Chester County, TN Homes

• 

  

  

  /24

  $329,900 Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,949 Sq Ft

  164 Ben Cove, Henderson, TN 38340

  Welcome to 164 Ben Cove, a well kept 3 bedroom, 2 bath brick home nestled on a peaceful cul-de-sac in one of Henderson's most desirable neighborhoods. With just under 2,000 sq ft of space, this home offers a warm, comfortable layout, perfect for everyday living and entertaining. The main living area features hardwood floors and a spacious, open feel. You'll love the seamless flow from the living

  

  Jennifer Scott

  RE/MAX Realty Source

  (731) 236-2986

  164 Ben Cove, Henderson, TN 38340
• 

  

  

  /22

  $120,000 Sold Aug 15, 2025

  • 1,292 Sq Ft
  • $93/SF
  • 10 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1920

  419 White Ave, Henderson, TN 38340

  Beautifully Remodeled 2 Bedroom, 2 Bath Home in the Heart of HendersonWelcome to this charming and thoughtfully remodeled 2-bedroom, 2-bath home, perfect for comfortable living. Featuring spacious rooms and a large front porch, this residence offers both style and functionality.Located in the vibrant heart of Henderson, you'll enjoy easy access to Freed Hardeman University, shopping,

  Zach Hannis Casey Realtors

  419 White Ave, Henderson, TN 38340
• 

  

  

  /19

  Est $205,360 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft

  566 Todd Ray Cove, Henderson, TN 38340

  566 Todd Ray Cove, Henderson, TN 38340
• 

  

  

  /64

  $699,000

  • 3 Beds
  • 3.5 Baths
  • 4,108 Sq Ft

  325 Ridgewood Dr, Henderson, TN 38340

  Welcome to 325 Ridgewood Dr. in Creekside Estates! This custom-built home offers over 4,100 heated square feet with three bedrooms and two full baths on the main floor, all centered around an open floor plan.The fully finished basement includes an oversized one-car garage, game room, family room, full bath, extra room that could be used as a bedroom, and an extra-large safe

  

  Destiny Burns

  Stellar Realty Group

  (731) 389-9336

  325 Ridgewood Dr, Henderson, TN 38340
• 

  

  

  /40

  $303,000 Sold Aug 13, 2025

  • 2,000+ Sq Ft
  • $152/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1998

  860 Plainview Rd, Henderson, TN 38340

  Welcome to your slice of country paradise! Nestled on 4.1 acres, this charming 3-bedroom, 2-bath home offers space, comfort, and the perfect mix of relaxation and functionality. Enjoy summer days in the above-ground pool or unwind on the spacious back deck, which flows seamlessly from the living room—ideal for entertaining or peaceful evenings. A bonus sitting area adds extra space for gatherings

  Darby Drinkard Action Realty

  860 Plainview Rd, Henderson, TN 38340
• 

  

  /22

  Est $235,784 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,554 Sq Ft

  190 Shannon Dr, Henderson, TN 38340

  190 Shannon Dr, Henderson, TN 38340
• 

  

  /7

  $42,000

  • Land
  • 2.94 Acres
  • $14,286 per Acre

  Lot 22 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 22! This beautiful 2.94-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

  (731) 316-0342

  Lot 22 Greystone Cove, Henderson, TN 38340
• 

  

  /15

  $159,000 Sold Aug 11, 2025

  • 1,400+ Sq Ft
  • $114/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  1980 Sanford Rd, Henderson, TN 38340

  **New Price Alert**This unique gem sits just shy of an acre lot in Henderson, TN, offering peaceful country living and room to grow. The property features mature pecan, walnut, pear, apple, and fig trees—perfect for those who appreciate nature and space. Inside, you'll find original hardwood floors, a spacious layout, a large laundry room, and a custom walk-in closet designed by the owner. The

  Evett Furr D. C. A. Realty, LLC

  1980 Sanford Rd, Henderson, TN 38340
• 

  

  /19

  Est $166,482 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,162 Sq Ft

  1320 Parker Loop, Henderson, TN 38340

  1320 Parker Loop, Henderson, TN 38340
• 

  

  /8

  $42,000

  • Land
  • 3.77 Acres
  • $11,141 per Acre

  Lot 21 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 21! This beautiful 3.77-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

  (731) 257-2136

  Lot 21 Greystone Cove, Henderson, TN 38340
• 

  

  /70

  $525,000 Sold Aug 05, 2025

  • 2,927 Sq Ft
  • $179/SF
  • 6 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2001

  5755 Old Jacks Creek Rd, Henderson, TN 38340

  Discover your dream home in this stunning property featuring three spacious bedrooms and 2.5 baths. The finished rec room in the basement provides ample space for entertainment, while a dedicated office in the main house offers a perfect work-from-home setup. The detached garage is a standout, boasting a workroom and a full bath, plus a dedicated workshop for all your projects. Enjoy the

  Destiny Burns Stellar Realty Group

  5755 Old Jacks Creek Rd, Henderson, TN 38340
• 

  

  /22

  Est $249,997 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,730 Sq Ft

  Unlisted Address

  Unlisted Address
• 

  

  /5

  $42,000

  • Land
  • 2.27 Acres
  • $18,502 per Acre

  Lot 18 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 18! This beautiful 2.27-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

  (731) 257-2344

  Lot 18 Greystone Cove, Henderson, TN 38340
• 

  

  /95

  $1,195,000 Sold Aug 04, 2025

  • 3,090 Sq Ft
  • $387/SF
  • 113 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2014

  375 Glendale Rd, Henderson, TN 38340

  Welcome to 375 Glendale Road, also affectionately known as Pierce Point. You won't find a more beautiful, manicured or pristinely cared for property. Only five minutes and two turns from downtown, you will love this private, 40-acre retreat in Henderson, TN. With fenced, wooded and open land, the possibilities are endless. The custom-built main house boasts 5 bedrooms, 3 full baths and

  Tori Wilkerson Hickman Realty Group Inc.-Jack

  375 Glendale Rd, Henderson, TN 38340
• 

  

  /34

  Est $187,162 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,333 Sq Ft

  2215 State Route 22a S, Jacks Creek, TN 38347

  2215 State Route 22a S, Jacks Creek, TN 38347
• 

  

  /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

  (731) 330-8452

  Lot 8 Greystone Cove, Henderson, TN 38340
• 

  

  /14

  $47,000 Sold Jul 31, 2025

  • 822 Sq Ft
  • $57/SF
  • 1 Day On Market

  • 3 Beds
  • 1 Bath
  • Built 1957

  492 Anderson Cir, Henderson, TN 38340

  This home features fresh paint and brand new vinyl flooring, offering a clean, updated feel throughout. With 3 bedrooms and one bath, its a great opportunity to make it your own. Conveniently located close to town-call today to schedule your private showing.

  Jennifer Scott RE/MAX Realty Source

  492 Anderson Cir, Henderson, TN 38340
• 

  

  /18

  Est $162,541 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,552 Sq Ft

  503 Crook Ave, Henderson, TN 38340

  503 Crook Ave, Henderson, TN 38340
• 

  

  /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

  (731) 666-6365

  Lot 7 Greystone Cove, Henderson, TN 38340
• 

  

  /19

  $234,900 Sold Jul 30, 2025

  • 1,600 Sq Ft
  • $147/SF
  • 204 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2020

  2580 Rabbit Ranch Rd, Henderson, TN 38340

  Country living, peaceful, charming. This property has so many wonderful features and so many possibilities! The covered front porch is a great place to relax with a cup of coffee or after a long day at work. Enter the home and find a massive great room, with tons of cabinetry and recessed lighting. What an amazing place to host family and friend gatherings. The split floor plan creates

  Angie Morris Hickman Realty Group, Inc.-Mil

  2580 Rabbit Ranch Rd, Henderson, TN 38340
• 

  

  /20

  Est $199,646 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,216 Sq Ft

  412 Old Jackson Rd, Henderson, TN 38340

  412 Old Jackson Rd, Henderson, TN 38340
• 

  

  /7

  $42,000

  • Land
  • 1.61 Acres
  • $26,087 per Acre

  Lot 5 Greystone Cove, Henderson, TN 38340

  Greystone Estates presents Lot 5! 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

  (731) 327-6186

  Lot 5 Greystone Cove, Henderson, TN 38340
• 

  

  /29

  $160,000 Sold Jul 25, 2025

  • 1,150 Sq Ft
  • $139/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2007

  955 Leo Weaver Rd, Finger, TN 38334

  Extremely well-maintained three bedroom, two bath manufactured home. The home is nestled on 11 beautiful acres in Chester County! A 24x36 wired shop provides the perfect space for hobbies or storage. Enjoy the peace and privacy of country living with plenty of room to roam—don't miss this rare opportunity!

  Madison Balding Town and Country

  955 Leo Weaver Rd, Finger, TN 38334
• 

  

  /23

  Est $182,950 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,158 Sq Ft

  3090 Wilson School Rd, Henderson, TN 38340

  3090 Wilson School Rd, Henderson, TN 38340
• 

  

  /22

  $110,000

  • Land
  • 9 Acres
  • $12,543 per Acre

  0 Peddy Vestal Loop, Henderson, TN 38340

  Land for Sale! Don't miss this opportunity to own approximately 8.77 acres in a prime location to build your dream home! With no restrictions, the possibilities are endless—design, build, or create exactly what you've imagined. Conveniently zoned for East Chester Schools in Chester County, this property won't last long. Act fast and make it yours today!

  

  Destiny Burns

  Stellar Realty Group

  (731) 251-4562

  0 Peddy Vestal Loop, Henderson, TN 38340
• 

  

  /24

  $439,900 Sold Jul 25, 2025

  • 1,583 Sq Ft
  • $278/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2000

  2845 Sanford Rd, Henderson, TN 38340

  Charming 3-Bedroom Brick Home on 5+ Private Acres with Workshop & RV HookupsWelcome to your own peaceful retreat! Nestled on over 5 beautiful, tree-filled acres, this bright and inviting 3-bedroom, 2-bath brick home offers the perfect blend of privacy, functionality, and natural beauty. Mature trees surround the property, creating a serene, park-like setting ideal for relaxation or

  Jon Putt Putt Real Estate Advisors

  2845 Sanford Rd, Henderson, TN 38340
• 

  

  /17

  Est $242,987 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  385 Melodie Cir, Henderson, TN 38340

  385 Melodie Cir, Henderson, TN 38340
• 

  

  /65

  $499,900

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

  240 Greystone CV St, Henderson, TN 38340

  Beautiful custom brick home located in the serene Greystone Estates of Chester County! This property features 3 bedrooms, 2.5 baths, a spacious primary suite with a huge walk-in closet connected to the oversized laundry room, and a stunning 25x30 detached brick double garage. Nestled on nearly 8 acres, this home offers both space and privacy. Don't miss your chance to make it yours!

  

  Destiny Burns

  Stellar Realty Group

  (731) 260-2721

  240 Greystone CV St, Henderson, TN 38340
• 

  

  /19

  $199,900 Sold Jul 25, 2025

  • 1,196 Sq Ft
  • $167/SF
  • 281 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1976

  1040 Parker Loop, Henderson, TN 38340

  Convenient Country Living: 3 Bed, 2 Bath Brick Home. Discover the perfect blend of comfort and convenience in this 3-bedroom, 2-bath brick home, situated in a beautiful country setting. Just minutes from downtown Henderson Tn and Chickasaw State Park & Golf Course. County taxes only. Recent upgrades include fresh exterior paint, new roof May 2023, new windows Feb 2022. Spacious Master Suite with

  Richard Emison NextHome 383 Real Estate

  1040 Parker Loop, Henderson, TN 38340
• 

  

  /20

  Est $273,250 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,458 Sq Ft

  1070 Dennis Latham Rd, Beech Bluff, TN 38313

  1070 Dennis Latham Rd, Beech Bluff, TN 38313
• 

  

  /26

  $189,900

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

  1341 Old Jacks Creek Rd, Henderson, TN 38340

  Recently renovated farmhouse in Chester County on 1.46 acres! Many updates include newer metal roof, HVAC, updated kitchen and bathrooms. The open floorplan and spacious bedrooms offer natural lighting and provides function and relaxation throughout the home. The exterior includes an inviting covered front porch, circular driveway, separate storage shed along with a large concrete pad that would

  

  Ben Roberts

  RE/MAX Realty Source

  (731) 224-4313

  1341 Old Jacks Creek Rd, Henderson, TN 38340
• 

  

  /39

  $300,000 Sold Jul 22, 2025

  • 2,000+ Sq Ft
  • $150/SF
  • 36 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2013

  85 Neshova Ln, Henderson, TN 38340

  Step inside this move in ready home to an open floor plan with split bedrooms. Improvements to this home include: new HVAC, new LVP flooring, new well bladder, new moisture barrier under home, new water heater and fresh paint throughout the home. Included also are the refrigerator, washer, dryer, and playhouse pictured. Take advantage of county takes only, a generrous acre of land and fenced

  Jennifer Greer Greer Real Estate Group

  85 Neshova Ln, Henderson, TN 38340
• 

  

  /44

  Est $210,638 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  2055 New Friendship Rd, Beech Bluff, TN 38313

  2055 New Friendship Rd, Beech Bluff, TN 38313
• 

  

  /55

  $599,000

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

  165 Hunters Glen Ln, Henderson, TN 38340

  This immaculate custom-built home sits on approximately 2.76 beautiful acres in the effluent estates of Hunters Glen , offering the perfect blend of luxury, functionality, and privacy. From the moment you enter, you'll notice quality craftsmanship throughout—featuring soaring 11-foot ceilings, elegant crown molding, and fresh paint in every room.The home offers 3 spacious bedrooms, 2

  

  Destiny Burns

  Stellar Realty Group

  (731) 318-1604

  165 Hunters Glen Ln, Henderson, TN 38340
• 

  

  /52

  $210,000 Sold Jul 21, 2025

  • 2,265 Sq Ft
  • $93/SF

  • 4 Beds
  • 2 Baths
  • Built 1946

  325 Crook Ave, Henderson, TN 38340

  Beautiful home located in an excellent location, within walking distance FHU. Home has new roof, 2 new HVAC units, spacious living room, huge den, private patio, storm shelter in garage. Call today to set up a showing! Seller will pay for an inspection, SELLER WILL pay $10,000. toward buyer closing costs and prepaids

  Linda Carter Casey Realtors

  325 Crook Ave, Henderson, TN 38340
• 

  

  /22

  Est $180,505 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,085 Sq Ft

  2685 Wilson School Rd, Henderson, TN 38340

  2685 Wilson School Rd, Henderson, TN 38340
• 

  

  /49

  $541,800

  • Land
  • 252 Acres
  • $2,150 per Acre

  388 Old Cave Springs Rd, Henderson, TN 38340

  Welcome to a true outdoor haven tucked away in the heart of Chester County, TN. Spanning an impressive 252 acres, this property offers a diverse landscape with plantation pines, thinned timber, and areas of cutover, creating a dynamic mix of habitat. This combination is ideal for supporting the region's thriving wildlife population. Known for its trophy bucks and exceptional turkey hunting, this

  Annah Barnes

  SmallTown Hunting Properties & Real Estate

  (662) 316-3971

  388 Old Cave Springs Rd, Henderson, TN 38340
• 

  

  /31

  $235,000 Sold Jul 18, 2025

  • 1,148 Sq Ft
  • $205/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  235 Pinecrest Dr, Henderson, TN 38340

  This 3 bedroom 2 full bath home in the Sugar Creek subdivision is a must see! This home sits on an huge lot on a dead end street. Enjoy entertaining family and friends on the back covered patio. Plenty of room for outdoor activities in the fenced in backyard, but the property goes back even further. The front yard is just as big. This home also offers a front covered porch where you can sip

  Jessica Asberry EXIT Realty Blues City

  235 Pinecrest Dr, Henderson, TN 38340
• 

  

  /7

  Est $249,417 Not Listed For Sale

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

  795 Hill Ave, Henderson, TN 38340

  795 Hill Ave, Henderson, TN 38340
• 

  

  /59

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 3,050 Sq Ft

  70 Mosier Ln, Henderson, TN 38340

  NEW ROOF!!! UNDERGROUND PROPANE TAKE!!! WHOLE HOME GENERATOR!!! Expansive Country Estate with Modern Comforts and Premium Features Welcome to 70 Mosier Lane, a picturesque 18-acre estate in the serene countryside of Henderson, TN. Built in 2009, this 4-bedroom, 3-bathroom home offers the perfect blend of privacy, functionality, and high-end amenities—ideal for those seeking a self-sufficient

  

  Joshua Trammell

  EXIT Realty Blues City

  (731) 330-2283

  70 Mosier Ln, Henderson, TN 38340

Showing Results 41 - 80, Page 2 of 18