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 living. This picturesque community is not only known for its friendly atmosphere and beautiful landscapes, but it also boasts a strong sense of pride in its educational institutions, particularly Monroe County High School.

Families seeking a welcoming neighborhood will find that Tompkinsville offers a variety of homes that cater to diverse lifestyles and budgets. Whether you’re looking for a cozy starter home, a spacious family residence, or a serene retreat, the real estate options here are sure to impress. Many properties are conveniently located within close proximity to Monroe County High School, making it an ideal choice for families with school-aged children.

In Tompkinsville, residents enjoy the perfect blend of convenience and tranquility. The city is surrounded by lush greenery and scenic views, providing ample opportunities for outdoor activities. From hiking and fishing to community events and local markets, there’s always something to do.

Additionally, the strong sense of community makes Tompkinsville a great place to call home. Neighbors become friends, and the local businesses thrive on the support of residents. With its rich history and vibrant culture, Tompkinsville is not just a place to live; it’s a place to grow, thrive, and create lasting memories.

If you’re ready to find your dream home in this delightful city, explore the available listings today and discover the warmth and charm that Tompkinsville has to offer!

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

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.