Chester County TN Homes for Sale

• 

  

  

  /22

  $159,900

  • 4 Beds
  • 2 Baths
  • 2,138 Sq Ft

  456 Galbraith Ave, Henderson, TN 38340

  Expanded ranch-style home in Henderson offering over 2,100 sq ft and multiple living areas. Rehab needed, but strong potential with 4 bedrooms, 2 baths, living room, dining room, den, and bonus room or office. Fenced corner lot with deck and storage building. Convenient to downtown and the college campus. Sold as-is. Seller requires 2-3 business days to respond to all offers. Cash or

  John Alsobrook Pritchard Realty

  456 Galbraith Ave, Henderson, TN 38340
• 

  

  

  /5

  $20,000

  • Land
  • 1 Acre
  • $20,000 per Acre

  00 Deerfield Loop, Henderson, TN 38340

  Take a look at this beautiful lot in WestChester Hills, West of Henderson, and 3 blocks from West Chester Elementary. Wonderful area to build a home and raise a family. You can build a great home with a basement or a tornado area. Just lok at this look and we will go from there.

  Linda Carter Casey Realtors

  00 Deerfield Loop, Henderson, TN 38340
• 

  

  

  /67

  $815,000

  • 4 Beds
  • 3.5 Baths
  • 3,314 Sq Ft

  215 Benson Rd, Reagan, TN 38368

  Experience peaceful country living on 40 breathtaking acres with this beautifully updated home that blends modern elegance with rural charm. This spacious residence offers 3 generously sized bedrooms, along with a second large living area upstairs featuring an additional bedroom, private bathroom, and convenient storage room—perfect for guests. The kitchen has been thoughtfully renovated and

  Heather Pierce Coldwell Banker Southern Realty

  215 Benson Rd, Reagan, TN 38368
• 

  

  

  /6

  $20,000

  • Land
  • 1.18 Acres
  • $16,949 per Acre

  Lot 23 Timberwood Cove, Henderson, TN 38340

  Nice residential lot in great location! This 1.18 ac lot in Creekside Estates is waiting for your dream home!

  Tara Joyner BHGRE Conner Brownsville

  Lot 23 Timberwood Cove, Henderson, TN 38340
• 

  

  

  /17

  $590,000

  • Land
  • 217.58 Acres
  • $2,712 per Acre

  0 Garland Rd, Henderson, TN 38340

  217 ACRES ALONG THE FORKED DEER RIVER - PRIME TURKEY, DEER, AND DUCK HUNTING. Located just north of Chester County and adjacent to the backside of Pinson Mounds State Archaeological Park, this 217+- acre tract is an outdoorsman's dream. With approximately a mile of river frontage and a natural habitat that consistently holds wildlife, you'll find exceptional turkey, deer and duck hunting

  Tiffany Elder Porchlight Realty West TN

  0 Garland Rd, Henderson, TN 38340
• 

  

  /15

  $143,500

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft

  629 Luray Ave, Henderson, TN 38340

  Great home for a family with a wonderful price or A GREAT INVESTMENT PROPERTY. 3 br., 1 bath, eat in kitchen, large living room, laundry room, covered front porch, large deck on back, Carport with a storage room. GREAT LOT. This is a must see. Close to downtown, stores and Freed Hardeman

  Linda Carter Casey Realtors

  629 Luray Ave, Henderson, TN 38340
• 

  

  /69

  $598,500

  • 4 Beds
  • 3.5 Baths
  • 3,426 Sq Ft

  614 Oneal Ln, Henderson, TN 38340

  This beautiful home is located in one of the most desirable subdivisions in town — a wonderful walking neighborhood with easy access to Jackson. Built by the former owner of City Lumber Co., it features top-quality materials and thoughtful design throughout. Enjoy a newly paved circular driveway, large front yard, cozy living spaces. Spacious master suite with private patio, his and her bathroom,

  Craig Casey Casey Realtors

  614 Oneal Ln, Henderson, TN 38340
• 

  

  /51

  $990,000

  • 5 Beds
  • 4 Baths
  • 3,035 Sq Ft

  2490 Old Friendship Rd, Finger, TN 38334

  Spacious four-bedroom single-family home in Kalamazoo offering a value-add opportunity for investors. The home features living space, one bathroom, and an existing garage, providing a solid layout for renovation and repositioning. The sale includes two parcels totaling approximately 0.36 acres, including the neighboring corner lot, adding additional land value and flexibility. Parcel IDs

  Ralph Harvey LISTWITHFREEDOM.COM

  2490 Old Friendship Rd, Finger, TN 38334
• 

  

  /11

  $95,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  454 Fourth St, Henderson, TN 38340

  Great investment property in the heart of Henderson, close to schools, shopping and dining. Sold AS IS-WHERE IS.

  Dian Blankenship Greer Real Estate Group

  454 Fourth St, Henderson, TN 38340
• 

  

  /32

  $437,500

  • Land
  • 175 Acres
  • $2,500 per Acre

  3392 Sand Mountain Rd, Enville, TN 38332

  175± acres located on Sand Mountain in Chester County, TN. This tract offers more than 500 feet of frontage on Sand Mountain Rd with electricity and fiber internet available. The property includes approximately 155 acres of 7-year-old loblolly pine and 20 acres of aging hardwoods and pine. Good internal road system in place. Excellent deer and turkey hunting. The property sits along the Tennessee

  Austin Carroll Tutt Land Company

  3392 Sand Mountain Rd, Enville, TN 38332
• 

  

  /13

  $159,000

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft

  150 Jacks Creek St, Henderson, TN 38340

  Location Location Location.. Home perfectly located in the heart of Henderson! This property offers unbeatable convenience, just a short walk to Freed-Hardeman University, local restaurants, coffee shops, and all the best area amenities. Whether you’re looking for a personal home or an investment opportunity, this prime location delivers. It has a metal roof, and an Acre Land. Location truly is

  Sana Shah The Agency Nashville, LLC

  150 Jacks Creek St, Henderson, TN 38340
• 

  

  /53

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 3,912 Sq Ft

  1620 Dry Creek Rd, Pinson, TN 38366

  Welcome home to 46 acres of heaven in West Tenn. with a beautiful view of it's own private lake. Conveniently located between Memphis & Nashville. Built by renowned architect, Clay Chapman. This stunning brick & timber frame chateau is built atop 4 luxury horse stables. This remarkable masterpiece sits in the middle of a mature, hardwood & pine forest, providing total seclusion from the outside

  Jodie Parrish RE/MAX Realty Source

  1620 Dry Creek Rd, Pinson, TN 38366
• 

  

  /14

  $58,000

  • Land
  • 2 Acres
  • $29,000 per Acre

  0 Hill Ave, Henderson, TN 38340

  2 acres outside the city of Henderson and zoned for residential use. City water and natural gas are available, but a septic system is required. The lots are under the jurisdiction of the local Planning Committee to protect your investment. A soil map has been completed & suggests it is suitable for a one-bedroom home. Shipping containers on the property do not convey. It is a corner lot with road

  Ashton Roberts Molly Moore Realty

  0 Hill Ave, Henderson, TN 38340
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  /9

  $35,750

  • Land
  • 7.44 Acres
  • $4,805 per Acre

  000 Stewart Rd, Henderson, TN 38340

  7.44 serene, wooded acres in Chester County offer endless possibilities for unrestricted living. Create your dream retreat in this peaceful rural setting, where the blank canvas allows you to design and build as you please. Embrace the tranquility of country living on this spacious parcel of land. 7.44 acres of beautiful rural wooded land in Chester County offering endless possibilities for

  Larry Roberts Casey Realtors

  000 Stewart Rd, Henderson, TN 38340
• 

  

  /21

  $399,900

  • Land
  • 98.23 Acres
  • $4,071 per Acre

  0 Highway 22 A, Enville, TN 38332

  Don't miss this rare opportunity to own 98.23 unrestricted acres in a fantastic location just off Hwy 22 in Enville, Tennessee. This versatile tract is ideally situated with convenient access to Lexington, Henderson, and Adamsville. Whether you're looking to build your dream home, develop a recreational retreat, or invest in land with excellent potential, this property fits the bill. With

  Lori Yarbro Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
• 

  

  /16

  $169,900

  • 2 Beds
  • 1 Bath
  • 956 Sq Ft

  320 Clayton Rd, Finger, TN 38334

  Escape to the country in this charming 2 bedroom, 1 bathroom retreat, perfectly situated on 1 serene acre! Inside, enjoy a split floor plan for maximum privacy, plus an eat-in kitchen equipped with appliances for effortless meal prep. A spacious laundry room adds convenience, while the rest of the home boasts plenty of natural light and cozy charm. Step outside to unwind on the inviting covered

  Brooke Redmon Benton Action Realty

  320 Clayton Rd, Finger, TN 38334
• 

  

  /28

  $229,000

  • 4 Beds
  • 2 Baths
  • 1,949 Sq Ft

  241 Crook Ave, Henderson, TN 38340

  Vintage 4-bedroom, 2-bath home that's been totally revamped! With new flooring, fresh paint, and cool light fixtures, it's ready for you to move right in. It's super close to Freed Hardeman and all the fun stuff downtown Henderson has to offer. You'll love the big, roomy spaces with tons of storage for all your stuff. The kitchen's got shiny stainless steel appliances that are perfect for

  Katie Mitchell Townsend Compass RE

  241 Crook Ave, Henderson, TN 38340
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  /4

  $48,000

  • Land
  • 5.2 Acres
  • $9,231 per Acre

  00 Lofton Rd, Enville, TN 38332

  Analytical: Unveiling 5.25 acres of unrestricted land in Enville, TN, this property is tailored for off the grid living. The front portion boasts a flat and clear terrain, while the back section is densely wooded. This juxtaposition of open space and seclusion creates a harmonious blend of possibilities for the prospective buyer seeking a versatile setting. Explore the untapped potential of this

  Larry Roberts Casey Realtors

  00 Lofton Rd, Enville, TN 38332
• 

  

  /25

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,354 Sq Ft

  707 Mifflin Avenue Extension, Henderson, TN 38340

  Welcome home to this beautifully maintained 3-bedroom, 2-bath residence located in the heart of the city. Designed with an open floor plan, this home offers seamless flow between the living, dining, and kitchen areas—perfect for everyday living and entertaining. There's plenty of space for a large dining table, complemented by a kitchen peninsula with seating for casual meals and gatherings.

  Melanie Malone Crye-Leike Elite

  707 Mifflin Avenue Extension, Henderson, TN 38340
• 

  

  /13

  $168,000

  • 3 Beds
  • 1 Bath
  • 1,071 Sq Ft

  576 Luray Ave, Henderson, TN 38340

  This charming, renovated brick home presents a wonderful opportunity for first-time buyers or anyone looking to downsize. Beautiful mature trees offer plenty of shade in both the front and backyard, perfect for unwinding on your deck or hosting a fun family BBQ. The house comes with a refrigerator, washer, and dryer, making move-in day easier. You'll also find many thoughtful upgrades, including

  Elizabeth Burlew eXp Realty, LLC

  576 Luray Ave, Henderson, TN 38340
• 

  

  /17

  $210,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  5060 Enville Rd, Henderson, TN 38340

  Home comes with a Home Warranty. Welcome to 5060 Enville Rd. Henderson, TN. This charming 3bed 2bath farmhouse seamlessly blends comfort with rustic appeal. This home highlights a huge master bedroom perfect for your retreat after a busy day, a brand new roof that ensures years of worry-free living, 2 acres of beautiful landscape, a poultry coop and a workshop with electricity ready for any DIY

  Braden Mileham Blue Suede Realty

  5060 Enville Rd, Henderson, TN 38340
• 

  

  /14

  $42,000

  • Land
  • 5.61 Acres
  • $7,487 per Acre

  TRACT 5 Tennessee 225, Henderson, TN 38340

  $1000 DOWN - OWNER FINANCING - NO CREDIT CHECKS TRACT 4 STATE ROUTE 225 BETHEL SPRINGS, TN 5.61 ACRES - $42K - $1000 DOWN & $325/MTH BEAUTIFUL TENNESSEE LAND IN CHESTER COUNTY, TN. NICE 5.05 ACRES LOT SR 225 BETHEL SPRINGS TN. LAND IS UNRESTRICTED POWER & WATER IS AVAILABLE THIS IS VERY USABLE LAND! Build a house, mobile home or many different uses If you notice in the survey, there is a gas

  Timothy Crane 2 Cranes Realty

  TRACT 5 Tennessee 225, Henderson, TN 38340
• 

  

  /10

  $100,000

  • Land
  • 22.82 Acres
  • $4,382 per Acre

  0 Old Lula Rd, Reagan, TN 38368

  Discover over 22 acres of secluded, wooded, paradise with paved road frontage. A rare combination of convenience and privacy. This property isi deal for a weekend hunting retreat, recreational escape. or the perfect spot to build your dream home in the heart of nature.

  ERICA MAXWELL Tiffany Jones Realty Group, LLC

  0 Old Lula Rd, Reagan, TN 38368
• 

  

  /14

  $90,000

  • Land
  • 6.6 Acres
  • $13,636 per Acre

  00 Ridgewood Dr, Henderson, TN 38340

  One of the last buildable lots in the highly sought-after Oak Ridge Estates subdivision! This beautiful 6.6-acre tract offers space, privacy, and upscale country living, located in the county yet surrounded by well-maintained homes and great neighbors. The property features underground utilities and is already approved for a 4-bedroom home, making it truly build-ready. Light subdivision

  Dustin Insell Coldwell Banker Southern Realty

  00 Ridgewood Dr, Henderson, TN 38340
• 

  

  /10

  $182,900

  • 5 Beds
  • 2 Baths
  • 1,917 Sq Ft

  325 Jennings Rd, Reagan, TN 38368

  Good area in rural area. NEW septic system just installed. New flooring installed of both carpet and lvp. House is empty and ready for the new owners.

  Craig Casey Casey Realtors

  325 Jennings Rd, Reagan, TN 38368
• 

  

  /46

  $565,000

  • 4 Beds
  • 3 Baths
  • 3,013 Sq Ft

  95 Teague Trace Ln, Luray, TN 38352

  Looking for a beautiful home with room to spread out? Welcome to 95 Teague Trace, a stunning four-bedroom, three-bath brick home set on five open acres shaded by mature, majestic oak trees. Located in a quiet, highly sought-after neighborhood, this exceptional property offers the perfect balance of luxury, comfort, and privacy. A BRAND-NEW ROOF installed August 2025 adds peace of mind and

  Jennifer Maness-Scott Stellar Realty Group

  95 Teague Trace Ln, Luray, TN 38352
• 

  

  /13

  $152,075

  • Land
  • 77 Acres
  • $1,975 per Acre

  1700 Grooms Rd, Henderson, TN 38340

  77+/- acres of diverse timber and recreational/hunting land waiting for your next adventure. This property offers an excellent mix of timber stands for investment potential: 15+/- acres of aging hardwoods, 18+/- acres of 13 year-old pine, 13+/- acres of 5 year-old pine, and 30+/- acres of naturally regenerating hardwoods. The rolling and sloping terrain and terriffic diversity creates ideal

  Austin Carroll Tutt Land Company

  1700 Grooms Rd, Henderson, TN 38340
• 

  

  /24

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,501 Sq Ft

  1980 Sanford Rd, Henderson, TN 38340

  Take a look at this house, quite a bit of remodeling done. It has 3 br.,plus den/office/or nursery, 2 full baths, dining room, nice Living room and more. Nice size lot. It has an external storm shelter and a storage/workshop. call for a showing

  Linda Carter Casey Realtors

  1980 Sanford Rd, Henderson, TN 38340
• 

  

  /5

  $149,900

  • Land
  • 0 Acre

  1170 Keene Rd, Enville, TN 38332

  Discover a rare opportunity to own a combined 46+ acres of prime land in scenic Enville, Tennessee—featuring two parcels being sold together, one in Chester County and the other in McNairy County. Whether you're seeking a private rural homesite, recreational retreat, or long-term investment, this versatile offering delivers exceptional value and potential. The first parcel, located at 1170 Keen

  Nathan Lilly Lilly Realty

  1170 Keene Rd, Enville, TN 38332
• 

  

  /16

  $469,385

  • Land
  • 241 Acres
  • $1,948 per Acre

  0 Roby Trail, Henderson, TN 38340

  Located north of Hwy 100, only 80 miles east of Memphis and 30 minutes south of Jackson, the Deberry Tract in Chester County, Tennessee, is an exceptional hunting and recreational property! The tract is fully wooded with approximately 1/3 of the acreage in mature merchantable loblolly pine. The remainder of the timber is white oak dominated hardwoods that were lightly thinned in 2015. Water

  Jared Walker Compass South, Inc.

  0 Roby Trail, Henderson, TN 38340
• 

  

  /58

  $4,500,000

  • 5 Beds
  • 8 Baths
  • 8,264 Sq Ft

  140 Lake Shore, Henderson, TN 38340

  Nestled on 52 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. Step outside and discover your own personal paradise. A beautifully designed pool and hot tub overlook the tranquil,

  Brandon Pendergrass Hayden Outdoors LLC

  140 Lake Shore, Henderson, TN 38340
• 

  

  /5

  $16,500

  • Land
  • 1.44 Acres
  • $11,458 per Acre

  19 Chisum Ln, Beech Bluff, TN 38313

  Lovely 1+ acre lot in Chester County. Chester County Schools. County taxes only. Some restrictive covenants, Perfect for your dream home. Property is at the end of a cul de sac. Aeneas internet available. Call Larry for your private showing 731-267-1580.

  Larry Roberts Casey Realtors

  19 Chisum Ln, Beech Bluff, TN 38313
• 

  

  /47

  $1,350,000

  • 5 Beds
  • 4 Baths
  • 3,798 Sq Ft

  280 Harris Ln, Henderson, TN 38340

  LOOKING FOR SECULSION. THEN THIS IS IT. BEAUTIFUL 180 ACRES OF PARADISE . LOCATED CLOSE TO CHICKASAW PARK, THIS PIECE OF HEAVEN HAS SO MUCH TO OFFER, HUNTERS PARADISE (GREAT LODGE POTENTIAL, AN AIR B/B,) MULTIPLE FAMILY AREAS BESIDE THE MAIN HOME, (MAIN HOME IS A CUSTOM BUILT MODULAR HOME ON A PERMANENT FOUNDATION), 3 BR.,, 2 BATHS, DEN W/FIREPLACE, LIVING ROOM W/FIREPLACE, KITCHEN WITH BREAKFAST

  Linda Carter Casey Realtors

  280 Harris Ln, Henderson, TN 38340
• 

  

  /22

  $239,900

  • 3 Beds
  • 2 Baths
  • 1,895 Sq Ft

  414 Galbraith Ave, Henderson, TN 38340

  This modern remodeled 3-bedroom, 2-bath home features vinyl siding, a carport with extra storage ideal for a workshop, and spacious rooms with a large backyard. Inside, it offers new flooring and fresh paint throughout, plus a master suite with a double vanity and a walk-in tiled shower. A turnkey property that combines modern updates with practical amenities for versatile living. This modern

  Zach Hannis Casey Realtors

  414 Galbraith Ave, Henderson, TN 38340
• 

  

  /3

  $375,000

  • Land
  • 60 Acres
  • $6,250 per Acre

  795 Hill Ave, Henderson, TN 38340

  You have access from three locations, 1) Williams Rd. 2) A 55 ft. strip between 751 and 777 Hill Ave, and 3) End of Mason Street. This is approximately 60-acre tract more or less that is behind a 10-acre tract at 817 Hill Avenue Ext. and runs from the end of Mason St. to Williams Rd. approximately 2,445 feet from Williams rd to Mason Street. This tract is an irregular shape. Survey available on

  Garry Carroll Crye-Leike Elite

  795 Hill Ave, Henderson, TN 38340
• 

  

  /24

  $219,000

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  320 Benson Rd, Reagan, TN 38368

  2.17 Acres country living. Newly updated kitchen with granite countertops, stainless appliances, cabinets, coffee bar, and open to living room, rec room (which could be 4th bedroom). Main bedroom features private bath, double sinks, shower/commode room, 5x5 closet, and private access door to backyard. Outside was updated with siding, cedar posts, and shutters to match. 14x22 screened in porch

  Andrea Crawford RE/MAX Unlimited

  320 Benson Rd, Reagan, TN 38368
• 

  

  /24

  $774,000

  • 5 Beds
  • 4.5 Baths
  • 4,280 Sq Ft

  715 Roundtree Ln, Beech Bluff, TN 38313

  This beautiful home features 5 bedrooms, 4 1/2 baths, wrap around porch, 9 ft ceilings on main level.... 13 + or - park like acres, 2 acre stocked pond... Koi pond and firepit in backyard...this fabulous home features 3 stories, full basement with bedroom, bath, den and office space....main floor features large eat-n-kitchen, formal dining, large greatroom with fireplace, built in bookcases and

  Joyce Addison Coldwell Banker Southern Realty

  715 Roundtree Ln, Beech Bluff, TN 38313
• 

  

  /7

  $25,000

  • Land
  • 2 Acres
  • $12,500 per Acre

  1575 Hurst Rd, Henderson, TN 38340

  Enjoy country living on this 2 acre lot, only 20 minutes from town of Henderson. Unlimited potential awaits you at this property!

  Linda Carter Casey Realtors

  1575 Hurst Rd, Henderson, TN 38340
• 

  

  /18

  $39,900

  • Land
  • 5.5 Acres
  • $7,255 per Acre

  Tract 3 Tennessee 225, Bethel Springs, TN 38315

  A great opportunity for unrestricted land and one of 2 possible lots in Chester Co. 5.5 acres on Hwy 225. Is your dream: a getaway with a trailer or mobile home, small pasture for farm animals or an escape to a quiet home in the country with no restrictions? This lot has 5.5 acres and 140 feet of road frontage (similar to the other 3). Tracts 1,4,5,6,7 & 8 have been sold. Tracts 2 & 3 are still

  Mike Singleton McIver Land & Realty

  Tract 3 Tennessee 225, Bethel Springs, TN 38315
• 

  

  /37

  $250,000

  • 3 Beds
  • 2 Baths
  • 1,682 Sq Ft

  841 Sanford St, Henderson, TN 38340

  Brick Beauty with Shop on Almost 2 Acres in Henderson, TN! Welcome home to this spacious 3-bedroom, 2-bath brick home offering over 1,600 sq. ft. of living space right inside the city limits of Henderson! You’ll love the peaceful setting with nearly 2 acres of land — plenty of room to spread out while still being close to everything. Step inside to find a warm and inviting floor plan, perfect for

  Erica Maxwell Tiffany Jones Realty Group

  841 Sanford St, Henderson, TN 38340

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