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.
Active
Price cut: $59K (11/6)
$568,000
42 Oakes Road, Highland, NY 12528
5beds
4,281sqft
Single Family Residence
Built in 1800
0.62 Acres Lot
$562,000 Zestimate®
$133/sqft
$-- HOA
What's special
Original detailsViews are timelessThree-story homeSurrounded by beautiful gardensSubstantial lawnGenerously sized rooms
- 45 days
- 18,025
- 380
Zillow last checked:
Listing updated:
Listed by:
Corcoran Country Living 845-876-6676,
Anne Rajs 845-797-1034
Source: HVCRMLS,MLS#: 20265699
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 5
Heating
- Propane, Zoned
Appliances
- Included: Washer, Refrigerator, Range, Microwave, Dryer, Dishwasher
- Laundry: Laundry Room, Upper Level
Features
- Built-in Features, Eat-in Kitchen, High Ceilings
- Flooring: Wood
- Basement: Unfinished
- Number of fireplaces: 1
- Fireplace features: Metal
Interior area
- Total structure area: 4,281
- Total interior livable area: 4,281 sqft
- Finished area above ground: 4,281
- Finished area below ground: 0
Property
Features
- Stories: 3
- Patio & porch: Deck
- Exterior features: Garden, Private Yard
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Body of water: Hudson River
- Frontage type: River
Lot
- Size: 0.62 Acres
- Features: Garden
Details
- Parcel number: 961
- Zoning: R-2
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other
- Property subtype: Single Family Residence
Materials
- Frame
- Foundation: Stone
Condition
- Fixer
- New construction: No
- Year built: 1800
Utilities & green energy
- Electric: 200+ Amp Service
- Sewer: Private Sewer
- Water: Well
- Utilities for property: Cable Connected, Electricity Available, Sewer Connected, Water Available
Community & HOA
HOA
- Has HOA: No
Location
- Region: Lloyd
Financial & listing details
- Price per square foot: $133/sqft
- Tax assessed value: $329,000
- Annual tax amount: $12,455
- Date on market: 9/25/2026
- Listing terms: Cash
- Electric utility on property: Yes
- Road surface type: Asphalt
Estimated market value
$562,000
$534,000 - $590,000
$7,003/mo
Price history
| Date | Event | Price |
|---|---|---|
| 11/6/2026 | Price change | $568,000-9.4%$133/sqft |
Source: | ||
| 10/19/2026 | Price change | $627,000-3.4%$146/sqft |
Source: | ||
| 9/24/2026 | Listed for sale | $649,000+158.6%$152/sqft |
Source: | ||
| 12/6/2006 | Sold | $251,000$59/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $329,000 |
| 2024 | -- | $329,000 |
| 2023 | -- | $329,000 |
| 2022 | -- | $329,000 |
| 2021 | -- | $329,000 |
| 2020 | -- | $329,000 |
| 2019 | -- | $329,000 |
| 2018 | -- | $329,000 |
| 2017 | $10,981 | $329,000 |
| 2016 | -- | $329,000 |
| 2015 | -- | $329,000 |
| 2014 | -- | $329,000 |
| 2013 | -- | $329,000 |
| 2011 | -- | $329,000 -6% |
| 2010 | -- | $350,000 +40% |
| 2009 | -- | $250,000 |
| 2008 | -- | $250,000 |
| 2007 | -- | $250,000 |
| 2006 | -- | $250,000 +27% |
| 2005 | -- | $196,800 |
| 2004 | -- | $196,800 |
| 2003 | -- | $196,800 +19.9% |
| 2002 | -- | $164,200 |
| 2001 | -- | $164,200 |
| 2000 | -- | $164,200 |
Find assessor info on the county website





