Main House den

Step Into a Historic Montgomery, Texas Landmark

Built in 1855, The Caroline House is a landmark of Southern craftsmanship and hospitality, a home that has stood through generations of change. Constructed by master builder John E. Shelton for his business partner, Thomas Wesley Smith, the house quickly became part of Montgomery’s growing community. Smith, a notable figure in Montgomery’s 19th-century trade and commerce, was instrumental in shaping the town’s economic landscape, while Shelton’s expert craftsmanship ensured the home’s enduring presence.

Main House parlor

Over the years, generations of owners have left their mark—expanding, remodeling, and preserving the home’s character. Through each chapter, The Caroline House has remained a beloved fixture of Montgomery, its history woven into the town’s legacy.

Through the Years from 1825 to Today

A look at how this 19th-century family home became a beloved inn in Montgomery, TX.


The Shelton-Smith House, now The Caroline House Bed & Breakfast, featuring a charming 1855 Craftsman-style home with a welcoming front porch

The Mexican government issued colonization contracts to Stephen F. Austin between the state of Coahuila and Texas. Under his 1825 contract, Austin was given six years to settle 500 families in the land between the West Fork of the San Jacinto River and the stream known as Lake Creek — what is today western Montgomery County.

The Republic of Texas declared its independence from Mexico.

William W. Shepperd, the town postmaster and mercantile store owner, changed the name of the Lake Creek Settlement to the town of Montgomery. That year, Rigby sold the remainder of his league of land to Mr. and Mrs. John F. McCuffin who homesteaded “Yesteryear”.

The McGuffins sold 1.3 acres of their homestead on the west side of “Yesteryear” to John E. Shelton for $400. John Shelton was a well-known, master craftsman in the town. He built the Main House that is known as The Caroline House today. The postmaster recorded the location of Shelton’s home as 811 Caroline Street in Montgomery, Texas.

John E. Shelton sold the home to his good friend and business partner, Captain Thomas Wesley “T. W.” Smith, for $425. For this reason, 811 Caroline Street is commonly known as the “Shelton Smith House”. T. W. and his wife Margaret raised their 8 children in the home.

Thomas Wesley Smith transferred the home to Wesley Joseph “W. J.” Smith for $10, citing his fatherly love and affection. The Smith Family remodeled the home in the Victorian manner in the 1890’s and converted the gas lamps to electric. W. J. and his wife Ella raised their 3 children in the home.

Westley Joseph Smith willed the home to his daughter, Stella Smith, who later married Frederick Williamstone “Bub” Peynghaus. Stella and Bub remodeled the old family home, adding two more dormer windows to the roof and converting the attic space into a 2-story home.

The Smith-Peynghaus Family sold the home to Thomas A. and Edna Blalock Gay. The Gays added indoor plumbing to the home, creating four indoor bathrooms and a kitchen with a sink. Thomas and Edna raised their only child in the home.

Upon her death, Edna Gay willed the home to her only son, Green Duke Gay II and his wife Suzie. They had the greenhouse at the back of the property built and the windows enclosed with the newly invented product – plexiglass.

Kenneth and Mary Whisenant purchased 811 Caroline Street from the heirs in possession of the Gay Family Estate. They restored the home to its original character and added the HVAC system. Mary used the greenhouse for growing a wonderful variety of orchids.

The Whisenant Family Estate sold the property to Richard Eckhart and Mary Catherine Eckhart Sims. Mary converted the old slave’s quarters into a cozy “Honeymooners Cottage” with a bathroom and bedroom. Mary also converted the old greenhouse into a “Guest House” with 3 bedrooms, 2 bathrooms and a kitchen. Mary had a vision for what the home could be if it was opened to the public. She poured her love into the Shelton Smith Home at Yesteryear and created The Caroline House Bed & Breakfast.

Mary Sims sold the property to Eric and Connie Renouard. The Renouards love the history and character that the Shelton Smith Home has to offer. In keeping with the previous owner’s vision, the home will remain open as The Caroline House Bed & Breakfast. They invite you to experience the charm that this lovely vintage home from the 1850’s has to offer.


Texas and American flags displayed on hay bales in front of a rustic barn in Montgomery, TX

Walk the Streets Where the Texas Flag Was Born

Your stay at our historic Montgomery, TX inn feels like stepping back in time, right in the heart of one of Texas’ earliest towns. Established in 1837, Montgomery was a vital trade hub and the home of Dr. Charles B. Stewart, who designed the Texas Lone Star Flag in 1839.

Stroll past original 19th-century buildings, explore museums, or take a guided tour, all while enjoying the town’s relaxed atmosphere and unique shops—perfect for those interested in Texas history and small-town charm.