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232 Tally Ho Road
Middletown NY 10940 US

$850,000

Active Listing ID 1032582
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4 bed
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4,522 square feet
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5.00 Bath (4 Full , 1 Half)
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Lot: 17.00 Acres
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Single Family Residence

$850,000

Active Listing ID 1032582
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232 Tally Ho Road A Rare Country Estate Rich in History, Character & Timeless Beauty. Nestled off the road and surrounded by approximately 17 private, wooded acres, this remarkable circa 1820 estate offers an extraordinary opportunity to own a piece of Hudson Valley history. Lovingly expanded over generations while preserving its original character, this one of a kind residence encompasses over 4, 500 square feet of thoughtfully designed living space where historic craftsmanship and modern comfort exist in perfect harmony. From the moment you arrive, the setting is unforgettable. Mature trees, rolling lawns, handcrafted stone walls, beautifully landscaped gardens, and multiple patios create a peaceful retreat where nature becomes part of everyday life. Inside, authentic architectural details celebrate the home's rich heritage. Original woodwork, custom built-ins, exposed beams, hardwood floors, handcrafted moldings, and three fireplaces create warmth and character throughout. Every room offers a unique glimpse into the home's remarkable history while providing comfortable spaces for today's lifestyle. The stunning great room is truly the heart of the home, showcasing reclaimed hand-hewn beams salvaged from a local barn and an impressive floor to ceiling stone fireplace crafted from stone found right on the property. Nearby, an incredible sunroom with soaring wood ceilings, skylights, walls of glass, and beautiful terracotta style flooring invites you to relax while enjoying panoramic views of the surrounding landscape in every season. A thoughtfully designed private wing introduces a distinctive Southwestern-inspired aesthetic, creating an exceptional primary suite complete with a fireplace, spacious ensuite bath, private balcony, and adjoining first-floor living area. Whether used as a luxurious owner's retreat, guest quarters, or a comfortable multi-generational living space, this flexible wing offers endless possibilities while adding a unique architectural dimension to the home. Outside, the property continues to impress. A classic original barn featuring horse stalls, electric service, and an expansive loft provides incredible versatility for equestrian enthusiasts, hobby farmers, livestock, workshops, storage, or future creative pursuits. With acres of wooded privacy and open areas for horses, chickens, goats, gardening, or simply enjoying the outdoors, the possibilities are limited only by your imagination. As an added opportunity, an adjoining 16.7-acre parcel is also available for purchase, allowing the next owner to create an even more extraordinary private estate. Steeped in nearly two centuries of history yet thoughtfully adapted for modern living, this is more than a home it's a legacy property waiting for its next chapter.

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Property Features

  • Facts
  • Lot Size: 17.00 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • 1/2 Bathrooms: 1
  • Cooling System: Attic Fan, Wall/Window Unit(s), Window Unit(s)
  • Exterior Finish: Balcony, Garden, Mailbox
  • Floor Covering: Tile, Carpet, Hardwood
  • Heating Fuels: Oil
  • Additional Features
  • Basement
  • Fireplace
  • Patio

School Information

  • School
  • Minisink Valley Elementary(Elementary)
  • Minisink Valley Middle School(MiddleSchool)
  • Minisink Valley High School(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 850000
  • unparsedaddress: 232 Tally Ho Road
  • postalcity: Middletown
  • stateorprovince: NY
  • country: US
  • postalcode: 10940
  • bathroomsfull: 4
  • bathroomshalf: 1
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 17
  • lotsizeunits: Acres
  • lotsizearea: 17
  • livingarea: 4522
  • livingareaunits: Square Feet
  • latitude: 41.454547
  • longitude: -74.500619
  • listagentfullname: Patricia M Sassi
  • listagentemail: thesassiteam@gmail.com
  • listagentkey: 3yd-MLSLINY-37332
  • listagentmlsid: 37332
  • listagentpreferredphone: 8458003937
  • listagentofficephone: 8458003937
  • listofficekey: 3yd-MLSLINY-BENC03
  • listofficemlsid: BENC03
  • 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: 1820
  • listingcontractdate: 2026-07-31
  • listagentfax: 8455650005
  • listagenturl: http://www.remax-benchmark-ny.com
  • countyorparish: Orange County
  • parcelnumber: 334489-012-000-0001-018.100-0000
  • elementaryschool: Minisink Valley Elementary
  • highschool: Minisink Valley High School
  • elementaryschooldistrict: Minisink Valley
  • middleorjuniorschooldistrict: Minisink Valley
  • highschooldistrict: Minisink Valley
  • appliances: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Washer
  • cooling: Attic Fan, Wall/Window Unit(s), Window Unit(s)
  • constructionmaterials: Aluminum Siding, Vinyl Siding
  • flooring: Tile, Carpet, Hardwood
  • heating: Oil
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 2
  • parkingtotal: 0
  • parkingfeatures: Driveway, Oversize
  • waterfrontyn: False
  • franchiseaffiliation: RE/MAX International
  • interiorfeatures: Eat-in Kitchen, Formal Dining, Natural Woodwork, Original Details, Primary Bathroom, Washer/Dryer Hookup
  • exteriorfeatures: Balcony, Garden, Mailbox
  • windowfeatures: Skylight(s)
  • architecturalstyle: Colonial
  • rooms: Dining Room, Bedroom 3, Bedroom 4, Bathroom 4, Bedroom 1, Bathroom 2, Bathroom 1, Bathroom 5, Basement, Bedroom 2, Bathroom 3
  • utilities: Propane
  • patioandporchfeatures: Patio, Porch
  • basement: Unfinished, Partial, Storage Space
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -74.50062, 41.454548
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"RE/MAX Benchmark Realty Group", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"thesassiteam@gmail.com", "ListBrokerageCity":"New Windsor", "ListBrokerageCountry":"US", "ListBrokerageEmail":"remaxbenchmarkrealty@yahoo.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"RE/MAX Benchmark Realty Group", "ListBrokeragePhone":"(845) 565-0004", "ListBrokeragePostalCode":"12553", "ListBrokerageStateOrProvince":null, "ListBrokerageUnitNumber":"Suite 105", "ListBrokerageUnparsedAddress":"100 Commerce Drive", "ListBrokerageWebsiteUrl":"http://www.remax-benchmark-ny.com", "ListOfficeAddress1":"626 E Main St ", "ListOfficeAddress2":"Suite 105", "ListOfficeBrokerMlsId":"BENC03", "ListOfficeCity":"Middletown", "ListOfficeCountry":"US", "ListOfficeEmail":"benchmarkfrontdesk@gmail.com", "ListOfficePostalCode":"10940", "ListOfficeStateOrProvince":"NY", "ListPriceCurrencyType":"USD", "ListingTitle":"SINGLE_FAMILY - Colonial - Middletown, NY", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/232-Tally-Ho-Rd_Middletown_NY_10940_M35806-51386?f=listhub&s=MLSLINY&m=1032582&c=rexren", "MLSModificationTimestamp":"2026-08-05 04:32:37", "Neighborhoods":[], "PostalCode":null, "RoomCount":12, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":17414, "TaxDescription":null, "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 8/5/2026 5:20:57 AM GMT
Source Updated Date: 8/12/2026 12:47:41 PM GMT

Courtesy of: Patricia M Sassi, RE/MAX Benchmark Realty Group, thesassiteam@gmail.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.