Chester, TN Homes

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  /74

  $975,000

  • 5 Beds
  • 4.5 Baths
  • 6,888 Sq Ft

  575 Homestead Ln, Henderson, TN 38340

  Custom build dream home w/well thought out upgrades on 3.11 acres. Brick 5BR/4.5BA with fully finished walk-out basement/in-law suite. Large Master Bedroom with 2 walk-in closets with heated whirlpool tub. Large 3 car garage with ample room. Small red barn for your lawn equipment and other outdoor items. State of the art recently upgraded 4k movie theater (8k capable), 100" sound perforated

  

  Jesse Bradley

  Tennessee Valley Realty and Investment Group, PLLC

  (731) 200-1270

  575 Homestead Ln, Henderson, TN 38340
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  /9

  $1,200 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Townhouse for Rent

  320 Samantha Cove, Henderson, TN 38340

  Property Id: 1355768Welcome to this charming 2 bedroom, 1 bathroom townhouse in Henderson, TN. Enjoy the convenience of included utilities and amenities such as refrigerator, oven, and dishwasher. With central air and forced air heating, this smoke-free property is perfect for a single unit. Don't miss out on this opportunity for a cozy home at $1200/month starting July 1, 2025. No pets

  320 Samantha Cove, Henderson, TN 38340
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  /11

  $145,000 Sold Aug 28, 2025

  • 1,146 Sq Ft
  • $127/SF
  • 95 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1981

  471 Woods Dr, Henderson, TN 38340

  Charming 3 bed, 1.75 (full bath in hallway, .75 bath in master containing a shower, sink and commode) bath home with a unique feature - an inside-access storm shelter located off the back left bedroom. Enjoy a small back deck perfect for relaxing. Located near Henderson with easy access to Jackson, this home is situated in a great neighborhood. Incorrect tax card. Please give tenant 24 hour

  Linda Carter Casey Realtors

  471 Woods Dr, Henderson, TN 38340
• 

  

  

  /35

  Est $240,634 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,436 Sq Ft

  1470 Sanford Rd, Henderson, TN 38340

  1470 Sanford Rd, 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
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  /34

  $260,000 Sold Aug 25, 2025

  • 3,240 Sq Ft
  • $80/SF
  • 73 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2007

  285 Mitchell Ln, Henderson, TN 38340

  Unique 2-story barndominium/shop awaiting your personal touch! Currently 2 bed 2 bath, but a blank canvas for your creativity. Features roll-up garage doors on both ends, kitchen with appliances, 2 bathrooms, one on each floor. Ground floor spans 2400 sq ft, while the upper level offers 1200 sq ft of potential. Enjoy a cupola with panoramic 360-degree views. Located just outside city limits, this

  Larry Roberts Casey Realtors

  285 Mitchell Ln, Henderson, TN 38340
• 

  

  /12

  Est $271,755 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,042 Sq Ft

  205 Cedar Brook Ln, Henderson, TN 38340

  205 Cedar Brook Ln, 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
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  /25

  $183,000 Sold Aug 22, 2025

  • 1,022 Sq Ft
  • $179/SF
  • 18 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1950

  6495 Tennessee 100, Henderson, TN 38340

  This charming one-level home sits on a full acre surrounded by scenic farmland. With 2 bedrooms and 2 full baths, the home offers a functional layout and easy living. Step onto the inviting front or side porch and take in the quiet views—perfect for morning coffee or evening unwinding. Inside, you'll find a spacious living area, a well-sized kitchen, and plenty of natural light. The property

  Amanda Harvey Coldwell Banker Southern Realty

  6495 Tennessee 100, Henderson, TN 38340
• 

  

  /20

  Est $243,895 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,409 Sq Ft

  60 Rushing Creek Ln, Henderson, TN 38340

  60 Rushing Creek Ln, Henderson, TN 38340
• 

  

  /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
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  /29

  $175,000 Sold Aug 20, 2025

  • 1,284 Sq Ft
  • $136/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1979

  948 Sand Ave, Henderson, TN 38340

  Charming 3-bedroom, 2-bathroom ranch-style home on a spacious city lot. This property features a screened porch at the front, a deck at the back with a retractable sunshade, and a small dog run in the backyard. Priced competitively for a quick sale, the home is conveniently located near Henderson and Jackson, making it ideal for both residential buyers and investors. Don't miss out on this

  Linda Carter Casey Realtors

  948 Sand Ave, Henderson, TN 38340
• 

  

  /15

  Est $272,458 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,981 Sq Ft

  740 Corson Rd, Henderson, TN 38340

  740 Corson Rd, Henderson, TN 38340
• 

  

  /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
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  /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
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  /33

  Est $226,808 Not Listed For Sale

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

  360 Jacks Creek St, Henderson, TN 38340

  360 Jacks Creek St, Henderson, TN 38340
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  /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
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  /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
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  /45

  Est $444,112 Not Listed For Sale

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

  215 Harris Ln, Henderson, TN 38340

  215 Harris Ln, Henderson, TN 38340
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  /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
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  /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
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  /24

  Est $477,070 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 4,239 Sq Ft

  6245 State Route 200, Henderson, TN 38340

  6245 State Route 200, 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
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  /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 $325,326 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,276 Sq Ft

  95 Village Way, Henderson, TN 38340

  95 Village Way, 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
• 

  

  /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
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  /29

  Est $210,641 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,527 Sq Ft

  333 Steed St, Henderson, TN 38340

  333 Steed St, Henderson, TN 38340
• 

  

  /26

  $194,900

  • 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
• 

  

  /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
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  /32

  Est $165,674 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,066 Sq Ft

  300 Proctor Rd, Henderson, TN 38340

  300 Proctor Rd, Henderson, TN 38340
• 

  

  /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
• 

  

  /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
• 

  

  /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
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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /22

  Est $249,997 Not Listed For Sale

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

  Unlisted Address

  Unlisted Address

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