Chester County TN Homes for Sale

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  /82

  $159,899

  • Land
  • 22 Acres
  • $7,268 per Acre

  Cave Springs Rd, Henderson, TN 38340

  22 Acres Timberland with Survey, Soil Map, Electric, Perc Tested near Jackson TnCash Price: $159,899Owner Finance: $4,900 down, then $1,390.24/Month for 30 years (includes principal, interest and processing).Reservation Fee: $900 non-refundable reservation fee secures this property. Reservation fee will be counted toward purchase price or down payment.With your

  

  Elegment Land

  Elegment.com

  (970) 420-2440

  Cave Springs Rd, 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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  /16

  $209,900

  • 4 Beds
  • 2 Baths
  • 1,248 Sq Ft

  2305 Enville Rd, Henderson, TN 38340

  Enjoy peaceful country living just minutes from town in this beautifully updated 4-bedroom, 2-bath home situated on a picturesque 1-acre lot. Take in stunning views of rolling hills from your property, offering a true sense of space and serenity. The home features new hardwood floors, an updated kitchen with refreshed cabinetry, and a charming wood ceiling that adds warmth and character. The

  

  Melanie Malone

  Crye-Leike Elite

  (731) 206-2582

  2305 Enville Rd, Henderson, TN 38340
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  /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

  (731) 252-5648

  50 Braund Rd, Henderson, TN 38340
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  /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

  $299,999

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

  205 Pinecrest Dr, Henderson, TN 38340

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

  

  Brandi Wilson

  RE/MAX Realty Source

  (731) 330-8286

  205 Pinecrest Dr, Henderson, TN 38340
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  /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

  (970) 420-2440

  Enville Rd, Henderson, TN 38340
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  /80

  $926,900

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

  575 Homestead Ln, Henderson, TN 38340

  If you've been needing space for everybody without giving up comfort or privacy, this home is one you need to see. Sitting on approximately 3.11 acres at the end of a dead-end road, it offers 5 bedrooms, 4 full baths, and a half bath in the garage with a layout that just makes sense. The main floor includes the primary suite, 2 additional bedrooms, an office, and laundry room, while upstairs has

  

  Destiny Burns

  Stellar Realty Group

  (731) 330-1771

  575 Homestead Ln, Henderson, TN 38340
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  /34

  $249,900

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

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

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

  

  Jesse Bradley

  Tennessee Valley Realty and In

  (731) 207-4441

  2215 State Route 22a S, Jacks Creek, TN 38347
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  /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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  /41

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  980 Johnson Crossroads Rd, Jacks Creek, TN 38347

  Country living on approximately 4 acres, tucked among mature trees — a peaceful retreat with plenty of privacy. This well-kept 3-bedroom, 2-bath home features hardwood floors throughout, a generous kitchen/dining combo for family meals, a comfortable living room, and a dedicated office space. Step outside to a nice backyard patio ideal for relaxing or entertaining. Practical extras include a

  

  Logan Drewry

  Casey Drewry Realty

  (731) 577-3370

  980 Johnson Crossroads Rd, Jacks Creek, TN 38347
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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

  $42,000

  • 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

  $275,000

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

  6525 State Route 225, Henderson, TN 38340

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

  

  Destiny Burns

  Stellar Realty Group

  (731) 868-7932

  6525 State Route 225, Henderson, TN 38340
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  /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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  /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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  /25

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,354 Sq Ft

  707 Mifflin Avenue Extension, Henderson, TN 38340

  Welcome home to this beautifully maintained 3-bedroom, 2-bath residence located in the heart of the city. Designed with an open floor plan, this home offers seamless flow between the living, dining, and kitchen areas—perfect for everyday living and entertaining. There's plenty of space for a large dining table, complemented by a kitchen peninsula with seating for casual meals and gatherings.

  

  Melanie Malone

  Crye-Leike Elite

  (731) 361-7904

  707 Mifflin Avenue Extension, Henderson, TN 38340
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  /2

  $139,900

  • 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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  /22

  $209,900

  • 3 Beds
  • 1.5 Baths
  • 1,141 Sq Ft

  455 Hill Ave, Henderson, TN 38340

  Location, location, location! This adorable 3 bedroom, 1.5 bath home is just a 2-3 minute walk to Freed-Hardeman University, making it a prime spot for convenience and opportunity. Whether you're a first-time homebuyer, looking to downsize, or searching for a solid investment property, this one checks all the boxes. Step inside to a comfortable layout with just the right amount of space, easy to

  

  Destiny Burns

  Stellar Realty Group

  (731) 937-3197

  455 Hill Ave, Henderson, TN 38340
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  /21

  $253,900 New Construction

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

  757 Christi Loop, Henderson, TN 38340

  Two year builder warranty on house and appliances!! 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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  /44

  $469,500

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

  3385 Tennessee 125, Henderson, TN 38340

  180+/- acres | Hunting • Recreation • Timber | Silerton, TNThis 180+/- acre hunting and recreational tract is ideally located in Silerton, Tennessee, with extensive frontage along Highway 125, Hickory Grove Cemetery Lane, and Big Rock Trail. The property features a blend of rolling and sloping hills, and a minor creek bottom, creating both scenic views and diverse wildlife

  Austin Carroll Tutt Land Company

  3385 Tennessee 125, Henderson, TN 38340
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  /20

  $469,385

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

  0 Highway 100, Henderson, TN 38340

  Located north of Hwy 100, only 80 miles east of Memphis and 30 minutes south of Jackson, the Deberry Tract in Chester County, Tennessee, is an exceptional hunting and recreational property!The tract is fully wooded with approximately 1/3 of the acreage in mature merchantable loblolly pine. The remainder of the timber is white oak dominated hardwoods that were lightly thinned in 2015.

  Compass Sales Compass South Land Sales

  0 Highway 100, Henderson, TN 38340
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  /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
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  /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
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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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  /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
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  /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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  /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
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  /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
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  /34

  $345,000

  • 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
• 

  

  /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
• 

  

  /31

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft

  5195 Tennessee 200, Henderson, TN 38340

  Nestled on 5 peaceful acres in the county, this charming 3 bedroom, 2 bath home offers the perfect blend of comfort and privacy. Enjoy quiet mornings and peaceful evenings on the large front porch, surrounded by serene country views. Inside, you'll find an inviting open floor plan ideal for both everyday living and entertaining. The home has been thoughtfully updated with vinyl siding, gutters,

  Jennifer Stevens Stellar Realty Group

  5195 Tennessee 200, Henderson, TN 38340
• 

  

  /23

  $230,000

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  755 Holmes Dr, Henderson, TN 38340

  Nestled at the end of a quiet cul-de-sac and backing up to peaceful woods, this 3 bedroom, 2 bath home sits on almost half an acre and offers a sense of privacy and calm that just feels like home the moment you arrive. Step inside to a comfortable living space that flows easily into the kitchen and dining area, perfect for everyday living and gathering with the ones you love. The kitchen features

  Dessie Hardee RE/MAX Realty Source

  755 Holmes Dr, Henderson, TN 38340
• 

  

  /24

  $239,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  155 Whitley Ave, Henderson, TN 38340

  Welcome to this charming home built in 2023 that blends modern style with comfortable everyday living. This super cute 3-bedroom, 2-bath home features an open-concept floor plan designed for both entertaining and relaxing. The kitchen and living area flow seamlessly together, highlighted by white shaker cabinets, granite countertops throughout, and a roomy walk-in pantry that offers exceptional

  Amanda Driver Blackwell Realty and Auction

  155 Whitley Ave, Henderson, TN 38340
• 

  

  /38

  $310,000

  • 3 Beds
  • 2 Baths
  • 2,059 Sq Ft

  836 Hill Ave, Henderson, TN 38340

  FANTASTIC BRICK HOME IN AN EXCELLENT LOCATION JUST WAITING ON ITS NEW FAMILY, 3 BR., 2 BATHS, FORMAL DINING ROOM, LARGE GARAGE, LOTS OF BEAUTIFUL FLOWER BEDS, LARGE DECK AND GREAT BACK FENCED IN YARD

  Linda Carter Casey Realtors

  836 Hill Ave, Henderson, TN 38340
• 

  

  /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

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