Hillsdale, NY Homes

/39
$7,950,000
- 5 Beds
- 4.5 Baths
- 6,438 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 has been listed in Interior Design magazine. The main house is a stunning post and beam contemporary home, combining steel, stone, wood and glass panels. It overlooks the gunite pool, surrounded by stone walls and the two additional designed and inviting cottages. Continuing past the

Janet Kain The Kinderhook Group, Inc.

890 Bald Mountain Rd, Austerlitz, NY 12017
/10
$300 per month
- 4 Beds
- 3 Baths
- 2,349 Sq Ft
- House for Rent
125 Taconic Creek Rd, Hillsdale, NY 12529

300/NIGHT Hillsdale, NY Rental Available only December 18 to February 28.: Private, scenic 4-bedroom, 3-bath country home. This peaceful retreat features a cozy wood stove, a well-appointed kitchen, and is offered fully furnished with tasteful, comfortable pieces throughout. Enjoy quiet rural living just minutes from Catamount Mountain Resort. All utilities included, bring your streaming hardware

Rochelle Bartolo Beach & Bartolo Realtors

125 Taconic Creek Rd, Hillsdale, NY 12529
$300,000 Sold Jan 10, 2025

0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529
- Land
- 18.44 Acres
- $16,269 per Acre
Last Sold Summary
- 8% Below List Price
- 219 Days On Market
Current Estimated Value $378,000

Last Listing Agent Robert D Ferris R. Ferris Real Estate, LLC

0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529

/22
Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,896 Sq Ft
39 - stop 26 Justice Rd, Hillsdale, NY 12529

39 - stop 26 Justice Rd, Hillsdale, NY 12529

/30
$660,000 Pending
- 3 Beds
- 2.5 Baths
- 2,256 Sq Ft
63 Cherokee Dr, Hillsdale, NY 12529

Renovated 3 Bedroom, 2.5 Bath, 2256 Sq. Foot Home with Deeded Copake Lake Rights. Welcome to your Hudson Valley retreat!Set on just under an acre in the desirable Hillsdale community, this thoughtfully updatedsplit-level ranch offers modern comfort, stylish upgrades and, year-round recreation with deeded lake rights to Copake Lake-just minutes from your front door.Step inside to

Blanche Mackey Copake Lake Realty Corp.

63 Cherokee Dr, Hillsdale, NY 12529
/18
$3,200 per month
- 3 Beds
- 1.5 Baths
- 1,428 Sq Ft
- House for Rent
765 Harlemville Rd, Hillsdale, NY 12529

Tucked up against hill and overlooking farmland, you'll find this peaceful retreat, a Harlemville hideaway. This furnished home is available for a 6-12 month lease. The perfect spot if you are looking to get away to the country but still want to be within reach of amenities or you want or need to be close to Hawthorne Valley which is only a 2 min drive or 10 min walk away. The house, a rustic

Jennifer Sesma Beach & Bartolo Realtors

765 Harlemville Rd, Hillsdale, NY 12529
/3
$25,000 Sold May 28, 2025

0 Stonehill Dr, Hillsdale, NY 12529
- Land
- 0.96 Acre
- $26,042 per Acre
Last Sold Summary
- 13 Days On Market
Last Listing Agent David Birch Barns & Farms Realty, LLC

0 Stonehill Dr, Hillsdale, NY 12529

/7
Not Listed For Sale
0 - No# Justice Rd, Hillsdale, NY 12529

0 - No# Justice Rd, Hillsdale, NY 12529

/18
$520,000 Pending
- 2 Beds
- 2 Baths
- 1,493 Sq Ft
2253 County Route 21, Hillsdale, NY 12529

Introducing the Kinderhook Cabin, a well cared-for home where every detail has been thoughtfully considered and hand-finished by a master carpenter. Built in 2021, this ranch-style residence offers easy one-level living, a rustic-modern aesthetic and plenty of privacy, set on 5 acres along a beautiful winding country road between Kinderhook and Ghent. Step inside to a large entry hall that flows

Jeffries Blackerby Houlihan Lawrence Inc.

2253 County Route 21, Hillsdale, NY 12529
/19
$4,500 per month
- 3 Beds
- 3 Baths
- 1,902 Sq Ft
- House for Rent
56 Great Spruce Dr, Hillsdale, NY 12529

Discover a private Columbia County/Berkshires retreat set on a secluded, wooded lot just minutes from skiing and top regional attractions. Available as a seasonal furnished rental, this spacious home offers exceptional indoor–outdoor living with mature gardens and an expansive wraparound deck ideal for relaxing or entertaining. Inside, the home offers a flexible layout. The king bedroom features

Kelcey Otten Compass Greater NY, LLC

56 Great Spruce Dr, Hillsdale, NY 12529
/42
$1,350,000 Sold Jun 27, 2025

864 W End Rd, Hillsdale, NY 12529
- 4 Beds
- 3.5 Baths
- 3,540 Sq Ft
- Built 2003
Last Sold Summary
- 4% Above List Price
- $381/SF
- 15 Days On Market
Current Estimated Value $1,311,193

Last Listing Agent John Barbato Compass, Hillsdale

864 W End Rd, Hillsdale, NY 12529

/4
Not Listed For Sale
0 Mitchell St Unit 132496, Hillsdale, NY 12529

0 Mitchell St Unit 132496, Hillsdale, NY 12529

/9
$799,000
- Land
- 56.9 Acres
- $14,042 per Acre
3244 Cr 7, Hillsdale, NY 12529

Beautiful 56+ private acres with views of Copake Lake and Catskill Mountain sunsets. After entering the gates, the forest lined driveway meanders to the sweet spot. There are plenty of options for a home site or 2! Be tucked away but so close to it all! Equidistant to Hudson, NY and Great Barrington, MA., there is so much the area has to offer. From Catamount Ski/Adventure Park to Tangelwood,

Theresa Westlake Copake Lake Realty Corp.

3244 Cr 7, Hillsdale, NY 12529
/51
$15,000 per month
- 5 Beds
- 3.5 Baths
- 3,630 Sq Ft
- House for Rent
136 Tory Hill Farm Rd, Hillsdale, NY 12529

Perched high on a quiet mountainside in one of Hillsdale's most coveted locations, this modern farmhouse sanctuary set on 50+ private acres blends timeless Hudson Valley romance with the ease of updated, contemporary living. Accessed via a private road and tucked discreetly into the hillside, this calming and zen-like retreat offers complete privacy—just minutes from the center of town.

Matthew Snyder Compass, Hillsdale

136 Tory Hill Farm Rd, Hillsdale, NY 12529
/20
$605,000 Sold Sep 17, 2025

15 Roosevelt Dr, Hillsdale, NY 12529
- 1,080 Sq Ft
- Built 1958
Last Sold Summary
- 34% Below List Price
- $560/SF
- 742 Days On Market
Current Estimated Value $541,208

Last Listing Agent Donna Peck Copake Realty

15 Roosevelt Dr, Hillsdale, NY 12529

/41
Est $1,055,870 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,538 Sq Ft
27 Maple St, Hillsdale, NY 12529

27 Maple St, Hillsdale, NY 12529

/6
$199,000
- Land
- 33.31 Acres
- $5,974 per Acre
50 Dugway Rd, Hillsdale, NY 12529

Create Your Own Vision.Escape to 33.31 acres of untouched beauty in Columbia County, NY, and close to Great Barrington, MA. This stunning parcel of wooded land offers complete privacy with no neighbors in sight just you and the tranquility of nature. Imagine the possibilities as you explore the lush, wooded landscape teeming with wildlife. Over 1,677 feet of road frontage, and an old roadway,

Jeffrey McKinney Beach & Bartolo Realtors

50 Dugway Rd, Hillsdale, NY 12529
/10
$2,500 per month
- 2 Beds
- 1 Bath
- 1,107 Sq Ft
- House for Rent
419 SW Sw Colony Rd, Hillsdale, NY 12529

Enjoy lake living at this cozy 2 bedroom 1 bath cottage at beautiful Copake Lake. Lake access providing the perfect spot to relax and swim. Conveniently located near local dining, outdoor recreation and just a short drive to Hudson, Great Barrington and the Taconic State Parkway. 18 month lease preferred. All utilities and maintenance responsibility of the tenant. Must have renters insurance and

Theresa Westlake Copake Lake Realty Corp.

419 SW Sw Colony Rd, Hillsdale, NY 12529
/44
$725,000 Sold Dec 09, 2025

15 Tory Hill Rd, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,592 Sq Ft
- Built 2007
Last Sold Summary
- $280/SF
- 45 Days On Market
Last Listing Agent John Avenia Columbia County RE Specialist

15 Tory Hill Rd, Hillsdale, NY 12529

/2
Est $1,681,710 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,263 Sq Ft
172 W End Rd, Hillsdale, NY 12529

172 W End Rd, Hillsdale, NY 12529

/20
$295,000 Pending
- Land
- 12 Acres
- $24,583 per Acre
376 Approx Whippoorwill Rd, Hillsdale, NY 12529

Discover the true tranquility offered by this 12-acre parcel located on Whippoorwill Road in Hillsdale. Originally created and purchased in 1975, the property has remained undisturbed for the last fifty years. Located only a few miles from the hamlet of Hillsdale on Whippoorwill Road, one of Hillsdale's most scenic and historic roadways. On your way home you will travel by White Oak

John Avenia Columbia County RE Specialist

376 Approx Whippoorwill Rd, Hillsdale, NY 12529
/7
$2,500 per month
- 3 Beds
- 1 Bath
- 924 Sq Ft
- House for Rent
10370 New York 22, Hillsdale, NY 12529

FOR RENT - 2,500/Month | Hillsdale, NY Area Simple home. Beautiful life. Discover country charm in this 3-bedroom, 1-bath ranch (924 sq ft) tucked just outside of Hillsdale — where peaceful living meets endless adventure. Enjoy the best of Columbia County living: hiking, skiing, shopping, dining, and more — all just minutes away. Spend your weekends on the slopes at Catamount Ski Area, grab fresh

Heather Davala Davala Real Estate, LLC

10370 New York 22, Hillsdale, NY 12529
$1,435,000 Sold Feb 07, 2025

656 Breezy Hill Rd, Hillsdale, NY 12529
- 4 Beds
- 3.5 Baths
- 2,272 Sq Ft
- Built 1850
Last Sold Summary
- 4% Below List Price
- $632/SF
- 57 Days On Market
Current Estimated Value $1,481,581

Last Listing Agent John Panzer Elyse Harney Real Estate

656 Breezy Hill Rd, Hillsdale, NY 12529

/11
Est $511,237 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
40 Marsten Ln, Hillsdale, NY 12529

40 Marsten Ln, Hillsdale, NY 12529

/32
$349,900 Under Contract
- 3 Beds
- 1 Bath
- 1,470 Sq Ft
9539 New York 22, Hillsdale, NY 12529

Newly Renovated Hillsdale Gem! Welcome to this beautifully renovated 3-bedroom home in the heart of Hillsdale. Thoughtfully updated with today's buyer in mind, this residence blends modern comfort with timeless charm. Inside, you'll find a bright, welcoming kitchen featuring quartz countertops, high-end vinyl plank flooring, and a suite of updated appliances designed for both style and

Marie Rodriguez Red Apple Realty

9539 New York 22, Hillsdale, NY 12529
/4
$1,295 per month
- 2 Beds
- 1.5 Baths
- 1,200 Sq Ft
- Apartment for Rent
9249 New York 22, Hillsdale, NY 12529

Great duplex on Route 22 near intersection with Route 23. opposite Stewarts Convenience/Gas. 2 levels, 600sf each. Upstairs is living space, kitchen, bath, shower. Downstairs is 2nd BR or office or retail space. Building has mixed commerical/residential zoning. 6 month lease, pay own utilities. Walk to convenience store, restaurant, supermarket, other stores. 1 mile to Ski Catamount. Great

David Birch Barns & Farms Realty, LLC

9249 New York 22, Hillsdale, NY 12529
/57
$1,168,500 Sold Jul 11, 2025

523 Breezy Hill Rd, Hillsdale, NY 12529
- 3 Beds
- 2.5 Baths
- 1,931 Sq Ft
- Built 1973
Last Sold Summary
- 2% Below List Price
- $605/SF
- 44 Days On Market
Current Estimated Value $1,171,751

Last Listing Agent Claudia Crane COMPASS MASSACHUSETTS , LLC GB

523 Breezy Hill Rd, Hillsdale, NY 12529

/2
Est $780,919 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,322 Sq Ft
137 Whippoorwill Rd, Hillsdale, NY 12529

137 Whippoorwill Rd, Hillsdale, NY 12529

/4
$79,500 Pending
- Land
- 4.4 Acres
- $18,068 per Acre
0 Rodman Rd, Hillsdale, NY 12529

Two building lots being sold together as 4.4 acres, each 2.2 acres. Tucked away on a beautiful country road. Information provided is for both lots together, parcel #'s 135.-1-10 & 135.-1-11. (Data entered is for both parcels)Parcels are located between the Berkshires and Hudson offering a short commute either way to an abundance of activities and attractions. 10 minutes to the Taconic State

Theresa Westlake Copake Lake Realty Corp.

0 Rodman Rd, Hillsdale, NY 12529
/29
$965,000 Sold Dec 22, 2025

271 Texas Hill Rd, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,279 Sq Ft
- Built 1930
Last Sold Summary
- $423/SF
- 21 Days On Market
Last Listing Agent Kelcey Otten Compass Greater NY, LLC d/b/a

271 Texas Hill Rd, Hillsdale, NY 12529

/25
Est $770,991 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,272 Sq Ft
274 Texas Hill Rd, Hillsdale, NY 12529

274 Texas Hill Rd, Hillsdale, NY 12529

/4
$199,999 Pending
- 5 Beds
- 3 Baths
- 2,578 Sq Ft
2605 New York 23, Hillsdale, NY 12529

The George and Harriet Sornberger House dates back to the 1870's and is sited among historic homes in Hillsdale, NY. Renovation had started; many original details remain. Last use was a three-unit building, however, it could be restored to a one-family home. Seller financing, including renovation expenses, negotiable. Historic Resource Inventory Form attached.

Lindsay Lebrecht Copake Lake Realty Corp.

2605 New York 23, Hillsdale, NY 12529
/27
$393,500 Sold Apr 15, 2025

3002 State Route 23 --, Hillsdale, NY 12529
- 3 Beds
- 1 Bath
- 1,296 Sq Ft
- Built 1975
Last Sold Summary
- 8% Below List Price
- $304/SF
- 59 Days On Market
Last Listing Agent Paige Paluch LANCE VERMEULEN RE, INC

3002 State Route 23 --, Hillsdale, NY 12529

Est $734,022 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,034 Sq Ft
62 Bucky Rd, Hillsdale, NY 12529

62 Bucky Rd, Hillsdale, NY 12529

/32
$895,000
- 4 Beds
- 2.5 Baths
- 2,225 Sq Ft
2999 New York 23, Hillsdale, NY 12529

Classic Country Home with Pond, Pool & Barns Located just minutes from Catamount Ski Area, Hudson, NY, and Great Barrington, MA. Steeped in history and charm, this distinctive residence—believed to date back to the late 1800s—offers timeless character with thoughtful updates and plenty of space to enjoy country living.This 4 BR, 2.5 BA, 2,225± sq. ft. home is sited on 12+ acres. The rocking

Lindsay Lebrecht Copake Lake Realty Corp.

2999 New York 23, Hillsdale, NY 12529
/10
$1,395,000 Sold Jan 10, 2025

10344 New York 22, Hillsdale, NY 12529
- Land
- 117.7 Acres
- $11,852 per Acre
Last Sold Summary
- 281 Days On Market
Last Listing Agent Parker Meyer Four Seasons Sotheby's Int.

10344 New York 22, Hillsdale, NY 12529

/2
Est $644,926 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 1,090 Sq Ft
76 Overlook Dr, Hillsdale, NY 12529

76 Overlook Dr, Hillsdale, NY 12529

/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
/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 $342,877

Last Listing Agent Lindsay Lebrecht Copake Lake Realty Corp.

118 Yonderview Rd, Hillsdale, NY 12529

/25
Est $573,810 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,650 Sq Ft
15 Henich Ln, Hillsdale, NY 12529

15 Henich Ln, Hillsdale, NY 12529

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