Homes in ZIP Code 12529

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  /34

  $589,900 Pending

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

  66 Anthony St, Hillsdale, NY 12529

  This home on almost 4 acres with a private pond and scenic mountain and sunset views year-round, also abuts the Harlem Valley Rail Trail. It is withinwalking distance to the village of Hillsdale. Including the Roe Jan Brewing Co. IGA, the Hillsdale House, and the town park. Less then 5-min driveto Catamount; 25 min to Hudson NY, and 20 min to Great Barrington MA.

  Susan Calkins STONE HOUSE PROPERTIES, LLC

  66 Anthony St, 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 $1,104,836

  Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

  9715 State Route 22, Hillsdale, NY 12529
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  /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

  • $203/SF
  • 35 Days On Market

  • Last Sold Price $385,000
  • Sep 29, 2023

  Last Listing Agent Karen Davala Davala Real Estate
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  /23

  $495,000 New Construction

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

  217 Anthony St, Hillsdale, NY 12529

  A newly built home ideally located on the edge of the charming hamlet of Hillsdale, NY, this home offers the convenience of true walkability--just steps to everyday essentials including the local hardware store, grocery market, wine shop, post office, town hall, coffee shops, restaurants, and boutique shops. With 3-bedrooms and 2-bathrooms, the home spans approximately 1,350 square feet of modern

  John Barbato Compass, Hillsdale

  217 Anthony St, Hillsdale, NY 12529
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  /35

  $410,000 Sold Aug 15, 2025

  51 Taconic Creek Rd, Hillsdale, NY 12529

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1993

  Last Sold Summary

  • 12% Below List Price
  • $214/SF
  • 24 Days On Market

  Current Estimated Value $453,667

  Last Listing Agent Kate Lascar COMPASS MASSACHUSETTS , LLC GB

  51 Taconic Creek Rd, Hillsdale, NY 12529
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  /37

  Not Listed For Sale

  9361 Ny-22 --, Hillsdale, NY 12529

  • 4 Beds
  • 2.5 Baths
  • 2,681 Sq Ft
  • Built 1830

  9361 Ny-22 --, Hillsdale, NY 12529

  Last Sold Summary

  • $263/SF
  • 45 Days On Market

  • Last Sold Price $705,000
  • Aug 04, 2023

  Last Listing Agent Jessie Bennett William Pitt
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  /18

  $2,999,000

  • Land
  • 242 Acres
  • $12,393 per Acre

  2 Dugway Rd, Austerlitz, NY 12017

  242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

  Michael Tellerday Houlihan Lawrence, Inc.

  2 Dugway Rd, Austerlitz, NY 12017
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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 $915,846

  Last Listing Agent John Avenia Columbia County RE Specialist

  110 Meadow Ln, Hillsdale, NY 12529
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  /2

  Not Listed For Sale

  0 Justice Rd, Hillsdale, NY 12529

  0 Justice Rd, Hillsdale, NY 12529

  Last Sold Summary

  • Last Sold Price $73,000

  Last Listing Agent Kelsey Winters Davala Real Estate, LLC
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  /25

  $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

  $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
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  /45

  Not Listed For Sale

  228 County Route 21 --, Hillsdale, NY 12529

  • 6 Beds
  • 3 Baths
  • 3,028 Sq Ft
  • Built 1942

  228 County Route 21 --, Hillsdale, NY 12529

  Last Sold Summary

  • $182/SF
  • 13 Days On Market

  • Last Sold Price $550,000
  • Apr 28, 2023

  Last Listing Agent Michael Castellano GILCREST PROPERTIES
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  /11

  $319,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  15 Melvin Rd, Craryville, NY 12521

  Move right into this 1960 Copake Lake cottage with deeded lake rights! On a quiet road just a five minute walk to the lake is your quaint oasis lovingly restored in 2023. Upgrades include a new open concept kitchen, living and dining area. Bathroom completely remodeled with walk-in shower. Upgraded mechanicals include furnace, oil tank, hot water heater, well pump and plumbing. The backyard

  John Peterson THE TRUSS GROUP LLC

  15 Melvin Rd, Craryville, NY 12521
• 

  $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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  /20

  Est $454,795 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

  • 7% Above List Price
  • $284/SF
  • 73 Days On Market

  • Last Sold Price $425,000
  • May 07, 2024

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.
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  /44

  $1,250,000

  • 5 Beds
  • 3 Baths
  • 2,548 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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  /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
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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

  • Last Sold Price $12,800
  • Sep 25, 2023

  Last Listing Agent John Avenia Columbia County RE Specialist
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  /28

  $1,275,000 Open Sun 12:30PM - 2PM

  • 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. Expansive pivoting picture windows invite a

  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 $623,807

  Last Listing Agent Arlena Armstrong Anatole House LLC

  47 Cherokee Dr, Hillsdale, NY 12529
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  Est $1,483,688 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

  • 14% Above List Price
  • $495/SF
  • 9 Days On Market

  • Last Sold Price $1,300,000
  • May 23, 2024

  Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl
• 

  

  /19

  $225,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 794 Sq Ft

  2227 County Route 21, Hillsdale, NY 12529

  Tucked away on over 17 serene, subdividable acres in the Town of Kinderhook, this rare offering includes a half-finished 2-bedroom home (a shell awaiting your vision) with a brand-new raised-bed septic system and drilled well (newer pump) & new pressure tank already in place. With frontage on two quiet country roads; County Route 21 and Fowler Lake Rd. this land is a mix of old stone walls,

  Michael Castellano Gilcrest Properties

  2227 County Route 21, Hillsdale, NY 12529
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  /2

  Est $2,602,321 Not Listed For Sale

  431 Lakeview Rd, Craryville, NY 12521

  • 7 Beds
  • 4.5 Baths
  • 2,947 Sq Ft
  • Built 1920

  431 Lakeview Rd, Craryville, NY 12521

  Last Sold Summary

  • 4% Below List Price
  • $916/SF
  • 83 Days On Market

  • Last Sold Price $2,700,000
  • Aug 28, 2023

  Last Listing Agent MATTHEW CAREY Rouse + Co Real Estate
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  /21

  $1,650,000

  • 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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  /3

  Not Listed For Sale

  10695 Ny-22, Hillsdale, NY 12529

  10695 Ny-22, Hillsdale, NY 12529

  Last Sold Summary

  • 39 Days On Market

  • Last Sold Price $137,000
  • Oct 24, 2023

  Last Listing Agent Scott Varley KW Platform
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  /13

  $1,080,000

  • 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
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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

  • $450/SF
  • 27 Days On Market

  • Last Sold Price $675,000
  • Sep 06, 2024

  Last Listing Agent John Barbato Compass, Hillsdale
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  /69

  $2,995,000

  • 4 Beds
  • 3 Baths
  • 3,641 Sq Ft

  88 Mac Brown Rd, Claverack-Red Mills, NY 12513

  Welcome to Wolverton Creative Compound, a 119-acre estate in Claverack, NY, offering total privacy, wide southern light, integrated live-work studios, and a large swimmable pond with pebble beach. The 1830s farmhouse features four bedrooms, two baths, original moldings and Dutch doors, a whole-house water filter, and a bright layout for indoor-outdoor living. A fully insulated studio barn is

  Anthony D'Argenzio Houlihan Lawrence

  88 Mac Brown Rd, Claverack-Red Mills, NY 12513
• 

  

  /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

  • Last Sold Price $110,000
  • Jun 25, 2024

  Last Listing Agent Michael Tellerday Houlihan Lawrence, Inc.
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  /17

  $425,000

  • Land
  • 83.22 Acres
  • $5,107 per Acre

  50 - 61 Dugway Rd, Hillsdale, NY 12529

  Two Large Parcels Combine Offering Serenity & Great Potential. 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

  Jeffrey McKinney Beach & Bartolo Realtors

  50 - 61 Dugway Rd, Hillsdale, NY 12529
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  /15

  Est $251,468 Not Listed For Sale

  38 Robin Rd, Craryville, NY 12521

  • 2 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1945

  38 Robin Rd, Craryville, NY 12521

  Last Sold Summary

  • 5% Above List Price
  • $278/SF
  • 96 Days On Market

  • Last Sold Price $240,000
  • Apr 09, 2025

  Last Listing Agent Dennis Wheeler, CBR, AHWD,SRES Berkshire Hathaway HomeService
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  /50

  $1,695,000 Pending

  • 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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  /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

  • $367/SF

  • Last Sold Price $1,100,000
  • Jun 27, 2023

  Last Listing Agent Natalia de Amorim Preferred Country Properties
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  /19

  $325,000

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft

  81 SW Colony Rd, Hillsdale, NY 12529

  Welcome to Copake Lake!! Sweet two-bedroom, one bath cottage, eat in kitchen, views of the lake from living room and one of the two bedrooms, nice big yard to enjoy outdoor fun. All appliances included. PLUS (As per Seller) water rights along that 20-foot stretch, a buyer may be able to agree with others in the area to extend the existing dock, which could be up to 60 feet into the lake! Property

  Margaret Bower Avenia Columbia County RE Specialist

  81 SW Colony Rd, Hillsdale, NY 12529
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  /17

  Est $371,862 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

  • 5% Above List Price
  • $320/SF
  • 62 Days On Market

  • Last Sold Price $355,000
  • Aug 30, 2024

  Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.
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  /8

  $375,000

  • Land
  • 90 Acres
  • $4,167 per Acre

  0 Harlemville Rd Unit 20254229, Hillsdale, NY 12529

  On a bucolic country by-way you will find this very private wooded hilltop parcel with Catskill Mountain views. Gorgeous mature timber and beautiful rocky outcrops dot this parcel. Access is via a brief right-of-way and along a pretty private lane. Note reduced taxes due to a power line easement to the rear of the property. Suitable for a single main residence.

  James Male HOUSE Hudson Valley Realty

  0 Harlemville Rd Unit 20254229, Hillsdale, NY 12529
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  /11

  Est $762,805 Not Listed For Sale

  7 Birch Hill Rd, Craryville, NY 12521

  • 3 Beds
  • 2.5 Baths
  • 2,296 Sq Ft
  • Built 2003

  7 Birch Hill Rd, Craryville, NY 12521

  Last Sold Summary

  • 112% Above List Price
  • $157/SF
  • 15 Days On Market

  • Last Sold Price $360,000
  • Dec 29, 2023

  Last Listing Agent Dennis Wheeler, CBR, AHWD,SRES Berkshire Hathaway Home Services Blake
• 

  

  /22

  $1,695,000

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

  0 Mitchell St Unit 246335, 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 246335, Hillsdale, NY 12529
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  /3

  Not Listed For Sale

  0 Anthony St, Copake, NY 12529

  0 Anthony St, Copake, NY 12529

  Last Sold Summary

  • 33 Days On Market

  • Last Sold Price $45,000
  • Nov 20, 2023

  Last Listing Agent Karen Davala Davala Real Estate
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  /14

  $700,000

  • Land
  • 9 Acres
  • $77,778 per Acre

  162 Lk Rdg Ln, Copake Lake, NY 12521

  A special opportunity to enjoy lake living within a uniquely private setting. The Ridge at Copake Lake is a gated private road of 11 ready-to-build lots nestled in the lush landscape of an untouched mountain top. Each designated building site has been artfully tailored to visually isolate one home from another. The 9+ acres of Lot 10 embrace direct views of the Taconic mountains to the east.

  John Barbato Compass, Hillsdale

  162 Lk Rdg Ln, Copake Lake, NY 12521

Showing Results 121 - 160, Page 4 of 18