Homes in ZIP Code 12529

• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /9

  Not Listed For Sale

  25 Nicholson (Catamount) Rd, Copake, NY 12516

  • 1 Bed
  • 1 Bath
  • 620 Sq Ft
  • Built 1975

  25 Nicholson (Catamount) Rd, Copake, NY 12516

  Last Sold Summary

  • 14 Days On Market

  Last Listing Agent Karen Climo William Pitt Sothebys Intn'l
• 

  

  

  /30

  $575,000

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

  416 Whippoorwill Rd, Hillsdale, NY 12529

  PRIVATE SETTING!! Cape Cod style home, built in 2000, 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 additional living space.Ideally located on one of Hillsdale's

  Margaret Bower Avenia Columbia County RE Specialist

  416 Whippoorwill Rd, 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  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
• 

  

  /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
• 

  

  /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 $3,892,313

  Last Listing Agent John Barbato Compass, Hillsdale

  350 Tory Hill Farm Rd, Hillsdale, NY 12529
• 

  

  /23

  Not Listed For Sale

  50 Lake Ridge Ln, Craryville, NY 12521

  50 Lake Ridge Ln, Craryville, NY 12521

  Last Sold Summary

  • 36 Days On Market

  Last Listing Agent John Barbato Compass, Hillsdale
• 

  /2

  $299,000

  $96K PRICE DROP Pending

  • 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
• 

  

  /20

  $1,555,500

  Sold Sep 10, 2026

  0 Mitchell St Unit 249980, Hillsdale, NY 12529

  • Land
  • 127 Acres
  • $12,248 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 16 Days On Market

  Last Listing Agent Jen Harvey COMPASS MASSACHUSETTS , LLC GB

  0 Mitchell St Unit 249980, Hillsdale, NY 12529
• 

  

  /34

  Est $2,440,895

  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
• 

  

  /20

  $275,000

  $50K PRICE DROP

  • Land
  • 22.84 Acres
  • $12,040 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
• 

  

  /27

  $1,290,000

  Sold Nov 03, 2025

  120 Pumpkin Hollow Rd N, Hillsdale, NY 12529

  • 3 Beds
  • 3 Baths
  • 1,474 Sq Ft
  • Built 2025

  Last Sold Summary

  • $875/SF
  • 27 Days On Market

  Current Estimated Value $1,296,929

  Last Listing Agent Steven Gray Compass Greater NY, LLC d/b/a

  120 Pumpkin Hollow Rd N, 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
• 

  

  /58

  $849,900

  $150K 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

  Jason Walch Coldwell Banker Advisor Realty

  2955 New York 23, Hillsdale, NY 12529
• 

  

  /12

  $85,000

  Sold Aug 03, 2026

  449 New York 71, Hillsdale, NY 12529

  • Land
  • 25,264 Sq Ft
  • $146,552 per Acre

  Last Sold Summary

  • 13% Above List Price
  • 26 Days On Market

  Last Listing Agent Jessie Bennett William Pitt Sothebys Intn'l

  449 New York 71, Hillsdale, NY 12529
• 

  

  /31

  Not Listed For Sale

  615 County Route 21, Ghent, NY 12075

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft
  • Built 2002

  615 County Route 21, Ghent, NY 12075

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Beth DeMatteo Berkshire Hathaway HomeService
• 

  

  /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
• 

  

  /41

  $534,000

  Sold Oct 29, 2025

  58 Deer Track Ln, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1965

  Last Sold Summary

  • 1% Below List Price
  • $315/SF
  • 177 Days On Market

  Current Estimated Value $553,356

  Last Listing Agent Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

  58 Deer Track Ln, Hillsdale, NY 12529
• 

  

  /17

  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

  • 35 Days On Market

  Last Listing Agent Karen Davala Davala Real Estate LLC
• 

  

  /48

  $725,000

  $70K PRICE DROP

  • 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

  Margaret Bower Avenia Columbia County RE Specialist

  65 Meadow Ln, Hillsdale, NY 12529
• 

  $1,300,000

  Sold Jun 16, 2026

  143 Julianna Dr, Copake, NY 12516

  • 3 Beds
  • 3 Baths
  • 2,880 Sq Ft
  • Built 2019

  Last Sold Summary

  • 13% Above List Price
  • $451/SF
  • 13 Days On Market

  Current Estimated Value $1,262,033

  Last Listing Agent TRACY DOBER Rouse + Co Real Estate LLC

  143 Julianna Dr, Copake, NY 12516
• 

  /2

  Not Listed For Sale

  0 Justice Rd, Hillsdale, NY 12529

  0 Justice Rd, Hillsdale, NY 12529
• 

  

  /9

  $85,000

  • Land
  • 11.09 Acres
  • $7,665 per Acre

  0 Ny 22 Unit 20264890, Hillsdale, NY 12529

  So many possibilities for this 11 acre parcel on Route 22. Approximately 240 feet of road frontage provides options for a driveway up hill to flat land and eastern views The property is currently wooded. The upper land had been cleared over 30 years ago. Use this property to build your home or for hunting. Close to The Berkshires, Great Barrington

  Peter Newman Beach & Bartolo Realtors

  0 Ny 22 Unit 20264890, Hillsdale, NY 12529
• 

  

  /22

  $820,000

  Sold Jan 30, 2026

  75 Upper Hollow Rd, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,419 Sq Ft
  • Built 1988

  Last Sold Summary

  • 25% Below List Price
  • $578/SF
  • 161 Days On Market

  Current Estimated Value $1,302,087

  Last Listing Agent Janet Kain The Kinderhook Group, Inc.

  75 Upper Hollow Rd, Hillsdale, NY 12529
• 

  

  /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

  Last Listing Agent Peter Newman Beach & Bartolo Realtors
• 

  

  /30

  $995,000

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  2227 New York 23, Hillsdale, NY 12529

  COUNTRY CONTEMPORARY RANCH ON 9.5 ACRES WITH FOREVER WILD VIEWSA truly special country getaway, this distinctive 3-bedroom, 2-bath contemporary home is set on 9.5 beautiful acres with sweeping views of protected farmland and forever-wild Audubon sanctuary lands. Designed to embrace its natural surroundings, the home enjoys southern exposure and passive solar orientation, creating a warm

  Theresa Westlake Copake Lake Realty Corp.

  2227 New York 23, Hillsdale, NY 12529
• 

  $1,150,000

  Sold Jul 31, 2026

  1 Van Buren Dr, Copake, NY 12516

  • 5 Beds
  • 3 Baths
  • 2,548 Sq Ft
  • Built 1988

  Last Sold Summary

  • $451/SF
  • 25 Days On Market

  Current Estimated Value $1,126,613

  Last Listing Agent Craig Smith Compass Greater NY, LLC

  1 Van Buren Dr, Copake, NY 12516
• 

  

  /20

  Est $511,783

  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

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.
• 

  

  /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 AcresStep 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

  Tyler Bervy Stone House Properties, LLC

  2999 New York 23, Hillsdale, NY 12529
• 

  

  /34

  $640,000

  Sold Oct 15, 2025

  7 Memory Ln, Hillsdale, NY 12529

  • 2 Beds
  • 2 Baths
  • 1,010 Sq Ft
  • Built 1960

  Last Sold Summary

  • 2% Below List Price
  • $634/SF
  • 27 Days On Market

  Current Estimated Value $653,234

  Last Listing Agent John Barbato Compass, Hillsdale

  7 Memory Ln, Hillsdale, NY 12529
• 

  

  /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

  Last Listing Agent John Avenia Columbia County RE Specialist
• 

  

  /35

  $624,000

  $95K 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
• 

  $1,037,500

  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 $1,061,740

  Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

  9715 State Route 22, Hillsdale, NY 12529
• 

  Est $1,576,334

  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

  Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl
• 

  

  /66

  $290,000

  • Land
  • 40.25 Acres
  • $7,205 per Acre

  00WTP Anthony St, Hillsdale, NY 12529

  Located within the Town of Hillsdale itself, this unique 40.25± acre offering presents a rare opportunity to own a sizable tract of land in one of Columbia County's most desirable communities. While the property enjoys immediate access to the restaurants, shops, services, and amenities that make Hillsdale such a sought-after destination, its layout and surrounding landscape create a surprisingly

  Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  00WTP Anthony St, Hillsdale, NY 12529

Showing Results 121 - 160, Page 4 of 18