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

140 Lake Shore Lane, Henderson $3,499,000

Nestled on 51 pristine acres, this sprawling 8,264 square-foot estate offers unparalleled luxury and privacy. A true masterpiece of design and craftsmanship, the home fea...

5 Beds
8 Baths
3529035 MLS
ACTIVE Status
51 Acres
38340 Zip Code

80 Proctor Rd, Henderson $899,900

Discover a gorgeous 108 acres offering the perfect blend of open pasture, water, woods, and functionality. The property features cross fencing with seperated pastures, po...

3506115 MLS
ACTIVE Status
108 Acres
38340 Zip Code

Center Point Rd S, Reagan $99,900

Escape to the peace and beauty of rural Tennessee with this 9.05-acre surveyed property in Reagan. Featuring a blend of wooded terrain, rolling slopes, and approximately ...

3333534 MLS
ACTIVE Status
9.05 Acres
38368 Zip Code

460 Kendyl Cv, Henderson $209,000 ▼

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

Arl Bailey Road, Finger $159,900 ▼

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

454 White Ave, Henderson $189,900 ▼

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

5030 Sand Mountain Rd, Enville $89,900 ▼

Beautiful 12+/- acre parcel located on Sand Mountain Road in Enville. This property offers a great opportunity to build your dream home or place a manufactured home in a ...

3147736 MLS
ACTIVE Status
12 Acres
38332 Zip Code

341 Melodie Cir, Henderson $242,500 ▼

Welcome to 341 Melodie Circle in Henderson, Tennessee — where comfort, updates, and privacy come together. This well-maintained home features beautifully updated bathroo...

3 Beds
2 Baths
3136958 MLS
ACTIVE Status
0.71 Acres
38340 Zip Code

S State Route 22A, Enville $225,550

Escape to Tennessee Country Living on this 45.11 parcel situated in Enville, TN. Ideally located just 20 miles from Lexington, Henderson, and Savannah, TN, this property ...

3047408 MLS
ACTIVE Status
45.11 Acres
38332 Zip Code