Homes in ZIP Code 12529

/13
$325,000
- Land
- 49.91 Acres
- $6,512 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
/64
$4,450,000 Sold Dec 17, 2025

27 Lake Ridge Ln, Copake Lake, NY 12521
- 4 Beds
- 4.5 Baths
- 6,400 Sq Ft
- Built 2025
Last Sold Summary
- $695/SF
- 27 Days On Market
Last Listing Agent John Barbato Compass, Hillsdale

27 Lake Ridge Ln, Copake Lake, NY 12521

/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

Last Listing Agent Austin Urban Venture Fox Realty Group

/29
$425,000 Under Contract
- 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
/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 $1,466,222

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

57 Cold Water St, Hillsdale, NY 12529

Est $792,000 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
- 164% Above List Price
- $337/SF
- 219 Days On Market
Last Sold Price $300,000

Last Listing Agent Robert D Ferris R. Ferris Real Estate, LLC

/34
$589,900
- 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
/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 $404,836

Last Listing Agent Theresa Westlake Copake Lake Realty Corp.

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

/10
Not Listed For Sale

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

Last Sold Summary
- $549/SF
- 281 Days On Market
Last Sold Price $1,395,000

Last Listing Agent Parker Meyer Four Seasons Sotheby's Int.

/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
/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 $772,583

Last Listing Agent Jennifer Harvey Compass Greater NY LLC

441 Overlook Dr, Hillsdale, NY 12529

/50
Est $321,273 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
- 11% Above List Price
- $172/SF
- 30 Days On Market
Last Sold Price $290,000

Last Listing Agent Nicholas Miuccio Miuccio Real Estate Group

/25
$1,250,000
- 3 Beds
- 2.5 Baths
- 2,200 Sq Ft
161 Stagecoach Rd, Hillsdale, NY 12529

Architecture meets nature in Hillsdale. A fully secluded getaway at the end of a private dead-end road on 7.3 pristine acres. This sunny 3-bedroom, 2-1/2 bath house is inspired by Scandinavian design and features 3 outdoor decks, with views of a spring-fed stream, a crystal clear pond, and deep green woodlands. Central AC for summer days and a wood stove for snowy nights. An ideal layout for

Owen Davidson Brown Harris Stevens HV LLC

161 Stagecoach 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 $386,000 Not Listed For Sale

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

Last Sold Summary
- 40% Above List Price
- 21 Days On Market
Last Sold Price $275,500

Last Listing Agent John O'Neill-Knasick eXp Realty

/26
$690,000
- 3 Beds
- 2.5 Baths
- 2,093 Sq Ft
149 Julianna Dr, Copake, NY 12516

This approximately 2,100-square-foot ranch is sited on ~10 acres within The Birches HOA. The home offers three bedrooms and two-and-a-half bathrooms, an eat-in kitchen, and a dining room that opens to the living room. Both a wood-burning fireplace and a wood stove provide warmth and character. The land is a standout feature, with established fruit-bearing trees and a fenced vegetable garden. An

Lindsay Lebrecht Copake Lake Realty Corp.

149 Julianna Dr, Copake, NY 12516
$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 $438,166

Last Listing Agent Michelle Ayala BHHS Hudson Valley Properties

69 SW Colony Rd, Hillsdale, NY 12529

/9
Not Listed For Sale

25 Nicholson (Catamount) Rd, Copake, NY 12516
- 1 Bed
- 1 Bath
- 620 Sq Ft
- Built 1975
25 Nicholson (Catamount) Rd, Copake, NY 12516

Last Sold Summary
- $222/SF
- 14 Days On Market
Last Sold Price $137,400

Last Listing Agent Karen Climo William Pitt Sothebys Intn'l

/24
$347,000
- 2 Beds
- 1 Bath
- 736 Sq Ft
81 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! Property

Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

81 SW Colony 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

/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

Last Listing Agent Paige Paluch WILLIAM RAVEIS - BERKSHIRE

/44
$1,250,000
- 5 Beds
- 3 Baths
- 2,708 Sq Ft
1 van Bueran Dr, Hillsdale, NY 12529

Tucked away at Copake Lake! This fully renovated home is set on a private 5-acre lot and features an open floor plan with a spacious eat-in kitchen and large island, a dining area that seats 10, and a living room with a grand fireplace and custom built-in benches. French doors open to a large screened-in porch on a wrap-around deck, offering sweeping views of the surrounding landscape. A second,

John Barbato Compass, Hillsdale

1 van Bueran Dr, 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

/23
Not Listed For Sale

50 Lake Ridge Ln, Craryville, NY 12521
50 Lake Ridge Ln, Craryville, NY 12521

Last Sold Summary
- 36 Days On Market
Last Sold Price $600,000

Last Listing Agent John Barbato Compass, Hillsdale

/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
/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

/34
Est $2,769,009 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
- 2% Below List Price
- $743/SF
- 72 Days On Market
Last Sold Price $2,825,000

Last Listing Agent Nancy Felcetto Brown Harris Stevens Hudson

/7
$259,000
- 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 1250/m (month-to- month, should be 1450 on lease). Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is 895 + 400 ( should be 550). Ideal for live/work.

David Birch Barns & Farms Realty, LLC

9249 Route 22 Rd, Hillsdale, NY 12516
/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 $1,265,758

Last Listing Agent Jennifer Harvey Compass Greater NY LLC

90 Overlook Dr, 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

Last Listing Agent John Avenia Columbia County RE Specialist

/19
$225,000
- 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
/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 $3,972,215

Last Listing Agent John Barbato Compass, Hillsdale

350 Tory Hill Farm 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

Last Listing Agent Beth DeMatteo Berkshire Hathaway HomeService

/13
$1,650,000
- 2 Beds
- 2 Baths
- 1,419 Sq Ft
75 Upper Hollow Rd, Hillsdale, NY 12529

Nestled along a private picturesque country dirt road--surrounded by a serene freshwater pond, a flowing creek and wooded acreage, this charming 2 bedroom log cabin offers the perfect escape.The expansive property spans 193 acres, with 18 acres located outside the Columbia Land Conservancy and Forestry Program, allowing for taxes to be reduced and privacy enhanced. Recently renovated with a

Janet Kain The Kinderhook Group, Inc.

75 Upper Hollow Rd, Hillsdale, NY 12529
$359,900 Sold Apr 21, 2025

631 SW Colony Rd, Hillsdale, NY 12529
- 3 Beds
- 1 Bath
- 1,219 Sq Ft
- Built 1955
Last Sold Summary
- $295/SF
- 80 Days On Market
Last Listing Agent Angel Ayala BHHS Hudson Valley Properties

631 SW Colony Rd, 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

Last Listing Agent Karen Davala Davala Real Estate

/13
$1,080,000
- Land
- 72 Acres
- $15,000 per Acre
0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529

Picturesque farmland located close to the Village of Hillsdale, only 1.8 to Catamount Ski Area, and 9.5 miles to Great Barrington. Extensive road frontage, totaling 3979 feet on Yonderview Road and Route 23. Barn complex. This parcel is zoned RU in the Town of Hillsdale. Property currently enjoys an agricultural exemption. Survey available. Inspect Now!

Robert D Ferris R. Ferris Real Estate, LLC

0 Yonderview Rd Unit ONEH6300032, 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 $645,972

Last Listing Agent Maggie Merelle William Pitt Sothebys Intn'l

35 Stagecoach Rd, 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

Last Listing Agent Jessie Bennett William Pitt

/69
$2,995,000
- 4 Beds
- 3 Baths
- 3,641 Sq Ft
88 Mac Brown Rd, Claverack-Red Mills, NY 12513

Welcome to Wolverton Creative Compound, a 119-acre estate in Claverack, NY, offering total privacy, wide southern light, integrated live-work studios, and a large swimmable pond with pebble beach. The 1830s farmhouse features four bedrooms, two baths, original moldings and Dutch doors, a whole-house water filter, and a bright layout for indoor-outdoor living. A fully insulated studio barn is

Anthony D'Argenzio Houlihan Lawrence

88 Mac Brown Rd, Claverack-Red Mills, NY 12513

Showing Results 81 - 120, Page 3 of 18

New York Columbia County Hillsdale 12529

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