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.
For sale
$649,000
42 Oakes Road, Highland, NY 12528
5beds
4,281sqft
Single Family Residence, Residential
Built in 1800
0.62 Acres Lot
$646,500 Zestimate®
$152/sqft
$-- HOA
What's special
Views are timelessThree-story homeSurrounded by beautiful gardensFilled with characterSubstantial lawnGenerously sized rooms
- 23 hours
- 432
- 34
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Corcoran Country Living 845-338-5832,
Anne C. Rajs 845-338-5832
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1054784
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 5
Heating
- Propane
Cooling
- None
Appliances
- Included: Dishwasher, Dryer, Gas Range, Microwave, Refrigerator, Washer
- Laundry: Washer/Dryer Hookup, Laundry Room
Features
- First Floor Full Bath, Built-in Features, Eat-in Kitchen, Formal Dining, Original Details
- Flooring: Hardwood
- Basement: Unfinished
- Attic: Partial
- Number of fireplaces: 1
- Fireplace features: Living Room
Interior area
- Total structure area: 4,281
- Total interior livable area: 4,281 sqft
Property
Parking
- Total spaces: 4
- Parking features: Driveway
- Has uncovered spaces: Yes
Features
- Levels: Three Or More
- Patio & porch: Deck
- Has view: Yes
- View description: River
- Has water view: Yes
- Water view: River
- Waterfront features: River Front, Waterfront
Lot
- Size: 0.62 Acres
- Features: Front Yard, Garden, Level, Views
Details
- Parcel number: 3200096001
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other
- Property subtype: Single Family Residence, Residential
Materials
- Clapboard
- Foundation: Stone
Condition
- Fixer
- Year built: 1800
- Major remodel year: 1800
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Connected, Electricity Connected, Propane, Water Connected
Community & HOA
HOA
- Has HOA: No
Location
- Region: Lloyd
Financial & listing details
- Price per square foot: $152/sqft
- Tax assessed value: $329,000
- Annual tax amount: $12,455
- Date on market: 9/24/2026
- Cumulative days on market: 1 day
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Estimated market value
$646,500
$614,000 - $679,000
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 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
Monthly payment
Climate risks
Neighborhood: 12528
Nearby schools
Schools provided by the listing agent
- Elementary: Highland Elementary School
- Middle: Highland Middle School
- High: Highland Park Community School
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.





