Built in 1870 and listed at $849,000, this remarkable 5,000-square-foot stone home in Woodbury offers a rare blend of history, craftsmanship, and modern comfort. Fondly known as “The Castle” by locals, the property began as a stagecoach stop and sits beside a brook once frequented by the famed wanderer known as the Leatherman. In the 1970s, a man nicknamed “Cadillac Joe” took on the ambitious project of transforming the home into a grand stone castle. Every stone was hand-placed with care and intention, though age left his dream unfinished. Today, that vision has been beautifully realized, with extensive updates such as new mechanical, plumbing, and electrical systems, septic and well, flooring, and a new roof.

Stone Home Exterior

A spacious, multi-level home with a predominantly stone exterior is displayed. The facade features arched doorways and windows on the lower level, transitioning to balconies with wrought-iron railings on the upper floors. A dark grey roof covers the structure. A wide, paved driveway, scattered with fallen autumn leaves, leads up to the house.

Where is Woodbury?

Woodbury is a town in Litchfield County, Connecticut, known for its historic charm, antique shops, and scenic rural setting. Located in western Connecticut, it’s about a 90-minute drive from New York City, making it a quiet but accessible retreat. The area features classic New England architecture, rolling landscapes, and a strong sense of community rooted in its long history.

Stone Pathway

A rugged stone pathway leads upwards, flanked by rough-hewn stone walls. The path appears to be made of irregularly shaped stones, giving it a natural, weathered appearance. To the right, a balcony with white railings and wooden supports juts out, offering a view of the surrounding landscape.

Balcony

A long stone balcony with white and black railings extends along the side of a stone building. The balcony offers an expansive view of a wooded landscape, where many trees are bare, while others display vibrant autumn foliage in shades of orange and brown. The balcony itself has a concrete floor and a stone wall forming the building’s exterior.

Exterior with Arched Window

A close-up view reveals a home’s textured facade and architectural details. A prominent arched window with multiple panes is set into the wall, emitting a warm interior light. A balcony with white railings and black vertical bars runs along the side of the dwelling. The building material varies in size and color, creating a rustic and natural appearance.

Rear Exterior

The rear view of a multi-level home reveals a combination of materials, including light-colored siding and a substantial foundation built with rugged rocks. Multiple balconies with white railings offer outdoor living spaces on different levels. Large windows provide views into the interior. A prominent stone chimney rises along one side of the house.

Backyard

This spacious backyard of a stone residence blends seamlessly with its natural surroundings. Mature, bare trees frame the property, while a stone retaining wall defines the yard. The home’s rear features varied windows and a multi-level design, with a stone pillar supporting a balcony. A paved area extends from the house into the yard, which is covered in sparse grass and fallen leaves.

Aerial View

This aerial shot showcases the layout of a large stone house, featuring its dark grey roof, numerous windows, and multiple balconies with white railings. A paved or stone patio area surrounds the house, and a winding stone pathway leads down the hillside. The property is nestled among mature trees, some retaining their fall foliage.

Open Space with Dining

A spacious open area features light-colored hardwood flooring and a prominent accent wall of exposed, rugged stonework. A dark, round dining table with two black chairs sits near the stone wall. Adjacent to this area is a kitchen island with a light countertop and five tall stools upholstered in purple. The overall space feels large and airy, with recessed lighting illuminating the different zones.

Expansive Kitchen

This expansive kitchen features rich, warm-toned wooden cabinetry extending along one wall and forming a large central island with a light countertop and seating for six on dark upholstered stools. Stainless steel appliances, including a built-in microwave and a large range, are prominent. Light-colored granite countertops run along the perimeter cabinets. The flooring is light-colored hardwood, extending throughout the spacious area.

Entryway

A spacious entryway features light-colored hardwood flooring and a striking accent wall of exposed, rugged stonework. A dark, round table with two black, upholstered chairs is positioned against the stone wall, creating a small dining or seating nook. To the left, a set of ornate wooden double doors with patterned glass panels serves as the main entrance.

Grand Room

This grand room boasts a dramatic combination of natural materials and architectural features. A high ceiling with exposed wooden beams and planks creates a rustic yet spacious feel. One wall is entirely clad in irregular, light-colored stonework, adding texture and visual interest. Light-colored hardwood flooring extends throughout the expansive space. Two elegant chandeliers with multiple lights hang from the ceiling, providing illumination.

Expansive Room

This expansive room features warm-toned hardwood flooring and white walls, creating a bright and airy atmosphere. One section of the wall is accented with rugged stonework, incorporating arched niches and a raised platform. Large windows with multiple panes offer views of the outdoors, bringing in natural light.

Modern Bathroom

This modern bathroom features a curved glass shower enclosure with a white base and silver fixtures. A white vanity with a light-colored countertop and a chrome faucet is situated next to the shower. The flooring is dark wood-look laminate. A window with white blinds allows natural light into the space. A white toilet is visible in the bottom left corner.

Bright Room

This bright and spacious room features light-colored hardwood flooring and white walls, creating an airy feel. Natural light floods the space through multiple windows, including a large arched window and sliding glass doors that lead to a balcony with white railings. A ceiling fan with light fixture is mounted in the center of the ceiling.

Room with Vaulted Ceiling

The architectural details of this spacious room include a striking arched window, a high vaulted ceiling, and light-colored hardwood flooring. White walls provide a neutral canvas. A ceiling fan with a light fixture adds a functional element. A dark-framed door and white double-closet doors are present, and a view into an adjacent stone-accented area with stairs hints at the home’s design.

Bathroom with Double Vanity

This bright bathroom features a double vanity with white cabinets, light countertops, and chrome faucets. Two rectangular mirrors are mounted on the white wall above the vanity, illuminated by modern lighting fixtures. To the left, a white toilet sits on the dark wood-look flooring. A section of the wall behind one of the mirrors reveals exposed, rugged stonework with an arched opening.

Stone Wall Room

A striking wall of rugged, light-colored stonework dominates this spacious room, providing a strong textural element. Two arched windows, fitted with multiple panes, are integrated into the stone, drawing in natural light. The remaining walls are painted white, offering a clean contrast to the rustic stone. Light-colored hardwood flooring spans the room, and simple ceiling lighting is present.

Stone Window Alcoves

The defining feature of this bright room is the presence of two distinct window alcoves, each uniquely framed by rugged, light-colored stonework. These textured alcoves add significant architectural interest and a touch of natural rusticity to the otherwise smooth white walls. Light-colored hardwood flooring spans the room, reflecting the natural light that streams in through the multi-paned windows with white frames.

Bathroom with Clawfoot Tub

This bright bathroom features a classic white clawfoot bathtub positioned against a wall with exposed, rugged stonework surrounding a large window. The window offers a view of the outdoors. A white double vanity with light countertops and oval mirrors is located on the opposite wall, illuminated by modern vanity lights. A white toilet sits between the tub and the vanity.

Listing Agent: William Raveis Real Estate via compass