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265 Oakland Valley Road
Cuddebackville NY 12729 US

$329,000

Pending Listing ID 908709
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3 bed
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2.00 Bath (2 Full)
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Lot: 2.30 Acres
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Duplex

$329,000

Pending Listing ID 908709
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265 Oakland Valley Road One Property. Two Homes. Unlimited Possibilities. Welcome to 265 Oakland Valley Road...a nature lover’s dream with a unique bonus you don’t find every day: two homes on one property! Set on over 2 peaceful acres, this unique offering includes a charming main residence and a picture-perfect brookside cottage, perfect for rental income, multi-generational living, guests, or your own private retreat. The main home is warm and inviting, featuring two bedrooms and a bonus room, one bath, and an eat-in kitchen on the main level (720 sq. ft.). Downstairs, you’ll find a cozy living room (an additional 320 sq. ft) with sliding glass doors leading to a quaint patio overlooking the expansive backyard where you can sip your morning coffee and listen to the birds sing. You will also find an above-ground pool for summer fun and fruit trees, such as apple, peach & pear that adorn the property! Wander across the lawn and discover the sweetest surprise: a legal one-bedroom cottage (640 sq. ft) that sits alongside a babbling brook that echoes the sounds of tranquility right outside the sliding glass doors. Whether you're envisioning a guest retreat, multi-generational living, a rental opportunity, or a peaceful place to write your next chapter, this cottage has endless charm and potential. And there’s more...a rustic shed with a covered porch creates yet another outdoor oasis, and a private trail winds along the back of the property, following the brook, and inviting you to slow down and soak in the beauty of your surroundings. A property with two separate living quarters and natural serenity doesn’t come along often, so this one is definitely worth the look and will definitely charm you! Whether your are looking for two rental incomes or to live in one home and rent out the other - so many possibilities! 90 miles from NYC, easy access to the train (NJ Transit/Otisville), close to all of the area's attractions such as The Forestburgh Playhouse, Bethel Woods, Resorts World Casino, The Kartrite Waterpark, Delaware River Rafting and so much more!

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Property Features

  • Facts
  • Lot Size: 2.30 Acres
  • Property Type: Residential Multi Family
  • Property Sub-type: Duplex
  • Features
  • Full Bathrooms: 2
  • Cooling System: Ductless
  • Exterior Finish: Waterfront, Pool
  • Heating Fuels: Fireplace(s), Oil, Propane (Heating)
  • Additional Features
  • Fireplace
  • Pool
  • Waterfront

School Information

  • School
  • N A Hamilton Bicentennial School(Elementary)
  • Port Jervis Middle School(MiddleSchool)
  • Port Jervis Senior High School(HighSchool)

Property

  • propertytype: Residential Multi Family
  • propertysubtype: Duplex
  • listprice: 329000
  • unparsedaddress: 265 Oakland Valley Road
  • postalcity: Cuddebackville
  • stateorprovince: NY
  • country: US
  • postalcode: 12729
  • bathroomsfull: 2
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 2.3
  • lotsizeunits: Acres
  • lotsizearea: 2.3
  • livingarea: 1680
  • livingareaunits: Square Feet
  • listagentfullname: Dominick J Tufano
  • listagentemail: dominicktufano@gmail.com
  • listagentkey: 3yd-MLSLINY-37420
  • listagentmlsid: 37420
  • listagentpreferredphone: 9144437622
  • listagentofficephone: 8453410004
  • listofficekey: 3yd-MLSLINY-BENC03
  • listagentstatelicense: 10301201924
  • listofficemlsid: BENC03
  • disclaimer: Copyright © 2025 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: 1940
  • listingcontractdate: 2025-09-04
  • listagenturl: http://www.remax-benchmark-ny.com
  • countyorparish: Orange County
  • parcelnumber: 332800-020-000-0001-064.110-0000
  • elementaryschool: N A Hamilton Bicentennial School
  • highschool: Port Jervis Senior High School
  • elementaryschooldistrict: Port Jervis
  • middleorjuniorschooldistrict: Port Jervis
  • highschooldistrict: Port Jervis
  • cooling: Ductless
  • constructionmaterials: Frame
  • heating: Fireplace(s), Oil, Propane (Heating)
  • numberofunitstotal: 2
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Driveway
  • waterfrontyn: True
  • franchiseaffiliation: RE/MAX International
  • interiorfeatures: First Floor Bedroom, First Floor Full Bath, Eat-in Kitchen
  • exteriorfeatures: Waterfront, Pool
  • waterfrontfeatures: Stream, Waterfront
  • architecturalstyle: Bungalow
  • rooms: Basement, Bathroom 1, Bathroom 2, Bedroom 1, Bedroom 2, Bedroom 3
  • dock: False
  • poolprivateyn: True
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"RE/MAX Benchmark Realty Group", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"dominicktufano@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":"NY", "ListBrokerageUnitNumber":"Suite 105", "ListBrokerageUnparsedAddress":"100 Commerce Drive", "ListBrokerageWebsiteUrl":"http://www.remax-benchmark-ny.com", "ListOfficeAddress1":"626 E Main St", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"39166", "ListOfficeCity":"Middletown", "ListOfficeCountry":"US", "ListOfficeEmail":"benchmarkfrontdesk@gmail.com", "ListOfficePostalCode":"10940", "ListOfficeStateOrProvince":"NY", "ListPriceCurrencyType":"USD", "ListingTitle":"Bungalow, Cottage, Duplex - Cuddebackville, NY", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/265-Oakland-Valley-Rd_Cuddebackville_NY_12729_M30785-19407?f=listhub&s=MLSLINY&m=908709&c=rexren", "MLSModificationTimestamp":"2025-10-14T15:56:36Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Duplex", "RawPropertyType":"Residential Income", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":4280.47, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/14/2025 10:07:39 PM GMT
Source Updated Date: 12/5/2025 12:40:34 PM GMT

Courtesy of: Dominick J Tufano, RE/MAX Benchmark Realty Group, dominicktufano@gmail.com

Copyright © 2025 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.