In the heart of Hambletonian country, Chester, NY is "Brook Manor" the former horse training estate of financier and Tuxedo Park resident, Richard Delafield. The estate, now an assemblage of 3 parcels of just under 10 acres, has a rich history and was home to Delafield's farm Superintendent. Perched on a sweeping lawn above Main Street, this stately brick, slate, and carpenter's lace adorned manor offers compound-level privacy and amenities - including a separate cottage - yet is accessible to the village. Circa 1851, the approx. 4,000 sq. ft. manor home was originally part of the 128-acre "Brook Farm", named after Delafield's Tuxedo Park property. It was designed by owners prior to Delafield for grand entertaining. Out front, a covered porch greets you with views over Chester Village. Inside are the formal center hall, parlor, dining and drawing room w/ fireplaces, some areas here boasting 10' ceiling heights and gorgeous hardwood floors. A working-kitchen with dinette, butler's pantry and powder room round out the main level's openness and flow. Upstairs, by both front and rear staircases, the 4 bedrooms have character and period architectural details and are served by 2 full bathrooms. The 3rd floor walk-up offers 2 finished bonus rooms. A walk-out basement is reminiscent of a colonial tavern with its rustic bar, fireplace and an exterior door that leads to a pebbled courtyard. The home's distinct warmth and flow are perfect for both entertaining and daily living. The expansive land is well-suited for recreation, gardening, and outdoor entertaining. The original 128-acre property was once replete with a state-of-the-art horse training track, stables, barns, tenant houses, an icehouse, chicken coops and more. Currently the property is just under 10 acres combined; the modest accessory cottage, tennis court and barn remain, some needing work. Included in the sale is the 4-bedroom main home and the 2-bedroom cottage on a 6.8-acre parcel, and two additional adjoining land parcels which are separate tax lots of 2.1-acres, and .78-acre. With hundreds of feet of road frontage on the front parcel, there may be the possibility of future subdivision. Conveniently located in the heart of Orange County, this unique property bundle is near major highways and area attractions including Orange County's "Rail Trail", Goshen Historic Track, Legoland NY, black-dirt farm-to-table restaurants/breweries/distilleries, Shawangunk wine trail and more. It's just ~75 minutes from NYC. A one-of-a-kind lower Hudson Valley village estate, not to be missed.