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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.

, Hillsdale, NY 12529

Price$1,675,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215649

  • Listings
  • Has Waterfront

Magnificent estate property with jaw dropping Western views of the Castskill Mountain Range plus views of the Berkshires Mountains to the East. Very large boating, swimming, fishing & ice skating pond. The building site has been cleared and all road infrastructure is in. Build your dream home on this magical property with sunsets to die for!

Listing courtesy of Marc Bachman 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: 4.15% last updated on 2017-02-16

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$699,000The 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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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: 4.15% last updated on 2017-02-16

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$699,000The 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

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: 4.15% last updated on 2017-02-16

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$699,000The 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: 4.15% last updated on 2017-02-16

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

98 Schmeichel, Hillsdale, NY 12529

Price$549,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215069

  • Listings
  • Beds 5
  • Baths 4
  • Sq Ft 5432
  • Acres 6.08

Hillsdale Contemporary 5400sf, spacious, bright move-in condition, great views of Berkshires and Catamount, first floor master suite, plus 2 additional bedrooms, huge fully equipped modern kitchen, living room with wood burning fireplace, glass doors to deck; lower level is great for guests with 2 additional bedrooms plus family room with fireplace and lots of play or studio space on 6 acres

Listing courtesy of David Birch of BARNS & FARMS REALTY

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

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Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

954 Pumpkin Hill, Hillsdale, NY 12529

Price$525,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218222

  • Listings
  • Beds 2
  • Baths 2
  • Sq Ft 1700
  • Acres 16.96

Incredibly serene setting set off a country road! This charming multi-level Contemporary Farmhouse was designed by architect Dennis Wedlick. Relax and unwind on the stone patio that takes advantage of the valley views and private setting. Great light, country kitchen, and wood floors throughout. Lower level TV room could be easily converted to an additional bedroom. The detached tower/silo building has additional space that could be used as a small studio.

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: 4.15% last updated on 2017-02-16

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

, Hillsdale, NY 12529

Price$495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215650

  • Listings
  • Has Waterfront

Magnificent estate property with jaw dropping Western views of the Castskill Mountain Range. All road infrastructure is in. Build your dream home on this magical property with sunsets to die for!

Listing courtesy of Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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: 4.15% last updated on 2017-02-16

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

, Hillsdale, NY 12529

Price$395,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215651

  • Listings
  • Has Waterfront

Magnificent estate property with jaw dropping Western views of the Castskill Mountain Range. All road infrastructure is in. Build your dream home on this magical property with sunsets to die for!

Listing courtesy of Marc Bachman of WILLIAM PITT SOTHEBY'S INTERNATIONAL REALTY

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: 4.15% last updated on 2017-02-16

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

9361 Route 22, Hillsdale, NY 12529

Price$359,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 216314

  • Listings
  • Beds 4
  • Baths 3
  • Sq Ft 2681
  • Acres 0.86

Classic big scale 1830's Hillsdale village Colonial with enormous character and appeal. Large bright rooms, polished wood floors, great country kitchen, and handsomely updated baths. Set amidst well-stocked gardens and mature trees. A great family home in excellent move-in condition, close to the regions attractions including Hudson, the Berkshires, Millerton, and Copake Lake. An additional 9 acre

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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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: 4.15% last updated on 2017-02-16

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

2601 State Route 23, Hillsdale, NY 12529

Price$239,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215210

  • Listings
  • Beds 5
  • Baths 3
  • Sq Ft 3300
  • Acres 0.88

A stately Victorian, recently refurbished and brought back to life. Recent renovations included new insulation throughout the house and argon-filled replacement windows. You are welcomed to the home by the stately front porch and enter into a warm gathering space with its winding staircase, raised panel walls and hardwood floors. The kitchen is part of a newer addition which contains stainless

Listing courtesy of Allen Halstead of VANTAGEPOINT REALTY

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: 4.15% last updated on 2017-02-16

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

Harlemville Road, Hillsdale, NY 12529

Price$225,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 214010

  • Listings
  • Has Waterfront

Major Price Reduction. 40+ acre estate parcel with spectacular views of Catskills and valley below. Two building sites--one at the top and a second in a flat meadow. This property is located in an area of fine homes just minutes from the Hawthorne Valley Farm Store and Taconic Parkway. Easy drive to Hudson, Chatham, Great Barrington, skiing, and restaurants. Two hours from Manhattan.

Listing courtesy of Nancy Cuddihy 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: 4.15% last updated on 2017-02-16

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

9326 State Route 22, Hillsdale, NY 12529

Price$159,900The price has recently decreased

Est. Mortgage: $/month

MLS Number 218296

  • Listings
  • Baths 2
  • Sq Ft 1248
  • Acres 0.3

Formerly a dentist's office, this building could easily be converted into a delightful home.

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: 4.15% last updated on 2017-02-16

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