Chester County, TN Homes

• 

  

  

  /22

  $136,300 Pending

  • Land
  • 58 Acres
  • $2,350 per Acre

  0 Grooms Rd, Henderson, TN 38340

  58+/- Acres of Hunting & Timberland - Grooms Rd, Chester County, TNQuick Facts:• Acreage: 58+/- acres• Location: Grooms Road, Chester County, Tennessee• Nearby Towns: Within 15 miles of Henderson, Selmer & Bolivar; 20 miles from Jackson• Land Use: Hunting, recreation, and timber investment• Timber Mix: 16± acres of 13-year-old loblolly pine, 10± acres of 4–5-year-old

  Austin Carroll Tutt Land Company

  0 Grooms Rd, Henderson, TN 38340
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  /18

  $80,000 Sold Jun 06, 2025

  7765 Broad St, Milledgeville, TN 38359

  • 3 Beds
  • 2 Baths
  • 1,791 Sq Ft
  • Built 1978

  Last Sold Summary

  • 42% Below List Price
  • $45/SF

  Current Estimated Value $130,430

  7765 Broad St, Milledgeville, TN 38359
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  /27

  Est $196,558 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,026 Sq Ft

  228 Tulip St, Henderson, TN 38340

  228 Tulip St, Henderson, TN 38340
• 

  

  

  /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
• 

  

  

  /19

  $189,900 Sold May 29, 2025

  639 Mifflin Ave, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,112 Sq Ft
  • Built 1969

  Last Sold Summary

  • $171/SF
  • 2 Days On Market

  Current Estimated Value $189,388

  Last Listing Agent Linda Carter Casey Realtors

  639 Mifflin Ave, Henderson, TN 38340
• 

  

  /30

  Est $197,382 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft

  354 Kitchen Dr, Henderson, TN 38340

  354 Kitchen Dr, 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
• 

  

  /23

  $36,900 Sold Jan 09, 2026

  2035 Brown Cemetery Rd, Luray, TN 38352

  • Land
  • 5.5 Acres
  • $6,709 per Acre

  Last Sold Summary

  • 48% Above List Price
  • 62 Days On Market

  Last Listing Agent Todd Clouser RE/MAX Realty Source

  2035 Brown Cemetery Rd, Luray, TN 38352
• 

  

  /23

  Est $172,000 Not Listed For Sale

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

  930 Clover Creek Rd, Medon, TN 38356

  930 Clover Creek Rd, Medon, TN 38356
• 

  

  /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
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  /48

  $580,000 Sold Apr 04, 2025

  315 Greystone Cove, Henderson, TN 38340

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Below List Price
  • $166/SF
  • 128 Days On Market

  Last Listing Agent Destiny Burns Stellar Realty Group

  315 Greystone Cove, Henderson, TN 38340
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  /24

  Est $137,626 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 832 Sq Ft

  438 Galbraith Ave, Henderson, TN 38340

  438 Galbraith Ave, Henderson, TN 38340
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  /26

  $289,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  290 Potleg Trail, Henderson, TN 38340

  Loretta Martin Chamberwood Realty Group

  290 Potleg Trail, Henderson, TN 38340
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  /54

  $310,000 Sold Sep 08, 2025

  25 Roundtree Ln, Beech Bluff, TN 38313

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $169/SF
  • 59 Days On Market

  Last Listing Agent Linda Carter Casey Realtors

  25 Roundtree Ln, Beech Bluff, TN 38313
• 

  

  /18

  Est $247,230 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 1,944 Sq Ft

  840 Woodland Dr, Henderson, TN 38340

  840 Woodland Dr, Henderson, TN 38340
• 

  

  /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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  /26

  $191,559 Sold Feb 10, 2025

  6100 Enville Rd, Henderson, TN 38340

  • 4 Beds
  • 2 Baths
  • 2,139 Sq Ft
  • Built 1990

  Last Sold Summary

  • 25% Below List Price
  • $90/SF
  • 319 Days On Market

  Current Estimated Value $210,000

  Last Listing Agent Jennifer Scott RE/MAX Realty Source

  6100 Enville Rd, Henderson, TN 38340
• 

  

  /19

  Est $197,017 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  380 Kitchen Dr, Henderson, TN 38340

  380 Kitchen Dr, Henderson, TN 38340
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  /33

  $525,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,600+ Sq Ft

  320 Rabbit Ranch Rd, Henderson, TN 38340

  Welcome to your private retreat—this charming 4-bedroom, 2-bath brick home is nestled on a sprawling 57-acre estate offering a rare combination of space, seclusion, and opportunity. Whether you’re looking for a forever home, hobby farm, or hunter’s paradise, this property delivers. Step inside to find a warm and inviting interior with spacious living areas, a functional kitchen, and a cozy

  Erica Maxwell Tiffany Jones Realty Group

  320 Rabbit Ranch Rd, Henderson, TN 38340
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  /24

  $130,000 Sold Dec 18, 2025

  3420 Old Friendship Rd, Finger, TN 38334

  • 3 Beds
  • 1.5 Baths
  • 1,120 Sq Ft
  • Built 1984

  Last Sold Summary

  • 27% Below List Price
  • $116/SF
  • 21 Days On Market

  Last Listing Agent Molly Moore Molly Moore Realty

  3420 Old Friendship Rd, Finger, TN 38334
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  /24

  Est $946,644 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  1760 State Route 225, Henderson, TN 38340

  1760 State Route 225, Henderson, TN 38340
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  /52

  $325,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  1310 Inca Rd, Henderson, TN 38340

  Beautifully maintained country retreat on 7.5 acres!This meticulously maintained home is as nice as the day it was built and offers the perfect blend of peaceful country living with convenient access to town. Situated on 7.5 of UNRESTRICTED land, much of it is already cleared and ready for future building. Recent survey on hand.Inside, you’ll find new windows with screens throughout, new

  Jessica Asberry EXIT Realty Blues City

  1310 Inca Rd, Henderson, TN 38340
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  /34

  $260,000 Sold Aug 25, 2025

  285 Mitchell Ln, Henderson, TN 38340

  • 2 Beds
  • 2 Baths
  • 3,240 Sq Ft
  • Built 2007

  Last Sold Summary

  • 10% Below List Price
  • $80/SF
  • 73 Days On Market

  Current Estimated Value $270,406

  Last Listing Agent Larry Roberts Casey Realtors

  285 Mitchell Ln, Henderson, TN 38340
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  /14

  Est $64,920 Not Listed For Sale

  • Studio
  • 1 Bath
  • 384 Sq Ft

  20 Campground Ln, Enville, TN 38332

  20 Campground Ln, Enville, TN 38332
• 

  

  /31

  $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
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  /13

  $190,000 Sold Jan 09, 2026

  2555 Old Finger Rd, Finger, TN 38334

  • 4 Beds
  • 1.5 Baths
  • 1,232 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Above List Price
  • $154/SF
  • 17 Days On Market

  Last Listing Agent Erik Pieniazek Steadfast Home Advisors

  2555 Old Finger Rd, Finger, TN 38334
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  /21

  Est $247,907 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  230 Sugar Creek Dr, Henderson, TN 38340

  230 Sugar Creek Dr, Henderson, TN 38340
• 

  

  /27

  $299,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  2305 Mockingbird Rd, Medon, TN 38356

  Peaceful country setting with so much to offer. Enjoy nature and entertaining while sitting on the front porch, on the amazing covered patio or in the 30x40 shop. The workshop currently is a hunter's dream! Inside the house you have 3 beds, 2 baths that have been freshly painted. Beautiful hardwood throughout. The open living and dining area provide yet another area to entertain. You'll

  Brandi Ragan Ragan Realty Group

  2305 Mockingbird Rd, Medon, TN 38356
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  /39

  $300,000 Sold Jul 22, 2025

  85 Neshova Ln, Henderson, TN 38340

  • 4 Beds
  • 2 Baths
  • 2,000+ Sq Ft
  • Built 2013

  Last Sold Summary

  • 2% Below List Price
  • $150/SF
  • 36 Days On Market

  Current Estimated Value $301,038

  Last Listing Agent Jennifer Greer Greer Real Estate Group

  85 Neshova Ln, Henderson, TN 38340
• 

  

  /27

  Est $262,702 Not Listed For Sale

  • Studio
  • 572 Sq Ft

  445 Smith Ln Unit 590, Henderson, TN 38340

  445 Smith Ln Unit 590, Henderson, TN 38340
• 

  

  /22

  $284,500 Pending

  • 3 Beds
  • 3 Baths
  • 2,440 Sq Ft

  225 E Third St, Henderson, TN 38340

  BEAUTIFUL BRICK HOME WITHIN 2 BLOCKS FROM FHU, WITH SO MUCH TO OFFER A FAMILY, DEN, LIVING,ROOM, SUNROOM, 2 BEDROOMS,DOWN WITH 2 BATHS, LARGE BONUS ROOM UP WITH BATH, PLUS AN OFFICE AREA, FIREPLACE W/GAS LOGS IN DEN, LARGE FENCED IN BACKYARD FOR OUR FUR BABIES OR YOUR REGULAR BABIES AND SO MUCH MORE. THIS IS A MUCH SEE.

  Linda Carter Casey Realtors

  225 E Third St, Henderson, TN 38340
• 

  /2

  $85,000 Sold Sep 26, 2025

  278 Plunk St, Henderson, TN 38340

  • 3 Beds
  • 1 Bath
  • 1,036 Sq Ft
  • Built 1900

  Last Sold Summary

  • $82/SF

  Current Estimated Value $87,005

  Last Listing Agent Brandi Ragan Ragan Realty Group

  278 Plunk St, Henderson, TN 38340
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  /31

  Est $241,229 Not Listed For Sale

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

  6450 Old Jacks Creek Rd, Henderson, TN 38340

  6450 Old Jacks Creek Rd, Henderson, TN 38340
• 

  

  /29

  $399,900

  • 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
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  /38

  $465,000 Sold Apr 10, 2025

  40 E Wind Cove, Henderson, TN 38340

  • 5 Beds
  • 2.5 Baths
  • 2,691 Sq Ft
  • Built 2000

  Last Sold Summary

  • 3% Below List Price
  • $173/SF
  • 34 Days On Market

  Current Estimated Value $469,261

  Last Listing Agent Tami Reid Hickman Realty Group Inc.-Jack

  40 E Wind Cove, Henderson, TN 38340
• 

  

  /18

  Est $209,200 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,603 Sq Ft

  655 Glendale Rd, Henderson, TN 38340

  655 Glendale Rd, Henderson, TN 38340
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  /62

  $269,900 Pending

  • 6 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  208 Fourth St, Henderson, TN 38340

  208 Fourth St, Henderson, TN — Charming and spacious 6-bedroom, 2.5-bath home with an office, ideally located on a corner lot in the heart of Henderson and just a short walk to Freed-Hardeman University, Main Street, shopping, dining, and local amenities, this property offers both convenience and character. This beautifully updated home has been completely remodeled from top to bottom, featuring

  Richard Emison NextHome 383 Real Estate

  208 Fourth St, Henderson, TN 38340
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  /18

  $214,000 Sold Apr 11, 2025

  0 Cash School Rd, Enville, TN 38332

  Last Sold Summary

  • 22% Below List Price
  • 674 Days On Market

  Last Listing Agent Cole Murray Town and Country

  0 Cash School Rd, Enville, TN 38332
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  /42

  Est $406,253 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,041 Sq Ft

  470 Ludell Ross Rd, Enville, TN 38332

  470 Ludell Ross Rd, Enville, TN 38332
• 

  

  /22

  $550,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 5,944 Sq Ft

  230 Oak Ridge Dr, Henderson, TN 38340

  230 Oak Ridge Drive, space isn't just a luxury it's peace of mind. With six bedrooms, four and a half baths, and nearly 6,000 square feet on over 6 acres, this Oakmont Estates property was built for living well and breathing easy. The main level features two bedrooms including a serene primary suit, dining room, den, and living room with a gas-log fireplace. The freshly remodeled kitchen is

  Andrew Houston Coldwell Banker Southern Rlty

  230 Oak Ridge Dr, Henderson, TN 38340

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