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Chester County TN Homes for Sale

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  • /74

    $734,900

    $165K PRICE DROP
    • 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
  • /33

    $226,250

    $3K PRICE DROP
    • 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
  • /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
  • /9

    $35,750

    $4K PRICE DROP
    • 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

    $235,000

    $20K PRICE DROP
    • 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
  • /59

    $1,300,000

    $50K PRICE DROP
    • 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

    $17K PRICE DROP
    • 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

    $389,900

    $10K PRICE DROP
    • 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
  • /36

    $431,900

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

    0 Hurst Rd, Henderson, TN 38340

    PT-03 is a 192+/- acre hunting, recreational, and timber tract located on Grooms Road and Hurst Road in Chester County, Tennessee. The topography consists of ridges with rolling and sloping hills, offering scenic views and excellent wildlife habitat. Approximately 85 acres consists aging upland pine and hardwoods, as well as an additional 95 acres of loblolly pine plantations planted in 2021,

    Austin Carroll Tutt Land Company

    0 Hurst 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
  • /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

    Scott Coggins The Agency Nashville, LLC

    150 Jacks Creek St, 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!

    Agent Photo

    Lori Yarbro

    Evans Real Estate

    0 Highway 22 A, Enville, TN 38332
  • /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

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    0 Highway 22 A, Henderson, TN 38340
  • /8

    $42,995

    $4K PRICE DROP
    • 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

    $565,000

    $35K PRICE DROP
    • Land
    • 217.58 Acres
    • $2,597 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

    $550,000

    $75K PRICE DROP
    • 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
  • /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
  • /13

    $152,075

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

    1700 Grooms Rd, Henderson, TN 38340

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

    Austin Carroll Tutt Land Company

    1700 Grooms Rd, Henderson, TN 38340
  • /9

    $269,000

    $16K PRICE DROP
    • Land
    • 0 Sq Ft

    X Cedar Brook Ln, Henderson, TN 38340

    Discover 63 acres of wooded landscape offering privacy and natural beauty just minutes from the conveniences of Henderson. The property features multiple potential building sites surrounded by mature trees and abundant wildlife. An entrance is located on Cedar Brook Lane, providing easy access while maintaining a peaceful country setting. Whether you're looking for a future home site,

    Sheila Darnell EXIT Realty Blues City

    X Cedar Brook Ln, Henderson, TN 38340
  • /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
  • /32

    $437,500

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

    3392 Sand Mountain Rd, Enville, TN 38332

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

    Austin Carroll Tutt Land Company

    3392 Sand Mountain Rd, Enville, TN 38332
  • /5

    $149,900

    $20K PRICE DROP
    • Land
    • 0 Sq Ft

    1170 Keene Rd, Enville, TN 38332

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

    Nathan Lilly Lilly Realty

    1170 Keene Rd, Enville, TN 38332
  • /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!

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    Lot 5 Greystone Cove, Henderson, TN 38340
  • /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!

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    Lot 22 Greystone Cove, Henderson, TN 38340
  • /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!

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    Lot 18 Greystone Cove, Henderson, TN 38340
  • /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!

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    Lot 21 Greystone Cove, Henderson, TN 38340
  • /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!

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    Lot 8 Greystone Cove, Henderson, TN 38340
  • /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!

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    Lot 7 Greystone Cove, Henderson, TN 38340
  • /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

    Agent Photo

    Lori Yarbro

    Evans Real Estate

    115 Chalet Ln, Henderson, TN 38340
  • /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

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    50 Braund Rd, Henderson, TN 38340
  • /24

    $750,000

    $49K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 4,280 Sq Ft

    715 Roundtree Ln, Beech Bluff, TN 38313

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

    Joyce Addison Coldwell Banker Southern Realty

    715 Roundtree Ln, Beech Bluff, TN 38313
  • /5

    $24,900

    $10K PRICE DROP
    • Land
    • 1.3 Acres
    • $19,154 per Acre

    Lot 21 Timberwood Cove, Henderson, TN 38340

    Exclusive 1.3-acre lot in a stunning subdivision with restricted covenants, offering a serene and mature environment. Enjoy the benefits of county taxes while building your dream home in this sought-after location. Don't miss this rare opportunity to own a piece of land in this prestigious community. Situated within a prestigious and coveted exclusive subdivision, this 1.3-acre property adheres

    Zach Hannis Casey Realtors

    Lot 21 Timberwood Cove, Henderson, TN 38340
  • /4

    $48,000

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

    00 Lofton Rd, Enville, TN 38332

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

    Larry Roberts Casey Realtors

    00 Lofton Rd, Enville, TN 38332
  • /17

    $159,900

    $5K PRICE DROP
    • Land
    • 75 Acres
    • $2,132 per Acre

    0 Grooms Rd, Henderson, TN 38340

    This 75+/- acre hunting and recreational tract is located north of Palestine Ln in southwest Chester County. It primarily consists of naturally regenerating hardwoods resulting from a silvicultural clearcut in 2023, as well as approximately 15 acres of loblolly pine planted in 2012. The western property line is a gated, shared-use road that is only used to access PT-07, PT-08, and PT-09. The

    Austin Carroll Tutt Land Company

    0 Grooms Rd, Henderson, TN 38340
  • /3

    $301,600

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

    00 Woodland Dr, Henderson, TN 38340

    "DEVELOPMENT ACREAGE: ONE OF THE LARGEST ZONED R3 CHUNKS OF LAND IN CITY LIMITS. Start a new subdivision and build houses, duplexes or apartments. R-3 has the smallest lot size requirement for any restricted zoning. Sewer main already runs through it, and all utilities are available on both roads-- Woodland Drive and Forrest Drive. Three 50' access points to build roads through the property.

    Linda Carter Casey Realtors

    00 Woodland Dr, 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
  • /8

    $55,000

    $10K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,864 Sq Ft

    2160 Jones Rd, Luray, TN 38352

    Renovations have been started on this large country home sitting on one acre. Staircase to unfinished attic area could also be finished. Needs complete remodel including floors. New well installed June 2022. TWO ADDITIONAL LOTS ARE AVAILABLE FOR PURCHASE BY BUYER, BUT ACREAGE CANT BE SOLD UNTIL HOUSE SITTING ON 1 ACRE CLOSED

    Linda Carter Casey Realtors

    2160 Jones Rd, Luray, TN 38352
  • /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
  • /5

    $20,000

    $7K PRICE DROP
    • Land
    • 1 Acre
    • $20,000 per Acre

    00 Deerfield Loop, Henderson, TN 38340

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

    Linda Carter Casey Realtors

    00 Deerfield Loop, Henderson, TN 38340

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