42 Oakes Road, Highland, NY

$649,000

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5

Beds

5

Baths

4,281

Square feet

62.00

Acres

About 42 Oakes Road

Rarely do you find a property with such an up-close view of the Hudson River, offering a front-row seat to sailboats gliding by, tugboats slowly making their way along the water, and the romantic sound of the train. For generations, this home has stood watch over the Hudson, with a story that appears to reach back more than two centuries. While town records list the home as built in 1900, historical records associated with the property indicate its history may reach back to the early 1800s. Remarkably, the home has been continuously lived in through the generations. Set along the banks of the Hudson, beneath the Walkway Over the Hudson and Mid-Hudson Bridge, this three-story home is filled with character, with generously sized rooms, fireplaces, and a tower offering a remarkable vantage point to watch life on the river go by. Surrounded by beautiful gardens and a substantial lawn, the property offers wonderful outdoor space overlooking the water—a setting that is increasingly hard to find. The home requires substantial renovation, but therein lies the opportunity: to thoughtfully restore its character, honor its history, and bring this Hudson River beauty back to its former glory. The work may be significant, but the setting is irreplaceable and the views are timeless. Franny Reese State Park is just minutes away for hiking and nature, while the train station, New Paltz, and Poughkeepsie are all within easy reach. For the buyer with vision, this is more than a renovation project. It is an opportunity to become part of the continuing story of a remarkable home in an extraordinary Hudson River setting. Property being sold in AS IS condition.

Features of 42 Oakes Road

MLS® # 1054784
Price $649,000
Bedrooms 5
Bathrooms 5.00
Full Baths 5
Square Footage 4,281
Acres 62.00
Year Built 1800
Type Residential
Sub-Type Single Family Residence
Style Other
Status Active

Community Information

Address 42 Oakes Road
City Highland
County Ulster County
State NY
Zip Code 12528

Amenities

Utilities Cable Connected, Electricity Connected, Propane, Water Connected
Parking Spaces 4
Parking Driveway
View River
Is Waterfront Yes
Waterfront River Front
Has Pool No

Interior

Interior Hardwood
Interior Features First Floor Full Bath, Built-in Features, Eat-in Kitchen, Formal Dining, Original Details, Washer/Dryer Hookup
Appliances Dishwasher, Dryer, Gas Range, Microwave, Refrigerator, Washer
Heating Propane
Cooling None
Has Basement Yes
Basement Unfinished
Fireplace Yes
# of Fireplaces 1
Fireplaces Living Room

Exterior

Lot Description Front Yard, Garden, Level, Views, Waterfront
Construction Clapboard

School Information

District Highland
Elementary Highland Elementary School
Middle Highland Middle School
High Highland Park Community School

Additional Information

Date Listed September 24th, 2026
Days on Market 1
Short Sale No
RE / Bank Owned No

Listing Details

OfficeCorcoran Country Living

Listing Map

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