Tompkinsville Real Estate

Welcome to Tompkinsville, Kentucky – a charming gem nestled in the heart of Monroe County. This quaint city, with its rich history and warm community spirit, offers a unique blend of small-town charm and modern conveniences. With a population of just over 2,500 residents, Tompkinsville is the perfect place for those seeking a close-knit community where everyone knows their neighbor.

The city is steeped in history, with roots that trace back to the early 1800s. Stroll through the picturesque streets and you’ll find beautifully preserved buildings that tell the story of a bygone era. The local culture is vibrant, with annual events that celebrate the community’s heritage, including the popular Tompkinsville Tomato Festival, which draws visitors from near and far.

Nature lovers will appreciate the stunning landscapes that surround Tompkinsville. With rolling hills, lush farmland, and serene lakes, outdoor enthusiasts can indulge in a variety of activities such as hiking, fishing, and boating. Nearby Barren River Lake State Resort Park offers a perfect getaway for families and adventurers alike, boasting scenic views and recreational opportunities.

Tompkinsville is also home to a thriving local economy, with a mix of small businesses and larger employers, ensuring that residents have access to a range of services and job opportunities. The local schools are known for their commitment to excellence, making it an ideal place for families looking to settle down.

Whether you’re searching for a cozy home, a friendly community, or a place to create lasting memories, Tompkinsville, KY, is ready to welcome you with open arms. Discover the charm and warmth of this delightful city today!

Newest Listings in Tompkinsville

$246,500

2995396 MLS

Seventeen acres of Kentucky countryside, wide and open, with a mix of level pasture and gentle rolling hills that make it feel like something straight out of a country song. Zoned agricultural, this land is a clean slate—perfect for a dream home, mini-farm, or a quiet hideaway where you can hear your thoughts and watch the stars actually sparkle. Tompkinsville sits at the heart of Monroe County, where folks still wave when they pass you on the road and the barbecue has a kick you won’t forget. Spend your weekends fishing or kayaking at Dale Hollow Lake, just a short drive away, or exploring the Old Mulkey Meetinghouse State Historic Site—a time capsule of Kentucky’s pioneer roots. When you’re ready for a little more buzz, head to nearby Glasgow or Burkesville for local festivals, antique shopping, and small-town diners that serve up the kind of pie that ruins all others for you. Life here moves at the right pace: steady, neighborly, and peaceful. Whether you’re building a homestead, expanding your agricultural operation, or simply staking your claim on a piece of God’s country, this land gives you the space—and the freedom—to do it.

1 County House Rd, Tompkinsville

$100,000

2995298 MLS

Step back in time with this beautifully preserved home from the 1800s, nestled on one acre in scenic Monroe County. This piece of Kentucky history stands proud on County House Road, offering the charm and craftsmanship of the past with the peace and quiet of rural living. From its solid bones and timeless architecture to its wraparound sense of calm, this home radiates warmth and authenticity—truly a rare find in such great condition. Surrounded by open countryside, you’ll find yourself just minutes from Tompkinsville, a small town with a big heart. Explore the historic Old Mulkey Meetinghouse, enjoy local barbecue that’s been perfected over generations, or take a drive to Dale Hollow Lake for boating, fishing, and those postcard-worthy Kentucky sunsets. The area is rich with hiking trails, farmers’ markets, antique shops, and family-owned eateries that make every outing feel like an escape into simpler times. For a bit more activity, Glasgow and Burkesville are both a short drive away, offering small-town festivals, shopping, and that unmistakable Southern hospitality. Whether you’re looking for a home with history, a peaceful weekend retreat, or a project that deserves your care, this property offers endless potential and a story worth continuing. It’s more than a house—it’s a piece of Kentucky’s past waiting to welcome your future.

County House Rd, Tompkinsville

Start Your Search

Information Is Believed To Be Accurate But Not Guaranteed. Some or all listings may or may not be listed by the office/agent presenting these featured properties. Copyright 2026 MTRMLS, Inc. RealTracs Solutions.