239 Painter Hill Rd Roxbury CT

Originally homesteaded in the c.1860’s by the O’Brien Family, the current 12-acre estate was once part of a 222-acre farmstead and is historically significant as one of few Roxbury properties that remained in the family of the original owners for over 150 years. The original English bank barn with its post-and-beam frame has been well maintained and is featured in the Roxbury barn books as a fine example of distinctive building. It stands on the south side of the estate, bordered by stone walls and comprised of a c.1872 main residence, guest house, gunite pool, a screened pool folly, two orchards, and a brick dining patio.

Fully renovated in 2015, character, charm, and romance continue to define this stunning property, located in a whisper-quiet setting with western exposure at the top of Painter Hill. The white clapboard farmhouse is beautifully sited on 12± acres of level lawn accented with lush, canopied trees, flowering perennials, stone walls, and abundant birdsong… the picture-perfect essence of New England just 90 minutes from NYC.

The 5-bedroom/3.1-bath main residence encompasses 3,000+/- square feet (excluding finished lower level), with seven rooms on the main floor and six above. The interior exudes character with old-world oak flooring, solid core doors, Baldwin Black Brass hardware, and period details including exposed hand-hewn ceiling beams. The country kitchen with glass-faced cabinetry and soapstone counters is fitted with all designer appliances including full-sized Subzero refrigerator and freezer, Wolf gas stove with sapphire blue enameled interior, and boasts a walk-in pantry, and butler closet with additional storage. A formal dining room is wrapped in 8-over-8 windows offering sunset views and direct access to outdoor dining patio. Adjacent is a formal living room with views of the grounds and wood-burning fireplace as its focal point. Opposite is a cozy front family room for reading or relaxing. Quietly set apart from the main living space is a first floor Master Suite with private screened sitting porch, walk-in closet/dressing room, and a 5-piece marble bath with dual sinks, free-standing soaking tub and separate shower. Completing the main floor is an office, and a laundry room with double set of Meile washer/dryer, sink, ample storage cabinets, and garden access.

The second floor comprises four guest bedrooms — two with sleeping coves and built-in storage. The guest rooms are paired on opposite sides of the house and serviced by two full baths — each with a double marble sink. The lower level is partially finished and features a temperature-controlled wine cellar and additional pantry.

The 1-bedroom guesthouse is ideally suited for guests’ extended stays, a caretaker’s house or as an onsite rental income opportunity. It offers a full eat-in kitchen with double SubZero and appliances/finishes keeping with the quality of the main house. There’s a half bath and an ensuite bedroom on the main level, while the upper level comprises a media room with two sleeping coves.

Both the main house and guest house have cedar shake roofing with copper seams and gutters. There’s also a full house generator, a 900-gallon backup water tank, and an irrigation system that waters the orchards, lilacs, flower and herb gardens and the lawn around the house. 

There are two garages in the barn. Current owners have plans available that envisions combining the two barns into a residence with one very large open top floor with spectacular Western views.  

Further History

Information from a survey of Roxbury by Rachel Carley. This 19th-century farmstead is significant as one of few Roxbury properties remaining in the family of the original owners. An Irish immigrant, Thomas O’Brien (b. 1845) came to America in 1848 as a child and became a citizen in 1872. In 1924 he deeded his home lot to his son Edward J. O’Brien, who then owned the property at 277 Painter Hill. In 1970, this property at 238 Painter Hill Road was distributed from Edward’s estate to his son Joseph O’Brien, who grew up on his father’s farm at 277 Painter Hill Road. Here at 238 Painter Hill Road, Joe O’Brien maintained a herd of about 85 head of cattle and also raised pigs and poultry. The family owned 222 acres on Painter Hill and Painter Ridge Roads and another 20 acres on Booth Road. Crops included tobacco, hay and corn to provide silage for the dairy herd and timothy for the workhorses. There was also an apple orchard.

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