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55 Good Hill Rd, Woodbury
$1,790,000
4 Beds ⋅ 5 Baths ⋅ 24136657 MLS
Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury
15 Saxony Ln, Woodbury
$699,900
4 Beds ⋅ 3 Baths ⋅ 24206989 MLS
Welcome home to this beautifully maintained 4-bedroom, 2.5-bath center hall colonial, ideally situated on a desirable cul-de-sac just minutes from the charming town centers of Woodbury and Roxbury. With its quintessential wrap-around front porch and classic New England character, this home offers timeless appeal in a wonderful setting. A gracious foyer welcomes you with a formal dining room and versatile living room/den, perfect for a home office, library, or sitting room. The remodeled kitchen features granite countertops, stainless steel appliances, gas range, and large center island flowing seamlessly into the eat-in dining area. The spacious family room with cozy wood-burning fireplace. Upstairs, the private primary suite features a walk-in closet, fireplace, and en-suite bath with soaking tub and separate shower. Three additional bedrooms offer comfortable space and abundant natural light. The finished lower level provides flexible space for work, play, fitness, media, or recreation. A convenient mudroom/laundry room off the attached two-car garage includes a private half bath and granite counter, while a generator hook-up and new well pump provide added peace of mind. Outside, an oversized shed with loft storage offers plenty of room for tools and seasonal items. Enjoy the beauty of fall in Woodbury, from the inviting front porch to the nearby town centers, this home captures the warmth and charm of Litchfield county living.

15 Saxony Ln, Woodbury
24 Old Good Hill Rd, Oxford
$699,000
4 Beds ⋅ 2 Baths ⋅ 24198970 MLS
A rare blend of historic New England character, sophisticated style and exceptional outdoor living, 24 Old Good Hill Road is anything but ordinary. Dating to 1829 and set on approximately 2.55 beautifully landscaped acres, this distinctive home has been thoughtfully updated while preserving the warmth and architectural details that give it its soul. Inside, the feeling is timeless and collected-reminiscent of a Ralph Lauren country house-with rich character, built-in bookcases, two impressive stone fireplaces, including one with a built-in wood stove, and inviting spaces designed to be lived in and enjoyed. Outside, decades of established landscaping create a private retreat of mature trees, perennial gardens and multiple patios for dining, entertaining and relaxing. A built-in swimming pool becomes the centerpiece of summer living, surrounded by the privacy and beauty of the grounds. A former barn site also presents an intriguing opportunity for a future garage or accessory structure, subject to municipal approvals. This is the real thing-not a reproduction, but an authentic Connecticut home that has evolved beautifully for nearly two centuries. Historic without feeling like a museum, updated without losing its soul. From quiet mornings among the gardens to summer afternoons by the pool and evenings gathered around the fire, this is a home with a remarkable sense of place-private, welcoming and designed to be enjoyed in every season.

24 Old Good Hill Rd, Oxford

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