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    1 home
      1 home available
      265 Oakland Valley Road, Cuddebackville, NY 12729
      Pending
      265 Oakland Valley Road, Cuddebackville, NY 12729
      $329,000
      2beds
      1bath
      720sqft
      2.3acres
      House for Sale
      Down payment assistanceDown Payment Help

      265 Oakland Valley Road, Cuddebackville, NY 12729

      Listing by: RE/MAX Benchmark Realty Group
      1 - 1 of 1 results
      Copyright © 2025 OneKey® MLS LLC
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
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      OneKey® MLS
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      265 Oakland Valley Road, Cuddebackville, NY 12729
      Pending
      $329,000
      Down payment assistanceDown Payment Help
      2beds
      1full,half bath
      720sqft
      2.3acres

      265 Oakland Valley Road, Cuddebackville, NY 12729

      City/Town:Cuddebackville   Post Office: Cuddebackville     

      House for Sale by Dominick J TufanoRE/MAX Benchmark Realty Group.

      Data checked -. Listing last updated 51 days ago.
      1. Overview
      2. Details
      3. More 

      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: a second home on the 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, 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! 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!

      Internet Serviceability
      Details
        Property type
      Residential
        Year built
      1940
        Heating
      Oil, Propane
        Cooling
      Ductless
        Total rooms
      4
        Garage
      No
        City/Town
      Cuddebackville
        Post Office
      Cuddebackville
        Parking spots
      -
      897085
      MLS ID
      Pending
      Status
      08/08/2025
      On Market Date
        Laundry features
      In Basement
        Flooring
        Fireplace
      Yes
        Pets allowed
        Architectural Style
      Bungalow, Cottage
        Basement
      Partially Finished, Walk-Out Access
        View
      Interior features
      First Floor Bedroom, First Floor Full Bath, Eat-in Kitchen
      Exterior features
      Lot features
      Waterfront
      Appliances included
      Dishwasher, Dryer, Microwave, Other, Oven, Refrigerator
      Construction materials
      Frame, T111
      Monthly taxes
      $357
      Yearly taxes
      $4,280.47
      Community Features
      -
      School district
      Port Jervis
      Schools
      N A Hamilton Bicentennial School, Port Jervis Middle School, Port Jervis Senior High School
      Senior community
      No
      Common Charges
      -
      Maintenance
      -
      Additional Fees
      -
      Open Houses
      In-Person
      No upcoming in-person open houses
      Virtual
      No upcoming virtual open houses
      Contact Agent
      Listing By:
      Dominick J Tufano
      Dominick J Tufano
      Amy Skellett
      Amy Skellett
      Dominick J Tufano
      Dominick J Tufano
      Associate Real Estate Broker, RE/MAX Benchmark Realty Group
      Direct Number 
       
      Amy Skellett
      Amy Skellett
      Real Estate Salesperson, RE/MAX Benchmark Realty Group
      Direct Number 
       
      Location
      GPS Navigable
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      265 Oakland Valley Road, Cuddebackville, NY 12729, is a 2 bedroom, 1 bathroom, 720 sqft. Single Family Residence built in 1940. This property is currently available for sale and was listed on OneKey® MLS on 8-8-2025. The MLS# for this Single Family Residence is MLS# 897085.
      Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
      Copyright ©2025