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Hillsdale NY Homes for Sale

Situated on the Massachusetts-New York border, Hillsdale, New York has undergone several changes over the last several years becoming more vibrant than ever with locally owned businesses and restaurants. Hillsdale offers fantastic hiking and skiing at Catamount Ski Area, one of the largest ski resorts in the Berkshire and Taconic Mountains.

Browse current homes for sale in Hillsdale, NY. Don't hesitate to contact us with any of your questions.

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591 Breezy Hill, Hillsdale, NY 12529

Price$1,650,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 219349

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

Comprised of nearly 60 acres, this once-in-a-lifetime property has had only three owners in its history, passing through the Livingston family, a NY Supreme Court justice, and Wall Street & advertising legend. Situated on both sides of Breezy Hill Road and reaching towards the peak of Catamount Ski Area on the Massachusetts border, the property encompasses acres of open meadows, woodlands, walking trails and swimming pond. Anchored by the 4-bedroom, 5-bath house with indoor pool and views from nearly every room, the property also features a 1-bedroom caretaker / guest cottage, greenhouse, attached & detached garages and perennial gardens. Offering endless possibilities for expansion and re-invention, Breezy Hill Farm inspires creativity and refreshes the soul in every sense and season.

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: 3.94% last updated on 2017-12-21

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$1,125,000The price has recently decreased

Est. Mortgage: $/month

Pending

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, 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: 3.94% last updated on 2017-12-21

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: 3.94% last updated on 2017-12-21

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: 3.94% last updated on 2017-12-21

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: 3.94% last updated on 2017-12-21

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: 3.94% last updated on 2017-12-21

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$795,000The 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

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 3.94% last updated on 2017-12-21

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

40 Sabeff, Hillsdale, NY 12529

Price$649,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222987

  • Listings
  • Beds 3
  • Baths 3
  • Sq Ft 2120
  • Acres 15.8

Stylish & meticulously updated country contemporary on 15+ private acres. As soon as you step inside, this home welcomes you with the perfect balance of modern style and casual country living. The open floor plan offers a living room with wood-burning fireplace & cathedral ceilings, glass-wrapped dining area and a gourmet kitchen with marble counters, stainless appliances and custom cabinetry. The main floor is completed with 3 bedrooms including a generously sized master and two tastefully renovated baths. The finished lower level offers a large game room, media room, full bath and bonus guest space. The 15.8 acre parcel offers complete privacy in a lush wooded setting, with a large deck overlooking the yard and beautiful landscaping including a stone terrace with fire pit.

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: 3.94% last updated on 2017-12-21

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

7 Memory, Hillsdale, NY 12529

Price$565,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 222966

  • Listings
  • Beds 2
  • Baths 2
  • Sq Ft 756
  • Acres 0.5

LAKE FRONT LIVING; Completely remodeled lake cottage with private water frontage and dock on Copake Lake. The kitchen has copper counters, stainless appliances and a wall of glass looking out to the patio, the dining is open to the kitchen as well as the living room with fieldstone fireplace. There is a hall 3/4 bath with laundry and guest room off the living area. The master suite encompasses the entire addition done in 2017; vaulted ceilings, raised personal fireplace, glass doors to deck and beautiful bath.Patio off the kitchen and dining with built in grilling area.a woodland path leads you down the hill to your own private dock.

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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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: 3.94% last updated on 2017-12-21

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: 3.94% last updated on 2017-12-21

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

9508 Route 22, Hillsdale, NY 12529

Price$469,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 221584

  • Listings
  • Beds 3
  • Baths 2
  • Sq Ft 1684
  • Acres 4.2

Beautifully renovated Cape is located in a private setting yet minutes to Hillsdale village. Situated on 4+ acres overlooking a spring-fed pond, this 3 bedroom, 2 bath home is great for entertaining inside and out. Spacious 1200 SF wrap-around deck with views of the pond and distant farmland. The home has wonderful details throughout including gleaming wood floors, granite countertop in the kitchen, wall-mounted AC units, skylight, Thermopane windows, HardieBoard siding, and a generator. This home is move-in ready and easy to show.

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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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: 3.94% last updated on 2017-12-21

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$459,000The price has recently decreased

Est. Mortgage: $/month

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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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: 3.94% last updated on 2017-12-21

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