Sold for $385,000 on 12/18/25
Zestimate®
$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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Owner options
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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#: 905784
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
| Date | Event | Price |
|---|---|---|
| 12/18/2025 | Sold | $385,000-2.5%$381/sqft |
Source: | ||
| 10/29/2025 | Pending sale | $395,000$391/sqft |
Source: | ||
| 9/3/2025 | Listed for sale | $395,000+23.4%$391/sqft |
Source: | ||
| 2/1/2022 | Sold | $320,000+285.5%$317/sqft |
Source: | ||
| 5/21/2018 | Sold | $83,000-6.7%$82/sqft |
Source: | ||
Public tax history
Tax history is unavailable.
Neighborhood: 12723
Nearby schools
GreatSchools rating
- 5/10Sullivan West Elementary SchoolGrades: PK-6Distance: 4.2 mi
- 5/10Sullivan West High School At Lake HuntingtonGrades: 7-12Distance: 8.4 mi
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.