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42 Oakes Road

Highland, NY 12528 · Ulster County

Beds
5
Baths
5
Sqft
4,281
Status
Active
On site
39 days

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About this home

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.

Listed with Corcoran Country Living · Anne C. Rajs · Source: OneKey MLS

One Key MLS

Information provided by One Key MLS, and is deemed reliable but not guaranteed accurate. Data last updated: Nov 2, 2026, 1:08 PM ET. ©2026 One Key MLS.

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Estimate your mortgage payment, including the principal and interest, taxes, insurance, HOA, and private mortgage insurance.

$4,434.72Total / mo

Estimated monthly payment

Principal & interest
$3,196.80(72.1%)
Taxes
$1,037.92(23.4%)
Insurance
$200.00(4.5%)

Representative rates

Representative rates only, indicative for comparison. Edit the interest rate for your own quote; your lender’s numbers vary with credit, points, and insurance.

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Market insights

The market around Highland, NY

Current listings

New in the last 30 days

13

Nov 2026

Average price

Active listings

$591,292

Nov 2026

Average days on market

Active listings

148 days

Nov 2026

Computed from 92 active OneKey MLS listings in Highland, NY.

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