32 Old Rte 199

Red Hook, NY 12571

$899,000
Price
6
Beds
3,500 Sq. Ft.
$257 / Sq. Ft.
3,500
Sq. Ft.
$257
per Sq. Ft.
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Front of house- Unit 1
back of house
Front-Unit 2
Dining area - another view
Kitchen
Kitchen - a second view
living room
LR seen from kitchen
LR second view
office with view of the backyard
office - second view
Door to expansive deck -
Primary BR
Primary BA
_Primary BA G
Cottage along Driveway
Cottage could be a studio
Trees
exterior back
Kitcchen 4 BR unit
LR 4 Br Unit
Dr - in 4 Br unit
BR 2 - 4 BR unit
Bathroom
BR Primary - 4 Br unit
Bathroom Apt - Copy
Basement area
Basement Sitting area
Basement Bar
Basement library area
Dining area - open floor plan

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,...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.
  1. Listed by Jennifer Fivelsdal • JFive Homes Realty,LLC
    P: (845)-594-9947 C: (845)-594-9947 jennifer@jfivehomes.com

Property Details for 32 Old Rte 199

Senior Community YN
No
Zoning
RD3
Senior Community YN
No
LISTING UPDATED: 04/22/2026 11:02 AM

Property Details for 32 Old Rte 199

StatusActive
MLS #20261774
Days on Market2
Taxes$11,469 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeMulti Family
MLS TypeResidential Income / Duplex
Year Built1976
Lot Size4.00 AC / 174,240 SF
CountyDutchess County
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Location

Listing Courtesy of JFive Homes Realty,LLC
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Building Information for 32 Old Rte 199

Stories1Residences2Year Built1976Building Size-Lot Size4.00 AC / 174,240 SF

Payment Calculator

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$5,483 per month

30 year fixed, 6.46% Interest

Principal and Interest

$4,527

Property Taxes

$956

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 32 Old Rte 199

Summary
Location and General Information
  • Directions: Kingston Rhinecliff Bridge to left on Rte 9G. Just before light, make a right on Old Route 199,
  • Township: Red Hook
  • MLS Area Major: Red Hook
  • County: Dutchess
  • Latitude: 41.998061
  • Longitude: -73.905997
  • MLS Area Major: Red Hook
  • Sign On Property YN: Yes
Taxes and HOA
  • Association Fee: $.00
  • Parcel Number: 134889-6172-00-625810-000
  • Tax Block: 7200
  • Tax Annual Amount: $11,469.00
School Information
  • Elementary School: Mill Road - Intermediate Grades
Property
Lot Information
  • New Construction YN: No
  • Lot Size Acres: 4.0
  • Above Grade Finished Area: 3500.0
  • Below Grade Finished Area: 1400.0
  • Living Area: 3500.0
  • Lot Size Area: 4.0
  • Lot Size Units: Acres
  • Lot Size Square Feet: 174240.0
  • Above Grade Finished Area: 3500.0
  • Below Grade Finished Area: 1400.0
  • Lot Size Acres: 4.0
  • Ranch: Yes
  • Duplex: Yes
Property and Assessments
  • Owner Name: Dunckley
  • Total Floor Plans Count: 0
  • Property Type: Residential Income
  • Year Built: 1976
  • Property Sub Type: Duplex
  • New Construction YN: No
  • Page: 5654
  • Section: 617
Taxes and HOA
  • Tax Assessed Value: 620000.0
  • Tax Lot: 6258
Utilities
  • Electric: Yes
  • Cable Available: Yes
  • Electricity Connected: Yes
  • Well: Yes
Interior and Exterior Features
Exterior Features
  • Stories: 1
Interior Features
  • Fireplaces Total: 2
  • Fireplace YN: Yes
  • Bathrooms Total (Integer): 5
  • Bathrooms Total (Decimal): 5.0
  • Bathrooms Total (Notational): 5.0
  • Cooling: Yes
  • Heating: Yes
  • Bedrooms Total: 6
  • Fireplace YN: Yes
  • Units Furnished: All Units
  • Built-In Electric Range: Yes
  • Dishwasher: Yes
  • Dryer: Yes
  • Electric Oven: Yes
  • Washer: Yes
  • Window Unit(s): Yes
  • Living Room: Yes
  • Forced Air: Yes
  • Oil: Yes
Multi Family
Multi Family Information
  • Units Furnished: All Units
  • Number of Units: 2
Mobile Home
Mobile Home Information
  • Sign On Property YN: Yes
Rental
Rental Information
  • Occupant Name: *** NEW LISTING ***
  • Occupant Name: *** NEW LISTING ***

Public Records for 32 Old Rte 199

Taxable ValueLand$172,400Additions$447,600Total$620,000
Tax Record2024$11,107 ($926 / month)
Home Facts
Baths2.5Total Finished SqFt3,320 SqFtAbove Grade Finished SqFt1,720 SqFtFinished Basement SqFt1,600 SqFtStories1Lot Size174,240 SqFtStyleDuplexYear Built1976Year Renovated2000ZoningRD3CountyDUTCHESSAPN134889 6172-00-625810-0000Fireplace TypeHas Fireplace

Schools near 32 Old Rte 199

This home is within Red Hook Central School District.
Rating
School
Type
Grades
Distance
Mill Road Primary Grades
Public - PK to 2
Mill Road Intermediate Grades
Public - PK to 5
Linden Avenue Middle School
Public - 6 to 9
Red Hook Senior High School
Public - 9 to 12
Rating
School
Distance
Mill Road Primary Grades
PublicPK to 2

Mill Road Intermediate Grades
PublicPK to 5

Linden Avenue Middle School
Public6 to 9

Red Hook Senior High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 32 Old Rte 199, Red Hook, NY 12571

32 Old Rte 199 is a multi-family home for sale in Red Hook, NY 12571. This property was listed for sale on April 22, 2026 by JFive Homes Realty,LLC, it's currently listed at $899,000. This listing's school district is Red Hook Central School District. Nearby schools include Mill Road Primary Grades, Mill Road Intermediate Grades and Linden Avenue Middle School. 32 Old Rte 199 is a 6-bed, 5-bath, 3,500 sqft multi-family home built in 1976.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of JFive Homes Realty,LLC

The source of the displayed data is either the property owner or public record provided by non-governmental third parties. It is believed to be reliable but not guaranteed. This information is provided exclusively for consumers’ personal, non-commercial use. The data relating to real estate for sale or lease on this webpage comes from the the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. Real estate listings held by brokerage firms other than Compass are marked with a OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS or Ulster County Board of REALTORS Logo. Use of these search facilities other than by a consumer seeking to purchase or lease real estate is prohibited. The accuracy of all information is deemed reliable but not guaranteed and should be verified through personal inspection by and/or with appropriate professionals. The data contained herein is copyrighted by the IDX Program of OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS and is protected by all applicable copyright laws. Any unauthorized dissemination of this information is in violation of copyright laws and is strictly prohibited. Information Copyright 2026, OneKey® MLS, Columbia Greene Northern Dutchess MLS, Hudson Valley Catskill Regional MLS and Ulster County Board of REALTORS. All rights reserved. Data last updated: 04/22/2026 11:02 AM