Hillsdale, NY Homes

/19
$225,000 Pending
- 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
/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

/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

/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
/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

/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.

/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
/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

/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

/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
$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

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

/17
$425,000 Under Contract
- 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
/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

/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

/45
$3,395,000 New Construction
- 4 Beds
- 4 Baths
- 3,855 Sq Ft
110 Mansfield Rd, Hillsdale, NY 12529

Welcome to a newly built modern farmhouse set on 11.7 private acres in the heart of magical Hillsdale. Arriving via a sweeping driveway, rolling, manicured lawns unfold into cultivated fields. Designed for indoor-outdoor living, this 4-bedroom, 4-bath home features a dramatic great room with floor-to-ceiling glass for uninterrupted, far-reaching views. The residence offers a rare blend of modern

Peter Yates Four Seasons Sotheby's Int.

110 Mansfield Rd, Hillsdale, NY 12529
/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 $665,496

Last Listing Agent Arlena Armstrong Anatole House LLC

47 Cherokee Dr, Hillsdale, NY 12529

/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

/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
/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 $2,182,681

Last Listing Agent John Barbato Compass, Hillsdale

250 Island Dr, Craryville, NY 12521

/33
Est $3,910,427 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
- 3% Above List Price
- $718/SF
- 36 Days On Market
- Last Sold Price $3,807,437
- Sep 20, 2024
Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

/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

/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.

/35
$395,000 Pending
- 4 Beds
- 2 Baths
- 1,660 Sq Ft
50 Lockwood Rd, Craryville, NY 12521

Anthony D'Argenzio Houlihan Lawrence, Inc

50 Lockwood Rd, Craryville, NY 12521

/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

/40
$649,000 Pending
- 3 Beds
- 2 Baths
- 1,753 Sq Ft
51 Sabeff Rd, Hillsdale, NY 12529

51 Sabeff Road is new to the market for the first time since the original owner, Sabcho Sabeff, sold it in 1981. It has been enjoyed as a family compound by the current owners since that time. Entering the property from Sabeff Road, a town maintained dead end road in the heart of Hillsdale, is like taking a step back in time. This spectacular parcel is a nice mix of flat lawn and slightly sloping

John Avenia Columbia County RE Specialist

51 Sabeff Rd, Hillsdale, NY 12529

/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.

/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

/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
- $487/SF
- 375 Days On Market
- Last Sold Price $985,000
- Oct 21, 2023
Last Listing Agent Andrew Gates Houlihan Lawrence, Inc.

/44
$6,950,000
- 5 Beds
- 4.5 Baths
- 6,438 Sq Ft
890 Bald Mountain Rd, Austerlitz, NY 12017

Welcome to Bald Mountain Estate, an extraordinary private compound spanning 85 breathtaking acres overlooking the Hudson Valley and the Berkshire Hills. This four-building, ultra-contemporary estate epitomizes modern country luxury, featuring floor-to-ceiling glass walls and a steel infrastructure that creates a distinctive blend of rusticelegance and architectural sophistication.The

Lisa Bouchard Hoe The Kinderhook Group, Inc.

890 Bald Mountain Rd, Austerlitz, NY 12017

/26
Est $304,788 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
- 6% Above List Price
- $239/SF
- 79 Days On Market
- Last Sold Price $287,000
- Jul 19, 2024
Last Listing Agent John Barbato Compass, Hillsdale

/25
Est $926,409 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
- 7% Above List Price
- $406/SF
- 73 Days On Market
- Last Sold Price $863,000
- Aug 12, 2024
Last Listing Agent Jason Loeb Four Seasons Sotheby's Int.

/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
- $389/SF
- 56 Days On Market
- Last Sold Price $927,000
- Aug 19, 2024
Last Listing Agent Gerard Meenagh The Meenagh Group Realty

/23
Est $758,800 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
- 102% Above List Price
- $286/SF
- 69 Days On Market
- Last Sold Price $375,000
- Aug 05, 2013
Last Listing Agent Victor Franco Jr Weichert Realtors Northeast Gp

/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
- Last Sold Price $90,000
- Apr 20, 2022
Last Listing Agent Jennifer Capala William Pitt Sothebys Intn'l

/4
Not Listed For Sale

0 Mitchell St Unit 131897, Hillsdale, NY 12529
0 Mitchell St Unit 131897, Hillsdale, NY 12529

Last Sold Summary
- 312 Days On Market
- Last Sold Price $1,200,000
- Apr 21, 2021
Last Listing Agent Jennifer Harvey Compass Greater NY LLC

/4
Not Listed For Sale

0 Mitchell St Unit 132496, Hillsdale, NY 12529
0 Mitchell St Unit 132496, Hillsdale, NY 12529

Last Sold Summary
- 755 Days On Market
- Last Sold Price $220,000
- Feb 03, 2023
Last Listing Agent Tracy Tassinari Past Member

/9
Not Listed For Sale

Unlisted Address
- 4 Beds
- Built 1970
Unlisted Address

Last Sold Summary
- $222/SF
- 148 Days On Market
- Last Sold Price $1,200,000
- Dec 01, 2021
Last Listing Agent Jen Harvey COMPASS MASSACHUSETTS , LLC GB

/2
Est $837,936 Not Listed For Sale

14 Holm Rd, Hillsdale, NY 12529
- 3 Beds
- 3 Baths
- 2,500 Sq Ft
- Built 2009
14 Holm Rd, Hillsdale, NY 12529

Last Sold Summary
- 47% Below List Price
- $228/SF
- Last Sold Price $570,000
Last Listing Agent marylou Kersten COPAKE LAKE REALTY CORP.

/2
Est $304,739 Not Listed For Sale

100 Lockwood Rd, Craryville, NY 12521
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
- Built 1950
100 Lockwood Rd, Craryville, NY 12521

Last Sold Summary
- 56% Above List Price
- $195/SF
- 88 Days On Market
- Last Sold Price $195,000
- Aug 19, 2021
Last Listing Agent PATRICIA HINKEIN Patricia A. Hinkein Realty

Showing Results 121 - 160, Page 4 of 18

New York Columbia County Hillsdale

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