Chester County TN Homes for Sale

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  /34

  $269,900

  • 4 Beds
  • 3 Baths
  • 1,568 Sq Ft

  170 Leapwood Dr, Enville, TN 38332

  Wow! What a deal! 13.8 acres. 2 parcels 2.3 acres and 11.5 acres 4 bedrooms 3 full baths completely renovated! New laminate through out the house! All new kitchen appliances, cabinets, bathroom fixtures, new lights throughout, new hot water. Ac unit! Fresh paint! Nice covered front and back porch! Over sized double garage with an attached RV storage! Plus an extra structural on the property that

  Hattie Davidson Brawley 2 Rivers Realty, LLC

  170 Leapwood Dr, Enville, TN 38332
• 

  

  

  /7

  $169,900

  • Land
  • 50.1 Acres
  • $3,391 per Acre

  0 Arl Bailey Rd, Finger, TN 38334

  Located entirely in Chester County, TN, this approximately 50.1 acre parcel was surveyed in 2021 and features roughly a quarter mile of road frontage with power and fiber internet already available via the utility easement on the property. A septic system and well would be needed, with local well drillers indicating water is typically found at approximately 80 to 100 feet, and the property also

  Daniel Demers Sell Your Home Services, LLC

  0 Arl Bailey Rd, Finger, TN 38334
• 

  

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /16

  $65,500

  • Land
  • 7.28 Acres
  • $8,997 per Acre

  00 Old Lula Rd, Reagan, TN 38368

  Looking for the perfect place to build without the work of clearing land? This beautiful 7.28-acre tract on Old Lula Road is already off to a great start. With approximately 702 feet of road frontage, a cleared driveway, and a 90' x 100' homesite already established, much of the groundwork has been completed. Surrounded by mature timber and peaceful countryside, this property offers the ideal

  Jennifer Scott RE/MAX Realty Source

  00 Old Lula Rd, Reagan, TN 38368
• 

  

  /39

  $210,000

  $89K PRICE DROP

  • 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
• 

  

  /18

  $141,500

  • Land
  • 15.71 Acres
  • $9,007 per Acre

  0 Old Lula Rd, Reagan, TN 38368

  Discover the perfect place to build your dream home on this beautiful 15.71-acre tract located on Old Lula Road. Offering approximately 745 feet of road frontage, this property provides privacy, space, and endless possibilities. A driveway has already been cleared, leading to a spacious 100' x 100' homesite, giving the future owner a head start on construction. The property features a beautiful

  Jennifer Scott RE/MAX Realty Source

  0 Old Lula Rd, Reagan, TN 38368
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  /7

  $1,700,000

  • Land
  • 112 Acres
  • $15,179 per Acre

  1120 Pleasant Ridge Rd, Finger, TN 38334

  Barry Smith Crye-Leike Elite

  1120 Pleasant Ridge Rd, Finger, TN 38334
• 

  

  /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
• 

  

  /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
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  /4

  $125,000

  • 3 Beds
  • 2 Baths

  553 Galbraith Ave, Henderson, TN 38340

  Property is being sold in an as-is condition, and the condition is unknown and may include defects, possible health or safety hazards, or debris, or be located in a Special Flood Hazard Area. Proof of Funds Required. The seller requires that the high bidder be able to demonstrate proof of funds or financing pre-qualification within 24 hours of the auction. Buyer must obtain a pre-qualification

  JERRY EMERSON KING Williams & Williams Real Estate Auctions

  553 Galbraith Ave, Henderson, TN 38340
• 

  

  /17

  $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

  0 Hill Ave, Henderson, TN 38340
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  /60

  $388,900

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

  450 North Ave, Henderson, TN 38340

  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 extended family? The upstairs apartment offers its own private entrance along with a kitchen, living room, bedroom,

  

  Destiny Burns

  Stellar Realty Group

  450 North Ave, Henderson, TN 38340
• 

  

  /27

  $285,000

  • 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. Home Selling "AS IS". 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. Backyard has organic compost for a beautiful garden.

  Jodie Parrish RE/MAX Realty Source

  2985 Sand Mountain Rd, Enville, TN 38332
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  /24

  $250,000

  • 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
• 

  /2

  $37,500

  • Land
  • 0 Sq Ft

  00 Barham Ave, Henderson, TN 38340

  Great lot to build your dream home in Chester County. Great schools and family friendly community. Call Melanie at 731.879.9655

  

  Melanie Malone

  Crye-Leike Elite

  00 Barham Ave, Henderson, TN 38340
• 

  

  /16

  $159,900

  • 3 Beds
  • 2 Baths
  • 1,116 Sq Ft

  730 Old Montezuma Rd, Henderson, TN 38340

  Charming 3-bedroom, 2-bath home offering 1116 sq ft of living space located within the city limits of Chester County, TN. This property is a great opportunity for investors or first-time home buyers looking for an affordable home with potential. Conveniently situated near West Chester School, the home offers easy access to local amenities, schools, and town conveniences. With a functional layout

  Aaliyah Cupples Stellar Realty Group

  730 Old Montezuma Rd, Henderson, TN 38340
• 

  

  /18

  $149,900

  • 3 Beds
  • 1 Bath
  • 1,014 Sq Ft

  334 Baughn St, Henderson, TN 38340

  Zach Hannis Casey Realtors

  334 Baughn St, Henderson, TN 38340
• 

  

  /46

  $349,900

  • 2 Beds
  • 1.5 Baths
  • 1,360 Sq Ft

  1380 Harrison Rd, Pinson, TN 38366

  Welcome to 1380 Harrison Ln, Pinson, TN — a rare opportunity to own a private retreat in one of West Tennessee's most exclusive gated communities. Located in Deanburg Hills HOA, this unique property offers more than just a home — it offers access to an incredible lifestyle with 480 private acres, a 20-acre lake, and recreation opportunities that are nearly impossible to find. With only 16 parcels

  

  Dylan Jones

  Southern LifeStyle Properties

  1380 Harrison Rd, Pinson, TN 38366
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  /49

  $550,000

  • 3 Beds
  • 2 Baths
  • 2,609 Sq Ft

  100 Valleyview Dr, Henderson, TN 38340

  BEAUTIFUL HOME LOCATED IN AN ESTABLISHED NEIGHBORHOOD, SO MUCH TO OFFER TO YOU AND YOUR FAMILY, BRICK HOME WITH 3 BR., 2 BATHS, PLUS BONUS ROOM OR 4TH BEDROOM ON UPPER LEVEL) GREAT LIVING ROOM W/FIREPLACE, FORMAL DINING ROOM, FANTASTIC KITCHEN W/ISLAND, PLUS A LARGE BREAKFAST NOOK, OVERLOOKING THE BACK YARD THAT HAS AN IN-GROUND POOL (CHLORINE) WITH A GAZEBO LOCATED AT THE FAR END OF POOL , PLUS

  Linda Carter Casey Realtors

  100 Valleyview Dr, Henderson, TN 38340
• 

  

  /25

  $200,000

  • Land
  • 65.9 Acres
  • $3,035 per Acre

  0 Plainview Rd, Henderson, TN 38340

  Discover your own private retreat on this secluded 65+ acre rural paradise. Featuring pristine woodlands and the peaceful flow of Jacks Creek winding through the property, this untouched land offers a rare opportunity to embrace nature at its finest. Ideal for off-grid living, recreation, hunting, or creating a one-of-a-kind private estate, the possibilities are endless. Escape the noise and

  Christy Fullington Crye-Leike Elite

  0 Plainview Rd, Henderson, TN 38340
• 

  

  /31

  $219,900

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft

  248 E 3rd St, Henderson, TN 38340

  Currently a duplex with a 1 BR 1BA unit and a 2BR 1BA unit, (separated by a breezeway), Just remodeled and freshened up with new paint, new floor covering throughout 2BR unit and new paint and new floor covering through most of 1 BR unit. Seller to installed a new Stove and Refrigerator & Dishwasher in both units before closing. ' ALL NEW WINDOWS IN BOTH UNITS. Could be turned into home with

  Linda Carter Casey Realtors

  248 E 3rd St, Henderson, TN 38340
• 

  

  /25

  $200,000

  • Land
  • 65.9 Acres
  • $3,035 per Acre

  2800 Plainview Rd, Henderson, TN 38340

  Discover your own private retreat on this secluded 65+ acre rural paradise. Featuring pristine woodlands and the peaceful flow of Jacks Creek winding through the property, this untouched land offers a rare opportunity to embrace nature at its finest. Ideal for off-grid living, recreation, hunting, or creating a one-of-a-kind private estate, the possibilities are endless. Escape the noise and

  Kenneth Fullington Crye-Leike Elite Realtors

  2800 Plainview Rd, Henderson, TN 38340
• 

  

  /16

  $209,900

  • 3 Beds
  • 1 Bath
  • 1,272 Sq Ft

  454 White Ave, Henderson, TN 38340

  Adorable 3 br Brick home sitting on large city lot with lots of character, Built ins and Mantle in living room, Hardwood floors throughout, Newly remodeled Kitchen with all new appliances, cabinets, laminate flooring and a Bar. Master has 2 large closets. Home has newer windows, metal roof, outbuilding for storage, new landscaping and a concrete driveway. Only a few blocks from Freed Hardeman

  Tammi McCall United Country - Columbia Realty & Auction

  454 White Ave, Henderson, TN 38340
• 

  

  /13

  $348,000

  • 3 Beds
  • 2 Baths
  • 1,985 Sq Ft

  521 Crook Ave, Henderson, TN 38340

  ENJOY THE COMFORT OF A PEACEFUL NEIGHBORHOOD WHILE HAVING PLENTY OF ROOM TO GROW. PROPERTIES WITH THIS MUCH POTENTIAL AND OUTDOOR SPACE ARE HARD TO FIND! BEAUTIFUL BRICK, 3 BEDROOM, 2 BATH HOME IN A HIGHLY DESIRABLE NEIGHBORHOOD! FEATURES INCLUDE: NEARLY 1/2 ACRE LOT W/FENCED IN BACK YARD, NEW METAL ROOF, DOUBLE CARPORT W/ATTACHED SHOP/WORKSHOP, TWO ATTICS FOR EXCEPTIONAL STORAGE (1 FLOORED IN

  Linda Carter Casey Realtors

  521 Crook Ave, Henderson, TN 38340
• 

  

  /27

  $364,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,950 Sq Ft

  359 Meadow Brook Dr, Henderson, TN 38340

  PRICE IMPROVEMENT! Now offered at $364,900 with the seller offering $5,000 in buyer concessions! Welcome to 359 Meadowbrook Drive, a beautiful brick home located on a quiet cul-de-sac in Henderson's highly desirable Meadowbrook subdivision. Featuring 3 bedrooms, 2 full bathrooms, and a desirable split-bedroom floor plan, this home offers comfort, privacy, and space for everyday living. The

  Alexander Verduzco RE/MAX Realty Source

  359 Meadow Brook Dr, Henderson, TN 38340
• 

  

  /7

  $119,900

  • Land
  • 29.86 Acres
  • $4,015 per Acre

  000 Cagle Trail, Henderson, TN 38340

  This 29.86-acre parcel sits beside Chickasaw State Park, offering a private, secluded retreat ideal for hunting, recreation, or a nature-rich residence. It features abundant wildlife, including deer and turkey, and provides ample privacy while showcasing everything nature has to offer.

  Zach Hannis Casey Realtors

  000 Cagle Trail, Henderson, TN 38340
• 

  

  /31

  $225,000

  $40K PRICE DROP

  • 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 Coldwell Banker Southern Realty

  5195 Tennessee 200, Henderson, TN 38340
• 

  

  /72

  $834,900

  • 6 Beds
  • 5 Baths
  • 4,772 Sq Ft

  746 Oneal Ln, Henderson, TN 38340

  Okay, friend... this one is special. With 6 bedrooms, 3 full baths, and 2 half baths, there's room here for just about everyone. The main floor offers an open-concept layout with 4 bedrooms and 2.5 baths, making everyday living easy and comfortable. But wait until you see what's upstairs. The sellers recently finished and expanded the space beyond the rec room, adding 2 additional bedrooms, a

  

  Destiny Burns

  Stellar Realty Group

  746 Oneal Ln, Henderson, TN 38340
• 

  

  /37

  $279,900

  • 3 Beds
  • 2.5 Baths
  • 1,928 Sq Ft

  255 Mitchell Ln, Henderson, TN 38340

  Looking for a great home right outside city limits . Then this could be the right home for you. This pretty home is sitting on a great corner lot and has so much to offer. The inside of this home has 3 br., office or nursery, 2.5 baths, large eat in kitchen, large master closet which contains the washer and dryer, plus an internal storm shelter right beside the closet/laundry. Outside has 2

  Linda Carter Casey Realtors

  255 Mitchell Ln, Henderson, TN 38340
• 

  

  /18

  $179,950

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  478 Woods Dr, Henderson, TN 38340

  3BR 1 BA home in city limits of Henderson, TN . Home just freshened up. New windows installed, new floor covering through out, and new exterior vinyl installed. Great rental or starter home. Closing on home to take place after January 1, 2027 and before February 1, 2027. Potential buyer will need to provide a preapproval letter when contract is written, but they will need to rent the property

  Linda Carter Casey Realtors

  478 Woods Dr, Henderson, TN 38340
• 

  

  /18

  $131,100

  • Land
  • 57 Acres
  • $2,300 per Acre

  2424 Grooms Rd Unit PT-12, 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 tract

  Austin Carroll Tutt Land Company

  2424 Grooms Rd Unit PT-12, Henderson, TN 38340
• 

  

  /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
• 

  

  /16

  $148,500

  • Land
  • 66 Acres
  • $2,250 per Acre

  2500 Grooms Rd Unit PT-11, 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 14-year-old

  Austin Carroll Tutt Land Company

  2500 Grooms Rd Unit PT-11, Henderson, TN 38340
• 

  

  /31

  $424,000

  • Land
  • 105 Acres
  • $4,038 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
• 

  

  /37

  $389,923

  $60K PRICE DROP

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

  1155 Ludell Ross Rd, Enville, TN 38332

  $70,000 BELOW RECENT APPRAISAL!! EAGER TO SELL!! MOTIVATED SELLERS!! BRING ALL OFFERS!! Recently appraised at $460,000 and now offered at just $389,923. Sellers are relocating and ready for their next chapter, creating an incredible opportunity to own a one-of-a-kind custom home on 5.21 acres at a price well below appraised value. This private, custom, one-of-a-kind home built in 2025 and sitting

  Jennifer Scott RE/MAX Realty Source

  1155 Ludell Ross Rd, Enville, TN 38332
• 

  

  /29

  $129,900

  • 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
• 

  

  /27

  $196,000

  • Land
  • 56 Acres
  • $3,500 per Acre

  2700 Bear Creek Rd, Pinson, TN 38366

  Situated on Bear Creek Road in northwest Chester County, this impressive 56-acre tract offers an excellent blend of natural beauty, recreational appeal, and future homesite potential. The property features gently rolling topography with approximately 800 feet of county road frontage, providing easy access and multiple attractive locations for building a cabin, weekend retreat, or full-time

  Cameron Isbell Mossy Oak Properties Southeast Land & Wildlife LLC

  2700 Bear Creek Rd, Pinson, TN 38366
• 

  

  /19

  $199,500

  • Land
  • 57 Acres
  • $3,500 per Acre

  2700 Bear Creek Rd, Pinson, TN 38366

  Located on Bear Creek Road in northwest Chester County, this exceptional 57-acre property offers a beautiful combination of gently rolling terrain, privacy, and recreational opportunity. Conveniently situated just a short drive from Jackson and Henderson, the tract features approximately 800 feet of county road frontage with several excellent potential homesites.The property is well

  Cameron Isbell Mossy Oak Properties Southeast Land & Wildlife LLC

  2700 Bear Creek Rd, Pinson, TN 38366

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