Hillsdale, NY Homes

/19
$191,000 Sold Feb 12, 2025
- 2,502 Sq Ft
- $76/SF
- 83 Days On Market
- 5 Beds
- 5 Baths
- Built 1888
22 Anthony St, Hillsdale, NY 12529

This large 2-family home, circa 1888, in the Hamlet of Hillsdale is a rare find. The house consists of 2,500+ sq.ft. of living space, with five bedrooms and three baths, (public records show 4 bedrooms/2 baths) The 0.25-acre property is part of the Hillsdale municipal septic system, with a nice deep back yard that boast two, 2-car garages. Historically approximately 1940's housed a bakery and

Margaret Bower Avenia Columbia County RE Specialist

22 Anthony St, Hillsdale, NY 12529
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/10
Est $715,538 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,928 Sq Ft
1000 Mitchell St, Hillsdale, NY 12529

1000 Mitchell St, Hillsdale, NY 12529

/59
$1,195,000
- 3 Beds
- 2 Baths
- 2,134 Sq Ft
515 Turnpike, Hillsdale, NY 12529

A secluded estate just outside Spencertown with panoramic Taconic views, Camp George blends rustic charm with modern comforts for effortless year-round living. At its heart, a warm, updated log cabin with lofted ceilings and sunlit interiors. A stunning 1,700 sq ft 1850s barn—relocated from the Adirondacks—features vaulted ceilings, wet bar, outdoor kitchen, and sleeping lofts. Swim in the 1-acre

Joseph Briggs William Pitt Sotheby's

515 Turnpike, Hillsdale, NY 12529
/22
$347,000 Sold Feb 11, 2025
- 1,134 Sq Ft
- $306/SF
- 56 Days On Market
- 1 Bed
- 1 Bath
- Built 1984
105 Seekonk Rd, Hillsdale, NY 12529

Nestled on over 4 acres of serene land, this property features a private pond, fenced garden and renovated cabin offering a large studio living space. An attached 1-car garage, and wrap-around deck complete this cozy home. Additionally, there is a potential building site where an old abandoned home currently stands, offering opportunities for expansion.Situated on a quiet country road along the

Paige Paluch LANCE VERMEULEN RE, INC

105 Seekonk Rd, Hillsdale, NY 12529

/25
Est $562,667 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,650 Sq Ft
15 Henich Ln, Hillsdale, NY 12529

15 Henich Ln, Hillsdale, NY 12529

/28
$359,000
- 4 Beds
- 2 Baths
- 1,728 Sq Ft
840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529

As the original farmhouse on this road, this is the epitome of a charming south-facing Upstate home with an abundance of natural light and privacy. Cool in the summer and cozy in the winter, this home is a peaceful retreat all year long.Seated between the Hudson Valley and the Berkshires, the home is just two short miles from Copake Lake. A brief drive in any direction and you'll arrive at

Theresa Westlake Copake Lake Realty Corp.

840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529
$1,435,000 Sold Feb 07, 2025
- 2,272 Sq Ft
- $632/SF
- 57 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1850
656 Breezy Hill Rd, Hillsdale, NY 12529

Discover the charm of this 1800s cedar-shingled home on 29 scenic acres in Hillsdale. The property features a heated pool, private tennis court, and meticulously maintained grounds. With 4 spacious bedrooms and 3.5 baths, it offers comfort and elegance. The living room has a working fireplace and opens to a bright dining room with a bluestone floor. The main-floor primary suite also has a

John Panzer Elyse Harney Real Estate

656 Breezy Hill Rd, Hillsdale, NY 12529

/2
Est $465,399 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,167 Sq Ft
96 SW Colony Rd, Hillsdale, NY 12529

96 SW Colony Rd, Hillsdale, NY 12529

/50
$3,300,000
- 4 Beds
- 3 Baths
- 2,825 Sq Ft
88 Mac Brown Rd, Claverack-Red Mills, NY 12513

Welcome to Mac Brown Waterhouse, a storied 119-acre estate set within a hidden valley offering complete seclusion and timeless beauty. The original 1830s farmhouse is tucked away at the end of a private lane in Claverack, NY, where the road terminates in a round gravel driveway anchored by the property’s original stone well. Two large ponds grace the land, one directly in front of the house that

Anthony D'Argenzio Houlihan Lawrence, Inc

88 Mac Brown Rd, Claverack-Red Mills, NY 12513
/26
Sold Jan 16, 2025
- 3,537 Sq Ft
- 153 Days On Market
- 4 Beds
- 3.5 Baths
73 Mitchell St, Hillsdale, NY 12529

Located down a private winding drive The Passive House is an architect-designed modern home set amidst 15.7 wooded and pastoral acres. The home was designed and constructed to attain passive house certification ensuring a rigorous level of energy efficiency (pending certification by the Passive House Institute US (PHIUS)). Conceived as a fossil-fuel free, all-electric home, solar panels work to

LILLIAN LIN Rouse + Co Real Estate, LLC

73 Mitchell St, Hillsdale, NY 12529

/28
Est $374,914 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,232 Sq Ft
119 Black Grocery Rd, Hillsdale, NY 12529

119 Black Grocery Rd, Hillsdale, NY 12529

/7
$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
/10
$1,395,000 Sold Jan 10, 2025
- Land
- 118 Acres
- $11,852 per Acre
- 281 Days On Market
10344 New York 22, Hillsdale, NY 12529

For the first time on the market in nearly 60 years, Underwood Farm is a remarkable 117 acre spread across the rolling ridgelines of Hillsdale and harboring a magnificent, roaring piece of the Roeliff Jansen Kill. Once a thriving dairy farm, this offering includes an authentic Greek Revival farmhouse with all of its architectural integrity in place: wide plank wooden floors, original sash

Parker Meyer Four Seasons Sotheby's Int.

10344 New York 22, Hillsdale, NY 12529

/27
Est $811,184 Not Listed For Sale
- 3 Beds
- 1.5 Baths
66 Fado Rd, Hillsdale, NY 12529

66 Fado Rd, Hillsdale, NY 12529

/38
$649,000
- 3 Beds
- 1.5 Baths
- 1,248 Sq Ft
47 Cherokee Dr, Hillsdale, NY 12529

Kick off your flip flops and enjoy lake life. Tucked above Copake Lake in Hillsdale, NY, Lakelight is a freshly renovated chalet with deeded lake access, two sunny decks, and something most lake houses don't offer: privacy. This isn't a shoulder-to-shoulder shoreline setup. You've got space, trees, light, and breathing room—with the water just two minutes away down a quiet private road.Set on a

Arlena Armstrong Anatole House LLC

47 Cherokee Dr, Hillsdale, NY 12529
$300,000 Sold Jan 10, 2025
- Land
- 18 Acres
- $16,269 per Acre
- 219 Days On Market
0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529

Highly productive 18 acres of farmland situated near the Village of Hillsdale, and only 1.8 miles to Catamount Ski area, and 9.5 miles to Great Barrington. Property features over 1800 feet of road frontage on Mansfield and Yonderview Roads. Due to the large road frontage, there is flexibility for developing home sites, a possible farm-to-market store, and other uses. Property is currently

Robert D Ferris R. Ferris Real Estate, LLC

0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529

/2
Est $315,563 Not Listed For Sale
- 2 Beds
- 1 Bath
- 884 Sq Ft
189 Prach Rd, Hillsdale, NY 12529

189 Prach Rd, Hillsdale, NY 12529

/19
$347,000
- 2 Beds
- 1 Bath
- 736 Sq Ft
81 SW Sw Colony Rd, Hillsdale, NY 12529

Welcome to Copake Lake!! Sweet two-bedroom, one bath cottage, eat in kitchen, views of the lake from living room and one of the two bedrooms, nice big yard to enjoy outdoor fun. All appliances included. PLUS (As per Seller) water rights along that 20-foot stretch, a buyer may be able to agree with others in the area to extend the existing dock, which could be up to 60 feet into the lake!

Margaret Bower Avenia Columbia County RE Specialist

81 SW Sw Colony Rd, Hillsdale, NY 12529
/37
$570,000 Sold Jan 09, 2025
- 1,685 Sq Ft
- $338/SF
- 61 Days On Market
- 3 Beds
- 2 Baths
- Built 1994
68 Cherokee Dr, Hillsdale, NY 12529

68 Cherokee Drive, Arrowhead Acres, has waterfront private beach & sunshine beaming through every window. Custom Lindal home with Deeded Lake Rights to the over 400 acres of Copake Lake. Just 95 miles to NYC, easy and beautiful commute, enjoy weekend getaways or live here full time as the seller did. Built in 1994, the timeless open floor plan and design features still inspire. The home offers

Margaret Bower Avenia Columbia County RE Specialist

68 Cherokee Dr, Hillsdale, NY 12529

/50
Est $316,464 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,684 Sq Ft
9376 New York 22, Hillsdale, NY 12529

9376 New York 22, Hillsdale, NY 12529

/31
$1,695,000
- Land
- 127 Acres
- $13,336 per Acre
0 Mitchell St Unit 20251360, 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

Jennifer Harvey Compass Greater NY LLC

0 Mitchell St Unit 20251360, Hillsdale, NY 12529
/14
$280,000 Sold Nov 19, 2024
- 2,343 Sq Ft
- $120/SF
- 142 Days On Market
- 4 Beds
- 2 Baths
- Built 1952
52 Connelly Rd, Hillsdale, NY 12529

***** All Investors! All Future Homeowners!*****High Curb Appeal And Quiet Neighborhood Describes This 4 Bedroom 2 Bath. This Copake Getaway Is But A 5 Minute Drive From The Copake Lake. Big Rooms And Tons Of Closet Space. Needs TLC. As Is.

Amjad Mughal M J J Realty

52 Connelly Rd, Hillsdale, NY 12529

/13
Est $360,000 Not Listed For Sale
149 Yonderview Rd, Hillsdale, NY 12529

149 Yonderview Rd, Hillsdale, NY 12529

/19
$875,000
- Land
- 150 Acres
- $5,833 per Acre
0 Overlook Dr, Hillsdale, NY 12529

Situated in Hillsdale, this 150-acre wooded parcel offers an excellent development opportunity with potential for panoramic views of the Berkshires, Taconic Range, and/or the Catskill Mountains. Established logging roads and trails meander through the property, revealing historic stone walls, rock outcroppings, seasonal streams, and charming waterfalls. The site is currently enrolled in a

MATTHEW CAREY Rouse + Co Real Estate LLC

0 Overlook Dr, Hillsdale, NY 12529
/6
$235,000 Sold Nov 13, 2024
- Land
- 62 Acres
- $3,819 per Acre
- 190 Days On Market
0 Pumpkin Hollow Rd S, Hillsdale, NY 12529

A diversity of fields, deciduous forest, and wetlands. Appox 8 acres of open field and many trails throughout. Close vicinity to Copake Lake and equal distance between Hudson, NY and Great Barrington, MA. Catamount Ski and Adventure Park about 15 minutes away. ~Two hours to NYC.

Austin Urban Copake Lake Realty Corp.

0 Pumpkin Hollow Rd S, Hillsdale, NY 12529

/25
Not Listed For Sale
0 Railroad Ln Unit 149543, Hillsdale, NY 12529

0 Railroad Ln Unit 149543, Hillsdale, NY 12529

/19
$875,000
- Land
- 150 Acres
- $5,833 per Acre
400 Overlook Dr, Hillsdale, NY 12529

Situated in Hillsdale, this 150-acre wooded parcel offers an excellent development opportunity with potential for panoramic views of the Berkshires, Taconic Range, and/or the Catskill Mountains. Established logging roads and trails meander through the property, revealing historic stone walls, rock outcroppings, seasonal streams, and charming waterfalls. The site is currently enrolled in a

MATTHEW CAREY Rouse + Co Real Estate, LLC

400 Overlook Dr, Hillsdale, NY 12529
$535,000 Sold Oct 02, 2024
- 2,000 Sq Ft
- $268/SF
- 139 Days On Market
- 3 Beds
- 2 Baths
- Built 1958
70 Connelly Rd, Hillsdale, NY 12529

Architects Victorian 2600 SF home in pristine condition on 2 lots on dead end road. CHECK OUT THE VIRTUAL TOUR!! On lower level entranceway to large living room, dining room, eat in kitchen, possible bedroom and bath. On second level master bedroom + 2 smaller bedrooms with large bath. Mini splits supply heat and air conditioning with back up propane and electric. Floors combine wood with high

David Birch Barns and Farms Realty LLC

70 Connelly Rd, Hillsdale, NY 12529

/31
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,680 Sq Ft
615 County Route 21, Ghent, NY 12075

615 County Route 21, Ghent, NY 12075

/22
$1,695,000
- Land
- 127 Acres
- $13,346 per Acre
0 Mitchell St Unit 246335, 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 246335, Hillsdale, NY 12529
/7
$32,500 Sold Sep 27, 2024
- Land
- 2.53 Acres
- $12,846 per Acre
- 71 Days On Market
0 - No# Justice Rd, Hillsdale, NY 12529

Affordable building lots are challenging to find these days. This newly listed parcel at under $50,000 is a true gem. It is 2.5 acres in size with 350 feet of road frontage on two public roads and a secluded building site in the rear. Situated in the town of Claverack outside the village of Philmont the parcel is minutes from the Taconic State Parkway and a casual 2-hour drive from NYC. The

John Avenia Columbia County RE Specialist

0 - No# Justice Rd, Hillsdale, NY 12529

/17
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

/20
$598,000
- Land
- 13 Acres
- $47,460 per Acre
67 Taconic Creek Rd, Hillsdale, NY 12529

Set down a secluded 1/8-mile driveway, this 12.6-acre property in the tranquil countryside of Hillsdale offers unmatched privacy and sweeping valley and mountain views. This beautiful home site includes plans for a stunning, modern-country 4,200sq ft main house and a separate 1,700sq ft 3 car garage with studio. Ready to build your dream home, this site provides an ideal canvas for creating your

Peter Yates Four Seasons Sotheby's Int.

67 Taconic Creek Rd, Hillsdale, NY 12529
/33
$3,807,437 Sold Sep 20, 2024
- 5,300 Sq Ft
- $718/SF
- 36 Days On Market
- 5 Beds
- 2 Baths
- Built 2014
256 Island Dr, Copake, NY 12521

Inspiration at Copake Lake.Strategically located on the exclusive Island at Copake Lake, is this ~5300 sf home, inspired by the Great Camps of the Adirondacks, and designed by Meyer Davis Studios.Sited on one acre, this waterfront home has five bedrooms (two of which are en-suites) and four bathrooms. The lower level is fabulous for working out or hanging out.Exterior details include cedar

Lindsay Lebrecht Copake Lake Realty Corp.

256 Island Dr, Copake, NY 12521

/37
Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,681 Sq Ft
9361 Ny-22 --, Hillsdale, NY 12529

9361 Ny-22 --, Hillsdale, NY 12529

/24
$845,000
- 6 Beds
- 2 Baths
- 2,998 Sq Ft
60 Anthony St, Hillsdale, NY 12529

Price reduction.1800s farm house. Just waiting for some TLC. This property consists of the main farm house. one very large barn. Addtional 3 out building. One of the back building contains an attractive apartment.The property butts up to the Harlem Valley Rail Trail. Walking distant to the Hamlet of Hillsdale. Including the Roe Jan Brewing Co. IGA, The Hillsdale House, The town park. Less then 5

Gerard Meenagh The Meenagh Group Realty

60 Anthony St, Hillsdale, NY 12529
/41
$1,225,000 Sold Sep 17, 2024
- 2,538 Sq Ft
- $483/SF
- 122 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1841
27 Maple St, Hillsdale, NY 12529

Step into the ambiance of The Dimmick House, a cherished Italianate farmhouse nestled amongst the maple trees in the heart of Hillsdale and once graced by the esteemed Dimmick Family. Indulge your culinary passions in the meticulously revitalized kitchen with Fisher & Paykel appliances and adjoined with the screen porch for indoor/outdoor entertaining. Embrace nearly 180 years of history while

Austin Urban Copake Lake Realty Corp.

27 Maple St, Hillsdale, NY 12529

/45
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

/17
$549,000
- Land
- 83 Acres
- $6,597 per Acre
50 - 61 Dugway Rd, Hillsdale, NY 12529

Two Large Parcels Combine Offering Serenity & Great Potential. 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

Jeffrey McKinney Beach & Bartolo Realtors

50 - 61 Dugway Rd, Hillsdale, NY 12529
/20
$211,000 Sold Sep 13, 2024
- 1,841 Sq Ft
- $115/SF
- 34 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1950
10977 New York 22, Hillsdale, NY 12529

Here is your chance to own a private retreat Upstate! Charming vintage home nestled in the middle ofeverything the Catskills have to offer - an easy drive from NYC and Long Island. Close to Tanglewoodmusic venue & multiple Ski Resorts for year-round fun. Main home offers 3 bedrooms and 1.5 baths.Unfinished second floor is framed out with separate entrance, ready to be transformed into

Scott Varley KW Platform

10977 New York 22, Hillsdale, NY 12529

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