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42 Oakes Road, 
Highland, NY 12528

$649,000


5

Beds


5

Baths


4,281

Sq Ft


Single Family

Active

Listed by

Anne C. Rajs

Corcoran Country Living

Last updated:

October 28, 2026, 12:02 PM

MLS#

1054784

Source:

OneKey MLS

About This Home

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.

Home Facts

Single Family

5 Baths

5 Bedrooms

Built in 1800

Price Summary

649,000

$151 per Sq. Ft.

MLS #:

1054784

Last Updated:

October 28, 2026, 12:02 PM

Added:

a month ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

5

Full Bathrooms:

5

Interior

Living Area:

4,281 Sq. Ft.


Structure

Structure

Building Area:

4,281 Sq. Ft.

Year Built:

1800


Lot

Lot Size (Sq. Ft):

27,007


Finances & Disclosures

Finances

Price:

$649,000

Price per Sq. Ft:

$151 per Sq. Ft.

Source:OneKey MLS
Copyright 2026 OneKey MLS. All rights reserved. Listings courtesy of OneKey MLS as distributed by MLS GRID . OneKey MLS provides content displayed here (“provided content”) on an “as is” basis and makes no representations or warranties regarding the provided content, including, but not limited to those of non-infringement, timeliness, accuracy, or completeness. Individuals and companies using information presented are responsible for verification and validation of information they utilize and present to their customers and clients. OneKey MLS will not be liable for any damage or loss resulting from use of the provided content or the products available through Portals, IDX, VOW, and/or Syndication. Recipients of this information shall not resell, redistribute, reproduce, modify, or otherwise copy any portion thereof without the expressed written consent of OneKey MLS.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.