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Pending
  • $1,145,000

    42 Shepherd Hill Circle, Hillsdale, NY 12529

    3beds
    2,750sqft
    Loading
    Single Family Residence
    Built in 2003
    12.7 Acres Lot
    $1,134,700 Zestimate®
    $416/sqft
    $-- HOA

    What's special

    Gas fireplaceWhole-house generatorBeautiful poolPrivate roadCentral coolingNew gas rangeSweeping mountain views
    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.
    28 days
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    1,752
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    119
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    Zillow last checked:

    Listing updated:

    Listed by:

    Four Seasons Sotheby's Int'l R 845-684-0084,

    Sarah Kardos

    Source: HVCRMLS,MLS#: 20264030MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Bedroom
      • Level: Second
      Bedroom
      • Level: Second
      Primary bathroom
      • Level: First
      Bathroom
      • Level: Main
      Bathroom
      • Level: Second
      Bathroom
      • Level: Second
      Basement
      • Level: Basement
      Den
      • Level: Basement
      Dining room
      • Level: First
      Family room
      • Level: Main
      Kitchen
      • Level: Main
      Laundry
      • Level: Basement
      Heating
      • Forced Air
      Cooling
      • Central Air
      Appliances
      • Included: 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
      • Laundry: Laundry Room, Main Level
      Features
      • Primary Downstairs
      • Flooring: Wood
      • Doors: Sliding Doors
      • Basement: Concrete,Full,Unfinished,Walk-Up Access
      Interior area
      • Total structure area: 2,750
      • Total interior livable area: 2,750 sqft
      • Finished area above ground: 2,750
      • Finished area below ground: 0

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage - Attached
      • Attached garage spaces: 2
      Features
      • Pool features: Fenced, In Ground
      • Fencing: Partial,Wood
      • Has view: Yes
      • View description: Mountain(s)
      Lot
      • Size: 12.7 Acres
      Details
      • Parcel number: 106.116
      • Zoning: res

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Cape Cod
      • Property subtype: Single Family Residence
      Materials
      • Aluminum Siding
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 2003

      Utilities & green energy

      • Electric: 200+ Amp Service
      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Location
      • Region: Hillsdale

      Financial & listing details

      • Price per square foot: $416/sqft
      • Tax assessed value: $439,000
      • Annual tax amount: $8,065
      • Date on market: 7/17/2026

        Estimated market value

        $1,134,700

        $1.08M - $1.19M

        $6,300/mo

        Price history

        DateEventPrice
        7/29/2026Pending sale$1,145,000$416/sqft
        Source: HVCRMLS #20264030 Report a problem
        7/17/2026Listed for sale$1,145,000+160.8%$416/sqft
        Source: HVCRMLS #20264030 Report a problem
        1/18/2019Sold$439,000-3.5%$160/sqft
        Source: BCMLS #223028 Report a problem
        11/27/2018Pending sale$455,000$165/sqft
        Source: BERKSHIRE PROPERTY AGENTS #223028 Report a problem
        10/3/2018Price change$455,000-0.9%$165/sqft
        Source: BERKSHIRE PROPERTY AGENTS #223028 Report a problem
        5/18/2018Listed for sale$459,000$167/sqft
        Source: BERKSHIRE PROPERTY AGENTS #223028 Report a problem
        3/31/2018Listing removed$459,000$167/sqft
        Source: BERKSHIRE PROPERTY AGENTS #219148 Report a problem
        3/2/2018Price change$459,000-7.3%$167/sqft
        Source: BERKSHIRE PROPERTY AGENTS #219148 Report a problem
        6/29/2017Price change$495,000-5.7%$180/sqft
        Source: BERKSHIRE PROPERTY AGENTS #219148 Report a problem
        5/14/2017Listed for sale$525,000-3.2%$191/sqft
        Source: BERKSHIRE PROPERTY AGENTS #219148 Report a problem
        9/17/2004Sold$542,500+1105.6%$197/sqft
        Source: Public Record Report a problem
        3/1/2002Sold$45,000$16/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $439,000
        2024-- $439,000
        2023-- $439,000
        2022-- $439,000
        2021-- $439,000
        2020-- $439,000
        2019-- $439,000 +23.7%
        2018-- $355,000
        2017$7,319 $355,000
        2016-- $355,000
        2015-- $355,000
        2014-- $355,000 -8.5%
        2013-- $388,000 -51%
        2012-- $792,400
        2011-- $792,400
        2010-- $792,400
        2009-- $792,400
        2008-- $792,400 +57.6%
        2007-- $502,900 -5.6%
        2006-- $532,900
        2005-- $532,900 +42.3%
        2004-- $374,500
        2003-- $374,500 +793.8%
        2002-- $41,900
        2001-- $41,900
        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 12529

        Getting around

        0 / 100
        Car-Dependent
        5 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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