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  • Price cut: $50K (12/3)
    $1,145,000

    76 Smith Road, Preston Hollow, NY 12469

    3beds
    1,684sqft
    Single Family Residence
    Built in 1850
    60 Acres Lot
    $-- Zestimate®
    $680/sqft
    $-- HOA

    What's special

    Two-story barnBrick hearthAbundant natural lightPeriod detailsVintage stoveFront rocking chair porchFarmhouse cabinetry
    Mountain-View Farmhouse Compound on 60 Magical Acres Welcome to 76 Smith Road, a countryside retreat where historic charm meets some of the most beautiful mountain views in the region. Set on 60 private acres, it's a full world of its own with a classic farmhouse, a barn, studio space with guest suite, and a charming one-bedroom cottage tucked nearby. A long, tree-lined driveway creates a dramatic sense of arrival, opening to rolling fields, stone walls, mature maples, overlooking a serene spring-fed half-acre pond, all set against a breathtaking backdrop of wide-open sky and panoramic views. The main house dates back to the 1800s and has been lovingly maintained to preserve its character while offering comfortable modern living. Inside, original hand-hewn beams, hardwood floors, and period details add warmth and authenticity throughout. The living room centers around a cozy wood stove set into a brick hearth, a perfect spot for relaxing or gathering with company. The kitchen radiates country charm with its vintage stove, butcher block counters, and farmhouse cabinetry, while a sunny breakfast nook invites slow mornings overlooking the gardens. Just off the living room is a bright central dining and sitting area, anchored by a stunning floor to ceiling window that frames sweeping mountain views, the ideal setting for entertaining, or simply relaxing with a book and taking in the scenery. Nearby, a smaller first-floor room, currently used as a bedroom, offers flexibility for a home office, library, or guest room. A full bath completes the main level for convenience. Upstairs, three spacious bedrooms offer peaceful treetop vistas and abundant natural light, providing comfortable private space for family or guests. A second full bath can be found on this level. With its southern exposure, the house is flooded with sunlight from dawn to dusk, with nearly every window offering a postcard view of mountains or meadows. Step outside onto the front rocking chair porch or stone patio, ideal for taking in the unobstructed sunrises and sunsets that paint the entire property in gold. Beyond the main residence, a separate studio building offers a spacious 600 sq ft pine-lined recreation room with soaring ceilings, perfect for a game room, art studio, yoga space, or home office - plus an ensuite bedroom upstairs for guests or extended stays. The classic two-story barn provides two horse stalls, equipment storage, and a light-filled studio space, ready for a workshop or studio.. And just down the road, The Green Cottage offers a charming 1-bedroom, 1-bath guest retreat with its own private setting, ideal for visitors or rental potential. The grounds invite endless exploration with its meadows for gardening or animals, open sky for stargazing, and level lawn areas ready for a pool, orchards, or events. Two additional parcels are also available for purchase separately, allowing for expanded privacy, family compound potential, or future development. Located a little over two hours from NYC, 5 minutes to the charming town of Oak Hill, and 20 minutes to the ski slopes at Windham, this property offers a rare blend of history, privacy, and truly unforgettable views that make you never want to leave.
    73 days
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    1,368
    |
    117
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    Zillow last checked: 8 hours ago

    Listing updated: December 13, 2025 at 11:31pm

    Listing by:

    Compass Greater NY, LLC 838-877-8283,

    Leigh Bokser 917-327-4882

    Source: HVCRMLS,MLS#: 20255083MLS Logo

    Tour with a local agent

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 3
    • Bathrooms: 2
    • Full bathrooms: 2
    Heating
    • Forced Air, Hot Water, Oil
    Cooling
    • Ceiling Fan(s), Ductless
    Appliances
    • Included: Water Heater, Washer, Refrigerator, Range, Oven, Microwave, Dryer, Dishwasher
    • Laundry: In Basement
    Features
    • Beamed Ceilings, Eat-in Kitchen, High Speed Internet, Recreation Room
    • Flooring: Hardwood, Linoleum
    • Doors: Storm Door(s)
    • Windows: ENERGY STAR Qualified Windows
    • Basement: Concrete,Unfinished
    • Has fireplace: No
    Interior area
    • Total structure area: 1,684
    • Total interior livable area: 1,684 sqft
    • Finished area above ground: 1,684
    • Finished area below ground: 0

    Property

    Parking
    • Total spaces: 2
    • Parking features: Garage Faces Front, Paved, Driveway
    • Garage spaces: 2
    • Has uncovered spaces: Yes
    Features
    • Levels: Two
    • Stories: 2
    • Patio & porch: Front Porch, Patio
    • Fencing: Partial
    • Has view: Yes
    • View description: Meadow, Mountain(s), Pasture, Pond, Trees/Woods
    • Has water view: Yes
    • Water view: Pond
    Lot
    • Size: 60 Acres
    • Features: Pond on Lot, Cleared, Front Yard, Garden, Gentle Sloping, Landscaped, Level, Many Trees, Meadow, Open Lot, Pasture, Secluded, Subdivide Possible, Views
    Details
    • Additional structures: Barn(s), Garage(s), Guest House, Outbuilding
    • Parcel number: 18111.1
    • Zoning: RR&ag

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Farmhouse
    • Property subtype: Single Family Residence
    Materials
    • Foundation: Stone
    • Roof: Metal
    Condition
    • New construction: No
    • Year built: 1850

    Utilities & green energy

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

    Community & HOA

    Location
    • Region: Preston Hollow

    Financial & listing details

    • Price per square foot: $680/sqft
    • Tax assessed value: $223,900
    • Annual tax amount: $8,530
    • Date on market: 10/15/2025

    Estimated market value

    Not available

    Estimated sales range

    Not available

    $2,530/mo

    Price history

    Price history
    DateEventPrice
    12/3/2025Price change$1,145,000-4.2%$680/sqft
    Source: HVCRMLS #20255083 Report a problem
    10/15/2025Listed for sale$1,195,000-20.3%$710/sqft
    Source: HVCRMLS #20255083 Report a problem
    10/6/2025Listing removed$1,500,000$891/sqft
    Source: HVCRMLS #20251971 Report a problem
    6/5/2025Listed for sale$1,500,000$891/sqft
    Source: HVCRMLS #20251971 Report a problem

    Public tax history

    Public tax history
    Tax history is unavailable.

    BuyAbility℠ payment

    Estimated monthly payment
    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.
    Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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    Climate risks

    Neighborhood: 12469

    Nearby schools

    GreatSchools rating

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