Chester County TN Houses for Sale

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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) 415-3296

  575 Homestead Ln, Henderson, TN 38340
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  /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
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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
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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
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  /54

  $299,000

  • 4 Beds
  • 2 Baths
  • 2,065 Sq Ft

  1710 Clarks Creek Rd, Henderson, TN 38340

  Discover this charming one-owner home nestled in the tranquil countryside! Set on approximately 2 acres, this property features a serene pond, perfect for relaxation and outdoor enjoyment. With no restrictions, you have the freedom to create your ideal living space. Inside, the home boasts 4 spacious bedrooms and 2 well-appointed bathrooms, providing ample space for family and guests. A versatile

  

  Destiny Burns

  Stellar Realty Group

  (731) 462-3786

  1710 Clarks Creek Rd, Henderson, TN 38340
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  /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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  /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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  /50

  $4,250,000

  • 5 Beds
  • 4 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

  140 Lake Shore Ln, Henderson, TN 38340
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  /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
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  /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
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  /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
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  /23

  $264,900 Open Sun 2PM - 4PM

  • 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
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  /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 Open Sat 11AM - 1PM

  • 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
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  /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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  /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
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  /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
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  /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
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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
• 

  

  /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
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  /66

  $469,900

  • 4 Beds
  • 3 Baths
  • 1,916 Sq Ft

  130 Moss Loop, Enville, TN 38332

  Looking for a serene property? Then check out this beautiful home! 4BR, 2BA, attached garage, detached shop/garage, great location with a beautiful view. Large deck on the back to enjoy your morning coffee and enjoy the view. Property sits on 20 acres. Call today for a showing!

  Linda Carter Casey Realtors

  130 Moss Loop, Enville, TN 38332
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  /33

  $279,900

  • 6 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  208 Fourth St, Henderson, TN 38340

  Charming 6 BR 2.5 BA Home w/Office in Henderson, TN - Prime Location near Freed Hardemon UniversityWelcome to your dream home in the heart of Henderson! This exquisite property, ideally situated on a corner lot, offers unparalleled convenience, being within walking distance to Freed Hardemon University, Main St, and all that Henderson has to offer.Key Features:Complete Makeover: This home has

  Richard Emison NextHome 383 Real Estate

  208 Fourth St, Henderson, TN 38340
• 

  

  /23

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,475 Sq Ft

  90 Mitchell Ln, Henderson, TN 38340

  Brent West Crye-Leike Elite

  90 Mitchell Ln, Henderson, TN 38340
• 

  /2

  $289,900 New Construction

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

  454 Old Jackson Rd, Henderson, TN 38340

  Don't miss your chance to own this beautifully designed 3 bed, 2 bath home with 1,560 sqft of modern comfort at 454 Old Jackson Rd in Henderson, TN! Step into a spacious open-concept layout that's perfect for entertaining and everyday living. The heart of the home is the luxurious kitchen—featuring sleek finishes, ample counter space, and premium appliances that will impress any home chef. With

  Brent West Crye-Leike Elite

  454 Old Jackson Rd, Henderson, TN 38340
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  /29

  $189,900

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft

  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
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  /53

  $650,000

  • 4 Beds
  • 3.5 Baths
  • 3,331 Sq Ft

  1710 Short Farrow Rd, Henderson, TN 38340

  Escape to your own slice of paradise with this stunning 25-acre estate in Chester County with county taxes only! Built in 2014 from plans featured in a Southern living magazine, this 3,331 sq. ft. masterpiece blends modern elegance with serene country living. Surrounded by nearly 21 acres of lush, wooded landscape and over 4 acres of open pasture, this property is a haven for wildlife and nature

  Riley Ragan Ragan Realty Group

  1710 Short Farrow Rd, Henderson, TN 38340
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  /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
• 

  

  /23

  $214,900

  • 4 Beds
  • 2 Baths
  • 2,570 Sq Ft

  934 Sand Ave, Henderson, TN 38340

  Spacious 4 bedroom, 2 bathroom home located inside Chester County city limits. This unique property features 2 bedrooms and 1 bathroom upstairs, with an additional 2 bedrooms, 1 bathroom, and a huge living room in the basement. The basement space could be utilized as a mother-in-law suite or guest quarters. Situated on a large lot, the home offers a deck on the upper level and a concrete patio

  Linda Carter Casey Realtors

  934 Sand Ave, Henderson, TN 38340
• 

  

  /20

  $132,900

  • 3 Beds
  • 1 Bath
  • 1,125 Sq Ft

  1127 Tucker Cove, Henderson, TN 38340

  Quaint 3 bedroom, 1 bathroom brick home in Henderson city situated on over 1 acre of land. This cozy property features a refrigerator, stove, and dishwasher, making it perfect for first-time homebuyers or investors. Please schedule showings with a 24-hour notice, available to show M-F after 4pm and after 12pm weekends. Ideal opportunity to own a piece of Henderson's real estate market.

  Linda Carter Casey Realtors

  1127 Tucker Cove, Henderson, TN 38340
• 

  

  /22

  $149,800

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  234 Tulip St, Henderson, TN 38340

  Charming 3 bedroom, 1 bathroom brick/vinyl home in the heart of Henderson city. Situated on a spacious lot with a large backyard adorned with a stunning shade tree. This cozy abode comes complete with a refrigerator, stove, and dishwasher. Ideal as a starter home or as a lucrative investment property. Showings available M-F after 2pm and weekends after 12pm. Dogs in the home

  Linda Carter Casey Realtors

  234 Tulip St, Henderson, TN 38340
• 

  

  /27

  $179,500

  • 3 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  7435 Tennessee 100, Jacks Creek, TN 38347

  Brick, 3 bedroom, 1.5 bath, with drive\walk out basement. Storage building. Eat-in-kitchen, lots of cabinets! Laundry is in primary bedroom but could be moved back to the basement. Large, covered porch off the primary bedroom or could be more covered parking. Basement has a safe room for all you valuables and a garage door in the basement. Lots of different uses for a walkout basement. Don't miss

  Chris Sherrod CRYE*LEIKE Blue Skies Real Es

  7435 Tennessee 100, Jacks Creek, TN 38347
• 

  

  /12

  $160,500

  • 2 Beds
  • 1 Bath
  • 800+ Sq Ft

  3515 Pleasant Springs Rd, Pinson, TN 38366

  Charming 2-bedroom home nestled on 4 acres in the country. Enjoy peaceful mornings and relaxing afternoons on a cover front porch or take a stroll to the back of the property to your own natural creek. Lots of area to entertain, garden or just enjoy the wide-open space. Minutes from the State Park, Golf Course, and Downtown Henderson. Cellar with entrance in the Kitchen can provide shelter in

  Misty Buss Molly Moore Realty

  3515 Pleasant Springs Rd, Pinson, TN 38366

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