Chester County TN Homes for Sale

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  /66

  $549,000

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

  50 Braund Rd, Henderson, TN 38340

  

  Destiny Burns

  Stellar Realty Group

  (731) 252-5648

  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

  (731) 327-6186

  Lot 5 Greystone Cove, 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

  (731) 316-0342

  Lot 22 Greystone Cove, Henderson, TN 38340
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  /14

  $35,000

  • Land
  • 0.95 Acre
  • $36,842 per Acre

  2975 State Route 100 W, Henderson, TN 38340

  Beautiful lot available on the west side of town! This property is just under an acre and offers mature trees, city water, and endless possibilities. Whether you're looking to build your dream home or invest in land, this lot provides the perfect setting to create your forever home.

  

  Destiny Burns

  Stellar Realty Group

  (731) 540-8559

  2975 State Route 100 W, Henderson, TN 38340
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  /41

  $315,000

  • 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
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  /32

  $95,000

  • 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: $95,000Reservation 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

  (970) 420-2440

  Enville Rd, Henderson, TN 38340
• 

  

  /34

  $255,000

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

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

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

  

  Jesse Bradley

  Tennessee Valley Realty and In

  (731) 207-4441

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

  

  /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

  (731) 257-2344

  Lot 18 Greystone Cove, 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

  (731) 257-2136

  Lot 21 Greystone Cove, Henderson, TN 38340
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  /14

  $1,200,000

  • Land
  • 149 Acres
  • $8,054 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
• 

  

  /48

  $509,900

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

  515 Ridgewood Dr, Henderson, TN 38340

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

  

  Destiny Burns

  Stellar Realty Group

  (731) 200-6888

  515 Ridgewood Dr, Henderson, TN 38340
• 

  

  /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

  (731) 330-8452

  Lot 8 Greystone Cove, Henderson, TN 38340
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  /27

  $299,000

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

  6525 State Route 225, Henderson, TN 38340

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

  

  Destiny Burns

  Stellar Realty Group

  (731) 868-7932

  6525 State Route 225, Henderson, TN 38340
• 

  /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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  /22

  $110,000

  • Land
  • 8.77 Acres
  • $12,543 per Acre

  0 Peddy Vestal Loop, Henderson, TN 38340

  Land for Sale! Don't miss this opportunity to own approximately 8.77 acres in a prime location to build your dream home! With no restrictions, the possibilities are endless—design, build, or create exactly what you've imagined. Conveniently zoned for East Chester Schools in Chester County, this property won't last long. Act fast and make it yours today!

  

  Destiny Burns

  Stellar Realty Group

  (731) 251-4562

  0 Peddy Vestal Loop, Henderson, TN 38340
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  /64

  $619,000

  • 3 Beds
  • 3.5 Baths
  • 4,108 Sq Ft

  325 Ridgewood Dr, Henderson, TN 38340

  * HIGHLY MOTIVATED SELLERS * Welcome to 325 Ridgewood Dr. in Creekside Estates! This custom-built home offers over 4,100 heated square feet with three bedrooms and two full baths on the main floor, all centered around an open floor plan. The fully finished basement includes an oversized one-car garage, game room, family room, full bath, extra room that could be used as a bedroom, and an

  

  Destiny Burns

  Stellar Realty Group

  (731) 389-9336

  325 Ridgewood Dr, Henderson, TN 38340
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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

  (731) 666-6365

  Lot 7 Greystone Cove, Henderson, TN 38340
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  /26

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft

  316 Meadow Brook Dr, Henderson, TN 38340

  Welcome to this beautiful brick home located on the sought-after Meadowbrook Drive in Henderson, Tennessee! This charming residence features three spacious bedrooms and two full baths, all designed around an inviting open floor plan. Enjoy the outdoors with a brand new deck, perfect for entertaining or relaxing. Conveniently situated near Freed Hardeman University and downtown Henderson, this

  

  Destiny Burns

  Stellar Realty Group

  (731) 535-7172

  316 Meadow Brook Dr, Henderson, TN 38340
• 

  

  /31

  $499,900

  6145 Tennessee 225, Henderson, TN 38340

  You will never find a more beautiful piece of land in Chester County! This stunning +/- 79.97-acre property is a true gem, featuring a natural spring and a serene pond that enhance its picturesque landscape. Approximately 40 acres fenced and ready for a cattle farmer, this land offers the perfect setting for livestock.With timber that will be ready for cutting in just five years, there's

  

  Destiny Burns

  Stellar Realty Group

  (731) 224-4661

  6145 Tennessee 225, Henderson, TN 38340
• 

  

  /50

  $334,900 New Construction

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

  2885 Old Friendship Rd, Finger, TN 38334

  This very unique newly constructed home is situated on approximately 3.4 acres, offering privacy and a serene setting. The open-concept floor plan features beautiful coffered ceilings in the kitchen and a spacious primary suite with two oversized walk-in closets, a luxurious walk-in shower, and a relaxing soaking tub. Enjoy your morning coffee while taking in the peaceful views from the 30x14

  

  Destiny Burns

  Stellar Realty Group

  (731) 837-1337

  2885 Old Friendship Rd, Finger, TN 38334
• 

  

  /21

  $259,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,514 Sq Ft

  757 Christi Loop, Henderson, TN 38340

  $5000 Credit toward rate buy down or closing costs!! This charming new construction offers modern farmhouse appeal with clean lines and timeless details. The white board-and-batten style vinyl siding exterior is complemented by a welcoming front porch, complete with a ceiling fan for comfort, the covered back porch gives peaceful vibes for your morning coffee or tea. Inside, you'll find a

  

  Brandi Wilson

  RE/MAX Realty Source

  (731) 506-0286

  757 Christi Loop, Henderson, TN 38340
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  /33

  $464,000 New Construction

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  550 Trice Rd, Henderson, TN 38340

  Magnolia Springs Subdivision - New Construction by Anderson Blackwell Construction - Be the first to own a home in Magnolia Springs, one of Henderson's newest and most exciting subdivisions! This stunning white brick home with black accents combines modern elegance, functional design, and beautiful natural light throughout. Step inside to a spacious open-concept living area featuring soaring

  

  Brandi Wilson

  RE/MAX Realty Source

  (731) 982-2209

  550 Trice Rd, Henderson, TN 38340
• 

  

  /21

  $245,000

  • 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
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  /28

  $574,900

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

  10430 Tennessee 100, Henderson, TN 38340

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

  Joe Cummings

  10430 Tennessee 100, Henderson, TN 38340
• 

  

  /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
• 

  

  /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
• 

  

  /9

  $44,900

  • Land
  • 13.3 Acres
  • $3,376 per Acre

  285 Sherry Ln, Enville, TN 38332

  Discover your private sanctuary..13.3 Acres of Secluded Land. Are you looking for a hunting retreat or are you ready to escape the hustle and bustle of city life? Imagine owning 13.3 acres of pristine, secluded lane that offers you the perfect blend of tranquility and adventure. This is an opportunity to create your own private sanctuary far away from the noise an distractions of everyday life.

  Chris Carothers West Tennessee

  285 Sherry Ln, Enville, TN 38332
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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
• 

  

  /50

  $4,500,000

  • 5 Beds
  • 8 Baths

  140 Lake Shore Ln, Henderson, TN 38340

  Nestled on 52 pristine acres, this sprawling 8,264 square-foot estate offers unparalleled luxury and privacy. A true masterpiece of design and craftsmanship, the home features an open, expansive layout, high-end finishes, and sweeping views of the surrounding natural beauty. Step outside and discover your own personal paradise. A beautifully designed pool and hot tub overlook the tranquil,

  Brandon Pendergrass Hayden Outdoors Real Estate

  140 Lake Shore Ln, Henderson, TN 38340
• 

  

  /35

  $123,930

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

  0 Grooms Rd, Henderson, TN 38340

  PT-01 is located in southwest Chester Co. on Grooms Rd. This recreational and hunting tract contains 55.08 acres, of which approximately 15 acres being mature loblolly pine with the remaining acreage being a stand of two year old loblolly pine. This habitat diversity makes for great deer and turkey hunting opportunities.The topography is considered rolling and sloping hills. It has

  Austin Carroll Tutt Land Company

  0 Grooms Rd, 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
• 

  

  /30

  $171,900

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

  0 Grooms Rd, Henderson, TN 38340

  This 76+/- acre hunting/recreational tract and timber investment is located north of Palestine Ln in southwest Chester County. It consists of ridges with sloping hills, as well as a minor creek bottom.The property contains 10+/- acres of 25 year old loblolly pine, 12+/- acres of 13 year old loblolly pine, 20+/- acres of 5 year old loblolly pine, and 32+/- acres of aging upland and

  Austin Carroll Tutt Land Company

  0 Grooms Rd, Henderson, TN 38340
• 

  

  /65

  $799,000

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

  6275 Main St, Enville, TN 38332

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

  Nathan McCollum Mossy Oak Properties Southeast Land & Wildlife, LLC

  6275 Main St, Enville, TN 38332
• 

  

  /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
• 

  

  /17

  $159,900

  • 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
• 

  

  /31

  $892,250

  • Land
  • 415 Acres
  • $2,150 per Acre

  0 Tucker Rd, Bethel Springs, TN 38315

  LH-09 is located in southwest Chester Co. on Tucker Rd; southwest of Henderson and northwest of Selmer. This 415+/- acre hunting and recreational property contains a diverse mixture of timber stands and habitats that is sure to provide fantastic opportunities for deer and turkey hunting. It has several different forest types and ages including upland hardwoods, upland loblolly plantations,

  Austin Carroll Tutt Land Company

  0 Tucker Rd, Bethel Springs, TN 38315
• 

  

  /27

  $359,900

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

  2985 Sand Mountain Rd, Enville, TN 38332

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

  Jodie Parrish RE/MAX Realty Source

  2985 Sand Mountain Rd, Enville, TN 38332
• 

  

  /34

  $294,700

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

  4745 Enville Rd, Henderson, TN 38340

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

  Linda Carter Casey Realtors

  4745 Enville Rd, Henderson, TN 38340

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