Chester County TN Homes for Sale

• 

  

  

  /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
• 

  

  

  /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
• 

  

  

  /27

  $359,900

  • 4 Beds
  • 2.5 Baths
  • 2,475 Sq Ft

  2985 Sand Mountain Rd, Enville, TN 38332

  Very well maintained spacious home w/several extra rooms & unfinished basement. Beautiful hardwood floors, sunroom, stone patio, wired workshop. Also, a single wide mobile home on the property that could be converted to rental property or in-law suite. Sits on 2.1 acres, very private, beautiful lot w/circle drive.

  Jodie Parrish RE/MAX Realty Source

  2985 Sand Mountain Rd, Enville, TN 38332
• 

  

  

  /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
• 

  

  

  /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
• 

  

  /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
• 

  

  /26

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  2930 Sanford Rd, Henderson, TN 38340

  This well-maintained 3-bed, 2-bath home is a great fit for first-time buyers who want space, privacy, and manageable monthly expenses. Located in the county, you'll avoid city taxes while still having plenty of room to spread out on 1.54 acres. The property gives you the kind of outdoor freedom that's hard to find—whether you've got pets, kids, hobbies, or just want a quiet place to unwind. The

  Jon Putt Putt Real Estate Advisors

  2930 Sanford Rd, Henderson, TN 38340
• 

  

  /48

  $509,900

  • 4 Beds
  • 3 Baths
  • 3,316 Sq Ft

  515 Ridgewood Dr, Henderson, TN 38340

  This is one of those homes that just feels right the moment you walk in. Offering 4 bedrooms, 3 full baths, and 3,316 heated square feet, there's room to spread out and truly live. The primary suite is on the main level, along with a second bedroom and full bath—perfect for guests, family, or a home office setup. Situated on 1.3 acres, this home is surrounded by beautiful Tennessee hardwoods,

  

  Destiny Burns

  Stellar Realty Group

  (731) 200-6888

  515 Ridgewood Dr, Henderson, TN 38340
• 

  

  /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
• 

  

  /34

  $255,000

  • 4 Beds
  • 2 Baths
  • 1,333 Sq Ft

  2215 State Route 22a S, Jacks Creek, TN 38347

  Country living at its best! 4BR/2BA home on approximately 3 acres. Some recent remodeling including new vanities and countertops in the bathroom, new island in the kitchen, new kitchen appliances and new shelving in the laundry room. New HVAC in 2025. Unrestricted, perfect for a mini farm. Barn and partial fencing already in place. Lot dimensions are approximate.

  

  Jesse Bradley

  Tennessee Valley Realty and In

  (731) 207-4441

  2215 State Route 22a S, Jacks Creek, TN 38347
• 

  

  /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
• 

  

  /15

  $100,000

  • Land
  • 14.09 Acres
  • $7,097 per Acre

  0 Sheila Dr, Henderson, TN 38340

  Calling all existing/new developers, or someone looking for a dream home site to build a single family in Chester County!! This is a PRIME opportunity!! This property was designed to be neighborhood(see subdivision plat in associated docs) and now available for new development. This parcel is mostly wooded, predominately pine, and hasn't been cut in 15 years. Generously priced to sell, in a quiet

  Robert Eatman Hickman Realty Group Inc.-Jack

  0 Sheila Dr, 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
• 

  

  /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
• 

  

  /27

  $299,000

  • 4 Beds
  • 2 Baths
  • 1,922 Sq Ft

  6525 State Route 225, Henderson, TN 38340

  This one sure has style. This 4-bedroom, 2-full-bath home is full of personality, comfort, and thoughtful design. The beautiful kitchen is the heart of the home, offering great flow, eye-catching details, and space to gather. And yes... let's talk about that refrigerator — it's a showstopper. The kind you immediately fall in love with and wish you could take home. Spacious bedrooms, inviting

  

  Destiny Burns

  Stellar Realty Group

  (731) 868-7932

  6525 State Route 225, Henderson, TN 38340
• 

  

  /52

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1310 Inca Rd, Henderson, TN 38340

  Beautifully maintained country retreat on 7.5 acres!This meticulously maintained home is as nice as the day it was built and offers the perfect blend of peaceful country living with convenient access to town. Situated on 7.5 of UNRESTRICTED land, much of it is already cleared and ready for future building. Recent survey on hand.Inside, you’ll find new windows with screens throughout, new

  Jessica Asberry EXIT Realty Blues City

  1310 Inca Rd, Henderson, TN 38340
• 

  

  /7

  $244,900

  • Land
  • 65.9 Acres
  • $3,716 per Acre

  2800 Plainview Rd, Henderson, TN 38340

  Secluded 65+ acre rural oasis with pristine woods, perfect for off-grid living and a peaceful retreat. Endless possibilities await on this vast parcel, ideal for creating your own private sanctuary in nature's embrace. Embrace the tranquility of country living on this undisturbed land, where Jacks Creek flows through, enhancing the scenic beauty.

  Larry Roberts Casey Realtors

  2800 Plainview Rd, Henderson, TN 38340
• 

  

  /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
• 

  

  /24

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  155 Whitley Ave, Henderson, TN 38340

  Welcome to this charming home built in 2023 that blends modern style with comfortable everyday living. This super cute 3-bedroom, 2-bath home features an open-concept floor plan designed for both entertaining and relaxing. The kitchen and living area flow seamlessly together, highlighted by white shaker cabinets, granite countertops throughout, and a roomy walk-in pantry that offers exceptional

  Amanda Driver Blackwell Realty and Auction

  155 Whitley Ave, Henderson, TN 38340
• 

  

  /16

  $209,900

  • 4 Beds
  • 2 Baths
  • 1,248 Sq Ft

  2305 Enville Rd, Henderson, TN 38340

  Enjoy peaceful country living just minutes from town in this beautifully updated 4-bedroom, 2-bath home situated on a picturesque 1-acre lot. Take in stunning views of rolling hills from your property, offering a true sense of space and serenity. The home features new hardwood floors, an updated kitchen with refreshed cabinetry, and a charming wood ceiling that adds warmth and character. The

  Melanie Malone Crye-Leike Elite

  2305 Enville Rd, Henderson, TN 38340
• 

  

  /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
• 

  

  /28

  $574,900

  • 3 Beds
  • 2.5 Baths
  • 2,216 Sq Ft

  10430 Tennessee 100, Henderson, TN 38340

  Your Tennessee Country Escape on 25 AcresIf you’ve been searching for the perfect combination of peaceful country living and convenient access to town, this stunning 25-acre property in Henderson, Tennessee is calling your name. With wide-open land, mature trees, and a beautifully renovated home, this property offers endless possibilities—whether you dream of starting a homestead, creating a

  Joe Cummings

  10430 Tennessee 100, Henderson, TN 38340
• 

  

  /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
• 

  

  /23

  $157,400

  • 3 Beds
  • 1.5 Baths
  • 960 Sq Ft

  1295 Mayfield Rd, Henderson, TN 38340

  Completely renovated 3 bed, 1.5 bath home with brand new roof, siding, windows, HVAC, fixtures, subfloor, and flooring. Fresh paint, doors, and trim provide a modern touch. Benefit from county taxes and a convenient location near Henderson, Jackson, Selmer, and Corinth. This property boasts a circle driveway, covered porches for outdoor relaxation, and sits on over a 1-acre lot. A $2000 appliance

  Linda Carter Casey Realtors

  1295 Mayfield Rd, Henderson, TN 38340
• 

  

  /29

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft

  2130 Hughes Rd, Henderson, TN 38340

  Private Country Living - Enjoy the peace and serenity of the West Tennessee countryside in this beautiful brick home set on approximately 1.87 acres, perfectly nestled among mature trees & accessed by a picturesque rolling driveway. Privacy is a defining feature here, offering a quiet, relaxing retreat surrounded by natural beauty & tranquil country views. This three-bedroom, two-bath home offers

  Alan Castleman Hickman Realty Group Inc.-Jack

  2130 Hughes Rd, 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
• 

  

  /28

  $359,900

  • 4 Beds
  • 2 Baths
  • 1,991 Sq Ft

  110 Harmony Ln, Henderson, TN 38340

  Welcome to 110 Harmony Lane, a beautiful home offering comfort, style, and convenience. The luxury kitchen features elegant granite countertops, perfect for cooking and entertaining alike. This spacious home includes four generously sized bedrooms, each with walk-in closets providing ample storage. Step outside to enjoy the fenced-in backyard, complete with a cozy fire pit—ideal for relaxing

  Brent West Crye-Leike Elite

  110 Harmony Ln, Henderson, TN 38340
• 

  

  /65

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft

  6275 Main St, Enville, TN 38332

  170 Acre Premier Hunting and Recreational Property with Cabin & Shop Chester County, TennesseeThis exceptional 170 acre property in Chester County, Tennessee offers a rare combination of comfortable improvements, diverse timberland, and outstanding recreational value. With paved road frontage along State Route 22A and utilities readily available, this tract is well suited for a turnkey

  Nathan McCollum Mossy Oak Properties Southeast Land & Wildlife, LLC

  6275 Main St, Enville, TN 38332
• 

  

  /30

  $171,900

  • Land
  • 76 Acres
  • $2,262 per Acre

  0 Palestine Ln, Henderson, TN 38340

  This 76+/- acre hunting, recreational, and timber tract is located north of Palestine Lane in southwest Chester County, Tennessee. The property features a mix of ridgetops, sloping hills, and a small creek bottom, providing diverse terrain and excellent wildlife habitat. This tract offers a well-balanced timber profile, including approximately 10± acres of 25-year-old loblolly pine, 12± acres of

  Austin Carroll Tutt Land Company

  0 Palestine Ln, Henderson, TN 38340
• 

  

  /33

  $209,900

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft

  444 Galbraith Ave, Henderson, TN 38340

  This charming two-bedroom, two-bath home offers generous living space and thoughtful design, featuring a large office with built-in bookshelves, a sunroom, a formal living room with a beautiful fireplace, a dining room, and a cozy breakfast nook. The residence includes a spacious walkout basement and multiple sitting areas that invite you to enjoy the surrounding nature. A well-appointed backyard

  Zach Hannis Casey Realtors

  444 Galbraith Ave, Henderson, TN 38340
• 

  

  /31

  $310,000

  • 3 Beds
  • 2 Baths
  • 2,059 Sq Ft

  836 Hill Ave, Henderson, TN 38340

  FANTASTIC BRICK HOME IN AN EXCELLENT LOCATION JUST WAITING ON ITS NEW FAMILY, 3 BR., 2 BATHS, FORMAL DINING ROOM, LARGE GARAGE, LOTS OF BEAUTIFUL FLOWER BEDS, LARGE DECK AND GREAT BACK FENCED IN YARD

  Linda Carter Casey Realtors

  836 Hill Ave, Henderson, TN 38340
• 

  

  /23

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,360 Sq Ft

  200 Westwood Cove, Henderson, TN 38340

  Discover modern living at 200 Westwood Cove, a brand-new 3-bedroom, 2-bath home featuring a spacious open-concept living room, sleek kitchen with new appliances, a large backyard patio, and a 2-car garage. Located just 3 minutes from Henderson, TN, this move-in-ready home offers the perfect blend of convenience and comfort, all with no city taxes in a peaceful private cove.

  Brent West Crye-Leike Elite

  200 Westwood Cove, Henderson, TN 38340
• 

  /2

  $50,000

  • Land
  • 6.35 Acres
  • $7,874 per Acre

  0 Old Sobby Rd, Bethel Springs, TN 38315

  Beautiful wooded acreage, perfect for building your perfect country dreamhome! Land is directly across from 130 Old Sobby Road that is listed for sale. MLS #2502842

  

  Brandi Wilson

  RE/MAX Realty Source

  (731) 503-4833

  0 Old Sobby Rd, Bethel Springs, TN 38315
• 

  

  /44

  $469,500

  • Land
  • 180 Acres
  • $2,608 per Acre

  3385 Tennessee 125, Henderson, TN 38340

  180+/- acres | Hunting • Recreation • Timber | Silerton, TNThis 180+/- acre hunting and recreational tract is ideally located in Silerton, Tennessee, with extensive frontage along Highway 125, Hickory Grove Cemetery Lane, and Big Rock Trail. The property features a blend of rolling and sloping hills, and a minor creek bottom, creating both scenic views and diverse wildlife

  Austin Carroll Tutt Land Company

  3385 Tennessee 125, Henderson, TN 38340
• 

  

  /34

  $294,700

  • 3 Beds
  • 2 Baths
  • 1,465 Sq Ft

  4745 Enville Rd, Henderson, TN 38340

  Looking for a great house out in the country. This is it. 3 br., 2 baths, open floor plan, 2 car garage, lots of closet space, all kitchen appliances, covered front porch, large deck, LARGE LOT AND NEW CH/A PLUS DUCTWORK. AENEAS INTERNET, CALL FOR A WONDERFUL SHOWING

  Linda Carter Casey Realtors

  4745 Enville Rd, Henderson, TN 38340
• 

  

  /30

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,522 Sq Ft

  90 Timber Ridge Cove, Henderson, TN 38340

  FANTASTIC HOME LOCATED IN A SMALL SUBDIVISION, DEAD END OF THE CUL DE SAC, 3 BR., 2 BATHS, OPEN LIVING ROOM, KITCHEN AND DINING ROOM, LOTS OF CLOSET SPACE IN EACH BEDROOM, ALL KITCHEN APPLIANCES, GREAT PATIO OUT BACK WITH A PAVILLION COVER ON A PORTION OF IT. ABOVE GROUND POOL AREA, FENCED IN WITH A WROUGHT IRON FENCE AROUND POOL AND PATIO, THE REMAINING BACK YARD ALSO FENCED IN WITH A WOOD AND

  Linda Carter Casey Realtors

  90 Timber Ridge Cove, Henderson, TN 38340
• 

  

  /4

  $104,900

  • Land
  • 0 Acre

  xxx Center Point Rd S, Reagan, TN 38368

  Beautiful 9.1-acre tract in Chester County offering an ideal setting to build your dream home. Just off Highway 22 and convenient to Highway 100, this property provides easy access while maintaining a peaceful, private atmosphere. A long, private driveway leads to an elevated homesite perched on a hill, offering privacy and one of the most scenic locations in the county. If you've been searching

  Sheila Darnell EXIT Realty Blues City

  xxx Center Point Rd S, Reagan, TN 38368
• 

  

  /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
• 

  

  /23

  $269,900

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  533 North Ave, Henderson, TN 38340

  Discover this stunning, completely remodeled 4-bedroom, 2.5-bath home featuring a spacious 2-car garage. Every detail has been thoughtfully updated, including brand-new cabinets, flooring, and lighting fixtures, creating a fresh and modern living space. The HVAC system has been replaced for optimal comfort year-round. Enjoy the beautifully landscaped yard—perfect for outdoor gatherings,

  Zach Hannis Casey Realtors

  533 North Ave, 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

Showing Results 1 - 40, Page 1 of 3