Chester County Real Estate

Chester County is a beautiful county located in the state of Tennessee. The county is home to rolling hills, lush forests, and numerous rivers and streams. The county is also known for its vibrant history and culture. From the historic downtown of Henderson to the picturesque town of Hendersonville, Chester County has something for everyone.

The area is known for its natural beauty and outdoor activities. The county is home to several parks and trails, including the Ocoee River Trail, which offers scenic views of the surrounding landscape. There are also plenty of opportunities for fishing, camping, and other outdoor activities.

The county also features a variety of housing options. From single-family homes to condos and townhomes, there is something for everyone in Chester County. There are also plenty of businesses and amenities available, including shopping, dining, and entertainment.

Chester County is a great place to call home. Whether you're looking to buy or rent, the area has something for everyone. With its natural beauty, vibrant history, and plenty of amenities, Chester County is a great place to live.

Newest Listings in Chester County

$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

$899,900

3506115 MLS ⋅ ACTIVE Status ⋅ 108 Acres ⋅ 38340 Zip Code

Discover a gorgeous 108 acres offering the perfect blend of open pasture, water, woods, and functionality. The property features cross fencing with seperated pastures, ponds, a shop with two bays, and underground utilities already in place. Wooded trails wind throughout the acreage, creating opportunities for horseback riding, ATVs, hunting, or simply enjoying the privacy and natural beauty of the land. With ample space for livestock, horses, recreation, or a private estate, this property offers incredible versatility and room to make it your own. A rare opportunity to own substantial acreage with key improvements already in place!

80 Proctor Rd, 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

$209,000

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

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 lot into the home of your dreams. Whether you're a first-time homebuyer ready to build equity or an investor looking to expand your portfolio, this fixer-upper is packed with opportunity and endless possibilities. Conveniently located in the desirable Chester County School District, the home is less than a mile from local schools and just minutes from shopping, restaurants, medical services, and Freed-Hardeman University. Nearby schools include East Chester Elementary, Chester County Middle School, Chester County Junior High, and Chester County High School. Residents also enjoy easy access to grocery stores, local boutiques, parks, and everyday conveniences. Don't miss your chance to invest in a property with great bones, a prime location, and unlimited potential. Schedule your showing today and imagine the possibilities!

460 Kendyl Cv, Henderson

$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

$189,900

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

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 all new appliances, cabinets, laminate flooring and a Bar. Master has 2 large closets. Home has newer windows, metal roof, outbuilding for storage, new landscaping and a concrete driveway. Only a few blocks from Freed Hardeman University. Owner / Agent .

454 White Ave, Henderson

$410,000

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

Located in an established and desirable Henderson neighborhood, this spacious home offers the perfect blend of suburban comfort, functional living, and sustainable, farm-to-table functionality. Situated on a generously sized lot, this exceptional property delivers all the infrastructure and charm you need to start your hobby farm from day one without sacrificing the conveniences of neighborhood living. A convenient downstairs room serves perfectly as a home office, playroom, or hobby space. Updates include a newer roof, approximately 3 years old and a brand new water heater as well as new carpet in both primary bedroom and bonus room. The property features a a spacious, privacy-fenced backyard perfectly set up for chickens and animal lovers with chicken coop, run, pasture and run-in shed. The land boasts an expansive, sun-drenched garden footprint ready for your favorite seasonal vegetables or fruit. The homeowner is generously offering a $5,000 carpet/paint allowance.

100 Mary Kate Ln, Henderson

$480,000

3183906 MLS ⋅ ACTIVE Status ⋅ 143.34 Acres ⋅ 38332 Zip Code

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 access to Lexington, Henderson, and Adamsville while still providing the privacy, nature, and wide-open space buyers are looking for. With electricity available at the road and multiple ideal building sites, this property is perfect for building your dream home, creating a recreational retreat, hunting, or investing in land with excellent potential. With no restrictions, the possibilities are endless—make this property truly your own! Owner financing is available!

S Hwy 22A, Enville

$95,000

3183286 MLS ⋅ ACTIVE Status ⋅ 10.3 Acres ⋅ 38340 Zip Code

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% slope, and 314 feet of road frontage on Enville Road. Only one neighbor borders the western boundary, with undeveloped land surrounding the remaining sides. Power lines and gas service are available at the road. The rare flat topography provides flexible building sites across the entire acreage, unlike typical Tennessee properties limited by steep hillsides. Located 15 minutes from Henderson and 25 minutes from Lexington, with convenient access to Memphis and Nashville. Annual taxes are only $453 with no HOA fees. Survey available with corner stakes and iron pins. Unrestricted zoning allows traditional homes, mobile homes, RV living, or recreational use. Parcel Number: 058 01702 00003058, GPS: 35.40878, -88.52054, Legal Description: 10.3 acres as surveyed by Advanced Land Surveying, Inc. R.L.S. 1999 on September 21, 2004, Conveyance: Warranty Deed (Clean Title). C & J Well Drilling. Pricing structure approximatley $6,575 for the first 100 and then an additional $20 per foot for anything between 100-200; Well covers $375 (Subject to Change). Power available. Requires septic and well. Buyer Due Diligence: We do our best to ensure listing accuracy. However, buyer is responsible to perform their own due diligence and verify all information, contained herein or not, including access and utility accessibility and costs, and physically visit the property. Property is sold “AS IS”. Use this link for driving directions and as a boundary map showing you on the property: https://www.google.com/maps/d/u/0/viewer?mid=1vZOKhhzOysIRbspKUGKBYsdyUQ9DieE&femb=1&ll=35.40782287764651%2C-88.52097726975164&z=15

Enville Road, Henderson

$89,900

3147736 MLS ⋅ ACTIVE Status ⋅ 12 Acres ⋅ 38332 Zip Code

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 peaceful rural setting. Utilities are available at the road making it convenient for future development. Enjoy the privacy of country living while still being within reasonable driving distance to nearby towns and amenities. The property offers road frontage and plenty of space for a home, shop, garden, or recreational use. If you're looking for a quiet place to build or invest in land, this property is worth a look. Acreage per tax records. Buyer/Buyer's Agent to verify all pertinent information including utilities, restrictions, and intended use.

5030 Sand Mountain Rd, Enville

$242,500

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

Welcome to 341 Melodie Circle in Henderson, Tennessee — where comfort, updates, and privacy come together. This well-maintained home features beautifully updated bathrooms, including a primary suite with a tiled walk-in shower complete with a rainfall showerhead for a spa-like experience. The secondary bathroom offers a stylish tub/shower combo with modern plumbing fixtures and updated flooring, providing both functionality and contemporary appeal. Step outside to enjoy an oversized backyard that feels private and peaceful, backing up to open field rather than neighboring homes — the perfect setting for relaxing evenings, entertaining, or simply enjoying the quiet surroundings. Located in Chester County with no city taxes, this property offers the benefit of lower expenses while still being just a short drive to Jackson and nearby shopping, dining, and everyday amenities. If you're looking for updated features, privacy, and convenience all in one package, this home is a must-see.

341 Melodie Cir, Henderson

$225,550

3047408 MLS ⋅ ACTIVE Status ⋅ 45.11 Acres ⋅ 38332 Zip Code

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 offers no restrictions and lies outside city limits, giving you the perfect chance to make your dreams come true. Part of tract has already been cleared and ready to build on. Soil mapping has been done. Call today!

S State Route 22A, Enville

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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.