N/A Homes with Monroe County High School

Welcome to Tompkinsville, Kentucky – a charming city nestled in the heart of Monroe County, where small-town charm meets modern convenience. Known for its friendly atmosphere and picturesque landscapes, Tompkinsville is the perfect place to call home.

As you explore this inviting community, you'll find a variety of homes that cater to diverse lifestyles and budgets. Whether you’re seeking a cozy starter home or a spacious family residence, Tompkinsville offers an array of options that can fulfill your needs. The homes here are often characterized by their unique architectural styles and well-maintained gardens, creating a welcoming environment for all.

One of the standout features of living in Tompkinsville is its proximity to Monroe County High School. Families with school-age children will appreciate the convenience of having quality education just moments away. The high school is known for its dedicated staff and strong community involvement, ensuring that students receive a well-rounded education in a supportive environment.

Beyond the homes and schools, Tompkinsville is rich in local culture and recreational opportunities. Residents enjoy access to beautiful parks, community events, and a vibrant downtown area filled with shops and dining options. Whether you’re taking a leisurely stroll through the neighborhood or participating in local festivities, there’s always something to do in this delightful city.

If you're ready to embark on a new chapter in Tompkinsville, you'll discover a community that truly feels like home. Come and experience the warmth and charm of Monroe County – your dream home awaits!

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.