Hillsdale, NY Homes for Sale under $400,000

/19
$325,000
- 2 Beds
- 1 Bath
- 736 Sq Ft
81 SW Colony Rd, Hillsdale, NY 12529

Welcome to THE UPSTATE RETREAT--where every day feels like a vacation on Copake Lake, the largest lake in Columbia County, spanning approximately 425 acres. Whether you're searching for the perfect weekend escape, a summer lake house, or a year-round getaway, this charming 2-bedroom, 1-bath bungalow offers the quintessential upstate lifestyle just over two hours from New York City. Beyond the

Mark Saxby

Berkshire Hathaway HomeService

81 SW Colony Rd, Hillsdale, NY 12529
/5
$225,000
- Land
- 6 Acres
- $37,500 per Acre
L135.2 Rockledge Rd, Hillsdale, NY 12529

Escape to your own private sanctuary in the heart of Columbia County's coveted Hudson Valley. This 6 acre wooded parcel on scenic Rockledge Road offers the perfect canvas for your dream retreat, with mature trees providing natural privacy and a peaceful, secluded setting that feels worlds away from the everyday. Ideally situated in the Town of Hillsdale -- one of the region's most sought-after

Jamie Mazuryk

Venture Fox Realty Group LLC

L135.2 Rockledge Rd, Hillsdale, NY 12529
/6
$175,000

$120K PRICE DROP
- Land
- 33.31 Acres
- $5,254 per Acre
50 Dugway Rd, Hillsdale, NY 12529

Escape to 33.31 acres of untouched beauty in Columbia County, NY. 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. This parcel features a dynamic topography of hills that reach an elevation of over 1,000 feet. With this parcel,

Jeffrey McKinney Beach & Bartolo Realtors

50 Dugway Rd, Hillsdale, NY 12529
/33
$389,000
- 4 Beds
- 1 Bath
- 2,229 Sq Ft
1953 County Road 11, Claverack, NY 12513

Step into a home that feels like it has been quietly telling its story since the 1800's, where every beam and board carries the charm of a bygone era. This classic colonial residence preserves its original character with exposed beams stretching across the main floor and a layout that balances simplicity with purpose. The kitchen is modest yet functional, anchored by a traditional wood store that

Karen Davala Davala Real Estate, LLC

1953 County Road 11, Claverack, NY 12513
/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
/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
/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
/22
$365,000
- 1 Bed
- 1 Bath
- 684 Sq Ft
251 Overlook Dr, Hillsdale, NY 12529

Are you dreaming of times spent tucked away in a rustic cabin, preferably wrapped in a cozy blanket in front of a roaring fireplace? Or maybe you're dreaming of walking barefoot in the stream that feds into the Green River and sunbathing with rays of sunshine beaming through the trees? Welcome to 251 Overlook, Hillsdale NY! Cira 1900 Cottage in the woods, built on the side of a mountain, on 4.5

Margaret Bower Avenia Columbia County RE Specialist

251 Overlook Dr, Hillsdale, NY 12529
/13
$299,000

$96K PRICE DROP
- Land
- 49.91 Acres
- $5,991 per Acre
61 Dugway Rd, Hillsdale, NY 12529

Discover Your Dream Retreat: 49+ Acres of Serenity and Potential! Located between the charming towns of Chatham, NY, and Great Barrington, MA, this stunning parcel of over 49 acres offers a unique blend of privacy and accessibility. With impressive road frontage on two roads, this property is easily accessible while still providing a tranquil escape. Imagine waking up to the soothing sounds of

Jeffrey McKinney Beach & Bartolo Realtors

61 Dugway Rd, Hillsdale, NY 12529
/20
$299,000

$26K PRICE DROP
- Land
- 22.84 Acres
- $13,091 per Acre
0 County Route 21, Hillsdale, NY 12529

Welcome to DREAMLAND.Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow--perfectly oriented for southern

Pamela King-Belfor Four Seasons Sotheby's Int.

0 County Route 21, Hillsdale, NY 12529
/66
$290,000

Coming Soon
- 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
/17
$399,000

$150K PRICE DROP
- 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
/31
$349,900
- 4 Beds
- 2 Baths
- 2,080 Sq Ft
9161 Ny-22, Copake, NY 12516

Just minutes from the center of Hillsdale, Roe Jan Park, and the Harlem Valley Rail Trail, this split-level ranch offers a convenient location with easy access to some of the area's most popular outdoor and community amenities. The 2,080-square-foot home features four bedrooms and two bathrooms, providing a practical layout with space for everyday living. A bright sunroom serves as a natural

Paige Backhaus William Raveis Real Estate

9161 Ny-22, Copake, NY 12516

New York Columbia County

Home Prices in Hillsdale, NY

The median home sale price in Hillsdale, NY is $786,000, down 15% year-over-year. Homes in Hillsdale sell in 100 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $786,000	Median Single Family Sale Price $931,200
Median Townhouse Sale Price $580,000	Median 2 Bedroom Sale Price $567,000
Median 1 Bedroom Sale Price $732,500	Average Price Per Sq Ft $498
Number of Homes for Sale 35	Last 12 months Home Sales 55
Months of Supply 7.60	Median List Price $972,000
Median Change From 1st List Price 4%	Median Home Sale Price YoY Change -15%

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