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Sold for $385,000 on 12/18/25
  • $385,000

    256 Pleasant Valley Road, Callicoon, NY 12723

    2beds
    1,010sqft
    Single Family Residence, Residential
    Built in 1960
    3 Acres Lot
    $385,000 Zestimate®
    $381/sqft
    $2,119 Estimated rent

    Home value

    $385,000

    $339,000 - $439,000

    $2,119/mo

    Zestimate® history
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    What's special

    Set well back from a picturesque country road on a wooded hillside, Pleasant Valley is a 2 bed, 2 bath, turnkey escape. Enjoy three acres of solitude, split between a level clearing of yard and mature trees for a fully ensconced feel - Pleasant Valley certainly provides the privacy you are seeking with your country home. The striking sun room is a welcome entry point to the home - full of character and light, and currently in use as an additional dining space. Once inside the house proper, you’ll find a cozy living and dining room, centered around a wood-burning stove for full Catskills cabin vibes. The kitchen is easy breezy with plenty of below counter storage, open shelving, and an efficient use of space. Like everything in this home, the footprint is compact but highly functional with plenty of charm throughout. One of the highlights of the home is certainly the primary bedroom. Where the rest of the house is very considerate in its spacing and sizing, the primary is generous in scale (plenty of room for a King bed) and features a large soaking tub at the foot of the room. This is the kind of place you’ll always looking forward to waking up to - no matter what the weather might look like. A large attached bathroom really drives home the “suite” like feel of the primary bedroom. The comfortable second bedroom offers its own stylishly appointed bathroom with stall shower. A washer/dryer closet with access to utilities finishes off the living space. Outside, the generous lawn area gets plenty of sunlight. A stone patio offers a pleasant place to grill and gather around the bonfire. The two car garage offers plenty of storage, and would also make a lovely studio or game room if you prefer some space to expand. Pleasant Valley has been a steady and successful airbnb with over 100 5-star reviews. Numbers available upon request. The home is being sold fully furnished for an easy investment piece with minimal up front costs to get things rolling. Truly a turnkey experience. Pleasant Valley is less than ten minutes from Callicoon, NY, which features Sullivan County’s oldest movie theater, a fantastic, year-round farmers market, and delightful watering hole Callicoon Wine Merchant, among a wealth of dining and shopping options. The North Branch Inn & Restaurant is just a four minute drive away, making for a very attractive, convenient local haunt.

    Zillow last checked: 8 hours ago

    Listing updated: December 19, 2025 at 10:27am

    Listed by:

    Jared Gluckstern 917-716-4424,

    Country House Realty Inc 845-397-2590

    Bought with:

    Non Member-MLS

    Buyer Representation Office

    Source: OneKey® MLS,MLS#: 905784MLS Logo

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 2
    • Bathrooms: 2
    • Full bathrooms: 2
    Heating
    • Heat Pump
    Cooling
    • Ductless
    Appliances
    • Included: Convection Oven, Dryer, Electric Oven, Electric Range, Refrigerator, Washer
    Features
    • First Floor Bedroom, Eat-in Kitchen, Entrance Foyer, Open Floorplan, Primary Bathroom, Master Downstairs, Soaking Tub
    • Attic: Scuttle
    • Number of fireplaces: 1
    Interior area
    • Total structure area: 1,010
    • Total interior livable area: 1,010 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Garage
    • Garage spaces: 2
    Features
    • Has view: Yes
    • View description: Trees/Woods
    Lot
    • Size: 3 Acres
    • Features: Front Yard, Private, Secluded, Wooded
    • Residential vegetation: Partially Wooded
    Details
    • Additional structures: Garage(s)
    • Parcel number: 228902500001063001
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Bungalow,Cottage
    • Property subtype: Single Family Residence, Residential
    Condition
    • Year built: 1960

    Utilities & green energy

    • Sewer: Septic Tank
    • Utilities for property: Electricity Connected

    Community & neighborhood

    Location
    • Region: Callicoon

    Other

    Other facts
    • Listing agreement: Exclusive Right To Sell

    Price history

    DateEventPrice
    12/18/2025Sold$385,000-2.5%$381/sqft
    Source: OneKey® MLS #905784 Report a problem
    10/29/2025Pending sale$395,000$391/sqft
    Source: OneKey® MLS #905784 Report a problem
    9/3/2025Listed for sale$395,000+23.4%$391/sqft
    Source: OneKey® MLS #905784 Report a problem
    2/1/2022Sold$320,000+285.5%$317/sqft
    Source: OneKey® MLS #H6139042 Report a problem
    5/21/2018Sold$83,000-6.7%$82/sqft
    Source: OneKey® MLS #H4219138 Report a problem

    Public tax history

    Tax history is unavailable.

    Neighborhood: 12723

    Nearby schools

    GreatSchools rating
    Schools provided by the listing agent
    • Elementary: Sullivan West Elementary
    • Middle: SULLIVAN WEST HIGH SCHOOL AT LAKE HUNTINGTON
    • High: Sullivan West High School At Lake Huntington

    Source: OneKey® MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.