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
| Office | Corcoran Country Living |
|---|

