Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

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.

Search SimplerRegister now to save your favorite listings and custom searches. Best of all, we'll email you when new properties that match your criteria hit the market.

Click here to view homes for sale in Hillsdale.

591 Breezy Hill, Hillsdale, NY 12529

Price$1,995,000The 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

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: 3.85% last updated on 2017-10-05

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

599 Whippoorwill, Hillsdale, NY 12529

Price$1,200,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 220699

  • Listings
  • Beds 7
  • Baths 5
  • Sq Ft 4500
  • Acres 78.67

European flare in Hillsdale, NY. Grand in every way. Big acreage for privacy, open fields, expansive western views, gracious sized rooms, screened porch large enough for gathering, dining, and sleeping, chef's kitchen with fireplace, two ponds, stone patio with fire pit, in-ground pool. Private master suite, bedrooms galore, and plenty of bathrooms. Walkout basement with large rec-room, even large mouth bass waiting to take your bait. In short, all of the elements for an un-compromised second home in sought after Hillsdale in stunning Columbia County.

Listing courtesy of Jennifer Capala 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: 3.85% last updated on 2017-10-05

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

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: 3.85% last updated on 2017-10-05

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

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: 3.85% last updated on 2017-10-05

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

218 White Hill, Hillsdale, NY 12529

Price$825,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221135

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 2800
  • Acres 22.1

Nestled in the hills of Hillsdale, this sweet stone cottage is the perfect country getaway. The perfect blend of wood and stone was used to create a home that is warm, inviting and meant to be shared with family and friends . Gather in the open kitchen/dining, in front of the stone fireplace, or on those hot summer days, relax by the pool. Walk and explore nature on your own 22 acres. Close to Hudson and Great Barrington.

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: 3.85% last updated on 2017-10-05

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

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: 3.85% last updated on 2017-10-05

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

173 Overlook, Hillsdale, NY 12529

Price$650,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221115

  • Listings
  • Beds 3
  • Baths 2
  • Sq Ft 2100
  • Acres 3.9

MID-CENTURY RANCH WITH ONE OF THE BEST VIEWS IN HILLSDALE. Far reaching distant southerly views from nearly every room. Privately sited on 3+ acres on a premier road. Shared deeded access to a swimming pond off Meadow Lane. Perfectly located just 20 minutes to Hudson, New York and Great Barrington, Massachusetts.

Listing courtesy of Tom Lynch of Berkshire Property Agents

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: 3.85% last updated on 2017-10-05

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

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: 3.85% last updated on 2017-10-05

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$539,000The 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

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: 3.85% last updated on 2017-10-05

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$539,000The 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: 3.85% last updated on 2017-10-05

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$539,000The 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: 3.85% last updated on 2017-10-05

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

409 Collins, Hillsdale, NY 12529

Price$519,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221083

  • Listings
  • Beds 2
  • Baths 2
  • Sq Ft 1841
  • Acres 5.56

THE ORCHARD. An antique colonial with privacy on 5+ acres on a premier country road. Renovated with style... this house has great flow and a welcoming floorplan. Surrounded by stone walls, beautiful gardens, fruit trees, open lawn, and woods. 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

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: 3.85% last updated on 2017-10-05

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