N/A Homes with Monroe County High School

Welcome to Tompkinsville, Kentucky, a charming city nestled in the heart of Monroe County. Known for its warm community spirit and picturesque landscapes, Tompkinsville is an ideal place for families, retirees, and anyone seeking a peaceful lifestyle. The area boasts a rich history, vibrant local culture, and an abundance of outdoor activities, making it a perfect location to call home.

One of the standout features of Tompkinsville is its proximity to Monroe County High School, a well-regarded institution that serves the community's educational needs. Families with school-aged children will appreciate the strong emphasis on academic excellence and extracurricular opportunities that the high school offers. Living close to the school not only fosters a sense of community but also provides convenience for parents and students alike.

The homes in this area reflect a variety of architectural styles and sizes, catering to diverse preferences and budgets. Whether you’re searching for a cozy cottage or a spacious family home, Tompkinsville has something for everyone. Many properties are set against the backdrop of lush greenery, offering residents a serene environment to unwind and enjoy nature.

In addition to the appealing homes, Tompkinsville is rich in local amenities, including parks, shops, and dining options that create a welcoming atmosphere. The friendly neighbors and strong community ties make it a place where you can truly feel at home.

If you're looking for a charming place to settle down, consider Tompkinsville, where quality living meets a strong sense of community. Come explore the possibilities today!

Newest N/A Homes with Monroe County High School

$246,500

2995396 MLS ⋅ ACTIVE Status ⋅ 17 Acres ⋅ 42167 Zip Code

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 ⋅ ACTIVE Status ⋅ 1 Acres ⋅ 42167 Zip Code

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

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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.