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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$2,295,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219349

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

A once-in-a-lifetime property of nearly 60 stunning acres with one of the best views in the tri-state area, offering total privacy and easy access to all the Berkshires & Hudson Valley have to offer. Having only 2 owners in its history, 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 expansive western views. The property also features an separate recreation room & indoor pool, caretaker's cottage, greenhouse, attached & detached garages, and perennial gardens. The house needs work to customize for your circumstance but the possibilities are endless!

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: 3.96% last updated on 2017-07-13

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

75 Ridge, Hillsdale, NY 12529

Price$998,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219971

  • Listings
  • Beds 4
  • Baths 4
  • Sq Ft 2400
  • Acres 14

Incredible Catskill views from "Northern Comfort, " a four-bedroom Lindal Cedar home set in a lovely, private, 14-acre setting. Relax in front of the beautiful stone fireplace & enjoy the stunning views from the many windows throughout this attractive home. Post & Beam dwelling with open kitchen/living/dining area which is great for entertaining. Kitchen with cherry cabinets & granite-topped island, radiant heat on the first floor, first-floor bedroom, second-floor bedroom suite with private deck, & two additional bedrooms upstairs. Partially finished lower-level game room/bar area (750 SF) with radiant heat & second fireplace. The lower level also has a workshop area with walk-out access. Screened-in gazebo, bluestone patio, deck with hot tub, outdoor shower, & attached 3-car garage.

Listing courtesy of Lance Vermeulen and Thomas K. Doyle, Sr. 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: 3.96% last updated on 2017-07-13

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: 3.96% last updated on 2017-07-13

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

435 West End, Hillsdale, NY 12529

Price$795,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220326

  • Listings
  • Beds 4
  • Baths 3
  • Sq Ft 3535
  • Acres 4.7

If you are looking for the quintessential white Greek Revival farmhouse on a quiet back road, then this could be the perfect fit. The elegant lines of this handsome country house with it's spacious, bright and updated interior will surely appeal. Lots of extras including a finished walk-up attic, spacious three-season dining porch, and basement wine-cellar. Set amidst 4 1/2 landscaped acres, with natural pond, stone terraces and original out-house to complete this idyllic picture, overlooking conservation farmland. Hudson & Great Barrington with all they offer are close by.

Listing courtesy of Lisa Ann Bouchard of THE KINDERHOOK GROUP - STOCKBRIDGE

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: 3.96% last updated on 2017-07-13

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 219840

  • 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/Inspired by 18th- century, Swiss-Style barns, with sleek black vertical stained cedar siding, the house fits seamlessly with the natural surroundings. Oversize German tilt-and-turn windows maximize the property's natural light and give the feeling of being in a tree house.

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: 3.96% last updated on 2017-07-13

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: 3.96% last updated on 2017-07-13

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$599,000The 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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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.96% last updated on 2017-07-13

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$599,000The 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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Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.96% last updated on 2017-07-13

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$599,000The 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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Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.96% last updated on 2017-07-13

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: 3.96% last updated on 2017-07-13

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 220234

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

Charming Family Compound with 4 bedrooms in the main house, an adorable guesthouse /studio and a wonderful pool area with a pool house. All sited on 35 acres of open fields the meander down to the Green River.. With over 2, 000 feet on the river for fabulous fishing. Its all about the land with the most amazing untouched open meadows.

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: 3.96% last updated on 2017-07-13

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$495,000The 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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Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.96% last updated on 2017-07-13

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