N/A Homes with Chester County High School

Welcome to Chester County, Tennessee, where charming homes and a vibrant community come together to create the perfect place to call home. Nestled in the heart of this picturesque county, you’ll find a variety of residential options that cater to families, retirees, and everyone in between. With its rolling hills, lush landscapes, and friendly atmosphere, Chester County offers a serene escape from the hustle and bustle of city life, while still providing convenient access to essential amenities.

One of the standout features of living in Chester County is its proximity to Chester County High School. This well-regarded institution is known for its commitment to academic excellence and a supportive learning environment. Families with school-aged children will appreciate the opportunity for their kids to receive a quality education just a stone's throw away from home. The school also fosters a strong sense of community through various extracurricular activities, ensuring that students can thrive both in and out of the classroom.

The homes in Chester County are as diverse as the families that inhabit them. From charming single-family residences to spacious modern builds, there’s something to suit every taste and budget. Many properties boast beautiful yards and inviting outdoor spaces, perfect for family gatherings or peaceful evenings under the stars.

Whether you’re looking to settle down in a welcoming community or searching for a place that offers a great education for your children, Chester County is the ideal destination. Discover your dream home in this delightful corner of Tennessee today!

Newest N/A Homes with Chester County High School

$3,499,000

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

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 features an open, expansive layout, high-end finishes, and sweeping views of the surrounding natural beauty. It offers an exceptional blend of sophistication, style and functionality. It boasts 5 spacious bedrooms, 4 full bathrooms and 4 half bathrooms. The home provides ample space for both relaxation and entertainment. For those who appreciate fine wines and spirits, there is a custom built wet bar with high end finishes, perfect for entertaining guests. A state-of-the-art home theatre room offers a cinematic experience with plush seating and surround sound. After a great workout in the dedicated fitness area you can find relaxation and rejuvenation in the newly added yoga room. The spiral staircase situates itself perfectly in the home but feel free to utilize the elevator that brings you up and down from each floor. Step outside and discover your own personal paradise. A beautifully designed pool and hot tub overlook the tranquil, spring fed lake . A brand new 52'x84' barn was just added to the property and could be built into a 2nd home on the property. Full concrete flooring throughout and full gutter install on the entire barn. Each side of the barn has newly added lean to's. Hardwired external recessed lighting on porch overhangs and installed 5 BR septic, water and 100 amp electric. An additional, brand new 30'x43' barn was just added to the property. 725 sqft of the barn is finished and ready to be used as an in-law suite, guest house, or groundskeeper quarters. The remainder of the barn is a 2 car garage with an upstairs loft. This building was built in 2025 and has its own 2 bedroom septic in place.There is a total of 9 garage doors. There is enough indoor space for an estimated 14 + cars, ideal for a car collector. There's also a new greenhouse with water and electric. 3 total RV hookups

140 Lake Shore Lane, Henderson

$99,900

3333534 MLS ⋅ ACTIVE Status ⋅ 9.05 Acres ⋅ 38368 Zip Code

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 50 feet of county road frontage, this land offers an excellent opportunity to create your own private retreat, homestead, or recreational getaway. With no buildings currently on the property, you have a blank canvas to bring your vision to life. County water is available at the road, while a septic system and well (if desired) will need to be installed. A perc test has not been completed, giving buyers the opportunity to evaluate the property based on their intended use. No known restrictions provide added flexibility for your future plans. Located near Reagan, you'll enjoy the quiet charm of country living while remaining within easy driving distance of Lexington, Parsons, and Jackson, where you'll find shopping, dining, healthcare, and everyday conveniences. Outdoor enthusiasts will appreciate nearby access to the Natchez Trace State Park, offering miles of hiking and horseback riding trails, camping, fishing, boating, and beautiful scenery. The area is also close to the Tennessee River and Beech Lake, providing even more opportunities for outdoor recreation. Whether you're looking to build your dream home, establish a weekend getaway, or invest in Tennessee land, this 9.05-acre property offers the space, privacy, and potential to make it your own.

Center Point Rd S, Reagan

$159,900

3247974 MLS ⋅ ACTIVE Status ⋅ 50.1 Acres ⋅ 38334 Zip Code

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 internet already available via the utility easement on the property. A septic system and well would be needed, with local well drillers indicating water is typically found at approximately 80 to 100 feet, and the property also benefits from a year round spring. With no known HOA or deed restrictions, limited surrounding development, and easy access to nearby Henderson, Jackson, and other West Tennessee communities, this property offers an ideal blend of rural living and modern convenience. Seller financing is available!

Arl Bailey Road, Finger

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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.