Hillsdale, NY Homes

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  /27

  $1,290,000 Open Sun 1PM - 3PM

  • 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
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  /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
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  /17

  Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  9398 New York 22, Hillsdale, NY 12529

  9398 New York 22, Hillsdale, NY 12529
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  /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
• 

  

  /18

  $3,600 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 for an academic lease, September 1st to June 30th (10 months). 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

  Jennifer Sesma Beach & Bartolo Realtors

  765 Harlemville Rd, Hillsdale, NY 12529
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  /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
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  /26

  Est $300,470 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  431 SW Colony Rd, Hillsdale, NY 12529

  431 SW Colony Rd, Hillsdale, NY 12529
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  /44

  $1,295,000 Open Sat 12:30PM - 2:30PM

  • 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
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  /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
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  /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
• 

  

  /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
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  /50

  $3,199,000

  • 4 Beds
  • 4.5 Baths
  • 4,635 Sq Ft

  211 Mitchell St, Hillsdale, NY 12529

  Elevate Your Lifestyle in Columbia CountyDiscover the pinnacle of modern luxury in this extraordinary Columbia County estate, set against the breathtaking backdrop of the Berkshire Hills and Catamount Mountains. Spanning over 10 meticulously landscaped acres, this architectural gem blends serene country living with sophisticated design.Step into a grand double-height foyer that

  Christopher Halliburton Beach & Bartolo Realtors

  211 Mitchell St, Hillsdale, NY 12529
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  /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
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  /4

  Not Listed For Sale

  0 Mitchell St Unit 132496, Hillsdale, NY 12529

  0 Mitchell St Unit 132496, Hillsdale, NY 12529
• 

  

  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
• 

  

  /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
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  /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
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  /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
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  /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
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  /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
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  /37

  Est $840,368 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,234 Sq Ft

  111 Hunt Rd, Hillsdale, NY 12529

  111 Hunt Rd, Hillsdale, NY 12529
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  /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
• 

  $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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  /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
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  /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
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  /27

  $393,500 Sold Apr 15, 2025

  • 1,296 Sq Ft
  • $304/SF
  • 59 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1975

  3002 State Route 23 --, Hillsdale, NY 12529

  This cozy cape is ideally situated only minutes fromCatamount Ski Resort, & The Harlem Valley Rail Trail;access to year-round attractions and ideal proximity to the Berkshires and Hudson Valley. An extremely well kept property that has been lived in full time over the past 20+ years.Enter the home through a large enclosed sunroom off the kitchen & dining room-a great option to add more living

  Paige Paluch LANCE VERMEULEN RE, INC

  3002 State Route 23 --, 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
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  /40

  $2,995,000

  • 5 Beds
  • 5.5 Baths
  • 7,200 Sq Ft

  35 Harlemville Rd, Hillsdale, NY 12529

  Where Norman charm meets Hudson Valley splendor, "Dragonfly" stands as a fine example of country living - a rare 130-acre estate that marries grand European sophistication with the pastoral beauty of Claverack. Just twenty minutes from the cultural centers of Hudson and the Berkshires, this property strikes a balance between secluded sanctuary and connected countryside living.A winding private

  Chris Getman Houlihan Lawrence Inc.

  35 Harlemville Rd, Hillsdale, NY 12529
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  /10

  Sold Mar 21, 2025

  • 960 Sq Ft
  • 99 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1925

  199 Rt 217, Ghent, NY 12075

  This sweet-as-can-be cottage with an open floor plan is drenched in sunlight, with a large fenced in yard and beautiful trees for privacy. Set on a quiet parcel just walking distance to the village, great restaurants, a flourishing co-op and the Hawthorne Valley farm store. Located just 2.5 hours from New York City, close to Hudson and the Berkshires.

  Kylah Campeta LYF Homes

  199 Rt 217, Ghent, NY 12075
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  /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
• 

  

  /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

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