Chester County, TN Homes

• 

  

  

  /53

  $319,000

  Sold Sep 18, 2025

  170 Tall Pines Rd, Henderson, TN 38340

  • 3 Beds
  • 2.5 Baths
  • 1,897 Sq Ft
  • Built 2005

  Last Sold Summary

  • 11% Below List Price
  • $168/SF
  • 28 Days On Market

  Current Estimated Value $346,042

  Last Listing Agent Linda Carter Casey Realtors

  170 Tall Pines Rd, Henderson, TN 38340
• 

  

  

  /44

  Est $247,134

  Not Listed For Sale

  2055 New Friendship Rd, Beech Bluff, TN 38313

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Built 1959

  2055 New Friendship Rd, Beech Bluff, TN 38313

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Blake Ward Coldwell Banker Southern Realty
• 

  

  

  /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
• 

  

  

  /8

  $39,000

  Sold Apr 29, 2026

  570 Hill Ave, Henderson, TN 38340

  • Land
  • 0 Sq Ft

  Last Sold Summary

  • 2% Below List Price
  • 3 Days On Market

  Last Listing Agent Zach Hannis Casey Realtors

  570 Hill Ave, Henderson, TN 38340
• 

  

  

  /18

  Est $286,635

  Not Listed For Sale

  160 Wilson School Rd, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1979

  160 Wilson School Rd, Henderson, TN 38340

  Last Sold Summary

  • 1 Day On Market

  Last Listing Agent Drake Harber Blue Suede Realty
• 

  

  /66

  $349,900

  $39K PRICE DROP

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

  450 North Ave, Henderson, TN 38340

  AT NO FAULT OF THE SELLERS , BACK ON THE MARKET, BUYER FINANCING FELL THROUGH, AND YOUR CHANCE TO MAKE IT YOURS! Step into timeless charm with this beautifully constructed home filled with original woodwork, hardwood floors, and character you simply can't recreate. With 5 bedrooms and 4 baths, there's plenty of room for everyone to spread out and feel at home. Need extra income or space for

  

  Destiny Burns

  Stellar Realty Group

  450 North Ave, Henderson, TN 38340
• 

  

  /22

  $255,000

  Sold Jan 09, 2026

  513 Crook Ave, Henderson, TN 38340

  • 2 Beds
  • 1 Bath
  • 1,200+ Sq Ft
  • Built 2022

  Last Sold Summary

  • 5% Below List Price
  • $212/SF
  • 64 Days On Market

  Current Estimated Value $247,953

  Last Listing Agent Ashton Roberts Molly Moore Realty

  513 Crook Ave, Henderson, TN 38340
• 

  

  /18

  Est $175,712

  Not Listed For Sale

  209 Tulip St, Henderson, TN 38340

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • Built 1971

  209 Tulip St, Henderson, TN 38340

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Lisa Davis Greer Real Estate Group
• 

  /2

  $241,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,251 Sq Ft

  618 Mifflin Ave, Henderson, TN 38340

  Welcome to your brand-new home in the highly anticipated Henderson Station subdivision! This stunning 3-bedroom, 2-bathroom property perfectly blends modern design with everyday functionality, starting with a welcoming front porch that offers excellent curb appeal for your morning coffee. Step inside to discover a bright, open-concept living area that flows seamlessly into a chef-inspired

  

  Melanie Malone

  Crye-Leike Elite

  618 Mifflin Ave, Henderson, TN 38340
• 

  

  /35

  $258,500

  Sold Jan 23, 2026

  210 Baker Rd, Henderson, TN 38340

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $140/SF
  • 16 Days On Market

  Last Listing Agent Aaliyah Cupples Stellar Realty Group

  210 Baker Rd, Henderson, TN 38340
• 

  

  /31

  Est $238,970

  Not Listed For Sale

  235 Pinecrest Dr, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1982

  235 Pinecrest Dr, Henderson, TN 38340

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Jessica Asberry EXIT Realty Blues City
• 

  

  /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
• 

  /2

  $225,000

  Sold Sep 05, 2025

  685 Plunk Rd, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • Built 1996

  Last Sold Summary

  Last Listing Agent Destiny Burns Stellar Realty Group

  685 Plunk Rd, Henderson, TN 38340
• 

  

  /25

  Est $250,084

  Not Listed For Sale

  315 Fish Pond Rd, Bethel Springs, TN 38315

  • 4 Beds
  • 2 Baths
  • 2,232 Sq Ft
  • Built 1970

  315 Fish Pond Rd, Bethel Springs, TN 38315

  Last Sold Summary

  • 145 Days On Market

  Last Listing Agent Brandi Isom RE/MAX Realty Source
• 

  /2

  $234,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,258 Sq Ft

  610 Mifflin Ave, Henderson, TN 38340

  Welcome to your brand-new home in the highly anticipated Henderson Station subdivision! This stunning 3-bedroom, 2.5 bathroom property perfectly blends modern design with everyday functionality, starting with a welcoming front porch that offers excellent curb appeal for your morning coffee. Step inside to discover a bright, open-concept living area that flows seamlessly into a chef-inspired

  

  Melanie Malone

  Crye-Leike Elite

  610 Mifflin Ave, Henderson, TN 38340
• 

  

  /28

  $279,000

  Sold Aug 29, 2025

  130 Old Sobby Rd, Bethel Springs, TN 38315

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

  Last Sold Summary

  • $199/SF
  • 6 Days On Market

  Current Estimated Value $394,000

  Last Listing Agent Brandi Isom RE/MAX Realty Source

  130 Old Sobby Rd, Bethel Springs, TN 38315
• 

  

  /27

  Est $242,956

  Not Listed For Sale

  766 Sand Ave, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1995

  766 Sand Ave, Henderson, TN 38340

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Madison Balding Town and Country
• 

  

  /82

  $159,900

  • 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: $159,900Owner 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

  Cave Springs Rd, Henderson, TN 38340
• 

  

  /29

  $462,900

  Sold Apr 08, 2026

  550 Trice Rd, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $189/SF
  • 90 Days On Market

  Last Listing Agent Brandi Isom RE/MAX Realty Source

  550 Trice Rd, Henderson, TN 38340
• 

  

  /33

  Est $429,534

  Not Listed For Sale

  40 Meadows Access, Henderson, TN 38340

  • 3 Beds
  • 2.5 Baths
  • 2,687 Sq Ft
  • Built 1999

  40 Meadows Access, Henderson, TN 38340

  Last Sold Summary

  • 240 Days On Market

  Last Listing Agent Dessie Hardee RE/MAX Realty Source
• 

  

  /16

  $93,100

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

  2404 Grooms Rd, 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

  Austin Carroll Tutt Land Company

  2404 Grooms Rd, Henderson, TN 38340
• 

  

  /9

  $128,000

  Sold Feb 02, 2026

  961 Woodland Dr, Henderson, TN 38340

  • 1,656 Sq Ft
  • Built 1975

  Last Sold Summary

  • 20% Below List Price
  • $77/SF
  • 17 Days On Market

  Current Estimated Value $136,203

  Last Listing Agent Zach Hannis Casey Realtors

  961 Woodland Dr, Henderson, TN 38340
• 

  

  /16

  Est $202,357

  Not Listed For Sale

  695 Jacks Creek Cove, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,138 Sq Ft
  • Built 2001

  695 Jacks Creek Cove, Henderson, TN 38340

  Last Sold Summary

  Last Listing Agent Jennifer Scott RE/MAX Realty Source
• 

  

  /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
• 

  

  /55

  $550,000

  Sold Dec 05, 2025

  165 Hunters Glen Ln, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 2,638 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Below List Price
  • $208/SF
  • 98 Days On Market

  Current Estimated Value $559,749

  Last Listing Agent Destiny Burns Stellar Realty Group

  165 Hunters Glen Ln, Henderson, TN 38340
• 

  

  /23

  Est $217,543

  Not Listed For Sale

  825 Sanford St, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 1975

  825 Sanford St, Henderson, TN 38340

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Jon Putt Putt Real Estate Advisors
• 

  

  /32

  $95,000

  • 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: $95,000Reservation 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
• 

  

  /25

  $200,250

  Sold Apr 13, 2026

  380 Patterson Ln, Finger, TN 38334

  • 4 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1979

  Last Sold Summary

  • $174/SF
  • 128 Days On Market

  Current Estimated Value $196,699

  Last Listing Agent Richard Emison NextHome 383 Real Estate

  380 Patterson Ln, Finger, TN 38334
• 

  

  /36

  Est $516,018

  Not Listed For Sale

  855 Rabbit Ranch Rd, Henderson, TN 38340

  • 4 Beds
  • 3 Baths
  • 3,220 Sq Ft
  • Built 2004

  855 Rabbit Ranch Rd, Henderson, TN 38340

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Brooke Baker Greer Real Estate Group
• 

  

  /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
• 

  

  /14

  $30,000

  Sold Jun 25, 2026

  2975 State Route 100 W, Henderson, TN 38340

  • Land
  • 41,382 Sq Ft
  • $31,579 per Acre

  Last Sold Summary

  • 14% Below List Price
  • 237 Days On Market

  Current Estimated Value $178,787

  Last Listing Agent Destiny Burns Stellar Realty Group

  2975 State Route 100 W, Henderson, TN 38340
• 

  

  /27

  Est $209,855

  Not Listed For Sale

  165 North Rd, Enville, TN 38332

  • 4 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • Built 1994

  165 North Rd, Enville, TN 38332

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Xavier Crane 2 Cranes Realty
• 

  

  /10

  $899,900

  80 Proctor Rd, Henderson, TN 38340

  Discover a gorgeous 108 acres offering the perfect blend of open pasture, water, woods, and functionality. The property features cross fencing with seperated pastures, ponds, a shop with two bays, and underground utilities already in place. Wooded trails wind throughout the acreage, creating opportunities for horseback riding, ATVs, hunting, or simply enjoying the privacy and natural beauty of

  Alan Castleman Hickman Realty Group Inc

  80 Proctor Rd, Henderson, TN 38340
• 

  

  /26

  $210,700

  Sold Sep 24, 2025

  70 E Haven Ln, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,318 Sq Ft
  • Built 2009

  Last Sold Summary

  • 3% Above List Price
  • $160/SF
  • 1 Day On Market

  Current Estimated Value $222,773

  Last Listing Agent Destiny Burns Stellar Realty Group

  70 E Haven Ln, Henderson, TN 38340
• 

  

  /38

  Est $477,786

  Not Listed For Sale

  40 E Wind Cove, Henderson, TN 38340

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

  40 E Wind Cove, Henderson, TN 38340

  Last Sold Summary

  • 34 Days On Market

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

  

  /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
• 

  

  /21

  $379,900

  Sold Dec 19, 2025

  135 Fox Run Cove, Henderson, TN 38340

  • 4 Beds
  • 3 Baths
  • 2,437 Sq Ft
  • Built 2007

  Last Sold Summary

  • 10% Below List Price
  • $156/SF
  • 52 Days On Market

  Current Estimated Value $406,557

  Last Listing Agent Melanie Malone Crye-Leike Elite

  135 Fox Run Cove, Henderson, TN 38340
• 

  

  /38

  Est $315,257

  Not Listed For Sale

  390 Julian Ln, Pinson, TN 38366

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft
  • Built 1935

  390 Julian Ln, Pinson, TN 38366

  Last Sold Summary

  • 466 Days On Market

  Last Listing Agent Judy McLean Farm & Home Realty
• 

  

  /31

  $399,000

  $25K PRICE DROP

  • Land
  • 105 Acres
  • $3,800 per Acre

  935 Big Rock Trail, Henderson, TN 38340

  105 AC. BIG ROCK TRAIL, HENDERSON TN. OFF THE GRID LIVING Want to truly get away from it all? Look no further—this is as private and secluded as it gets. Tucked away at the end of a 1.5-mile winding driveway with no thru traffic, this incredible 105-acre retreat borders Chickasaw State Park—offering unmatched peace, privacy, and natural beauty. NO neighbors just you and nature. PROPERTY

  Jeremy Ryan Crye-Leike, Inc., REALTORS

  935 Big Rock Trail, Henderson, TN 38340
• 

  

  /19

  $52,000

  Sold Aug 07, 2026

  167 W Third St, Henderson, TN 38340

  • 3 Beds
  • 2 Baths
  • 1,746 Sq Ft
  • Built 1940

  Last Sold Summary

  • $30/SF
  • 8 Days On Market

  Current Estimated Value $216,905

  Last Listing Agent Tabatha Bell Coldwell Banker McKee Realty

  167 W Third St, Henderson, TN 38340

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