Hillsdale, NY Homes

• 

  $1,037,500

  Sold Apr 28, 2026

  9715 State Route 22, Hillsdale, NY 12529

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

  Last Sold Summary

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

  Current Estimated Value $1,079,888

  Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

  9715 State Route 22, Hillsdale, NY 12529
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  /2

  Not Listed For Sale

  0 Justice Rd, Hillsdale, NY 12529

  0 Justice Rd, Hillsdale, NY 12529
• 

  

  

  /31

  $725,000

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

  2999 New York 23, Hillsdale, NY 12529

  2999 Route 23, Hillsdale, New York - Historic Country Estate on 12.5 Acres Step into a piece of living history with this beautifully preserved 1915 home, perfectly situated on a private 12.5-acre parcel in the heart of the Berkshires. Offering four generous bedrooms and three baths (2 full, 1 Half), this classic residence blends timeless charm with everyday comfort, creating an ideal setting for

  Tyler Bervy Stone House Properties, LLC

  2999 New York 23, Hillsdale, NY 12529
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  /47

  $825,000

  Sold Mar 27, 2026

  110 Meadow Ln, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1979

  Last Sold Summary

  • 17% Below List Price
  • $458/SF
  • 176 Days On Market

  Current Estimated Value $855,821

  Last Listing Agent John Avenia Columbia County RE Specialist

  110 Meadow Ln, Hillsdale, NY 12529
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  /33

  Not Listed For Sale

  287 New York 71, Hillsdale, NY 12529

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

  287 New York 71, Hillsdale, NY 12529

  Last Sold Summary

  • 26 Days On Market
• 

  

  /25

  $1,250,000

  $245K PRICE DROP Pending

  • 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
• 

  /2

  $1,250,000

  Sold Mar 09, 2026

  0 La Branche Rd Unit 248871, Hillsdale, NY 12529

  • Land
  • 203 Acres
  • $6,158 per Acre

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  0 La Branche Rd Unit 248871, Hillsdale, NY 12529
• 

  

  /20

  Est $490,148

  Not Listed For Sale

  3133 County Route 7, Copake, NY 12516

  • 2 Beds
  • 1 Bath
  • 1,494 Sq Ft
  • Built 1951

  3133 County Route 7, Copake, NY 12516

  Last Sold Summary

  • 73 Days On Market
• 

  

  /34

  $695,000

  $24K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,475 Sq Ft

  81 Black Grocery Rd, Hillsdale, NY 12529

  On a quiet country road, sit's the prettiest sunshine yellow house you've ever seen.Welcome to a property where outdoor splendor and indoor comfort merge seamlessly, where everything has been taken care of, and all you need to do is arrive and exhale. Rolling hills and open farmland stretch out before you, and they're all yours to enjoy.Inside, the dining room flows into an open kitchen

  Shaina Marron Houlihan Lawrence Inc.

  81 Black Grocery Rd, Hillsdale, NY 12529
• 

  $1,100,000

  Sold Sep 05, 2025

  228 County Road 21, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft
  • Built 1942

  Last Sold Summary

  • 7% Below List Price
  • $517/SF
  • 78 Days On Market

  Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

  228 County Road 21, Hillsdale, NY 12529
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  /11

  Not Listed For Sale

  10118 State Route 22, Hillsdale, NY 12529

  10118 State Route 22, Hillsdale, NY 12529

  Last Sold Summary

  • 332 Days On Market
• 

  

  /31

  $995,000

  • 2 Beds
  • 2 Baths
  • 2,060 Sq Ft

  17 Memory Ln, Hillsdale, NY 12529

  Lakefront living in one of the most peaceful and serene locations on Copake Lake. An expansive 75 feet of private waterfront with an existing dock, this charming home offers beautiful eastern views across the lake, where sunrises and tranquil water vistas become part of everyday life.The home's inviting open-concept layout has a spacious kitchen, dining, and living area. A first-floor primary

  John Barbato Compass, Hillsdale

  17 Memory Ln, Hillsdale, NY 12529
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  /2

  $94,000

  Sold Sep 16, 2025

  76 New York 71, Hillsdale, NY 12529

  • Land
  • 6 Acres
  • $15,667 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 472 Days On Market

  Last Listing Agent Rochelle Bartolo Beach & Bartolo Realtors

  76 New York 71, Hillsdale, NY 12529
• 

  Est $1,406,167

  Not Listed For Sale

  60 River Rd, Austerlitz, NY 12017

  • 4 Beds
  • 4 Baths
  • 2,626 Sq Ft
  • Built 1890

  60 River Rd, Austerlitz, NY 12017

  Last Sold Summary

  • 9 Days On Market
• 

  

  /26

  $1,150,000

  $125K PRICE DROP

  • 1 Bed
  • 2 Baths
  • 1,700 Sq Ft

  401 Collins St Unit Stop 11, 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. Plans are available for a one or two bedroom

  Pamela King-Belfor Four Seasons Sotheby's Int.

  401 Collins St Unit Stop 11, Hillsdale, NY 12529
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  /38

  $635,000

  Sold Oct 24, 2025

  47 Cherokee Dr, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Below List Price
  • $509/SF
  • 98 Days On Market

  Current Estimated Value $674,859

  Last Listing Agent Arlena Armstrong Anatole House LLC

  47 Cherokee Dr, Hillsdale, NY 12529
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  /3

  Not Listed For Sale

  10695 Ny-22, Hillsdale, NY 12529

  10695 Ny-22, Hillsdale, NY 12529

  Last Sold Summary

  • 39 Days On Market
• 

  

  /28

  $795,000

  $787K PRICE INCREASE

  • 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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  /41

  $2,000,000

  Sold Nov 18, 2025

  250 Island Dr, Craryville, NY 12521

  • 3 Beds
  • 3 Baths
  • 2,720 Sq Ft
  • Built 2000

  Last Sold Summary

  • 20% Below List Price
  • $735/SF
  • 495 Days On Market

  Current Estimated Value $2,109,982

  Last Listing Agent John Barbato Compass, Hillsdale

  250 Island Dr, Craryville, NY 12521
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  /32

  Not Listed For Sale

  2653 New York 23, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Built 1970

  2653 New York 23, Hillsdale, NY 12529

  Last Sold Summary

  • 27 Days On Market
• 

  

  /54

  $1,100,000

  • 3 Beds
  • 4 Baths
  • 2,880 Sq Ft

  2666 New York 23, Hillsdale, NY 12529

  Unique investment opportunity in the hamlet of Hillsdale. This new-to-the-market commercial/residential property has been meticulously renovated by the current owner, a commercial builder, who over-engineered the project with high-end features throughout. The property consists of four distinct rental units:2666 Route 23, Main (Blue) Building- First-Floor Commercial Unit Right Side: 360

  Margaret Bower Avenia Columbia County RE Specialist

  2666 New York 23, Hillsdale, NY 12529
• 

  

  /33

  Est $3,940,796

  Not Listed For Sale

  256 Island Dr, Copake, NY 12521

  • 5 Beds
  • 2 Baths
  • 5,300 Sq Ft
  • Built 2014

  256 Island Dr, Copake, NY 12521

  Last Sold Summary

  • 36 Days On Market
• 

  

  /55

  $1,525,000

  • 4 Beds
  • 4.5 Baths
  • 3,666 Sq Ft

  83 Schmeichel Rd, Hillsdale, NY 12529

  Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with a vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a

  Jennifer Harvey Compass Greater NY LLC

  83 Schmeichel Rd, Hillsdale, NY 12529
• 

  

  /20

  Not Listed For Sale

  0 W End Rd, Hillsdale, NY 12529

  0 W End Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 24 Days On Market
• 

  

  /30

  $1,195,000

  $805K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft

  75 Upper Hollow Rd, Hillsdale, NY 12529

  A rare 193-acre estate in Austerlitz/Hillsdale, very close to the Berkshire border. The charming 3-bed cottage overlooks a pristine pond with a bordering creek. The wooded land has clearly marked and maintained hiking trails. Recently renovated, the cottage features an updated bathroom and an expanded living room, blending modern comfort with rustic charm. Geothermal heating and air conditioning

  Janet Kain The Kinderhook Group, Inc.

  75 Upper Hollow Rd, Hillsdale, NY 12529
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  /26

  Not Listed For Sale

  2871 New York 23, Hillsdale, NY 12529

  • 29 Beds
  • 28 Baths
  • 3,000 Sq Ft
  • Built 1920

  2871 New York 23, Hillsdale, NY 12529

  Last Sold Summary
• 

  

  /13

  $1,080,000

  $5K PRICE INCREASE

  • Land
  • 72 Acres
  • $15,000 per Acre

  0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529

  Picturesque farmland located close to the Village of Hillsdale, only 1.8 to Catamount Ski Area, and 9.5 miles to Great Barrington. Extensive road frontage, totaling 3979 feet on Yonderview Road and Route 23. Barn complex. This parcel is zoned RU in the Town of Hillsdale. Property currently enjoys an agricultural exemption. Survey available. Inspect Now!

  Robert D Ferris R. Ferris Real Estate, LLC

  0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529
• 

  

  /17

  Est $399,911

  Not Listed For Sale

  2951 State Route 23, Hillsdale, NY 12529

  • 2 Beds
  • 1.5 Baths
  • 1,111 Sq Ft
  • Built 1930

  2951 State Route 23, Hillsdale, NY 12529

  Last Sold Summary

  • 62 Days On Market
• 

  

  /28

  $4,950,000

  $2M PRICE DROP

  • 6 Beds
  • 6 Baths
  • 6,309 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 84 acres, hasbeen listed in Interior Design magazine. The main house is a stunning post and beam contemporary home, combining steel, glass, wood and stone panels. It overlooks the gunite pool, surrounded by stone walls and the two additional designed and inviting cottages. Continuing past

  Janet Kain The Kinderhook Group, Inc.

  890 Bald Mountain Rd, Austerlitz, NY 12017
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  /2

  Not Listed For Sale

  361 Craryville Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft
  • Built 1900

  361 Craryville Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 375 Days On Market
• 

  

  /20

  $1,695,000

  • Land
  • 127 Acres
  • $13,346 per Acre

  0 Mitchell St Unit 249980, 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

  Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  0 Mitchell St Unit 249980, Hillsdale, NY 12529
• 

  

  /26

  Est $301,894

  Not Listed For Sale

  431 SW Colony Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1952

  431 SW Colony Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 79 Days On Market
• 

  

  /17

  $399,000

  $150K PRICE DROP

  • Land
  • 83.22 Acres
  • $4,795 per Acre

  50 - 61 Dugway Rd, Hillsdale, NY 12529

  Located between the charming towns of Chatham, NY, and Great Barrington, MA, this 83 acre parcel offers you exceptional potential awaiting your vision, and ideal escape. Two adjoining proprieties come together to form this large property that is a unique blend of privacy and accessibility. Enjoy impressive road frontage on two roads that in total offer is over 33,000 feet of frontage ensuring

  Jeffrey McKinney Beach & Bartolo Realtors

  50 - 61 Dugway Rd, Hillsdale, NY 12529
• 

  

  /25

  Not Listed For Sale

  184 Overlook Dr, Hillsdale, NY 12529

  • 4 Beds
  • 2 Baths
  • 2,126 Sq Ft
  • Built 1910

  184 Overlook Dr, Hillsdale, NY 12529

  Last Sold Summary

  • 73 Days On Market
• 

  

  /44

  $1,250,000

  $45K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,395 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
• 

  

  /36

  Not Listed For Sale

  208 Cambridge Rd, Hillsdale, NY 12529

  • 3 Beds
  • 3.5 Baths
  • 2,384 Sq Ft
  • Built 1981

  208 Cambridge Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 56 Days On Market
• 

  

  /12

  $95,000

  • Land
  • 6.25 Acres
  • $15,200 per Acre

  0 Stone Ledge Rd, Hillsdale, NY 12529

  Quiet parcel with a small cabin and a shed. Shed with loft area and porch. Nestled on a dead end road in Hillsdale. Cleared paths with trails. Quiet location close to MA. Great value.

  Tracy Tassinari Gabel Real Estate

  0 Stone Ledge Rd, Hillsdale, NY 12529
• 

  

  /23

  Est $725,527

  Not Listed For Sale

  161 White Hill Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 1,310 Sq Ft
  • Built 1996

  161 White Hill Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 69 Days On Market
• 

  

  /26

  $1,195,000

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

  523 Breezy Hill Rd, Hillsdale, NY 12529

  Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The

  Mimi Harson William Pitt Sotheby's

  523 Breezy Hill Rd, Hillsdale, NY 12529
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  /3

  Not Listed For Sale

  0 Connelly - Off Unit 137624, Copake, NY 12517

  0 Connelly - Off Unit 137624, Copake, NY 12517

  Last Sold Summary

  • 151 Days On Market

Showing Results 121 - 160, Page 4 of 18