Homes for Sale near Chester County High School

• 

  

  

  /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) 415-3296

  575 Homestead Ln, 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

  $125,000

  • 2 Beds
  • 1 Bath
  • 1,168 Sq Ft

  447 Mifflin Ave, Henderson, TN 38340

  This cute cottage is ideal for First-Time Buyers, Downsizers, or Investors!This well-maintained 2 bedroom, 1 bath home is full of charm and modern touches. Recent updates include luxury vinyl flooring throughout the living room, dining room, and kitchen. The kitchen has been recently updated with stylish cabinets, subway tile backsplash, countertops, dishwasher, microwave vent hood, plumbing

  

  Brandi Wilson

  RE/MAX Realty Source

  (731) 316-0543

  447 Mifflin Ave, Henderson, TN 38340
• 

  

  

  /15

  $54,500

  • Land
  • 8 Acres
  • $7,267 per Acre

  0 Highway 100, Henderson, TN 38340

  Looking for Land?Here's your opportunity! Approximately 7.5 acres of unrestricted land in Chester County is ready for you to make it your own. Whether you're dreaming of building a home, starting a mini farm, or just having space to spread out, this property offers endless potential with no restrictions. Don't miss out!

  

  Destiny Burns

  Stellar Realty Group

  (731) 497-1325

  0 Highway 100, Henderson, TN 38340
• 

  

  

  /20

  $49,900

  • 2 Beds
  • 1 Bath
  • 894 Sq Ft

  7455 Tennessee 100, Jacks Creek, TN 38347

  Whether you're an investor searching for your next fix-and-flip or a homebuyer looking for an affordable property you can make your own, this one has potential written all over it. Located just outside the city limits in the peaceful community of Jacks Creek, this 2-bedroom, 1-bath home offers 894 square feet of space and is zoned for Chester county schools - one of the most desirable school

  

  Dylan Jones

  Southern LifeStyle Properties

  (731) 472-8303

  7455 Tennessee 100, Jacks Creek, TN 38347
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  /32

  $224,900

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  415 Galbraith Ave, Henderson, TN 38340

  Welcome to your Home! This completely remodeled three-bedroom, 2 1/2 bath residence boasts a versatile bonus room that can easily be converted into a fourth bedroom with the addition of an interior door. Enjoy the elegance of luxury vinyl plank flooring throughout, complemented by a stunning, all-new kitchen featuring modern appliances, sleek cabinets, beautiful countertops, and stylish

  

  Destiny Burns

  Stellar Realty Group

  (731) 318-5491

  415 Galbraith Ave, Henderson, TN 38340
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  /42

  $499,900

  • 6 Beds
  • 4.5 Baths
  • 5,922 Sq Ft

  562 Old Jackson Rd, Henderson, TN 38340

  This spacious home is ideal for a large or extended family, offering comfort, functionality, and room to grow. The main floor features a cozy living room, a den, formal dining area, 3 bedrooms, and 2.5 bathrooms—perfect for daily living and entertaining. The fully finished walkout basement adds even more living space with its own kitchen, den, living room, 3 additional bedrooms, and 2 full

  

  Destiny Burns

  Stellar Realty Group

  (731) 330-2632

  562 Old Jackson Rd, Henderson, TN 38340
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  /26

  $384,000

  • 3 Beds
  • 2 Baths
  • 1,912 Sq Ft

  316 Meadow Brook Dr, Henderson, TN 38340

  Welcome to this beautiful brick home located on the sought-after Meadowbrook Drive in Henderson, Tennessee! This charming residence features three spacious bedrooms and two full baths, all designed around an inviting open floor plan. Enjoy the outdoors with a brand new deck, perfect for entertaining or relaxing. Conveniently situated near Freed Hardeman University and downtown Henderson, this

  

  Destiny Burns

  Stellar Realty Group

  (731) 535-7172

  316 Meadow Brook Dr, Henderson, TN 38340
• 

  

  /15

  $235,000

  • Land
  • 32 Acres
  • $7,388 per Acre

  305 Smith Rd, Luray, TN 38352

  Land Land Land! This incredible opportunity features approximately 31.81 acres of unrestricted land, ready for you to transform into your dream property. The land has already been cleared for building, perc tested, and includes two 30 ft culverts installed for easy access. Don't miss out on this rare find—land like this is hard to come by!

  

  Destiny Burns

  Stellar Realty Group

  (731) 747-3504

  305 Smith Rd, Luray, TN 38352
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  /39

  $469,900

  • 4 Beds
  • 3 Baths
  • 3,064 Sq Ft

  210 Tall Pines Rd, Henderson, TN 38340

  Discover your dream home in this beautiful brick residence located just minutes from town, offering the benefits of only county taxes! This charming property features four spacious bedrooms and a versatile bonus room upstairs complete with a full bath, perfect for guests or a home office. Enjoy serene evenings on the screened-in porch, all nestled on just over 1 acre at the end of a peaceful

  

  Destiny Burns

  Stellar Realty Group

  (731) 201-9415

  210 Tall Pines Rd, Henderson, TN 38340
• 

  

  /31

  $579,900

  6145 Tennessee 225, Henderson, TN 38340

  You will never find a more beautiful piece of land in Chester County! This stunning +/- 79.97-acre property is a true gem, featuring a natural spring and a serene pond that enhance its picturesque landscape. Approximately 40 acres fenced and ready for a cattle farmer, this land offers the perfect setting for livestock.With timber that will be ready for cutting in just five years, there's

  

  Destiny Burns

  Stellar Realty Group

  (731) 224-4661

  6145 Tennessee 225, Henderson, TN 38340
• 

  

  /20

  $469,000 New Construction

  • 3 Beds
  • 2 Baths
  • 2,450 Sq Ft

  550 Trice Rd, Henderson, TN 38340

  **Discover Luxury Living in Magnolia Springs!** This stunning property, currently under construction in the highly sought-after subdivision of Magnolia Springs in Chester County, features a striking white brick exterior. Offering 3 spacious bedrooms and 2 full baths, the master bath is a true retreat with a relaxing soaking tub and a beautifully tiled shower. The dedicated office space

  

  Destiny Burns

  Stellar Realty Group

  (731) 251-4730

  550 Trice Rd, Henderson, TN 38340
• 

  

  /20

  $269,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,515 Sq Ft

  757 Christi Loop, Henderson, TN 38340

  **Incredible Opportunity: $3,000 Credit Towards Closing Costs!**Don't miss your chance to own this brand-new custom-built home! With approximately 1,515 heated square feet and around 2,026 square feet under roof, this stunning residence combines luxury and comfort. Inside, you'll find exquisite custom cabinets, elegant quartz countertops, and high-end luxury vinyl flooring

  

  Destiny Burns

  Stellar Realty Group

  (731) 462-4165

  757 Christi Loop, Henderson, TN 38340
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  /40

  $249,900

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  245 Henderson Rd, Pinson, TN 38366

  New Listing!! Welcome to your own slice of country living!Located outside of Historic Pinson, this 3-bedroom, 2 full bath home offers 1,560 sq ft of comfortable living space, featuring a cozy breakfast room, living room with wood burning fireplace, updated kitchen with new flooring, and renovated bathrooms.Situated on 3.78 sprawling acres, this "farmette" is fully equipped with

  Leigh Ann Smalley-Ward Fisher Realty & Auction

  245 Henderson Rd, Pinson, TN 38366
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  /11

  $49,000

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

  0 Cash School Rd, Enville, TN 38332

  Private and peaceful tract just outside town. No rules, no neighbors on top of you. Covered in 25 year loblolly pine and mostly level ground. Ideal for a homestead, camper, or long-term hold. Power at the road. Owner Financing Available.

  Ronald (Ron) Daniel, II R. W. Daniel Realty Group

  0 Cash School Rd, Enville, TN 38332
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  /38

  $541,800

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

  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 regions thriving wildlife population.Known for its trophy bucks and exceptional turkey hunting,

  Annah Barnes

  Old Cave Springs Rd, Henderson, TN 38340
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  /18

  $503,500

  • Land
  • 92 Acres
  • $5,491 per Acre

  1450 Busby Ln, Henderson, TN 38340

  Rolling fields, open pasture, and scattered wooded areas create a diverse landscape that's both functional and beautiful. Whether you're looking to cultivate crops, raise animals, or simply enjoy wide-open spaces, this land offers both privacy and potential. Complete with a classic barn, perfect for storage, livestock, or conversion into a workshop, 2 active wells, and 3 manufactured trailers for

  Robert Eatman Hickman Realty Group Inc.-Jack

  1450 Busby Ln, Henderson, TN 38340
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  /100

  $1,250,000

  • 5 Beds
  • 5 Baths
  • 3,090 Sq Ft

  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 2 half

  James Carothers Hickman Realty Group Inc

  375 Glendale Rd, Henderson, TN 38340
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  /25

  $115,000

  • Land
  • 17 Acres
  • $6,694 per Acre

  0 Sanford Rd, Henderson, TN 38340

  Purchase Price: $115,000 with $15k down $2,249.79 for 60 months at 12.5% OR $1,582.87 for 120 months at 14.5%This exceptional 17.18-acre property sits just outside Henderson city limits on Sanford Road, offering a perfect blend of natural beauty and development potential. Recently surveyed, the land features a creek flowing consistently along one boundary, creating a picturesque

  Justin Piche Scout Land Group

  0 Sanford Rd, Henderson, TN 38340
• 

  

  /11

  $44,900

  • Land
  • 13 Acres
  • $3,376 per Acre

  285 Sherry Ln, Enville, TN 38332

  Discover your private sanctuary..13.3 Acres of Secluded Land. Are you looking for a hunting retreat or are you ready to escape the hustle and bustle of city life? Imagine owning 13.3 acres of pristine, secluded lane that offers you the perfect blend of tranquility and adventure. This is an opportunity to create your own private sanctuary far away from the noise and distractions of everyday

  Morgan Lewis Hickman Realty Group, Inc.-Mil

  285 Sherry Ln, Enville, TN 38332
• 

  

  /50

  $4,250,000

  • 5 Beds
  • 8 Baths

  140 Lake Shore Ln, Henderson, TN 38340

  Nestled on 151 pristine acres, this sprawling 8,264 square-foot estate offers unparalleled luxury and privacy. A true masterpiece of design and craftsmanship, the home features an open, expansive layout, high-end finishes, and sweeping views of the surrounding natural beauty. Step outside and discover your own personal paradise. A beautifully designed pool and hot tub overlook the tranquil,

  Brandon Pendergrass Hayden Outdoors Real Estate

  140 Lake Shore Ln, Henderson, TN 38340
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  /24

  $120,050

  • Land
  • 49 Acres
  • $2,450 per Acre

  0 Grooms Rd, Henderson, TN 38340

  PT-04a is the northern 49+/- acre portion of PT-04. It is located in the Pine Top area in the southwest quadrant of Chester County. It consists of 49+/- acres of ridges and rolling hills. The ridgetops contain a 3 to 4 year old loblolly pine plantation, while the drainages consist of varying age classes of mixed hardwoods and pine. There is roughly 2,000 feet of frontage along Grooms

  Austin Carroll Tutt Land Company

  0 Grooms Rd, Henderson, TN 38340
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  /32

  $431,900

  • Land
  • 192 Acres
  • $2,249 per Acre

  0 Grooms Rd, Henderson, TN 38340

  PT-03 is located on Grooms Rd and Hurst Rd in Chester County. This hunting/recreational and timber tract contains approximately 192 acres of ridgetops with rolling and sloping hills. It contains roughly 85 acres in mature upland hardwoods and pine, as well as another 95 acres in loblolly pine plantations planted in 2021. There is a good ridge system that could be used for additional roads/trails,

  Austin Carroll Tutt Land Company

  0 Grooms Rd, Henderson, TN 38340
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  /35

  $123,930

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

  0 Grooms Rd, Henderson, TN 38340

  PT-01 is located in southwest Chester Co. on Grooms Rd. This recreational and hunting tract contains 55.08 acres, of which approximately 15 acres being mature loblolly pine with the remaining acreage being a stand of two year old loblolly pine. This habitat diversity makes for great deer and turkey hunting opportunities.The topography is considered rolling and sloping hills. It has

  Austin Carroll Tutt Land Company

  0 Grooms 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
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  /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
• 

  

  /20

  $299,900

  • 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
• 

  

  /40

  $349,900

  • 3 Beds
  • 2 Baths
  • 2,000+ Sq Ft

  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
• 

  

  /23

  $264,900

  • 3 Beds
  • 2 Baths
  • 1,523 Sq Ft

  90 Fieldcrest Cove, Henderson, TN 38340

  This is a charming three bedroom, two bath home in the heart of Chester County! This well-cared-for property offers engineered hardwood floors in the main living areas and a desirable split floorplan for added comfort and privacy. Outside, you'll love the oversized backyard and the 12x20 shop—perfect for storage, hobbies, or a home workshop. Full of charm and functionality, this home is one you

  Madison Balding Town and Country

  90 Fieldcrest Cove, Henderson, TN 38340
• 

  

  /32

  $499,000

  • 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 spacious

  Brent West Crye-Leike Elite

  137 Gibson Dr, Henderson, TN 38340
• 

  

  /21

  $289,900

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  380 Melodie Cir, Henderson, TN 38340

  MOTIVATED SELLER! Built in 2024, this beautiful barndominium offers 3 bedrooms, 2.5 bathrooms, and nearly 1,700 sq ft of modern living on a 0.78-acre lot. Enjoy 10-foot ceilings throughout and an open-concept layout with a vaulted living room that adds warmth and charm.The kitchen features butcher block countertops and a spacious walk-in pantry with a sliding barn door. Epoxy floors run

  Michelle Lilly Lilly Realty

  380 Melodie Cir, Henderson, TN 38340
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  /37

  $325,000

  • 4 Beds
  • 2.5 Baths
  • 1,948 Sq Ft

  2925 Tennessee 100, Henderson, TN 38340

  Welcome to 2925 State Route 100 W in Henderson! This beautifully updated 4 bedroom, 2.5 bath home is tucked away on a peaceful 2.65 acre lot. Located just half a mile from West Chester Elementary., This home provides both convenience and a serene setting. Inside, you will find nearly 2,000 square feet of living space with modern upgrades throughout-including updated (LVP) flooring, kitchen

  Jennifer Scott RE/MAX Realty Source

  2925 Tennessee 100, 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
• 

  

  /25

  $259,000

  • 3 Beds
  • 2 Baths
  • 2,000+ Sq Ft

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

  Discover your dream mini-farm on 2.86 picturesque acres! This unique property boasts a charming barn, stables, fenced pasture, and more – perfect for embracing the rural lifestyle. The beautifully 2146 sq ft renovated 3-bedroom home features a modern kitchen, updated HVAC, and stylish finishes throughout. Nestled in a peaceful setting, this home offers a tranquil escape while remaining

  Elizabeth Burlew eXp Realty, LLC

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

  

  /21

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  1510 Talley Store Rd, Henderson, TN 38340

  Welcome to your dream retreat where country charm meets convenience! This immaculately kept one-level, 3-bedroom, 2-bath home sits on a spacious 1-acre lot with a privacy fence, offering the perfect blend of seclusion and accessibility. Step outside and enjoy the huge covered deck, ideal for relaxing, entertaining, or simply taking in the peaceful surroundings.Inside, you'll find a bright and

  Scott Shelton Crye-Leike Elite

  1510 Talley Store Rd, Henderson, TN 38340
• 

  

  /22

  $284,500

  • 3 Beds
  • 3 Baths
  • 2,440 Sq Ft

  225 E Third St, Henderson, TN 38340

  BEAUTIFUL BRICK HOME WITHIN 2 BLOCKS FROM FHU, WITH SO MUCH TO OFFER A FAMILY, DEN, LIVING,ROOM, SUNROOM, 2 BEDROOMS,DOWN WITH 2 BATHS, LARGE BONUS ROOM UP WITH BATH, PLUS AN OFFICE AREA, FIREPLACE W/GAS LOGS IN DEN, LARGE FENCED IN BACKYARD FOR OUR FUR BABIES OR YOUR REGULAR BABIES AND SO MUCH MORE. THIS IS A MUCH SEE.

  Linda Carter Casey Realtors

  225 E Third St, Henderson, TN 38340
• 

  

  /47

  $529,900

  • 3 Beds
  • 2 Baths
  • 2,201 Sq Ft

  480 Ridgewood Dr, Henderson, TN 38340

  Beautiful all brick home w/neutral paint color, 3 bedrooms, 2 baths w/ bonus room w/carpet upstairs, w/separate heat/air units. Hardwood floors throughout w/ carpet only in the two additional bedrooms. Tile in bathrooms and laundry room. Very large Laundry room. Home sits on 1.3 acres of beautiful fully sodded Bermuda hybrid grass with planted trees scattered about, Plantation Shutters

  Linda Carter Casey Realtors

  480 Ridgewood Dr, Henderson, TN 38340
• 

  

  /39

  $305,000

  • 4 Beds
  • 2 Baths
  • 2,000+ Sq Ft

  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
• 

  

  /22

  $254,900

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

  129 N Carolina Ave, Henderson, TN 38340

  This updated 3 bedroom 2 bath home in Henderson, TN could be a perfect fit for you. It features fresh paint, new flooring, fully renovated kitchen, with granite countertops, new stove, microwave and dishwasher . Home also has new water heater, 1 new HVAC and updated plumbing. The master suite includes an oversized walk-in closet that you can customize to your liking. Additional highlights include

  Janet DiChiara EXIT Realty Blues City

  129 N Carolina Ave, Henderson, TN 38340
• 

  

  /20

  $260,000

  • 3 Beds
  • 2 Baths
  • 1,339 Sq Ft

  200 Westwood Cove, Henderson, TN 38340

  Discover modern living at 200 Westwood Cove, a brand-new 3-bedroom, 2-bath home featuring a spacious open-concept living room, sleek kitchen with new appliances, a large backyard patio, and a 2-car garage. Located just 3 minutes from Henderson, TN, this move-in-ready home offers the perfect blend of convenience and comfort—all with no city taxes in a peaceful private cove.

  Brent West Crye-Leike Elite

  200 Westwood Cove, Henderson, TN 38340

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