Hillsdale, NY Homes

• 

  

  

  /20

  Est $272,256

  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

  • 34 Days On Market

  Last Listing Agent Scott Varley KW Platform
• 

  

  

  /19

  $850,000

  • Land
  • 150 Acres
  • $5,667 per Acre

  400 Overlook Dr, Hillsdale, NY 12529

  Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

  MATTHEW CAREY Rouse + Co Real Estate

  400 Overlook Dr, Hillsdale, NY 12529
• 

  

  

  /29

  $450,000

  Sold Jul 08, 2026

  44 Collins St, Hillsdale, NY 12529

  • 2 Beds
  • 1.5 Baths
  • 1,630 Sq Ft
  • Built 1933

  Last Sold Summary

  • 6% Above List Price
  • $276/SF
  • 64 Days On Market

  Current Estimated Value $431,843

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist

  44 Collins St, Hillsdale, NY 12529
• 

  

  

  /13

  Est $414,721

  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

  • 38 Days On Market

  Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist
• 

  

  

  /22

  $365,000

  • 1 Bed
  • 1 Bath
  • 684 Sq Ft

  251 Overlook Dr, Hillsdale, NY 12529

  Are you dreaming of times spent tucked away in a rustic cabin, preferably wrapped in a cozy blanket in front of a roaring fireplace? Or maybe you're dreaming of barefoot in the stream that feds into the Green River and sunbathing with rays of sunshine beaming through the trees? Welcome to 251 Overlook, Hillsdale NY! Cira 1900 Cottage in the woods, built on the side of a mountain, on 4.5 Acres. A

  Margaret Bower Avenia Columbia County RE Specialist

  251 Overlook Dr, Hillsdale, NY 12529
• 

  

  /34

  $580,000

  Sold Jun 05, 2026

  66 Anthony St, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 2,300 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Below List Price
  • $252/SF
  • 112 Days On Market

  Last Listing Agent Susan Calkins STONE HOUSE PROPERTIES, LLC

  66 Anthony St, Hillsdale, NY 12529
• 

  

  /44

  Est $1,483,407

  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

  • 27 Days On Market

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

  

  /7

  $39,900

  • Land
  • 26,571 Sq Ft
  • $65,410 per Acre

  0 Prach Road Extension Unit 20263433, Claverack, NY 12513

  Take advantage of this opportunity to build your dream home on this cleared, flat, .61 acre parcel (with well on property). Conveniently located just minutes to Hudson's restaurants, shops, and Amtrak station, or if you prefer outdoor activities e.g. hiking, kayaking, skiing, and ariel adventure, it's all within a short drive to Bash Bish Falls State Park, Copake Lake, and Catamount Mountain

  Wendy Kenney Davala Real Estate, LLC

  0 Prach Road Extension Unit 20263433, Claverack, NY 12513
• 

  

  /23

  $460,000

  Sold Aug 13, 2026

  217 Anthony St, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,375 Sq Ft
  • Built 2026

  Last Sold Summary

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

  Last Listing Agent John Barbato Compass, Hillsdale

  217 Anthony St, Hillsdale, NY 12529
• 

  

  /20

  Est $355,327

  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

  • 35 Days On Market

  Last Listing Agent April Seney Venture Fox Realty Group
• 

  

  /35

  $1,145,000

  Pending

  • 3 Beds
  • 3.5 Baths
  • 2,750 Sq Ft

  42 Shepherd Hill Cir, Hillsdale, NY 12529

  Tucked down a private road and high in the hills of northern Hillsdale, this well-built home offers sweeping mountain views, a beautiful pool, and more than 12 completely private acres--all within 10 minutes of town and 15 minutes from Great Barrington. The house is outfitted with thoughtful details that make country living comfortable and easy--central cooling, ample storage in all the right

  Sarah Kardos Four Seasons Sotheby's Int'l R

  42 Shepherd Hill Cir, 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 $803,906

  Last Listing Agent Tom Lynch Compass Greater NY LLC

  470 N Mountain Rd, Copake Falls, NY 12517
• 

  

  /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

  • 32 Days On Market

  Last Listing Agent Barbara Robinson Red Apple Realty
• 

  

  /16

  $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
• 

  $1,183,000

  Sold Aug 10, 2026

  161 Stagecoach Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 1968

  Last Sold Summary

  • 21% Below List Price
  • $538/SF
  • 338 Days On Market

  Current Estimated Value $1,101,203

  Last Listing Agent Owen Davidson Brown Harris Stevens HV LLC

  161 Stagecoach Rd, 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 Listing Agent Austin Urban Venture Fox Realty Group
• 

  

  /19

  $850,000

  • Land
  • 150 Acres
  • $5,667 per Acre

  0 Overlook Dr, Hillsdale, NY 12529

  Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

  MATTHEW CAREY Rouse + Co Real Estate

  0 Overlook Dr, 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 $508,871

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

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

  Est $801,000

  Not Listed For Sale

  0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529

  • 4 Beds
  • Built 1960

  0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529

  Last Sold Summary

  • 219 Days On Market

  Last Listing Agent Robert D Ferris R. Ferris Real Estate, LLC
• 

  

  /13

  $299,000

  $96K PRICE DROP Under Contract

  • Land
  • 49.91 Acres
  • $5,991 per Acre

  61 Dugway Rd, Hillsdale, NY 12529

  Discover Your Dream Retreat: 49+ Acres of Serenity and Potential! Located 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

  Jeffrey McKinney Beach & Bartolo Realtors

  61 Dugway Rd, Hillsdale, NY 12529
• 

  

  /19

  $190,000

  Sold Jun 05, 2026

  2227 County Route 21, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 794 Sq Ft
  • Built 1950

  Last Sold Summary

  • 37% Below List Price
  • $239/SF
  • 362 Days On Market

  Last Listing Agent Michael Castellano Gilcrest Properties

  2227 County Route 21, Hillsdale, NY 12529
• 

  

  /10

  Not Listed For Sale

  10344 New York 22, Hillsdale, NY 12529

  • 5 Beds
  • 2 Baths
  • 2,541 Sq Ft
  • Built 1875

  10344 New York 22, Hillsdale, NY 12529

  Last Sold Summary

  • 281 Days On Market

  Last Listing Agent Parker Meyer Four Seasons Sotheby's Int.
• 

  

  /20

  $299,000

  $26K PRICE DROP

  • Land
  • 22.84 Acres
  • $13,091 per Acre

  0 County Route 21, Hillsdale, NY 12529

  Welcome to DREAMLAND.Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow--perfectly oriented for southern

  Pamela King-Belfor Four Seasons Sotheby's Int.

  0 County Route 21, Hillsdale, NY 12529
• 

  

  /41

  $786,000

  Sold Nov 20, 2025

  441 Overlook Dr, Hillsdale, NY 12529

  • 3 Beds
  • 3 Baths
  • 1,875 Sq Ft
  • Built 1940

  Last Sold Summary

  • 1% Below List Price
  • $419/SF
  • 50 Days On Market

  Current Estimated Value $775,583

  Last Listing Agent Jennifer Harvey Compass Greater NY LLC

  441 Overlook Dr, Hillsdale, NY 12529
• 

  

  /50

  Est $348,882

  Not Listed For Sale

  9376 New York 22, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,684 Sq Ft
  • Built 1951

  9376 New York 22, Hillsdale, NY 12529

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Nicholas Miuccio Miuccio Real Estate Group
• 

  

  /58

  $3,300,000

  • 4 Beds
  • 3 Baths
  • 5,760 Sq Ft

  124 Syre Ln, Hillsdale, NY 12529

  PRIVATE & QUIET ~ 124 Syre Lane, Hillsdale NYFederal Style Colonial home in Hillsdale, perched on the top of the mountain, pairing historical accuracy with state-of-the-art modern conveniences. This stately country home offers unparalleled, endless views in every direction of the valley and Catskill Mountains. Offering Immeasurable beauty, from every window and large back deck, perfect for

  Margaret Bower Avenia Columbia County RE Specialist

  124 Syre Ln, Hillsdale, NY 12529
• 

  

  /13

  $725,000

  Sold Jan 20, 2026

  2318 County Road 11, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,569 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $462/SF
  • 24 Days On Market

  Last Listing Agent Emma French Gabel Real Estate

  2318 County Road 11, Hillsdale, NY 12529
• 

  

  /13

  Est $267,000

  Not Listed For Sale

  149 Yonderview Rd, Hillsdale, NY 12529

  149 Yonderview Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent John O'Neill-Knasick eXp Realty
• 

  

  /37

  $695,000

  New Construction Pending

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  30 Ridge Ln, Hillsdale, NY 12529

  Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town.Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in

  John Barbato Compass, Hillsdale

  30 Ridge Ln, Hillsdale, NY 12529
• 

  $426,500

  Sold Sep 11, 2025

  69 SW Colony Rd, Hillsdale, NY 12529

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft
  • Built 2021

  Last Sold Summary

  • 10% Below List Price
  • $421/SF
  • 358 Days On Market

  Current Estimated Value $444,434

  Last Listing Agent Michelle Ayala BHHS Hudson Valley Properties

  69 SW Colony Rd, Hillsdale, NY 12529
• 

  

  /29

  Not Listed For Sale

  10247 Ny-22 --, Hillsdale, NY 12529

  • 3 Beds
  • 1.5 Baths
  • 1,556 Sq Ft
  • Built 1970

  10247 Ny-22 --, Hillsdale, NY 12529

  Last Sold Summary

  • 247 Days On Market

  Last Listing Agent Paige Backhaus WILLIAM RAVEIS - BERKSHIRE
• 

  

  /58

  $949,900

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  2955 New York 23, Hillsdale, NY 12529

  Steeped in Hillsdale's rich history, this extraordinary property began its life as one of the area's original grist mills, situated in the area of Hillsdale once known as Murray's Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

  Jason Walch Coldwell Banker Advisor Realty

  2955 New York 23, Hillsdale, NY 12529
• 

  

  /40

  $2,180,000

  Sold Mar 02, 2026

  35 Harlemville Rd, Hillsdale, NY 12529

  • 5 Beds
  • 5.5 Baths
  • 7,200 Sq Ft
  • Built 1980

  Last Sold Summary

  • 34% Below List Price
  • $303/SF
  • 441 Days On Market

  Current Estimated Value $1,882,841

  Last Listing Agent Non MLS HVCR MLS HV Catskill Region MLS

  35 Harlemville Rd, Hillsdale, NY 12529
• 

  Not Listed For Sale

  631 SW Colony Rd, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,219 Sq Ft
  • Built 1955

  631 SW Colony Rd, Hillsdale, NY 12529

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Angel Ayala BHHS Hudson Valley Properties
• 

  

  /33

  $890,000

  Under Contract

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

  49 Knapp Hollow Ln, Hillsdale, NY 12529

  On 5 park-like acres this well maintained and thoughtfully designed home overlooks a tranquil pond and offers a serene getaway. Designed by architect Dennis Wedlick to maximize space and ease of living the home features 3-4 bedrooms and 3 full baths of which one is a separate guest suite. A renovated kitchen and updated bathrooms blend seamlessly with gleaming wood floors. A striking double sided

  marylou Kersten COPAKE LAKE REALTY CORP.

  49 Knapp Hollow Ln, Hillsdale, NY 12529
• 

  

  /9

  $215,000

  Sold Nov 13, 2025

  10011 New York 22, Hillsdale, NY 12529

  • 3 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1975

  Last Sold Summary

  • 17% Below List Price
  • $207/SF

  Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

  10011 New York 22, Hillsdale, NY 12529
• 

  

  /34

  Est $2,372,749

  Not Listed For Sale

  383 Mitchell St, Hillsdale, NY 12529

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft
  • Built 2023

  383 Mitchell St, Hillsdale, NY 12529

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Nancy Felcetto Brown Harris Stevens Hudson
• 

  

  /43

  $795,000

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  65 Meadow Ln, Hillsdale, NY 12529

  With a view as far as the eye can see, 65 Meadow Lane, Hillsdale never fails to amaze from sunrise to sunset, as a full moon lights up your bedroom; hawks fly past wandering clouds, the fiery yellow and burnt red leaves of autumn and the pine trees dripping with snow like confectionary sugar in a winter wonderland. The only sounds you hear are woodpeckers and wild turkeys and your heartbeat

  Margaret Bower Avenia Columbia County RE Specialist

  65 Meadow Ln, Hillsdale, NY 12529
• 

  

  /85

  $3,850,000

  Sold Dec 05, 2025

  350 Tory Hill Farm Rd, Hillsdale, NY 12529

  • 4 Beds
  • 5 Baths
  • 5,998 Sq Ft
  • Built 2008

  Last Sold Summary

  • 4% Below List Price
  • $642/SF
  • 142 Days On Market

  Current Estimated Value $3,853,754

  Last Listing Agent John Barbato Compass, Hillsdale

  350 Tory Hill Farm Rd, Hillsdale, NY 12529
• 

  

  /25

  Not Listed For Sale

  0 Railroad Ln Unit 149543, Hillsdale, NY 12529

  0 Railroad Ln Unit 149543, Hillsdale, NY 12529

  Last Sold Summary

  • 257 Days On Market

  Last Listing Agent John Avenia Columbia County RE Specialist

Showing Results 81 - 120, Page 3 of 18