Chester County TN Homes for Sale

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  /16

  $28,000

  • Land
  • 5.22 Acres
  • $5,364 per Acre

  TRACT 1 Highway 22 A, Jacks Creek, TN 38347

  NO CREDIT CHECKS - $1000 DOWN & ONLY $237/MTH 5.22 ACRES - LAND FOR SALE – JACKS CREEK, TN TRACT 1 HWY 22A JACKS CREEK, TN Looking for affordable land with natural beauty and water on-site? These tracts in Jacks Creek, TN offer a great mix of road frontage, wooded privacy, and several creeks running through most of the property. THIS PROPERTY IS IN THE FLOOD ZONE - SEE MAP IN PICS Price: $28,000

  Timothy Crane 2 Cranes Realty

  TRACT 1 Highway 22 A, Jacks Creek, TN 38347
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  /16

  $44,000

  • Land
  • 7.3 Acres
  • $6,027 per Acre

  TRACT 13 Highway 22 A, Jacks Creek, TN 38347

  NO CREDIT CHECKS - $1000 DOWN & ONLY $377/MTH 7.3 ACRES - LAND FOR SALE – JACKS CREEK, TN TRACT 13 HWY 22A JACKS CREEK, TN Looking for affordable land with natural beauty and wooded? These tracts in Jacks Creek, TN offer a great mix of road frontage and wooded privacy. Price: $44,000 -- Down Payment: $1,000 Financing: 10% APR (no bank needed) Monthly Payment Options: 30 Years: ~$377/mo + $10

  Timothy Crane 2 Cranes Realty

  TRACT 13 Highway 22 A, Jacks Creek, TN 38347
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  /3

  $110,000

  • Land
  • 12 Acres
  • $9,167 per Acre

  5030 Sand Mountain Rd, Enville, TN 38332

  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

  Brooke Murphy Real Broker

  5030 Sand Mountain Rd, Enville, TN 38332
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  /17

  $205,000

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

  5060 Enville Rd, Henderson, TN 38340

  Welcome to 5060 Enville Rd, a move-in ready country home on 2 acres of beautiful Tennessee land. This 3-bedroom, 2-bathroom home features a brand-new roof, well water, and a fully powered workshop, perfect for hobbies, projects, or small business use. Enjoy rural living with a chicken coop and plenty of space for outdoor activities, gardening, or entertaining. The country-style home offers

  Braden Mileham Blue Suede Realty

  5060 Enville Rd, Henderson, TN 38340
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  /33

  $244,700 New Construction

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  135 W Third St, Henderson, TN 38340

  This upscale, modern inspired REMODELED home seems brand new. It offers the perfect blend of upscale living. It boasts 1400 sq ft of living space on .92 acres right in the heart of Henderson. This beautifully crafted home features a spacious floor plan, high-end finishes, and functional, charming rooms. 3 bed, 2 bath w/ an open kitchen/living floor plan, & master suite with a walk-in closet.

  

  Ashton Roberts

  Molly Moore Realty

  (731) 324-5195

  135 W Third St, Henderson, TN 38340
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  /2

  $28,500

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

  234 N Franklin Ave, Henderson, TN 38340

  ARE YOU LOOKING FOR A COMPLETE FLIP PROJECT, THEN THIS COULD BE IT. GREAT LOT . SQ. FT IS APPROXIMATED

  Linda Carter Casey Realtors

  234 N Franklin Ave, Henderson, TN 38340
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  /91

  $869,900

  • 4 Beds
  • 3 Baths
  • 3,330 Sq Ft

  495 Knuckles Rd, Henderson, TN 38340

  TAKE A LOOK AT THIS BEAUTY, FANTASTIC CUSTOM BUILT BRICK HOME, SITING ON 21 ACRES +-, LONG DRIVEWAY TO THE HOUSE (SO IT IS SECLUDED), THIS HOME HAS SO MANY FEATURES, 4 BR. OR 3 BR AND BONUS ROOM, 3 BATHS, 2 ON MAIN LEVEL AND 1 ON UPPER FLOOR, MASTER BEDROOM HAS A NOOK THAT THEY HAVE TURNED INTO AN OFFICE, AND MASTER BATHROOM HAS A GREAT TUB PLUS A SEPARATE SHOWER, ALL ROOMS HAVE GREAT CLOSET

  Linda Carter Casey Realtors

  495 Knuckles Rd, Henderson, TN 38340
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  /2

  $99,900

  • 3 Beds
  • 1.5 Baths
  • 898 Sq Ft

  705 W Main St, Henderson, TN 38340

  Great location for a fixer upper! Turn this 3 bedroom 1 bath home into your dream home. House is on 1/2 acre on the main street in town. Convenient to Hwy 45 and State Route 100. Come see it today!

  

  Melanie Malone

  Crye-Leike Elite

  (731) 603-8625

  705 W Main St, Henderson, TN 38340
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  /7

  $79,900

  • Land
  • 26.8 Acres
  • $2,981 per Acre

  0 Sweet Lips Rd, Henderson, TN 38340

  Located in Henderson within Chester County, this approximately 26 to 27 acre parcel offers road access (no driveway currently installed) and was cleared and perc tested around 30 years ago, though updated testing would be recommended. Utilities are not currently installed, electric is likely available nearby, and the area typically utilizes well water and septic systems; the property appears to

  Daniel Demers Sell Your Home Services, LLC

  0 Sweet Lips Rd, Henderson, TN 38340
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  /2

  $64,900

  • Land
  • 8.9 Acres
  • $7,292 per Acre

  8705 Highway 100, Jacks Creek, TN 38347

  Discover 8.9 acres of opportunity in a peaceful rural setting in Jacks Creek, Tn. This versatile property offers plenty of space and potential for a variety of uses, whether you're looking to build your home, start a small business, or simply enjoy a quiet retreat. A private water well is already in place, providing a valuable resource for future development. With its convenient location and

  Richard Emison NextHome 383 Real Estate

  8705 Highway 100, Jacks Creek, TN 38347
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  /34

  $335,000

  • 3 Beds
  • 2.5 Baths
  • 2,156 Sq Ft

  185 Leath Ln, Finger, TN 38334

  Peace, privacy, and room to breathe. This beautiful brick home sits on 5 acres m/l just south of Henderson, conveniently located off Hwy 45. Built in 2006, this 3BR/2.5BA home offers approx. 2,156 sq ft with a flexible floor plan including an office, Jack-and-Jill bath, and laundry with half bath. Outdoor living features a covered and screened back porch, patio, storage building, storm shelter in

  Melanie Cromwell BST Realty

  185 Leath Ln, Finger, TN 38334
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  /32

  $319,000

  • 4 Beds
  • 2.5 Baths
  • 1,948 Sq Ft

  2925 State Route 100 W, Henderson, TN 38340

  Welcome to peaceful country living just minutes from town! This beautifully remodeled 4-bedroom, 2.5-bath home sits on 2.65 acres just outside the Henderson city limits and less than half a mile from West Chester Elementary. Completely renovated in 2022, the home was updated with improvements including updated wiring, plumbing, HVAC, roof, tilt windows and more. Inside, you'll find durable luxury

  Jennifer Scott RE/MAX Realty Source

  2925 State Route 100 W, Henderson, TN 38340
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  /9

  $19,900

  • Land
  • 1 Acre
  • $19,900 per Acre

  285 Cedar Brook Ln, Henderson, TN 38340

  Build the home you've been dreaming of in beautiful Hidden Hills Estates! This 1-acre building lot offers the perfect setting for a basement home, with a gentle slope that creates ideal elevation and design opportunities. Tucked at the back of the property, Tar Creek runs behind the lot, adding a peaceful natural backdrop and enhancing the privacy this homesite provides. Wildlife is

  

  Brandi Wilson

  RE/MAX Realty Source

  (731) 318-4546

  285 Cedar Brook Ln, Henderson, TN 38340
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  /74

  $734,900

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

  215 Benson Rd, Reagan, TN 38368

  HUGE PRICE DROP + MOTIVATED SELLERS! Now is your chance to own peaceful country 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

  Heather Pierce Coldwell Banker Southern Realty

  215 Benson Rd, Reagan, TN 38368
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  /33

  $226,250

  • 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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  /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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  /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

  $235,000

  • 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 Wendell Alexander Realty

  155 Whitley Ave, 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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  /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
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  /33

  $199,900

  • 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, "NEW ROOF INSTALLED APRIL,2026"

  Linda Carter Casey Realtors

  836 Hill Ave, Henderson, TN 38340
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  /23

  $255,000

  • 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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  /45

  $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

  $99,000

  • Land
  • 0 Sq Ft

  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

  $239,900

  • 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
• 

  

  /22

  $228,500

  • 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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  /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

  (731) 749-7993

  0 Hill Ave, Henderson, TN 38340
• 

  

  /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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  /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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  /13

  $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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  /33

  $315,000

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

  205 Pinecrest Dr, Henderson, TN 38340

  Welcome home to 205 Pinecrest Drive — a well-maintained 3-bed, 2-bath brick home in one of Henderson’s most established neighborhoods. With over 2,100 sq ft, this 1978 gem offers multiple living spaces, a cozy stone fireplace, formal dining and living rooms, and a bright kitchen with plenty of storage. Outside, enjoy a spacious yard plus an incredible 30x40 shop with a 14-ft roll-up door—perfect

  

  Brandi Wilson

  RE/MAX Realty Source

  (731) 330-8286

  205 Pinecrest Dr, Henderson, TN 38340
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  /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
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  /8

  $42,995

  • Land
  • 7.84 Acres
  • $5,484 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
• 

  

  /17

  $575,000

  • Land
  • 217.58 Acres
  • $2,643 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
• 

  

  /69

  $575,000

  • 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

Showing Results 41 - 80, Page 2 of 3