Orchard cottage, the oldest house in Cragsmoor circa 1824, is a stately anchor of the lovely hamlet of Cragsmoor. Once inside the vibe is comfortable, inviting and so very interesting with its rich patina woodworking, charming built-in features, sprawling rooms with architectural angles and surprises, many windows and doors that call the outdoors inside and allow easy access to the East and West covered porches perfect for entertaining and relaxation. The history of Orchard Cottage is as interesting as its interior. It was once a tavern, an inn and for many years the local post office. When it was purchased in 1902 by Fredrick Dellenbaugh (20th century explorer, artist and author) the house was named Orchard Cottage by Dellenbaugh's sister, Belle and became a place of gathering and community. With over four decades of stewardship, the current owners are ready to offer this unique property for sale. There is almost 3000 square feet of living area, 6 bedrooms, 3.5 baths, 4 fireplaces, a Franklin Stove and a fireplace with a beehive oven in the basement. The first floor offers an eat-in kitchen with bathroom and laundry area, a sunroom, a combination living-dining room with fireplace, another family-living room with a fireplace, an ensuite that has a bedroom with a Franklin Stove, sitting room and bathroom. Every room on the first floor has a door to access the 3 sided porch. The second floor has a primary bedroom with fireplace and bathroom, a third bedroom with a fireplace, a sweet fourth bedroom overlooking the private backyard, and another ensuite area with 2 bedrooms, a bathroom and a sitting area. There are two staircases to access the second floor. A small walkout basement offers storage. A one car garage that historically offered a second-floor apartment is ideal for a studio or makeover. The property is 4 acres with open lawn and woods and a small stream. A generator that provides peace of mind in all weather conditions. With 5000-acre Sams Point nearby and Bear Hill Preserve 3/10 a mile away there is endless hiking opportunity. Under 2 hours to the GW bridge for a great weekend escape or enjoy as a full-time home.

Property Details of 5 Dellenbaugh Road

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of November 10, 2026 12:06 PM EST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. IDX information is provided exclusively for consumers’ personal noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. The use of the MLS GRID Data may be subject to an end user license agreement.

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