29

Chester County TN Homes under $300,000

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  • /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!

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    (731) 747-3504

    305 Smith Rd, Luray, TN 38352
  • /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

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    (731) 318-5491

    415 Galbraith Ave, 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

    Agent Photo

    Destiny Burns

    Stellar Realty Group

    (731) 462-4165

    757 Christi Loop, Henderson, TN 38340
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /37

    $249,900

    • 3 Beds
    • 2 Baths
    • 1,485 Sq Ft

    3605 Old Jacks Creek Rd, Henderson, TN 38340

    Welcome to 3605 Old Jacks Creek Road, Henderson, TN!Nestled on 3.26 beautiful acres, this charming 3-bedroom, 2-bath home offers peaceful country living just minutes from town. Step inside to find a cozy living room featuring a fireplace and brand-new flooring throughout the main living area, creating a warm and inviting atmosphere. The spacious kitchen and dining area flow perfectly for

    Sheila Darnell EXIT Realty Blues City

    3605 Old Jacks Creek Rd, Henderson, TN 38340
  • /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
  • /23

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,707 Sq Ft

    1100 Stewart Rd, Henderson, TN 38340

    Private storm shelter, den is currently being used as 4th bedroom and has a door to large back deck and fenced yard. Please give tenant 24 hour notice to show. Seller is obligated to give tenants a 30 day notice to vacate. This will be done upon either of the following; successful closing on the property or the seller the receives from the buyer a non-refundable $10,000 deposit toward the

    Linda Carter Casey Realtors

    1100 Stewart Rd, Henderson, TN 38340
  • /36

    $259,900

    • 3 Beds
    • 2.5 Baths
    • 1,840 Sq Ft

    210 Baker Rd, Henderson, TN 38340

    Welcome to your new home in Henderson, Tennessee! This beautiful property boasts five acres of land equipped with three shops and an in-ground swimming pool. The home features over 1800 square feet of living space with 3 bedrooms and 2.5 bathrooms. Weary of storms? Don't worry this property has its own storm shelter! Don't miss the opportunity to make this your next home!

    Aaliyah Cupples Stellar Realty Group

    210 Baker Rd, Henderson, TN 38340
  • /17

    $221,500

    • 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
  • /12

    $235,000

    • Land
    • 50 Acres
    • $4,691 per Acre

    0 Arl Bailey Rd, Finger, TN 38334

    Capture the essence of distinction on this prestigious 50.1-acre wooded estate in rural Chester County. With a perennial spring, numerous prime building locations, and unparalleled serenity, this property offers the ultimate retreat. Strategically located near Henderson, Lexington, Jackson, and the Tennessee River, convenience harmonizes with seclusion, presenting a unique opportunity for refined

    Larry Roberts Casey Realtors

    0 Arl Bailey Rd, Finger, TN 38334
  • /33

    $219,900

    • 3 Beds
    • 2 Baths
    • 1,276 Sq Ft

    661 Mifflin Ave, Henderson, TN 38340

    Charming 3BR/2BA Home Near FHU - Built in 2023!Welcome to 661 Mifflin Ave - a beautifully crafted 3-bedroom, 2-bath home featuring timeless board and batten siding and modern finishes throughout. Built in 2023, this home offers a fresh, move-in-ready feel and is ideally located within walking distance to Freed-Hardeman University, local schools, and shopping.Step inside to

    Richard Emison NextHome 383 Real Estate

    661 Mifflin Ave, Henderson, TN 38340
  • /24

    $239,900

    • 3 Beds
    • 2 Baths
    • 1,850 Sq Ft

    320 Benson Rd, Reagan, TN 38368

    2.17 Acres country living. Newly updated kitchen with granite countertops, stainless appliances, cabinets, coffee bar, and open to living room, rec room (which could be 4th bedroom). Main bedroom features private bath, double sinks, shower/commode room, 5x5 closet, and private access door to backyard. Outside was updated with siding, cedar posts, and shutters to match. 14x22 screened in porch

    Andrea Crawford RE/MAX Unlimited

    320 Benson Rd, Reagan, TN 38368
  • /32

    $250,000

    • 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
  • /32

    $259,000

    • 2 Beds
    • 1 Bath
    • 1,200+ Sq Ft

    513 Crook Ave, Henderson, TN 38340

    This upscale, modern farmhouse inspired home offers the perfect blend of upscale living and affordability. It boasts 1400 sq ft of living space on .2 acres right in the heart of Henderson. This beautifully crafted home features a spacious floor plan, high-end finishes, and functional, charming rooms. On the main floor, you will find a welcoming entry, a stunning galley kitchen, living room,

    Ashton Roberts Molly Moore Realty

    513 Crook Ave, Henderson, TN 38340
  • /3

    $260,000

    • Land
    • 2.70 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
  • /34

    $203,000

    • 4 Beds
    • 2 Baths
    • 1,949 Sq Ft

    241 Crook Ave, Henderson, TN 38340

    Vintage 4-bedroom, 2-bath home that's been totally revamped! With new flooring, fresh paint, and cool light fixtures, it's ready for you to move right in. It's super close to Freed Hardeman and all the fun stuff downtown Henderson has to offer.You'll love the big, roomy spaces with tons of storage for all your stuff. The kitchen's got shiny stainless steel appliances that are perfect for

    Katie Mitchell Townsend Compass RE

    241 Crook Ave, Henderson, TN 38340
  • /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
  • /10

    $204,900

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft

    11715 State Route 22a S, Enville, TN 38332

    REMODELED!!! 1512 sq ft, 3 bedroom/2bath vinyl w/detached 2 car garage sits on 1.12 acres m/l. Priced to sell @ $204,900. Call today for your tour!!

    Shirley McKee Coldwell Banker McKee Realty

    11715 State Route 22a S, Enville, TN 38332
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