Chester County, TN Homes

• 

  

  

  /27

  $299,000

  $81K PRICE DROP 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
• 

  

  

  /24

  $439,900

  Sold Jul 25, 2025

  2845 Sanford Rd, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,583 Sq Ft
  • Built 2000

  Last Sold Summary

  • $278/SF
  • 18 Days On Market

  Current Estimated Value $397,130

  Last Listing Agent Jon Putt Putt Real Estate Advisors

  2845 Sanford Rd, Henderson, TN 38340
• 

  

  

  /26

  Est $247,545

  Not Listed For Sale

  722 Hearn St, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,477 Sq Ft
  • Built 2002

  722 Hearn St, Henderson, TN 38340

  Last Sold Summary

  • 46 Days On Market
• 

  

  

  /28

  $258,000

  New Construction

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  3045 Clifford Rd, Luray, TN 38352

  Welcome to 3045 Clifford Road in Luray! This brand-new mobile home offers the perfect blend of modern style, thoughtful design, and country living on a full one-acre lot. Inside, you'll find 3 bedrooms plus a bonus room, 2 full bathrooms, and luxury vinyl plank flooring throughout. The open-concept living area features a custom accent wall and flows seamlessly into the kitchen, complete with

  Julie Holt Blue Suede Realty

  3045 Clifford Rd, Luray, TN 38352
• 

  

  

  /43

  $514,900

  Sold Dec 23, 2025

  175 Ridgewood Dr, Henderson, TN 38340

  • 5 Beds
  • 3.5 Baths
  • 3,194 Sq Ft
  • Built 2017

  Last Sold Summary

  • 1% Below List Price
  • $161/SF
  • 20 Days On Market

  Current Estimated Value $503,868

  Last Listing Agent Michelle Lilly Lilly Realty

  175 Ridgewood Dr, Henderson, TN 38340
• 

  

  /4

  Est $170,180

  Not Listed For Sale

  1041 W Main St, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft
  • Built 1947

  1041 W Main St, Henderson, TN 38340

  Last Sold Summary

  • 6 Days On Market
• 

  

  /29

  $112,000

  $18K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,164 Sq Ft

  225 Capps Ln, Pinson, TN 38366

  Quiet country living in this 3 BR 2 BA Chester County home, with no city taxes. Ideal for first-time buyers or investors, offering a blend of serenity and financial potential. Quiet country living in this 3 BR 2 BA Chester County home, with no city taxes. Ideal for first-time buyers or investors, offering a blend of serenity and financial potential.

  Zach Hannis Casey Realtors

  225 Capps Ln, Pinson, TN 38366
• 

  

  /40

  $558,700

  Sold Feb 24, 2026

  10430 State Route 100 W, Henderson, TN 38340

  • 3 Beds
  • 2.5 Baths
  • 2,200+ Sq Ft
  • Built 1993

  Last Sold Summary

  • 9% Below List Price
  • $254/SF
  • 154 Days On Market

  Current Estimated Value $506,657

  Last Listing Agent Joseph Cummings Epique Realty

  10430 State Route 100 W, Henderson, TN 38340
• 

  

  /28

  Est $221,468

  Not Listed For Sale

  105 Simmons St, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 1940

  105 Simmons St, Henderson, TN 38340

  Last Sold Summary

  • 21 Days On Market
• 

  

  /15

  $90,000

  $10K PRICE DROP Pending

  • Land
  • 17.18 Acres
  • $5,239 per Acre

  0 Sanford Rd, Henderson, TN 38340

  Located just outside Henderson city limits on Sanford Road, this 17.18-acre property offers a rare combination of natural water features and flexible zoning options. The parcel features a creek flowing consistently across one side of the property, Farm Agricultural Residential (FAR) zoning that allows for multiple development options, and complete readiness for residential construction with

  Kevin Gioia BEYCOME BROKERAGE REALTY, LLC

  0 Sanford Rd, Henderson, TN 38340
• 

  

  /32

  $469,900

  Sold Nov 21, 2025

  137 Gibson Dr, Henderson, TN 38340

  • 4 Beds
  • 3 Baths
  • 2,720 Sq Ft
  • Built 1952

  Last Sold Summary

  • 6% Below List Price
  • $173/SF
  • 118 Days On Market

  Current Estimated Value $443,175

  Last Listing Agent Brent West Crye-Leike Elite

  137 Gibson Dr, Henderson, TN 38340
• 

  

  /29

  Est $243,125

  Not Listed For Sale

  198 Stewart Ave, Henderson, TN 38340

  • 3 Beds
  • 3 Baths
  • 1,855 Sq Ft
  • Built 1968

  198 Stewart Ave, Henderson, TN 38340

  Last Sold Summary

  • 107 Days On Market
• 

  

  /11

  $85,000

  • Land
  • 22 Acres
  • $3,864 per Acre

  225 Henderson Rd, Henderson, TN 38340

  22 Acres - Chester County A blank canvas in the country! 22 acres of raw land ready for your dream home, hunting spot, investment or weekend retreat! Peace, space, and endless possibilities.

  Dustin Insell Coldwell Banker Southern Realty

  225 Henderson Rd, Henderson, TN 38340
• 

  

  /22

  $240,000

  Sold Dec 30, 2025

  457 Kendyl Cove, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,555 Sq Ft
  • Built 2008

  Last Sold Summary

  • 8% Below List Price
  • $154/SF
  • 33 Days On Market

  Current Estimated Value $244,530

  Last Listing Agent Raven Taylor BHGRE Conner Jackson

  457 Kendyl Cove, Henderson, TN 38340
• 

  

  /10

  Est $154,000

  Not Listed For Sale

  5330 Cash School Rd, Enville, TN 38332

  • 3 Beds
  • 1 Bath
  • 1,351 Sq Ft
  • Built 1967

  5330 Cash School Rd, Enville, TN 38332

  Last Sold Summary

  • 130 Days On Market
• 

  

  /30

  $245,000

  • 3 Beds
  • 2 Baths
  • 1,850 Sq Ft

  320 Benson Rd, Reagan, TN 38368

  Welcome home to this beautifully updated 3-bedroom, 2-bath property nestled on 2.17 acres of peaceful, wooded surroundings! This home features an inviting open floor plan perfect for everyday living and entertaining, highlighted by a fully updated kitchen with granite countertops, stainless steel appliances, new cabinetry, and a stylish coffee bar. Need extra space? You'll love the additional

  Andrea Crawford RE/MAX Unlimited

  320 Benson Rd, Reagan, TN 38368
• 

  

  /22

  $126,800

  Sold May 14, 2026

  456 Galbraith Ave, Henderson, TN 38340

  • 4 Beds
  • 2 Baths
  • 2,138 Sq Ft
  • Built 1958

  Last Sold Summary

  • 21% Below List Price
  • $59/SF
  • 63 Days On Market

  Current Estimated Value $140,554

  Last Listing Agent John Alsobrook Pritchard Realty

  456 Galbraith Ave, Henderson, TN 38340
• 

  

  /48

  Est $435,993

  Not Listed For Sale

  735 Benson Rd, Reagan, TN 38368

  • 5 Beds
  • 3 Baths
  • 3,600 Sq Ft
  • Built 1973

  735 Benson Rd, Reagan, TN 38368

  Last Sold Summary

  • 191 Days On Market
• 

  

  /34

  $239,900

  Open House 7/26 $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,870 Sq Ft

  484 White Ave, Henderson, TN 38340

  Please see the Virtual tour. Roof 2 weeks old, Window World Windows about 2 years old, all copper plumbing replaced three years ago, beautiful home conveniently located to Freed Hardeman and downtown Henderson. Home features custom built kitchen cabinetry. There is not a wall separating the Kitchen form the Dining area. It is actually a large 24x12 single room. The large deck is custom-built with

  Garry Carroll Crye-Leike Elite

  484 White Ave, Henderson, TN 38340
• 

  

  /21

  $184,800

  Sold Jan 23, 2026

  0 Grooms Rd Unit PT-14, Henderson, TN 38340

  • Land
  • 84 Acres
  • $2,200 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 39 Days On Market

  Last Listing Agent Austin Carroll Tutt Land Company

  0 Grooms Rd Unit PT-14, Henderson, TN 38340
• 

  

  /25

  Est $242,027

  Not Listed For Sale

  2410 Carroll Rd, Enville, TN 38332

  • Built 1960

  2410 Carroll Rd, Enville, TN 38332

  Last Sold Summary

  • 121 Days On Market
• 

  

  /23

  $195,000

  $25K PRICE DROP

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

  318 Mifflin Ave, Henderson, TN 38340

  Welcome home to this beautifully updated gem right in the heart of Henderson! From the moment you walk in, you'll feel the warmth and coziness this home has to offer. The seller has thoughtfully updated the home throughout with gorgeous new kitchen cabinets, countertops, updated bathroom vanities, new flooring, new siding, and a brand-new HVAC system for peace of mind. The inviting kitchen flows

  Jennifer Scott RE/MAX Realty Source

  318 Mifflin Ave, Henderson, TN 38340
• 

  /2

  $285,000

  Sold Jun 19, 2026

  474 Old Jackson Rd, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • Built 2026

  Last Sold Summary

  • $201/SF
  • 0 Days On Market

  Last Listing Agent Brent West Crye-Leike Elite

  474 Old Jackson Rd, Henderson, TN 38340
• 

  

  /39

  Est $468,634

  Not Listed For Sale

  150 Tall Pines Rd, Henderson, TN 38340

  • 4 Beds
  • 3.5 Baths
  • 2,660 Sq Ft
  • Built 2006

  150 Tall Pines Rd, Henderson, TN 38340

  Last Sold Summary

  • 26 Days On Market
• 

  

  /33

  $199,900

  $30K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft

  444 Galbraith Ave, Henderson, TN 38340

  This charming two-bedroom, two-bath home offers generous living space and thoughtful design, featuring a large office with built-in bookshelves, a sunroom, a formal living room with a beautiful fireplace, a dining room, and a cozy breakfast nook. The residence includes a spacious walkout basement and multiple sitting areas that invite you to enjoy the surrounding nature. A well-appointed backyard

  Zach Hannis Casey Realtors

  444 Galbraith Ave, Henderson, TN 38340
• 

  /2

  $35,000

  Sold Mar 05, 2026

  636 Mifflin Ave, Henderson, TN 38340

  • Land
  • 0 Sq Ft

  Last Sold Summary

  Last Listing Agent Tiffany Elder Porchlight Realty West TN

  636 Mifflin Ave, Henderson, TN 38340
• 

  

  /32

  Est $445,407

  Not Listed For Sale

  5370 State Route 100 E, Henderson, TN 38340

  • 5 Beds
  • 3 Baths
  • 3,411 Sq Ft
  • Built 1974

  5370 State Route 100 E, Henderson, TN 38340

  Last Sold Summary

  • 208 Days On Market
• 

  

  /24

  $250,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  125 Benson Ln, Luray, TN 38352

  Move-in ready home loaded with updates! Enjoy a beautifully renovated kitchen & bathrooms, stainless appliances, and new luxury vinyl floors throughout. The spacious family room features soaring vaulted ceilings and flows into a large pantry and separate laundry room. Rest easy with a new roof, windows, gutters & newer HVAC. The primary suite offers double closets, including a walk-in. Nothing to

  Todd Haltom Haltom Real Estate Group

  125 Benson Ln, Luray, TN 38352
• 

  

  /62

  $273,900

  Sold Feb 13, 2026

  208 Fourth St, Henderson, TN 38340

  • 6 Beds
  • 2.5 Baths
  • 2,290 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Above List Price
  • $120/SF
  • 21 Days On Market

  Current Estimated Value $275,219

  Last Listing Agent Richard Emison NextHome 383 Real Estate

  208 Fourth St, Henderson, TN 38340
• 

  

  /26

  Est $261,180

  Not Listed For Sale

  330 Courtney Cove, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft
  • Built 2007

  330 Courtney Cove, Henderson, TN 38340

  Last Sold Summary

  • 2 Days On Market
• 

  

  /9

  $269,000

  $16K PRICE DROP

  • Land
  • 0 Sq Ft

  X Cedar Brook Ln, Henderson, TN 38340

  Discover 63 acres of wooded landscape offering privacy and natural beauty just minutes from the conveniences of Henderson. The property features multiple potential building sites surrounded by mature trees and abundant wildlife. An entrance is located on Cedar Brook Lane, providing easy access while maintaining a peaceful country setting. Whether you're looking for a future home site,

  Sheila Darnell EXIT Realty Blues City

  X Cedar Brook Ln, Henderson, TN 38340
• 

  

  /14

  $175,000

  Sold Jan 21, 2026

  234 Tulip St, Henderson, TN 38340

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Below List Price
  • $163/SF
  • 47 Days On Market

  Current Estimated Value $174,295

  Last Listing Agent Linda Carter Casey Realtors

  234 Tulip St, Henderson, TN 38340
• 

  

  /13

  Est $161,966

  Not Listed For Sale

  450 Second St, Henderson, TN 38340

  • 3 Beds
  • 1 Bath
  • 1,171 Sq Ft
  • Built 1964

  450 Second St, Henderson, TN 38340

  Last Sold Summary

  • 4 Days On Market
• 

  

  /16

  $93,100

  • Land
  • 38 Acres
  • $2,450 per Acre

  2181 Grooms Rd Unit PT-13, Henderson, TN 38340

  This 38+/- acre tract in southwest Chester County offers a diverse mixture of hunting, recreation, and potential homesites. With approximately 900 feet of frontage on Grooms Road and a private shared-use easement road forming the western boundary, the property has practical access and multiple ways to approach future layout, hunting access, or site planning. The land is made up of approximately 6

  Austin Carroll Tutt Land Company

  2181 Grooms Rd Unit PT-13, Henderson, TN 38340
• 

  

  /35

  $475,000

  Sold Mar 13, 2026

  495 Tennessee 22 Alternate, Jacks Creek, TN 38347

  • 3 Beds
  • 3 Baths
  • 1,400+ Sq Ft
  • Built 1959

  Last Sold Summary

  • 32% Below List Price
  • $339/SF
  • 212 Days On Market

  Last Listing Agent Marisa Casteel BST Realty

  495 Tennessee 22 Alternate, Jacks Creek, TN 38347
• 

  

  /48

  Est $625,404

  Not Listed For Sale

  370 Meadows Ln, Henderson, TN 38340

  • 3 Beds
  • 3 Baths
  • 4,200 Sq Ft
  • Built 1978

  370 Meadows Ln, Henderson, TN 38340

  Last Sold Summary

  • 283 Days On Market
• 

  

  /14

  $58,000

  Pending

  • Land
  • 8.84 Acres
  • $6,561 per Acre

  TRACT 5 Highway 22 A, Jacks Creek, TN 38347

  $1000 DOWN & NO CREDIT CHECKS - ONLY $500/MTH 8.84 ACRES - LAND FOR SALE – JACKS CREEK, TN ?? TRACT 5 HWY 22A JACKS CREEK, TN Affordable land with natural beauty and water on-site These tracts in Jacks Creek, TN offer a great mix of road frontage, wooded privacy, and creek runs through the property. The front of this property is high and dry but the back of this property is in a FLOOD ZONE - SEE

  Timothy Crane 2 Cranes Realty

  TRACT 5 Highway 22 A, Jacks Creek, TN 38347
• 

  

  /65

  $479,900

  Sold Dec 23, 2025

  240 Greystone CV St, Henderson, TN 38340

  • 3 Beds
  • 2.5 Baths
  • 2,338 Sq Ft
  • Built 2022

  Last Sold Summary

  • 4% Below List Price
  • $205/SF
  • 91 Days On Market

  Last Listing Agent Destiny Burns Stellar Realty Group

  240 Greystone CV St, Henderson, TN 38340
• 

  

  /8

  Est $185,322

  Not Listed For Sale

  158 N Franklin Ave, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 2024

  158 N Franklin Ave, Henderson, TN 38340

  Last Sold Summary

  • 63 Days On Market
• 

  

  /27

  $315,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,818 Sq Ft

  746 Mason Ave, Henderson, TN 38340

  Welcome to 746 Mason Ave — a warm and inviting 3-bedroom, 2-bath brick haven that truly feels like home from the moment you arrive! Located in a lovely, family friendly neighborhood in the heart of Henderson, this great property offers a comfortable layout with spacious living areas featuring a split floor plan, a cozy fireplace, and plenty of room to gather with family and friends. Step outside

  Jennifer Maness-Scott Coldwell Banker Southern Realty

  746 Mason Ave, Henderson, TN 38340

Showing Results 281 - 320, Page 8 of 18