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$899,000
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Property Description
Tucked away at the end of a long, private driveway, yet just a short stroll to the village, Shepard's Knoll offers a rare and compelling combination of seclusion, character, and versatility. Set on four picturesque acres framed by mature trees and vibrant gardens, this distinctive property invites you to enjoy both peaceful retreat and everyday convenience. Originally conceived as a single-family residence, the home has been thoughtfully converted into two spacious units, separated by just one wall, making it simple to return to a grand single-family estate if desired. This flexibility opens the door to a range of possibilities, from multi-generational living to a smart investment opportunity. Unit one features four bedrooms and three bathrooms, along with a finished basement that expands the living space, currently generating steady long-term rental income. Unit two offers two bedrooms and two bathrooms and has a proven track record as a successful Airbnb. Both residences are filled with warmth and charm, each enhanced by a wood-burning fireplace and an additional wood stove, creating an inviting atmosphere. Step outside and the appeal continues. Expansive decks and porches provide the perfect setting for relaxing, entertaining, or simply taking in the serene pastoral views. The grounds are equally impressive, offering a collection of outbuildings that add both function and charm: a quaint cottage ideal for an artist's studio or fitness space, a former sheep barn with abundant storage, chicken coops, and a dedicated area once used for organic vegetable gardening. Whether you envision a private country sanctuary, an income-producing investment, or a flexible living arrangement that evolves with your needs, Shepard's Knoll delivers on every level. With its proven versatility, natural beauty, and prime location, this is more than a property; it's an opportunity to create the lifestyle you've been looking for.
Full Property Details
Full Property Details for 32 Old Rte 199
General
- Price: $899,000
- Taxes: $11,470
- Status: Active
- Type: Multi-Family
- Source: Long_Island
- MLS ID: 985647
- Updated: 4/21/2026
- Added to Site: 29 day(s) ago
Interior
- Interior Features: First Floor Bedroom, Open Kitchen, Primary Bathroom, Quartz/Quartzite Counters
- Fireplace: Yes
- Number of Fireplaces: 2
- Fireplace(s): Living Room, Wood Burning
- Laundry Facilities: Yes
- Flooring: Combination
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 5
Bedrooms
- Total Bedrooms: 6
Other Rooms
- Laundry: In Basement, In Bathroom
Additional Information
- Pool: Yes
- Private Pool: Yes
Parking
- Total Spaces: 4
- Parking Features: Driveway
Location
- County: Dutchess County
- Driving Directions: Route 9 South to right on West Market Street, left on Old Route 199. The house is on the left.
School Information
- High School District: Red Hook
- Elementary School: Mill Road-Primary Grades
- Middle School: Linden Avenue Middle School
- High School: Red Hook Senior High School
Heating & Cooling
- Cooling Type: Wall/Window Unit(s)
- Heating Type: Electric, Forced Air, Oil
Utilities
- Sewer: Septic Tank
- Water: Well
- Utility Description: Cable Available, Electricity Connected, Trash Collection Private
Structural Information
- Architectural Style: Ranch
- Detached/Attached: Attached
- Construction: Block, Vinyl Siding
- Basement: Yes
- Basement Desc.: Finished, Partially Finished, Storage Space
- Year Built: 1976
Additional Structures
- Other Structures: Barn(s), Outbuilding
Lot Features
- Lot Size (Acres): 4
- Fence: Yes
- Fencing (Description): Partial
Financial Considerations
- Tax Amount: $11,470
Disclosures and Reports
- Special Conditions: None
- Property ID: 134889-6172-00-625810-0000.
Listed by JFIVE Homes Realty, LLC
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Schools
Schools serving 32 Old Rte 199
School District:Red Hook Central School District
| Name | Grades | Distance |
|---|---|---|
Mill Road Intermediate Grades 9 Mill Road, Red Hook, NY 12571 | 3-5 | 2.3 mi |
Mill Road Primary Grades 9 Mill Road, Red Hook, NY 12571 | PK-2 | 2.3 mi |
Linden Avenue Middle School 65 West Market Street, Red Hook, NY 12571 | 6-8 | 1.3 mi |
Red Hook Senior High School 103 West Market Street, Red Hook, NY 12571 | 9-12 | 1.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 32 Old Rte 199
Date
Details
Price
Change
Source
4/21/2026
Listed
$899,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 32 Old Rte 199
Year
Property Taxes
Change
Tax Assessment
Change
2025
$2,522
—
$131,200
9%
2025
$2,522
-8%
$120,400
14%
2020
$2,727
359%
$105,600
11%
2021
$594
-78%
$95,100
—
2020
$2,727
1%
$95,100
—
2018
$2,689
1%
$95,100
—
2017
$2,665
1%
$95,100
—
2016
$2,642
-1%
$95,100
—
2015
$2,656
1%
$95,100
—
2015
$2,620
3%
$95,100
—
2013
$2,534
—
$95,100
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 32 Old Rte 199
32 Old Route 199, Red Hook, NY 12571 (MLS# 985647) is a Multi-Family property with 2 units containing 6 bedrooms and 5 full bathrooms. 32 Old Route 199 is currently listed for $899,000 and was received on April 21, 2026. Want to learn more about 32 Old Route 199? Do you have questions about finding other Multi-Family real estate for sale in Red Hook? You can browse all Red Hook real estate or contact a Coldwell Banker agent to request more information.
