Chester County TN Homes for Sale

• 

  

  

  /8

  $42,000

  • Land
  • 2.12 Acres
  • $19,811 per Acre

  Lot 8 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 8! This beautiful 3.12-acre lot is nestled in one of Chester County's most desirable subdivisions. If you're looking for the perfect spot to build your forever home, this is it!

  

  Destiny Burns

  Stellar Realty Group

  Lot 8 Greystone Cove, Henderson, TN 38340
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  /39

  $210,000

  $89K PRICE DROP

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

  6525 State Route 225, Henderson, TN 38340

  Extremely motivated sellers, selling as is! 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 of mind.

  

  Destiny Burns

  Stellar Realty Group

  6525 State Route 225, 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

  0 Old Sobby Rd, Bethel Springs, TN 38315
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  /38

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,642 Sq Ft

  3290 Silerton Rd, Henderson, TN 38340

  All information deemed accurate but not warranted by seller, agent or company.

  

  Ben Roberts

  RE/MAX Realty Source

  3290 Silerton Rd, 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

  285 Cedar Brook Ln, Henderson, TN 38340
• 

  

  /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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  /35

  $480,000

  • Land
  • 143.34 Acres
  • $3,349 per Acre

  0 Highway 22 A, Enville, TN 38332

  Don’t miss this rare opportunity to own 143.34 unrestricted acres in a fantastic location just off Hwy 22 in Enville, Tennessee. This versatile tract offers convenient access to Lexington, Henderson, and Adamsville while still providing the privacy, nature, and wide-open space buyers are looking for. With electricity available at the road and multiple ideal building sites, this property is

  

  Lori Yarbro

  Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
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  /23

  $150,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  304 Mifflin Ave, Henderson, TN 38340

  Discover the perfect blend of convenience and affordability in this move-in-ready home just steps from Freed-Hardeman University and minutes from downtown Henderson. This inviting 2-bedroom, single-story home is ideal for anyone seeking an easy, low-maintenance lifestyle. Offering just under 1,000 square feet, the home features comfortable living areas and an eat-in kitchen with abundant cabinet

  

  Brandi Wilson

  RE/MAX Realty Source

  304 Mifflin Ave, Henderson, TN 38340
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  /9

  $55,000

  • Land
  • 5.5 Acres
  • $10,000 per Acre

  00 Old State Highway 22a, Enville, TN 38332

  5.5 Acres of Wooded Land with Dual Road Frontage - Ready to Build in Enville, TN (Chester County) Discover your perfect country getaway or future homesite on this beautiful 5.5-acre wooded property in Enville, Tennessee. Conveniently located with road frontage on both Moss Loop and Highway 22A, this parcel offers easy access and multiple options for driveway placement or building layout. A gravel

  

  Melanie Malone

  Crye-Leike Elite

  00 Old State Highway 22a, Enville, TN 38332
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  /4

  $42,000

  • Land
  • 1.65 Acres
  • $25,455 per Acre

  Lot 7 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 7! This beautiful 1.65-acre lot is nestled in one of Chester County's most desirable subdivisions. If you're looking for the perfect spot to build your forever home, this is it!

  

  Destiny Burns

  Stellar Realty Group

  Lot 7 Greystone Cove, Henderson, TN 38340
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  /60

  $388,900

  • 5 Beds
  • 4 Baths
  • 3,631 Sq Ft

  450 North Ave, Henderson, TN 38340

  Step into timeless charm with this beautifully constructed home filled with original woodwork, hardwood floors, and character you simply can't recreate. With 5 bedrooms and 4 baths, there's plenty of room for everyone to spread out and feel at home. Need extra income or space for extended family? The upstairs apartment offers its own private entrance along with a kitchen, living room, bedroom,

  

  Destiny Burns

  Stellar Realty Group

  450 North Ave, Henderson, TN 38340
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  /66

  $549,000

  • 4 Beds
  • 5 Baths
  • 3,376 Sq Ft

  50 Braund Rd, Henderson, TN 38340

  Just had a brand new roof put on! Let me tell you about this one like I would if we were standing in the kitchen together. This isn't just a four bedroom, five bath home with a basement — it's space to actually live. Room for everyone, whether that's kids, guests, or hosting the holidays without feeling stacked on top of each other. The basement gives you even more flexibility for a second living

  

  Destiny Burns

  Stellar Realty Group

  50 Braund Rd, Henderson, TN 38340
• 

  

  /7

  $42,000

  • Land
  • 1.61 Acres
  • $26,087 per Acre

  Lot 5 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 5! This beautiful 1.65-acre lot is nestled in one of Chester County's most desirable subdivisions. If you're looking for the perfect spot to build your forever home, this is it!

  

  Destiny Burns

  Stellar Realty Group

  Lot 5 Greystone Cove, Henderson, TN 38340
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  /49

  $749,900

  $10K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,845 Sq Ft

  25 Oak Ridge Dr, Henderson, TN 38340

  Welcome to Oakmont Estates! This spacious 5 bedroom, 3.5 bath home offers approximately 4,845 square feet of living space and sits on 2.05 acres in the heart of Chester County, where you can enjoy peaceful living with no city taxes. Inside, you'll find a functional layout featuring granite countertops in the kitchen, a dedicated office, and two large bonus rooms that provide flexibility for a

  

  Darrick Mann

  Crye-Leike Elite

  25 Oak Ridge Dr, Henderson, TN 38340
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  /72

  $834,900

  • 6 Beds
  • 5 Baths
  • 4,772 Sq Ft

  746 Oneal Ln, Henderson, TN 38340

  Okay, friend... this one is special. With 6 bedrooms, 3 full baths, and 2 half baths, there's room here for just about everyone. The main floor offers an open-concept layout with 4 bedrooms and 2.5 baths, making everyday living easy and comfortable. But wait until you see what's upstairs. The sellers recently finished and expanded the space beyond the rec room, adding 2 additional bedrooms, a

  

  Destiny Burns

  Stellar Realty Group

  746 Oneal Ln, Henderson, TN 38340
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  /7

  $42,000

  • Land
  • 2.94 Acres
  • $14,286 per Acre

  Lot 22 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 22! This beautiful 2.94-acre lot is nestled in one of Chester County's most desirable subdivisions. If you're looking for the perfect spot to build your forever home, this is it!

  

  Destiny Burns

  Stellar Realty Group

  Lot 22 Greystone Cove, Henderson, TN 38340
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  /89

  $896,000

  $31K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 6,888 Sq Ft

  575 Homestead Ln, Henderson, TN 38340

  MOTIVATED SELLERS! If you've been looking for a home with room for everyone and then some, this one is worth a look. Tucked away on approximately 3.11 acres at the end of a dead-end road, this 5-bedroom, 4 full bath home offers the space, privacy, and flexibility that's hard to find. The main floor features the primary suite, two additional bedrooms, an office, and laundry room. Upstairs, you'll

  

  Destiny Burns

  Stellar Realty Group

  575 Homestead Ln, Henderson, TN 38340
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  /17

  $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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  /46

  $349,900

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

  1380 Harrison Rd, Pinson, TN 38366

  Welcome to 1380 Harrison Ln, Pinson, TN — a rare opportunity to own a private retreat in one of West Tennessee's most exclusive gated communities. Located in Deanburg Hills HOA, this unique property offers more than just a home — it offers access to an incredible lifestyle with 480 private acres, a 20-acre lake, and recreation opportunities that are nearly impossible to find. With only 16 parcels

  

  Dylan Jones

  Southern LifeStyle Properties

  1380 Harrison Rd, Pinson, TN 38366
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  /34

  $234,900

  $20K PRICE DROP

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

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

  Country living at its best! Back on the market at no fault to the seller. 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

  

  Jesse Bradley

  Tennessee Valley Realty and In

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

  

  /5

  $42,000

  • Land
  • 2.27 Acres
  • $18,502 per Acre

  Lot 18 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 18! This beautiful 2.27-acre lot is nestled in one of Chester County's most desirable subdivisions. If you're looking for the perfect spot to build your forever home, this is it!

  

  Destiny Burns

  Stellar Realty Group

  Lot 18 Greystone Cove, Henderson, TN 38340
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  /65

  $825,000

  $25K PRICE DROP

  • 5,952 Sq Ft

  115 Chalet Ln, Henderson, TN 38340

  Secluded retreat featuring 7 charming cabins on 12.81 acres in a gated community with a private drive leading to all cabins. Currently operated as a 55+ community, 5 of the cabins are rented, offering excellent income potential. The main cabin is a spacious 2-bedroom, 3-bath home with 1,600 sq. ft. and is occupied by the owner. Five cabins are 2-bedroom, 1-bath units with 768 sq. ft. each, and

  

  Lori Yarbro

  Evans Real Estate

  115 Chalet Ln, Henderson, TN 38340
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  /8

  $42,000

  • Land
  • 3.77 Acres
  • $11,141 per Acre

  Lot 21 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 21! This beautiful 3.77-acre lot is nestled in one of Chester County's most desirable subdivisions. If you're looking for the perfect spot to build your forever home, this is it!

  

  Destiny Burns

  Stellar Realty Group

  Lot 21 Greystone Cove, Henderson, TN 38340
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  /14

  $850,000

  $350K PRICE DROP

  • 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

  0 Highway 22 A, Henderson, TN 38340
• 

  /2

  $37,500

  • Land
  • 0 Sq Ft

  00 Barham Ave, Henderson, TN 38340

  Great lot to build your dream home in Chester County. Great schools and family friendly community. Call Melanie at 731.879.9655

  

  Melanie Malone

  Crye-Leike Elite

  00 Barham Ave, Henderson, TN 38340
• 

  /2

  $234,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,258 Sq Ft

  610 Mifflin Ave, Henderson, TN 38340

  Welcome to your brand-new home in the highly anticipated Henderson Station subdivision! This stunning 3-bedroom, 2.5 bathroom property perfectly blends modern design with everyday functionality, starting with a welcoming front porch that offers excellent curb appeal for your morning coffee. Step inside to discover a bright, open-concept living area that flows seamlessly into a chef-inspired

  

  Melanie Malone

  Crye-Leike Elite

  610 Mifflin Ave, 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

  135 W Third St, Henderson, TN 38340
• 

  

  /16

  $93,100

  • Land
  • 38 Acres
  • $2,450 per Acre

  2404 Grooms Rd, Henderson, TN 38340

  This 38+/- acre tract in southwest Chester County offers a diverse mixture of hunting, recreation, and potential homesites. With approximately 900 feet of frontage on Grooms Road and a private shared-use easement road forming the western boundary, the property has practical access and multiple ways to approach future layout, hunting access, or site planning.The land is made up of

  Austin Carroll Tutt Land Company

  2404 Grooms Rd, Henderson, TN 38340
• 

  

  /45

  $469,500

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

  3385 Tennessee 125, Henderson, TN 38340

  180+/- acres | Hunting • Recreation • Timber | Silerton, TNThe Big Rock Tract is a 180± acre hunting, timber, and potential homesite property in Silerton, Tennessee, positioned along the edge of Chickasaw State Forest with frontage on Hwy 125, Hickory Grove Cemetery Lane, and Big Rock Trail. This tract combines the privacy and habitat of a large recreational property with the practical

  Austin Carroll Tutt Land Company

  3385 Tennessee 125, Henderson, TN 38340
• 

  

  /16

  $148,500

  • Land
  • 66 Acres
  • $2,250 per Acre

  0 Grooms Rd Unit 27226129, Henderson, TN 38340

  This 66-acre tract offers a balanced mix of timber, wildlife habitat, and usable ground in southwest Chester County, Tennessee. The property has frontage on Grooms Road and is accessed by a private shared-use easement road, providing easy accesswhile maintaining privacy off the main road.The timber makeup includes approximately 18 acres of 27-year-old loblolly pine, 19 acres of

  Austin Carroll Tutt Land Company

  0 Grooms Rd Unit 27226129, Henderson, TN 38340
• 

  

  /32

  $94,999

  • Land
  • 10.3 Acres
  • $9,223 per Acre

  Enville Rd, Henderson, TN 38340

  10.30 Acres Unrestricted Private Land 15 Min. Outside of Henderson TNCash Price: $94,999Reservation Fee: $900 non-refundable reservation fee secures this property. Reservation fee will be counted toward purchase price or down payment.With your Purchase You Get:1. Clean Title with a Deed in Your Name2. Build on your Land During the Financing Period3. Live on

  Elegment Land Elegment.com

  Enville Rd, Henderson, TN 38340
• 

  

  /47

  $2,999,900

  • 4 Beds
  • 5 Baths
  • 4,570 Sq Ft

  60 Proctor Rd, Henderson, TN 38340

  2602272 RF Located in Henderson, Tennessee, this exceptional luxury estate offers upscale living, premium construction, and fully equipped equestrian property across approximately 138 private acres surrounded by wildlife, trails, and natural beauty. With quick access to Jackson, Memphis, Nashville, US Highway 45, and Interstate 40, this property delivers both privacy and convenience. A circular

  Chris Carothers West Tennessee

  60 Proctor Rd, Henderson, TN 38340
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  /32

  $437,500

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

  3390 Sand Mountain Rd, Enville, TN 38332

  175+/- acres on Sand Mountain in Chester County, Tennessee. This hunting/recreational tract and timber investment has more than 500 feet of frontage along Sand Mountain Road and is situated along the Tennessee Valley Divide.The property sits atop Sand Mountain, which is the highest point in all of West Tennessee. The property contains approximately 155 acres of 7-year-old loblolly pine

  Austin Carroll Tutt Land Company

  3390 Sand Mountain Rd, Enville, TN 38332
• 

  

  /18

  $131,100

  • Land
  • 57 Acres
  • $2,300 per Acre

  0 Grooms Rd Unit 27226896, Henderson, TN 38340

  This 57+/- acre hunting and recreational tract in southwest Chester County offers the kind of layout serious land buyers look for: road frontage, terrain, habitat diversity, and multiple potential building sites.The property includes approximately 950 feet of frontage on Grooms Road, while the eastern boundary is defined by a private shared-use easement road. That combination gives the

  Austin Carroll Tutt Land Company

  0 Grooms Rd Unit 27226896, Henderson, TN 38340
• 

  

  /31

  $424,000

  • Land
  • 105 Acres
  • $4,038 per Acre

  935 Big Rock Trail, Henderson, TN 38340

  105 AC. BIG ROCK TRAIL, HENDERSON TN. OFF THE GRID LIVING Want to truly get away from it all? Look no further—this is as private and secluded as it gets. Tucked away at the end of a 1.5-mile winding driveway with no thru traffic, this incredible 105-acre retreat borders Chickasaw State Park—offering unmatched peace, privacy, and natural beauty. NO neighbors just you and nature. PROPERTY

  Jeremy Ryan Crye-Leike, Inc., REALTORS

  935 Big Rock Trail, Henderson, TN 38340
• 

  

  /22

  $125,000

  • Land
  • 18.84 Acres
  • $6,635 per Acre

  1555 U S 45, Henderson, TN 38340

  18.84-acre Development Opportunity | US Hwy 45 | Henderson, TNPositioned along the highly traveled corridor of US Highway 45 in Henderson, this 18.84 acre tract presents a compelling opportunity for investors, developers, and end-users seeking visibility and long-term growth potential in a great location.Currently zoned agricultural, the property offers rezoning potential to

  Austin Carroll Tutt Land Company

  1555 U S 45, Henderson, TN 38340
• 

  

  /13

  $152,075

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

  0 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

  0 Grooms Rd, Henderson, TN 38340
• 

  

  /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
• 

  

  /32

  $431,900

  • Land
  • 192 Acres
  • $2,249 per Acre

  0 Grooms Rd, Henderson, TN 38340

  PT-03 is located on Grooms Rd and Hurst Rd in Chester County. This hunting/recreational and timber tract contains approximately 192 acres of ridgetops with rolling and sloping hills. It contains roughly 85 acres in mature upland hardwoods and pine, as well as another 95 acres in loblolly pine plantations planted in 2021. There is a good ridge system that could be used for additional roads/trails,

  Austin Carroll Tutt Land Company

  0 Grooms Rd, Henderson, TN 38340
• 

  /2

  $749,000

  • Land
  • 210 Acres
  • $3,567 per Acre

  0 Highway 100 Unit 23269256, Reagan, TN 38368

  Check out this remarkable 210+/- acre tract in Hardeman County that directly adjoins Chickasaw State Forest. Ideally situated just 4 miles from Madison County and approximately 35 miles from Memphis, Tennessee, this property offers a rare combination of recreational appeal with short and long-term investment potential.The land features a robust stand of mature timberapproximately 200

  Taylor Howell Premier Farm Realty Group & Auction

  0 Highway 100 Unit 23269256, Reagan, TN 38368

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