Chester County TN Homes for Sale

• 

  

  

  /9

  $19,900

  • Land
  • 1 Acre
  • $19,900 per Acre

  285 Cedar Brook Ln, Henderson, TN 38340

  Build the home you've been dreaming of in beautiful Hidden Hills Estates! This 1-acre building lot offers the perfect setting for a basement home, with a gentle slope that creates ideal elevation and design opportunities. Tucked at the back of the property, Tar Creek runs behind the lot, adding a peaceful natural backdrop and enhancing the privacy this homesite provides. Wildlife is

  

  Brandi Wilson Isom

  RE/MAX Realty Source

  285 Cedar Brook Ln, Henderson, TN 38340
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  /13

  $225,550

  • Land
  • 45.11 Acres
  • $5,000 per Acre

  0 Highway 22 A, Enville, TN 38332

  Escape to Tennessee Country Living on this 45.11 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. Soil mapping has been done. Call today!

  

  Lori Yarbro

  Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
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  /82

  $574,900

  • 3 Beds
  • 2.5 Baths
  • 3,786 Sq Ft

  231 Mitchell St, Henderson, TN 38340

  Imagine starting your morning with a cup of coffee on the back patio, overlooking the beautiful flower gardens. This backyard is truly something special—you'll feel like you've been transported to the English countryside. Peaceful, picturesque, and full of charm, it's the perfect place to slow down and enjoy the beauty around you.

  

  Destiny Burns

  Stellar Realty Group

  231 Mitchell St, Henderson, TN 38340
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  /35

  $480,000

  • Land
  • 143.34 Acres
  • $3,349 per Acre

  0 Highway 22 A, Enville, TN 38332

  Don’t miss this rare opportunity to own 143.34 unrestricted acres in a fantastic location just off Hwy 22 in Enville, Tennessee. This versatile tract offers convenient access to Lexington, Henderson, and Adamsville while still providing the privacy, nature, and wide-open space buyers are looking for. With electricity available at the road and multiple ideal building sites, this property is

  

  Lori Yarbro

  Evans Real Estate

  0 Highway 22 A, Enville, TN 38332
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  /42

  $249,000

  • 2 Beds
  • 1 Bath
  • 1,279 Sq Ft

  470 North Ave, Henderson, TN 38340

  This Charming Cottage is perfect for those seeking a Home with a heart. This beautiful Home features vintage details throughout, a cozy fireplace, original hardwood, stone counters, spacious backyard, plenty of natural light, hydrangeas, large front porch, and all the attention to details that will make you feel like you are living in a storybook! If you are looking for a beautiful Home that

  

  Destiny Burns

  Stellar Realty Group

  470 North Ave, Henderson, TN 38340
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  /9

  $49,900

  $5K PRICE DROP

  • Land
  • 5.5 Acres
  • $9,073 per Acre

  00 Old State Highway 22a, Enville, TN 38332

  5.5 Acres of Wooded Land with Dual Road Frontage - Ready to Build in Enville, TN (Chester County) Discover your perfect country getaway or future homesite on this beautiful 5.5-acre wooded property in Enville, Tennessee. Conveniently located with road frontage on both Moss Loop and Highway 22A, this parcel offers easy access and multiple options for driveway placement or building layout. A gravel

  

  Melanie Malone

  Crye-Leike Elite

  00 Old State Highway 22a, Enville, TN 38332
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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

  Lot 7 Greystone Cove, Henderson, TN 38340
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  /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
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  /9

  $750,000

  • Land
  • 7 Acres
  • $107,143 per Acre

  3695 US Highway 45 N, Henderson, TN 38340

  Position your business for success with this exceptional ± or - 7-acre commercial tract offering over 250 feet of frontage on highly traveled US Highway 45 in Henderson, Tennessee. With outstanding visibility, easy access, and ample space for development, this property presents an outstanding opportunity for investors, developers, and owner-users alike. Ideally suited for light industrial,

  

  Chris Miller

  Crye-Leike Elite

  3695 US Highway 45 N, Henderson, TN 38340
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  /66

  $549,000

  • 4 Beds
  • 5 Baths
  • 3,376 Sq Ft

  50 Braund Rd, Henderson, TN 38340

  Just had a brand new roof put on! Let me tell you about this one like I would if we were standing in the kitchen together. This isn't just a four bedroom, five bath home with a basement — it's space to actually live. Room for everyone, whether that's kids, guests, or hosting the holidays without feeling stacked on top of each other. The basement gives you even more flexibility for a second living

  

  Destiny Burns

  Stellar Realty Group

  50 Braund Rd, 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

  Lot 5 Greystone Cove, Henderson, TN 38340
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  /44

  $744,000

  $16K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,845 Sq Ft

  25 Oak Ridge Dr, Henderson, TN 38340

  Looking for country living with plenty of space? Welcome to Oakmont Estates. This 5 bedroom, 3.5 bath home offers approximately 4,845 square feet of living space on 2.05 acres in Chester County, with no city taxes. Two additional bonus rooms could potentially serve as sixth and seventh bedrooms, guest rooms, entertainment areas, or flexible living spaces. Inside, the home features a functional

  

  Darrick Mann

  Crye-Leike Elite

  25 Oak Ridge Dr, Henderson, TN 38340
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  /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
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  /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

  Lot 22 Greystone Cove, Henderson, TN 38340
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  /89

  $896,000

  $31K PRICE DROP

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

  575 Homestead Ln, Henderson, TN 38340

  MOTIVATED SELLERS! If you've been looking for a home with room for everyone and then some, this one is worth a look. Tucked away on approximately 3.11 acres at the end of a dead-end road, this 5-bedroom, 4 full bath home offers the space, privacy, and flexibility that's hard to find. The main floor features the primary suite, two additional bedrooms, an office, and laundry room. Upstairs, you'll

  

  Destiny Burns

  Stellar Realty Group

  575 Homestead Ln, Henderson, TN 38340
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  /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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  /41

  $325,000

  $18K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,363 Sq Ft

  1160 Wilson School Rd, Henderson, TN 38340

  Warmth, character, and room to enjoy. This beautiful home on nearly 3 acres offers the space and features you've been seeking. From the moment you step inside, you'll notice the craftsmanship and attention to detail with hardwood floors, rich custom woodwork, detailed trim, and architectural accents that create a timeless and inviting feel throughout the home. Designed with both everyday living

  

  Brandi Wilson Isom

  RE/MAX Realty Source

  1160 Wilson School Rd, Henderson, TN 38340
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  /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, membership owned communities. Located in Deanburg Hills Incorporated, 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

  

  Dylan Jones

  Southern LifeStyle Properties

  1380 Harrison Rd, Pinson, TN 38366
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  /23

  $480,000

  • Land
  • 143.34 Acres
  • $3,349 per Acre

  00 S State Route 22a S, Enville, TN 38332

  Don't miss this rare opportunity to own 143.34 unrestricted acres in a fantastic location just off Hwy 22 in Enville, Tennessee. This versatile tract offers convenient access to Lexington, Henderson, and Adamsville while still providing the privacy, nature, and wide-open space buyers are looking for. With electricity available at the road and multiple ideal building sites, this property is

  

  Lori Yarbro

  Evans Real Estate

  00 S State Route 22a S, Enville, TN 38332
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  /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

  Lot 18 Greystone Cove, Henderson, TN 38340
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  /65

  $825,000

  $25K PRICE DROP

  • 5,952 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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  /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

  Lot 21 Greystone Cove, Henderson, TN 38340
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  /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
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  /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

  Lot 8 Greystone Cove, Henderson, TN 38340
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  /31

  $70,000

  • 3 Beds
  • 2 Baths
  • 2,009 Sq Ft

  425B Second St, Henderson, TN 38340

  Rare investment opportunity in the heart of Henderson! This historic home sits on approximately 1.2 acres in an established neighborhood and offers tremendous potential. The home was damaged by fire several years ago and is being sold as-is, but much of the structure remains, making it a strong candidate for restoration by the right contractor. The oversized lot also presents excellent

  

  Joshua Trammell

  EXIT Realty Blues City

  425B Second St, Henderson, TN 38340
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  /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 Isom

  RE/MAX Realty Source

  0 Old Sobby Rd, Bethel Springs, TN 38315
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  /38

  $579,900

  $20K PRICE DROP

  • 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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /45

  $469,500

  • Land
  • 180 Acres
  • $2,608 per Acre

  3385 Tennessee 125, Henderson, TN 38340

  180+/- acres | Hunting • Recreation • Timber | Silerton, TNThe Big Rock Tract is a 180± acre hunting, timber, and potential homesite property in Silerton, Tennessee, positioned along the edge of Chickasaw State Forest with frontage on Hwy 125, Hickory Grove Cemetery Lane, and Big Rock Trail. This tract combines the privacy and habitat of a large recreational property with the practical

  Austin Carroll Tutt Land Company

  3385 Tennessee 125, Henderson, TN 38340
• 

  

  /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
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  /33

  $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
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  /47

  $2,999,900

  • 4 Beds
  • 5 Baths
  • 4,570 Sq Ft

  60 Proctor Rd, Henderson, TN 38340

  2602272 RF Located in Henderson, Tennessee, this exceptional luxury estate offers upscale living, premium construction, and fully equipped equestrian property across approximately 138 private acres surrounded by wildlife, trails, and natural beauty. With quick access to Jackson, Memphis, Nashville, US Highway 45, and Interstate 40, this property delivers both privacy and convenience. A circular

  Chris Carothers West Tennessee

  60 Proctor Rd, Henderson, TN 38340
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  /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
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  /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
• 

  

  /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
• 

  

  /22

  $125,000

  • Land
  • 18.84 Acres
  • $6,635 per Acre

  1555 U S 45, Henderson, TN 38340

  18.84-acre Development Opportunity | US Hwy 45 | Henderson, TNPositioned along the highly traveled corridor of US Highway 45 in Henderson, this 18.84 acre tract presents a compelling opportunity for investors, developers, and end-users seeking visibility and long-term growth potential in a great location.Currently zoned agricultural, the property offers rezoning potential to

  Austin Carroll Tutt Land Company

  1555 U S 45, Henderson, TN 38340

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