Hillsdale, NY Homes

/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 Acres Step 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 setting for

Tyler Bervy Stone House Properties, LLC

2999 New York 23, 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 $1,262,189

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

120 Pumpkin Hollow Rd N, 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

/34
$649,000

$70K 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
/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

/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

/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
/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

/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
- 45 Days On Market
Last Listing Agent Jessie Bennett WILLIAM PITT SOTHEBY'S - GT BARRINGTON

/25
$890,000

$105K PRICE DROP
- 2 Beds
- 2 Baths
- 2,060 Sq Ft
17 Memory Ln, Hillsdale, NY 12529

Lakefront living in one of the most peaceful and serene locations on Copake Lake. An expansive 75 feet of private waterfront with an existing dock, this charming home offers beautiful eastern views across the lake, where sunrises and tranquil water vistas become part of everyday life.The home's inviting open-concept layout has a spacious kitchen, dining, and living area. A first-floor primary

John Barbato Compass, Hillsdale

17 Memory Ln, 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

/2
Not Listed For Sale

0 Justice Rd, Hillsdale, NY 12529
0 Justice Rd, Hillsdale, NY 12529

/26
$1,100,000

$175K PRICE DROP
- 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. Plans are available for a one or two bedroom

Pamela King-Belfor Four Seasons Sotheby's Int.

401 Collins St Unit Stop 11, 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

/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

/54
$1,100,000
- 3 Beds
- 4 Baths
- 2,880 Sq Ft
2666 New York 23, Hillsdale, NY 12529

Unique investment opportunity in the hamlet of Hillsdale. This new-to-the-market commercial/residential property has been meticulously renovated by the current owner, a commercial builder, who over-engineered the project with high-end features throughout. The property consists of four distinct rental units:2666 Route 23, Main (Blue) Building- First-Floor Commercial Unit Right Side: 360

Margaret Bower Avenia Columbia County RE Specialist

2666 New York 23, 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

/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.

/55
$1,525,000
- 4 Beds
- 4.5 Baths
- 3,666 Sq Ft
83 Schmeichel Rd, Hillsdale, NY 12529

Custom contemporary home built in 1996 with thoughtful gathering spaces. Main floor has a vaulted ceiling living room with fireplace, open to dining and the eat-in-kitchen. Down a hall to the south end there is the primary suite, a powder room, laundry, the den with a vaulted ceiling and a woodstove and access to the garage. On the north side of the main living room is a large entry foyer, a

Jennifer Harvey Compass Greater NY LLC

83 Schmeichel 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 $852,632

Last Listing Agent John Avenia Columbia County RE Specialist

110 Meadow 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

/30
$1,195,000

$805K PRICE DROP
- 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
/39
$608,000

Sold Aug 12, 2026

51 Sabeff Rd, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 1,753 Sq Ft
- Built 1939
Last Sold Summary
- 6% Below List Price
- $347/SF
- 51 Days On Market
Current Estimated Value $649,748

Last Listing Agent John Avenia Columbia County RE Specialist

51 Sabeff Rd, 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

/13
$1,080,000

$5K PRICE INCREASE
- 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

/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 Listing Agent Scott Varley KW Platform

/28
$4,750,000

$2M PRICE DROP
- 6 Beds
- 6 Baths
- 6,309 Sq Ft
890 Bald Mountain Rd, Austerlitz, NY 12017

Located in a private gated community of large acreage land holders, this exquisite enclave of 3 homes, on 84 acres, hasbeen listed in Interior Design magazine. The main house is a stunning post and beam contemporary home, combining steel, glass, wood and stone panels. It overlooks the gunite pool, surrounded by stone walls and the two additional designed and inviting cottages. Continuing past

Janet Kain The Kinderhook Group, Inc.

890 Bald Mountain Rd, Austerlitz, NY 12017
$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

/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
- 27 Days On Market
Last Listing Agent John Barbato Compass, Hillsdale

/28
$499,900
- 2 Beds
- 2 Baths
- 1,362 Sq Ft
9165 New York 22, Copake, NY 12516

This one has character. Real bones, real charm, the kind of property you can't fake. Wood construction, green metal roof, mature pines creating actual privacy on your own acre.2020 renovation means the systems work: all-electric, mini splits, two bath. Two bedrooms, a potential third first floor primary or office set up, with a very flexible layout.First-time buyer who wants

Daniel Mahar Mahar Real Estate, LLC

9165 New York 22, Copake, NY 12516
/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

/33
Est $4,140,782

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
- 36 Days On Market
Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

/20
$1,695,000

Pending
- Land
- 127 Acres
- $13,346 per Acre
0 Mitchell St Unit 249980, 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 249980, 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 $656,810

Last Listing Agent Arlena Armstrong Anatole House LLC

47 Cherokee Dr, 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 Listing Agent Michael Tellerday Houlihan Lawrence, Inc.

/17
$399,000

$150K PRICE DROP Under Contract
- Land
- 83.22 Acres
- $4,795 per Acre
50 - 61 Dugway Rd, Hillsdale, NY 12529

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 that in total offer is over 33,000 feet of frontage ensuring

Jeffrey McKinney Beach & Bartolo Realtors

50 - 61 Dugway 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 $2,501,540

Last Listing Agent John Barbato Compass, Hillsdale

250 Island Dr, Craryville, NY 12521

/17
Est $422,748

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
- 62 Days On Market
Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

/44
$1,250,000

Open Sat 12:30PM - 2PM $45K PRICE DROP
- 4 Beds
- 3 Baths
- 2,395 Sq Ft
9960 New York 22, Hillsdale, NY 12529

Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat.The grand

Pamela King-Belfor Four Seasons Sotheby's Int.

9960 New York 22, Hillsdale, NY 12529

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