16 Jonathan Drive

Roxbury, CT 06783

Tucked away on a highly sought-after country road, this charming Colonial has been lovingly maintained by its original owners and offers privacy, lovely grounds, and exceptionally low taxes. Distinctive character begins with its graceful rounded-front porch and continues throughout this exceptionally well-built home, where timeless craftsmanship meets enduring charm. A welcoming foyer features a distinctive staircase to the upper level and opens to the living and dining rooms on the left, while a cozy den flows into the bright eat-in kitchen on the right. The laundry and half bath are conveniently located just off the kitchen. Beautiful hardwood floors, two fireplaces, and French doors leading to private patios create inviting spaces for everyday living and entertaining. Upstairs, the spacious primary suite offers walk-in closets and a well-appointed bath with Jacuzzi and large separate shower. Two additional bedrooms feature generous closets, complemented by a large linen closet. This well loved home is on a beautiful lot, at an approx. 1000 ft elevation, has mature landscaped grounds, private patios and a cute garden shed creating a peaceful country retreat. There is an approx 1,100 sq ft basement with tall ceilings offering a great expansion opportunity, or excellent for storage. Roxbury is a quintessential New England community with very low taxes and home to well-regarded schools. It is also known for its natural beauty, historic character, and strong sense of community. Conveniently located near Southbury, Bridgewater, Washington, and Woodbury, Roxbury is a small, close-knit community of approximately 2,260 residents where privacy, natural beauty, and a strong sense of place define the lifestyle. Part of Regional School District 12, Roxbury is home to the highly regarded Booth Free School and offers access to Shepaug Valley School, including the Shepaug Agriscience STEM Academy, providing distinctive educational opportunities from middle school through high school. Roxbury captures the timeless elegance of New England country living, where rolling hills, stone walls, historic architecture, open fields, and wooded landscapes create a setting of exceptional natural beauty. Peaceful and private yet conveniently connected, the town offers an easy balance of rural tranquility and accessibility, with Brewster and Southeast Metro-North stations approximately 30 minutes away for convenient rail access to New York City. Outdoor recreation, hiking, parks, dining, boutique shopping, and cultural destinations are all close at hand. From quiet mornings surrounded by nature to afternoons exploring nearby trails and charming villages, Roxbury offers an understated, sophisticated lifestyle-one that feels wonderfully removed from the pace of the city while remaining approximately 90 minutes from New York City.

Listing courtesy of Ginny Gordon-O’Neill of William Raveis Real Estate Office Phone: (203) 794-9494 Broker Contact: (774) 222-5590



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Last checked: 2026-09-11 05:35 PM UTC.