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5 Beds
5 Baths
4,281 sqft

$627,000

42 Oakes Road, Highland NY, 12528

Price per sqft$146.46
Built in1800
Property size4,281 sqft
Property typeResidential

Overview

Active

Listed Sep 26, 2026

Updated 18 min ago

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, original details and a fourth floor 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.

$4,171/mo

Est. mortgage payment based on a $627,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
20265699

Interior Features

Bedrooms
5
Bathrooms
5
Fireplace
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.62 Acres

Other Property Details

Taxes
$12,455
Tax Frequency
Annually
View
Yes
Waterfront
Yes
55+/Senior Community
No

Also listed on OneKey MLS / Hudson Gateway and Long Island MLS

MLS provider logo

Listed by Anne Rajs with Corcoran Country Living
Listing Contact:  

The IDX display contains information sourced from the Hudson Valley Catskill Region MLS as of 10/19/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Hudson Valley Catskill Region MLS all rights reserved.

Data last updated on 10/19/2026 at 2:46 PM UTC

 

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