Chester County TN Homes for Sale

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  /45

  $590,000

  • 4 Beds
  • 3 Baths
  • 2,673 Sq Ft

  95 Teague Trace Ln, Luray, TN 38352

  Are you looking for a beautiful home with room to roam? Come take a look at 95 Teague Trace. This lovely, four bedroom, three bath brick home nestled on five open acres adorned with mature, majestic oak trees. This exceptional property offers the perfect blend of luxury, comfort, and privacy in a quiet, highly sought-after neighborhood. Inside you'll find spacious living areas featuring elegant

  Jennifer Maness-Scott Stellar Realty Group

  95 Teague Trace Ln, Luray, TN 38352
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  /28

  $545,900

  • 4 Beds
  • 3 Baths
  • 3,316 Sq Ft

  515 Ridgewood Dr, Henderson, TN 38340

  Spacious 4-5 Bedroom Home on Over an Acre in a Peaceful Country Setting - County Taxes Only!Welcome to this beautiful and versatile 4-bedroom, 3-bath home nestled on just over an acre in a sought-after neighborhood. Enjoy the best of both worlds — country tranquility just minutes from town!Inside, you'll find a smart layout with 2 bedrooms conveniently located downstairs, and 2

  Brandi Ragan Ragan Realty Group

  515 Ridgewood Dr, Henderson, TN 38340
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  /53

  $359,900

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

  170 Tall Pines Rd, Henderson, TN 38340

  LOVELY BRICK HOME WITH 3 BEDROOMS, 2.5 BATHS LOCATED IN A FANTASTIC NEIGHBORHOOD. THE MASTER BATH HAS A WHIRLPOOL TUB, SEPARATE SHOWER, DOUBLE VANITIES, BEDROOM 2 AND 3 HAS A JACK AND JILL BATHROOM, BEAUTIFUL DINING ROOM, ALSO A GREAT BREAKFAST NOOK, KITCHEN HAS QUARTZ COUNTER TOPS, THIS HOME HAS A LARGE BACK FENCED IN-YARD, LARGE PATIO WITH AN OUTSIDE GRILL, STORAGE BUILDING OUTSIDE FENCED IN

  Linda Carter Casey Realtors

  170 Tall Pines Rd, Henderson, TN 38340
• 

  

  

  /31

  $330,000

  • 3 Beds
  • 2 Baths
  • 2,059 Sq Ft

  836 Hill Ave, Henderson, TN 38340

  FANTASTIC BRICK HOME IN AN EXCELLENT LOCATION JUST WAITING ON ITS NEW FAMILY, 3 BR., 2 BATHS, FORMAL DINING ROOM, LARGE GARAGE, LOTS OF BEAUTIFUL FLOWER BEDS, LARGE DECK AND GREAT BACK FENCED IN YARD

  Linda Carter Casey Realtors

  836 Hill Ave, Henderson, TN 38340
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  /37

  $374,900

  • 4 Beds
  • 2 Baths
  • 2,728 Sq Ft

  815 Trice Rd, Henderson, TN 38340

  Welcome to 815 Trice Road—where modern updates meet classic comfort on just over 1.5 acres in Henderson, TN. With three bedrooms and two bonus rooms (or four bedrooms and a bonus—buyer's choice!), this flexible floor plan adapts to your lifestyle with ease. Every inch of this home has been thoughtfully updated with designer-inspired finishes that could rival any HGTV reveal. From the fresh

  Julie Holt Blue Suede Realty

  815 Trice Rd, Henderson, TN 38340
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  /58

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft

  115 Harmony Ln, Henderson, TN 38340

  Come and explore this stunning 3-bedroom, 2-bath brick home that boasts an array of attractive features. Enjoy a covered outdoor kitchen area, a cozy fire pit, and a fenced-in backyard—perfect for gatherings or relaxation. The interior is immaculate, so clean you could eat off the floors! Additionally, there's a fantastic workshop complete with a dedicated workout space, and even a charming she

  Craig Casey Casey Realtors

  115 Harmony Ln, Henderson, TN 38340
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  /13

  $349,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  2070 Talley Store Rd, Henderson, TN 38340

  72-Hour FIRST RIGHT OF REFUSAL in place.Welcome to 2070 Talley Store Rd - a brand new, beautifully built 3-bedroom, 2-bathroom brick home located just outside the city limits of Henderson, TN. This 1,800 sq ft home offers modern comfort and quality craftsmanship, featuring a spacious two-car garage, concrete driveway, and a covered back patio perfect for relaxing or entertaining. Nestled

  Brent West Crye-Leike Elite

  2070 Talley Store Rd, Henderson, TN 38340
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  /28

  $269,900

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft

  560 Ollie Ln, Henderson, TN 38340

  Take a look at this 3-bedroom, 2-bath vinyl siding home just minutes from town in a great location. This home offers convenience along with recent updates that make it move-in ready.The large living room features luxury vinyl plank flooring and plenty of space for relaxing or entertaining. The kitchen is beautiful with custom cabinets, tile flooring, and brand-new stainless appliances,

  Richard Emison NextHome 383 Real Estate

  560 Ollie Ln, Henderson, TN 38340
• 

  

  /22

  $219,900

  • 3 Beds
  • 2 Baths
  • 2,366 Sq Ft

  129 N Carolina Ave, Henderson, TN 38340

  Charming Move-In Ready Home Near Freed-Hardeman University! 129 North Carolina Ave, Henderson, TNWelcome to this beautifully updated single-family home located just minutes from Freed-Hardeman University and historic downtown Henderson. Whether you're a first-time homebuyer, an investor looking for strong rental potential, or someone seeking extra space without breaking the bank—this

  Billy Cromwell EXIT Realty Blues City

  129 N Carolina Ave, Henderson, TN 38340
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  /18

  $259,000

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

  135 W Third St, Henderson, TN 38340

  BUYERS! SELLER WILL PAY $5,000 TOWARDS CLOSING! 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

  Ashton Roberts Molly Moore Realty

  135 W Third St, Henderson, TN 38340
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  /21

  $455,000

  000 Stewart Cemetery Ln, Enville, TN 38332

  Immerse yourself in the epitome of rural sophistication at this captivating farm. Featuring a harmonious blend of wooded timber, expansive pasture land, and an abundance of wildlife, this property exudes unparalleled natural beauty. A meandering creek traverses the landscape, adding a touch of tranquility to the surroundings. With essential amenities such as a well, septic tank, and electricity

  Larry Roberts Casey Realtors

  000 Stewart Cemetery Ln, Enville, TN 38332
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  /25

  $279,000

  • 3 Beds
  • 2 Baths
  • 1,697 Sq Ft

  263 North Ave, Henderson, TN 38340

  Welcome to this beautifully remodeled 3 bedroom, 2 bath brick home located in a highly desirable area just minutes from FHU, schools, and shopping. The home has been thoughtfully updated with both style and comfort in mind, making it move-in ready for its next owner. Step inside to find a spacious living room featuring luxury vinyl plank flooring and a cozy fireplace, perfect for gatherings or

  Richard Emison NextHome 383 Real Estate

  263 North Ave, Henderson, TN 38340
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  /18

  $184,900

  • 3 Beds
  • 2 Baths
  • 1,066 Sq Ft

  543 Anderson Cir, Henderson, TN 38340

  Check out this lovely 3 bedroom, 2 bath home located in Henderson, TN. Sitting just inside the city limits, this property offers the convenience of being close to schools, shopping, and a variety of eating establishments, all while giving you that country feel. You'll love having your own shop for all your projects! Come by, step inside, picture yourself living here and see how this could be YOUR

  Jennifer Maness-Scott Stellar Realty Group

  543 Anderson Cir, Henderson, TN 38340
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  /6

  $35,000

  • Land
  • 0.52 Acre
  • $67,308 per Acre

  6530 Main St, Enville, TN 38332

  Unique Investment Opportunity - .52 Acre lot with former church building, being sold As-Is.Situated on a .52 acre lot, this property offers endless potential for investors or visionaries looking for a project. Currently featuring an uninhabitable church building, the structure provides a blank canvas for restoration, repurposing, or redevelopment. The lot is level with a slope in the back,

  Charissa Paniuski EXIT Realty Blues City

  6530 Main St, Enville, TN 38332
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  /32

  $499,900

  0 Old Cave Springs Rd, Henderson, TN 38340

  246 acres of opportunity approximately 15 minutes from the city limits of Henderson. Offers privacy, abundant wildlife and endless possibilities. Perfect for hunting, building or creating your own country retreat. Don't miss this opportunity.

  Tiffany Elder Porchlight Realty West TN

  0 Old Cave Springs Rd, Henderson, TN 38340
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  /14

  $163,000

  • Land
  • 45.31 Acres
  • $3,597 per Acre

  0 Tucker Rd, Henderson, TN 38340

  Discover 50 acres of beautiful Tennessee countryside, perfect for creating your own mini farm or building the permanent home you've always dreamed of. This private setting offers the peace and quiet you've been searching for, surrounded by nature and open space. Whether you're looking for a homestead, recreational retreat, or a serene place to put down roots, this property delivers the best of

  Lori Yarbro Evans Real Estate

  0 Tucker Rd, Henderson, TN 38340
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  /64

  $850,000

  • 1,600 Sq Ft

  115 Chalet Ln, Henderson, TN 38340

  Secluded retreat featuring 7 charming cabins on 12.81 acres in a gated community with a private drive leading to all cabins. Currently operated as a 55+ community, 5 of the cabins are rented, offering excellent income potential. The main cabin is a spacious 2-bedroom, 3-bath home with 1,600 sq. ft. and is occupied by the owner. Five cabins are 2-bedroom, 1-bath units with 768 sq. ft. each, and

  Lori Yarbro Evans Real Estate

  115 Chalet Ln, Henderson, TN 38340
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  /40

  $799,900

  • 6 Beds
  • 5 Baths
  • 5,000+ Sq Ft

  165 Tennessee 201, Reagan, TN 38368

  CHECK OUT this gorgeous country property with beautiful rolling hills loaded with great timber and open land that offers a great place for the outdoorsmen to the avid entertainer! The primary house was built in 1990 and is around 5,000 SF heated and cooled space with 3 garage bays. This home is SO spacious; it features 6 bedrooms, 5 bathrooms and great spaces for entertaining friends and family!

  Bret Carroll Coldwell Banker Southern R/E

  165 Tennessee 201, Reagan, TN 38368
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  /9

  $39,500

  • Land
  • 7.44 Acres
  • $5,309 per Acre

  000 Stewart Rd, Henderson, TN 38340

  7.44 serene, wooded acres in Chester County offer endless possibilities for unrestricted living. Create your dream retreat in this peaceful rural setting, where the blank canvas allows you to design and build as you please. Embrace the tranquility of country living on this spacious parcel of land. 7.44 acres of beautiful rural wooded land in Chester County offering endless possibilities for

  Larry Roberts Casey Realtors

  000 Stewart Rd, Henderson, TN 38340
• 

  

  /22

  $249,900

  • 4 Beds
  • 2 Baths
  • 1,509 Sq Ft

  110 Guy McAdams Rd, Henderson, TN 38340

  Welcome to your peaceful retreat in Henderson, Tennessee! This charming 4-bedroom, 2-bath home sits on a spacious 1.2-acre lot, offering the perfect blend of privacy and convenience. Step inside to find a warm, inviting layout with generous living space, a functional kitchen, and natural light throughout. The primary suite offers comfort and privacy, while three additional bedrooms provide plenty

  Hunter Ross Blue Suede Realty

  110 Guy McAdams Rd, Henderson, TN 38340
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  /7

  $30,000

  • Land
  • 2 Acres
  • $15,000 per Acre

  1575 Hurst Rd, Henderson, TN 38340

  Enjoy country living on this 2 acre lot, only 20 minutes from town of Henderson. Unlimited potential awaits you at this property!

  Linda Carter Casey Realtors

  1575 Hurst Rd, Henderson, TN 38340
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  /3

  $260,000

  • Land
  • 2.7 Acres
  • $96,296 per Acre

  00 Highway 45 S, Henderson, TN 38340

  Excellent location with high traffic count. Close proximity to Jackson & Henderson. Property is ready to build on. Owner is open to financing.

  Craig Casey Casey Realtors

  00 Highway 45 S, Henderson, TN 38340
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  /24

  $799,000

  • 5 Beds
  • 4.5 Baths
  • 4,280 Sq Ft

  715 Roundtree Ln, Beech Bluff, TN 38313

  This beautiful home features 5 bedrooms, 4 1/2 baths, wrap around porch, 9 ft ceilings on main level.... 13 + or - park like acres, 2 acre stocked pond... Koi pond and firepit in backyard...this fabulous home features 3 stories, full basement with bedroom, bath, den and office space....main floor features large eat-n-kitchen, formal dining, large greatroom with fireplace, built in bookcases and

  Joyce Addison Coldwell Banker Southern Realty

  715 Roundtree Ln, Beech Bluff, TN 38313
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  /4

  $48,000

  • Land
  • 5.2 Acres
  • $9,231 per Acre

  00 Lofton Rd, Enville, TN 38332

  Analytical: Unveiling 5.25 acres of unrestricted land in Enville, TN, this property is tailored for off the grid living. The front portion boasts a flat and clear terrain, while the back section is densely wooded. This juxtaposition of open space and seclusion creates a harmonious blend of possibilities for the prospective buyer seeking a versatile setting. Explore the untapped potential

  Larry Roberts Casey Realtors

  00 Lofton Rd, Enville, TN 38332
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  /5

  $34,900

  • Land
  • 1.3 Acres
  • $26,846 per Acre

  Lot 21 Timberwood Cove, Henderson, TN 38340

  Exclusive 1.3-acre lot in a stunning subdivision with restricted covenants, offering a serene and mature environment. Enjoy the benefits of county taxes while building your dream home in this sought-after location. Don't miss this rare opportunity to own a piece of land in this prestigious community. Situated within a prestigious and coveted exclusive subdivision, this 1.3-acre property adheres

  Zach Hannis Casey Realtors

  Lot 21 Timberwood Cove, Henderson, TN 38340
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  /4

  $129,000

  • Land
  • 19.88 Acres
  • $6,489 per Acre

  000 Highway 22 A, Enville, TN 38332

  Escape to Tennessee Country Living on this 19.88-acre parcel situated in Enville, TN. Ideally located just 20 miles from Lexington, Henderson, and Savannah, TN, this property offers no restrictions and lies outside city limits, giving you the perfect chance to make your dreams come true.

  Lori Yarbro Evans Real Estate

  000 Highway 22 A, Enville, TN 38332
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  /7

  $58,500

  • Land
  • 8.99 Acres
  • $6,507 per Acre

  0 Highway 22 A, Enville, TN 38332

  Escape to Tennessee Country Living on this 8.99-acre parcel situated in Enville, TN. Ideally located just 20 miles from Lexington, Henderson, and Savannah, TN, this property offers no restrictions and lies outside city limits, giving you the perfect chance to make your dreams come true.

  Lori Yarbro Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
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  /28

  $295,000

  • 3 Beds
  • 3 Baths
  • 2,312 Sq Ft

  511 White Ave, Henderson, TN 38340

  Take a look at this nicely remodeled 3-bedroom, 3-bath stone exterior home in a great location. Within walking distance to Freed-Hardeman University, schools, and shopping, this home offers both convenience and comfort.Inside, the home features beautiful restored hardwood floors that bring out its original charm. The master bedroom includes an adjoining bath, and the large secondary

  Richard Emison NextHome 383 Real Estate

  511 White Ave, Henderson, TN 38340
• 

  

  /17

  $218,500

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  5060 Enville Rd, Henderson, TN 38340

  MOTIVATED SELLERS! Home comes with a Home Warranty! Welcome to 5060 Enville Rd. Henderson, TN. This charming 3bed 2bath farmhouse seamlessly blends comfort with rustic appeal. This home highlights a huge master bedroom perfect for your retreat after a busy day, a brand new roof that ensures years of worry-free living, 2 acres of beautiful landscape, a poultry coop and a workshop with

  Braden Mileham Blue Suede Realty

  5060 Enville Rd, Henderson, TN 38340
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  /66

  $525,000

  • 4 Beds
  • 2 Baths
  • 2,744 Sq Ft

  320 Rabbit Ranch Rd, Henderson, TN 38340

  Welcome to your private retreat—this charming 4-bedroom, 2-bath brick home is nestled on a sprawling 57-acre estate offering a rare combination of space, seclusion, and opportunity. Whether you’re looking for a forever home, hobby farm, or hunter’s paradise, this property delivers.Step inside to find a warm and inviting interior with spacious living areas, a functional kitchen, and a cozy

  ERICA MAXWELL Tiffany Jones Realty Group, LLC

  320 Rabbit Ranch Rd, Henderson, TN 38340
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  /29

  $249,900

  • 3 Beds
  • 1.5 Baths
  • 1,645 Sq Ft

  1140 Plainview Rd, Henderson, TN 38340

  Move-In Ready Brick Home on Peaceful 1.92 Acres - No Restrictions!Don't miss this opportunity to own a well-maintained 3-bedroom, 1.5-bath brick home perfectly situated on a spacious 2-acre corner lot. With no restrictions and only one nearby neighbor, enjoy privacy, freedom, and room to grow.This home features a bright and functional layout, a great yard ideal for relaxing,

  Dustin Insell Coldwell Banker Southern Realty

  1140 Plainview Rd, Henderson, TN 38340
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  /8

  $100,000

  • Land
  • 22.83 Acres
  • $4,380 per Acre

  0 Old Lula Rd, Reagan, TN 38368

  Discover over 22 acres of secluded, wooded, paradise with paved road frontage. A rare combination of convenience and privacy. This property is ideal for a weekend hunting retreat, recreational escape. or the perfect spot to build your dream home in the heart of nature.

  Erica Maxwell Tiffany Jones Realty Group

  0 Old Lula Rd, Reagan, TN 38368
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  /15

  $90,000

  • 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
• 

  

  /23

  $269,000

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  533 North Ave, Henderson, TN 38340

  Discover this stunning, completely remodeled 4-bedroom, 2.5-bath home featuring a spacious 2-car garage. Every detail has been thoughtfully updated, including brand-new cabinets, flooring, and lighting fixtures, creating a fresh and modern living space. The HVAC system has been replaced for optimal comfort year-round.Enjoy the beautifully landscaped yard—perfect for outdoor gatherings,

  Zach Hannis Casey Realtors

  533 North Ave, Henderson, TN 38340
• 

  

  /26

  $256,000

  • 5 Beds
  • 3 Baths
  • 2,200 Sq Ft

  467 White Ave, Henderson, TN 38340

  Looking for a beautiful home in town with a lot of space, within walking distance to downtown, churches and FHU. Ask about the Renovations done in the Summer of 2022, 5 bedrooms, 3 baths, formal dining room, Large Living room, Covered Back Porch Garage has an area for a one bedroom in garage. this area is heated and cooled but no bathroom

  Linda Carter Casey Realtors

  467 White Ave, Henderson, TN 38340
• 

  

  /10

  $199,500

  • 5 Beds
  • 2 Baths
  • 1,917 Sq Ft

  325 Jennings Rd, Reagan, TN 38368

  Good area in rural area. NEW septic system just installed. New flooring installed of both carpet and lvp. House is empty and ready for the new owners.

  Craig Casey Casey Realtors

  325 Jennings Rd, Reagan, TN 38368
• 

  

  /20

  $289,900

  • 3 Beds
  • 2 Baths
  • 1,465 Sq Ft

  4745 Enville Rd, Henderson, TN 38340

  This Charming 2012 Build in Henderson, TN on 1.00+- Acres is Hitting the Market! This Home Was Remodeled in 2024 with New Roof, LVP Flooring, Custom Cabinetry with Stunning Countertops, Tiled Shower in Primary, Large Living Room Semi Open to Kitchen with Dining Area ; This Home HVAC Was Updated in 2025 with New Ductwork with Extra in Primary Bedroom, UV Lighting and Ozone Generator, Polarized

  Drake Harber Blue Suede Realty

  4745 Enville Rd, Henderson, TN 38340
• 

  

  /7

  $110,000

  • Land
  • 16 Acres
  • $6,875 per Acre

  0 Highway 22 A, Enville, TN 38332

  Escape to Tennessee Country Living on this 16.24 parcel situated in Enville, TN. Ideally located just 20 miles from Lexington, Henderson, and Savannah, TN, this property offers no restrictions and lies outside city limits, giving you the perfect chance to make your dreams come true. Part of tract has already been cleared and ready to build on.

  Lori Yarbro Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
• 

  

  /12

  $49,000

  • Land
  • 10.33 Acres
  • $4,743 per Acre

  0 Cash School Rd, Enville, TN 38332

  This unrestricted parcel offers solid ground and a full stand of 25 year old loblolly pine. Quiet area, easy access, and room to spread out. Great for a cabin, trailer, or future investment. Power at the road - bring your own water source. Owner financing available.

  Ronald (Ron) Daniel, II Daniel Auction & Real Estate, LLC

  0 Cash School Rd, Enville, TN 38332
• 

  

  /32

  $474,900

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

  137 Gibson Dr, Henderson, TN 38340

  Step into history with this exquisite Chester County landmark, built in 1952 and was once the home of Former Circuit Court Judge Willard E. Smith. This stunning home, a testament to timeless elegance, has been lovingly renovated to offer modern amenities while preserving its historic charm.Property Highlights:-Size: 2,650 sqft of meticulously renovated living space-Bedrooms: 4

  Brent West Crye-Leike Elite

  137 Gibson Dr, Henderson, TN 38340

Showing Results 41 - 80, Page 2 of 3