Hillsdale, NY Homes

/20
Not Listed For Sale
0 W End Rd, Hillsdale, NY 12529

0 W End Rd, Hillsdale, NY 12529

/19
$347,000
- 2 Beds
- 1 Bath
- 736 Sq Ft
81 SW 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!

Margaret Bower Avenia Columbia County RE Specialist

81 SW Sw Colony 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

/26
Not Listed For Sale
- 29 Beds
- 28 Baths
- 3,000 Sq Ft
2871 New York 23, Hillsdale, NY 12529

2871 New York 23, Hillsdale, NY 12529

/22
$985,000 Pending
- 2 Beds
- 2 Baths
- 1,419 Sq Ft
75 Upper Hollow Rd, Hillsdale, NY 12529

Nestled along a picturesque, secluded country dirt road--surrounded by a serene pond, a flowing creek, and wooded acreage--this charming 2 bedroom log cabin offers the perfect escape. The expansive property spans 193 acres, with 18 acres located outside the Columbia Land Conservancy and Forestry Program, allowing for reduced taxes and enhanced privacy. Recently renovated with a stylish bathroom

Janet Kain The Kinderhook Group, Inc.

75 Upper Hollow 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

/17
Est $388,940 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,111 Sq Ft
2951 State Route 23, Hillsdale, NY 12529

2951 State Route 23, Hillsdale, NY 12529

/15
$999,000 Pending
- 4 Beds
- 2.5 Baths
- 1,344 Sq Ft
25 Nobletown Rd, Hillsdale, NY 12529

Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim

Andrew Gates Houlihan Lawrence

25 Nobletown Rd, Hillsdale, NY 12529
/26
Sold Jan 16, 2025

73 Mitchell St, Hillsdale, NY 12529
- 4 Beds
- 3.5 Baths
- 3,537 Sq Ft
Last Sold Summary
- 153 Days On Market
Last Listing Agent LILLIAN LIN Rouse + Co Real Estate, LLC

73 Mitchell St, Hillsdale, NY 12529

/2
Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,024 Sq Ft
361 Craryville Rd, Hillsdale, NY 12529

361 Craryville Rd, Hillsdale, NY 12529

/49
$2,995,000
- 4 Beds
- 3 Baths
- 2,825 Sq Ft
88 Mac Brown Rd, Claverack-Red Mills, NY 12513

Welcome to Mac Brown Waterhouse, a storied 119-acre estate set within a hidden valley offering complete seclusion and timeless beauty. The original 1830s farmhouse is tucked away at the end of a private lane in Claverack, NY, where the road terminates in a round gravel driveway anchored by the property’s original stone well. Two large ponds grace the land, one directly in front of the house that

Anthony D'Argenzio Houlihan Lawrence, Inc

88 Mac Brown Rd, Claverack-Red Mills, NY 12513
/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
Last Listing Agent Arlena Armstrong Anatole House LLC

47 Cherokee Dr, Hillsdale, NY 12529

/26
Est $334,396 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
431 SW Colony Rd, Hillsdale, NY 12529

431 SW Colony Rd, Hillsdale, NY 12529

/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
/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
Last Listing Agent John Barbato Compass, Hillsdale

250 Island Dr, Craryville, NY 12521

/25
Est $925,726 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,126 Sq Ft
184 Overlook Dr, Hillsdale, NY 12529

184 Overlook Dr, Hillsdale, NY 12529

/26
$1,100,000
- 5 Beds
- 2.5 Baths
- 3,350 Sq Ft
9715 State Route 22, Hillsdale, NY 12529

Said to be Hillsdale's second oldest home, this historic c1788 Shaker built center chimney Colonial sits on 17 acres of sprawling green hillside, gardens, and fruit trees. Once the home of Captain John Collin III, the home sits along the beautiful corridor connecting the Hudson Valley and the Berkshires— an area characterized by its rolling hillsides and rural landscape. Meticulously restored,

Annabel Taylor Four Seasons Sothebys Intl

9715 State Route 22, Hillsdale, NY 12529
/19
$191,000 Sold Feb 12, 2025

22 Anthony St, Hillsdale, NY 12529
- 5 Beds
- 5 Baths
- 2,502 Sq Ft
- Built 1888
Last Sold Summary
- 20% Above List Price
- $76/SF
- 83 Days On Market
Current Estimated Value $202,705

Last Listing Agent Margaret Bower Avenia Columbia County RE Specialist

22 Anthony St, Hillsdale, NY 12529

/36
Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,384 Sq Ft
208 Cambridge Rd, Hillsdale, NY 12529

208 Cambridge Rd, Hillsdale, NY 12529

/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

/23
Est $783,361 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,310 Sq Ft
161 White Hill Rd, Hillsdale, NY 12529

161 White Hill Rd, Hillsdale, NY 12529

/47
$895,000
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
110 Meadow Ln, Hillsdale, NY 12529

If your checklist for a new home includes any of the following, your search may have reached a successful conclusion. Let us introduce you to 110 Meadow Lane in Hillsdale NY. Views - Totally unique forever views that will inspire for a lifetimeLocation - Near the NY and MA border offering easy access to both Columbia County and the BerkshiresSingle-Story Living - A

John Avenia Columbia County RE Specialist

110 Meadow Ln, Hillsdale, NY 12529

/3
Not Listed For Sale
0 Connelly - Off Unit 137624, Copake, NY 12517

0 Connelly - Off Unit 137624, Copake, NY 12517

/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

/4
Not Listed For Sale
0 Mitchell St Unit 131897, Hillsdale, NY 12529

0 Mitchell St Unit 131897, Hillsdale, NY 12529

/20
$598,000
- Land
- 12.6 Acres
- $47,460 per Acre
67 Taconic Creek Rd, Hillsdale, NY 12529

Set down a secluded 1/8-mile driveway, this 12.6-acre property in the tranquil countryside of Hillsdale offers unmatched privacy and sweeping valley and mountain views. This beautiful home site includes plans for a stunning, modern-country 4,200sq ft main house and a separate 1,700sq ft 3 car garage with studio. Ready to build your dream home, this site provides an ideal canvas for creating your

Peter Yates Four Seasons Sotheby's Int.

67 Taconic Creek Rd, Hillsdale, NY 12529

/8
Not Listed For Sale
0 Mitchell St Unit 131892, Hillsdale, NY 12529

0 Mitchell St Unit 131892, Hillsdale, NY 12529

/9
Not Listed For Sale
- 4 Beds
Unlisted Address

Unlisted Address

/2
Est $831,525 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,500 Sq Ft
14 Holm Rd, Hillsdale, NY 12529

14 Holm Rd, Hillsdale, NY 12529

/2
Est $341,662 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
100 Lockwood Rd, Craryville, NY 12521

100 Lockwood Rd, Craryville, NY 12521

/30
Est $858,254 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
212 Pumpkin Hollow Rd N, Hillsdale, NY 12529

212 Pumpkin Hollow Rd N, Hillsdale, NY 12529

/28
Est $450,901 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,300 Sq Ft
14 Mansfield Rd, Hillsdale, NY 12529

14 Mansfield Rd, Hillsdale, NY 12529

/54
Est $641,836 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,782 Sq Ft
1650 County Route 11, Craryville, NY 12521

1650 County Route 11, Craryville, NY 12521

Est $1,574,575 Not Listed For Sale
- 5 Beds
- 4 Baths
- 5,000 Sq Ft
51 Marsh Hawk Rd, Craryville, NY 12521

51 Marsh Hawk Rd, Craryville, NY 12521

/37
Est $862,169 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,234 Sq Ft
111 Hunt Rd, Hillsdale, NY 12529

111 Hunt Rd, Hillsdale, NY 12529

/10
Est $679,722 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,928 Sq Ft
1000 Mitchell St, Hillsdale, NY 12529

1000 Mitchell St, Hillsdale, NY 12529

/10
Est $676,434 Not Listed For Sale
- 3 Beds
86 Stagecoach Rd, Hillsdale, NY 12529

86 Stagecoach Rd, Hillsdale, NY 12529

/15
Est $352,729 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
234 Harder Rd, Hillsdale, NY 12529

234 Harder Rd, Hillsdale, NY 12529

/35
Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,596 Sq Ft
2 Julianna Dr Unit Main, Copake, NY 12516

2 Julianna Dr Unit Main, Copake, NY 12516

/10
Not Listed For Sale
- 2 Beds
- 2 Baths
- 2,479 Sq Ft
84 Connelly Rd, Copake, NY 12516

84 Connelly Rd, Copake, NY 12516

Showing Results 121 - 160, Page 4 of 18

New York Columbia County Hillsdale

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