Columbia, NY Homes

/27
$1,290,000 Under Contract
- 3 Beds
- 3 Baths
- 1,474 Sq Ft
120 Pumpkin Hollow Rd N, Hillsdale, NY 12529

A WORK OF ART IN HILLSDALETucked into the quiet beauty of Hillsdale, this stunning new build is anything but ordinary. Designed by award-winning architecture firm FORMA, this is their debut in the Hudson Valley. The home feels like a modern sculpture in nature—bold, thoughtful, and completely at ease in its surroundings.From the moment you arrive, there's a sense of calm and

Steven Gray

Compass Greater NY, LLC

(518) 808-2502

120 Pumpkin Hollow Rd N, Hillsdale, NY 12529
/13
$1,100 per month
- 1 Bed
- 1 Bath
- 488 Sq Ft
- Condo for Rent
343 County Route 21c Unit 2, Ghent, NY 12075

343 County Route 21c Unit 2, Ghent, NY 12075
/42
$1,500,000 Sold Aug 01, 2025
- 7,656 Sq Ft
- $196/SF
- 59 Days On Market
- 2 Beds
- 3 Baths
- Built 1928
57 Cold Water St, Hillsdale, NY 12529

Dating back to 1928, this stately brick building originally a Masonic Temple is a stunning blend of historic charm and modern functionality. Meticulously restored and reimagined as an artist live/work space, it offers a unique opportunity to enjoy both a stately residence and/or a thriving business location.Set on a private, gated 0.54-acre lot in the charming Hamlet of Hillsdale, this property

Annabel Taylor Four Seasons Sotheby's Int.

57 Cold Water St, Hillsdale, NY 12529

/22
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

/7
$15,900
- Land
- 1.00 Acre
- $15,900 per Acre
0 Holm Rd, Hillsdale, NY 12529

Own Land A Tangible Asset That Lasts!Secure your future with real, lasting land ownership!This affordable 1-acre lot in Hillsdale, Columbia County, NY, offers a rare opportunity. Property Highlights: Grandfathered Build Rights:-New zoning requires 3 acres this 1-acre lot is grandfathered and eligible for building pending buyer research and approvals. Bonus

Cathy Nation

0 Holm Rd, Hillsdale, NY 12529
/5
$1,600 per month
- 1 Bed
- 1 Bath
- 859 Sq Ft
- Apartment for Rent
32 Anthony St Unit 3c, Hillsdale, NY 12529

Interested parties in this listing must contact the landlord directly at stevenbluestone@gmail.com

Gerard Meenagh The Meenagh Group Realty

32 Anthony St Unit 3c, Hillsdale, NY 12529
/18
$335,000 Sold Jul 24, 2025
- 1,536 Sq Ft
- $218/SF
- 58 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1963
118 Yonderview Rd, Hillsdale, NY 12529

Mid-century ranch that was (is) more than just a house -- it was (is) a home. Many family gatherings were held here. Now it's time for the next generation to carry on.Barely 10 minutes to Catamount Adventure Park/Ski Area and the Berkshires just on the other side of Molasses Hill. Should be less than 2.25 hours from Manhattan.Three + bedrooms +and over 1500 sf of living space.

Lindsay Lebrecht Copake Lake Realty Corp.

118 Yonderview Rd, Hillsdale, NY 12529

/4
Not Listed For Sale
0 Mitchell St Unit 132496, Hillsdale, NY 12529

0 Mitchell St Unit 132496, Hillsdale, NY 12529

/38
$1,295,000
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
2955 New York 23, Hillsdale, NY 12529

Historic Upstate NY Sanctuary - 8.7 Magical Acres in Hillsdale, NY - known for its scenic beauty and small-town charmEscape to your own private paradise on this enchanting 8.7-acre property featuring a charming 1820's cottage, pristine swimming pond with waterfall, and endless outdoor adventures. This secluded sanctuary offers the perfect blend of historic character and natural beauty, just

Chris Getman Houlihan Lawrence Inc.

2955 New York 23, Hillsdale, NY 12529
/5
$1,550 per month
- 1 Bed
- 1 Bath
- 773 Sq Ft
- Apartment for Rent
32 Anthony St Unit 3b, Hillsdale, NY 12529

Interested parties in this listing must contact the landlord directly at stevenbluestone@gmail.com

Gerard Meenagh The Meenagh Group Realty

32 Anthony St Unit 3b, Hillsdale, NY 12529
/57
$1,168,500 Sold Jul 11, 2025
- 1,931 Sq Ft
- $605/SF
- 44 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1973
523 Breezy Hill Rd, Hillsdale, NY 12529

Well maintained ranch set on 8.3 open acres with beautiful views of the Taconic Range. The home with 3 bedrooms and 2.5 baths is lovely as is, and offers excellent possibilities for future additions. Enjoy expansive mountain views from both the open living space and the primary bedroom. A large deck provides great outdoor living/dining space, mature gardens and landscaping finish the property

Claudia Crane COMPASS MASSACHUSETTS , LLC GB

523 Breezy Hill Rd, Hillsdale, NY 12529

/2
Est $1,564,025 Not Listed For Sale
- 3 Beds
- 3 Baths
- 3,263 Sq Ft
172 W End Rd, Hillsdale, NY 12529

172 W End Rd, Hillsdale, NY 12529

/44
$1,295,000
- 4 Beds
- 3 Baths
- 3,282 Sq Ft
9960 New York 22, Hillsdale, NY 12529

Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat.The grand

Pamela King-Belfor Four Seasons Sotheby's Int.

9960 New York 22, Hillsdale, NY 12529
/18
$3,200 per month
- 3 Beds
- 1.5 Baths
- 1,428 Sq Ft
- House for Rent
765 Harlemville Rd, Hillsdale, NY 12529

Tucked up against hill and overlooking farmland, you'll find this peaceful retreat, a Harlemville hideaway. This home is available September 1st for a 1 year lease. The perfect spot if you are looking to get away to the country but still want to be within reach of amenities or you want or need to be close to Hawthorne Valley which is only a 2 min drive or 10 min walk away. The house, a rustic

Jennifer Sesma Beach & Bartolo Realtors

765 Harlemville Rd, Hillsdale, NY 12529
/32
$1,175,000 Sold Jul 03, 2025
- 2,194 Sq Ft
- $536/SF
- 38 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1970
17 White Hill Rd, Hillsdale, NY 12529

Secluded Hillsdale Contemporary on 27.7 acres with incredible far reaching views. Located off a scenic country road, the long private driveway leads to this 2200 square foot home. Originally built in 1970, the house has been upgraded with new windows and sliding doors which create walls of glass for enjoying the natural beauty of the surrounding landscape. The house features 3 bedrooms, 2.5

PATRICIA HINKEIN Patricia A. Hinkein Realty

17 White Hill Rd, Hillsdale, NY 12529

/54
Est $561,462 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,782 Sq Ft
1650 County Route 11, Craryville, NY 12521

1650 County Route 11, Craryville, NY 12521

/25
$1,575,000
- 4 Beds
- 4.5 Baths
- 3,024 Sq Ft
83 Schmeichel Rd, Hillsdale, NY 12529

A Home of Distinction -- there are two distinct sections of this 4+ BR, 4.5 BA, 2 office spaces, 3,666 sf home that is sited on 18.5 private acres. Wood-burning fireplace, 2 gas wood stoves. Pond with gazebo. The main section has 3 BR's, living room, family room, eat-in kitchen, access to the deck with Catamount views and an attached 2-car garage. The addition has a welcoming entrance, 1 BR.

Lindsay Lebrecht Copake Lake Realty Corp.

83 Schmeichel Rd, Hillsdale, NY 12529
/17
$25,000 per month
- 3 Beds
- 2.5 Baths
- 2,490 Sq Ft
- House for Rent
35 Bird Ln, Copake, NY 12516

Beautiful, open and sunny rental walking distance to Copake Lake. Vaulted great room, gourmet kitchen, inviting bedrooms make for the perfect place to spend some time.

Emma French Gabel Real Estate

35 Bird Ln, Copake, NY 12516
/18
$586,000 Sold Jun 30, 2025
- 1,296 Sq Ft
- $452/SF
- 38 Days On Market
- 2 Beds
- 1 Bath
- Built 1988
676 County Route 21, Ghent, NY 12075

Private and Quiet 19+ Acres Surround this Hidden Contemporary Single-level Home. Built with pride and love by the skillful carpenter owner with a soothing stream included. Two bedrooms with large windows allowing one to take in the beauty of the setting and offering seasonal Catskill Mountain views to the west. Sunny and bright kitchen with skylights and glass sliding doors leading to a

Terry Cozzolino Cozzolino Real Estate Inc

676 County Route 21, Ghent, NY 12075

/11
Est $517,693 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,900 Sq Ft
40 Marsten Ln, Hillsdale, NY 12529

40 Marsten Ln, Hillsdale, NY 12529

/25
$1,495,000
- 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

Owen Davidson Brown Harris Stevens HV LLC

161 Stagecoach Rd, Hillsdale, NY 12529
/42
$1,350,000 Sold Jun 27, 2025
- 3,540 Sq Ft
- $381/SF
- 15 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2003
864 W End Rd, Hillsdale, NY 12529

Tucked away on one of Hillsdale's most picturesque and coveted country roads, this extraordinary property is a celebration of nature, craftsmanship, and connection—blending serene seclusion with easy access to the vibrant Hudson Valley lifestyle.Set on a park-like expanse of rolling lawns, mature woodlands, and a dreamy lilypad-covered pond, this one-of-a-kind home offers the welcome sense of

John Barbato Compass, Hillsdale

864 W End Rd, Hillsdale, NY 12529

/2
Est $834,276 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,322 Sq Ft
137 Whippoorwill Rd, Hillsdale, NY 12529

137 Whippoorwill Rd, Hillsdale, NY 12529

/38
$1,100,000
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
110 Meadow Ln, Hillsdale, NY 12529

Ultra-private dead-end lot overlooking Hillsdale, this extraordinary home offers some of the most breathtaking panoramic views in the entire Hudson Valley. Set on 11.9 totally private acres, the property is a rare combination of refined living and natural serenity, with a gentle stream meandering below and a charming footbridge crossing over—straight out of a storybook. There is even a pond with

Michael Castellano Gilcrest Properties

110 Meadow Ln, Hillsdale, NY 12529
/29
$1,220,000 Sold Jun 24, 2025
- 2,100 Sq Ft
- $581/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 2014
90 Overlook Dr, Hillsdale, NY 12529

The Upside Down House, designed by Adam Rolston of INC Architecture and Design. Set on 3 acres along one of Columbia County's most desirable roads, just minutes to downtown Great Barrington and the City of Hudson, NY. Surrounded by hayfields with distant views, this super-energy efficient home features a 40-foot saltwater lap pool, outdoor shower, spring-fed pond, heated tile

Jennifer Harvey Compass Greater NY LLC

90 Overlook Dr, Hillsdale, NY 12529

/37
Est $807,283 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,234 Sq Ft
111 Hunt Rd, Hillsdale, NY 12529

111 Hunt Rd, Hillsdale, NY 12529

/20
$1,100,000
- 2 Beds
- 2 Baths
- 1,419 Sq Ft
75 Upper Hollow Rd, Hillsdale, NY 12529

Nestled along a picturesque, secluded country dirt road--surrounded by a serene 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 reduced taxes and enhanced privacy.An additional structure on the

Janet Kain The Kinderhook Group, Inc.

75 Upper Hollow Rd, Hillsdale, NY 12529
/114
$3,000,000 Sold Jun 10, 2025
- 4,130 Sq Ft
- $726/SF
- 35 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2021
184A Cambridge Rd, Hillsdale, NY 12529

Up a winding country drive in a beautifully rural part of southern Columbia County, a modern house is notched into the hillside. West facing toward the sunset, the home was built to frame a magnificent view of the Catskill Mountains. The interior has wonderfully high 12ft ceilings and wideboard white oak flooring. The large Great Room features a striking wall of glass looking out over the

Annabel Taylor Four Seasons Sotheby's International Realty

184A Cambridge Rd, Hillsdale, NY 12529

/2
Est $620,231 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,600 Sq Ft
694 W End Rd, Hillsdale, NY 12529

694 W End Rd, Hillsdale, NY 12529

/39
$1,195,000
- 4 Beds
- 3.5 Baths
- 2,834 Sq Ft
11 Cold Water St, Hillsdale, NY 12529

This stately Greek Revival sits proudly on a generous village lot in the historic Hamlet of Hillsdale. Dating back to c.1848, the home boasts beautiful architectural proportions and details. Pilasters accent the exterior corners of the house and a front- and side-gabled roof add additional grandeur. Arrive via a front porch — running the full width of the façade — framed with Doric columns. The

MATTHEW CAREY Rouse + Co Real Estate, LLC

11 Cold Water St, Hillsdale, NY 12529
/3
$25,000 Sold May 28, 2025
- Land
- 0.96 Acre
- $26,042 per Acre
- 13 Days On Market
0 Stonehill Dr, Hillsdale, NY 12529

Very private location at end of dead end road. Access to Route 22 and the Taconic Parkway. Easy drive to Hudson, Hillsdale, Catamount Ski Area and Great Barrington.

David Birch Barns & Farms Realty, LLC

0 Stonehill Dr, Hillsdale, NY 12529

Est $706,029 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,034 Sq Ft
62 Bucky Rd, Hillsdale, NY 12529

62 Bucky Rd, Hillsdale, NY 12529

/46
$2,450,000
- 2 Beds
- 2 Baths
- 2,755 Sq Ft
292 White Hill Ln, 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 brings in 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

Jen Harvey COMPASS MASSACHUSETTS , LLC GB

292 White Hill Ln, Hillsdale, NY 12529
/26
$715,000 Sold May 12, 2025
- 1,624 Sq Ft
- $440/SF
- 33 Days On Market
- 3 Beds
- 2 Baths
- Built 1973
35 Stagecoach Rd, Hillsdale, NY 12529

Handcrafted Arts & Crafts Retreat on 5+ Acres in Hillsdale, NYNestled amidst 8.4 acres of lush forest, this one-of-a-kind Arts & Crafts home, hand-built by renowned artist Sheldon Fink, is a true testament to craftsmanship and creativity. Located at 35 Stage Coach Rd, Hillsdale, NY, this 1,624 sq. ft. retreat is surrounded by 8.4 acres of deciduous forest, offering privacy, serenity, and a deep

Maggie Merelle William Pitt Sothebys Intn'l

35 Stagecoach Rd, Hillsdale, NY 12529

/2
Est $652,387 Not Listed For Sale
- 1 Bed
- 1.5 Baths
- 1,090 Sq Ft
76 Overlook Dr, Hillsdale, NY 12529

76 Overlook Dr, Hillsdale, NY 12529

/45
$1,268,500
- 2 Beds
- 3.5 Baths
- 1,700 Sq Ft
401 Collins Street Stop 11, Hillsdale, NY 12529

A Visionary Masterpiece in Columbia County Redefining Country Living. Tucked away on over four serene, wooded acres along one of Columbia County's most coveted roads, this extraordinary 1,700-square-foot contemporary barn home is an architectural work of art a one-of-a-kind residence conceived and crafted by acclaimed designer Angela Patterson. Marrying bold architectural innovation with the

DeWayne A. Powell William Pitt Sotheby's Int'l

401 Collins Street Stop 11, Hillsdale, NY 12529
/33
$310,000 Sold May 01, 2025
- 1,400 Sq Ft
- $221/SF
- 26 Days On Market
- 3 Beds
- 1 Bath
- Built 1955
287 New York 71, Hillsdale, NY 12529

Open HouseSaturday March 1511AM - 1PMThis bright and sunny Hillsdale cottage on the Green River is waiting for you. Cozy details like hard wood floors, exposed beams and a wood heating stove are part of the home's charm. There are 3 bedrooms, one bathroom, and a cool loft for hanging out, office or guest area. The house is on 2.3 acres with The Green River at the rear of the property.This is a

Peter Newman Beach & Bartolo Realtors

287 New York 71, Hillsdale, NY 12529

/10
Est $732,933 Not Listed For Sale
- 5 Beds
- 2 Baths
- 1,928 Sq Ft
1000 Mitchell St, Hillsdale, NY 12529

1000 Mitchell St, Hillsdale, NY 12529

/15
$1,095,000
- 4 Beds
- 2.5 Baths
- 1,344 Sq Ft
25 Nobletown Rd, Hillsdale, NY 12529

Minutes to Great Barrington, this 300 acre wilderness provides waterfalls, stream frontage, pond frontage and something for every outdoor enthusiast. Own your own mountain with trails throughout for hunting, hiking and camping. Build your dream house overlooking a stocked pond and classified trout stream while staying in the 3 bedroom 3 bath caretakers house. The possibilities are endless. Swim

Andrew Gates Houlihan Lawrence

25 Nobletown Rd, Hillsdale, NY 12529
$359,900 Sold Apr 21, 2025
- 1,219 Sq Ft
- $295/SF
- 80 Days On Market
- 3 Beds
- 1 Bath
- Built 1955
631 SW Colony Rd, Hillsdale, NY 12529

Welcome home." We finally got our lake house honey." This is the dream of many, the memories of your home at the lake will remain beautiful from childhood to retirement. Our custom ranch has so many extras. This beauty offers 3 good-sized bedrooms upstairs, and two additional bedrooms/ office downstairs. The setup is a mother-daughter. Two kitchens, two living rooms, separate bedrooms, and

Angel Ayala BHHS Hudson Valley Properties

631 SW Colony Rd, Hillsdale, NY 12529

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