Hillsdale, NY Homes

/19
$850,000
- Land
- 150 Acres
- $5,667 per Acre
400 Overlook Dr, Hillsdale, NY 12529

Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

MATTHEW CAREY Rouse + Co Real Estate

400 Overlook Dr, Hillsdale, NY 12529
$805,000

Sold Nov 14, 2025

470 N Mountain Rd, Copake Falls, NY 12517
- 3 Beds
- 3 Baths
- 1,636 Sq Ft
- Built 1840
Last Sold Summary
- 1% Above List Price
- $492/SF
- 8 Days On Market
Current Estimated Value $840,937

Last Listing Agent Tom Lynch Compass Greater NY LLC

470 N Mountain Rd, Copake Falls, NY 12517

/17
Not Listed For Sale

9398 New York 22, Hillsdale, NY 12529
- 3 Beds
- 1 Bath
- 912 Sq Ft
- Built 1951
9398 New York 22, Hillsdale, NY 12529

Last Sold Summary
- 32 Days On Market

/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
/42
$1,500,000

Sold Aug 01, 2025

57 Cold Water St, Hillsdale, NY 12529
- 2 Beds
- 3 Baths
- 7,656 Sq Ft
- Built 1928
Last Sold Summary
- 5% Below List Price
- $196/SF
- 59 Days On Market
Current Estimated Value $1,479,372

Last Listing Agent Annabel Taylor Four Seasons Sotheby's Int.

57 Cold Water St, Hillsdale, NY 12529

/6
Not Listed For Sale

0 Pumpkin Hollow Rd S, Hillsdale, NY 12529
0 Pumpkin Hollow Rd S, Hillsdale, NY 12529

Last Sold Summary
- 190 Days On Market

/7
$39,900
- Land
- 26,571 Sq Ft
- $65,410 per Acre
0 Prach Road Extension Unit 20263433, Claverack, NY 12513

Take advantage of this opportunity to build your dream home on this cleared, flat, .61 acre parcel (with well on property). Conveniently located just minutes to Hudson's restaurants, shops, and Amtrak station, or if you prefer outdoor activities e.g. hiking, kayaking, skiing, and ariel adventure, it's all within a short drive to Bash Bish Falls State Park, Copake Lake, and Catamount Mountain

Wendy Kenney Davala Real Estate, LLC

0 Prach Road Extension Unit 20263433, Claverack, NY 12513
/28
$400,000

Sold Sep 02, 2025

840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529
- 4 Beds
- 2 Baths
- 1,728 Sq Ft
- Built 1900
Last Sold Summary
- 11% Above List Price
- $231/SF
- 27 Days On Market
Current Estimated Value $431,087

Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

840 Pumpkin Hollow Rd S Unit 1, Hillsdale, NY 12529

Est $1,031,000

Not Listed For Sale

0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529
- 4 Beds
- Built 1960
0 Yonderview Rd Unit ONEH6300029, Hillsdale, NY 12529

Last Sold Summary
- 219 Days On Market

/10
$3,600,000
- 4 Beds
- 2 Baths
- 3,200 Sq Ft
90 W End Rd, Hillsdale, NY 12529

For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is

Parker Meyer Four Seasons Sotheby's Int.

90 W End Rd, Hillsdale, NY 12529
/19
$190,000

Sold Jun 05, 2026

2227 County Route 21, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 794 Sq Ft
- Built 1950
Last Sold Summary
- 37% Below List Price
- $239/SF
- 362 Days On Market
Last Listing Agent Michael Castellano Gilcrest Properties

2227 County Route 21, Hillsdale, NY 12529

/10
Not Listed For Sale

10344 New York 22, Hillsdale, NY 12529
- 5 Beds
- 2 Baths
- 2,541 Sq Ft
- Built 1875
10344 New York 22, Hillsdale, NY 12529

Last Sold Summary
- 281 Days On Market

/19
$850,000
- Land
- 150 Acres
- $5,667 per Acre
0 Overlook Dr, Hillsdale, NY 12529

Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

MATTHEW CAREY Rouse + Co Real Estate

0 Overlook Dr, Hillsdale, NY 12529
/41
$786,000

Sold Nov 20, 2025

441 Overlook Dr, Hillsdale, NY 12529
- 3 Beds
- 3 Baths
- 1,875 Sq Ft
- Built 1940
Last Sold Summary
- 1% Below List Price
- $419/SF
- 50 Days On Market
Current Estimated Value $811,738

Last Listing Agent Jennifer Harvey Compass Greater NY LLC

441 Overlook Dr, Hillsdale, NY 12529

/50
Est $351,125

Not Listed For Sale

9376 New York 22, Hillsdale, NY 12529
- 3 Beds
- 1.5 Baths
- 1,684 Sq Ft
- Built 1951
9376 New York 22, Hillsdale, NY 12529

Last Sold Summary
- 30 Days On Market

/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
/13
$725,000

Sold Jan 20, 2026

2318 County Road 11, Hillsdale, NY 12529
- 2 Beds
- 2 Baths
- 1,569 Sq Ft
- Built 2025
Last Sold Summary
- 3% Below List Price
- $462/SF
- 24 Days On Market
Last Listing Agent Emma French Gabel Real Estate

2318 County Road 11, Hillsdale, NY 12529

/13
Est $413,000

Not Listed For Sale

149 Yonderview Rd, Hillsdale, NY 12529
149 Yonderview Rd, Hillsdale, NY 12529

Last Sold Summary
- 21 Days On Market

/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
$426,500

Sold Sep 11, 2025

69 SW Colony Rd, Hillsdale, NY 12529
- 2 Beds
- 1 Bath
- 1,012 Sq Ft
- Built 2021
Last Sold Summary
- 10% Below List Price
- $421/SF
- 358 Days On Market
Current Estimated Value $468,760

Last Listing Agent Michelle Ayala BHHS Hudson Valley Properties

69 SW Colony Rd, Hillsdale, NY 12529

/29
Not Listed For Sale

10247 Ny-22 --, Hillsdale, NY 12529
- 3 Beds
- 1.5 Baths
- 1,556 Sq Ft
- Built 1970
10247 Ny-22 --, Hillsdale, NY 12529

Last Sold Summary
- 247 Days On Market

/29
$425,000

Pending
- 2 Beds
- 1.5 Baths
- 1,630 Sq Ft
44 Collins St, Hillsdale, NY 12529

Classic country homes like this one don't come on the market often and don't last long when they do.This 1933 Cape Cod home is new to the market after 49 years of stewardship by the current owner.The 1.5 acre parcel is deep, with an open and private back yard. In the front, the parcel is bordered by ayear-round stream that is a tributary of the Roeliff Jansen Kill. Collins Street is

Margaret Bower Avenia Columbia County RE Specialist

44 Collins St, Hillsdale, NY 12529
/40
$2,180,000

Sold Mar 02, 2026

35 Harlemville Rd, Hillsdale, NY 12529
- 5 Beds
- 5.5 Baths
- 7,200 Sq Ft
- Built 1980
Last Sold Summary
- 34% Below List Price
- $303/SF
- 441 Days On Market
Current Estimated Value $1,714,384

Last Listing Agent Non MLS HVCR MLS HV Catskill Region MLS

35 Harlemville Rd, Hillsdale, NY 12529

Not Listed For Sale

631 SW Colony Rd, Hillsdale, NY 12529
- 3 Beds
- 1 Bath
- 1,219 Sq Ft
- Built 1955
631 SW Colony Rd, Hillsdale, NY 12529

Last Sold Summary
- 80 Days On Market

/37
$695,000

New Construction
- 3 Beds
- 3 Baths
- 1,824 Sq Ft
30 Ridge Ln, Hillsdale, NY 12529

Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town. Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in mind.

John Barbato Compass, Hillsdale

30 Ridge Ln, Hillsdale, NY 12529
/9
$215,000

Sold Nov 13, 2025

10011 New York 22, Hillsdale, NY 12529
- 3 Beds
- 1 Bath
- 1,040 Sq Ft
- Built 1975
Last Sold Summary
- 17% Below List Price
- $207/SF
Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

10011 New York 22, Hillsdale, NY 12529

/34
Est $2,485,751

Not Listed For Sale

383 Mitchell St, Hillsdale, NY 12529
- 4 Beds
- 3.5 Baths
- 3,800 Sq Ft
- Built 2023
383 Mitchell St, Hillsdale, NY 12529

Last Sold Summary
- 72 Days On Market

/58
$999,900
- 2 Beds
- 2 Baths
- 1,600 Sq Ft
2955 New York 23, Hillsdale, NY 12529

Steeped in Hillsdale's rich history, this extraordinary property began its life as one of the area's original grist mills, situated in the area of Hillsdale once known as Murray's Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

Jason Walch Coldwell Banker Advisor Realty

2955 New York 23, Hillsdale, NY 12529
/85
$3,850,000

Sold Dec 05, 2025

350 Tory Hill Farm Rd, Hillsdale, NY 12529
- 4 Beds
- 5 Baths
- 5,998 Sq Ft
- Built 2008
Last Sold Summary
- 4% Below List Price
- $642/SF
- 142 Days On Market
Current Estimated Value $4,122,325

Last Listing Agent John Barbato Compass, Hillsdale

350 Tory Hill Farm Rd, Hillsdale, NY 12529

/25
Not Listed For Sale

0 Railroad Ln Unit 149543, Hillsdale, NY 12529
0 Railroad Ln Unit 149543, Hillsdale, NY 12529

Last Sold Summary
- 257 Days On Market

/43
$795,000
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
65 Meadow Ln, Hillsdale, NY 12529

With a view as far as the eye can see, 65 Meadow Lane, Hillsdale never fails to amaze from sunrise to sunset, as a full moon lights up your bedroom; hawks fly past wandering clouds, the fiery yellow and burnt red leaves of autumn and the pine trees dripping with snow like confectionary sugar in a winter wonderland. The only sounds you hear are woodpeckers and wild turkeys and your heartbeat

Margaret Bower Avenia Columbia County RE Specialist

65 Meadow Ln, 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 $1,382,937

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

/23
$495,000

New Construction Pending
- 3 Beds
- 2 Baths
- 1,375 Sq Ft
217 Anthony St, Hillsdale, NY 12529

A newly built home ideally located on the edge of the charming hamlet of Hillsdale, NY, this home offers the convenience of true walkability--just steps to everyday essentials including the local hardware store, grocery market, wine shop, post office, town hall, coffee shops, restaurants, and boutique shops. With 3-bedrooms and 2-bathrooms, the home spans approximately 1,350 square feet of modern

John Barbato Compass, Hillsdale

217 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 $575,181

Last Listing Agent Chapin Fish WILLIAM PITT SOTHEBY'S - GT BARRINGTON

58 Deer Track Ln, 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

/29
$785,000

Pending
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
9254 New York 22, Hillsdale, NY 12529

Hillsdale 2500 SF 4BR residence with large deck, inground pool and 60x100 garage on 2.9 acs. Currently Auto Repair Business near Junction of Routes 22 & 23. Incredible opportunity to continue Auto Repair and towing business or convert 60x100 Garage into Storage Facility or other use. House would make great rental property.

David Birch Barns & Farms Realty

9254 New York 22, 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 $653,875

Last Listing Agent John Barbato Compass, Hillsdale

7 Memory 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

/25
$770,000

New Construction $30K PRICE DROP
- 3 Beds
- 3 Baths
- 1,800 Sq Ft
801 Rodman Rd, Hillsdale, NY 12529

New listing in Hillsdale, set high on a quiet dirt road where privacy, peace, and panoramic views define your backdrop. Why wait a year and a half for a new house to be built? This brand-new construction is being sold as it stands today, as a blank unfinished canvas ready for you to make it your own. The structure is in place with a brand-new drilled well, septic system, and 200-amp electrical

Michael Castellano Gilcrest Properties

801 Rodman Rd, Hillsdale, NY 12529

Showing Results 81 - 120, Page 3 of 18

New York Columbia County Hillsdale

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