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32 Old Route 199
Red Hook NY 12571 US

$899,000

Active Listing ID 985647
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6 bed
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5.00 Bath (5 Full)
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Lot: 4.00 Acres
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Single Family Residence

$899,000

Active Listing ID 985647
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32 Old Route 199 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.

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Property Features

  • Facts
  • Lot Size: 4.00 Acres
  • Property Type: Residential Multi Family
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 5
  • Cooling System: Wall/Window Unit(s), Window Unit(s)
  • Floor Covering: Combination
  • Heating Fuels: Oil, Forced Air, Electric (Heating)
  • Additional Features
  • Basement
  • Fireplace
  • Pool

School Information

  • School
  • Mill Road-Primary Grades(Elementary)
  • Linden Avenue Middle School(MiddleSchool)
  • Red Hook Senior High School(HighSchool)

Property

  • propertytype: Residential Multi Family
  • propertysubtype: Single Family Residence
  • listprice: 899000
  • unparsedaddress: 32 Old Route 199
  • postalcity: Red Hook
  • stateorprovince: NY
  • country: US
  • postalcode: 12571
  • bathroomsfull: 5
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 4
  • lotsizeunits: Acres
  • lotsizearea: 4
  • livingarea: 0
  • livingareaunits: Square Feet
  • latitude: 41.998551
  • longitude: -73.906096
  • listagentfullname: Jennifer Fivelsdal
  • listagentemail: jennifer@jfivehomes.com
  • listagentkey: 3yd-MLSLINY-70627
  • listagentmlsid: 70627
  • listagentpreferredphone: 8455949947
  • listagentofficephone: 8457586842
  • listofficekey: 3yd-MLSLINY-JFIVRD
  • listofficemlsid: JFIVRD
  • disclaimer: Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
  • sourcesystemid: MLSLINY
  • yearbuilt: 1976
  • listingcontractdate: 2026-04-20
  • listagenturl: http://www.jfivehomes.com
  • countyorparish: Dutchess County
  • parcelnumber: 134889-6172-00-625810-0000.
  • elementaryschool: Mill Road-Primary Grades
  • highschool: Red Hook Senior High School
  • elementaryschooldistrict: Red Hook
  • middleorjuniorschooldistrict: Red Hook
  • highschooldistrict: Red Hook
  • cooling: Wall/Window Unit(s), Window Unit(s)
  • constructionmaterials: Block, Vinyl Siding
  • flooring: Combination
  • heating: Oil, Forced Air, Electric (Heating)
  • numberofunitstotal: 2
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 4
  • parkingfeatures: Driveway
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: First Floor Bedroom, Open Kitchen, Primary Bathroom, Quartz/Quartzite Counters
  • architecturalstyle: Ranch
  • rooms: Bedroom 1, Bedroom 4, Bedroom 5, Bathroom 4, Bedroom 3, Bathroom 5, Bedroom 6, Bathroom 2, Bathroom 1, Bathroom 3, Bedroom 2, Basement
  • otherstructures: Outbuilding
  • utilities: Cable Available
  • basement: Finished, Storage Space, Partially Finished
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -73.9061, 41.99855
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"JFIVE Homes Realty LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"jennifer@jfivehomes.com", "ListBrokerageCity":"Red Hook", "ListBrokerageCountry":"US", "ListBrokerageEmail":"jennifer@jfivehomes.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/104/470271/20240314202638519.png", "ListBrokerageName":"JFIVE Homes Realty LLC", "ListBrokeragePhone":"(845) 758-6842", "ListBrokeragePostalCode":"12571", "ListBrokerageStateOrProvince":null, "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"162 Deer Run Road", "ListBrokerageWebsiteUrl":"http://www.jfivehomes.com", "ListOfficeAddress1":"162 Deer Run Road ", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"JFIVRD", "ListOfficeCity":"Red Hook", "ListOfficeCountry":"US", "ListOfficeEmail":"jennifer@jfivehomes.com", "ListOfficePostalCode":"12571", "ListOfficeStateOrProvince":"NY", "ListPriceCurrencyType":"USD", "ListingTitle":"MULTI_FAMILY - Ranch - Red Hook, NY", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/32-Old-Route-199_Red-Hook_NY_12571_M34359-95696?f=listhub&s=MLSLINY&m=985647&c=rexren", "MLSModificationTimestamp":"2026-04-22 09:03:41", "Neighborhoods":[], "PostalCode":null, "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":11470, "TaxDescription":null, "TaxYear":"2026"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 4/22/2026 9:14:00 AM GMT
Source Updated Date: 4/26/2026 8:22:21 PM GMT

Courtesy of: Jennifer Fivelsdal, JFIVE Homes Realty, LLC, jennifer@jfivehomes.com

Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.