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Property at 32 Old Route 199, Red Hook, NY 12571
ACTIVE
0
$899,000

32 Old Route 199Red Hook, NY, 12571

6 Beds6 Baths3,500 SqFt4 Acres
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, Shepherd'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 / 40

Est. Monthly

$4,261/MO

$899,000

32 Old Route 199, Red Hook, NY

6 Beds6 Baths3,500 SqFt4 Acres

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, Shepherd'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.

StatusActive
Property TypeResidential Income
Property Subtype—
Year Built1976
Total Rooms12 rooms
Days on Market51 days

Est. Monthly Payment

$4,261.24

%
%
yr

Private Mortgage Insurance

Not required

Affordability Checkoptional
$

Enter your annual income to check affordability

Property Details

Property Information

32 Old Route 199

Red Hook, NY 12571 • Dutchess
6
Beds
6
Baths
3,500
SqFt
4
Acres
Status
Active
Property Type
Residential Income
Property Subtype
—
Year Built
197650 years ago
Total Rooms
12 rooms
Days on Market
51 days
Tax History
Estimated values, may not reflect current amounts.
  • Annual Tax Amount
    $11,470
Property History
  • Listed for sale
    Apr 21, 2026 • NY State MLS • 11715926
    $899,000
Mortgage Calculator
Estimated monthly payment for this property
$4,261.24
Down Payment
Interest Rate
Loan Term
%
%
yearsyrs.
Affordability Checkoptional
$

Enter your annual income to see if this home fits your budget

Private Mortgage Insurance

Not required — down payment above 20%
MLS Information
  • Source
    NY State MLS
  • MLS#
    11715926
  • Listing Office
    JFIVE HOMES REALTY LLC
  • Last Updated
    7 days ago

Climate & Systems

  • Heating
    • Forced Air
    • Oil

Interior Features

  • Basement
    Kitchen
  • Interior Features
    Master Downstairs

Lot & Grounds

  • Lot Size
    4 acres

Type

  • Property Type
    Residential Income

Condition

  • Year Built
    1976
  • Days on Market
    51 days
  • Water
    None
  • Sewer
    None

607-282-6242, (607) 282-6242, or +1 607 282 6242

Kevin Lucero

Kevin Lucero

Lic. Real Estate Salesperson

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