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Hillsdale NY Real Estate

Perched on the Massachusetts line in New York, the town of Hillsdale has seen changes in recent years, now becoming a happening area thanks to the work of passionate residents who have opened businesses and restaurants - alongside great antiques shops, Kenver Outdoor Sports Store,  and nearby outdoor trails, a bountiful farmers’ market in the warmer months, and Catamount Ski Area, one of the largest ski resorts in the Berkshire and Taconic Mountains, providing year round fun.

Browse current listings for sale in Hillsdale, NY. Don't hesitate to contact us with any of your questions.

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Click here to view homes for sale in Hillsdale.

591 Breezy Hill, Hillsdale, NY 12529

Price$2,950,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219349

  • Listings
  • Beds 4
  • Baths 7
  • Sq Ft 7163
  • Acres 59.33

Outstanding estate-quality property. A once-in-a-lifetime offering of nearly 60 stunning acres on the western side of Catamount with breathtaking views of the Catskill Mountains. This legacy property spans both sides of Breezy Hill Road, with the eastern side touching the back of Catamount Ski Area, offering acres of meadows, woods & a swimming pond. On the western side of the property sits the 4 bedroom, 5.2 bath spacious yet welcoming home that soaks up every bit of one of the most stunning private views in the Hudson Valley. The property also features an indoor pool, caretaker's cottage, greenhouse, attached & detached garages, and perennial gardens with room to grow for generations to come.

Listing courtesy of Dan Alden of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

871 PUMPKIN HILL, Hillsdale, NY 12529

Price$845,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219706

  • Listings
  • Beds 4
  • Baths 3
  • Sq Ft 2600
  • Acres 6

''Copper House'' is a modern home on six wooden yet light-filled acres off a dirt road in Hillsdale. Built with the upmost attention to the sun as it changes the mood of each room throughout the day; this home offers a wonderful marriage of nature and the modern box. The galley kitchen, dining room, and the guest room all enjoy sawtoothed skylights affording the passage of time and light. The main floor has a 30' wall of shelves separating the kitchen, dining room, and living room from the main hall. Two guest rooms, two full bathrooms, and an office complete the first floor. Lovely master suite takes over most of the second floor with additional bedroom and more office/play space. Very cool, very private, very close to so much.

Listing courtesy of Jen Harvey of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

90 Overlook, Hillsdale, NY 12529

Price$789,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219464

  • Listings
  • Beds 3
  • Baths 2
  • Sq Ft 2000
  • Acres 3.1

The "Upside Down House, " Featured in Architectural Digest and The New York Times, was designed by Adam Rolston of INC Architecture and Design. Located in the bucolic Berkshires on 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, steam shower and soaking tub. https://upside-downhouse.com/

Listing courtesy of Ian Rasch of Alander Real Estate LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

24 Far View, Hillsdale, NY 12529

Price$650,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219384

  • Listings
  • Beds 4
  • Baths 3
  • Sq Ft 2420
  • Acres 4.3

SOPHISTICATED ECO-MODERN RANCH in a sought after area of Hillsdale. 4+ rolling acres on a quiet country road. Totally renovated with top of the line finishes. The open plan living/dining/kitchen has a cathedral ceiling and a wood-burning fireplace. Off the kitchen are glass doors to a large deck. This level also has a master bedroom and master bath, and two bedrooms which share a full bath. One of the bedrooms has resourcefully been divided into two sleeping areas, each with its own closet... perfect for kids or guests. The walk-out lower level has a family room with a fireplace, a bedroom with its own seating area, a full bath with a sauna, and a laundry room. There is also access to a one car attached garage. Perfectly located just 20 minutes to Hudson, NY or Great Barrington, MA.

Listing courtesy of Tom Lynch of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

38 Catamount, Hillsdale, NY 12529

Price$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217596

  • Listings
  • Beds 8
  • Baths 9
  • Sq Ft 5488
  • Acres 4.2

Nestled at the base of Catamount Ski Area sits this spacious 8 bedroom, 8 1/2 bath home--plenty of room for family & friends! The main home has 4 bedrooms, 4 1/2 baths, kitchen with commercial stove, open living/dining area, & lower-level game room with wet bar. Separate building with four bedrooms & four baths, all with own entrances. 2-car garage, shed, & pond on property. Fantastic opportunity!

Listing courtesy of Lance Vermeulen of LANCE VERMEULEN RE, INC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

38 Catamount, Hillsdale, NY 12529

Price$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217598

  • Listings
  • Beds 8
  • Sq Ft 5488
  • Acres 4.2

Nestled at the base of Catamount Ski Area sits this spacious 8 bedroom, 8 1/2 bath home--plenty of room for family & friends! The main home has 4 bedrooms, 4 1/2 baths, kitchen with commercial stove, open living/dining area, & lower-level game room with wet bar. Separate building with four bedrooms & four baths, all with own entrances. 2-car garage, shed, & pond on property. Fantastic opportunity!

Listing courtesy of Lance Vermeulen of LANCE VERMEULEN RE, INC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

38 Catamount, Hillsdale, NY 12529

Price$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217597

  • Listings
  • Beds 8
  • Baths 9
  • Sq Ft 5488

Nestled at the base of Catamount Ski Area sits this spacious 8 bedroom, 8 1/2 bath home--plenty of room for family & friends! The main home has 4 bedrooms, 4 1/2 baths, kitchen with commercial stove, open living/dining area, & lower-level game room with wet bar. Separate building with four bedrooms & four baths, all with own entrances. 2-car garage, shed, & pond on property. Fantastic opportunity!

Listing courtesy of Lance Vermeulen of LANCE VERMEULEN RE, INC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

231 State Route 71, Hillsdale, NY 12529

Price$595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218756

  • Listings
  • Beds 5
  • Baths 4
  • Sq Ft 2352
  • Acres 35

Charming Compound. Four bedroom main house, adorable guest house/studio, and a wonderful pool area and pool house with a bathroom. All set on 35 acres of open fields that meander down to the Green River with over 2000 ft of frontage on the river for fabulous fishing. Its all about the land with the most amazing un touched open fields

Listing courtesy of Mary R White of BARNBROOK REALTY, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

231 State Route 71, Hillsdale, NY 12529

Price$595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218759

  • Listings
  • Has Waterfront

Gorgeous open land with 2000' of frontage on the Greenriver. Property can be subdivided. Frontage on Overlook as well as Rt 71.

Listing courtesy of Mary R White of BARNBROOK REALTY, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

42 Shephard Hill, Hillsdale, NY 12529

Price$525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219148

  • Listings
  • Beds 3
  • Baths 4
  • Sq Ft 2774
  • Acres 12.7

Private colonial with views, in ground pool and sweeping lawn on nearly 13 acres adjacent to protected land. Convenient to all major attractions, this comfortable home boasts a large kitchen with stainless appliances and granite countertops and 2 separate living spaces, one with a gas fireplace. The ground-floor master is large and features an ensuite bathroom with glass enclosed shower and a deep soaking tub. A mud/laundry room is located next to the entrance to 2 car attached garage. Upstairs are 2 more bedrooms each with their own bathroom. A large study/media space is situated between the 2 bedrooms. 5 minutes to hillsdale center, 5 minutes to catamount ski , 12 minutes to downtown great barrington and close to all state parks, incredible road biking and hiking, this home has it all

Listing courtesy of Russ Stein of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

6 Lands End, Hillsdale, NY 12529

Price$425,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218950

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 1630
  • Acres 0.33

Copake Lake is a 400+ acres in southern Columbia county NY. This fabulous property is nestled between the Catskill mountains and the Berkshire Hills. Be it fishing, water skiing, downhill skiing, kayaking or swimming. This location has it all. Approximately a 2-hour drive from NYC. Minutes to the Taconic State Parkway or Route #22. It is also accessible to both Metro North (Wassaic NY) and Amtrak (Hudson NY) train stations. Less than an hour to Albany NY. 20 minutes to the Berkshires (Tanglewood, Jacobs Pillow). About 2.5 hours to Boston MA. A beautiful public golf course is also located right here on Copake Lake.

Listing courtesy of Gerard Meenagh of BARNBROOK REALTY, INC.

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

97 Taconic Creek, Hillsdale, NY 12529

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218742

  • Listings
  • Beds 4
  • Baths 3
  • Sq Ft 3072
  • Acres 6.09

Good morning sunshine! Easy living in this spacious, east-facing contemporary overlooking protected farmland. Three full levels of living space. Gleaming wood floors. Open floor plan on main level includes four sets of french doors which open to deck and views, a WB fireplace and soaring ceiling with skylight. Plenty of bedrooms upstairs plus lower level Great Room, perfect for your art studio, morning yoga, or entertaining a crowd. A peaceful, private location yet minutes to the Hamlet of Hillsdale, Taconic Parkway, skiing, and restaurants. Hudson, Great Barrington and Chatham just 25 minutes away.

Listing courtesy of Nancy Cuddihy of STONE HOUSE PROPERTIES, LLC

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.02% last updated on 2017-05-25

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.