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Jill A. Lehmann
Associate Real Estate Broker
REALTOR®
(607) 267-0313 Cell
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42 Oakes Road, Highland, NY 12528

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Property Description

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.

42 Oakes Road | MLS# 20265699

This single family home located at 42 Oakes Road, Highland, NY 12528 is currently listed for sale with an asking price of $649,000. This property was built in 1800 and has 5 bedrooms and 5 full baths with 4281 sq. ft. Oakes Road is located within the Highland Central Schools school district. Search Highland real estate on jill-ogden.timberlandproperties.com today.

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Property Features

Property Type: Residential - Single Family
Basement: Yes
Fireplaces: 1
Fuel Type: Propane
Heating: Propane, Zoned
Home Style: Other
Lot Size: 0.62 Acres
Taxes: $12,455
Year Built: 1800

Amenities

Built-in Features
Eat-in Kitchen
High Ceilings
Garden
Private Yard

Feature Descriptions

Appliances: Washer, Refrigerator, Range, Microwave, Dryer, Dishwasher
Days on Site: 15
Exterior: Frame
Fireplace: Metal
Flooring: Wood
Laundry: Laundry Room, Upper Level
Lot: Garden
Parcel #: 96-1
Patio/Porch: Deck
Road Surface: Asphalt
Sewer: Private Sewer
SQFT Total: 4281
Utilities: Cable Connected, Electricity Available, Sewer Connected, Water Available
Water: Well

Local Schools

School District: Highland Central Schools

Estimate Your Payment

Estimated Payment

$ 2,671.60 per month $1,444.39 Principal & Interest $1,037.92 Property Tax $189.29 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Corcoran Country Living

Shown By

Agent Name: Jill A. Lehmann
Agent Phone: (607) 267-0313 Cell
Agency Title: Timberland Properties

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All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless. Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 10/11/2026. The listing information on this page last changed on 10/11/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 10/11/2026 5:16:02 AM EST) or Global MLS (last updated Sun 10/11/2026 1:22:21 AM EST) or New York State Alliance MLS (last updated Sun 10/11/2026 2:34:55 AM EST) or Hudson Valley Catskill Region MLS (last updated Sun 10/11/2026 12:11:17 AM EST) or OneKey MLS (last updated Sun 10/11/2026 1:45:15 AM EST). Real estate listings held by brokerage firms other than Timberland Properties may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

All information is deemed reliable but not guaranteed. All properties are subject to prior sale, change, or withdrawal. Neither broker(s), nor agent(s) shall be responsible for any typographical errors, misinformation, or misprints, and shall be held totally harmless.

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