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42 Shepherd Hill Circle

Hillsdale, NY 12529
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Bed 3

Bed

Bath 4

Bath

SqFt2,750

Sqft

Acres12.70

Acres(Lot)

Tucked down a private road and high in the hills of northern Hillsdale, this well-built home offers sweeping mountain views, a beautiful pool, and more than 12 completely private acres--all within 10 minutes of town and 15 minutes from Great Barrington. The house is outfitted with thoughtful details that make country living comfortable and easy--central cooling, ample storage in all the right places, a two-car garage that opens into a mudroom and laundry room, en-suite baths in every bedroom, and a whole-house generator. The first-floor layout flows seamlessly, with two separate living rooms: one with a gas fireplace just off the dining room, and another farther down the hall with easy access to the guest bath. The kitchen is appointed with beautiful new soapstone countertops, a deep fireclay sink from Limoges, France, and a new gas range. At the end of the hall, the spacious and serene primary suite features a walk-in closet designed for two and a full bath with a walk-in shower and oversized soaking tub. The second floor opens to another sitting area and workspace, with two additional suites positioned at opposite ends for privacy. Each bedroom is generously sized, with ample storage and its own full bath. Throughout the home, every window frames a different perspective of the surrounding landscape, from far-reaching mountain views to layered shades of lush greens. On the lower level, a full basement offers abundant storage and workshop opportunities as is, or the opportunity to create additional living or entertainment rooms. Outside, the setting feels entirely its own. A fenced-in pool is surrounded by generous space for lounging and dining, while 12 acres of rolling hills and wooded forest invite exploration. The house sits at approximately 1,200 feet in elevation, with the property rising to nearly 2,300 feet, creating miles of private hiking and mountain biking with rewarding views from the summit. Located just 10 minutes from the center of Hillsdale, 15 minutes from Great Barrington, and 30 minutes from Hudson-- all while feeling a world away. Shepherd Hill is everything one might want in a home, set in a place everyone wishes to be.

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Detail Ic Property Details

Property Type : Residential

Price : $1,145,000

AD Id : 88127000

MLS Id : 20264030

Beds : 3

Lot Size : 12.70 Acres

Living Area Size : 2,750

Year Built : 2003

Garage : 2

County : Columbia

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Feature Features

  • Bedroom Information

    Total beds: 3

    Bathroom Information

    Total Baths: 4 Full Baths: 3 Half Baths: 1

    Room Information

    Has Basement: Yes Basement: Concrete, Full, Unfinished, Walk-Up Access
  • Flooring Information

    Wood
  • Roofing Information

    Shingle
  • Interior Features

    Roof: Shingle Appliances: Dishwasher, Exhaust Fan, Free-Standing Gas Oven, Free-Standing Gas Range, Free-Standing Range, Freezer, Plumbed For Ice Maker, Refrigerator, Range Hood, Trash Compactor, Vented Exhaust Fan, Washer, Washer/Dryer, Water Purifier, Water Softener Owned Laundry Features: Laundry Room, Main Level
  • Heating & Cooling

    Has Heating: Yes Heating: Exhaust Fan, Forced Air Has Cooling: Yes Cooling: Central Air

  • Building Information

    Year Built: 2003 Building Area Total: 2750 Construction Materials: Aluminum Siding Pool Features: Fenced, In Ground Private Pool: No View: Mountain(s)

  • Lot Information

    Main Square Feet: 12.7 Acres Lot Size Acres: 12.7 Lot Size Square Feet: 553212

  • Listing Price Information

    Listing Price: $1145000

  • Tax Information

    Parcel Number: 106.-1-16 Tax Lot: 101 Tax Block: 6 Annual Tax: $8065 Tax Legal Desc: rural res

  • Parking Information

    Attached, Garage

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 2

  • Location Information

    WaterSource: Private, Well
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
292 White Hill Rd, Hillsdale, NY, 12529 $2,195,000 3 3 2,755 2,755 SqFt
417 Overlook Drive, Hillsdale, NY, 12529 $729,900 3 3 2,210 2,210 SqFt
523 Breezy Hill Rd, Hillsdale, NY, 12529 $1,195,000 3 3 1,931 1,931 SqFt
523 Breezy Hill Road, Hillsdale, NY, 12529 $1,195,000 3 3 1,931 1,931 SqFt
523 Breezy Hill Road, Hillsdale, NY, 12529 $1,195,000 3 3 1,931 1,931 SqFt
309 Pine Ridge Lane, Hillsdale, NY, 12529 $900,000 3 3 2,495 2,495 SqFt
25 Nobletown Rd, Hillsdale, NY, 12529 $999,000 4 3 1,344 1,344 SqFt
25 Nobletown Road, Hillsdale, NY, 12529 $999,000 4 3 1,344 1,344 SqFt
25 Nobletown Road, Hillsdale, NY, 12529 $999,000 4 3 1,344 1,344 SqFt
110 Mansfield Road, Hillsdale, NY, 12529 $3,148,000 4 4 3,855 3,855 SqFt

The data relating to real estate for sale on this website comes in part from the Internet Data exchange (IDX) program of the Ulster County Board of REALTORS®. IDX information is provided exclusively for consumers' personal, non - commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright ©2026 Ulster County Board of REALTORS®, Inc.

ByOwner last updated this listing 07/18/2026 @ 02:28

MLS: 20264030 LISTED BY: Sarah Kardos, Four Seasons Sotheby's Int'l R SOURCE: Hudson Valley Catskills Region Multiple List Service (Ulster County Board of REALTORS)

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