949 Freedom Road, Pleasant Valley, NY 12569

• 6 beds |
• 4 baths

Property Description

Step into a storybook setting with this extraordinary one-of-a-kind property! Featuring TWO homes on 2 picturesque acres: a circa 1900 farmhouse (4 beds/3 full baths - 2,674 sq. ft.) originally built from Sears Roebuck and Co. kit plans and with materials that were delivered by train, AND a second home (2 beds/1bath - 1,080 sq. ft.) ideal for multi-generational living, rental income or guest accommodations. This special property is rich in history, and offers a lifestyle that feels both timeless and full of possibility. The main farmhouse welcomes you with a classic wraparound porch - perfect for morning coffee or quiet evenings under the shade of mature maple trees. Inside, you’ll find 4 bedrooms, 2 flex rooms (perfect for office, den or library) and 3 beautifully renovated full baths, where original craftsmanship meets thoughtful modern updates. Heart pine floors, preserved woodwork, original doors and details and sun-filled spaces create warmth and character throughout. At the heart of the home is a stunning, open kitchen featuring a large center island, quarter sawn white oak cabinetry, Vermont soapstone countertops, a farm sink, gas cooktop, double oven with convection, warming drawer and built in drawer style microwave - designed for gathering, cooking, and making memories. The bedrooms are all generously sized and the spacious primary suite offers a peaceful retreat with a huge walk-in closet and a magazine worthy en-suite bath which includes a 56”x36” walk-in shower and double vanity. A walk-up attic adds incredible storage and future potential. Beyond the main home, the charming second residence (once the farm manager’s house and built in the 1950’s) - offers 2 bedrooms with an additional flex space which would be perfect for home office/gym, etc. Complete with a bright and airy living room, eat-in kitchen, full bath, full unfinished basement and it’s own front porch and patio. Whether for extended family, guests, or income potential, the flexibility is unmatched. Outdoors, the property tells its own story - once part of a 100-acre dairy farm and later a sheep farm, it now features fruit-bearing peach trees, a pear tree (rumored to be over 100 years old), raspberries, blueberries, and even a historic hand-dug well. A massive 54’ x 30’ garage/workshop/garden shed provides endless possibilities for hobbies, storage, or creative pursuits. With updated electric (200-amp service in both homes), generator hookup, and newer roofs (2010 & 2013), the heavy lifting has been done - allowing you to simply enjoy. Just minutes to the Taconic State Parkway, James Baird State Park, The Dutchess Rail Trail, Tops Supermarket, several great restaurants and so much more. This is more than a home - it’s a place to put down roots, create traditions, and be part of a piece of history.

Listing Status:

Active

Data Last Updated:

May 11, 2026 at 7:20AM

Listing Office:

Houlihan Lawrence Inc. : 845-473-9770

MLS ID:

985432

Interior

• General: First Floor Full BathChefs KitchenDouble VanityKitchen IslandNatural WoodworkOpen FloorplanOpen KitchenOriginal DetailsPrimary BathroomStorageWalk-In Closet(s)
• Basement: Unfinished
• A/C: Wall/Window Unit(s)
• Heating: Oil

Exterior

• Style: ColonialFarmhouse
• Other Structures: Garage(s)Guest HouseOutbuildingShed(s)WorkshopPorchWrap AroundPatio
• Parking: DetachedDrivewayGarageParking spaces: 4

Location

• Originating MLS: onekey2
• School District: Arlington
• County: Dutchess County

Lot

• Zoning: 134400-6363-04-926191-0000

Utilities

• Utilities: Electricity Connected
• Water: Well
• Sewer: Septic Tank

Financial

• Source: onekey2