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$725,000

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.

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

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

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

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.

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

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.

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

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.

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

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.

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