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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.

45 Hi View Farm, Hillsdale, NY 12529

Price$1,499,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 224757

  • Listings
  • Beds 6
  • Baths 6
  • Sq Ft 3038
  • Acres 16.18

Your quest for a perfect view from an exciting home in a prime location has come to an end! This striking modern home, surrounded by breathtaking mountain views, features soaring wood ceilings & towering west facing windows which bring the dramatic beauty of mountains, fields, water & sky streaming in. Each bedroom comes with a thoughtful corner window providing unique vantage points of pristine Columbia County. A second living space above the garage with two bedrooms & two baths is equally dramatic with a continuous interplay of wood, glass, & mountains. Located equidistant from Great Barrington & Hudson & minutes from Hillsdale, Ski Catamount & hiking trails makes this location pinpoint perfect. This property needs to be experienced to fully appreciated.

Listing courtesy of Marc Bachman and Jennifer Capala 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: 4.45% last updated on 2019-01-17

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

153 Two Town, Hillsdale, NY 12529

Price$1,250,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222281

  • Listings
  • Beds 6
  • Baths 4
  • Sq Ft 6122
  • Acres 51.8

Searching for a large loft like space to entertain your many friends and family? This warm, inviting, shaker inspired farmhouse, and masterfully restored/converted barn, on 50+ acres with stream, pond, expansive views, and privacy set the stage for gathering on a large scale. The main house features 4 bedrooms, 2 full baths, fireplace, inspired woodwork, flowing layout, & fully updated finishes and mechanicals. The stunning converted barn is the showpiece of this property, with soaring living spaces, locally sourced wood work, gourmet kitchen, sleeping loft, two bedrooms, two baths and spa room with hot-tub & sauna. The 50+ acres are situated on a quiet country road surrounded by fine homes and pastoral views and feature 2 ponds, brook, and trails. Successful rental history. Conveniently

Listing courtesy of Jennifer Capala of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY, LENOX

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: 4.45% last updated on 2019-01-17

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$949,000The 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. Close to Great Barrington & many Berkshire attractions.

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: 4.45% last updated on 2019-01-17

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

175 Mitchell, Hillsdale, NY 12529

Price$945,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222362

  • Listings
  • Beds 3
  • Baths 2
  • Sq Ft 2600
  • Acres 10

Thoughtfully converted 1850s hand-hewn barn. Open plan living space. Soaring ceilings and natural light. Stone fireplace. 3 bedrooms. 2 baths. 10 acres with views in every direction. Complete privacy & quiet. Mature landscaping.

Listing courtesy of Scot Cohen of SCOT COHEN 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: 4.45% last updated on 2019-01-17

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

57 Cold Water, Hillsdale, NY 12529

Price$799,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222143

  • Listings
  • Sq Ft 5600
  • Acres 0.52

The Masonic Temple. On the National Register of Historic Places. Built in 1928. 5,600 square feet on 2 floors plus 2,800 square foot basement. 10' ceilings on first floor and 12' on second. Original details throughout. Two restrooms. Parking lot. Town sewer. Hamlet (mixed-use) zoning. 0.542 acre.

Listing courtesy of Scot Cohen of SCOT COHEN 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: 4.45% last updated on 2019-01-17

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

Pending

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: 4.45% last updated on 2019-01-17

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

108 Mitchell, Hillsdale, NY 12529

Price$549,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 223428

  • Listings
  • Beds 5
  • Baths 4
  • Sq Ft 3000
  • Acres 4.9

Located on one of the most desirable streets in Hillsdale, this elegant Contemporary Colonial boasts lots to offer for family and entertaining. This 5 BR, 4 BA home has wonderful indoor and outdoor spaces. From a spacious great room with wood-burning fireplace, incredible screened-in porch, first-floor master, in-ground heated swimming pool and 800 square foot back deck. Minutes to Great Barrington and all Berkshire attractions, this home is in move-in condition. Pool has new chlorine-free system and new energy saving heater. Easy to show.

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: 4.45% last updated on 2019-01-17

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$499,000The 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: 4.45% last updated on 2019-01-17

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$499,000The 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

Do not fill in this field:

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: 4.45% last updated on 2019-01-17

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$499,000The 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: 4.45% last updated on 2019-01-17

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

42 Shepherd Hill, Hillsdale, NY 12529

Price$455,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 223028

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 2773
  • Acres 12.7

Contemporary Colonial in a private location yet minutes to Hillsdale center and 15min to Great Barrington. Kitchen has stainless appliances and great working space and is open to the dining and living area with stone fireplace. Laundry room is off two-car garage and door to fenced pool area. First floor master suite has large bath and walk-in closet. Upstairs there is a landing/office space and two guest rooms with ensuite baths. Large unfinished basement is dry and has high ceilings. Heated pool, rocking chair front porch all on over 12 acres with seasonal views.

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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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.45% last updated on 2019-01-17

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

Hillsdale, NY 12529

Price$375,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 223302

  • Listings

Enter this property from the end of a dead end road up a long private drive, past a potential pond site to the building site with amazing views of the Berkshires and Catamount. Totally private ready for your dream home.

Listing courtesy of Nikki Carchedi of STONE HOUSE PROPERTIES, LLC

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

Do not fill in this field:

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: 4.45% last updated on 2019-01-17

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