Nicholas Falcone
Licensed Real Estate Salesperson
REALTOR®
Stamford, NY
Office: (607) 652-2220 (631) 384-1507

76 Smith Road, Preston Hollow, NY 12469

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Property Description

Mountain-View Farmhouse Compound on 60 Magical AcresWelcome 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, its 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.

76 Smith Road | MLS# 20255083

This single family home located at 76 Smith Road, Preston Hollow, NY 12469 is currently listed for sale with an asking price of $1,095,000. This property was built in 1850 and has 3 bedrooms and 2 full baths with 1684 sq. ft. Smith Road is located within the Greenville School District school district. Search Preston Hollow real estate on nicholas-falcone.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Cooling: Ceiling Fan(s), Ductless
Fuel Type: Oil
Garage: 2
Heating: Forced Air, Hot Water, Oil
Home Style: Farmhouse
Lot Size: 60.00 Acres
Roof Type: Metal
Stories: 2.0
Taxes: $8,530
Year Built: 1850

Amenities

Beamed Ceilings
Eat-in Kitchen
High Speed Internet
Recreation Room

Feature Descriptions

Appliances: Water Heater, Washer, Refrigerator, Range, Oven, Microwave, Dryer, Dishwasher
Days on Site: 139
Flooring: Hardwood, Linoleum
Laundry: In Basement
Lot: Pond on Lot, Cleared, Front Yard, Garden, Gentle Sloping, Landscaped, Level, Many Trees, Meadow, Open Lot, Pasture, Secluded, Subdivide Possible, Views
Parcel #: 181-1-1.1
Parking: Garage Faces Front, Paved, Driveway
Patio/Porch: Front Porch, Patio
Road Frontage: County Road
Sewer: Septic Tank
SQFT Total: 1684
Water: Well

Local Schools

School District: Greenville School District

Estimate Your Payment

Estimated Payment

$ 3,467.20 per month $2,437.00 Principal & Interest $710.83 Property Tax $319.38 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: Compass Greater NY, LLC

Shown By

Agent Name: Nicholas Falcone
Agent Phone: (631) 384-1507
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 03/03/2026. The listing information on this page last changed on 03/03/2026. 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 Tue 03/03/2026 1:11:38 AM EST) or Global MLS (last updated Tue 03/03/2026 1:06:55 AM EST) or New York State Alliance MLS (last updated Tue 03/03/2026 1:10:29 AM EST) or Hudson Valley Catskill Region MLS (last updated Tue 03/03/2026 12:11:14 AM EST) or OneKey MLS (last updated Tue 03/03/2026 1:10:05 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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