Chester County TN Homes for Sale

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  /67

  $799,000

  • 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
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  /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
• 

  

  

  /11

  $85,000

  • 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
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  /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
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  /46

  $550,000

  • 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
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  /34

  $249,900

  • 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
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  /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
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  /27

  $275,000

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

  6525 State Route 225, Henderson, TN 38340

  Seller offering 3% closing cost assistance to the buyer! This 4 bedroom, 2 bath home offers plenty of space and great potential. Inside you'll find a comfortable layout with room to spread out and make it your own. Step outside and you'll find a double shed out back, perfect for storage, hobbies, or a workshop. The property also includes a storm shelter, adding an extra level of safety and peace

  

  Destiny Burns

  Stellar Realty Group

  (731) 868-7932

  6525 State Route 225, 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
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  /24

  $239,000

  • 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
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  /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

  (731) 206-2582

  2305 Enville Rd, Henderson, TN 38340
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  /14

  $85,000

  • Land
  • 6.6 Acres
  • $12,879 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
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  /59

  $1,300,000

  • 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
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  /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
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  /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
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  /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
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  /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
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  /38

  $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
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  /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
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  /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
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  /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
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  /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
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  /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

  (731) 361-7904

  707 Mifflin Avenue Extension, Henderson, TN 38340
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  /23

  $229,900

  • 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
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  /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
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  /6

  $20,000

  • Land
  • 0.42 Acre
  • $47,619 per Acre

  0 Carolina St Unit 10211177, Henderson, TN 38340

  +/- .42 ACRES IN THE HEART OF HENDERSON. GREAT BUILDING LOT. ROAD FRONTAGE ON SOUTH CAROLINA AVENUE. CLOSE TO DOWNTOWN. NEARBY PUBLIC SCHOOLS & FREED HARDEMAN UNIVERSITY. FLAT LAND. PAVED ROAD FRONTAGE. CITY RESTRICTIONS TO PROTECT YOUR INVESTMENT. CALL TODAY!

  Ashton Roberts Molly Moore Realty

  0 Carolina St Unit 10211177, Henderson, TN 38340
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  /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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  /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
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  /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
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  /6

  $20,000

  • Land
  • 1.3 Acres
  • $15,385 per Acre

  Lot 22 Timberwood Cove, Henderson, TN 38340

  Nice residential lot in great location! This 1.3 acre vacant lot in Creekside Estates is ready for your dream home!

  Tara Joyner BHGRE Conner Brownsville

  Lot 22 Timberwood Cove, Henderson, TN 38340
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  /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
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  /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
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  /15

  $225,550

  • Land
  • 45.11 Acres
  • $5,000 per Acre

  0 Highway 22 A, Enville, TN 38332

  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!

  Lori Yarbro Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
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  /25

  $524,900

  • 7 Beds
  • 4 Baths
  • 5,248 Sq Ft

  4335 Silerton Rd, Henderson, TN 38340

  Spacious 7-bedroom, 4-bath home on 44 acres featuring a full basement, bonus room, and a large workshop. The main level offers 3 bedrooms, a full kitchen, living areas, and easy access to the sunroom that overlooks the property. The basement adds 4 more bedrooms, a second full kitchen, and additional living space, plus a second wood-burning fireplace for cozy nights. A 2-car attached garage,

  Zach Hannis Casey Realtors

  4335 Silerton Rd, Henderson, TN 38340
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  /20

  $469,385

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

  0 Highway 100, 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.

  Compass Sales Compass South Land Sales

  0 Highway 100, Henderson, TN 38340
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  /41

  $299,999

  • 3 Beds
  • 2 Baths
  • 2,101 Sq Ft

  205 Pinecrest Dr, Henderson, TN 38340

  Welcome home to 205 Pinecrest Drive - a beautifully maintained brick home offering warmth, space, and timeless appeal in one of Henderson's most established neighborhoods. Built in 1978 and featuring over 2,100 square feet, this 3-bedroom, 2-bath home combines comfort and function with a layout designed for everyday living. You'll appreciate the inviting curb appeal, manicured landscaping, and

  

  Brandi Wilson

  RE/MAX Realty Source

  (731) 330-8286

  205 Pinecrest Dr, Henderson, TN 38340
• 

  

  /32

  $289,900

  • 4 Beds
  • 2.5 Baths
  • 3,780 Sq Ft

  524 Hill Ave, Henderson, TN 38340

  Spacious 3,780 sq. ft. home featuring 4 bedrooms and 2.5 baths with plenty of extra space throughout. The main level offers 3 bedrooms, 2 full baths, and a large bonus room on the back of the home—perfect for a family room or game area. Upstairs includes an additional bedroom, half bath, and a generous storage area. The fenced backyard includes a storm shelter and is ideal for pets or outdoor

  Lori Yarbro Evans Real Estate

  524 Hill Ave, Henderson, TN 38340
• 

  

  /14

  $850,000

  • Land
  • 149 Acres
  • $5,705 per Acre

  0 Highway 22 A, Henderson, TN 38340

  149-Acre Farm in Highly Sought-After Western Tennessee! Escape to the peaceful countryside with this beautiful 149-acre farm offering the best of Tennessee living. This versatile property features 60 acres of productive cotton fields, perfect for continued agricultural use or future expansion. For outdoor enthusiasts, a current hunting lease is already in place—providing prime access to an

  

  Destiny Burns

  Stellar Realty Group

  (731) 330-1977

  0 Highway 22 A, 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
• 

  

  /8

  $44,995

  • Land
  • 7.84 Acres
  • $5,739 per Acre

  0 Hughes Rd, Henderson, TN 38340

  Newly survyed 7.84 acre property close to Chickasaw State Park! This property features a cleared building site and frontage on two roads with Chickasaw State Park owning the land right across the road. Give me a call today for more information.

  Braden Rickman Farm & Home Realty

  0 Hughes Rd, Henderson, TN 38340

Showing Results 41 - 80, Page 2 of 3