Good Hill Real Estate

Welcome to Good Hill, an enchanting neighborhood nestled in the heart of Litchfield County, Connecticut. Known for its picturesque landscapes and close-knit community, Good Hill offers a serene escape from the hustle and bustle of city life while still providing convenient access to modern amenities.

As you wander through the tree-lined streets of Good Hill, you’ll be captivated by the charming mix of historic homes and contemporary residences, each exuding unique character and warmth. The neighborhood is characterized by its lush greenery, rolling hills, and scenic views that change beautifully with the seasons. Whether you’re enjoying a leisurely stroll, biking along the winding roads, or simply soaking in the tranquility of nature, Good Hill invites you to embrace a lifestyle of peace and relaxation.

Families will appreciate the top-notch schools in the area, which are known for their commitment to academic excellence and community involvement. Parks and recreational facilities abound, offering residents ample opportunities for outdoor activities, from hiking and biking to picnicking and community events.

Good Hill is also conveniently located near charming local shops, delicious eateries, and cultural attractions that showcase the rich heritage of Litchfield County. With easy access to major highways, residents can enjoy the best of both worlds— the quiet charm of suburban living and the vibrant energy of nearby towns.

Discover the magic of Good Hill, where community spirit thrives, nature flourishes, and every day feels like a breath of fresh air. Your dream home awaits in this idyllic neighborhood!

Newest Listings in Good Hill

$485,000

24205122 MLS

Welcome to Lot 8 Willow Brook Drive! If your dream has been to build your custom home on a picturesque canvas of classic New England countryside, this property is ready to bring your vision to life. Offering 10 sprawling acres of peaceful, former cattle pasture, Lot 8 provides a gentle, easy-to-build landscape framed by open meadows and surrounding natural woodland. The lot benefits from lovely western exposure, capturing warm afternoon light and golden evening sunsets across the fields. Tucked on the land is the existing foundation of an old barn, offering a solid base with potential to be reutilized in your future building plans. This approved building lot is ready to develop with easy, clear meadows for your architectural vision. Underground power and utilities run right along Willow Brook Drive, and a survey/feasibility map with original percolation and soil data is available upon request. Bring your builder and let your imagination run wild on this magical Roxbury acreage!

Lot 8 Willow Brook, Roxbury

$699,900

3 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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 ⋅ 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

$135,000

24199941 MLS

Here's your opportunity to turn a blank canvas into the home you've always envisioned. This vacant lot offers buyers the flexibility to design and build a home that fits their lifestyle, preferences, and future goals. Imagine choosing your own floor plan, finishes, kitchen, bedrooms, outdoor living spaces, and modern features-all while creating a home from the ground up. Whether you're a first-time buyer looking to build something of your own, a growing family searching for the perfect place to settle down, or an investor looking for a development opportunity, this property offers exciting possibilities. With the limited amount of vacant land for sale in the town of Oxford, this opportunity won't wait forever. The land is here- the next chapter is yours to build. Buyer to perform their own due diligence. Seller has not perform any surveys, perc test, etc.

70 Old Good Hill Rd Rd, Oxford

$250,000

24192651 MLS

An exceptional opportunity to own 76.9 +/- acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of this 14.9-acre parcel and the adjoining 62-acre parcel (MLS #24192209). Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, mountain laurel, stone walls, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

Hoop Pole Hill, Woodbury

$1,000,000

24192209 MLS

An exceptional opportunity to own 76.9 acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of 14.9-acre parcel (MLS# 24192651) and this adjoining 62-acre parcel Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

245 Hoop Pole 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

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