Chester County Real Estate

Welcome to Chester County, Tennessee, a hidden gem in the heart of the Volunteer State! Known for its rich history, picturesque landscapes, and warm community spirit, Chester County offers a unique blend of rural charm and modern convenience that makes it an ideal place to call home.

Nestled between the scenic Tennessee River and the stunning hills of West Tennessee, Chester County boasts an abundance of outdoor activities. Whether you’re hiking the trails of Chickasaw State Park or enjoying a leisurely day of fishing on the river, nature enthusiasts will find plenty to love. The county's lush greenery and tranquil surroundings provide a perfect backdrop for family picnics, weekend getaways, and peaceful living.

Chester County is also steeped in history, with charming small towns like Henderson and Bolivar that showcase the area’s rich heritage. Explore local shops, dine at family-owned restaurants, and immerse yourself in the vibrant culture that defines this community. The annual events, such as the Chester County Fair, bring residents together, celebrating local talent, agriculture, and crafts.

Education is a priority here, with quality schools and a commitment to fostering a supportive learning environment for children. The county's friendly atmosphere makes it easy to build connections and friendships, ensuring that newcomers feel right at home.

With its affordable housing options, beautiful landscapes, and a strong sense of community, Chester County is more than just a place to live; it’s a place to thrive. Come discover the charm of Chester County, where your dream home awaits amidst the beauty of Tennessee!

Newest Listings in Chester County

425B Second St, Henderson $70,000

Rare investment opportunity in the heart of Henderson! This historic home sits on approximately 1.2 acres in an established neighborhood and offers tremendous potential. ...

3 Beds
2 Baths
3302409 MLS
ACTIVE Status
1.2 Acres
38340 Zip Code

460 Kendyl Cv, Henderson $224,000

Unlock the Potential at 460 Kendyl Cove, Henderson, TN! Bring your vision and transform this 3-bedroom, 2-bath home offering 1,471 square feet on a spacious half-acre lo...

3 Beds
2 Baths
3298153 MLS
ACTIVE Status
0.44 Acres
38340 Zip Code

3280 Pleasant Springs Rd, Pinson $145,000

If you've been searching for an affordable home where you can simply unpack your boxes and make it your own over time, this may be exactly what you've been waiting for. S...

2 Beds
1 Baths
3287898 MLS
ACTIVE Status
1 Acres
38366 Zip Code

5885 State Route 225, Henderson $135,000

Welcome to 5885 State Route 225, Henderson, TN—a fantastic opportunity to own a solid brick home on approximately 2 acres. Offered at just $135,000, this property present...

3 Beds
2 Baths
3278521 MLS
ACTIVE Status
1.8399999999999999 Acres
38340 Zip Code

Arl Bailey Road, Finger $169,900

Located entirely in Chester County, TN, this approximately 50.1 acre parcel was surveyed in 2021 and features roughly a quarter mile of road frontage with power and fiber...

3247974 MLS
ACTIVE Status
50.1 Acres
38334 Zip Code

320 Benson Rd, Reagan $245,000

Welcome home to this beautifully updated 3-bedroom, 2-bath property nestled on 2.17 acres of peaceful, wooded surroundings! This home features an inviting open floor plan...

3 Beds
2 Baths
3246905 MLS
ACTIVE Status
2.17 Acres
38368 Zip Code

2800 Plainview Road, Henderson $200,000

Discover your own private retreat on this secluded 65+ acre rural paradise. Featuring pristine woodlands and the peaceful flow of Jacks Creek winding through the property...

3230998 MLS
ACTIVE Status
65.9 Acres
38340 Zip Code

60 Proctor Rd, Henderson $2,100,000

Located in Henderson, Tennessee, this exceptional luxury estate offers upscale living and a premier equestrian lifestyle on approximately 30 private acres surrounded by w...

4 Beds
5 Baths
3230940 MLS
ACTIVE Status
30 Acres
38340 Zip Code

454 White Ave, Henderson $199,900 ▼

Adorable 3 br Brick home sitting on large city lot with lots of character, Built ins and Mantle in living room, Hardwood floors throughout, Newly remodeled Kitchen with ...

3 Beds
1 Baths
3230112 MLS
ACTIVE Status
0.5 Acres
38340 Zip Code

100 Mary Kate Ln, Henderson $410,000 ▼

Located in an established and desirable Henderson neighborhood, this spacious home offers the perfect blend of suburban comfort, functional living, and sustainable, farm-...

5 Beds
2 Baths
3208441 MLS
ACTIVE Status
1 Acres
38340 Zip Code

S Hwy 22A, Enville $480,000

Don’t miss this rare opportunity to own 143.34 unrestricted acres in a fantastic location just off Hwy 22 in Enville, Tennessee. This versatile tract offers convenient ac...

3183906 MLS
ACTIVE Status
143.34 Acres
38332 Zip Code

Enville Road, Henderson $95,000

Own 10.30 fully wooded acres with total privacy in Sweet Lips, Tennessee. This unrestricted property features mature oak and pine hardwoods, flat terrain with only 1-5% s...

3183286 MLS
ACTIVE Status
10.3 Acres
38340 Zip Code