Good Hill Homes with Colonial Style

Welcome to Good Hill, a picturesque neighborhood nestled in the heart of Woodbury, Connecticut, within the charming Litchfield County. Known for its serene landscapes and rich history, Good Hill offers a delightful blend of rural charm and modern conveniences, making it an ideal place for families, retirees, and anyone looking to embrace a tranquil lifestyle.

As you stroll through the tree-lined streets of Good Hill, you’ll be captivated by the stunning Colonial-style homes that define the area. These timeless residences, often adorned with classic white clapboard siding and stately brick facades, exude elegance and warmth. With their spacious layouts, high ceilings, and intricate moldings, Colonial homes offer both comfort and sophistication, making them perfect for entertaining guests or enjoying quiet family evenings. Many of these homes are set on generous lots, providing ample outdoor space for gardens, play areas, or simply enjoying the beauty of nature.

The neighborhood is not only a feast for the eyes but also a community where neighbors become friends. With local parks, walking trails, and a vibrant town center just a short drive away, residents of Good Hill enjoy a variety of activities, from farmers' markets to art fairs. The excellent schools and a strong sense of community make it a sought-after location for families looking to settle down.

In Good Hill, you’ll find more than just a home; you’ll discover a lifestyle rich in history, community spirit, and the beauty of Connecticut living. Come and experience the charm of Good Hill for yourself!

Newest Good Hill Homes with Colonial Style

$699,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24204212 MLS

Imagine starting your morning with a cup of coffee on the gorgeous wraparound front porch as you take in the view of Radey Pond or spending warm summer evenings entertaining family and friends in this beautiful and private setting.Situated on 2.31 acres, this charming 3/4-bedroom, 2.5-bath Cape/Colonial offers the perfect combination of classic New England character, comfortable living space, and a flexible floor plan. At the heart of the home is the spacious eat-in kitchen, offering plenty of counter and cabinet space and flowing naturally into the inviting family room with a cozy fireplace. Whether you're entertaining a crowd or enjoying a quiet evening at home, this warm and welcoming space is made for gathering.A separate living room and office/den provide additional options for relaxing, working from home, or creating a space that fits your lifestyle.Upstairs, the spacious primary suite is a true retreat with a large closet and private full bath featuring a spa tub and separate shower. Two additional generously sized bedrooms share another well-appointed full bathroom.Need even more room? The finished third floor offers wonderful flexibility and can easily become a fourth bedroom, private home office. Hardwood floors throughout add timeless appeal, while a new roof offers peace of mind.Outside, the 2.31-acre private lot and beautiful pond views create a setting that feels removed from it all, while still being conveniently located near amenities, and major highways

201 Transylvania Rd, Woodbury

$699,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$875,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24200842 MLS

Original owner, large Colonial Home with 4 room, private entry inlaw suite on the main level. Close to town center and schools. 4180 s/f plus the 750 s/f inlaw! Bring on the big multi-generational family! Natural sun filtered house has front and back staircases, large rooms, 9'ceilings, and mostly hardwood. Granite kitchen/ great room open to breakfast nook, family room w fireplace and french doors to rear decking. Formal dining room and living room are a must in this classic style. The entertaining space is oversized so host all the holiday gatherings with ease. Primary suite is HUGE, walk in plus another closet and luxury bath. 3 additional bedrooms and an office. A separate 2nd floor laundry room, also very generous in size. Very level usable yard with a large area off the back deck fenced for dogs. (used to have a pool). Brand new central AC unit, refinished hardwood and fresh paint on the main level. In-law apartment is propane heat/ac

132 Good Hill Rd, Woodbury

$1,790,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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

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