Hillsdale, NY Homes

/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
- Last Sold Price $235,000
- Nov 13, 2024
Last Listing Agent Austin Urban Venture Fox Realty Group

/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
/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 $798,152

Last Listing Agent Jennifer Harvey Compass Greater NY LLC

441 Overlook Dr, Hillsdale, NY 12529

Est $842,000 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
- 181% Above List Price
- $337/SF
- 219 Days On Market
- Last Sold Price $300,000
- Jan 10, 2025
Last Listing Agent Robert D Ferris R. Ferris Real Estate, LLC

/43
$2,195,000
- 3 Beds
- 3 Baths
- 2,755 Sq Ft
292 White Hill Rd, Hillsdale, NY 12529

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

Jennifer Harvey Compass Greater NY LLC

292 White Hill 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

/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
- $549/SF
- 281 Days On Market
- Last Sold Price $1,395,000
- Jan 10, 2025
Last Listing Agent Parker Meyer Four Seasons Sotheby's Int.

/31
$1,695,000
- Land
- 127.1 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
$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 $436,772

Last Listing Agent Michelle Ayala BHHS Hudson Valley Properties

69 SW Colony Rd, Hillsdale, NY 12529

/50
Est $326,395 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
- 13% Above List Price
- $172/SF
- 30 Days On Market
- Last Sold Price $290,000
- Jun 24, 2024
Last Listing Agent Nicholas Miuccio Miuccio Real Estate Group

/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
/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 $1,989,454

Last Listing Agent Non MLS HVCR MLS HV Catskill Region MLS

35 Harlemville Rd, Hillsdale, NY 12529

/13
Est $402,000 Not Listed For Sale

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

Last Sold Summary
- 46% Above List Price
- 21 Days On Market
- Last Sold Price $275,500
- Apr 17, 2024
Last Listing Agent John O'Neill-Knasick eXp Realty

/36
$595,000 Pending
- 3 Beds
- 2 Baths
- 2,057 Sq Ft
2657 State Route 23, Hillsdale, NY 12529

Proudly offering one of Hillsdale's most iconic and enduring homes—an exquisite piece of the Hudson Valley's heritage, perfectly positioned at the crossroads between Hudson, NY and Great Barrington, MA. Set in the vibrant and historic hamlet center, this timeless 3-bedroom, 2-bathroom residence is simply beautiful colonial charm.Thoughtfully renovated from top to bottom, the home retains its

John Barbato Compass, Hillsdale

2657 State Route 23, 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

/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
- $353/SF
- 247 Days On Market
- Last Sold Price $550,000
- Aug 28, 2024
Last Listing Agent Paige Paluch WILLIAM RAVEIS - BERKSHIRE

/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
/114
$3,000,000 Sold Jun 10, 2025

184A Cambridge Rd, Hillsdale, NY 12529
- 5 Beds
- 4.5 Baths
- 4,130 Sq Ft
- Built 2021
Last Sold Summary
- 12% Below List Price
- $726/SF
- 35 Days On Market
Current Estimated Value $2,538,886

Last Listing Agent Annabel Taylor Four Seasons Sotheby's International Realty

184A Cambridge 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
- $295/SF
- 80 Days On Market
- Last Sold Price $359,900
- Apr 21, 2025
Last Listing Agent Angel Ayala BHHS Hudson Valley Properties

/13
$299,000 Under Contract
- Land
- 49.91 Acres
- $5,991 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
/29
$1,220,000 Sold Jun 24, 2025

90 Overlook Dr, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 2,100 Sq Ft
- Built 2014
Last Sold Summary
- 3% Below List Price
- $581/SF
- 10 Days On Market
Current Estimated Value $1,247,741

Last Listing Agent Jennifer Harvey Compass Greater NY LLC

90 Overlook Dr, Hillsdale, NY 12529

/34
Est $2,787,736 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
- 1% Below List Price
- $743/SF
- 72 Days On Market
- Last Sold Price $2,825,000
- Jul 12, 2024
Last Listing Agent Nancy Felcetto Brown Harris Stevens Hudson

/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
/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 $3,841,804

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
- Last Sold Price $252,000
- Jun 25, 2024
Last Listing Agent John Avenia Columbia County RE Specialist

/34
$589,900 Pending
- 3 Beds
- 2 Baths
- 2,300 Sq Ft
66 Anthony St, Hillsdale, NY 12529

This home on almost 4 acres with a private pond and scenic mountain and sunset views year-round, also abuts the Harlem Valley Rail Trail. It is withinwalking distance to the village of Hillsdale. Including the Roe Jan Brewing Co. IGA, the Hillsdale House, and the town park. Less then 5-min driveto Catamount; 25 min to Hudson NY, and 20 min to Great Barrington MA.

Susan Calkins STONE HOUSE PROPERTIES, LLC

66 Anthony St, Hillsdale, NY 12529
/26
$715,000 Sold May 12, 2025

35 Stagecoach Rd, Hillsdale, NY 12529
- 3 Beds
- 2 Baths
- 1,624 Sq Ft
- Built 1973
Last Sold Summary
- 23% Above List Price
- $440/SF
- 33 Days On Market
Current Estimated Value $681,671

Last Listing Agent Maggie Merelle William Pitt Sothebys Intn'l

35 Stagecoach Rd, 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
- $259/SF
- 59 Days On Market
- Last Sold Price $435,000
- Nov 30, 2023
Last Listing Agent Beth DeMatteo Berkshire Hathaway HomeService

/72
$775,000 Open Sun 11AM - 2PM
- 7 Beds
- 5 Baths
- 4,608 Sq Ft
9161 New York 22, Hillsdale, NY 12529

A rare and versatile offering making its debut to the market for the very first time, this exceptional mixed-use property presents a unique opportunity to live, work, invest, and create. Set on just under two acres in a prime location, the property has long been owned and occupied by a respected local builder with thoughtful planning and flexibility throughout. Conveniently located just minutes

Paige Backhaus William Raveis Real Estate

9161 New York 22, 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 $1,267,205

Last Listing Agent Steven Gray Compass Greater NY, LLC d/b/a

120 Pumpkin Hollow Rd N, 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
- $203/SF
- 35 Days On Market
- Last Sold Price $385,000
- Sep 29, 2023
Last Listing Agent Karen Davala Davala Real Estate

/23
$495,000 New Construction
- 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 $536,876

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

58 Deer Track 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
- $263/SF
- 45 Days On Market
- Last Sold Price $705,000
- Aug 04, 2023
Last Listing Agent Jessie Bennett William Pitt

/18
$2,999,000
- Land
- 242 Acres
- $12,393 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
/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 $656,480

Last Listing Agent John Barbato Compass, Hillsdale

7 Memory Ln, Hillsdale, NY 12529

/2
Not Listed For Sale

0 Justice Rd, Hillsdale, NY 12529
0 Justice Rd, Hillsdale, NY 12529

Last Sold Summary
- Last Sold Price $73,000
Last Listing Agent Kelsey Winters Davala Real Estate, LLC

/28
$1,275,000
- 1 Bed
- 2 Baths
- 1,700 Sq Ft
401 Collins St Unit Stop 11, Hillsdale, NY 12529

Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County's most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a

Pamela King-Belfor Four Seasons Sotheby's Int.

401 Collins St Unit Stop 11, Hillsdale, NY 12529
$1,037,500 Sold Apr 28, 2026

9715 State Route 22, Hillsdale, NY 12529
- 5 Beds
- 2.5 Baths
- 3,350 Sq Ft
- Built 1788
Last Sold Summary
- 6% Below List Price
- $310/SF
- 139 Days On Market
Current Estimated Value $1,104,836

Last Listing Agent Annabel Taylor Four Seasons Sothebys Intl

9715 State Route 22, Hillsdale, NY 12529

/33
Not Listed For Sale

287 New York 71, Hillsdale, NY 12529
- 3 Beds
- 1 Bath
- 1,400 Sq Ft
- Built 1955
287 New York 71, Hillsdale, NY 12529

Last Sold Summary
- $221/SF
- 26 Days On Market
- Last Sold Price $310,000
- May 01, 2025
Last Listing Agent Peter Newman Beach & Bartolo Realtors

Showing Results 81 - 120, Page 3 of 18

New York Columbia County Hillsdale

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