Hillsdale, NY Homes

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  $895,000

  • 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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  $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

  • 2 Beds
  • 1 Bath
  • 1,896 Sq Ft

  39 - stop 26 Justice Rd, Hillsdale, NY 12529

  39 - stop 26 Justice Rd, Hillsdale, NY 12529
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  $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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  $1,950 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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  $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

  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
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  $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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  /10

  $4,500 per month

  • 4 Beds
  • 3 Baths
  • 2,349 Sq Ft
  • House for Rent

  125 Taconic Creek Rd, Hillsdale, NY 12529

  Hillsdale, NY Rental Available only December 18 to February 28.: Private, scenic 4-bedroom, 3-bath country home. This peaceful retreat features a cozy wood stove, a well-appointed kitchen, and is offered fully furnished with tasteful, comfortable pieces throughout. Enjoy quiet rural living just minutes from Catamount Mountain Resort. All utilities included, bring your streaming hardware of your

  Rochelle Bartolo Beach & Bartolo Realtors

  125 Taconic Creek Rd, Hillsdale, NY 12529
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  $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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  Not Listed For Sale

  0 Mitchell St Unit 132496, Hillsdale, NY 12529

  0 Mitchell St Unit 132496, Hillsdale, NY 12529
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  $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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  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • House for Rent

  765 Harlemville Rd, Hillsdale, NY 12529

  Tucked up against hill and overlooking farmland, you'll find this peaceful retreat, a Harlemville hideaway. This furnished home is available for a 5 month lease thru June 28th. The perfect spot if you are looking to get away to the country but still want to be within reach of amenities or you want or need to be close to Hawthorne Valley which is only a 2 min drive or 10 min walk away. The house,

  Jennifer Sesma Beach & Bartolo Realtors

  765 Harlemville Rd, 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 $1,329,803

  Last Listing Agent John Barbato Compass, Hillsdale

  864 W End Rd, Hillsdale, NY 12529
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  Est $1,129,422 Not Listed For Sale

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

  27 Maple St, Hillsdale, NY 12529

  27 Maple St, Hillsdale, NY 12529
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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 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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  $15,000 per month

  • 5 Beds
  • 3.5 Baths
  • 3,630 Sq Ft
  • House for Rent

  136 Tory Hill Farm Rd, Hillsdale, NY 12529

  Perched high on a quiet mountainside in one of Hillsdale's most coveted locations, this modern farmhouse sanctuary set on 50+ private acres blends timeless Hudson Valley romance with the ease of updated, contemporary living. Accessed via a private road and tucked discreetly into the hillside, this calming and zen-like retreat offers complete privacy—just minutes from the center of town.

  Matthew Snyder Compass, Hillsdale

  136 Tory Hill Farm Rd, 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 $541,208

  Last Listing Agent Donna Peck Copake Realty

  15 Roosevelt Dr, Hillsdale, NY 12529
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  Est $1,657,125 Not Listed For Sale

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

  172 W End Rd, Hillsdale, NY 12529

  172 W End Rd, Hillsdale, NY 12529
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  $1,250,000

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

  161 Stagecoach Rd, Hillsdale, NY 12529

  Architecture meets nature in Hillsdale. A fully secluded getaway at the end of a private dead-end road on 7.3 pristine acres. This sunny 3-bedroom, 2-1/2 bath house is inspired by Scandinavian design and features 3 outdoor decks, with views of a spring-fed stream, a crystal clear pond, and deep green woodlands. Central AC for summer days and a wood stove for snowy nights. An ideal layout for

  Owen Davidson Brown Harris Stevens HV LLC

  161 Stagecoach Rd, Hillsdale, NY 12529
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  $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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  $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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  /11

  Est $515,939 Not Listed For Sale

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

  40 Marsten Ln, Hillsdale, NY 12529

  40 Marsten Ln, Hillsdale, NY 12529
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  $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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  $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

  Last Listing Agent John Avenia Columbia County RE Specialist

  15 Tory Hill Rd, Hillsdale, NY 12529
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  Est $798,634 Not Listed For Sale

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

  137 Whippoorwill Rd, Hillsdale, NY 12529

  137 Whippoorwill Rd, Hillsdale, NY 12529
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  $999,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  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 Houlihan Lawrence

  25 Nobletown Rd, 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 $1,191,000

  Last Listing Agent Claudia Crane COMPASS MASSACHUSETTS , LLC GB

  523 Breezy Hill Rd, Hillsdale, NY 12529
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  Est $804,978 Not Listed For Sale

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

  274 Texas Hill Rd, Hillsdale, NY 12529

  274 Texas Hill Rd, Hillsdale, NY 12529
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  $895,000

  • 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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  $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

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

  271 Texas Hill Rd, Hillsdale, NY 12529
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  Est $721,940 Not Listed For Sale

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

  62 Bucky Rd, Hillsdale, NY 12529

  62 Bucky Rd, Hillsdale, NY 12529
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  $6,950,000

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

  890 Bald Mountain Rd, Austerlitz, NY 12017

  Located in a private gated community of large acreage land holders, this exquisite enclave of 3 homes on 85 acres has been listed in Interior Design magazine. The main house is a stunning post and beam contemporary home, combining steel, stone, wood and glass panels. It overlooks the gunite pool, surrounded by stone walls and the two additional designed and inviting cottages. Continuing past the

  Janet Kain The Kinderhook Group, Inc.

  890 Bald Mountain Rd, Austerlitz, NY 12017
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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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  Est $662,379 Not Listed For Sale

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

  76 Overlook Dr, Hillsdale, NY 12529

  76 Overlook Dr, Hillsdale, NY 12529
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  $799,000

  • Land
  • 56.9 Acres
  • $14,042 per Acre

  3244 Cr 7, Hillsdale, NY 12529

  Beautiful 56+ private acres with views of Copake Lake and Catskill Mountain sunsets. After entering the gates, the forest lined driveway meanders to the sweet spot. There are plenty of options for a home site or 2! Be tucked away but so close to it all! Equidistant to Hudson, NY and Great Barrington, MA., there is so much the area has to offer. From Catamount Ski/Adventure Park to Tangelwood,

  Theresa Westlake Copake Lake Realty Corp.

  3244 Cr 7, 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 $633,813 Not Listed For Sale

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

  15 Henich Ln, Hillsdale, NY 12529

  15 Henich Ln, Hillsdale, NY 12529
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  $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

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