 Sold Dec 30, 2025

  376 Approx Whippoorwill Rd, Hillsdale, NY 12529

  • Land
  • 12 Acres
  • $24,583 per Acre

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent John Avenia Columbia County RE Specialist

  376 Approx Whippoorwill Rd, Hillsdale, NY 12529
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  Est $1,033,687 Not Listed For Sale

  27 Maple St, Hillsdale, NY 12529

  • 4 Beds
  • 2.5 Baths
  • 2,538 Sq Ft
  • Built 1841

  27 Maple St, Hillsdale, NY 12529

  Last Sold Summary

  • 16% Below List Price
  • $483/SF
  • 122 Days On Market

  Last Sold Price $1,225,000

  Last Listing Agent Austin Urban Venture Fox Realty Group
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  /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 house to be built? This brand-new construction is being sold as it stands today, as a blank unfinished canvas 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

  Michael Castellano Gilcrest Properties

  801 Rodman Rd, Hillsdale, NY 12529
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  $725,000 Sold Dec 09, 2025

  15 Tory Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,592 Sq Ft
  • Built 2007

  Last Sold Summary

  • $280/SF
  • 45 Days On Market

  Current Estimated Value $722,024

  Last Listing Agent John Avenia Columbia County RE Specialist

  15 Tory Hill Rd, Hillsdale, NY 12529
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  Est $1,605,932 Not Listed For Sale

  172 W End Rd, Hillsdale, NY 12529

  • 3 Beds
  • 3 Baths
  • 3,263 Sq Ft
  • Built 1900

  172 W End Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 13% Below List Price
  • $437/SF

  Last Sold Price $1,425,000

  Last Listing Agent Lance Vermeulen LANCE VERMEULEN RE, INC
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  /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
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  $1,168,500 Sold Jul 11, 2025

  523 Breezy Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 1,931 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $605/SF
  • 44 Days On Market

  Current Estimated Value $1,202,692

  Last Listing Agent Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  523 Breezy Hill Rd, Hillsdale, NY 12529
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  /11

  Est $514,392 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

  • 56% Above List Price
  • $173/SF
  • 28 Days On Market

  Last Sold Price $329,000

  Last Listing Agent Peter Darrell Tri Hudson Realty, LLC
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  /28

  $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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  /29

  $965,000 Sold Dec 22, 2025

  271 Texas Hill Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,279 Sq Ft
  • Built 1930

  Last Sold Summary

  • $423/SF
  • 21 Days On Market

  Current Estimated Value $956,968

  Last Listing Agent Kelcey Otten Compass Greater NY, LLC d/b/a

  271 Texas Hill Rd, Hillsdale, NY 12529
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  Est $861,253 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

  Last Sold Summary

  • 16% Below List Price
  • $319/SF

  Last Sold Price $740,000

  Last Listing Agent marylou Kersten COPAKE LAKE REALTY CORP.
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  /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
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  $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
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  /25

  Est $783,603 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

  • 15% Above List Price
  • $299/SF
  • 41 Days On Market

  Last Sold Price $680,000

  Last Listing Agent Lori Mendelis Past Member
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  $895,000 Under Contract

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

  110 Meadow Ln, Hillsdale, NY 12529

  If your checklist for a new home includes any of the following, your search may have reached a successful conclusion. Let us introduce you to 110 Meadow Lane in Hillsdale NY. Views - Totally unique forever views that will inspire for a lifetimeLocation - Near the NY and MA border offering easy access to both Columbia County and the BerkshiresSingle-Story Living - A

  John Avenia Columbia County RE Specialist

  110 Meadow Ln, Hillsdale, NY 12529
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  $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
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  Est $717,432 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

  • 4% Above List Price
  • $228/SF
  • 110 Days On Market

  Last Sold Price $693,000

  Last Listing Agent Ronald Green KW MidHudson
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  $150,000 Under Contract

  • 4 Beds
  • 1 Bath
  • 2,116 Sq Ft

  10021 New York 22, Hillsdale, NY 12529

  Step back in time and imagine the possibilities with this charming 1800s farmhouse, situated on a picturesque 1-acre lot complete with a pond and stream. Nestled in a desirable area, this property offers a rare opportunity to restore and customize a true piece of history. The home features solid construction and ''great bones,'' providing a strong foundation for a full renovation. A spacious

  Paul Crayton Coldwell Banker Advisor Realty

  10021 New York 22, Hillsdale, NY 12529
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  $393,500 Sold Apr 15, 2025

  3002 State Route 23 --, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1975

  Last Sold Summary

  • 8% Below List Price
  • $304/SF
  • 59 Days On Market

  Last Listing Agent Paige Paluch WILLIAM RAVEIS - BERKSHIRE

  3002 State Route 23 --, Hillsdale, NY 12529
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  Est $646,330 Not Listed For Sale

  76 Overlook Dr, Hillsdale, NY 12529

  • 1 Bed
  • 1.5 Baths
  • 1,090 Sq Ft
  • Built 1979

  76 Overlook Dr, Hillsdale, NY 12529

  Last Sold Summary

  • 14% Above List Price
  • $518/SF
  • 6 Days On Market

  Last Sold Price $565,000

  Last Listing Agent Jennifer Harvey Compass Greater NY LLC
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  $5,950,000

  • 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 rustic elegance and architectural sophistication. The

  Janet Kain The Kinderhook Group, Inc.

  890 Bald Mountain Rd, Austerlitz, NY 12017

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