Hillsdale, NY Homes

/2
Est $815,443

Not Listed For Sale

137 Whippoorwill Rd, Hillsdale, NY 12529
- 4 Beds
- 3 Baths
- 2,322 Sq Ft
- Built 1910
137 Whippoorwill Rd, Hillsdale, NY 12529

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/58
$625,000

Pending
- 2 Beds
- 2.5 Baths
- 2,060 Sq Ft
534 Collins St, Hillsdale, NY 12529

Nestled on 18+ secluded acres along one of Hillsdale's most bucolic and sought-after roads, this solidly built country home offers endless potential. Located just minutes from the Massachusetts border on the edge of the Berkshires and only 15 minutes from Great Barrington, this property provides the perfect balance of peaceful rural living and convenient access to the region's renowned cultural,

John Barbato Compass, Hillsdale

534 Collins St, Hillsdale, NY 12529
$515,000

Sold Jun 16, 2026

180 Collins St, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 1,232 Sq Ft
- Built 1906
Last Sold Summary
- 14% Above List Price
- $418/SF
- 9 Days On Market
Current Estimated Value $465,474

Last Listing Agent Joseph Shirk The Kinderhook Group, Inc.

180 Collins St, Hillsdale, NY 12529

/25
Est $749,340

Not Listed For Sale

274 Texas Hill Rd, Hillsdale, NY 12529
- 3 Beds
- 2.5 Baths
- 2,272 Sq Ft
- Built 2002
274 Texas Hill Rd, Hillsdale, NY 12529

Last Sold Summary
- 41 Days On Market

/24
$575,000

$40K PRICE DROP
- 3 Beds
- 1.5 Baths
- 864 Sq Ft
5 Adams Dr, Hillsdale, NY 12529

This charming 3 BR, 1.5 Bath cottage is located across the street from Copake Lake and the HOA Waterfront, Marina and Beach area. Unlike some of the other homes in the area, the house is situated on an elevated, oversized lot with a big front yard and spectacular sunset views. Inside, the house features real wood paneling and a wood burning stove in the living room, a cozy kitchen with a new gas

Russ Stein Compass Greater NY LLC

5 Adams Dr, Hillsdale, NY 12529
/18
$335,000

Sold Jul 24, 2025

118 Yonderview Rd, Hillsdale, NY 12529
- 3 Beds
- 1.5 Baths
- 1,536 Sq Ft
- Built 1963
Last Sold Summary
- 4% Below List Price
- $218/SF
- 58 Days On Market
Current Estimated Value $374,102

Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

118 Yonderview Rd, Hillsdale, NY 12529

Est $755,136

Not Listed For Sale

62 Bucky Rd, Hillsdale, NY 12529
- 4 Beds
- 3 Baths
- 3,034 Sq Ft
- Built 1960
62 Bucky Rd, Hillsdale, NY 12529

Last Sold Summary
- 110 Days On Market

/44
$1,485,000
- 3 Beds
- 2.5 Baths
- 2,100 Sq Ft
51 Taconic Creek Rd, Hillsdale, NY 12529

This perfect modern farmhouse retreat is tucked away on one of Columbia County's most quiet and beautiful roads guaranteeing a tranquil respite from the city. Being one of just a handful of properties on the road creates a sense of peace and quiet that is unmatched. While a feeling of simplicity emanates throughout the land there is a clear level of sophistication in the design details. The

Thomas Pawlowski Four Seasons Sotheby's Int.

51 Taconic Creek Rd, Hillsdale, NY 12529
/26
$510,000

Sold Dec 15, 2025

25 Catamount Rd, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 820 Sq Ft
- Built 2024
Last Sold Summary
- 7% Below List Price
- $622/SF
- 33 Days On Market
Last Listing Agent Paige Backhaus William Raveis Real Estate

25 Catamount Rd, Hillsdale, NY 12529

/25
Est $557,786

Not Listed For Sale

15 Henich Ln, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 1,650 Sq Ft
- Built 1990
15 Henich Ln, Hillsdale, NY 12529

Last Sold Summary
- 46 Days On Market

/41
$2,195,000
- 3 Beds
- 3 Baths
- 2,755 Sq Ft
292 White Hill Rd, Hillsdale, NY 12529

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

292 White Hill Rd, Hillsdale, NY 12529
/28
$450,000

Sold Jun 18, 2026

364 Yonderview Rd, Hillsdale, NY 12529
- 4 Beds
- 5 Baths
- 3,425 Sq Ft
- Built 1850
Last Sold Summary
- 16% Below List Price
- $131/SF
- 7 Days On Market
Current Estimated Value $660,996

Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

364 Yonderview Rd, Hillsdale, NY 12529

/37
Est $594,912

Not Listed For Sale

68 Cherokee Dr, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 1,685 Sq Ft
- Built 1994
68 Cherokee Dr, Hillsdale, NY 12529

Last Sold Summary
- 61 Days On Market

/23
$305,000

$15K PRICE INCREASE
- 2 Beds
- 1 Bath
- 925 Sq Ft
9377 State Route 22, Hillsdale, NY 12529

BACK ON MARKET!! Welcome home to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard

Scott Zobre KW MidHudson

9377 State Route 22, Hillsdale, NY 12529
/14
$255,000

Sold Feb 13, 2026

49 Stonehill Dr, Hillsdale, NY 12529
- 1 Bed
- 1 Bath
- 525 Sq Ft
- Built 1963
Last Sold Summary
- 9% Above List Price
- $486/SF
- 78 Days On Market
Current Estimated Value $259,286

Last Listing Agent Sarah Lipsky William Pitt Sothebys Intn'l

49 Stonehill Dr, Hillsdale, NY 12529

Est $1,418,773

Not Listed For Sale

656 Breezy Hill Rd, Hillsdale, NY 12529
- 4 Beds
- 3.5 Baths
- 2,272 Sq Ft
- Built 1850
656 Breezy Hill Rd, Hillsdale, NY 12529

Last Sold Summary
- 57 Days On Market

/26
$1,150,000

$125K PRICE DROP
- 1 Bed
- 2 Baths
- 1,700 Sq Ft
401 Collins St, 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 Sothebys Intl

401 Collins St, Hillsdale, NY 12529
/26
$1,037,500

Sold Apr 28, 2026

9715 New York 22, Hillsdale, NY 12529
- 5 Beds
- 2.5 Baths
- 3,350 Sq Ft
- Built 1788
Last Sold Summary
- 6% Below List Price
- $310/SF
- 160 Days On Market
Last Listing Agent Annabel Taylor Four Seasons Sotheby's Int.

9715 New York 22, Hillsdale, NY 12529

/28
Est $389,721

Not Listed For Sale

119 Black Grocery Rd, Hillsdale, NY 12529
- 3 Beds
- 1 Bath
- 1,232 Sq Ft
- Built 1971
119 Black Grocery Rd, Hillsdale, NY 12529

Last Sold Summary
- 211 Days On Market

/32
$619,000

$30K PRICE DROP
- 2 Beds
- 1.5 Baths
- 1,500 Sq Ft
416 Whippoorwill Rd, Hillsdale, NY 12529

This one checks all of the boxes. Our newly listed two bedroom, two bath Cape Cod style home in Hillsdale has been 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

Margaret Bower Avenia Columbia County RE Specialist

416 Whippoorwill Rd, Hillsdale, NY 12529
/68
$3,700,000

Sold Aug 18, 2025

149 Tory Hill Farm Rd, Hillsdale, NY 12529
- 4 Beds
- 2.5 Baths
- 3,604 Sq Ft
- Built 1986
Last Sold Summary
- 1% Above List Price
- $1,027/SF
- 39 Days On Market
Current Estimated Value $3,261,137

Last Listing Agent John Barbato Compass, Hillsdale

149 Tory Hill Farm Rd, Hillsdale, NY 12529

/14
Est $480,135

Not Listed For Sale

52 Connelly Rd, Hillsdale, NY 12529
- 4 Beds
- 2 Baths
- 2,343 Sq Ft
- Built 1952
52 Connelly Rd, Hillsdale, NY 12529

Last Sold Summary
- 142 Days On Market

/5
$259,000
- Land
- 15.47 Acres
- $16,742 per Acre
191 Berkshire Rd, Hillsdale, NY 12529

Discover the perfect opportunity to build your dream home on this expansive 15.47-acre parcel at 191 Berkshire Road, bordering Copake Country Club and just minutes from Copake Lake. This fully undeveloped property is part of the desirable Sam Hill Road community, offering shared waterfront access through the HOA. Ideally located just 25 minutes from Hudson and Great Barrington, MA, you'll enjoy

Austin Urban Venture Fox Realty Group

191 Berkshire Rd, Hillsdale, NY 12529
/4
$150,000

Sold Jan 29, 2026

0 Knapp Hollow Ln, Hillsdale, NY 12529
- Land
- 6.25 Acres
- $24,000 per Acre
Last Sold Summary
- 12% Below List Price
- 39 Days On Market
Last Listing Agent marylou Kersten Copake Lake Realty Corp.

0 Knapp Hollow Ln, Hillsdale, NY 12529

/27
Est $890,439

Not Listed For Sale

66 Fado Rd, Hillsdale, NY 12529
- 3 Beds
- 1.5 Baths
- 1,421 Sq Ft
- Built 1850
66 Fado Rd, Hillsdale, NY 12529

Last Sold Summary
- 368 Days On Market

/7
$257,000

$2K PRICE DROP
- 3 Beds
- 3 Baths
- 2,304 Sq Ft
9249 Route 22 Rd, Hillsdale, NY 12516

Mixed Residential/Commercial building, with 3 rentable spaces. Current RR 30,540. One side of building has commercial reception area down and 1BR apartment above. Rental 1395/m. Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is 795 + 550. Ideal for live/work. Building in excellent condition, roof less than 5 years old.

David Birch Barns & Farms Realty, LLC

9249 Route 22 Rd, Hillsdale, NY 12516
/36
$580,000

Sold Jun 12, 2026

2657 State Route 23, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,057 Sq Ft
- Built 1780
Last Sold Summary
- 11% Below List Price
- $282/SF
- 244 Days On Market
Current Estimated Value $573,817

Last Listing Agent John Barbato Compass, Hillsdale

2657 State Route 23, Hillsdale, NY 12529

/114
Est $3,185,926

Not Listed For Sale

184A Cambridge Rd, Hillsdale, NY 12529
- 5 Beds
- 4.5 Baths
- 4,130 Sq Ft
- Built 2021
184A Cambridge Rd, Hillsdale, NY 12529

Last Sold Summary
- 35 Days On Market

/51
$729,900
- 3 Beds
- 2.5 Baths
- 2,210 Sq Ft
417 Overlook Dr, Hillsdale, NY 12529

Discover Your Dream Cape-Style Home: A Serene Escape on 2.1 Acres Nestled in a tranquil setting, this stunning Cape-style home offers the perfect blend of comfort and luxury, with 2.1 acres of nature at your doorstep. Imagine sipping your morning coffee on the spacious front porch while listening to the gentle rustle of leaves around you. Step inside to an inviting and dramatic living room, where

Barbara Robinson Red Apple Realty

417 Overlook Dr, Hillsdale, NY 12529
/39
$912,500

Sold Nov 07, 2025

11 Cold Water St, Hillsdale, NY 12529
- 5 Beds
- 3.5 Baths
- 2,834 Sq Ft
- Built 1848
Last Sold Summary
- 2% Above List Price
- $322/SF
- 29 Days On Market
Last Listing Agent MATTHEW CAREY Rouse + Co Real Estate

11 Cold Water St, Hillsdale, NY 12529

/20
Est $241,498

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

/7
$95,000
- Land
- 12.95 Acres
- $7,336 per Acre
00 Stone Ledge Rd, Hillsdale, NY 12529

Quiet location next to the Berkshires. Dead end road with a 12 acre parcel. Hiking trails throughout. Glorious views off the top. Great value. More land available.

Tracy Tassinari Gabel Real Estate

00 Stone Ledge Rd, Hillsdale, NY 12529
$1,100,000

Sold Aug 18, 2025

515 Turnpike, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,134 Sq Ft
- Built 1983
Last Sold Summary
- 8% Below List Price
- $515/SF
- 50 Days On Market
Last Listing Agent Joseph Briggs William Pitt Sothebys Int Rlty

515 Turnpike, Hillsdale, NY 12529

/13
Est $378,325

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

/13
$595,000
- Land
- 30 Acres
- $19,833 per Acre
0 Labranch Unit 20252234, Hillsdale, NY 12529

Wonderful southern exposure on one of the most scenic byways in Columbia County. Large parcels and restrictive covenants on abutting land. High fields and ancient tree lines dotted with maples and old stone walls. Nice mix of open and wooded to tuck your home into the hedge row without another home in site. Distant views of Catamount Mountain. Close to Hawthorne Valley School and the Berkshires.

Tracy Tassinari Gabel Real Estate

0 Labranch Unit 20252234, Hillsdale, NY 12529
$1,150,000

Sold Nov 17, 2025

306 County Route 21c, Ghent, NY 12075
- 4 Beds
- 3 Baths
- 2,500 Sq Ft
- Built 1890
Last Sold Summary
- 8% Below List Price
- $460/SF
- 48 Days On Market
Current Estimated Value $1,092,578

Last Listing Agent Nancy Felcetto Brown Harris Stevens HV LLC

306 County Route 21c, Ghent, NY 12075

/44
Est $1,307,876

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

/21
$346,900

$53K PRICE DROP
- 3 Beds
- 1 Bath
- 1,381 Sq Ft
9659 New York 22, Hillsdale, NY 12529

Come see the new me!. I've had a face lift and you are sure to enjoy the gleaming hardwood floors and the updated kitchen with granite counters and new appliances. It's one level of easy living, and offers many wonderful features. Enjoy the spacious living room framed by a fireplace, or the cozy den which has one as well..The middle bedroom features sliders that open onto a deck, great to enjoy

Tammy Molinski Coldwell Banker Advisor Realty

9659 New York 22, 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

/20
Est $345,274

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

Showing Results 41 - 80, Page 2 of 18

New York Columbia County Hillsdale

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