Chester County Homes for Sale

Chester County, located in the state of Tennessee, is a beautiful and vibrant county that offers a wide range of opportunities for homebuyers. With its rich history, charming small towns, and stunning natural landscapes, Chester County is a wonderful place to call home.

If you are looking for homes for sale in Chester County, you are in luck. This county boasts a diverse real estate market with a variety of options to suit different preferences and budgets. Whether you are searching for a cozy single-family home in a peaceful neighborhood or a spacious farmhouse with acres of land, you will find plenty of choices in Chester County.

The homes for sale in Chester County offer not only comfortable living spaces but also access to a range of amenities and attractions. From excellent schools and healthcare facilities to recreational parks and shopping centers, this county has everything you need for a convenient and fulfilling lifestyle.

In addition to its residential offerings, Chester County also boasts a strong sense of community and a welcoming atmosphere. The friendly residents, community events, and local businesses contribute to the county's vibrant and close-knit environment.

If you are considering making Chester County your home, now is the perfect time to explore the available homes for sale. With its picturesque landscapes, friendly communities, and affordable real estate options, Chester County offers a unique and desirable living experience.

Newest Chester County Homes for Sale

$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

$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

$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

$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

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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.