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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 Lots/Land
  • 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$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217596

  • Listings Residential
  • Address 38 Catamount Rd
  • Bedrooms 8
  • Bathroom 9
  • Square Feet 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: 4.15% 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$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217598

  • Listings Commercial
  • Address 38 Catamount Rd
  • Bedrooms 8
  • Square Feet 5488
  • Year Built 1978

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$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 217597

  • Listings Commercial
  • Address 38 Catamount Rd
  • Bedrooms 8
  • Bathroom 9
  • Square Feet 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.

231 State Route 71, Hillsdale, NY 12529

Price$595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218756

  • Listings Residential
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 2352
  • Year Built 1787

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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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.

231 State Route 71, Hillsdale, NY 12529

Price$595,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218759

  • Listings Lots/Land
  • Address 231 State Route 71
  • 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: 4.15% 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

Pending

MLS Number 218222

  • Listings Residential
  • Address 954 Pumpkin Hill Rd
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1700

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

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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.

, Hillsdale, NY 12529

Price$495,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 215650

  • Listings Lots/Land
  • 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.

97 Taconic Creek, Hillsdale, NY 12529

Price$399,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218742

  • Listings Residential
  • Address 97 Taconic Creek Rd
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3072

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

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 Lots/Land
  • 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 Residential
  • Address 9361 Route 22 Rd
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2681

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.

17 End, Hillsdale, NY 12529

Price$289,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 218766

  • Listings MultiFamily
  • Address 17 End Rd
  • Bedrooms 6
  • Bathroom 5
  • Square Feet 2500

Great deal- former school district head quarters on 4 acres 40k+ rent roll.5 units Renters pay all utilities. Broker is owner will consider owner financing, roof and septic recently upgraded. Annual income $40800

Listing courtesy of David Birch of BARNS & FARMS 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.