Chester County TN Homes for Sale

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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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  /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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  /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

  $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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  /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
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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

  $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
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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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  /38

  $399,900

  • 3 Beds
  • 2 Baths
  • 2,350 Sq Ft

  580 Tennessee 125, Henderson, TN 38340

  Welcome to 580 State Route 125 in Henderson—where space, privacy, and timeless charm come together on 5.25 scenic acres! The southern boundary borders Chickasaw State Park, ensuring permanent privacy and protected natural surroundings. This 3-bedroom, 2-bath brick home offers true one-level living with a functional layout and generously sized rooms throughout. A welcoming covered 27x6 front porch

  

  Amy McLemore

  Total Realty Source

  (731) 747-3875

  580 Tennessee 125, Henderson, TN 38340
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  /34

  $319,900

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft

  766 Mason Ave, Henderson, TN 38340

  Move right in to this newly re modeled home with all new floors, new paint, new windows and deck!! Charming 3-Bedroom Brick Home on a Private Street Welcome to this inviting 3-bedroom, 2-bath brick home tucked away at the end of a quiet private street, offering comfort, privacy, and convenience. The open living area creates a warm and welcoming atmosphere, highlighted by a cozy gas

  

  Melanie Malone

  Crye-Leike Elite

  (731) 747-4578

  766 Mason 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

  (731) 260-8952

  00 Old State Highway 22a, Enville, TN 38332
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  /34

  $425,000

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

  450 North Ave, Henderson, TN 38340

  Spacious and full of character, this well-built 5 bedroom, 4 bath home offers 3,631 square feet of living space on a beautifully established property with mature trees and timeless charm throughout. Designed with flexibility and functionality in mind, this unique property features a finished basement with walk-out garage access, a circular driveway with automatic gates, and exceptional parking

  

  Melanie Malone

  Crye-Leike Elite

  (731) 318-1174

  450 North Ave, 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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  /73

  $499,000

  • 5 Beds
  • 3.5 Baths
  • 3,860 Sq Ft

  632 North Ave, Henderson, TN 38340

  Y'all... this one feels like HOME the second you pull in! Beautiful brick home right in the heart of Henderson just minutes from Freed-Hardeman, Main Street, and the 45 Bypass! Featuring 5 bedrooms, 3.5 baths, a recently remodeled kitchen and dreamy primary bath, plus a custom-built brick hearth that absolutely steals the show Perfect setup for a large or extended family with room for everybody

  

  Destiny Burns

  Stellar Realty Group

  (731) 203-9745

  632 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

  (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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  /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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  /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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  /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
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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

  Enville 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
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  /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
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  /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
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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
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  /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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  /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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  /39

  $525,000

  • 4 Beds
  • 2 Baths
  • 2,061 Sq Ft

  940 Old Lula Rd, Reagan, TN 38368

  #5549 - TENNESSEE COUNTRY ESTATE-CREEK-SPRINGS-FENCED PASTURES-BARN-OUTBUILDINGS-WOODED & OPEN LAND-HOBBY FARM-HUNTING: Nestled in the Heart of Rural Tennessee, this Attractive Farm with its 4BD/2BTH Brick Home sits Proudly on 61.5 Pristine Acres+/- of Gently Rolling, Usable Land that Perfectly Blends Fenced Pastures w/Mature Timber, Year-Round Creek, Springs, Trails, & Large Open Area along the

  Tony Alcott UC River City Realty

  940 Old Lula Rd, Reagan, TN 38368
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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

  $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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  /56

  $460,000

  • 4 Beds
  • 3 Baths
  • 1,916 Sq Ft

  130 Moss Loop, Enville, TN 38332

  Experience country charm on 20 serene acres just minutes from Henderson. This 2014-built 4-bedroom, 3-bath home features wide halls & doors, beautiful walk in closets and step in showers, ensuring comfort for all. Step into the expansive living room that flows right off into the gorgeous kitchen making it perfect for hosting family gatherings, cozy evenings or hosting in style. Relax on the

  Tiffany Elder Porchlight Realty West TN

  130 Moss Loop, Enville, TN 38332
• 

  

  /31

  $264,900

  • 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
• 

  

  /18

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  341 Melodie Cir, Henderson, TN 38340

  Welcome to 341 Melodie Circle in Henderson, Tennessee — where comfort, updates, and privacy come together. This well-maintained home features beautifully updated bathrooms, including a primary suite with a tiled walk-in shower complete with a rainfall showerhead for a spa-like experience. The secondary bathroom offers a stylish tub/shower combo with modern plumbing fixtures and updated flooring,

  Jake Morford Phillips Realty Group

  341 Melodie Cir, 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

Showing Results 1 - 40, Page 1 of 3