Hillsdale, NY Homes

/20
Est $484,871 Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,494 Sq Ft
3133 County Route 7, Copake, NY 12516

3133 County Route 7, Copake, NY 12516

/18
$274,900
- 2 Beds
- 2 Baths
- 794 Sq Ft
2227 County Route 21, Hillsdale, NY 12529

Tucked away on over 17 serene, subdividable acres in the Town of Kinderhook, this rare offering includes a half-finished 2-bedroom home (a shell awaiting your vision) with a brand-new raised-bed septic system and drilled well (newer pump) & new pressure tank already in place. With frontage on two quiet country roads; County Route 21 and Fowler Lake Rd. this land is a mix of old stone walls,

Michael Castellano Gilcrest Properties

2227 County Route 21, Hillsdale, NY 12529
/32
$675,000 Sold Sep 06, 2024
- 1,500 Sq Ft
- $450/SF
- 27 Days On Market
- 3 Beds
- 2 Baths
- Built 1970
2653 New York 23, Hillsdale, NY 12529

Perched on a hillside with views of the Taconic Ridge, this mid-century ranch is a rarity in the historic hamlet of Hillsdale NY. Three bedrooms, 2 full bathrooms, 2 wood burning fireplaces. The sprawling 1.3 acre lot includes a barn that easily holds four cars, or a workshop for the inspired craftsperson or gardener. The essence of the original house is intact but has been recently updated with

John Barbato Compass, Hillsdale

2653 New York 23, Hillsdale, NY 12529

/11
Not Listed For Sale
10118 State Route 22, Hillsdale, NY 12529

10118 State Route 22, Hillsdale, NY 12529

/9
$220,000
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
10011 New York 22, Hillsdale, NY 12529

Centrally located in Hillsdale, Columbia County, NY. Just about equal distance to Great Barrington, MA and Hudson, NY.This three bedroom, one bathroom, 1,000+ sf home offers a great level yard and a view of your own pond!The area is full of activities such as found at Catamount, the Harlem Valley Rail Trail (nothing motorized), Tanglewood, Copake Country Club, Copake Lake, organic farms, farmer

Theresa Westlake Copake Lake Realty Corp.

10011 New York 22, Hillsdale, NY 12529
/20
$246,000 Sold Sep 05, 2024
- 1,836 Sq Ft
- $134/SF
- 35 Days On Market
- 4 Beds
- 2 Baths
- Built 1910
1337 County Route 21, Ghent, NY 12075

Rare country farmhouse located in the heart of Ghent on Church St. Lovely 4 bedroom, 2 full bath country style living offering cherry floors,1st floor laundry, wood under aluminum siding, a metal roof, fenced yard, with plenty of parking and a very large outbuilding/garage for storage. This home is centrally located just minutes from the Taconic State Parkway and Chatham school district. Church

April Seney Core Real Estate Team

1337 County Route 21, Ghent, NY 12075

Est $1,501,296 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,626 Sq Ft
60 River Rd, Austerlitz, NY 12017

60 River Rd, Austerlitz, NY 12017

/10
$200,000
- Land
- 15 Acres
- $13,324 per Acre
0 Holm Rd, Hillsdale, NY 12529

This 15-acre vacant land presents a unique opportunity for investment or development. Located next to 84 Holm Rd and directly across from the Columbia County Solid Waste Station (Hillsdale Convenience Station), the land offers easy access while maintaining privacy. With scenic views of the rolling hills and open fields, it’s ideal for a farmhouse, agricultural use, or a private retreat. The land

Derek Greene Greene Realty Group

0 Holm Rd, Hillsdale, NY 12529
/17
$355,000 Sold Aug 30, 2024
- 1,111 Sq Ft
- $320/SF
- 62 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1930
2951 State Route 23, Hillsdale, NY 12529

Charming.On the Route 23 corridor between Great Barrington, MA and Hudson, NY, you'll find this lovingly cared for Sears era cottage. Keeping the charm of the era, there are perineal gardens, wood moldings and floors. There is both a front rocking chair porch and an enclosed porch at the rear of the home. The basement below has a one-car garage space, laundry room with 1/2 BA and a root

Lindsay Lebrecht Copake Lake Realty Corp.

2951 State Route 23, Hillsdale, NY 12529

/2
Not Listed For Sale
- 6 Beds
- 3 Baths
- 3,028 Sq Ft
228 County Route 21, Hillsdale, NY 12529

228 County Route 21, Hillsdale, NY 12529

/19
$799,000
- 3 Beds
- 2.5 Baths
- 1,824 Sq Ft
30 Ridge Ln, Hillsdale, NY 12529

Ridge Lane in Hillsdale is the perfect country retreat. Set on 7+ acres on a quiet dead end road. This newly built farmhouse captures the charm and solitude that make Hillsdale so desired. Come in to the mudroom, kick off your shoes and enjoy the space of a real country kitchen. The open living space flows easily to the dining area and living room or out to the deck to enjoy the blue sky. An

Emma French Gabel Real Estate

30 Ridge Ln, Hillsdale, NY 12529
/13
$330,000 Sold Aug 29, 2024
- 1,076 Sq Ft
- $307/SF
- 38 Days On Market
- 4 Beds
- 2 Baths
- Built 1952
4 Texas Hill Rd, Hillsdale, NY 12529

Hillsdale Honey!! 4 Texas Hill, is located on the corner of two quiet country roads. Beautiful recent renovation with all new flooring, wood burning fireplace in Livingroom, 4 bedrooms (2 up and 2 downstairs), 2 baths, beautiful yard with mature trees. Easy to show, short notice OK.

Margaret Bower Avenia Columbia County RE Specialist

4 Texas Hill Rd, Hillsdale, NY 12529

/50
Est $1,641,794 Not Listed For Sale
- 5 Beds
- 3 Baths
- 2,353 Sq Ft
241 Labranche Rd, Hillsdale, NY 12529

241 Labranche Rd, Hillsdale, NY 12529

/3
$299,000
- Land
- 23 Acres
- $13,091 per Acre
0 County Route 21, Hillsdale, NY 12529

Peaceful Easy Feeling in Hillsdale, New York, near the Massachusetts boarder. This 22+ acre parcel is a blend of an open field, stone walls, mature hardwoods and new growth. There is an identified building location at the back of the open field (left), where there is BOHA (on the survey map).A portion of the field is protected from building, however there is still a generous area for your home --

Lindsay Lebrecht Copake Lake Realty Corp.

0 County Route 21, Hillsdale, NY 12529
/29
$550,000 Sold Aug 28, 2024
- 1,556 Sq Ft
- $353/SF
- 247 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1970
10247 Ny-22 --, Hillsdale, NY 12529

Enjoy the incredible views from this well-maintained retro Ranch set in the heart of Columbia County. This charming 3 bedroom, 1 bath home features 1500+ sqft of single level living space. An additional 700+sqft finished bonus/game room with a wood burning fireplace in the lower level, for even more space. Just over 5 acres of open land with so much to offer, including fruit trees, mature

Paige Paluch LANCE VERMEULEN RE, INC

10247 Ny-22 --, Hillsdale, NY 12529

/8
Est $485,713 Not Listed For Sale
- 3 Beds
- 1 Bath
- 984 Sq Ft
25 van Bueran Dr, Hillsdale, NY 12529

25 van Bueran Dr, Hillsdale, NY 12529

/15
$199,000
- Land
- 8 Acres
- $25,254 per Acre
0 Whippoorwill Rd, Hillsdale, NY 12529

Perfect Country Retreat — Build Your Dream Home in HillsdaleEscape to the tranquility of the Hudson Valley with this beautiful, private parcel just minutes from the heart of charming Hillsdale. Set on a quiet, scenic road ideal for walking, jogging, or simply enjoying the peaceful surroundings, this land offers both tranquility and convenience.Enjoy seasonal views of Catamount Ski

Leigh Bahnatka BHHS Hudson Valley Properties

0 Whippoorwill Rd, Hillsdale, NY 12529
/25
$680,000 Sold Aug 27, 2024
- 2,272 Sq Ft
- $299/SF
- 41 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2002
274 Texas Hill Rd, Hillsdale, NY 12529

Welcome to 274 Texas Hill Road: an ideal country escape on 5 private acres with a gorgeous in-ground pool! This home, lovingly cared for by its owners for the past 20 years, benefits from a spectacular location on a secluded country road, and is convenient to Hillsdale, Hudson and Great Barrington. The house enjoys a welcoming layout that flows from room to room, featuring two large living areas

Lori Mendelis Past Member

274 Texas Hill Rd, Hillsdale, NY 12529

/2
Est $1,508,777 Not Listed For Sale
- 3 Beds
- 1 Bath
- 2,352 Sq Ft
539 Birch St, Craryville, NY 12521

539 Birch St, Craryville, NY 12521

/9
$279,000
- 3 Beds
- 3 Baths
- 2,304 Sq Ft
9249 State Route 22, Hillsdale, NY 12529

Mixed Residential/Commercial building, with 2 or 3 rentable spaces. Current RR $36,000. One side of building has commercial reception area down and 1BR apartment above. Rental $1400/m. Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is $875 + $550. Or could be rented to same party for live/work. Building in excellent

David Birch Barns and Farms Realty LLC

9249 State Route 22, Hillsdale, NY 12529
/36
$927,000 Sold Aug 19, 2024
- 2,384 Sq Ft
- $389/SF
- 56 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1981
208 Cambridge Rd, Hillsdale, NY 12529

Discover the epitome of privacy and serenity on 20 wooded acres of pristine landscape. This enchanting property, built in 1981, offers a secluded escape from the hustle and bustle of city life. The main house, thoughtfully designed, features 2 bedrooms, each accompanied by their own full bathrooms, ensuring ultimate comfort and convenience for residents and guests alike.Step into the inviting

Gerard Meenagh The Meenagh Group Realty

208 Cambridge Rd, Hillsdale, NY 12529

/7
Not Listed For Sale
0 Birch Ln Unit 141417, Hillsdale, NY 12529

0 Birch Ln Unit 141417, Hillsdale, NY 12529

/62
$8,850,000
- 4 Beds
- 4.5 Baths
- 6,438 Sq Ft
890 Bald Mountain Rd, Austerlitz, NY 12017

Welcome to The Bald Mountain Estate, the premier family compound in the Upper Hudson Valley. What sets this property apart as one of the most invaluable parcels in the area, is the land- unique, secluded, and beautifully rugged. Inside a gated area of large acreage estates, this 4 building architectural masterpiece property sits on 85 private acres, with multiple trails and an additional building

Rachel Haley Houlihan Lawrence Inc.

890 Bald Mountain Rd, Austerlitz, NY 12017
/25
$863,000 Sold Aug 12, 2024
- 2,126 Sq Ft
- $406/SF
- 73 Days On Market
- 4 Beds
- 2 Baths
- Built 1910
184 Overlook Dr, Hillsdale, NY 12529

For anyone familiar with the town of Hillsdale, located in the northeast corner of the Hudson Valley, will tell you that when a home comes to the market here, it's something that deserves serious consideration. The home on Overlook Drive stands out to be one of the finest opportunities in the entire region. With a desire to bring one's vision to the property, 184 Overlook Drive has all the

Jason Loeb Four Seasons Sotheby's Int.

184 Overlook Dr, Hillsdale, NY 12529

/3
Not Listed For Sale
10695 Ny-22, Hillsdale, NY 12529

10695 Ny-22, Hillsdale, NY 12529

/18
$3,630,000
- Land
- 242 Acres
- $15,000 per Acre
2 Dugway Rd, Austerlitz, NY 12017

242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

Michael Tellerday Houlihan Lawrence, Inc.

2 Dugway Rd, Austerlitz, NY 12017
/44
$1,475,000 Sold Jul 31, 2024
- 2,600 Sq Ft
- $567/SF
- 27 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1887
2367 County Road 11, Hillsdale, NY 12529

Established in 1887, Ives Farm is a charming country property with a well-preserved farmhouse nestled off the road on nearly twelve pastoral acres. A former gentleman's farm, the terrain around the house is undulating and beautifully landscaped, dotted with picturesque outbuildingsincluding the striking original barn. The rest of the wooded acreage, bordering the saltwater pool, is a bit more

Raj Kumar Four Seasons Sotheby's Int.

2367 County Road 11, Hillsdale, NY 12529

Est $448,166 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,704 Sq Ft
4 Lockwood Rd, Craryville, NY 12521

4 Lockwood Rd, Craryville, NY 12521

/15
$3,630,000
- Land
- 242 Acres
- $15,000 per Acre
00 Dugway Rd, Austerlitz, NY 12017

242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

Michael Tellerday Houlihan Lawrence Inc.

00 Dugway Rd, Austerlitz, NY 12017
/2
$999,990 Sold Jan 10, 2025
- 965 Sq Ft
- $1036/SF
- 97 Days On Market
- 2 Beds
- 1 Bath
- Built 2020
40 Dugway Rd, Hillsdale, NY 12529

Nestled into the hillside, this property is known as Springhill Farm, which dates back to the 1700s, an artist retreat. Since 2017, it has been recreated to combine a comfortable live and work environment. A Scandinavian inspired home and apartment built in 2019 & 2020 offer modern amenities and create a peaceful atmosphere. The 2 bedroom, 1 bath house features a large living space with a cozy

Paige Paluch LANCE VERMEULEN RE, INC

40 Dugway Rd, Hillsdale, NY 12529

/3
Est $643,934 Not Listed For Sale
35 Tory Hill Farm Rd, Hillsdale, NY 12529

35 Tory Hill Farm Rd, Hillsdale, NY 12529

/6
$270,000
- Land
- 33 Acres
- $8,106 per Acre
50 Dugway Rd, Hillsdale, NY 12529

Create Your Own VisionEscape to 33.31 acres of untouched beauty nestled between Columbia County, NY, and 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. With over 1,677 feet of road frontage, access is easy.

Jeffrey McKinney Beach & Bartolo Realtors

50 Dugway Rd, Hillsdale, NY 12529

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

0 W End Rd, Hillsdale, NY 12529

/13
$370,000
- Land
- 50 Acres
- $7,413 per Acre
61 Dugway Rd, Hillsdale, NY 12529

Discover Your Dream Retreat: 49+ Acres of Serenity and Potential!Nestled 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 the

Jeffrey McKinney Beach & Bartolo Realtors

61 Dugway Rd, 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

/9
$395,000
- Land
- 22 Acres
- $18,287 per Acre
0 Texas Hill Rd, Hillsdale, NY 12529

This beautiful lot with breathtaking views is waiting for you to come build your dream home, exactly how you want it. With over 20 acres of raw, wooded land, you can create a compound of homes with your family or friends, or build a possible subdivision. This property offers the privacy you're looking for while still being close to town. Minutes from Route 23 and Taconic Hills School.

Ronald Green KW MidHudson

0 Texas Hill Rd, Hillsdale, NY 12529

/2
Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,160 Sq Ft
4 Upper Hollow Rd, Hillsdale, NY 12529

4 Upper Hollow Rd, Hillsdale, NY 12529

/36
$449,900
- 2 Beds
- 1 Bath
- 1,012 Sq Ft
69 SW Colony Rd, Hillsdale, NY 12529

A Lake house in the country is perfect for those seeking a simple way of life. You'll feel like you're living in a storybook. Watch your story unfold before your eyes. Leona's Country Cottage is not your average cottage. It was architecturally designed and built to last many years to come. A new rebuild from the foundation up between 2020-2021 With all new requirements for efficiency and new code

Michelle Ayala BHHS Hudson Valley Properties

69 SW Colony Rd, Hillsdale, NY 12529

/34
Est $1,112,632 Not Listed For Sale
- 8 Beds
- 8.5 Baths
- 2,744 Sq Ft
38 Catamount Rd, Hillsdale, NY 12529

38 Catamount Rd, Hillsdale, NY 12529

/33
$665,000
- 3 Beds
- 2 Baths
- 2,057 Sq Ft
2657 New York 23, Hillsdale, NY 12529

Turnkey Historic Home, Fully Renovated, No Work NeededThis 1810 Greek Revival in Hillsdale has been completely gut-renovated, offering historic charm with none of the hassle. With rising construction costs and new U.S. tariffs driving up renovation expenses. This move-in-ready home is a smart, stress-free investment.All major systems are brand new: HVAC, plumbing, water filters,

Pamela King-Belfor Four Seasons Sothebys Intl

2657 New York 23, Hillsdale, NY 12529

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