Chester County, TN Homes

• 

  

  

  /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

  Lot 8 Greystone Cove, Henderson, TN 38340
• 

  

  

  /6

  $1,050 Per Month

  • 2 Beds
  • 1 Bath
  • Apartment for Rent

  320 Samantha Cove, Henderson, TN 38340

  Discover your serene retreat in this 2 bedroom, 1 bathroom duplex, boasting a peaceful atmosphere and convenient location. The interior boasts sleek LVP flooring in the living room, bathroom, and kitchen, plus fresh paint throughout. The kitchen is equipped with appliances for effortless meal prep. Ample parking space is available, and lawn maintenance is included for added convenience. This is a

  Brooke Redmon Benton Action Realty

  320 Samantha Cove, Henderson, TN 38340
• 

  

  

  /18

  $400,000

  Sold Oct 29, 2025

  1450 Busby Ln, Henderson, TN 38340

  • Land
  • 91.7 Acres
  • $4,362 per Acre

  Last Sold Summary

  • 21% Below List Price
  • 153 Days On Market

  Last Listing Agent Robert Eatman Hickman Realty Group Inc.-Jack

  1450 Busby Ln, Henderson, TN 38340
• 

  

  

  /27

  Est $251,182

  Not Listed For Sale

  195 Simmons St, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • Built 2015

  195 Simmons St, Henderson, TN 38340

  Last Sold Summary

  • 252 Days On Market
• 

  

  

  /39

  $210,000

  $89K PRICE DROP Pending

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

  6525 State Route 225, Henderson, TN 38340

  Extremely motivated sellers, selling as is! 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 of mind.

  

  Destiny Burns

  Stellar Realty Group

  6525 State Route 225, Henderson, TN 38340
• 

  /2

  $30,000

  Sold Nov 05, 2025

  4875 Clifford Rd, Luray, TN 38352

  • Land
  • 6.28 Acres
  • $4,777 per Acre

  Last Sold Summary

  Current Estimated Value $85,464

  Last Listing Agent Brandi Ragan Ragan Realty Group

  4875 Clifford Rd, Luray, TN 38352
• 

  

  /20

  Est $201,927

  Not Listed For Sale

  1341 Old Jacks Creek Rd, Henderson, TN 38340

  • 3 Beds
  • 1.5 Baths
  • 1,526 Sq Ft
  • Built 1906

  1341 Old Jacks Creek Rd, Henderson, TN 38340

  Last Sold Summary

  • 79 Days On Market
• 

  /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

  0 Old Sobby Rd, Bethel Springs, TN 38315
• 

  

  /14

  $235,000

  Sold Sep 10, 2025

  1280 Mockingbird Rd, Medon, TN 38356

  • 2 Beds
  • 2 Baths
  • 1,388 Sq Ft
  • Built 1995

  Last Sold Summary

  • 3% Above List Price
  • $169/SF
  • 0 Days On Market

  Current Estimated Value $235,646

  Last Listing Agent Brandi Wilson RE/MAX Realty Source

  1280 Mockingbird Rd, Medon, TN 38356
• 

  

  /6

  Est $173,554

  Not Listed For Sale

  60 Stewart Rd, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • Built 2009

  60 Stewart Rd, Henderson, TN 38340

  Last Sold Summary
• 

  

  /38

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,642 Sq Ft

  3290 Silerton Rd, Henderson, TN 38340

  Exquisite custom built home in Chester County with 3 car garage on 10 acres! This open floorplan offers a chefs dream kitchen with high end stainless appliances, large great room for entertaining with corner gas fireplace, tankless water heater, upgraded sprayed foam insulation for efficiency, lots of outdoor entertaining areas including covered front and back porches and side court yard area. So

  

  Ben Roberts

  RE/MAX Realty Source

  3290 Silerton Rd, Henderson, TN 38340
• 

  

  /3

  $35,000

  Sold Sep 03, 2025

  0 LOT 2 W 3rd St, Henderson, TN 38340

  • Land
  • 0 Sq Ft

  Last Sold Summary

  • 3% Below List Price
  • 0 Days On Market

  Last Listing Agent Linda Carter Casey Realtors

  0 LOT 2 W 3rd St, Henderson, TN 38340
• 

  

  /14

  Est $235,326

  Not Listed For Sale

  870 Simmons Rd, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • Built 2009

  870 Simmons Rd, Henderson, TN 38340

  Last Sold Summary

  • 69 Days On Market
• 

  

  /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

  285 Cedar Brook Ln, Henderson, TN 38340
• 

  

  /34

  $205,000

  Sold Oct 06, 2025

  175 S State Route 22a S St, Jacks Creek, TN 38347

  • 3 Beds
  • 2 Baths
  • 2,146 Sq Ft
  • Built 1900

  Last Sold Summary

  • 37% Below List Price
  • $96/SF

  Current Estimated Value $183,715

  175 S State Route 22a S St, Jacks Creek, TN 38347
• 

  

  /15

  Est $339,471

  Not Listed For Sale

  540 Moss Loop, Enville, TN 38332

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 2009

  540 Moss Loop, Enville, TN 38332

  Last Sold Summary

  • 158 Days On Market
• 

  

  /25

  $239,900

  $240K PRICE INCREASE Pending

  • 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

  707 Mifflin Avenue Extension, Henderson, TN 38340
• 

  

  /20

  $158,000

  Sold Jun 30, 2026

  11350 State Route 100 E, Reagan, TN 38368

  • 1 Bed
  • 1 Bath
  • 1,387 Sq Ft
  • Built 2004

  Last Sold Summary

  • 15% Below List Price
  • $114/SF
  • 52 Days On Market

  Current Estimated Value $183,212

  Last Listing Agent Jennifer Greer Greer Real Estate Group

  11350 State Route 100 E, Reagan, TN 38368
• 

  

  /25

  Est $226,162

  Not Listed For Sale

  75 Bray Ln, Beech Bluff, TN 38313

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft
  • Built 2009

  75 Bray Ln, Beech Bluff, TN 38313

  Last Sold Summary

  • 29 Days On Market
• 

  

  /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!

  

  Lori Yarbro

  Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
• 

  

  /23

  $235,000

  Sold Feb 13, 2026

  337 Morning View Cove, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $169/SF
  • 36 Days On Market

  Current Estimated Value $238,072

  Last Listing Agent Jennifer Scott RE/MAX Realty Source

  337 Morning View Cove, Henderson, TN 38340
• 

  

  /23

  Est $255,982

  Not Listed For Sale

  290 Bray Ln, Beech Bluff, TN 38313

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft
  • Built 2009

  290 Bray Ln, Beech Bluff, TN 38313

  Last Sold Summary

  • 30 Days On Market
• 

  

  /35

  $480,000

  • Land
  • 143.34 Acres
  • $3,349 per Acre

  0 Highway 22 A, Enville, TN 38332

  Don’t miss this rare opportunity to own 143.34 unrestricted acres in a fantastic location just off Hwy 22 in Enville, Tennessee. This versatile tract offers convenient access to Lexington, Henderson, and Adamsville while still providing the privacy, nature, and wide-open space buyers are looking for. With electricity available at the road and multiple ideal building sites, this property is

  

  Lori Yarbro

  Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
• 

  

  /37

  $245,000

  Sold Sep 22, 2025

  3605 Old Jacks Creek Rd, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 1979

  Last Sold Summary

  • 8% Below List Price
  • $165/SF
  • 95 Days On Market

  Current Estimated Value $248,911

  Last Listing Agent Sheila Darnell EXIT Realty Blues City

  3605 Old Jacks Creek Rd, Henderson, TN 38340
• 

  

  /36

  Est $298,611

  Not Listed For Sale

  280 Bray Ln, Beech Bluff, TN 38313

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft
  • Built 2009

  280 Bray Ln, Beech Bluff, TN 38313

  Last Sold Summary

  • 76 Days On Market
• 

  

  /42

  $249,000

  • 2 Beds
  • 1 Bath
  • 1,279 Sq Ft

  470 North Ave, Henderson, TN 38340

  This Charming Cottage is perfect for those seeking a Home with a heart. This beautiful Home features vintage details throughout, a cozy fireplace, original hardwood, stone counters, spacious backyard, plenty of natural light, hydrangeas, large front porch, and all the attention to details that will make you feel like you are living in a storybook! If you are looking for a beautiful Home that

  

  Destiny Burns

  Stellar Realty Group

  470 North Ave, Henderson, TN 38340
• 

  

  /3

  $160,000

  Sold Apr 23, 2026

  00 Highway 45 S, Henderson, TN 38340

  • Land
  • 2.7 Acres
  • $59,259 per Acre

  Last Sold Summary

  • 38% Below List Price
  • 245 Days On Market

  Last Listing Agent Craig Casey Casey Realtors

  00 Highway 45 S, Henderson, TN 38340
• 

  

  /51

  Est $265,603

  Not Listed For Sale

  280 Bray Rd, Beech Bluff, TN 38313

  • Studio
  • 1,518 Sq Ft
  • Built 2009

  280 Bray Rd, Beech Bluff, TN 38313

  Last Sold Summary

  • 49 Days On Market
• 

  

  /34

  $319,900

  Pending

  • 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

  766 Mason Ave, Henderson, TN 38340
• 

  /2

  $30,000

  Sold Jan 22, 2026

  145 Parson Ln, Jacks Creek, TN 38347

  • Land
  • 1.18 Acres
  • $25,424 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 35 Days On Market

  Last Listing Agent Richard Emison NextHome 383 Real Estate

  145 Parson Ln, Jacks Creek, TN 38347
• 

  

  /40

  Est $168,816

  Not Listed For Sale

  10680 State Route 22a S, Enville, TN 38332

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1979

  10680 State Route 22a S, Enville, TN 38332

  Last Sold Summary

  • 11 Days On Market
• 

  

  /23

  $150,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  304 Mifflin Ave, Henderson, TN 38340

  Discover the perfect blend of convenience and affordability in this move-in-ready home just steps from Freed-Hardeman University and minutes from downtown Henderson. This inviting 2-bedroom, single-story home is ideal for anyone seeking an easy, low-maintenance lifestyle. Offering just under 1,000 square feet, the home features comfortable living areas and an eat-in kitchen with abundant cabinet

  

  Brandi Wilson

  RE/MAX Realty Source

  304 Mifflin Ave, Henderson, TN 38340
• 

  

  /56

  $445,000

  Sold Jun 18, 2026

  130 Moss Loop, Enville, TN 38332

  • 4 Beds
  • 3 Baths
  • 1,916 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $232/SF
  • 47 Days On Market

  Current Estimated Value $386,000

  Last Listing Agent Tiffany Elder Porchlight Realty West TN

  130 Moss Loop, Enville, TN 38332
• 

  

  /33

  Est $264,998

  Not Listed For Sale

  360 Jacks Creek St, Henderson, TN 38340

  • 3 Beds
  • 2.5 Baths
  • 2,050 Sq Ft
  • Built 1989

  360 Jacks Creek St, Henderson, TN 38340

  Last Sold Summary

  • 113 Days On Market
• 

  

  /9

  $49,900

  $5K PRICE DROP

  • Land
  • 5.5 Acres
  • $9,073 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

  00 Old State Highway 22a, Enville, TN 38332
• 

  

  /26

  $365,000

  Sold Mar 20, 2026

  316 Meadow Brook Dr, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft
  • Built 2010

  Last Sold Summary

  • 6% Below List Price
  • $191/SF
  • 279 Days On Market

  Current Estimated Value $373,448

  Last Listing Agent Destiny Burns Stellar Realty Group

  316 Meadow Brook Dr, Henderson, TN 38340
• 

  

  /45

  Est $451,510

  Not Listed For Sale

  215 Harris Ln, Henderson, TN 38340

  • 4 Beds
  • 2.5 Baths
  • 2,614 Sq Ft
  • Built 1990

  215 Harris Ln, Henderson, TN 38340

  Last Sold Summary

  • 25 Days On Market
• 

  

  /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

  Lot 7 Greystone Cove, Henderson, TN 38340
• 

  

  /6

  $30,000

  Sold Aug 01, 2025

  217 McGee Trail, Henderson, TN 38340

  • Land
  • 5 Acres
  • $6,000 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 108 Days On Market

  Last Listing Agent Bryana Harris William Wilson Homes

  217 McGee Trail, Henderson, TN 38340
• 

  

  /31

  Est $150,721

  Not Listed For Sale

  11555 State Route 22a S, Enville, TN 38332

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 1959

  11555 State Route 22a S, Enville, TN 38332

  Last Sold Summary

  • 123 Days On Market

Showing Results 1 - 40, Page 1 of 18