Discover the Timeless Virginia Highland House: Architecture, History, and Charm

Nestled among the rolling peaks of Virginia’s highlands, the Virginia Highland House stands as a testament to timeless design and historical significance, offering a rare blend of charm, craftsmanship, and natural beauty that captivates visitors and homeowners alike.

Built in the early 20th century, the Virginia Highland House exemplifies classic mountain architecture with its hand-hewn timber framing, steeply pitched roofs, and expansive wraparound porches. Originally a private estate, it reflects the lifestyle and artistry of early Appalachian settlers, preserving a tangible link to regional heritage through meticulous restoration and enduring design.

Beyond its architectural beauty, this historic home offers a unique lifestyle defined by seclusion, natural splendor, and cultural depth. With sweeping views of the highlands, original fireplaces, and period details, it appeals to those seeking authenticity and connection to place—making it a prized asset in Virginia’s premium mountain real estate market.

Today, the Virginia Highland House balances historical integrity with modern comforts, featuring updated HVAC, energy-efficient systems, and thoughtful renovations that honor its legacy. Its prime location near recreational trails and scenic vistas enhances its appeal, positioning it as a rare opportunity for discerning buyers who value both preservation and contemporary living.

The Virginia Highland House is more than a home—it’s a living piece of history, steeped in mountain charm and architectural excellence. Whether as a dream residence or a meaningful investment, it invites you to step into a world where past and present beautifully converge.

Highland is a historic house museum at the home of James Monroe, fifth president of the United States of America. Part of Monroe's alma mater, William & Mary, Highland offers guided tours daily and hosts community and private events throughout the year. Highland, formerly Ash Lawn-Highland, located near Charlottesville, Virginia, United States, and adjacent to Thomas Jefferson 's Monticello, was the estate of James Monroe, a Founding Father and fifth president of the United States.

Plan your visit to James Monroe's Highland! Highland offers guided tours daily and hosts community and private events throughout the year. The Monroe guesthouse showcases a rich collection of objects original to James and Elizabeth Monroe, as well as period pieces similar to those owned by the Monroes, and some modern reproductions. 1818 Guesthouse Highland's new interior exhibits are designed as a self-paced experience that weaves the story of Highland's free and enslaved residents into the same narratives.

Focusing on Monroe's presidential years, the exhibits show how Highland is a lens for understanding early American history and its present. The Virginia-Highland Tour of Homes showcases the neighborhood's most charming residences, each adorned in festive holiday décor. From historic bungalows to elegant revival styles, the tour offers a rare peek inside these architectural treasures while supporting the Virginia.

The main home at Highland is the Massey house from 1870. The original Monroe home's foundation is undergoing archaeological investigation, and we will hopefully soon about the structure. However the guest home behind the Massey house does date to Monroe's time (see drawing below).

What is Highland? William & Mary's Highland is a historic site located outside of Charlottesville, Virginia. It is notable as the home of W&M alumnus and 5th U.S. President (1817-1825) James Monroe, and the site tells the stories of people and events reflecting significant years in the development of the United States.

Highland - along with the Omohundro Institute, the Muscarelle Museum of. James Monroe's Highland is the home of the fifth U.S. President, and a historic site encompassing 535 acres in Central Virginia.

Open year-round, Highland offers guided tours, packages for tour groups and school visits, and augmented reality experiences of the landscape. Highland initiated archaeological and architectural research in 2014 that discovered the buried remains of Monroe's main house and correctly identified the standing house as an evolved structure built from an 1818 presidential guesthouse.