Debra Smith
Licensed Real Estate Salesperson
REALTOR®
Margaretville, NY
Office: (845) 586-3321 (973) 479-6445
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42 Shepherd Hill Circle, Hillsdale, NY 12529

New - 4 Hours Ago

Property Description

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.

42 Shepherd Hill Circle | MLS# 20264030

This single family home located at 42 Shepherd Hill Circle, Hillsdale, NY 12529 is currently listed for sale with an asking price of $1,145,000. This property was built in 2003 and has 3 bedrooms and 3 full and 1 partial baths with 2750 sq. ft. Shepherd Hill Circle is located within the Taconic Hills Central Schools school district. Search Hillsdale real estate on debbie-smith.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Cooling: Central Air
Fenced: Yes
Garage: 2 car attached
Heating: Forced Air
Home Style: Cape Cod
Lot Size: 12.70 Acres
Roof Type: Shingle
Taxes: $8,065
Year Built: 2003

Amenities

Primary Downstairs

Feature Descriptions

Appliances: Water Softener Owned, Water Purifier, Washer/Dryer, Washer, Vented Exhaust Fan, Trash Compactor, Refrigerator, Range Hood, Plumbed For Ice Maker, Freezer, Free-Standing Range, Free-Standing Gas Range, Free-Standing Gas Oven, Exhaust Fan, Dishwasher
Exterior: Aluminum Siding
Flooring: Wood
Laundry: Laundry Room, Main Level
Parcel #: 106.-1-16
Pool: Fenced, In Ground
Sewer: Septic Tank
SQFT Total: 2750
Swimming Pool: Yes
Water: Well

Local Schools

School District: Taconic Hills Central Schools

Estimate Your Payment

Estimated Payment

$ 3,554.32 per month $2,548.27 Principal & Interest $672.08 Property Tax $333.96 Homeowner's Insurance

Change Payment Information

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years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Four Seasons Sotheby's Int'l R

Shown By

Agent Name: Debra Smith
Agent Phone: (973) 479-6445
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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 on this site was last updated 07/17/2026. The listing information on this page last changed on 07/17/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Fri 07/17/2026 12:30:43 AM EST) or Global MLS (last updated Fri 07/17/2026 12:22:34 AM EST) or New York State Alliance MLS (last updated Fri 07/17/2026 12:27:06 AM EST) or Hudson Valley Catskill Region MLS (last updated Fri 07/17/2026 12:11:19 AM EST) or OneKey MLS (last updated Fri 07/17/2026 12:28:30 AM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

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